# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Aakeroy, C.' _publ_contact_author_name 'Aakeroy, C.' _publ_contact_author_email aakeroy@ksu.edu _publ_section_title ; Mapping out the synthetic landscape for re-crystallization, co-crystallization and salt formation ; # Attachment '- allcifs.cif' data_ar0815m(A3) _database_code_depnum_ccdc_archive 'CCDC 772244' #TrackingRef '- allcifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; AR-1g-3 2-aminopyridine, 4-chlorobenzoic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C5 H6 N2) (C7 H5 O2 Cl) ; _chemical_formula_sum 'C12 H11 Cl N2 O2' _chemical_formula_weight 250.68 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Pn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 6.6153(14) _cell_length_b 7.9832(17) _cell_length_c 11.143(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.763(5) _cell_angle_gamma 90.00 _cell_volume 579.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3986 _cell_measurement_theta_min 3.15 _cell_measurement_theta_max 31.52 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.320 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6842 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 31.50 _reflns_number_total 3349 _reflns_number_gt 3155 _reflns_threshold_expression >2sigma(I) _reflns_Friedel_coverage 0.741 _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(4) _refine_ls_number_reflns 3349 _refine_ls_number_parameters 163 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0790 _refine_ls_wR_factor_gt 0.0771 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 1.31206(5) -0.07140(4) 0.70170(4) 0.02819(9) Uani 1 1 d . . . N11 N 0.07154(17) 0.53677(14) 0.61005(10) 0.0185(2) Uani 1 1 d . . . H11 H 0.195(3) 0.475(2) 0.6264(17) 0.022 Uiso 1 1 d . . . C12 C 0.0012(2) 0.57710(15) 0.49133(11) 0.0183(2) Uani 1 1 d . . . N12 N 0.10432(19) 0.52373(17) 0.40639(10) 0.0249(2) Uani 1 1 d . . . H12A H 0.215(4) 0.454(2) 0.4275(19) 0.030 Uiso 1 1 d . . . H12B H 0.050(4) 0.555(2) 0.332(2) 0.030 Uiso 1 1 d . . . C13 C -0.1809(2) 0.67453(17) 0.46475(12) 0.0214(2) Uani 1 1 d . . . H13 H -0.2330 0.7062 0.3832 0.026 Uiso 1 1 calc R . . C14 C -0.2806(2) 0.72237(17) 0.55703(13) 0.0231(2) Uani 1 1 d . . . H14 H -0.4037 0.7856 0.5390 0.028 Uiso 1 1 calc R . . C15 C -0.2021(2) 0.67856(16) 0.67958(12) 0.0235(3) Uani 1 1 d . . . H15 H -0.2702 0.7125 0.7440 0.028 Uiso 1 1 calc R . . C16 C -0.0265(2) 0.58656(16) 0.70216(11) 0.0205(2) Uani 1 1 d . . . H16 H 0.0288 0.5565 0.7836 0.025 Uiso 1 1 calc R . . C21 C 0.71072(18) 0.20955(15) 0.61766(11) 0.0176(2) Uani 1 1 d . . . C27 C 0.50914(19) 0.30194(16) 0.58519(12) 0.0191(2) Uani 1 1 d . . . O21 O 0.42670(13) 0.36028(13) 0.67133(8) 0.02077(19) Uani 1 1 d . . . O22 O 0.43622(15) 0.31383(15) 0.47398(9) 0.0287(2) Uani 1 1 d . . . C22 C 0.82948(19) 0.18274(16) 0.52680(12) 0.0204(2) Uani 1 1 d . . . H22 H 0.7818 0.2221 0.4465 0.024 Uiso 1 1 calc R . . C23 C 1.0168(2) 0.09907(18) 0.55255(13) 0.0224(3) Uani 1 1 d . . . H23 H 1.0986 0.0832 0.4911 0.027 Uiso 1 1 calc R . . C24 C 1.08162(19) 0.03923(17) 0.67032(13) 0.0213(2) Uani 1 1 d . . . C25 C 0.9662(2) 0.06238(16) 0.76223(12) 0.0210(2) Uani 1 1 d . . . H25 H 1.0122 0.0196 0.8417 0.025 Uiso 1 1 calc R . . C26 C 0.78107(18) 0.14978(17) 0.73546(11) 0.0195(2) Uani 1 1 d . . . H26 H 0.7021 0.1689 0.7978 0.023 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01640(13) 0.03070(16) 0.03803(18) 0.00199(14) 0.00623(11) 0.00281(12) N11 0.0179(5) 0.0229(5) 0.0148(4) 0.0001(4) 0.0032(3) -0.0010(4) C12 0.0193(6) 0.0206(6) 0.0150(5) 0.0000(4) 0.0028(4) -0.0019(4) N12 0.0254(6) 0.0352(7) 0.0145(5) 0.0027(5) 0.0047(4) 0.0082(5) C13 0.0222(6) 0.0237(6) 0.0183(5) 0.0012(5) 0.0030(4) 0.0025(5) C14 0.0224(6) 0.0228(6) 0.0249(6) 0.0013(5) 0.0060(5) 0.0030(5) C15 0.0277(7) 0.0228(6) 0.0224(7) -0.0010(5) 0.0107(6) -0.0009(5) C16 0.0246(6) 0.0226(6) 0.0149(5) 0.0000(4) 0.0051(4) -0.0029(5) C21 0.0147(5) 0.0206(5) 0.0174(5) -0.0022(4) 0.0026(4) -0.0035(4) C27 0.0166(5) 0.0235(6) 0.0173(5) 0.0006(4) 0.0032(4) -0.0016(4) O21 0.0182(4) 0.0273(5) 0.0167(4) -0.0017(3) 0.0026(3) 0.0016(3) O22 0.0232(5) 0.0462(6) 0.0161(4) -0.0003(4) 0.0013(4) 0.0088(4) C22 0.0192(6) 0.0226(6) 0.0199(6) -0.0008(4) 0.0050(4) -0.0034(4) C23 0.0180(6) 0.0265(6) 0.0243(6) -0.0019(5) 0.0079(5) -0.0028(4) C24 0.0137(5) 0.0227(6) 0.0271(6) -0.0025(5) 0.0026(4) -0.0006(4) C25 0.0178(6) 0.0241(6) 0.0202(6) -0.0004(5) 0.0010(4) -0.0007(4) C26 0.0163(5) 0.0242(6) 0.0178(5) -0.0019(4) 0.0028(4) -0.0004(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C24 1.7452(13) . ? N11 C16 1.3629(17) . ? N11 C12 1.3643(16) . ? N11 H11 0.94(2) . ? C12 N12 1.3274(18) . ? C12 C13 1.4221(19) . ? N12 H12A 0.92(2) . ? N12 H12B 0.89(2) . ? C13 C14 1.367(2) . ? C13 H13 0.9500 . ? C14 C15 1.4199(19) . ? C14 H14 0.9500 . ? C15 C16 1.361(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C22 1.3992(18) . ? C21 C26 1.4000(17) . ? C21 C27 1.5131(17) . ? C27 O22 1.2549(16) . ? C27 O21 1.2701(16) . ? C22 C23 1.3942(19) . ? C22 H22 0.9500 . ? C23 C24 1.3941(19) . ? C23 H23 0.9500 . ? C24 C25 1.390(2) . ? C25 C26 1.3968(17) . ? C25 H25 0.9500 . ? C26 H26 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 C16 N11 C12 122.25(12) . . ? C16 N11 H11 120.9(12) . . ? C12 N11 H11 116.9(12) . . ? N12 C12 N11 118.91(12) . . ? N12 C12 C13 123.14(12) . . ? N11 C12 C13 117.95(12) . . ? C12 N12 H12A 119.7(13) . . ? C12 N12 H12B 113.8(14) . . ? H12A N12 H12B 126.3(19) . . ? C14 C13 C12 119.72(12) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.68(13) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 118.17(13) . . ? C16 C15 H15 120.9 . . ? C14 C15 H15 120.9 . . ? C15 C16 N11 121.22(12) . . ? C15 C16 H16 119.4 . . ? N11 C16 H16 119.4 . . ? C22 C21 C26 119.22(11) . . ? C22 C21 C27 118.80(11) . . ? C26 C21 C27 121.98(11) . . ? O22 C27 O21 125.18(12) . . ? O22 C27 C21 116.65(11) . . ? O21 C27 C21 118.16(10) . . ? C23 C22 C21 120.86(12) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C24 C23 C22 118.60(12) . . ? C24 C23 H23 120.7 . . ? C22 C23 H23 120.7 . . ? C25 C24 C23 121.90(12) . . ? C25 C24 Cl1 119.35(11) . . ? C23 C24 Cl1 118.74(11) . . ? C24 C25 C26 118.71(12) . . ? C24 C25 H25 120.6 . . ? C26 C25 H25 120.6 . . ? C25 C26 C21 120.69(11) . . ? C25 C26 H26 119.7 . . ? C21 C26 H26 119.7 . . ? 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 -179.78(12) . . . . ? C16 N11 C12 C13 0.02(18) . . . . ? N12 C12 C13 C14 178.85(13) . . . . ? N11 C12 C13 C14 -0.94(19) . . . . ? C12 C13 C14 C15 1.2(2) . . . . ? C13 C14 C15 C16 -0.6(2) . . . . ? C14 C15 C16 N11 -0.31(19) . . . . ? C12 N11 C16 C15 0.61(19) . . . . ? C22 C21 C27 O22 16.70(18) . . . . ? C26 C21 C27 O22 -163.03(12) . . . . ? C22 C21 C27 O21 -163.63(11) . . . . ? C26 C21 C27 O21 16.63(18) . . . . ? C26 C21 C22 C23 -0.61(18) . . . . ? C27 C21 C22 C23 179.64(11) . . . . ? C21 C22 C23 C24 1.38(19) . . . . ? C22 C23 C24 C25 -0.7(2) . . . . ? C22 C23 C24 Cl1 177.98(10) . . . . ? C23 C24 C25 C26 -0.69(19) . . . . ? Cl1 C24 C25 C26 -179.39(9) . . . . ? C24 C25 C26 C21 1.48(18) . . . . ? C22 C21 C26 C25 -0.84(18) . . . . ? C27 C21 C26 C25 178.89(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 O21 0.94(2) 1.78(2) 2.7253(15) 174.9(18) . N12 H12A O22 0.92(2) 1.85(2) 2.7631(16) 179(2) . N12 H12B O21 0.89(2) 1.95(2) 2.8381(15) 176.0(18) 2_464 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.292 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.050 #END data_ar0816m(A15) _database_code_depnum_ccdc_archive 'CCDC 772245' #TrackingRef '- allcifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; AR-1g-15 2-aminopyridine, HOOC-(CH2)8-COOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C5 H6 N2)2 (C10 H18 O4) ; _chemical_formula_sum 'C20 H30 N4 O4' _chemical_formula_weight 390.48 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.2382(6) _cell_length_b 7.3603(5) _cell_length_c 17.7902(11) _cell_angle_alpha 90.00 _cell_angle_beta 102.979(3) _cell_angle_gamma 90.00 _cell_volume 1051.16(12) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6851 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 31.65 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12489 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 31.51 _reflns_number_total 3494 _reflns_number_gt 2982 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.2000P] 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 3494 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1159 _refine_ls_wR_factor_gt 0.1100 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 N11 N 0.51614(9) -0.07936(9) 0.15436(4) 0.01800(15) Uani 1 1 d . . . H11 H 0.4781(14) 0.0339(16) 0.1236(6) 0.022 Uiso 1 1 d . . . C12 C 0.47027(10) -0.11222(11) 0.22143(4) 0.01764(16) Uani 1 1 d . . . N12 N 0.38003(10) 0.01187(11) 0.24821(4) 0.02457(17) Uani 1 1 d . . . H12A H 0.3459(16) 0.1148(18) 0.2202(7) 0.029 Uiso 1 1 d . . . H12B H 0.3319(16) -0.0220(17) 0.2867(7) 0.029 Uiso 1 1 d . . . C13 C 0.52001(11) -0.27795(12) 0.26048(5) 0.02085(17) Uani 1 1 d . . . H13 H 0.4902 -0.3039 0.3079 0.025 Uiso 1 1 calc R . . C14 C 0.61116(11) -0.39994(13) 0.22934(5) 0.02457(18) Uani 1 1 d . . . H14 H 0.6438 -0.5116 0.2551 0.029 Uiso 1 1 calc R . . C15 C 0.65714(12) -0.36194(13) 0.15945(5) 0.02585(19) Uani 1 1 d . . . H15 H 0.7218 -0.4457 0.1379 0.031 Uiso 1 1 calc R . . C16 C 0.60623(11) -0.20117(12) 0.12352(5) 0.02190(17) Uani 1 1 d . . . H16 H 0.6346 -0.1741 0.0758 0.026 Uiso 1 1 calc R . . C21 C 0.33195(10) 0.32043(11) 0.08966(4) 0.01750(16) Uani 1 1 d . . . O21 O 0.42415(9) 0.20129(9) 0.06861(4) 0.02556(16) Uani 1 1 d . . . O22 O 0.28338(9) 0.31475(8) 0.15118(3) 0.02385(15) Uani 1 1 d . . . C22 C 0.27704(10) 0.47603(11) 0.03385(4) 0.01772(15) Uani 1 1 d . . . H22A H 0.2064 0.4261 -0.0142 0.021 Uiso 1 1 calc R . . H22B H 0.3772 0.5294 0.0204 0.021 Uiso 1 1 calc R . . C23 C 0.18138(10) 0.62718(10) 0.06281(4) 0.01736(15) Uani 1 1 d . . . H23A H 0.2516 0.6797 0.1104 0.021 Uiso 1 1 calc R . . H23B H 0.0804 0.5756 0.0761 0.021 Uiso 1 1 calc R . . C24 C 0.13022(11) 0.77744(11) 0.00329(5) 0.01939(16) Uani 1 1 d . . . H24A H 0.2315 0.8300 -0.0093 0.023 Uiso 1 1 calc R . . H24B H 0.0619 0.7241 -0.0446 0.023 Uiso 1 1 calc R . . C25 C 0.03165(11) 0.92866(11) 0.03081(5) 0.02013(16) Uani 1 1 d . . . H25A H 0.1033 0.9886 0.0762 0.024 Uiso 1 1 calc R . . H25B H -0.0646 0.8748 0.0475 0.024 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 N11 0.0191(3) 0.0197(3) 0.0160(3) 0.0017(2) 0.0055(2) 0.0010(2) C12 0.0183(3) 0.0190(3) 0.0161(3) 0.0006(3) 0.0050(3) -0.0008(3) N12 0.0336(4) 0.0214(3) 0.0232(3) 0.0042(3) 0.0159(3) 0.0055(3) C13 0.0236(4) 0.0225(4) 0.0166(3) 0.0041(3) 0.0048(3) 0.0016(3) C14 0.0274(4) 0.0236(4) 0.0220(4) 0.0051(3) 0.0041(3) 0.0065(3) C15 0.0286(4) 0.0273(4) 0.0228(4) 0.0021(3) 0.0081(3) 0.0099(4) C16 0.0226(4) 0.0263(4) 0.0182(3) 0.0009(3) 0.0077(3) 0.0039(3) C21 0.0193(3) 0.0156(3) 0.0185(3) 0.0004(2) 0.0062(3) 0.0013(3) O21 0.0349(4) 0.0225(3) 0.0235(3) 0.0057(2) 0.0155(3) 0.0125(3) O22 0.0344(4) 0.0199(3) 0.0213(3) 0.0032(2) 0.0146(3) 0.0068(2) C22 0.0205(4) 0.0165(3) 0.0172(3) 0.0017(3) 0.0064(3) 0.0029(3) C23 0.0195(3) 0.0150(3) 0.0183(3) 0.0005(2) 0.0056(3) 0.0014(3) C24 0.0235(4) 0.0149(3) 0.0206(4) 0.0015(3) 0.0069(3) 0.0021(3) C25 0.0249(4) 0.0140(3) 0.0221(4) 0.0012(3) 0.0068(3) 0.0019(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C12 1.3519(10) . ? N11 C16 1.3560(11) . ? N11 H11 1.007(12) . ? C12 N12 1.3315(11) . ? C12 C13 1.4179(11) . ? N12 H12A 0.915(13) . ? N12 H12B 0.901(13) . ? C13 C14 1.3653(12) . ? C13 H13 0.9500 . ? C14 C15 1.4068(13) . ? C14 H14 0.9500 . ? C15 C16 1.3654(12) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 O22 1.2474(10) . ? C21 O21 1.2704(10) . ? C21 C22 1.5168(11) . ? C22 C23 1.5187(11) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.5236(11) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.5220(11) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C25 1.5230(16) 3_575 ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N11 C16 121.71(7) . . ? C12 N11 H11 120.8(6) . . ? C16 N11 H11 117.3(6) . . ? N12 C12 N11 118.83(7) . . ? N12 C12 C13 122.54(7) . . ? N11 C12 C13 118.63(7) . . ? C12 N12 H12A 120.1(8) . . ? C12 N12 H12B 117.3(8) . . ? H12A N12 H12B 120.6(11) . . ? C14 C13 C12 119.45(7) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C15 120.64(8) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 118.08(8) . . ? C16 C15 H15 121.0 . . ? C14 C15 H15 121.0 . . ? N11 C16 C15 121.47(8) . . ? N11 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? O22 C21 O21 124.49(7) . . ? O22 C21 C22 119.50(7) . . ? O21 C21 C22 115.99(7) . . ? C21 C22 C23 115.61(6) . . ? C21 C22 H22A 108.4 . . ? C23 C22 H22A 108.4 . . ? C21 C22 H22B 108.4 . . ? C23 C22 H22B 108.4 . . ? H22A C22 H22B 107.4 . . ? C22 C23 C24 112.31(6) . . ? C22 C23 H23A 109.1 . . ? C24 C23 H23A 109.1 . . ? C22 C23 H23B 109.1 . . ? C24 C23 H23B 109.1 . . ? H23A C23 H23B 107.9 . . ? C25 C24 C23 113.05(7) . . ? C25 C24 H24A 109.0 . . ? C23 C24 H24A 109.0 . . ? C25 C24 H24B 109.0 . . ? C23 C24 H24B 109.0 . . ? H24A C24 H24B 107.8 . . ? C24 C25 C25 113.20(8) . 3_575 ? C24 C25 H25A 108.9 . . ? C25 C25 H25A 108.9 3_575 . ? C24 C25 H25B 108.9 . . ? C25 C25 H25B 108.9 3_575 . ? H25A C25 H25B 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 N12 -179.15(8) . . . . ? C16 N11 C12 C13 0.73(12) . . . . ? N12 C12 C13 C14 179.37(8) . . . . ? N11 C12 C13 C14 -0.51(12) . . . . ? C12 C13 C14 C15 0.56(14) . . . . ? C13 C14 C15 C16 -0.80(14) . . . . ? C12 N11 C16 C15 -1.02(13) . . . . ? C14 C15 C16 N11 1.02(14) . . . . ? O22 C21 C22 C23 7.04(11) . . . . ? O21 C21 C22 C23 -174.17(7) . . . . ? C21 C22 C23 C24 -179.74(7) . . . . ? C22 C23 C24 C25 179.04(7) . . . . ? C23 C24 C25 C25 -175.37(8) . . . 3_575 ? 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 N11 H11 O21 1.007(12) 1.574(12) 2.5786(9) 174.3(10) . N12 H12A O22 0.915(13) 1.912(14) 2.8224(10) 172.7(12) . N12 H12B O22 0.901(13) 2.009(13) 2.8641(10) 158.0(11) 2_545 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 31.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.430 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.047 #END data_ar0709m(B1) _database_code_depnum_ccdc_archive 'CCDC 772246' #TrackingRef '- allcifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; AR-cc-1a-1 2-amino-5-bromopyridine, 4-NC-PhCOOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C5 H5 N2 Br) (C8 H5 N O2) ; _chemical_formula_sum 'C13 H10 Br N3 O2' _chemical_formula_weight 320.15 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 12.3903(8) _cell_length_b 5.6871(3) _cell_length_c 18.0290(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1270.41(13) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9874 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 32.34 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 3.237 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4984 _exptl_absorpt_correction_T_max 0.7379 _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22901 _diffrn_reflns_av_R_equivalents 0.0752 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 33.17 _reflns_number_total 4830 _reflns_number_gt 4113 _reflns_threshold_expression >2sigma(I) _reflns_Friedel_coverage 0.944 _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.006(7) _refine_ls_number_reflns 4830 _refine_ls_number_parameters 181 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0756 _refine_ls_wR_factor_gt 0.0735 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _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 Br1 Br 0.271620(13) 1.14065(3) 0.830808(16) 0.02243(6) Uani 1 1 d . . . N11 N 0.17877(16) 0.5996(4) 0.69488(12) 0.0173(4) Uani 1 1 d . . . H11 H 0.2130(19) 0.497(5) 0.6705(15) 0.021 Uiso 1 1 d . . . C12 C 0.07213(16) 0.6331(3) 0.68198(13) 0.0167(4) Uani 1 1 d . . . N12 N 0.02009(13) 0.4839(3) 0.63764(11) 0.0219(4) Uani 1 1 d . . . H12A H 0.049(3) 0.385(4) 0.6239(17) 0.026 Uiso 1 1 d . . . H12B H -0.052(2) 0.503(5) 0.6278(14) 0.026 Uiso 1 1 d . . . C13 C 0.02128(17) 0.8256(4) 0.71664(13) 0.0197(4) Uani 1 1 d . . . H13A H -0.0536 0.8520 0.7089 0.024 Uiso 1 1 calc R . . C14 C 0.07799(15) 0.9736(4) 0.76099(11) 0.0199(4) Uani 1 1 d . . . H14A H 0.0433 1.1035 0.7840 0.024 Uiso 1 1 calc R . . C15 C 0.18883(16) 0.9324(4) 0.77258(10) 0.0177(3) Uani 1 1 d . . . C16 C 0.23691(15) 0.7439(4) 0.73962(12) 0.0180(4) Uani 1 1 d . . . H16A H 0.3113 0.7134 0.7480 0.022 Uiso 1 1 calc R . . C21 C 0.31705(15) -0.0168(3) 0.53787(10) 0.0155(3) Uani 1 1 d . . . C27 C 0.2517(3) 0.1439(3) 0.58823(17) 0.0156(4) Uani 1 1 d . . . O21 O 0.30350(11) 0.3040(3) 0.62286(8) 0.0197(3) Uani 1 1 d . . . O22 O 0.15347(12) 0.1109(3) 0.59107(9) 0.0246(3) Uani 1 1 d . . . C22 C 0.26970(16) -0.2209(4) 0.50985(12) 0.0210(4) Uani 1 1 d . . . H22A H 0.1975 -0.2587 0.5230 0.025 Uiso 1 1 calc R . . C23 C 0.3267(2) -0.3692(4) 0.46309(17) 0.0234(6) Uani 1 1 d . . . H23A H 0.2944 -0.5087 0.4445 0.028 Uiso 1 1 calc R . . C24 C 0.43270(17) -0.3102(4) 0.44359(12) 0.0182(4) Uani 1 1 d . . . C25 C 0.48054(18) -0.1063(4) 0.46989(12) 0.0212(4) Uani 1 1 d . . . H25A H 0.5518 -0.0656 0.4553 0.025 Uiso 1 1 calc R . . C26 C 0.42295(15) 0.0383(4) 0.51801(12) 0.0209(4) Uani 1 1 d . . . H26A H 0.4560 0.1757 0.5375 0.025 Uiso 1 1 calc R . . C28 C 0.49396(18) -0.4637(3) 0.39559(12) 0.0222(4) Uani 1 1 d . . . N28 N 0.54524(17) -0.5815(3) 0.35774(12) 0.0309(4) 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 0.02009(9) 0.02235(9) 0.02486(9) -0.00581(10) -0.00206(12) -0.00136(6) N11 0.0118(9) 0.0184(9) 0.0218(10) -0.0027(7) -0.0013(7) 0.0041(7) C12 0.0125(8) 0.0173(9) 0.0203(9) 0.0018(7) 0.0019(7) -0.0003(7) N12 0.0140(8) 0.0215(9) 0.0301(10) -0.0051(7) -0.0031(7) 0.0036(6) C13 0.0122(8) 0.0210(9) 0.0259(11) 0.0002(8) 0.0009(8) 0.0034(7) C14 0.0149(8) 0.0189(9) 0.0259(9) -0.0034(7) 0.0020(8) 0.0024(7) C15 0.0163(8) 0.0191(9) 0.0176(9) -0.0030(7) 0.0008(7) -0.0002(7) C16 0.0131(8) 0.0191(10) 0.0218(9) -0.0015(7) -0.0014(7) 0.0013(7) C21 0.0137(8) 0.0154(8) 0.0176(8) 0.0002(7) -0.0020(7) 0.0026(6) C27 0.0153(7) 0.0189(8) 0.0126(12) -0.0008(7) -0.0005(8) 0.0034(8) O21 0.0130(6) 0.0194(6) 0.0266(7) -0.0068(6) -0.0016(6) 0.0022(5) O22 0.0125(6) 0.0272(8) 0.0343(9) -0.0089(6) 0.0016(6) -0.0006(5) C22 0.0173(9) 0.0197(9) 0.0258(10) -0.0039(8) 0.0019(8) -0.0018(7) C23 0.0237(14) 0.0180(10) 0.0285(13) -0.0033(8) 0.0054(10) -0.0035(8) C24 0.0194(9) 0.0173(9) 0.0180(9) 0.0001(7) 0.0012(7) 0.0015(7) C25 0.0161(9) 0.0208(10) 0.0267(12) -0.0040(8) 0.0022(8) 0.0003(7) C26 0.0142(9) 0.0215(10) 0.0271(10) -0.0067(8) 0.0003(8) -0.0014(7) C28 0.0243(9) 0.0173(9) 0.0250(10) -0.0023(7) 0.0034(8) -0.0011(8) N28 0.0311(9) 0.0221(8) 0.0394(11) -0.0075(8) 0.0126(9) -0.0033(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 C15 1.886(2) . ? N11 C12 1.355(3) . ? N11 C16 1.358(3) . ? N11 H11 0.85(3) . ? C12 N12 1.332(3) . ? C12 C13 1.409(3) . ? N12 H12A 0.71(3) . ? N12 H12B 0.91(2) . ? C13 C14 1.357(3) . ? C13 H13A 0.9500 . ? C14 C15 1.409(3) . ? C14 H14A 0.9500 . ? C15 C16 1.363(3) . ? C16 H16A 0.9500 . ? C21 C22 1.396(3) . ? C21 C26 1.396(3) . ? C21 C27 1.522(4) . ? C27 O22 1.232(4) . ? C27 O21 1.277(3) . ? C22 C23 1.386(3) . ? C22 H22A 0.9500 . ? C23 C24 1.400(4) . ? C23 H23A 0.9500 . ? C24 C25 1.386(3) . ? C24 C28 1.445(3) . ? C25 C26 1.392(3) . ? C25 H25A 0.9500 . ? C26 H26A 0.9500 . ? C28 N28 1.148(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 C12 N11 C16 122.3(2) . . ? C12 N11 H11 119.8(16) . . ? C16 N11 H11 117.4(16) . . ? N12 C12 N11 119.0(2) . . ? N12 C12 C13 122.99(18) . . ? N11 C12 C13 118.0(2) . . ? C12 N12 H12A 118(2) . . ? C12 N12 H12B 120.9(17) . . ? H12A N12 H12B 121(3) . . ? C14 C13 C12 120.77(19) . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C13 C14 C15 119.29(19) . . ? C13 C14 H14A 120.4 . . ? C15 C14 H14A 120.4 . . ? C16 C15 C14 119.48(18) . . ? C16 C15 Br1 119.93(15) . . ? C14 C15 Br1 120.57(15) . . ? N11 C16 C15 120.18(18) . . ? N11 C16 H16A 119.9 . . ? C15 C16 H16A 119.9 . . ? C22 C21 C26 119.28(17) . . ? C22 C21 C27 119.5(2) . . ? C26 C21 C27 121.25(19) . . ? O22 C27 O21 125.8(3) . . ? O22 C27 C21 117.3(2) . . ? O21 C27 C21 116.9(3) . . ? C23 C22 C21 120.80(19) . . ? C23 C22 H22A 119.6 . . ? C21 C22 H22A 119.6 . . ? C22 C23 C24 119.0(2) . . ? C22 C23 H23A 120.5 . . ? C24 C23 H23A 120.5 . . ? C25 C24 C23 121.0(2) . . ? C25 C24 C28 119.07(19) . . ? C23 C24 C28 119.9(2) . . ? C24 C25 C26 119.2(2) . . ? C24 C25 H25A 120.4 . . ? C26 C25 H25A 120.4 . . ? C25 C26 C21 120.61(18) . . ? C25 C26 H26A 119.7 . . ? C21 C26 H26A 119.7 . . ? N28 C28 C24 178.0(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 C16 N11 C12 N12 -179.8(2) . . . . ? C16 N11 C12 C13 0.1(3) . . . . ? N12 C12 C13 C14 -179.6(2) . . . . ? N11 C12 C13 C14 0.6(3) . . . . ? C12 C13 C14 C15 -0.4(3) . . . . ? C13 C14 C15 C16 -0.5(3) . . . . ? C13 C14 C15 Br1 177.62(16) . . . . ? C12 N11 C16 C15 -1.0(3) . . . . ? C14 C15 C16 N11 1.2(3) . . . . ? Br1 C15 C16 N11 -176.96(16) . . . . ? C22 C21 C27 O22 -13.4(3) . . . . ? C26 C21 C27 O22 165.4(2) . . . . ? C22 C21 C27 O21 167.8(2) . . . . ? C26 C21 C27 O21 -13.4(3) . . . . ? C26 C21 C22 C23 0.3(3) . . . . ? C27 C21 C22 C23 179.2(2) . . . . ? C21 C22 C23 C24 -0.6(4) . . . . ? C22 C23 C24 C25 -0.4(4) . . . . ? C22 C23 C24 C28 179.3(2) . . . . ? C23 C24 C25 C26 1.7(3) . . . . ? C28 C24 C25 C26 -178.0(2) . . . . ? C24 C25 C26 C21 -2.0(3) . . . . ? C22 C21 C26 C25 1.0(3) . . . . ? C27 C21 C26 C25 -177.8(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 N11 H11 O21 0.85(3) 1.79(3) 2.627(3) 171(2) . N12 H12A O22 0.71(3) 2.11(3) 2.817(2) 172(3) . N12 H12B O21 0.91(2) 2.10(3) 2.954(2) 154(2) 3_465 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 33.17 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.329 _refine_diff_density_min -0.641 _refine_diff_density_rms 0.093 #end data_ar0719m(B5) _database_code_depnum_ccdc_archive 'CCDC 772247' #TrackingRef '- allcifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ARcc-1a-aa5 2-amino-5-bromopyridine, 4-nitrobenzoic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C5 H5 N2 Br) (C7 H5 N O4) ; _chemical_formula_sum 'C12 H10 Br N3 O4' _chemical_formula_weight 340.14 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' 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.9727(5) _cell_length_b 6.2956(4) _cell_length_c 24.6286(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.580(4) _cell_angle_gamma 90.00 _cell_volume 1236.12(13) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8265 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 33.12 _exptl_crystal_description prism _exptl_crystal_colour yellow _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 1.828 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 3.344 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5544 _exptl_absorpt_correction_T_max 0.6339 _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18835 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 32.58 _reflns_number_total 4299 _reflns_number_gt 3691 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^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 4299 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1281 _refine_ls_wR_factor_gt 0.1243 _refine_ls_goodness_of_fit_ref 1.198 _refine_ls_restrained_S_all 1.198 _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 0.70193(3) 0.34661(4) 0.032679(9) 0.01799(9) Uani 1 1 d . . . N11 N 0.4561(3) 0.1451(3) 0.16862(8) 0.0136(4) Uani 1 1 d . . . H11 H 0.405(4) 0.232(6) 0.1995(13) 0.016 Uiso 1 1 d . . . C12 C 0.4159(3) -0.0605(3) 0.16000(9) 0.0131(4) Uani 1 1 d . . . N12 N 0.3309(3) -0.1613(3) 0.19894(9) 0.0165(4) Uani 1 1 d . . . H12A H 0.322(5) -0.112(6) 0.2304(15) 0.020 Uiso 1 1 d . . . H12B H 0.311(5) -0.308(6) 0.1982(15) 0.020 Uiso 1 1 d . . . C13 C 0.4628(3) -0.1544(4) 0.11027(10) 0.0150(4) Uani 1 1 d . . . H13 H 0.4342 -0.2981 0.1028 0.018 Uiso 1 1 calc R . . C14 C 0.5499(3) -0.0377(4) 0.07273(9) 0.0140(4) Uani 1 1 d . . . H14 H 0.5824 -0.1004 0.0394 0.017 Uiso 1 1 calc R . . C15 C 0.5907(3) 0.1758(4) 0.08414(10) 0.0133(4) Uani 1 1 d . . . C16 C 0.5434(3) 0.2626(4) 0.13217(9) 0.0136(4) Uani 1 1 d . . . H16 H 0.5714 0.4059 0.1403 0.016 Uiso 1 1 calc R . . C21 C 0.1349(3) 0.4069(4) 0.31893(9) 0.0132(4) Uani 1 1 d . . . C27 C 0.2445(3) 0.2827(4) 0.28042(9) 0.0134(4) Uani 1 1 d . . . O21 O 0.3002(3) 0.3808(3) 0.23944(7) 0.0158(3) Uani 1 1 d . . . O22 O 0.2740(3) 0.0924(3) 0.29178(7) 0.0199(4) Uani 1 1 d . . . C22 C 0.0883(3) 0.3177(4) 0.36841(10) 0.0142(4) Uani 1 1 d . . . H22 H 0.1213 0.1765 0.3770 0.017 Uiso 1 1 calc R . . C23 C -0.0057(3) 0.4332(4) 0.40522(9) 0.0152(4) Uani 1 1 d . . . H23 H -0.0376 0.3732 0.4390 0.018 Uiso 1 1 calc R . . C24 C -0.0519(3) 0.6394(4) 0.39128(10) 0.0144(4) Uani 1 1 d . . . N24 N -0.1462(3) 0.7663(4) 0.43060(9) 0.0178(4) Uani 1 1 d . . . O23 O -0.1772(3) 0.6881(4) 0.47494(9) 0.0279(5) Uani 1 1 d . . . O24 O -0.1891(3) 0.9476(3) 0.41723(9) 0.0283(5) Uani 1 1 d . . . C25 C -0.0098(3) 0.7316(4) 0.34213(10) 0.0147(4) Uani 1 1 d . . . H25 H -0.0439 0.8724 0.3336 0.018 Uiso 1 1 calc R . . C26 C 0.0834(3) 0.6127(4) 0.30578(10) 0.0141(4) Uani 1 1 d . . . H26 H 0.1124 0.6719 0.2717 0.017 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02076(16) 0.01496(13) 0.01832(13) 0.00439(8) 0.00290(9) -0.00215(9) N11 0.0176(10) 0.0076(8) 0.0155(8) -0.0003(6) 0.0017(7) 0.0002(7) C12 0.0130(11) 0.0074(9) 0.0187(9) 0.0000(7) -0.0004(8) 0.0014(8) N12 0.0203(11) 0.0085(8) 0.0207(9) 0.0005(7) 0.0045(8) 0.0000(8) C13 0.0175(12) 0.0081(9) 0.0195(10) -0.0020(7) 0.0005(8) -0.0002(8) C14 0.0132(11) 0.0120(9) 0.0167(9) -0.0016(7) 0.0003(8) 0.0006(8) C15 0.0131(11) 0.0096(9) 0.0173(9) 0.0028(7) 0.0005(8) -0.0013(8) C16 0.0155(12) 0.0081(9) 0.0172(9) 0.0006(7) 0.0000(8) -0.0014(8) C21 0.0153(11) 0.0092(9) 0.0151(9) -0.0002(7) 0.0001(8) -0.0006(8) C27 0.0143(11) 0.0097(8) 0.0161(9) -0.0021(7) 0.0003(8) 0.0013(8) O21 0.0200(9) 0.0091(7) 0.0184(8) -0.0006(6) 0.0041(7) 0.0006(6) O22 0.0303(11) 0.0086(7) 0.0207(8) 0.0012(6) 0.0045(7) 0.0054(7) C22 0.0157(12) 0.0099(9) 0.0170(9) 0.0012(7) 0.0011(8) 0.0011(8) C23 0.0173(12) 0.0126(10) 0.0158(9) 0.0004(8) 0.0019(8) 0.0000(9) C24 0.0154(12) 0.0108(9) 0.0170(10) -0.0034(7) 0.0019(8) 0.0008(8) N24 0.0152(11) 0.0150(9) 0.0233(10) -0.0044(8) 0.0028(8) -0.0003(8) O23 0.0343(13) 0.0273(11) 0.0223(9) -0.0011(8) 0.0117(8) 0.0062(9) O24 0.0323(12) 0.0157(9) 0.0371(11) -0.0023(8) 0.0113(9) 0.0089(8) C25 0.0154(12) 0.0087(9) 0.0200(10) 0.0003(8) 0.0014(8) 0.0011(8) C26 0.0153(11) 0.0099(9) 0.0171(9) 0.0008(7) 0.0014(8) -0.0009(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 C15 1.890(2) . ? N11 C12 1.350(3) . ? N11 C16 1.360(3) . ? N11 H11 1.03(3) . ? C12 N12 1.339(3) . ? C12 C13 1.414(3) . ? N12 H12A 0.84(4) . ? N12 H12B 0.94(4) . ? C13 C14 1.375(3) . ? C13 H13 0.9500 . ? C14 C15 1.411(3) . ? C14 H14 0.9500 . ? C15 C16 1.360(3) . ? C16 H16 0.9500 . ? C21 C22 1.396(3) . ? C21 C26 1.396(3) . ? C21 C27 1.514(3) . ? C27 O22 1.252(3) . ? C27 O21 1.267(3) . ? C22 C23 1.388(3) . ? C22 H22 0.9500 . ? C23 C24 1.391(3) . ? C23 H23 0.9500 . ? C24 C25 1.387(3) . ? C24 N24 1.469(3) . ? N24 O23 1.225(3) . ? N24 O24 1.235(3) . ? C25 C26 1.389(3) . ? C25 H25 0.9500 . ? C26 H26 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 C12 N11 C16 122.7(2) . . ? C12 N11 H11 122(2) . . ? C16 N11 H11 114(2) . . ? N12 C12 N11 117.6(2) . . ? N12 C12 C13 124.2(2) . . ? N11 C12 C13 118.2(2) . . ? C12 N12 H12A 123(3) . . ? C12 N12 H12B 123(2) . . ? H12A N12 H12B 111(3) . . ? C14 C13 C12 119.9(2) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 119.5(2) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 119.4(2) . . ? C16 C15 Br1 119.41(17) . . ? C14 C15 Br1 121.15(18) . . ? C15 C16 N11 120.3(2) . . ? C15 C16 H16 119.9 . . ? N11 C16 H16 119.9 . . ? C22 C21 C26 119.7(2) . . ? C22 C21 C27 119.9(2) . . ? C26 C21 C27 120.3(2) . . ? O22 C27 O21 125.3(2) . . ? O22 C27 C21 117.6(2) . . ? O21 C27 C21 117.1(2) . . ? C23 C22 C21 120.6(2) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 118.1(2) . . ? C22 C23 H23 121.0 . . ? C24 C23 H23 121.0 . . ? C25 C24 C23 122.7(2) . . ? C25 C24 N24 118.5(2) . . ? C23 C24 N24 118.7(2) . . ? O23 N24 O24 123.4(2) . . ? O23 N24 C24 118.6(2) . . ? O24 N24 C24 118.0(2) . . ? C24 C25 C26 118.2(2) . . ? C24 C25 H25 120.9 . . ? C26 C25 H25 120.9 . . ? C25 C26 C21 120.6(2) . . ? C25 C26 H26 119.7 . . ? C21 C26 H26 119.7 . . ? 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 179.4(2) . . . . ? C16 N11 C12 C13 -1.8(4) . . . . ? N12 C12 C13 C14 179.9(2) . . . . ? N11 C12 C13 C14 1.2(4) . . . . ? C12 C13 C14 C15 -0.4(4) . . . . ? C13 C14 C15 C16 0.1(4) . . . . ? C13 C14 C15 Br1 -177.3(2) . . . . ? C14 C15 C16 N11 -0.6(4) . . . . ? Br1 C15 C16 N11 176.82(19) . . . . ? C12 N11 C16 C15 1.5(4) . . . . ? C22 C21 C27 O22 8.1(4) . . . . ? C26 C21 C27 O22 -173.5(2) . . . . ? C22 C21 C27 O21 -171.3(2) . . . . ? C26 C21 C27 O21 7.1(4) . . . . ? C26 C21 C22 C23 -1.4(4) . . . . ? C27 C21 C22 C23 177.1(2) . . . . ? C21 C22 C23 C24 0.1(4) . . . . ? C22 C23 C24 C25 0.9(4) . . . . ? C22 C23 C24 N24 -177.8(2) . . . . ? C25 C24 N24 O23 -177.0(3) . . . . ? C23 C24 N24 O23 1.9(4) . . . . ? C25 C24 N24 O24 2.5(4) . . . . ? C23 C24 N24 O24 -178.6(2) . . . . ? C23 C24 C25 C26 -0.6(4) . . . . ? N24 C24 C25 C26 178.2(2) . . . . ? C24 C25 C26 C21 -0.8(4) . . . . ? C22 C21 C26 C25 1.8(4) . . . . ? C27 C21 C26 C25 -176.7(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 N11 H11 O21 1.03(3) 1.60(4) 2.614(3) 170(3) . N12 H12A O22 0.84(4) 2.03(4) 2.829(3) 161(4) . N12 H12B O21 0.94(4) 2.21(4) 3.061(3) 151(3) 1_545 _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 32.58 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 1.785 _refine_diff_density_min -1.655 _refine_diff_density_rms 0.164 #end data_ar0801m(D6) _database_code_depnum_ccdc_archive 'CCDC 772248' #TrackingRef '- allcifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ARcc-1c-aa6 N-(5-bromo-2-pyridyl)propionamide, 3,4-Cl2-PhCOOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C8 H9 N2 O BR) (C7 H4 O2 Cl2) ; _chemical_formula_sum 'C15 H13 Br Cl2 N2 O3' _chemical_formula_weight 420.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.9019(2) _cell_length_b 12.5454(8) _cell_length_c 16.9260(10) _cell_angle_alpha 73.128(3) _cell_angle_beta 86.428(3) _cell_angle_gamma 85.881(3) _cell_volume 790.08(8) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9930 _cell_measurement_theta_min 3.26 _cell_measurement_theta_max 31.49 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.766 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 2.955 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5254 _exptl_absorpt_correction_T_max 0.8663 _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16452 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 30.51 _reflns_number_total 4701 _reflns_number_gt 4244 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.2000P] 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 4701 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0295 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0674 _refine_ls_wR_factor_gt 0.0652 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 Br1 Br 0.19124(4) 0.875203(11) 0.079408(8) 0.02013(5) Uani 1 1 d . . . Cl1 Cl -0.37445(10) -0.00186(3) 0.60965(2) 0.02179(8) Uani 1 1 d . . . Cl2 Cl -0.64310(9) 0.15548(3) 0.71893(2) 0.01967(8) Uani 1 1 d . . . N11 N 0.3329(3) 0.54554(10) 0.21372(7) 0.0157(2) Uani 1 1 d . . . C12 C 0.5257(3) 0.49928(11) 0.16214(8) 0.0140(2) Uani 1 1 d . . . N12 N 0.6037(3) 0.38542(10) 0.19503(7) 0.0159(2) Uani 1 1 d . . . H12 H 0.508(5) 0.3565(16) 0.2409(12) 0.019 Uiso 1 1 d . . . C13 C 0.6326(4) 0.56282(12) 0.08289(8) 0.0165(3) Uani 1 1 d . . . H13 H 0.7683 0.5290 0.0472 0.020 Uiso 1 1 calc R . . C14 C 0.5372(4) 0.67553(12) 0.05760(8) 0.0168(3) Uani 1 1 d . . . H14 H 0.6075 0.7204 0.0043 0.020 Uiso 1 1 calc R . . C15 C 0.3369(4) 0.72240(11) 0.11132(8) 0.0155(2) Uani 1 1 d . . . C16 C 0.2401(4) 0.65486(12) 0.18856(8) 0.0162(3) Uani 1 1 d . . . H16 H 0.1031 0.6869 0.2251 0.019 Uiso 1 1 calc R . . C17 C 0.8007(4) 0.31564(12) 0.15824(8) 0.0153(2) Uani 1 1 d . . . O17 O 0.9483(3) 0.34788(9) 0.09077(7) 0.0248(2) Uani 1 1 d . . . C18 C 0.8249(4) 0.19521(12) 0.21117(8) 0.0166(3) Uani 1 1 d . . . H18A H 0.5917 0.1723 0.2328 0.020 Uiso 1 1 calc R . . H18B H 0.9664 0.1893 0.2590 0.020 Uiso 1 1 calc R . . C19 C 0.9823(4) 0.11584(13) 0.16372(10) 0.0213(3) Uani 1 1 d . . . H19A H 0.9926 0.0394 0.2006 0.032 Uiso 1 1 calc R . . H19B H 1.2151 0.1372 0.1431 0.032 Uiso 1 1 calc R . . H19C H 0.8403 0.1199 0.1171 0.032 Uiso 1 1 calc R . . C21 C -0.1216(3) 0.29998(11) 0.46891(8) 0.0138(2) Uani 1 1 d . . . C22 C -0.1577(4) 0.18508(11) 0.49832(8) 0.0147(2) Uani 1 1 d . . . H22 H -0.0692 0.1377 0.4662 0.018 Uiso 1 1 calc R . . C23 C -0.3235(3) 0.14030(11) 0.57470(8) 0.0142(2) Uani 1 1 d . . . C24 C -0.4484(3) 0.21035(12) 0.62235(8) 0.0147(2) Uani 1 1 d . . . C25 C -0.4143(4) 0.32488(12) 0.59285(8) 0.0162(3) Uani 1 1 d . . . H25 H -0.5010 0.3723 0.6251 0.019 Uiso 1 1 calc R . . C26 C -0.2528(4) 0.36967(11) 0.51600(8) 0.0153(2) Uani 1 1 d . . . H26 H -0.2316 0.4480 0.4954 0.018 Uiso 1 1 calc R . . C27 C 0.0632(4) 0.34613(11) 0.38731(8) 0.0148(2) Uani 1 1 d . . . O21 O 0.0422(3) 0.45605(9) 0.36010(7) 0.0228(2) Uani 1 1 d . . . H21 H 0.149(5) 0.4782(17) 0.3102(14) 0.027 Uiso 1 1 d . . . O22 O 0.2200(3) 0.28613(9) 0.34995(6) 0.0190(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02470(8) 0.01460(8) 0.01796(8) -0.00126(5) 0.00146(5) 0.00310(5) Cl1 0.03057(19) 0.01324(15) 0.01882(16) -0.00171(12) 0.00762(13) -0.00279(13) Cl2 0.02330(17) 0.02140(17) 0.01182(14) -0.00222(12) 0.00656(12) -0.00188(13) N11 0.0181(5) 0.0159(5) 0.0117(5) -0.0028(4) 0.0038(4) 0.0000(4) C12 0.0151(6) 0.0150(6) 0.0112(6) -0.0033(5) 0.0018(5) -0.0006(5) N12 0.0203(6) 0.0137(5) 0.0110(5) -0.0011(4) 0.0058(4) 0.0008(4) C13 0.0194(6) 0.0168(6) 0.0124(6) -0.0038(5) 0.0050(5) -0.0007(5) C14 0.0189(6) 0.0185(6) 0.0108(6) -0.0013(5) 0.0035(5) -0.0018(5) C15 0.0176(6) 0.0134(6) 0.0142(6) -0.0025(5) 0.0008(5) 0.0000(5) C16 0.0183(6) 0.0162(6) 0.0134(6) -0.0041(5) 0.0039(5) 0.0004(5) C17 0.0155(6) 0.0164(6) 0.0141(6) -0.0052(5) 0.0023(5) -0.0008(5) O17 0.0327(6) 0.0199(5) 0.0172(5) -0.0019(4) 0.0128(4) 0.0025(4) C18 0.0189(6) 0.0154(6) 0.0140(6) -0.0032(5) 0.0036(5) 0.0000(5) C19 0.0239(7) 0.0183(7) 0.0219(7) -0.0076(5) 0.0034(6) 0.0010(5) C21 0.0148(6) 0.0149(6) 0.0109(5) -0.0026(5) 0.0016(4) -0.0011(5) C22 0.0172(6) 0.0143(6) 0.0121(6) -0.0039(5) 0.0026(5) 0.0000(5) C23 0.0160(6) 0.0125(6) 0.0126(6) -0.0015(4) 0.0014(5) -0.0010(5) C24 0.0146(6) 0.0181(6) 0.0105(5) -0.0031(5) 0.0023(4) -0.0012(5) C25 0.0190(6) 0.0165(6) 0.0135(6) -0.0059(5) 0.0037(5) 0.0002(5) C26 0.0178(6) 0.0136(6) 0.0139(6) -0.0037(5) 0.0034(5) -0.0021(5) C27 0.0164(6) 0.0158(6) 0.0117(6) -0.0035(5) 0.0011(5) -0.0018(5) O21 0.0354(6) 0.0143(5) 0.0151(5) -0.0013(4) 0.0117(4) -0.0012(4) O22 0.0248(5) 0.0172(5) 0.0138(5) -0.0045(4) 0.0067(4) -0.0002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C15 1.8895(14) . ? Cl1 C23 1.7303(14) . ? Cl2 C24 1.7293(14) . ? N11 C16 1.3425(18) . ? N11 C12 1.3472(17) . ? C12 N12 1.3929(17) . ? C12 C13 1.4021(18) . ? N12 C17 1.3804(17) . ? N12 H12 0.83(2) . ? C13 C14 1.3836(19) . ? C13 H13 0.9500 . ? C14 C15 1.3925(19) . ? C14 H14 0.9500 . ? C15 C16 1.3825(19) . ? C16 H16 0.9500 . ? C17 O17 1.2176(17) . ? C17 C18 1.5160(19) . ? C18 C19 1.526(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C21 C22 1.3962(19) . ? C21 C26 1.3968(18) . ? C21 C27 1.4947(19) . ? C22 C23 1.3901(18) . ? C22 H22 0.9500 . ? C23 C24 1.4003(19) . ? C24 C25 1.391(2) . ? C25 C26 1.3890(19) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 O22 1.2260(17) . ? C27 O21 1.3192(17) . ? O21 H21 0.90(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 C16 N11 C12 119.24(12) . . ? N11 C12 N12 113.88(11) . . ? N11 C12 C13 121.48(12) . . ? N12 C12 C13 124.63(12) . . ? C17 N12 C12 127.53(12) . . ? C17 N12 H12 117.4(13) . . ? C12 N12 H12 114.9(13) . . ? C14 C13 C12 118.90(12) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C15 119.13(12) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C16 C15 C14 118.95(12) . . ? C16 C15 Br1 120.01(10) . . ? C14 C15 Br1 121.03(10) . . ? N11 C16 C15 122.29(13) . . ? N11 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? O17 C17 N12 123.43(13) . . ? O17 C17 C18 123.10(12) . . ? N12 C17 C18 113.44(12) . . ? C17 C18 C19 112.69(12) . . ? C17 C18 H18A 109.1 . . ? C19 C18 H18A 109.1 . . ? C17 C18 H18B 109.1 . . ? C19 C18 H18B 109.1 . . ? H18A C18 H18B 107.8 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C22 C21 C26 120.07(12) . . ? C22 C21 C27 118.88(12) . . ? C26 C21 C27 121.04(12) . . ? C23 C22 C21 119.77(12) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C22 C23 C24 119.87(12) . . ? C22 C23 Cl1 119.40(10) . . ? C24 C23 Cl1 120.73(10) . . ? C25 C24 C23 120.35(12) . . ? C25 C24 Cl2 119.18(10) . . ? C23 C24 Cl2 120.46(11) . . ? C26 C25 C24 119.69(12) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C25 C26 C21 120.22(13) . . ? C25 C26 H26 119.9 . . ? C21 C26 H26 119.9 . . ? O22 C27 O21 123.75(13) . . ? O22 C27 C21 122.32(12) . . ? O21 C27 C21 113.93(12) . . ? C27 O21 H21 109.5(13) . . ? 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 -179.66(12) . . . . ? C16 N11 C12 C13 0.2(2) . . . . ? N11 C12 N12 C17 -178.59(13) . . . . ? C13 C12 N12 C17 1.6(2) . . . . ? N11 C12 C13 C14 0.1(2) . . . . ? N12 C12 C13 C14 179.95(13) . . . . ? C12 C13 C14 C15 -0.3(2) . . . . ? C13 C14 C15 C16 0.2(2) . . . . ? C13 C14 C15 Br1 -178.75(11) . . . . ? C12 N11 C16 C15 -0.3(2) . . . . ? C14 C15 C16 N11 0.1(2) . . . . ? Br1 C15 C16 N11 179.08(11) . . . . ? C12 N12 C17 O17 3.3(2) . . . . ? C12 N12 C17 C18 -178.53(13) . . . . ? O17 C17 C18 C19 -13.0(2) . . . . ? N12 C17 C18 C19 168.79(13) . . . . ? C26 C21 C22 C23 -0.2(2) . . . . ? C27 C21 C22 C23 178.92(12) . . . . ? C21 C22 C23 C24 -1.1(2) . . . . ? C21 C22 C23 Cl1 178.73(11) . . . . ? C22 C23 C24 C25 1.5(2) . . . . ? Cl1 C23 C24 C25 -178.33(11) . . . . ? C22 C23 C24 Cl2 -177.93(10) . . . . ? Cl1 C23 C24 Cl2 2.28(17) . . . . ? C23 C24 C25 C26 -0.5(2) . . . . ? Cl2 C24 C25 C26 178.85(11) . . . . ? C24 C25 C26 C21 -0.8(2) . . . . ? C22 C21 C26 C25 1.2(2) . . . . ? C27 C21 C26 C25 -177.98(12) . . . . ? C22 C21 C27 O22 -9.1(2) . . . . ? C26 C21 C27 O22 170.06(13) . . . . ? C22 C21 C27 O21 171.19(13) . . . . ? C26 C21 C27 O21 -9.67(19) . . . . ? 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 H12 O22 0.83(2) 2.09(2) 2.9242(16) 174.0(18) . O21 H21 N11 0.90(2) 1.74(2) 2.6274(16) 170(2) . _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.710 _refine_diff_density_min -0.774 _refine_diff_density_rms 0.079 #END data_ar0729m(D11) _database_code_depnum_ccdc_archive 'CCDC 772249' #TrackingRef '- allcifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (N-5-bromo-2-pyridyl)-propionamide)2, octanedioic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C8 H9 N2 O Br)2 (C8 H14 O4) ; _chemical_formula_sum 'C24 H32 Br2 N4 O6' _chemical_formula_weight 632.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 5.3172(2) _cell_length_b 8.6548(3) _cell_length_c 14.9927(6) _cell_angle_alpha 101.970(2) _cell_angle_beta 93.037(2) _cell_angle_gamma 100.816(2) _cell_volume 659.92(4) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5090 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 27.13 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 322 _exptl_absorpt_coefficient_mu 3.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5703 _exptl_absorpt_correction_T_max 0.7061 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12733 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 27.13 _reflns_number_total 2892 _reflns_number_gt 2586 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.2000P] 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 2892 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0230 _refine_ls_wR_factor_ref 0.0567 _refine_ls_wR_factor_gt 0.0543 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.96917(4) -0.21456(2) 0.238312(13) 0.03021(7) Uani 1 1 d . . . N11 N 0.5464(3) 0.13526(17) 0.23390(10) 0.0209(3) Uani 1 1 d . . . C12 C 0.6536(3) 0.2527(2) 0.30675(11) 0.0189(3) Uani 1 1 d . . . N12 N 0.5356(3) 0.38427(18) 0.31984(10) 0.0217(3) Uani 1 1 d . . . H12 H 0.429(4) 0.377(3) 0.2837(15) 0.026 Uiso 1 1 d . . . C13 C 0.8627(3) 0.2397(2) 0.36339(12) 0.0213(4) Uani 1 1 d . . . H13 H 0.9357 0.3242 0.4145 0.026 Uiso 1 1 calc R . . C14 C 0.9601(3) 0.1011(2) 0.34301(12) 0.0232(4) Uani 1 1 d . . . H14 H 1.1026 0.0887 0.3799 0.028 Uiso 1 1 calc R . . C15 C 0.8483(3) -0.0202(2) 0.26809(12) 0.0214(4) Uani 1 1 d . . . C16 C 0.6427(3) 0.0007(2) 0.21546(12) 0.0222(4) Uani 1 1 d . . . H16 H 0.5663 -0.0829 0.1644 0.027 Uiso 1 1 calc R . . C17 C 0.5955(3) 0.5243(2) 0.38641(12) 0.0215(4) Uani 1 1 d . . . O17 O 0.7716(3) 0.55259(16) 0.44625(9) 0.0315(3) Uani 1 1 d . . . C18 C 0.4179(4) 0.6376(2) 0.37754(13) 0.0271(4) Uani 1 1 d . . . H18A H 0.2428 0.5879 0.3891 0.032 Uiso 1 1 calc R . . H18B H 0.4096 0.6534 0.3140 0.032 Uiso 1 1 calc R . . C19 C 0.5020(4) 0.8005(2) 0.44309(13) 0.0317(4) Uani 1 1 d . . . H19A H 0.3839 0.8707 0.4326 0.048 Uiso 1 1 calc R . . H19B H 0.6766 0.8496 0.4328 0.048 Uiso 1 1 calc R . . H19C H 0.4998 0.7866 0.5063 0.048 Uiso 1 1 calc R . . C21 C 0.0590(3) 0.2575(2) 0.11701(11) 0.0201(3) Uani 1 1 d . . . O21 O 0.1605(3) 0.12754(15) 0.10213(9) 0.0268(3) Uani 1 1 d . . . H21 H 0.264(4) 0.134(3) 0.1415(16) 0.032 Uiso 1 1 d . . . O22 O 0.1301(2) 0.36980(16) 0.18247(9) 0.0279(3) Uani 1 1 d . . . C22 C -0.1511(3) 0.2552(2) 0.04505(11) 0.0208(3) Uani 1 1 d . . . H22A H -0.2920 0.1613 0.0427 0.025 Uiso 1 1 calc R . . H22B H -0.0823 0.2425 -0.0155 0.025 Uiso 1 1 calc R . . C23 C -0.2576(3) 0.4087(2) 0.06445(11) 0.0200(3) Uani 1 1 d . . . H23A H -0.1125 0.5025 0.0740 0.024 Uiso 1 1 calc R . . H23B H -0.3414 0.4147 0.1221 0.024 Uiso 1 1 calc R . . C24 C -0.4511(3) 0.4217(2) -0.01100(11) 0.0208(4) Uani 1 1 d . . . H24A H -0.3691 0.4149 -0.0691 0.025 Uiso 1 1 calc R . . H24B H -0.5988 0.3295 -0.0200 0.025 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.03230(12) 0.02622(11) 0.03404(12) 0.00348(8) -0.00275(8) 0.01595(8) N11 0.0208(7) 0.0218(7) 0.0197(7) 0.0028(6) -0.0038(6) 0.0073(6) C12 0.0169(8) 0.0213(8) 0.0188(8) 0.0051(7) -0.0004(6) 0.0050(7) N12 0.0209(8) 0.0223(8) 0.0215(7) 0.0016(6) -0.0072(6) 0.0091(6) C13 0.0196(9) 0.0224(9) 0.0206(8) 0.0035(7) -0.0040(7) 0.0039(7) C14 0.0189(9) 0.0285(9) 0.0234(9) 0.0073(7) -0.0040(7) 0.0077(7) C15 0.0214(9) 0.0214(9) 0.0235(9) 0.0051(7) 0.0016(7) 0.0093(7) C16 0.0219(9) 0.0226(9) 0.0212(8) 0.0015(7) -0.0018(7) 0.0071(7) C17 0.0203(9) 0.0208(8) 0.0221(8) 0.0024(7) -0.0018(7) 0.0048(7) O17 0.0297(7) 0.0294(7) 0.0304(7) -0.0030(6) -0.0155(6) 0.0099(6) C18 0.0268(10) 0.0234(9) 0.0298(9) 0.0008(8) -0.0065(8) 0.0103(8) C19 0.0393(11) 0.0242(10) 0.0296(10) 0.0001(8) -0.0022(9) 0.0097(9) C21 0.0179(8) 0.0234(9) 0.0205(8) 0.0075(7) -0.0005(7) 0.0053(7) O21 0.0292(7) 0.0259(7) 0.0251(7) 0.0014(5) -0.0109(5) 0.0137(6) O22 0.0278(7) 0.0301(7) 0.0247(6) -0.0001(6) -0.0101(5) 0.0133(6) C22 0.0181(8) 0.0238(9) 0.0202(8) 0.0038(7) -0.0044(7) 0.0061(7) C23 0.0181(8) 0.0237(9) 0.0188(8) 0.0038(7) -0.0023(7) 0.0082(7) C24 0.0181(8) 0.0244(9) 0.0202(8) 0.0046(7) -0.0022(7) 0.0067(7) _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 C15 1.8886(17) . ? N11 C16 1.341(2) . ? N11 C12 1.344(2) . ? C12 N12 1.385(2) . ? C12 C13 1.399(2) . ? N12 C17 1.373(2) . ? N12 H12 0.75(2) . ? C13 C14 1.378(2) . ? C13 H13 0.9500 . ? C14 C15 1.387(3) . ? C14 H14 0.9500 . ? C15 C16 1.376(2) . ? C16 H16 0.9500 . ? C17 O17 1.214(2) . ? C17 C18 1.503(2) . ? C18 C19 1.515(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C21 O22 1.216(2) . ? C21 O21 1.320(2) . ? C21 C22 1.506(2) . ? O21 H21 0.77(2) . ? C22 C23 1.520(2) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.525(2) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C24 1.521(3) 2_465 ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 118.72(14) . . ? N11 C12 N12 113.55(14) . . ? N11 C12 C13 122.23(15) . . ? N12 C12 C13 124.22(16) . . ? C17 N12 C12 128.96(15) . . ? C17 N12 H12 117.5(17) . . ? C12 N12 H12 113.5(17) . . ? C14 C13 C12 118.22(16) . . ? C14 C13 H13 120.9 . . ? C12 C13 H13 120.9 . . ? C13 C14 C15 119.40(16) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 119.23(16) . . ? C16 C15 Br1 119.50(13) . . ? C14 C15 Br1 121.26(13) . . ? N11 C16 C15 122.19(16) . . ? N11 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? O17 C17 N12 123.56(16) . . ? O17 C17 C18 123.82(16) . . ? N12 C17 C18 112.62(15) . . ? C17 C18 C19 112.97(16) . . ? C17 C18 H18A 109.0 . . ? C19 C18 H18A 109.0 . . ? C17 C18 H18B 109.0 . . ? C19 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O22 C21 O21 123.10(16) . . ? O22 C21 C22 122.89(15) . . ? O21 C21 C22 114.00(15) . . ? C21 O21 H21 109.6(17) . . ? C21 C22 C23 111.87(14) . . ? C21 C22 H22A 109.2 . . ? C23 C22 H22A 109.2 . . ? C21 C22 H22B 109.2 . . ? C23 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? C22 C23 C24 114.45(14) . . ? C22 C23 H23A 108.6 . . ? C24 C23 H23A 108.6 . . ? C22 C23 H23B 108.6 . . ? C24 C23 H23B 108.6 . . ? H23A C23 H23B 107.6 . . ? C24 C24 C23 112.42(18) 2_465 . ? C24 C24 H24A 109.1 2_465 . ? C23 C24 H24A 109.1 . . ? C24 C24 H24B 109.1 2_465 . ? C23 C24 H24B 109.1 . . ? H24A C24 H24B 107.9 . . ? 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 N11 C12 N12 -178.96(15) . . . . ? C16 N11 C12 C13 0.5(2) . . . . ? N11 C12 N12 C17 -179.57(16) . . . . ? C13 C12 N12 C17 1.0(3) . . . . ? N11 C12 C13 C14 0.0(2) . . . . ? N12 C12 C13 C14 179.34(16) . . . . ? C12 C13 C14 C15 -0.3(3) . . . . ? C13 C14 C15 C16 0.2(3) . . . . ? C13 C14 C15 Br1 -178.71(13) . . . . ? C12 N11 C16 C15 -0.6(2) . . . . ? C14 C15 C16 N11 0.2(3) . . . . ? Br1 C15 C16 N11 179.19(13) . . . . ? C12 N12 C17 O17 0.1(3) . . . . ? C12 N12 C17 C18 -179.36(16) . . . . ? O17 C17 C18 C19 7.7(3) . . . . ? N12 C17 C18 C19 -172.82(16) . . . . ? O22 C21 C22 C23 0.4(2) . . . . ? O21 C21 C22 C23 -178.91(14) . . . . ? C21 C22 C23 C24 173.89(14) . . . . ? C22 C23 C24 C24 -179.14(17) . . . 2_465 ? 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 0.77(2) 1.98(2) 2.7538(19) 174(2) . N12 H12 O22 0.75(2) 2.12(2) 2.8686(19) 177(2) . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.13 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.285 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.056 #END data_ar0713m(D13) _database_code_depnum_ccdc_archive 'CCDC 772250' #TrackingRef '- allcifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; AR-1c-aa13 [N-(5-bromo-2-pyridyl)propionamide]2, fumaric acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C8 H9 N2 O Br)2 (C4 H4 O4) ; _chemical_formula_sum 'C20 H22 Br2 N4 O6' _chemical_formula_weight 574.24 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' 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 4.8333(3) _cell_length_b 9.5923(5) _cell_length_c 23.7901(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.961(2) _cell_angle_gamma 90.00 _cell_volume 1102.81(11) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7507 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 31.14 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.729 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 3.721 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.5232 _exptl_absorpt_correction_T_max 0.7551 _exptl_absorpt_process_details ? _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19971 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 31.28 _reflns_number_total 3473 _reflns_number_gt 2806 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.3000P] 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 3473 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0669 _refine_ls_wR_factor_gt 0.0628 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 Br1 Br 0.77917(4) -0.140736(19) 0.417648(7) 0.02370(7) Uani 1 1 d . . . N11 N 0.3156(3) 0.21417(15) 0.40596(6) 0.0156(3) Uani 1 1 d . . . C12 C 0.4189(4) 0.09027(18) 0.42056(7) 0.0176(3) Uani 1 1 d . . . H12 H 0.3449 0.0433 0.4521 0.021 Uiso 1 1 calc R . . C13 C 0.6284(4) 0.02848(17) 0.39155(7) 0.0173(3) Uani 1 1 d . . . C14 C 0.7298(4) 0.09358(19) 0.34437(7) 0.0194(3) Uani 1 1 d . . . H14 H 0.8695 0.0504 0.3228 0.023 Uiso 1 1 calc R . . C15 C 0.6262(4) 0.22124(18) 0.32915(7) 0.0184(3) Uani 1 1 d . . . H15 H 0.6936 0.2683 0.2970 0.022 Uiso 1 1 calc R . . C16 C 0.4202(3) 0.28084(17) 0.36164(7) 0.0152(3) Uani 1 1 d . . . N16 N 0.3058(3) 0.41018(16) 0.35190(6) 0.0165(3) Uani 1 1 d . . . H16 H 0.186(4) 0.426(2) 0.3715(8) 0.020 Uiso 1 1 d . . . C17 C 0.3981(4) 0.51260(18) 0.31657(7) 0.0174(3) Uani 1 1 d . . . O17 O 0.5890(3) 0.49682(13) 0.28463(5) 0.0227(3) Uani 1 1 d . . . C18 C 0.2365(4) 0.64551(18) 0.32132(8) 0.0229(4) Uani 1 1 d . . . H18A H 0.2321 0.6739 0.3613 0.028 Uiso 1 1 calc R . . H18B H 0.0435 0.6285 0.3085 0.028 Uiso 1 1 calc R . . C19 C 0.3565(4) 0.76276(19) 0.28721(8) 0.0242(4) Uani 1 1 d . . . H19A H 0.2507 0.8483 0.2937 0.036 Uiso 1 1 calc R . . H19B H 0.3466 0.7386 0.2472 0.036 Uiso 1 1 calc R . . H19C H 0.5501 0.7776 0.2986 0.036 Uiso 1 1 calc R . . C21 C -0.2014(3) 0.40907(18) 0.46368(7) 0.0148(3) Uani 1 1 d . . . O21 O -0.0948(3) 0.28584(13) 0.47280(5) 0.0182(3) Uani 1 1 d . . . H21 H 0.015(5) 0.276(2) 0.4525(9) 0.022 Uiso 1 1 d . . . O22 O -0.1247(3) 0.48995(13) 0.42785(5) 0.0195(3) Uani 1 1 d . . . C22 C -0.4294(3) 0.44166(17) 0.50215(7) 0.0151(3) Uani 1 1 d . . . H22 H -0.4749 0.3767 0.5307 0.018 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02582(11) 0.01894(10) 0.02654(10) 0.00447(7) 0.00629(7) 0.00779(7) N11 0.0151(7) 0.0164(7) 0.0153(6) -0.0009(5) 0.0030(5) 0.0013(5) C12 0.0179(8) 0.0175(8) 0.0174(8) 0.0007(6) 0.0015(6) -0.0007(7) C13 0.0189(8) 0.0151(8) 0.0180(8) -0.0003(6) 0.0000(7) 0.0028(6) C14 0.0183(8) 0.0211(9) 0.0190(8) -0.0031(6) 0.0043(7) 0.0040(7) C15 0.0186(8) 0.0204(9) 0.0163(8) 0.0008(6) 0.0055(7) 0.0027(7) C16 0.0138(7) 0.0175(8) 0.0143(7) 0.0002(6) 0.0005(6) 0.0001(6) N16 0.0152(7) 0.0173(7) 0.0172(7) 0.0012(5) 0.0064(6) 0.0033(6) C17 0.0170(8) 0.0198(9) 0.0153(7) 0.0006(6) 0.0002(6) 0.0003(7) O17 0.0237(7) 0.0221(7) 0.0226(6) 0.0023(5) 0.0102(5) 0.0020(5) C18 0.0245(9) 0.0198(9) 0.0248(9) 0.0049(7) 0.0092(7) 0.0044(7) C19 0.0283(10) 0.0190(9) 0.0253(9) 0.0049(7) 0.0034(8) 0.0026(8) C21 0.0136(7) 0.0153(8) 0.0154(7) -0.0019(6) -0.0005(6) -0.0005(6) O21 0.0170(6) 0.0176(6) 0.0203(6) 0.0011(5) 0.0076(5) 0.0052(5) O22 0.0192(6) 0.0195(6) 0.0201(6) 0.0025(5) 0.0068(5) 0.0030(5) C22 0.0136(7) 0.0167(8) 0.0152(7) -0.0006(6) 0.0031(6) -0.0020(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 Br1 C13 1.8805(17) . ? N11 C12 1.333(2) . ? N11 C16 1.339(2) . ? C12 C13 1.370(2) . ? C12 H12 0.9500 . ? C13 C14 1.382(2) . ? C14 C15 1.369(2) . ? C14 H14 0.9500 . ? C15 C16 1.393(2) . ? C15 H15 0.9500 . ? C16 N16 1.376(2) . ? N16 C17 1.372(2) . ? N16 H16 0.76(2) . ? C17 O17 1.215(2) . ? C17 C18 1.500(2) . ? C18 C19 1.509(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C21 O22 1.215(2) . ? C21 O21 1.306(2) . ? C21 C22 1.477(2) . ? O21 H21 0.73(2) . ? C22 C22 1.314(3) 3_466 ? C22 H22 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 C12 N11 C16 119.08(14) . . ? N11 C12 C13 122.09(15) . . ? N11 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? C12 C13 C14 119.29(16) . . ? C12 C13 Br1 119.52(13) . . ? C14 C13 Br1 121.17(13) . . ? C15 C14 C13 119.06(15) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C16 118.80(15) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? N11 C16 N16 114.01(14) . . ? N11 C16 C15 121.57(15) . . ? N16 C16 C15 124.43(15) . . ? C17 N16 C16 127.92(15) . . ? C17 N16 H16 119.3(16) . . ? C16 N16 H16 112.5(16) . . ? O17 C17 N16 123.51(16) . . ? O17 C17 C18 123.71(16) . . ? N16 C17 C18 112.78(14) . . ? C17 C18 C19 112.80(15) . . ? C17 C18 H18A 109.0 . . ? C19 C18 H18A 109.0 . . ? C17 C18 H18B 109.0 . . ? C19 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O22 C21 O21 124.76(15) . . ? O22 C21 C22 122.61(15) . . ? O21 C21 C22 112.63(14) . . ? C21 O21 H21 107.2(17) . . ? C22 C22 C21 121.60(19) 3_466 . ? C22 C22 H22 119.2 3_466 . ? C21 C22 H22 119.2 . . ? 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 C16 N11 C12 C13 -0.3(2) . . . . ? N11 C12 C13 C14 -2.5(3) . . . . ? N11 C12 C13 Br1 175.91(13) . . . . ? C12 C13 C14 C15 2.7(3) . . . . ? Br1 C13 C14 C15 -175.62(13) . . . . ? C13 C14 C15 C16 -0.4(3) . . . . ? C12 N11 C16 N16 -177.43(15) . . . . ? C12 N11 C16 C15 2.7(2) . . . . ? C14 C15 C16 N11 -2.3(3) . . . . ? C14 C15 C16 N16 177.79(16) . . . . ? N11 C16 N16 C17 167.95(16) . . . . ? C15 C16 N16 C17 -12.2(3) . . . . ? C16 N16 C17 O17 6.4(3) . . . . ? C16 N16 C17 C18 -174.11(16) . . . . ? O17 C17 C18 C19 -6.6(3) . . . . ? N16 C17 C18 C19 173.84(15) . . . . ? O22 C21 C22 C22 3.2(3) . . . 3_466 ? O21 C21 C22 C22 -176.94(19) . . . 3_466 ? 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 N16 H16 O22 0.76(2) 2.12(2) 2.8818(18) 174(2) . O21 H21 N11 0.73(2) 1.93(2) 2.6537(18) 168(2) . _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 31.28 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.514 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.083 #END data_ar0806m(D14) _database_code_depnum_ccdc_archive 'CCDC 772251' #TrackingRef '- allcifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; AR-1c-aa-14 N-(5-bromo-2-pyridyl)-propionamide, succinic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C8 H9 N2 O Br)2 (C4 H6 O4) ; _chemical_formula_sum 'C20 H24 Br2 N4 O6' _chemical_formula_weight 576.25 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' 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 13.8624(15) _cell_length_b 13.9754(16) _cell_length_c 24.726(3) _cell_angle_alpha 95.707(8) _cell_angle_beta 90.355(7) _cell_angle_gamma 101.437(7) _cell_volume 4670.1(9) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4147 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 28.61 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2320 _exptl_absorpt_coefficient_mu 3.515 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4736 _exptl_absorpt_correction_T_max 0.6778 _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 72939 _diffrn_reflns_av_R_equivalents 0.1786 _diffrn_reflns_av_sigmaI/netI 0.3365 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 0.83 _diffrn_reflns_theta_max 29.57 _reflns_number_total 26200 _reflns_number_gt 6714 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 26200 _refine_ls_number_parameters 457 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3711 _refine_ls_R_factor_gt 0.1567 _refine_ls_wR_factor_ref 0.4480 _refine_ls_wR_factor_gt 0.3532 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.164 _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 -0.55280(12) -0.06831(12) 0.41960(7) 0.0359(4) Uani 1 1 d . . . Br5_1 Br 0.78454(12) 0.21747(13) 0.46116(7) 0.0369(5) Uani 1 1 d . . . N11_1 N -0.2661(4) -0.1058(6) 0.4242(3) 0.025(3) Uiso 1 1 d G . . C12_1 C -0.2743(5) -0.2061(6) 0.4264(3) 0.026(3) Uiso 1 1 d G . . C13_1 C -0.3668(6) -0.2671(5) 0.4255(4) 0.029(3) Uiso 1 1 d G . . H13_1 H -0.3724 -0.3356 0.4270 0.034 Uiso 1 1 calc R . . C14_1 C -0.4510(4) -0.2278(6) 0.4225(4) 0.028(3) Uiso 1 1 d G . . H14_1 H -0.5142 -0.2695 0.4219 0.034 Uiso 1 1 calc R . . C15_1 C -0.4428(4) -0.1275(6) 0.4203(3) 0.024(3) Uiso 1 1 d G . . C16_1 C -0.3504(6) -0.0665(5) 0.4212(3) 0.023(3) Uiso 1 1 d G . . H16_1 H -0.3448 0.0021 0.4197 0.027 Uiso 1 1 calc R . . C17_1 C -0.1661(11) -0.3169(11) 0.4443(6) 0.026(3) Uiso 1 1 d . . . N17_1 N -0.1836(9) -0.2307(9) 0.4313(5) 0.029(3) Uiso 1 1 d . . . H17_1 H -0.1319 -0.1855 0.4253 0.035 Uiso 1 1 calc R . . O17_1 O -0.2308(8) -0.3867(8) 0.4506(4) 0.033(3) Uiso 1 1 d . . . C18_1 C -0.0566(11) -0.3168(12) 0.4496(6) 0.032(4) Uiso 1 1 d . . . H18A_1 H -0.0275 -0.3138 0.4132 0.038 Uiso 1 1 calc R . . H18B_1 H -0.0242 -0.2571 0.4728 0.038 Uiso 1 1 calc R . . C19_1 C -0.0354(12) -0.4060(12) 0.4736(6) 0.037(4) Uiso 1 1 d . . . H19A_1 H -0.0666 -0.4654 0.4506 0.056 Uiso 1 1 calc R . . H19B_1 H -0.0619 -0.4082 0.5102 0.056 Uiso 1 1 calc R . . H19C_1 H 0.0359 -0.4023 0.4755 0.056 Uiso 1 1 calc R . . N21_1 N 0.4970(5) 0.2540(6) 0.4495(3) 0.024(3) Uiso 1 1 d G . . C22_1 C 0.5056(5) 0.3538(6) 0.4454(3) 0.025(3) Uiso 1 1 d G . . C23_1 C 0.5982(6) 0.4146(5) 0.4467(4) 0.031(4) Uiso 1 1 d G . . H23_1 H 0.6041 0.4828 0.4438 0.037 Uiso 1 1 calc R . . C24_1 C 0.6821(5) 0.3756(6) 0.4521(4) 0.027(3) Uiso 1 1 d G . . H24_1 H 0.7454 0.4172 0.4530 0.032 Uiso 1 1 calc R . . C25_1 C 0.6735(5) 0.2758(7) 0.4562(4) 0.031(4) Uiso 1 1 d G . . C26_1 C 0.5809(6) 0.2150(5) 0.4549(3) 0.028(3) Uiso 1 1 d G . . H26_1 H 0.5750 0.1468 0.4577 0.033 Uiso 1 1 calc R . . C27_1 C 0.3998(11) 0.4684(12) 0.4280(6) 0.029(4) Uiso 1 1 d . . . N27_1 N 0.4183(9) 0.3784(9) 0.4400(5) 0.028(3) Uiso 1 1 d . . . H27_1 H 0.3664 0.3325 0.4445 0.034 Uiso 1 1 calc R . . O27_1 O 0.4654(8) 0.5366(8) 0.4211(4) 0.034(3) Uiso 1 1 d . . . C28_1 C 0.2926(11) 0.4673(11) 0.4232(6) 0.032(4) Uiso 1 1 d . . . H28A_1 H 0.2632 0.4598 0.4593 0.039 Uiso 1 1 calc R . . H28B_1 H 0.2612 0.4097 0.3982 0.039 Uiso 1 1 calc R . . C29_1 C 0.2702(12) 0.5603(12) 0.4023(6) 0.038(4) Uiso 1 1 d . . . H29A_1 H 0.1993 0.5513 0.3946 0.056 Uiso 1 1 calc R . . H29B_1 H 0.3062 0.5730 0.3690 0.056 Uiso 1 1 calc R . . H29C_1 H 0.2906 0.6161 0.4300 0.056 Uiso 1 1 calc R . . C31_1 C -0.0208(11) 0.0099(11) 0.4299(6) 0.025(3) Uiso 1 1 d . . . O31_1 O -0.1036(8) 0.0379(8) 0.4241(4) 0.035(3) Uiso 1 1 d . . . H31_1 H -0.1502 -0.0108 0.4238 0.042 Uiso 1 1 calc R . . O32_1 O -0.0142(8) -0.0733(8) 0.4368(4) 0.035(3) Uiso 1 1 d . . . C32_1 C 0.0685(10) 0.0930(11) 0.4308(6) 0.028(3) Uiso 1 1 d . . . H32A_1 H 0.0618 0.1449 0.4600 0.033 Uiso 1 1 calc R . . H32B_1 H 0.0714 0.1219 0.3957 0.033 Uiso 1 1 calc R . . C33_1 C 0.1636(10) 0.0575(11) 0.4403(6) 0.028(3) Uiso 1 1 d . . . H33A_1 H 0.1604 0.0289 0.4755 0.034 Uiso 1 1 calc R . . H33B_1 H 0.1693 0.0048 0.4113 0.034 Uiso 1 1 calc R . . C34_1 C 0.2548(10) 0.1381(11) 0.4409(5) 0.021(3) Uiso 1 1 d . . . O33_1 O 0.2460(8) 0.2238(8) 0.4333(4) 0.033(3) Uiso 1 1 d . . . O34_1 O 0.3354(8) 0.1129(8) 0.4478(4) 0.033(3) Uiso 1 1 d . . . H34_1 H 0.3815 0.1619 0.4473 0.040 Uiso 1 1 calc R . . Br2_2 Br -0.31660(11) 0.08507(14) 0.29783(7) 0.0384(5) Uani 1 1 d . . . Br6_2 Br 1.01890(12) 0.36317(13) 0.34645(8) 0.0400(5) Uani 1 1 d . . . N11_2 N -0.0307(5) 0.0431(6) 0.2931(3) 0.031(3) Uiso 1 1 d G . . C12_2 C -0.0400(5) -0.0573(6) 0.2952(3) 0.026(3) Uiso 1 1 d G . . C13_2 C -0.1328(6) -0.1170(5) 0.2962(4) 0.027(3) Uiso 1 1 d G . . H13_2 H -0.1391 -0.1857 0.2976 0.032 Uiso 1 1 calc R . . C14_2 C -0.2164(5) -0.0763(6) 0.2951(4) 0.032(4) Uiso 1 1 d G . . H14_2 H -0.2799 -0.1171 0.2958 0.039 Uiso 1 1 calc R . . C15_2 C -0.2072(5) 0.0241(7) 0.2930(4) 0.033(4) Uiso 1 1 d G . . C16_2 C -0.1144(6) 0.0838(5) 0.2920(3) 0.034(4) Uiso 1 1 d G . . H16_2 H -0.1081 0.1524 0.2905 0.041 Uiso 1 1 calc R . . C17_2 C 0.0649(11) -0.1702(11) 0.3156(6) 0.025(3) Uiso 1 1 d . . . N17_2 N 0.0487(8) -0.0826(9) 0.2997(4) 0.023(3) Uiso 1 1 d . . . H17_2 H 0.1007 -0.0395 0.2918 0.028 Uiso 1 1 calc R . . O17_2 O -0.0001(8) -0.2407(8) 0.3201(4) 0.034(3) Uiso 1 1 d . . . C18_2 C 0.1742(11) -0.1683(12) 0.3216(6) 0.033(4) Uiso 1 1 d . . . H18A_2 H 0.2035 -0.1704 0.2852 0.040 Uiso 1 1 calc R . . H18B_2 H 0.2065 -0.1063 0.3429 0.040 Uiso 1 1 calc R . . C19_2 C 0.1928(13) -0.2544(13) 0.3499(7) 0.047(5) Uiso 1 1 d . . . H19A_2 H 0.1648 -0.3158 0.3276 0.071 Uiso 1 1 calc R . . H19B_2 H 0.1619 -0.2538 0.3854 0.071 Uiso 1 1 calc R . . H19C_2 H 0.2639 -0.2494 0.3549 0.071 Uiso 1 1 calc R . . N21_2 N 0.7348(4) 0.4005(5) 0.3268(3) 0.022(3) Uiso 1 1 d G . . C22_2 C 0.7444(5) 0.4993(6) 0.3195(3) 0.020(3) Uiso 1 1 d G . . C23_2 C 0.8372(6) 0.5596(5) 0.3206(3) 0.028(3) Uiso 1 1 d G . . H23_2 H 0.8437 0.6270 0.3156 0.034 Uiso 1 1 calc R . . C24_2 C 0.9205(4) 0.5211(6) 0.3290(3) 0.020(3) Uiso 1 1 d G . . H24_2 H 0.9840 0.5624 0.3298 0.024 Uiso 1 1 calc R . . C25_2 C 0.9110(5) 0.4224(6) 0.3363(3) 0.029(3) Uiso 1 1 d G . . C26_2 C 0.8182(6) 0.3621(5) 0.3352(3) 0.027(3) Uiso 1 1 d G . . H26_2 H 0.8117 0.2946 0.3402 0.032 Uiso 1 1 calc R . . C27_2 C 0.6415(12) 0.6134(12) 0.2971(6) 0.032(4) Uiso 1 1 d . . . N27_2 N 0.6564(9) 0.5250(9) 0.3105(4) 0.023(3) Uiso 1 1 d . . . H27_2 H 0.6033 0.4797 0.3138 0.028 Uiso 1 1 calc R . . O27_2 O 0.7065(8) 0.6834(8) 0.2916(4) 0.036(3) Uiso 1 1 d . . . C28_2 C 0.5306(12) 0.6131(13) 0.2904(7) 0.045(4) Uiso 1 1 d . . . H28A_2 H 0.5005 0.5595 0.2626 0.053 Uiso 1 1 calc R . . H28B_2 H 0.4978 0.6010 0.3252 0.053 Uiso 1 1 calc R . . C29_2 C 0.5156(13) 0.7082(13) 0.2739(7) 0.049(5) Uiso 1 1 d . . . H29A_2 H 0.5555 0.7620 0.2977 0.074 Uiso 1 1 calc R . . H29B_2 H 0.4459 0.7118 0.2769 0.074 Uiso 1 1 calc R . . H29C_2 H 0.5354 0.7138 0.2362 0.074 Uiso 1 1 calc R . . C31_2 C 0.2151(11) 0.1562(11) 0.3000(6) 0.025(3) Uiso 1 1 d . . . O31_2 O 0.1317(7) 0.1868(8) 0.2925(4) 0.032(2) Uiso 1 1 d . . . H31_2 H 0.0839 0.1394 0.2928 0.038 Uiso 1 1 calc R . . O32_2 O 0.2203(7) 0.0741(7) 0.3068(4) 0.026(2) Uiso 1 1 d . . . C32_2 C 0.3024(10) 0.2387(11) 0.3002(6) 0.026(3) Uiso 1 1 d . . . H32A_2 H 0.2945 0.2919 0.3284 0.031 Uiso 1 1 calc R . . H32B_2 H 0.3056 0.2655 0.2645 0.031 Uiso 1 1 calc R . . C33_2 C 0.3980(9) 0.2057(10) 0.3113(5) 0.020(3) Uiso 1 1 d . . . H33A_2 H 0.3938 0.1775 0.3466 0.024 Uiso 1 1 calc R . . H33B_2 H 0.4059 0.1531 0.2828 0.024 Uiso 1 1 calc R . . C34_2 C 0.4871(10) 0.2869(10) 0.3128(5) 0.019(3) Uiso 1 1 d . . . O33_2 O 0.4850(7) 0.3709(8) 0.3061(4) 0.031(2) Uiso 1 1 d . . . O34_2 O 0.5695(7) 0.2588(7) 0.3238(3) 0.024(2) Uiso 1 1 d . . . H34_2 H 0.6169 0.3068 0.3240 0.028 Uiso 1 1 calc R . . Br3_3 Br -0.06512(16) 0.22052(18) 0.16598(14) 0.1018(11) Uani 1 1 d . . . Br7_3 Br 1.26858(14) 0.49103(15) 0.23308(8) 0.0518(6) Uani 1 1 d . . . N11_3 N 0.2202(6) 0.1734(7) 0.1626(4) 0.051(4) Uiso 1 1 d G . . C12_3 C 0.2085(6) 0.0732(8) 0.1664(4) 0.040(4) Uiso 1 1 d G . . C13_3 C 0.1146(8) 0.0153(6) 0.1668(4) 0.043(4) Uiso 1 1 d G . . H13_3 H 0.1067 -0.0531 0.1694 0.052 Uiso 1 1 calc R . . C14_3 C 0.0324(6) 0.0576(8) 0.1634(4) 0.047(5) Uiso 1 1 d G . . H14_3 H -0.0317 0.0181 0.1636 0.057 Uiso 1 1 calc R . . C15_3 C 0.0441(7) 0.1578(8) 0.1595(4) 0.058(5) Uiso 1 1 d G . . C16_3 C 0.1379(8) 0.2157(6) 0.1591(4) 0.054(5) Uiso 1 1 d G . . H16_3 H 0.1459 0.2841 0.1565 0.065 Uiso 1 1 calc R . . C17_3 C 0.3120(12) -0.0398(13) 0.1881(6) 0.035(4) Uiso 1 1 d . . . N17_3 N 0.2946(10) 0.0470(10) 0.1740(5) 0.041(3) Uiso 1 1 d . . . H17_3 H 0.3473 0.0919 0.1692 0.049 Uiso 1 1 calc R . . O17_3 O 0.2465(9) -0.1149(9) 0.1917(5) 0.052(3) Uiso 1 1 d . . . C18_3 C 0.4170(12) -0.0429(13) 0.1993(6) 0.042(4) Uiso 1 1 d . . . H18A_3 H 0.4445 -0.0717 0.1661 0.050 Uiso 1 1 calc R . . H18B_3 H 0.4546 0.0250 0.2079 0.050 Uiso 1 1 calc R . . C19_3 C 0.429(3) -0.095(3) 0.2406(13) 0.193(18) Uiso 1 1 d . . . H19A_3 H 0.4935 -0.1137 0.2385 0.289 Uiso 1 1 calc R . . H19B_3 H 0.3772 -0.1549 0.2382 0.289 Uiso 1 1 calc R . . H19C_3 H 0.4246 -0.0560 0.2752 0.289 Uiso 1 1 calc R . . N21_3 N 0.9847(5) 0.5286(6) 0.2059(3) 0.029(3) Uiso 1 1 d G . . C22_3 C 0.9962(5) 0.6261(7) 0.1955(4) 0.035(4) Uiso 1 1 d G . . C23_3 C 1.0897(7) 0.6850(5) 0.1963(4) 0.034(4) Uiso 1 1 d G . . H23_3 H 1.0976 0.7516 0.1893 0.041 Uiso 1 1 calc R . . C24_3 C 1.1718(5) 0.6463(6) 0.2075(4) 0.031(4) Uiso 1 1 d G . . H24_3 H 1.2357 0.6865 0.2081 0.037 Uiso 1 1 calc R . . C25_3 C 1.1603(5) 0.5488(7) 0.2179(4) 0.029(3) Uiso 1 1 d G . . C26_3 C 1.0668(6) 0.4899(5) 0.2171(4) 0.035(4) Uiso 1 1 d G . . H26_3 H 1.0589 0.4233 0.2242 0.042 Uiso 1 1 calc R . . C27_3 C 0.8948(13) 0.7395(13) 0.1702(7) 0.041(4) Uiso 1 1 d . . . N27_3 N 0.9104(10) 0.6517(10) 0.1847(5) 0.034(3) Uiso 1 1 d . . . H27_3 H 0.8572 0.6061 0.1872 0.040 Uiso 1 1 calc R . . O27_3 O 0.9613(9) 0.8095(9) 0.1643(5) 0.052(3) Uiso 1 1 d . . . C28_3 C 0.7896(13) 0.7398(14) 0.1554(7) 0.051(5) Uiso 1 1 d . . . H28A_3 H 0.7663 0.6844 0.1272 0.061 Uiso 1 1 calc R . . H28B_3 H 0.7495 0.7271 0.1879 0.061 Uiso 1 1 calc R . . C29_3 C 0.7701(18) 0.8303(19) 0.1351(9) 0.103(9) Uiso 1 1 d . . . H29A_3 H 0.7912 0.8858 0.1629 0.154 Uiso 1 1 calc R . . H29B_3 H 0.6995 0.8226 0.1272 0.154 Uiso 1 1 calc R . . H29C_3 H 0.8068 0.8424 0.1019 0.154 Uiso 1 1 calc R . . C31_3 C 0.4665(13) 0.2828(13) 0.1730(7) 0.039(4) Uiso 1 1 d . . . O31_3 O 0.3839(9) 0.3134(9) 0.1614(4) 0.050(3) Uiso 1 1 d . . . H31_3 H 0.3357 0.2661 0.1609 0.060 Uiso 1 1 calc R . . O32_3 O 0.4694(8) 0.2038(8) 0.1826(4) 0.038(3) Uiso 1 1 d . . . C32_3 C 0.5532(11) 0.3674(11) 0.1736(6) 0.033(4) Uiso 1 1 d . . . H32A_3 H 0.5435 0.4215 0.2007 0.039 Uiso 1 1 calc R . . H32B_3 H 0.5594 0.3922 0.1374 0.039 Uiso 1 1 calc R . . C33_3 C 0.6476(12) 0.3310(12) 0.1884(6) 0.036(4) Uiso 1 1 d . . . H33A_3 H 0.6408 0.3058 0.2245 0.043 Uiso 1 1 calc R . . H33B_3 H 0.6568 0.2768 0.1613 0.043 Uiso 1 1 calc R . . C34_3 C 0.7382(11) 0.4161(11) 0.1896(6) 0.029(4) Uiso 1 1 d . . . O33_3 O 0.7343(9) 0.4988(9) 0.1788(4) 0.044(3) Uiso 1 1 d . . . O34_3 O 0.8190(8) 0.3871(8) 0.2037(4) 0.032(3) Uiso 1 1 d . . . H34_3 H 0.8673 0.4343 0.2042 0.038 Uiso 1 1 calc R . . Br4_4 Br 0.20413(16) 0.3111(2) 0.01780(13) 0.1043(11) Uani 1 1 d . . . Br8_4 Br 1.53189(15) 0.59662(18) 0.11226(9) 0.0657(7) Uani 1 1 d . . . N11_4 N 0.4877(5) 0.2717(6) 0.0359(4) 0.037(3) Uiso 1 1 d G . . C12_4 C 0.4757(6) 0.1725(7) 0.0426(4) 0.033(4) Uiso 1 1 d G . . C13_4 C 0.3817(7) 0.1144(5) 0.0417(4) 0.038(4) Uiso 1 1 d G . . H13_4 H 0.3735 0.0466 0.0463 0.046 Uiso 1 1 calc R . . C14_4 C 0.2998(5) 0.1555(7) 0.0341(4) 0.050(5) Uiso 1 1 d G . . H14_4 H 0.2356 0.1157 0.0335 0.060 Uiso 1 1 calc R . . C15_4 C 0.3118(6) 0.2547(8) 0.0274(4) 0.044(4) Uiso 1 1 d G . . C16_4 C 0.4057(7) 0.3128(6) 0.0283(4) 0.047(4) Uiso 1 1 d G . . H16_4 H 0.4139 0.3806 0.0237 0.056 Uiso 1 1 calc R . . C17_4 C 0.5760(13) 0.0605(13) 0.0687(7) 0.040(4) Uiso 1 1 d . . . N17_4 N 0.5604(10) 0.1462(10) 0.0536(5) 0.041(3) Uiso 1 1 d . . . H17_4 H 0.6137 0.1912 0.0505 0.050 Uiso 1 1 calc R . . O17_4 O 0.5076(9) -0.0163(9) 0.0697(5) 0.051(3) Uiso 1 1 d . . . C18_4 C 0.6778(13) 0.0525(14) 0.0862(6) 0.046(4) Uiso 1 1 d . . . H18A_4 H 0.6951 -0.0071 0.0669 0.056 Uiso 1 1 calc R . . H18B_4 H 0.7259 0.1103 0.0765 0.056 Uiso 1 1 calc R . . C19_4 C 0.6830(13) 0.0473(14) 0.1462(6) 0.056(5) Uiso 1 1 d . . . H19A_4 H 0.6346 -0.0092 0.1558 0.084 Uiso 1 1 calc R . . H19B_4 H 0.6687 0.1077 0.1652 0.084 Uiso 1 1 calc R . . H19C_4 H 0.7492 0.0401 0.1568 0.084 Uiso 1 1 calc R . . N21_4 N 1.2489(5) 0.6306(6) 0.0854(3) 0.030(3) Uiso 1 1 d G . . C22_4 C 1.2593(5) 0.7281(6) 0.0751(4) 0.032(4) Uiso 1 1 d G . . C23_4 C 1.3524(7) 0.7880(5) 0.0763(4) 0.037(4) Uiso 1 1 d G . . H23_4 H 1.3595 0.8546 0.0693 0.044 Uiso 1 1 calc R . . C24_4 C 1.4350(5) 0.7504(7) 0.0878(4) 0.044(4) Uiso 1 1 d G . . H24_4 H 1.4986 0.7913 0.0886 0.052 Uiso 1 1 calc R . . C25_4 C 1.4245(5) 0.6529(7) 0.0981(4) 0.037(4) Uiso 1 1 d G . . C26_4 C 1.3315(6) 0.5930(5) 0.0969(3) 0.034(4) Uiso 1 1 d G . . H26_4 H 1.3243 0.5264 0.1039 0.040 Uiso 1 1 calc R . . C27_4 C 1.1586(14) 0.8415(14) 0.0482(7) 0.049(5) Uiso 1 1 d . . . N27_4 N 1.1747(10) 0.7563(10) 0.0648(5) 0.034(3) Uiso 1 1 d . . . H27_4 H 1.1210 0.7127 0.0696 0.041 Uiso 1 1 calc R . . O27_4 O 1.2265(10) 0.9130(10) 0.0457(5) 0.058(4) Uiso 1 1 d . . . C28_4 C 1.0567(13) 0.8435(14) 0.0343(7) 0.050(5) Uiso 1 1 d . . . H28A_4 H 1.0179 0.7755 0.0302 0.060 Uiso 1 1 calc R . . H28B_4 H 1.0289 0.8806 0.0645 0.060 Uiso 1 1 calc R . . C29_4 C 1.047(3) 0.886(3) -0.0138(16) 0.23(2) Uiso 1 1 d . . . H29A_4 H 1.0105 0.9393 -0.0068 0.351 Uiso 1 1 calc R . . H29B_4 H 1.0122 0.8367 -0.0416 0.351 Uiso 1 1 calc R . . H29C_4 H 1.1130 0.9135 -0.0266 0.351 Uiso 1 1 calc R . . C31_4 C 0.7254(13) 0.3811(13) 0.0495(7) 0.041(4) Uiso 1 1 d . . . O31_4 O 0.6478(8) 0.4148(8) 0.0360(4) 0.040(3) Uiso 1 1 d . . . H31_4 H 0.5977 0.3696 0.0351 0.048 Uiso 1 1 calc R . . O32_4 O 0.7354(9) 0.3031(9) 0.0631(4) 0.044(3) Uiso 1 1 d . . . C32_4 C 0.8228(11) 0.4671(12) 0.0514(6) 0.036(4) Uiso 1 1 d . . . H32A_4 H 0.8327 0.4901 0.0148 0.043 Uiso 1 1 calc R . . H32B_4 H 0.8129 0.5233 0.0769 0.043 Uiso 1 1 calc R . . C33_4 C 0.9142(11) 0.4327(12) 0.0690(6) 0.038(4) Uiso 1 1 d . . . H33A_4 H 0.9241 0.3765 0.0436 0.046 Uiso 1 1 calc R . . H33B_4 H 0.9045 0.4100 0.1057 0.046 Uiso 1 1 calc R . . C34_4 C 1.0062(11) 0.5148(12) 0.0705(6) 0.032(4) Uiso 1 1 d . . . O33_4 O 1.0006(8) 0.5978(9) 0.0568(4) 0.043(3) Uiso 1 1 d . . . O34_4 O 1.0878(8) 0.4859(8) 0.0854(4) 0.040(3) Uiso 1 1 d . . . H34_4 H 1.1362 0.5327 0.0850 0.048 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 0.0258(8) 0.0289(9) 0.0479(10) -0.0019(8) -0.0006(7) -0.0041(7) Br5_1 0.0242(8) 0.0277(9) 0.0557(11) 0.0039(8) -0.0041(8) -0.0020(7) Br2_2 0.0178(8) 0.0525(12) 0.0396(9) -0.0070(9) -0.0026(7) 0.0000(8) Br6_2 0.0189(8) 0.0361(10) 0.0633(12) 0.0086(9) -0.0057(8) -0.0005(8) Br3_3 0.0371(12) 0.0636(16) 0.201(3) 0.0723(19) -0.0456(15) -0.0252(12) Br7_3 0.0353(10) 0.0499(12) 0.0557(12) -0.0066(10) 0.0047(9) -0.0203(9) Br4_4 0.0305(11) 0.117(2) 0.158(3) 0.083(2) -0.0238(13) -0.0350(14) Br8_4 0.0412(11) 0.0780(16) 0.0640(13) 0.0260(12) -0.0093(9) -0.0301(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1_1 C15_1 1.874(6) . ? Br5_1 C25_1 1.889(6) . ? N11_1 C12_1 1.3900 . ? N11_1 C16_1 1.3900 . ? C12_1 N17_1 1.376(13) . ? C12_1 C13_1 1.3900 . ? C13_1 C14_1 1.3900 . ? C13_1 H13_1 0.9500 . ? C14_1 C15_1 1.3900 . ? C14_1 H14_1 0.9500 . ? C15_1 C16_1 1.3900 . ? C16_1 H16_1 0.9500 . ? C17_1 O17_1 1.211(17) . ? C17_1 N17_1 1.344(19) . ? C17_1 C18_1 1.52(2) . ? N17_1 H17_1 0.8800 . ? C18_1 C19_1 1.51(2) . ? C18_1 H18A_1 0.9900 . ? C18_1 H18B_1 0.9900 . ? C19_1 H19A_1 0.9800 . ? C19_1 H19B_1 0.9800 . ? C19_1 H19C_1 0.9800 . ? N21_1 C22_1 1.3900 . ? N21_1 C26_1 1.3900 . ? C22_1 N27_1 1.332(13) . ? C22_1 C23_1 1.3900 . ? C23_1 C24_1 1.3900 . ? C23_1 H23_1 0.9500 . ? C24_1 C25_1 1.3900 . ? C24_1 H24_1 0.9500 . ? C25_1 C26_1 1.3900 . ? C26_1 H26_1 0.9500 . ? C27_1 O27_1 1.207(17) . ? C27_1 N27_1 1.39(2) . ? C27_1 C28_1 1.49(2) . ? N27_1 H27_1 0.8800 . ? C28_1 C29_1 1.53(2) . ? C28_1 H28A_1 0.9900 . ? C28_1 H28B_1 0.9900 . ? C29_1 H29A_1 0.9800 . ? C29_1 H29B_1 0.9800 . ? C29_1 H29C_1 0.9800 . ? C31_1 O32_1 1.213(18) . ? C31_1 O31_1 1.294(18) . ? C31_1 C32_1 1.52(2) . ? O31_1 H31_1 0.8400 . ? C32_1 C33_1 1.523(19) . ? C32_1 H32A_1 0.9900 . ? C32_1 H32B_1 0.9900 . ? C33_1 C34_1 1.516(19) . ? C33_1 H33A_1 0.9900 . ? C33_1 H33B_1 0.9900 . ? C34_1 O34_1 1.252(17) . ? C34_1 O33_1 1.259(18) . ? O34_1 H34_1 0.8400 . ? Br2_2 C15_2 1.880(6) . ? Br6_2 C25_2 1.874(6) . ? N11_2 C12_2 1.3900 . ? N11_2 C16_2 1.3900 . ? C12_2 N17_2 1.352(13) . ? C12_2 C13_2 1.3900 . ? C13_2 C14_2 1.3900 . ? C13_2 H13_2 0.9500 . ? C14_2 C15_2 1.3900 . ? C14_2 H14_2 0.9500 . ? C15_2 C16_2 1.3900 . ? C16_2 H16_2 0.9500 . ? C17_2 O17_2 1.211(17) . ? C17_2 N17_2 1.381(19) . ? C17_2 C18_2 1.52(2) . ? N17_2 H17_2 0.8800 . ? C18_2 C19_2 1.51(2) . ? C18_2 H18A_2 0.9900 . ? C18_2 H18B_2 0.9900 . ? C19_2 H19A_2 0.9800 . ? C19_2 H19B_2 0.9800 . ? C19_2 H19C_2 0.9800 . ? N21_2 C22_2 1.3900 . ? N21_2 C26_2 1.3900 . ? C22_2 N27_2 1.361(13) . ? C22_2 C23_2 1.3900 . ? C23_2 C24_2 1.3900 . ? C23_2 H23_2 0.9500 . ? C24_2 C25_2 1.3900 . ? C24_2 H24_2 0.9500 . ? C25_2 C26_2 1.3900 . ? C26_2 H26_2 0.9500 . ? C27_2 O27_2 1.211(18) . ? C27_2 N27_2 1.36(2) . ? C27_2 C28_2 1.54(2) . ? N27_2 H27_2 0.8800 . ? C28_2 C29_2 1.48(2) . ? C28_2 H28A_2 0.9900 . ? C28_2 H28B_2 0.9900 . ? C29_2 H29A_2 0.9800 . ? C29_2 H29B_2 0.9800 . ? C29_2 H29C_2 0.9800 . ? C31_2 O32_2 1.193(18) . ? C31_2 O31_2 1.327(17) . ? C31_2 C32_2 1.50(2) . ? O31_2 H31_2 0.8400 . ? C32_2 C33_2 1.519(19) . ? C32_2 H32A_2 0.9900 . ? C32_2 H32B_2 0.9900 . ? C33_2 C34_2 1.501(18) . ? C33_2 H33A_2 0.9900 . ? C33_2 H33B_2 0.9900 . ? C34_2 O33_2 1.207(17) . ? C34_2 O34_2 1.314(16) . ? O34_2 H34_2 0.8400 . ? Br3_3 C15_3 1.894(8) . ? Br7_3 C25_3 1.892(7) . ? N11_3 C12_3 1.3900 . ? N11_3 C16_3 1.3900 . ? C12_3 N17_3 1.334(15) . ? C12_3 C13_3 1.3900 . ? C13_3 C14_3 1.3900 . ? C13_3 H13_3 0.9500 . ? C14_3 C15_3 1.3900 . ? C14_3 H14_3 0.9500 . ? C15_3 C16_3 1.3900 . ? C16_3 H16_3 0.9500 . ? C17_3 O17_3 1.255(19) . ? C17_3 N17_3 1.36(2) . ? C17_3 C18_3 1.49(2) . ? N17_3 H17_3 0.8800 . ? C18_3 C19_3 1.34(4) . ? C18_3 H18A_3 0.9900 . ? C18_3 H18B_3 0.9900 . ? C19_3 H19A_3 0.9800 . ? C19_3 H19B_3 0.9800 . ? C19_3 H19C_3 0.9800 . ? N21_3 C22_3 1.3900 . ? N21_3 C26_3 1.3900 . ? C22_3 N27_3 1.341(14) . ? C22_3 C23_3 1.3900 . ? C23_3 C24_3 1.3900 . ? C23_3 H23_3 0.9500 . ? C24_3 C25_3 1.3900 . ? C24_3 H24_3 0.9500 . ? C25_3 C26_3 1.3900 . ? C26_3 H26_3 0.9500 . ? C27_3 O27_3 1.22(2) . ? C27_3 N27_3 1.37(2) . ? C27_3 C28_3 1.50(2) . ? N27_3 H27_3 0.8800 . ? C28_3 C29_3 1.48(3) . ? C28_3 H28A_3 0.9900 . ? C28_3 H28B_3 0.9900 . ? C29_3 H29A_3 0.9800 . ? C29_3 H29B_3 0.9800 . ? C29_3 H29C_3 0.9800 . ? C31_3 O32_3 1.16(2) . ? C31_3 O31_3 1.34(2) . ? C31_3 C32_3 1.51(2) . ? O31_3 H31_3 0.8400 . ? C32_3 C33_3 1.55(2) . ? C32_3 H32A_3 0.9900 . ? C32_3 H32B_3 0.9900 . ? C33_3 C34_3 1.55(2) . ? C33_3 H33A_3 0.9900 . ? C33_3 H33B_3 0.9900 . ? C34_3 O33_3 1.224(19) . ? C34_3 O34_3 1.320(18) . ? O34_3 H34_3 0.8400 . ? Br4_4 C15_4 1.845(7) . ? Br8_4 C25_4 1.863(7) . ? N11_4 C12_4 1.3900 . ? N11_4 C16_4 1.3900 . ? C12_4 N17_4 1.332(15) . ? C12_4 C13_4 1.3900 . ? C13_4 C14_4 1.3900 . ? C13_4 H13_4 0.9500 . ? C14_4 C15_4 1.3900 . ? C14_4 H14_4 0.9500 . ? C15_4 C16_4 1.3900 . ? C16_4 H16_4 0.9500 . ? C17_4 O17_4 1.287(19) . ? C17_4 N17_4 1.35(2) . ? C17_4 C18_4 1.50(2) . ? N17_4 H17_4 0.8800 . ? C18_4 C19_4 1.49(2) . ? C18_4 H18A_4 0.9900 . ? C18_4 H18B_4 0.9900 . ? C19_4 H19A_4 0.9800 . ? C19_4 H19B_4 0.9800 . ? C19_4 H19C_4 0.9800 . ? N21_4 C22_4 1.3900 . ? N21_4 C26_4 1.3900 . ? C22_4 N27_4 1.341(14) . ? C22_4 C23_4 1.3900 . ? C23_4 C24_4 1.3900 . ? C23_4 H23_4 0.9500 . ? C24_4 C25_4 1.3900 . ? C24_4 H24_4 0.9500 . ? C25_4 C26_4 1.3900 . ? C26_4 H26_4 0.9500 . ? C27_4 O27_4 1.24(2) . ? C27_4 N27_4 1.36(2) . ? C27_4 C28_4 1.46(3) . ? N27_4 H27_4 0.8800 . ? C28_4 C29_4 1.40(4) . ? C28_4 H28A_4 0.9900 . ? C28_4 H28B_4 0.9900 . ? C29_4 H29A_4 0.9800 . ? C29_4 H29B_4 0.9800 . ? C29_4 H29C_4 0.9800 . ? C31_4 O32_4 1.21(2) . ? C31_4 O31_4 1.31(2) . ? C31_4 C32_4 1.62(2) . ? O31_4 H31_4 0.8400 . ? C32_4 C33_4 1.52(2) . ? C32_4 H32A_4 0.9900 . ? C32_4 H32B_4 0.9900 . ? C33_4 C34_4 1.53(2) . ? C33_4 H33A_4 0.9900 . ? C33_4 H33B_4 0.9900 . ? C34_4 O33_4 1.256(19) . ? C34_4 O34_4 1.336(19) . ? O34_4 H34_4 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 C12_1 N11_1 C16_1 120.0 . . ? N17_1 C12_1 C13_1 128.3(8) . . ? N17_1 C12_1 N11_1 111.7(8) . . ? C13_1 C12_1 N11_1 120.0 . . ? C12_1 C13_1 C14_1 120.0 . . ? C12_1 C13_1 H13_1 120.0 . . ? C14_1 C13_1 H13_1 120.0 . . ? C15_1 C14_1 C13_1 120.0 . . ? C15_1 C14_1 H14_1 120.0 . . ? C13_1 C14_1 H14_1 120.0 . . ? C16_1 C15_1 C14_1 120.0 . . ? C16_1 C15_1 Br1_1 117.5(5) . . ? C14_1 C15_1 Br1_1 122.5(5) . . ? C15_1 C16_1 N11_1 120.0 . . ? C15_1 C16_1 H16_1 120.0 . . ? N11_1 C16_1 H16_1 120.0 . . ? O17_1 C17_1 N17_1 123.3(14) . . ? O17_1 C17_1 C18_1 124.2(15) . . ? N17_1 C17_1 C18_1 112.5(13) . . ? C17_1 N17_1 C12_1 126.5(12) . . ? C17_1 N17_1 H17_1 116.8 . . ? C12_1 N17_1 H17_1 116.8 . . ? C19_1 C18_1 C17_1 113.2(13) . . ? C19_1 C18_1 H18A_1 108.9 . . ? C17_1 C18_1 H18A_1 108.9 . . ? C19_1 C18_1 H18B_1 108.9 . . ? C17_1 C18_1 H18B_1 108.9 . . ? H18A_1 C18_1 H18B_1 107.7 . . ? C18_1 C19_1 H19A_1 109.5 . . ? C18_1 C19_1 H19B_1 109.5 . . ? H19A_1 C19_1 H19B_1 109.5 . . ? C18_1 C19_1 H19C_1 109.5 . . ? H19A_1 C19_1 H19C_1 109.5 . . ? H19B_1 C19_1 H19C_1 109.5 . . ? C22_1 N21_1 C26_1 120.0 . . ? N27_1 C22_1 C23_1 127.9(8) . . ? N27_1 C22_1 N21_1 112.1(8) . . ? C23_1 C22_1 N21_1 120.0 . . ? C22_1 C23_1 C24_1 120.0 . . ? C22_1 C23_1 H23_1 120.0 . . ? C24_1 C23_1 H23_1 120.0 . . ? C25_1 C24_1 C23_1 120.0 . . ? C25_1 C24_1 H24_1 120.0 . . ? C23_1 C24_1 H24_1 120.0 . . ? C24_1 C25_1 C26_1 120.0 . . ? C24_1 C25_1 Br5_1 122.1(5) . . ? C26_1 C25_1 Br5_1 117.8(5) . . ? C25_1 C26_1 N21_1 120.0 . . ? C25_1 C26_1 H26_1 120.0 . . ? N21_1 C26_1 H26_1 120.0 . . ? O27_1 C27_1 N27_1 122.0(14) . . ? O27_1 C27_1 C28_1 125.9(15) . . ? N27_1 C27_1 C28_1 112.1(14) . . ? C22_1 N27_1 C27_1 127.4(12) . . ? C22_1 N27_1 H27_1 116.3 . . ? C27_1 N27_1 H27_1 116.3 . . ? C27_1 C28_1 C29_1 113.2(13) . . ? C27_1 C28_1 H28A_1 108.9 . . ? C29_1 C28_1 H28A_1 108.9 . . ? C27_1 C28_1 H28B_1 108.9 . . ? C29_1 C28_1 H28B_1 108.9 . . ? H28A_1 C28_1 H28B_1 107.8 . . ? C28_1 C29_1 H29A_1 109.5 . . ? C28_1 C29_1 H29B_1 109.5 . . ? H29A_1 C29_1 H29B_1 109.5 . . ? C28_1 C29_1 H29C_1 109.5 . . ? H29A_1 C29_1 H29C_1 109.5 . . ? H29B_1 C29_1 H29C_1 109.5 . . ? O32_1 C31_1 O31_1 124.0(14) . . ? O32_1 C31_1 C32_1 122.4(13) . . ? O31_1 C31_1 C32_1 113.5(13) . . ? C31_1 O31_1 H31_1 109.5 . . ? C31_1 C32_1 C33_1 111.6(12) . . ? C31_1 C32_1 H32A_1 109.3 . . ? C33_1 C32_1 H32A_1 109.3 . . ? C31_1 C32_1 H32B_1 109.3 . . ? C33_1 C32_1 H32B_1 109.3 . . ? H32A_1 C32_1 H32B_1 108.0 . . ? C34_1 C33_1 C32_1 113.3(12) . . ? C34_1 C33_1 H33A_1 108.9 . . ? C32_1 C33_1 H33A_1 108.9 . . ? C34_1 C33_1 H33B_1 108.9 . . ? C32_1 C33_1 H33B_1 108.9 . . ? H33A_1 C33_1 H33B_1 107.7 . . ? O34_1 C34_1 O33_1 124.3(14) . . ? O34_1 C34_1 C33_1 116.2(13) . . ? O33_1 C34_1 C33_1 119.5(13) . . ? C34_1 O34_1 H34_1 109.5 . . ? C12_2 N11_2 C16_2 120.0 . . ? N17_2 C12_2 C13_2 128.1(8) . . ? N17_2 C12_2 N11_2 111.7(8) . . ? C13_2 C12_2 N11_2 120.0 . . ? C14_2 C13_2 C12_2 120.0 . . ? C14_2 C13_2 H13_2 120.0 . . ? C12_2 C13_2 H13_2 120.0 . . ? C13_2 C14_2 C15_2 120.0 . . ? C13_2 C14_2 H14_2 120.0 . . ? C15_2 C14_2 H14_2 120.0 . . ? C14_2 C15_2 C16_2 120.0 . . ? C14_2 C15_2 Br2_2 122.0(5) . . ? C16_2 C15_2 Br2_2 117.8(5) . . ? C15_2 C16_2 N11_2 120.0 . . ? C15_2 C16_2 H16_2 120.0 . . ? N11_2 C16_2 H16_2 120.0 . . ? O17_2 C17_2 N17_2 123.6(14) . . ? O17_2 C17_2 C18_2 125.3(15) . . ? N17_2 C17_2 C18_2 110.9(13) . . ? C12_2 N17_2 C17_2 125.8(12) . . ? C12_2 N17_2 H17_2 117.1 . . ? C17_2 N17_2 H17_2 117.1 . . ? C19_2 C18_2 C17_2 111.3(13) . . ? C19_2 C18_2 H18A_2 109.4 . . ? C17_2 C18_2 H18A_2 109.4 . . ? C19_2 C18_2 H18B_2 109.4 . . ? C17_2 C18_2 H18B_2 109.4 . . ? H18A_2 C18_2 H18B_2 108.0 . . ? C18_2 C19_2 H19A_2 109.5 . . ? C18_2 C19_2 H19B_2 109.5 . . ? H19A_2 C19_2 H19B_2 109.5 . . ? C18_2 C19_2 H19C_2 109.5 . . ? H19A_2 C19_2 H19C_2 109.5 . . ? H19B_2 C19_2 H19C_2 109.5 . . ? C22_2 N21_2 C26_2 120.0 . . ? N27_2 C22_2 N21_2 112.9(8) . . ? N27_2 C22_2 C23_2 127.1(8) . . ? N21_2 C22_2 C23_2 120.0 . . ? C22_2 C23_2 C24_2 120.0 . . ? C22_2 C23_2 H23_2 120.0 . . ? C24_2 C23_2 H23_2 120.0 . . ? C25_2 C24_2 C23_2 120.0 . . ? C25_2 C24_2 H24_2 120.0 . . ? C23_2 C24_2 H24_2 120.0 . . ? C26_2 C25_2 C24_2 120.0 . . ? C26_2 C25_2 Br6_2 116.8(5) . . ? C24_2 C25_2 Br6_2 123.2(5) . . ? C25_2 C26_2 N21_2 120.0 . . ? C25_2 C26_2 H26_2 120.0 . . ? N21_2 C26_2 H26_2 120.0 . . ? O27_2 C27_2 N27_2 124.6(15) . . ? O27_2 C27_2 C28_2 124.2(16) . . ? N27_2 C27_2 C28_2 111.2(14) . . ? C22_2 N27_2 C27_2 127.1(12) . . ? C22_2 N27_2 H27_2 116.4 . . ? C27_2 N27_2 H27_2 116.4 . . ? C29_2 C28_2 C27_2 110.6(15) . . ? C29_2 C28_2 H28A_2 109.5 . . ? C27_2 C28_2 H28A_2 109.5 . . ? C29_2 C28_2 H28B_2 109.5 . . ? C27_2 C28_2 H28B_2 109.5 . . ? H28A_2 C28_2 H28B_2 108.1 . . ? C28_2 C29_2 H29A_2 109.5 . . ? C28_2 C29_2 H29B_2 109.5 . . ? H29A_2 C29_2 H29B_2 109.5 . . ? C28_2 C29_2 H29C_2 109.5 . . ? H29A_2 C29_2 H29C_2 109.5 . . ? H29B_2 C29_2 H29C_2 109.5 . . ? O32_2 C31_2 O31_2 124.8(14) . . ? O32_2 C31_2 C32_2 123.9(14) . . ? O31_2 C31_2 C32_2 111.3(13) . . ? C31_2 O31_2 H31_2 109.5 . . ? C31_2 C32_2 C33_2 111.9(12) . . ? C31_2 C32_2 H32A_2 109.2 . . ? C33_2 C32_2 H32A_2 109.2 . . ? C31_2 C32_2 H32B_2 109.2 . . ? C33_2 C32_2 H32B_2 109.2 . . ? H32A_2 C32_2 H32B_2 107.9 . . ? C34_2 C33_2 C32_2 113.4(12) . . ? C34_2 C33_2 H33A_2 108.9 . . ? C32_2 C33_2 H33A_2 108.9 . . ? C34_2 C33_2 H33B_2 108.9 . . ? C32_2 C33_2 H33B_2 108.9 . . ? H33A_2 C33_2 H33B_2 107.7 . . ? O33_2 C34_2 O34_2 122.2(13) . . ? O33_2 C34_2 C33_2 124.4(13) . . ? O34_2 C34_2 C33_2 113.4(12) . . ? C34_2 O34_2 H34_2 109.5 . . ? C12_3 N11_3 C16_3 120.0 . . ? N17_3 C12_3 N11_3 111.7(10) . . ? N17_3 C12_3 C13_3 128.0(10) . . ? N11_3 C12_3 C13_3 120.0 . . ? C14_3 C13_3 C12_3 120.0 . . ? C14_3 C13_3 H13_3 120.0 . . ? C12_3 C13_3 H13_3 120.0 . . ? C13_3 C14_3 C15_3 120.0 . . ? C13_3 C14_3 H14_3 120.0 . . ? C15_3 C14_3 H14_3 120.0 . . ? C16_3 C15_3 C14_3 120.0 . . ? C16_3 C15_3 Br3_3 118.6(7) . . ? C14_3 C15_3 Br3_3 120.7(7) . . ? C15_3 C16_3 N11_3 120.0 . . ? C15_3 C16_3 H16_3 120.0 . . ? N11_3 C16_3 H16_3 120.0 . . ? O17_3 C17_3 N17_3 124.4(16) . . ? O17_3 C17_3 C18_3 119.7(16) . . ? N17_3 C17_3 C18_3 115.9(15) . . ? C12_3 N17_3 C17_3 128.7(14) . . ? C12_3 N17_3 H17_3 115.7 . . ? C17_3 N17_3 H17_3 115.7 . . ? C19_3 C18_3 C17_3 113(2) . . ? C19_3 C18_3 H18A_3 109.0 . . ? C17_3 C18_3 H18A_3 109.0 . . ? C19_3 C18_3 H18B_3 109.0 . . ? C17_3 C18_3 H18B_3 109.0 . . ? H18A_3 C18_3 H18B_3 107.8 . . ? C18_3 C19_3 H19A_3 109.5 . . ? C18_3 C19_3 H19B_3 109.5 . . ? H19A_3 C19_3 H19B_3 109.5 . . ? C18_3 C19_3 H19C_3 109.5 . . ? H19A_3 C19_3 H19C_3 109.5 . . ? H19B_3 C19_3 H19C_3 109.5 . . ? C22_3 N21_3 C26_3 120.0 . . ? N27_3 C22_3 N21_3 112.7(9) . . ? N27_3 C22_3 C23_3 127.3(9) . . ? N21_3 C22_3 C23_3 120.0 . . ? C24_3 C23_3 C22_3 120.0 . . ? C24_3 C23_3 H23_3 120.0 . . ? C22_3 C23_3 H23_3 120.0 . . ? C25_3 C24_3 C23_3 120.0 . . ? C25_3 C24_3 H24_3 120.0 . . ? C23_3 C24_3 H24_3 120.0 . . ? C24_3 C25_3 C26_3 120.0 . . ? C24_3 C25_3 Br7_3 122.4(5) . . ? C26_3 C25_3 Br7_3 117.6(5) . . ? C25_3 C26_3 N21_3 120.0 . . ? C25_3 C26_3 H26_3 120.0 . . ? N21_3 C26_3 H26_3 120.0 . . ? O27_3 C27_3 N27_3 123.5(16) . . ? O27_3 C27_3 C28_3 121.8(17) . . ? N27_3 C27_3 C28_3 114.3(16) . . ? C22_3 N27_3 C27_3 128.4(14) . . ? C22_3 N27_3 H27_3 115.8 . . ? C27_3 N27_3 H27_3 115.8 . . ? C29_3 C28_3 C27_3 116.4(18) . . ? C29_3 C28_3 H28A_3 108.2 . . ? C27_3 C28_3 H28A_3 108.2 . . ? C29_3 C28_3 H28B_3 108.2 . . ? C27_3 C28_3 H28B_3 108.2 . . ? H28A_3 C28_3 H28B_3 107.3 . . ? C28_3 C29_3 H29A_3 109.5 . . ? C28_3 C29_3 H29B_3 109.5 . . ? H29A_3 C29_3 H29B_3 109.5 . . ? C28_3 C29_3 H29C_3 109.5 . . ? H29A_3 C29_3 H29C_3 109.5 . . ? H29B_3 C29_3 H29C_3 109.5 . . ? O32_3 C31_3 O31_3 124.5(17) . . ? O32_3 C31_3 C32_3 125.9(16) . . ? O31_3 C31_3 C32_3 109.5(15) . . ? C31_3 O31_3 H31_3 109.5 . . ? C31_3 C32_3 C33_3 108.7(13) . . ? C31_3 C32_3 H32A_3 110.0 . . ? C33_3 C32_3 H32A_3 110.0 . . ? C31_3 C32_3 H32B_3 110.0 . . ? C33_3 C32_3 H32B_3 110.0 . . ? H32A_3 C32_3 H32B_3 108.3 . . ? C34_3 C33_3 C32_3 110.1(13) . . ? C34_3 C33_3 H33A_3 109.6 . . ? C32_3 C33_3 H33A_3 109.6 . . ? C34_3 C33_3 H33B_3 109.6 . . ? C32_3 C33_3 H33B_3 109.6 . . ? H33A_3 C33_3 H33B_3 108.1 . . ? O33_3 C34_3 O34_3 125.3(15) . . ? O33_3 C34_3 C33_3 123.8(14) . . ? O34_3 C34_3 C33_3 110.9(13) . . ? C34_3 O34_3 H34_3 109.5 . . ? C12_4 N11_4 C16_4 120.0 . . ? N17_4 C12_4 N11_4 112.7(9) . . ? N17_4 C12_4 C13_4 127.1(9) . . ? N11_4 C12_4 C13_4 120.0 . . ? C14_4 C13_4 C12_4 120.0 . . ? C14_4 C13_4 H13_4 120.0 . . ? C12_4 C13_4 H13_4 120.0 . . ? C15_4 C14_4 C13_4 120.0 . . ? C15_4 C14_4 H14_4 120.0 . . ? C13_4 C14_4 H14_4 120.0 . . ? C16_4 C15_4 C14_4 120.0 . . ? C16_4 C15_4 Br4_4 119.2(6) . . ? C14_4 C15_4 Br4_4 120.8(6) . . ? C15_4 C16_4 N11_4 120.0 . . ? C15_4 C16_4 H16_4 120.0 . . ? N11_4 C16_4 H16_4 120.0 . . ? O17_4 C17_4 N17_4 123.6(16) . . ? O17_4 C17_4 C18_4 117.0(16) . . ? N17_4 C17_4 C18_4 119.4(16) . . ? C12_4 N17_4 C17_4 129.2(14) . . ? C12_4 N17_4 H17_4 115.4 . . ? C17_4 N17_4 H17_4 115.4 . . ? C19_4 C18_4 C17_4 110.4(14) . . ? C19_4 C18_4 H18A_4 109.6 . . ? C17_4 C18_4 H18A_4 109.6 . . ? C19_4 C18_4 H18B_4 109.6 . . ? C17_4 C18_4 H18B_4 109.6 . . ? H18A_4 C18_4 H18B_4 108.1 . . ? C18_4 C19_4 H19A_4 109.5 . . ? C18_4 C19_4 H19B_4 109.5 . . ? H19A_4 C19_4 H19B_4 109.5 . . ? C18_4 C19_4 H19C_4 109.5 . . ? H19A_4 C19_4 H19C_4 109.5 . . ? H19B_4 C19_4 H19C_4 109.5 . . ? C22_4 N21_4 C26_4 120.0 . . ? N27_4 C22_4 C23_4 125.2(9) . . ? N27_4 C22_4 N21_4 114.8(9) . . ? C23_4 C22_4 N21_4 120.0 . . ? C22_4 C23_4 C24_4 120.0 . . ? C22_4 C23_4 H23_4 120.0 . . ? C24_4 C23_4 H23_4 120.0 . . ? C23_4 C24_4 C25_4 120.0 . . ? C23_4 C24_4 H24_4 120.0 . . ? C25_4 C24_4 H24_4 120.0 . . ? C26_4 C25_4 C24_4 120.0 . . ? C26_4 C25_4 Br8_4 117.5(6) . . ? C24_4 C25_4 Br8_4 122.5(6) . . ? C25_4 C26_4 N21_4 120.0 . . ? C25_4 C26_4 H26_4 120.0 . . ? N21_4 C26_4 H26_4 120.0 . . ? O27_4 C27_4 N27_4 121.6(18) . . ? O27_4 C27_4 C28_4 122.6(19) . . ? N27_4 C27_4 C28_4 115.8(17) . . ? C22_4 N27_4 C27_4 130.2(14) . . ? C22_4 N27_4 H27_4 114.9 . . ? C27_4 N27_4 H27_4 114.9 . . ? C29_4 C28_4 C27_4 113(2) . . ? C29_4 C28_4 H28A_4 109.1 . . ? C27_4 C28_4 H28A_4 109.1 . . ? C29_4 C28_4 H28B_4 109.1 . . ? C27_4 C28_4 H28B_4 109.1 . . ? H28A_4 C28_4 H28B_4 107.8 . . ? C28_4 C29_4 H29A_4 109.5 . . ? C28_4 C29_4 H29B_4 109.5 . . ? H29A_4 C29_4 H29B_4 109.5 . . ? C28_4 C29_4 H29C_4 109.5 . . ? H29A_4 C29_4 H29C_4 109.5 . . ? H29B_4 C29_4 H29C_4 109.5 . . ? O32_4 C31_4 O31_4 132.6(17) . . ? O32_4 C31_4 C32_4 117.1(15) . . ? O31_4 C31_4 C32_4 110.2(14) . . ? C31_4 O31_4 H31_4 109.5 . . ? C33_4 C32_4 C31_4 112.2(13) . . ? C33_4 C32_4 H32A_4 109.2 . . ? C31_4 C32_4 H32A_4 109.2 . . ? C33_4 C32_4 H32B_4 109.2 . . ? C31_4 C32_4 H32B_4 109.2 . . ? H32A_4 C32_4 H32B_4 107.9 . . ? C32_4 C33_4 C34_4 111.7(13) . . ? C32_4 C33_4 H33A_4 109.3 . . ? C34_4 C33_4 H33A_4 109.3 . . ? C32_4 C33_4 H33B_4 109.3 . . ? C34_4 C33_4 H33B_4 109.3 . . ? H33A_4 C33_4 H33B_4 107.9 . . ? O33_4 C34_4 O34_4 126.6(15) . . ? O33_4 C34_4 C33_4 120.6(15) . . ? O34_4 C34_4 C33_4 112.7(14) . . ? C34_4 O34_4 H34_4 109.5 . . ? 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 N17_1 -177.8(8) . . . . ? C16_1 N11_1 C12_1 C13_1 0.0 . . . . ? N17_1 C12_1 C13_1 C14_1 177.4(10) . . . . ? N11_1 C12_1 C13_1 C14_1 0.0 . . . . ? C12_1 C13_1 C14_1 C15_1 0.0 . . . . ? C13_1 C14_1 C15_1 C16_1 0.0 . . . . ? C13_1 C14_1 C15_1 Br1_1 -177.0(6) . . . . ? C14_1 C15_1 C16_1 N11_1 0.0 . . . . ? Br1_1 C15_1 C16_1 N11_1 177.1(6) . . . . ? C12_1 N11_1 C16_1 C15_1 0.0 . . . . ? O17_1 C17_1 N17_1 C12_1 4(2) . . . . ? C18_1 C17_1 N17_1 C12_1 -176.4(11) . . . . ? C13_1 C12_1 N17_1 C17_1 -10.6(17) . . . . ? N11_1 C12_1 N17_1 C17_1 167.0(11) . . . . ? O17_1 C17_1 C18_1 C19_1 -11(2) . . . . ? N17_1 C17_1 C18_1 C19_1 169.9(12) . . . . ? C26_1 N21_1 C22_1 N27_1 179.5(9) . . . . ? C26_1 N21_1 C22_1 C23_1 0.0 . . . . ? N27_1 C22_1 C23_1 C24_1 -179.4(10) . . . . ? N21_1 C22_1 C23_1 C24_1 0.0 . . . . ? C22_1 C23_1 C24_1 C25_1 0.0 . . . . ? C23_1 C24_1 C25_1 C26_1 0.0 . . . . ? C23_1 C24_1 C25_1 Br5_1 177.8(7) . . . . ? C24_1 C25_1 C26_1 N21_1 0.0 . . . . ? Br5_1 C25_1 C26_1 N21_1 -177.9(6) . . . . ? C22_1 N21_1 C26_1 C25_1 0.0 . . . . ? C23_1 C22_1 N27_1 C27_1 8.3(18) . . . . ? N21_1 C22_1 N27_1 C27_1 -171.2(11) . . . . ? O27_1 C27_1 N27_1 C22_1 0(2) . . . . ? C28_1 C27_1 N27_1 C22_1 177.9(12) . . . . ? O27_1 C27_1 C28_1 C29_1 6(2) . . . . ? N27_1 C27_1 C28_1 C29_1 -171.9(12) . . . . ? O32_1 C31_1 C32_1 C33_1 0.9(19) . . . . ? O31_1 C31_1 C32_1 C33_1 177.3(11) . . . . ? C31_1 C32_1 C33_1 C34_1 179.4(13) . . . . ? C32_1 C33_1 C34_1 O34_1 -179.1(11) . . . . ? C32_1 C33_1 C34_1 O33_1 -0.7(18) . . . . ? C16_2 N11_2 C12_2 N17_2 -175.8(9) . . . . ? C16_2 N11_2 C12_2 C13_2 0.0 . . . . ? N17_2 C12_2 C13_2 C14_2 175.1(10) . . . . ? N11_2 C12_2 C13_2 C14_2 0.0 . . . . ? C12_2 C13_2 C14_2 C15_2 0.0 . . . . ? C13_2 C14_2 C15_2 C16_2 0.0 . . . . ? C13_2 C14_2 C15_2 Br2_2 -174.3(7) . . . . ? C14_2 C15_2 C16_2 N11_2 0.0 . . . . ? Br2_2 C15_2 C16_2 N11_2 174.5(6) . . . . ? C12_2 N11_2 C16_2 C15_2 0.0 . . . . ? C13_2 C12_2 N17_2 C17_2 -11.9(17) . . . . ? N11_2 C12_2 N17_2 C17_2 163.5(11) . . . . ? O17_2 C17_2 N17_2 C12_2 11(2) . . . . ? C18_2 C17_2 N17_2 C12_2 -174.1(11) . . . . ? O17_2 C17_2 C18_2 C19_2 -17(2) . . . . ? N17_2 C17_2 C18_2 C19_2 168.3(12) . . . . ? C26_2 N21_2 C22_2 N27_2 178.7(8) . . . . ? C26_2 N21_2 C22_2 C23_2 0.0 . . . . ? N27_2 C22_2 C23_2 C24_2 -178.5(10) . . . . ? N21_2 C22_2 C23_2 C24_2 0.0 . . . . ? C22_2 C23_2 C24_2 C25_2 0.0 . . . . ? C23_2 C24_2 C25_2 C26_2 0.0 . . . . ? C23_2 C24_2 C25_2 Br6_2 178.6(6) . . . . ? C24_2 C25_2 C26_2 N21_2 0.0 . . . . ? Br6_2 C25_2 C26_2 N21_2 -178.7(6) . . . . ? C22_2 N21_2 C26_2 C25_2 0.0 . . . . ? N21_2 C22_2 N27_2 C27_2 -173.6(11) . . . . ? C23_2 C22_2 N27_2 C27_2 5.0(17) . . . . ? O27_2 C27_2 N27_2 C22_2 -1(2) . . . . ? C28_2 C27_2 N27_2 C22_2 179.9(11) . . . . ? O27_2 C27_2 C28_2 C29_2 3(2) . . . . ? N27_2 C27_2 C28_2 C29_2 -177.9(13) . . . . ? O32_2 C31_2 C32_2 C33_2 -1(2) . . . . ? O31_2 C31_2 C32_2 C33_2 177.3(11) . . . . ? C31_2 C32_2 C33_2 C34_2 -179.0(12) . . . . ? C32_2 C33_2 C34_2 O33_2 0(2) . . . . ? C32_2 C33_2 C34_2 O34_2 178.3(11) . . . . ? C16_3 N11_3 C12_3 N17_3 -174.7(10) . . . . ? C16_3 N11_3 C12_3 C13_3 0.0 . . . . ? N17_3 C12_3 C13_3 C14_3 173.8(12) . . . . ? N11_3 C12_3 C13_3 C14_3 0.0 . . . . ? C12_3 C13_3 C14_3 C15_3 0.0 . . . . ? C13_3 C14_3 C15_3 C16_3 0.0 . . . . ? C13_3 C14_3 C15_3 Br3_3 -170.3(8) . . . . ? C14_3 C15_3 C16_3 N11_3 0.0 . . . . ? Br3_3 C15_3 C16_3 N11_3 170.5(8) . . . . ? C12_3 N11_3 C16_3 C15_3 0.0 . . . . ? N11_3 C12_3 N17_3 C17_3 168.5(13) . . . . ? C13_3 C12_3 N17_3 C17_3 -6(2) . . . . ? O17_3 C17_3 N17_3 C12_3 7(3) . . . . ? C18_3 C17_3 N17_3 C12_3 -173.6(13) . . . . ? O17_3 C17_3 C18_3 C19_3 -38(3) . . . . ? N17_3 C17_3 C18_3 C19_3 142(2) . . . . ? C26_3 N21_3 C22_3 N27_3 179.1(9) . . . . ? C26_3 N21_3 C22_3 C23_3 0.0 . . . . ? N27_3 C22_3 C23_3 C24_3 -178.9(11) . . . . ? N21_3 C22_3 C23_3 C24_3 0.0 . . . . ? C22_3 C23_3 C24_3 C25_3 0.0 . . . . ? C23_3 C24_3 C25_3 C26_3 0.0 . . . . ? C23_3 C24_3 C25_3 Br7_3 179.7(7) . . . . ? C24_3 C25_3 C26_3 N21_3 0.0 . . . . ? Br7_3 C25_3 C26_3 N21_3 -179.7(6) . . . . ? C22_3 N21_3 C26_3 C25_3 0.0 . . . . ? N21_3 C22_3 N27_3 C27_3 -176.5(13) . . . . ? C23_3 C22_3 N27_3 C27_3 2.5(19) . . . . ? O27_3 C27_3 N27_3 C22_3 1(3) . . . . ? C28_3 C27_3 N27_3 C22_3 174.0(13) . . . . ? O27_3 C27_3 C28_3 C29_3 -2(3) . . . . ? N27_3 C27_3 C28_3 C29_3 -175.2(16) . . . . ? O32_3 C31_3 C32_3 C33_3 1(2) . . . . ? O31_3 C31_3 C32_3 C33_3 178.7(12) . . . . ? C31_3 C32_3 C33_3 C34_3 -179.9(13) . . . . ? C32_3 C33_3 C34_3 O33_3 -2(2) . . . . ? C32_3 C33_3 C34_3 O34_3 178.1(12) . . . . ? C16_4 N11_4 C12_4 N17_4 -175.2(10) . . . . ? C16_4 N11_4 C12_4 C13_4 0.0 . . . . ? N17_4 C12_4 C13_4 C14_4 174.4(11) . . . . ? N11_4 C12_4 C13_4 C14_4 0.0 . . . . ? C12_4 C13_4 C14_4 C15_4 0.0 . . . . ? C13_4 C14_4 C15_4 C16_4 0.0 . . . . ? C13_4 C14_4 C15_4 Br4_4 -179.5(7) . . . . ? C14_4 C15_4 C16_4 N11_4 0.0 . . . . ? Br4_4 C15_4 C16_4 N11_4 179.5(7) . . . . ? C12_4 N11_4 C16_4 C15_4 0.0 . . . . ? N11_4 C12_4 N17_4 C17_4 171.3(13) . . . . ? C13_4 C12_4 N17_4 C17_4 -3(2) . . . . ? O17_4 C17_4 N17_4 C12_4 7(3) . . . . ? C18_4 C17_4 N17_4 C12_4 -171.7(13) . . . . ? O17_4 C17_4 C18_4 C19_4 -71(2) . . . . ? N17_4 C17_4 C18_4 C19_4 108.1(19) . . . . ? C26_4 N21_4 C22_4 N27_4 -179.7(9) . . . . ? C26_4 N21_4 C22_4 C23_4 0.0 . . . . ? N27_4 C22_4 C23_4 C24_4 179.7(10) . . . . ? N21_4 C22_4 C23_4 C24_4 0.0 . . . . ? C22_4 C23_4 C24_4 C25_4 0.0 . . . . ? C23_4 C24_4 C25_4 C26_4 0.0 . . . . ? C23_4 C24_4 C25_4 Br8_4 178.6(7) . . . . ? C24_4 C25_4 C26_4 N21_4 0.0 . . . . ? Br8_4 C25_4 C26_4 N21_4 -178.7(7) . . . . ? C22_4 N21_4 C26_4 C25_4 0.0 . . . . ? C23_4 C22_4 N27_4 C27_4 8(2) . . . . ? N21_4 C22_4 N27_4 C27_4 -172.8(14) . . . . ? O27_4 C27_4 N27_4 C22_4 -8(3) . . . . ? C28_4 C27_4 N27_4 C22_4 172.7(13) . . . . ? O27_4 C27_4 C28_4 C29_4 45(3) . . . . ? N27_4 C27_4 C28_4 C29_4 -136(2) . . . . ? O32_4 C31_4 C32_4 C33_4 2(2) . . . . ? O31_4 C31_4 C32_4 C33_4 177.7(12) . . . . ? C31_4 C32_4 C33_4 C34_4 179.8(13) . . . . ? C32_4 C33_4 C34_4 O33_4 -2(2) . . . . ? C32_4 C33_4 C34_4 O34_4 -179.3(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O31_1 H31_1 N11_1 0.84 1.87 2.705(12) 171.6 . O31_2 H31_2 N11_2 0.84 1.87 2.705(12) 174.1 . O31_3 H31_3 N11_3 0.84 1.85 2.689(14) 172.9 . O31_4 H31_4 N11_4 0.84 1.84 2.677(13) 177.8 . N17_1 H17_1 O32_1 0.88 2.02 2.874(17) 162.3 . N17_2 H17_2 O32_2 0.88 2.06 2.887(15) 156.7 . N17_3 H17_3 O32_3 0.88 2.06 2.917(18) 163.0 . N17_4 H17_4 O32_4 0.88 2.06 2.921(18) 166.2 . O34_1 H34_1 N21_1 0.84 1.84 2.672(12) 169.5 . O34_2 H34_2 N21_2 0.84 1.88 2.711(11) 171.2 . O34_3 H34_3 N21_3 0.84 1.88 2.714(12) 173.1 . O34_4 H34_4 N21_4 0.84 1.86 2.699(13) 176.2 . N27_1 H27_1 O33_1 0.88 2.02 2.878(16) 164.8 . N27_2 H27_2 O33_2 0.88 2.00 2.867(16) 169.3 . N27_3 H27_3 O33_3 0.88 2.03 2.900(18) 170.1 . N27_4 H27_4 O33_4 0.88 2.07 2.926(18) 163.1 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 4.708 _refine_diff_density_min -2.630 _refine_diff_density_rms 0.276 #END data_ar0921m(D15) _database_code_depnum_ccdc_archive 'CCDC 772252' #TrackingRef '- allcifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; AR-BI-C4 N-(5-bromo-2-pyridyl)propionamide, HOOC-(CH2)8-COOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C8 H9 N2 O Br)2 (C10 H18 O4) ; _chemical_formula_sum 'C26 H36 Br2 N4 O6' _chemical_formula_weight 660.41 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' 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 5.1849(4) _cell_length_b 11.4665(8) _cell_length_c 12.4870(9) _cell_angle_alpha 71.293(2) _cell_angle_beta 81.204(2) _cell_angle_gamma 88.593(2) _cell_volume 694.66(9) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6258 _cell_measurement_theta_min 3.60 _cell_measurement_theta_max 31.55 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 338 _exptl_absorpt_coefficient_mu 2.965 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3834 _exptl_absorpt_correction_T_max 0.7559 _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_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12522 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 31.51 _reflns_number_total 4500 _reflns_number_gt 3756 _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, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.2000P] 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 4500 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0758 _refine_ls_wR_factor_gt 0.0708 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 Br1 Br 0.77714(4) -0.454445(15) 0.213776(15) 0.02944(7) Uani 1 1 d . . . N11 N 0.7338(3) -0.10891(12) 0.24309(11) 0.0194(3) Uani 1 1 d . . . C12 C 0.9518(3) -0.05162(14) 0.17696(13) 0.0189(3) Uani 1 1 d . . . N12 N 0.9752(3) 0.07005(12) 0.17075(12) 0.0206(3) Uani 1 1 d . . . H12 H 0.855(4) 0.0941(19) 0.2089(18) 0.025 Uiso 1 1 d . . . C13 C 1.1355(3) -0.11091(15) 0.11985(14) 0.0220(3) Uani 1 1 d . . . H13 H 1.2898 -0.0686 0.0742 0.026 Uiso 1 1 calc R . . C14 C 1.0873(3) -0.23214(15) 0.13148(14) 0.0234(3) Uani 1 1 d . . . H14 H 1.2091 -0.2755 0.0944 0.028 Uiso 1 1 calc R . . C15 C 0.8594(3) -0.29007(14) 0.19789(13) 0.0211(3) Uani 1 1 d . . . C16 C 0.6886(3) -0.22603(14) 0.25227(14) 0.0213(3) Uani 1 1 d . . . H16 H 0.5328 -0.2666 0.2980 0.026 Uiso 1 1 calc R . . C21 C 1.1759(3) 0.15299(14) 0.11543(13) 0.0204(3) Uani 1 1 d . . . O21 O 1.3740(2) 0.12933(11) 0.06230(11) 0.0298(3) Uani 1 1 d . . . C22 C 1.1224(3) 0.27895(14) 0.12643(15) 0.0228(3) Uani 1 1 d . . . H22A H 1.0406 0.2695 0.2059 0.027 Uiso 1 1 calc R . . H22B H 0.9968 0.3203 0.0749 0.027 Uiso 1 1 calc R . . C23 C 1.3670(3) 0.35937(15) 0.09733(16) 0.0280(4) Uani 1 1 d . . . H23A H 1.3217 0.4397 0.1060 0.042 Uiso 1 1 calc R . . H23B H 1.4466 0.3708 0.0181 0.042 Uiso 1 1 calc R . . H23C H 1.4909 0.3197 0.1490 0.042 Uiso 1 1 calc R . . C31 C 0.4066(3) 0.09111(13) 0.37417(13) 0.0185(3) Uani 1 1 d . . . O31 O 0.3534(2) -0.02055(11) 0.37418(11) 0.0253(3) Uani 1 1 d . . . H31 H 0.463(5) -0.040(2) 0.335(2) 0.030 Uiso 1 1 d . . . O32 O 0.6072(2) 0.14713(11) 0.32375(11) 0.0260(3) Uani 1 1 d . . . C32 C 0.1958(3) 0.14306(14) 0.44073(13) 0.0191(3) Uani 1 1 d . . . H32A H 0.1672 0.0891 0.5215 0.023 Uiso 1 1 calc R . . H32B H 0.0311 0.1437 0.4096 0.023 Uiso 1 1 calc R . . C33 C 0.2624(3) 0.27277(14) 0.43627(14) 0.0212(3) Uani 1 1 d . . . H33A H 0.4112 0.2698 0.4781 0.025 Uiso 1 1 calc R . . H33B H 0.3188 0.3231 0.3555 0.025 Uiso 1 1 calc R . . C34 C 0.0376(3) 0.33511(14) 0.48697(14) 0.0202(3) Uani 1 1 d . . . H34A H -0.0164 0.2866 0.5684 0.024 Uiso 1 1 calc R . . H34B H -0.1130 0.3372 0.4463 0.024 Uiso 1 1 calc R . . C35 C 0.1117(3) 0.46564(14) 0.47809(15) 0.0222(3) Uani 1 1 d . . . H35A H 0.2566 0.4625 0.5221 0.027 Uiso 1 1 calc R . . H35B H 0.1761 0.5121 0.3970 0.027 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.03718(11) 0.02111(9) 0.03285(10) -0.01370(7) -0.00266(7) -0.00071(6) N11 0.0185(6) 0.0189(6) 0.0199(6) -0.0066(5) 0.0009(5) 0.0004(5) C12 0.0171(7) 0.0210(7) 0.0188(7) -0.0075(5) -0.0008(5) 0.0021(5) N12 0.0172(6) 0.0198(6) 0.0230(7) -0.0087(5) 0.0060(5) 0.0002(5) C13 0.0177(7) 0.0257(7) 0.0230(7) -0.0111(6) 0.0029(6) 0.0013(6) C14 0.0232(8) 0.0257(7) 0.0249(8) -0.0147(6) -0.0011(6) 0.0047(6) C15 0.0252(8) 0.0192(7) 0.0212(7) -0.0098(6) -0.0041(6) 0.0012(6) C16 0.0210(7) 0.0204(7) 0.0222(7) -0.0073(6) -0.0012(6) 0.0002(6) C21 0.0191(7) 0.0213(7) 0.0190(7) -0.0061(6) 0.0021(6) -0.0018(6) O21 0.0226(6) 0.0286(6) 0.0362(7) -0.0144(5) 0.0107(5) -0.0029(5) C22 0.0209(7) 0.0189(7) 0.0266(8) -0.0073(6) 0.0030(6) -0.0010(6) C23 0.0262(8) 0.0221(7) 0.0319(9) -0.0073(7) 0.0049(7) -0.0054(6) C31 0.0191(7) 0.0176(6) 0.0183(7) -0.0061(5) -0.0015(5) 0.0027(5) O31 0.0224(6) 0.0200(5) 0.0329(7) -0.0133(5) 0.0087(5) -0.0016(4) O32 0.0222(6) 0.0229(5) 0.0321(6) -0.0132(5) 0.0087(5) -0.0029(4) C32 0.0164(7) 0.0189(6) 0.0214(7) -0.0083(5) 0.0030(5) 0.0004(5) C33 0.0179(7) 0.0202(7) 0.0259(8) -0.0110(6) 0.0031(6) -0.0014(5) C34 0.0179(7) 0.0200(7) 0.0238(7) -0.0104(6) 0.0009(6) 0.0019(5) C35 0.0183(7) 0.0216(7) 0.0276(8) -0.0116(6) 0.0020(6) 0.0006(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 Br1 C15 1.8834(15) . ? N11 C16 1.334(2) . ? N11 C12 1.3392(19) . ? C12 N12 1.3796(19) . ? C12 C13 1.396(2) . ? N12 C21 1.3683(19) . ? N12 H12 0.82(2) . ? C13 C14 1.376(2) . ? C13 H13 0.9500 . ? C14 C15 1.383(2) . ? C14 H14 0.9500 . ? C15 C16 1.374(2) . ? C16 H16 0.9500 . ? C21 O21 1.2092(19) . ? C21 C22 1.509(2) . ? C22 C23 1.514(2) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C31 O32 1.2096(19) . ? C31 O31 1.3163(18) . ? C31 C32 1.499(2) . ? O31 H31 0.77(2) . ? C32 C33 1.517(2) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.514(2) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.519(2) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C35 1.516(3) 2_566 ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 118.54(13) . . ? N11 C12 N12 113.74(13) . . ? N11 C12 C13 122.39(14) . . ? N12 C12 C13 123.87(14) . . ? C21 N12 C12 128.97(13) . . ? C21 N12 H12 116.2(15) . . ? C12 N12 H12 114.7(15) . . ? C14 C13 C12 118.27(14) . . ? C14 C13 H13 120.9 . . ? C12 C13 H13 120.9 . . ? C13 C14 C15 119.10(14) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C16 C15 C14 119.33(14) . . ? C16 C15 Br1 119.48(12) . . ? C14 C15 Br1 121.19(12) . . ? N11 C16 C15 122.35(15) . . ? N11 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? O21 C21 N12 124.20(15) . . ? O21 C21 C22 123.20(14) . . ? N12 C21 C22 112.59(13) . . ? C21 C22 C23 112.74(14) . . ? C21 C22 H22A 109.0 . . ? C23 C22 H22A 109.0 . . ? C21 C22 H22B 109.0 . . ? C23 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O32 C31 O31 122.75(14) . . ? O32 C31 C32 123.11(14) . . ? O31 C31 C32 114.13(13) . . ? C31 O31 H31 109.5(17) . . ? C31 C32 C33 112.39(12) . . ? C31 C32 H32A 109.1 . . ? C33 C32 H32A 109.1 . . ? C31 C32 H32B 109.1 . . ? C33 C32 H32B 109.1 . . ? H32A C32 H32B 107.9 . . ? C34 C33 C32 113.66(12) . . ? C34 C33 H33A 108.8 . . ? C32 C33 H33A 108.8 . . ? C34 C33 H33B 108.8 . . ? C32 C33 H33B 108.8 . . ? H33A C33 H33B 107.7 . . ? C33 C34 C35 111.72(13) . . ? C33 C34 H34A 109.3 . . ? C35 C34 H34A 109.3 . . ? C33 C34 H34B 109.3 . . ? C35 C34 H34B 109.3 . . ? H34A C34 H34B 107.9 . . ? C35 C35 C34 113.68(16) 2_566 . ? C35 C35 H35A 108.8 2_566 . ? C34 C35 H35A 108.8 . . ? C35 C35 H35B 108.8 2_566 . ? C34 C35 H35B 108.8 . . ? H35A C35 H35B 107.7 . . ? 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 178.11(14) . . . . ? C16 N11 C12 C13 -1.6(2) . . . . ? N11 C12 N12 C21 177.01(16) . . . . ? C13 C12 N12 C21 -3.3(3) . . . . ? N11 C12 C13 C14 0.8(2) . . . . ? N12 C12 C13 C14 -178.92(16) . . . . ? C12 C13 C14 C15 0.6(3) . . . . ? C13 C14 C15 C16 -1.1(3) . . . . ? C13 C14 C15 Br1 178.20(13) . . . . ? C12 N11 C16 C15 1.1(2) . . . . ? C14 C15 C16 N11 0.3(3) . . . . ? Br1 C15 C16 N11 -179.04(12) . . . . ? C12 N12 C21 O21 -1.0(3) . . . . ? C12 N12 C21 C22 178.22(15) . . . . ? O21 C21 C22 C23 -17.8(2) . . . . ? N12 C21 C22 C23 162.97(15) . . . . ? O32 C31 C32 C33 0.5(2) . . . . ? O31 C31 C32 C33 -178.71(14) . . . . ? C31 C32 C33 C34 171.12(14) . . . . ? C32 C33 C34 C35 -178.69(14) . . . . ? C33 C34 C35 C35 176.85(18) . . . 2_566 ? 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 O31 H31 N11 0.77(2) 1.99(2) 2.7522(17) 174(2) . N12 H12 O32 0.82(2) 2.01(2) 2.8209(17) 169(2) . _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 31.51 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.464 _refine_diff_density_min -0.467 _refine_diff_density_rms 0.072 #END data_ar0817m(E9) _database_code_depnum_ccdc_archive 'CCDC 772253' #TrackingRef '- allcifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; AR-1i-9 2-amino-3,5-dibromopyridine, 3,5-dinitrobenzoic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C5 H4 Br2 N2) (C7 H4 N2 O6) ; _chemical_formula_sum 'C12 H8 Br2 N4 O6' _chemical_formula_weight 464.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.3849(5) _cell_length_b 31.340(2) _cell_length_c 13.3082(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.344(3) _cell_angle_gamma 90.00 _cell_volume 3080.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9986 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 31.40 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.001 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1808 _exptl_absorpt_coefficient_mu 5.303 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3883 _exptl_absorpt_correction_T_max 0.6763 _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35388 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -44 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 31.51 _reflns_number_total 10050 _reflns_number_gt 7774 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+2.5000P] 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 10050 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0928 _refine_ls_wR_factor_gt 0.0866 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 Br1_1 Br 0.72193(4) 0.146960(8) 0.41330(2) 0.02704(7) Uani 1 1 d . . . Br2_1 Br 0.77435(4) 0.326372(9) 0.43436(2) 0.02782(7) Uani 1 1 d . . . N11_1 N 0.5774(3) 0.24385(6) 0.21877(15) 0.0188(4) Uani 1 1 d . . . C12_1 C 0.6048(3) 0.20467(8) 0.25715(17) 0.0175(4) Uani 1 1 d . . . N12_1 N 0.5543(3) 0.17100(7) 0.20137(18) 0.0243(5) Uani 1 1 d . . . H12A_1 H 0.503(5) 0.1739(11) 0.144(3) 0.029 Uiso 1 1 d . . . H12B_1 H 0.572(5) 0.1444(11) 0.222(3) 0.029 Uiso 1 1 d . . . C13_1 C 0.6831(3) 0.20108(8) 0.35441(18) 0.0193(5) Uani 1 1 d . . . C14_1 C 0.7314(3) 0.23665(8) 0.40732(19) 0.0202(5) Uani 1 1 d . . . H14_1 H 0.7837 0.2342 0.4724 0.024 Uiso 1 1 calc R . . C15_1 C 0.7025(3) 0.27652(8) 0.36426(18) 0.0198(5) Uani 1 1 d . . . C16_1 C 0.6243(3) 0.27919(8) 0.27082(18) 0.0200(5) Uani 1 1 d . . . H16_1 H 0.6026 0.3065 0.2421 0.024 Uiso 1 1 calc R . . C21_1 C 0.2437(3) 0.25598(8) -0.08989(17) 0.0168(4) Uani 1 1 d . . . C27_1 C 0.3308(3) 0.23834(8) 0.00396(17) 0.0183(5) Uani 1 1 d . . . O21_1 O 0.4035(3) 0.26820(6) 0.06015(14) 0.0228(4) Uani 1 1 d . . . H21_1 H 0.460(5) 0.2576(11) 0.108(3) 0.027 Uiso 1 1 d . . . O22_1 O 0.3330(3) 0.20042(6) 0.02188(13) 0.0238(4) Uani 1 1 d . . . C22_1 C 0.1808(3) 0.22715(8) -0.16133(17) 0.0174(4) Uani 1 1 d . . . H22_1 H 0.1892 0.1973 -0.1502 0.021 Uiso 1 1 calc R . . C23_1 C 0.1056(3) 0.24313(8) -0.24915(18) 0.0189(5) Uani 1 1 d . . . N23_1 N 0.0377(3) 0.21280(7) -0.32466(15) 0.0214(4) Uani 1 1 d . . . O23_1 O 0.0340(3) 0.17484(6) -0.30298(16) 0.0361(5) Uani 1 1 d . . . O24_1 O -0.0141(3) 0.22713(7) -0.40541(14) 0.0298(4) Uani 1 1 d . . . C24_1 C 0.0885(3) 0.28636(8) -0.26890(18) 0.0196(5) Uani 1 1 d . . . H24_1 H 0.0361 0.2966 -0.3297 0.024 Uiso 1 1 calc R . . C25_1 C 0.1519(4) 0.31387(8) -0.19527(18) 0.0200(5) Uani 1 1 d . . . N25_1 N 0.1336(3) 0.36019(7) -0.21275(18) 0.0266(5) Uani 1 1 d . . . O25_1 O 0.0543(4) 0.37149(7) -0.28919(17) 0.0410(6) Uani 1 1 d . . . O26_1 O 0.1982(3) 0.38429(6) -0.15040(17) 0.0374(5) Uani 1 1 d . . . C26_1 C 0.2293(3) 0.29985(8) -0.10605(18) 0.0196(5) Uani 1 1 d . . . H26_1 H 0.2716 0.3196 -0.0571 0.023 Uiso 1 1 calc R . . Br3_2 Br 1.23158(4) 0.112305(8) 0.94001(2) 0.02585(7) Uani 1 1 d . . . Br4_2 Br 1.27338(4) -0.066815(8) 0.98756(2) 0.02563(7) Uani 1 1 d . . . N11_2 N 1.0274(3) 0.01094(6) 0.77751(15) 0.0180(4) Uani 1 1 d . . . C12_2 C 1.0663(3) 0.05094(8) 0.80742(18) 0.0178(4) Uani 1 1 d . . . N12_2 N 1.0047(3) 0.08360(7) 0.75133(17) 0.0248(5) Uani 1 1 d . . . H12A_2 H 0.938(5) 0.0774(11) 0.694(3) 0.030 Uiso 1 1 d . . . H12B_2 H 1.024(5) 0.1118(11) 0.773(3) 0.030 Uiso 1 1 d . . . C13_2 C 1.1733(3) 0.05683(7) 0.89586(18) 0.0187(5) Uani 1 1 d . . . C14_2 C 1.2348(3) 0.02233(8) 0.94921(18) 0.0196(5) Uani 1 1 d . . . H14_2 H 1.3067 0.0261 1.0079 0.024 Uiso 1 1 calc R . . C15_2 C 1.1894(3) -0.01864(8) 0.91536(18) 0.0191(5) Uani 1 1 d . . . C16_2 C 1.0858(3) -0.02332(8) 0.83025(18) 0.0192(5) Uani 1 1 d . . . H16_2 H 1.0545 -0.0512 0.8079 0.023 Uiso 1 1 calc R . . C21_2 C 0.7215(3) -0.00136(8) 0.46147(17) 0.0171(4) Uani 1 1 d . . . C27_2 C 0.8138(3) 0.01719(8) 0.55298(18) 0.0185(4) Uani 1 1 d . . . O21_2 O 0.8708(3) -0.01140(6) 0.61556(14) 0.0238(4) Uani 1 1 d . . . H21_2 H 0.942(4) 0.0015(10) 0.690(3) 0.029 Uiso 1 1 d . . . O22_2 O 0.8265(3) 0.05612(6) 0.56353(14) 0.0245(4) Uani 1 1 d . . . C22_2 C 0.6457(3) 0.02655(8) 0.39112(17) 0.0186(4) Uani 1 1 d . . . H22_2 H 0.6597 0.0565 0.3980 0.022 Uiso 1 1 calc R . . C23_2 C 0.5494(3) 0.00943(8) 0.31085(18) 0.0188(5) Uani 1 1 d . . . N23_2 N 0.4660(3) 0.03854(7) 0.23825(16) 0.0230(4) Uani 1 1 d . . . O23_2 O 0.5092(3) 0.07638(6) 0.24236(16) 0.0354(5) Uani 1 1 d . . . O24_2 O 0.3596(3) 0.02374(7) 0.17708(15) 0.0328(5) Uani 1 1 d . . . C24_2 C 0.5259(3) -0.03396(8) 0.29727(18) 0.0203(5) Uani 1 1 d . . . H24_2 H 0.4585 -0.0451 0.2422 0.024 Uiso 1 1 calc R . . C25_2 C 0.6055(4) -0.06029(8) 0.36789(18) 0.0207(5) Uani 1 1 d . . . N25_2 N 0.5809(4) -0.10681(7) 0.35580(18) 0.0303(5) Uani 1 1 d . . . O25_2 O 0.4902(4) -0.11915(7) 0.28522(19) 0.0546(8) Uani 1 1 d . . . O26_2 O 0.6547(4) -0.13017(7) 0.41709(18) 0.0449(6) Uani 1 1 d . . . C26_2 C 0.7025(3) -0.04524(8) 0.45012(18) 0.0195(5) Uani 1 1 d . . . H26_2 H 0.7546 -0.0644 0.4974 0.023 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 0.03380(15) 0.01901(12) 0.02821(13) 0.00641(9) -0.00876(11) -0.00134(10) Br2_1 0.03063(14) 0.02162(13) 0.03112(14) -0.00796(10) -0.00748(11) -0.00374(10) N11_1 0.0223(10) 0.0157(9) 0.0183(9) 0.0002(7) -0.0032(8) 0.0012(8) C12_1 0.0177(11) 0.0163(11) 0.0184(10) -0.0009(8) -0.0005(9) 0.0021(9) N12_1 0.0347(13) 0.0167(10) 0.0213(10) -0.0015(8) -0.0079(9) 0.0026(9) C13_1 0.0208(11) 0.0160(11) 0.0211(11) 0.0027(8) -0.0036(9) 0.0012(9) C14_1 0.0198(12) 0.0208(12) 0.0198(11) 0.0001(9) -0.0044(9) -0.0026(9) C15_1 0.0201(12) 0.0167(11) 0.0224(11) -0.0047(8) -0.0040(9) -0.0029(9) C16_1 0.0223(12) 0.0146(11) 0.0230(11) 0.0003(8) -0.0037(9) 0.0003(9) C21_1 0.0166(11) 0.0194(11) 0.0143(9) 0.0003(8) -0.0017(8) 0.0012(9) C27_1 0.0205(11) 0.0199(11) 0.0145(10) -0.0007(8) -0.0016(9) 0.0017(9) O21_1 0.0309(10) 0.0193(9) 0.0180(8) 0.0000(6) -0.0104(7) -0.0013(7) O22_1 0.0334(10) 0.0176(9) 0.0203(8) 0.0005(6) -0.0092(8) 0.0016(7) C22_1 0.0193(11) 0.0163(11) 0.0165(10) 0.0026(8) -0.0032(9) -0.0003(9) C23_1 0.0211(12) 0.0197(11) 0.0158(10) -0.0006(8) -0.0032(9) 0.0003(9) N23_1 0.0251(11) 0.0204(10) 0.0185(9) -0.0004(8) -0.0048(8) -0.0009(8) O23_1 0.0607(15) 0.0197(10) 0.0276(10) -0.0016(7) -0.0151(10) -0.0012(9) O24_1 0.0359(11) 0.0336(11) 0.0196(9) 0.0035(7) -0.0131(8) -0.0040(9) C24_1 0.0212(12) 0.0212(12) 0.0165(10) 0.0029(8) -0.0027(9) 0.0015(9) C25_1 0.0233(12) 0.0159(11) 0.0208(11) 0.0044(8) -0.0006(9) 0.0004(9) N25_1 0.0366(13) 0.0166(10) 0.0264(11) 0.0040(8) -0.0008(10) 0.0004(9) O25_1 0.0667(17) 0.0218(10) 0.0344(11) 0.0086(8) -0.0149(11) 0.0073(10) O26_1 0.0589(15) 0.0168(9) 0.0364(11) -0.0003(8) -0.0076(10) -0.0028(9) C26_1 0.0222(12) 0.0197(12) 0.0168(10) 0.0012(8) -0.0016(9) -0.0012(9) Br3_2 0.03502(15) 0.01443(12) 0.02796(13) -0.00444(9) -0.01281(11) 0.00232(10) Br4_2 0.03003(14) 0.01806(12) 0.02871(13) 0.00798(9) -0.00601(10) 0.00044(10) N11_2 0.0198(10) 0.0163(9) 0.0180(9) -0.0006(7) -0.0050(8) -0.0001(8) C12_2 0.0198(11) 0.0150(11) 0.0185(10) -0.0002(8) -0.0021(9) 0.0012(9) N12_2 0.0329(12) 0.0169(10) 0.0245(11) -0.0004(8) -0.0122(9) 0.0029(9) C13_2 0.0233(12) 0.0132(10) 0.0196(10) -0.0030(8) -0.0049(9) 0.0004(9) C14_2 0.0211(12) 0.0196(12) 0.0181(10) -0.0001(8) -0.0035(9) 0.0019(9) C15_2 0.0206(12) 0.0169(11) 0.0199(11) 0.0045(8) -0.0020(9) 0.0012(9) C16_2 0.0208(12) 0.0131(11) 0.0237(11) 0.0001(8) -0.0007(9) -0.0014(9) C21_2 0.0173(11) 0.0181(11) 0.0160(10) -0.0014(8) 0.0000(9) -0.0012(9) C27_2 0.0174(11) 0.0205(12) 0.0175(10) -0.0017(8) -0.0028(9) -0.0012(9) O21_2 0.0275(10) 0.0221(9) 0.0218(8) -0.0005(7) -0.0084(7) 0.0013(7) O22_2 0.0315(10) 0.0185(9) 0.0235(9) -0.0021(7) -0.0074(8) -0.0025(7) C22_2 0.0197(11) 0.0175(11) 0.0187(10) -0.0022(8) -0.0017(9) -0.0004(9) C23_2 0.0188(11) 0.0205(12) 0.0169(10) 0.0012(8) -0.0016(9) -0.0004(9) N23_2 0.0238(11) 0.0261(11) 0.0190(10) 0.0006(8) -0.0019(8) 0.0033(9) O23_2 0.0527(14) 0.0198(10) 0.0335(11) 0.0001(8) -0.0115(10) 0.0053(9) O24_2 0.0343(11) 0.0404(12) 0.0235(9) 0.0050(8) -0.0123(8) -0.0062(9) C24_2 0.0219(12) 0.0216(12) 0.0175(10) -0.0022(8) -0.0014(9) -0.0047(9) C25_2 0.0258(13) 0.0166(11) 0.0199(11) -0.0023(8) 0.0020(10) -0.0040(9) N25_2 0.0464(15) 0.0196(11) 0.0251(11) -0.0004(8) 0.0000(10) -0.0079(10) O25_2 0.094(2) 0.0230(11) 0.0467(14) -0.0054(10) -0.0283(14) -0.0166(13) O26_2 0.0748(18) 0.0205(11) 0.0393(12) 0.0067(9) -0.0111(12) -0.0059(11) C26_2 0.0221(12) 0.0178(11) 0.0185(10) 0.0007(8) 0.0006(9) -0.0001(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 C13_1 1.890(2) . ? Br2_1 C15_1 1.894(2) . ? N11_1 C12_1 1.345(3) . ? N11_1 C16_1 1.350(3) . ? C12_1 N12_1 1.342(3) . ? C12_1 C13_1 1.419(3) . ? N12_1 H12A_1 0.85(4) . ? N12_1 H12B_1 0.89(4) . ? C13_1 C14_1 1.365(3) . ? C14_1 C15_1 1.391(3) . ? C14_1 H14_1 0.9500 . ? C15_1 C16_1 1.371(3) . ? C16_1 H16_1 0.9500 . ? C21_1 C22_1 1.389(3) . ? C21_1 C26_1 1.396(3) . ? C21_1 C27_1 1.507(3) . ? C27_1 O22_1 1.212(3) . ? C27_1 O21_1 1.311(3) . ? O21_1 H21_1 0.83(3) . ? C22_1 C23_1 1.385(3) . ? C22_1 H22_1 0.9500 . ? C23_1 C24_1 1.386(3) . ? C23_1 N23_1 1.469(3) . ? N23_1 O24_1 1.224(3) . ? N23_1 O23_1 1.224(3) . ? C24_1 C25_1 1.384(3) . ? C24_1 H24_1 0.9500 . ? C25_1 C26_1 1.386(3) . ? C25_1 N25_1 1.476(3) . ? N25_1 O26_1 1.217(3) . ? N25_1 O25_1 1.223(3) . ? C26_1 H26_1 0.9500 . ? Br3_2 C13_2 1.884(2) . ? Br4_2 C15_2 1.892(2) . ? N11_2 C12_2 1.346(3) . ? N11_2 C16_2 1.352(3) . ? N11_2 H21_2 1.35(3) . ? C12_2 N12_2 1.344(3) . ? C12_2 C13_2 1.426(3) . ? N12_2 H12A_2 0.93(4) . ? N12_2 H12B_2 0.94(3) . ? C13_2 C14_2 1.370(3) . ? C14_2 C15_2 1.401(3) . ? C14_2 H14_2 0.9500 . ? C15_2 C16_2 1.371(3) . ? C16_2 H16_2 0.9500 . ? C21_2 C26_2 1.390(3) . ? C21_2 C22_2 1.396(3) . ? C21_2 C27_2 1.509(3) . ? C27_2 O22_2 1.232(3) . ? C27_2 O21_2 1.292(3) . ? O21_2 H21_2 1.19(3) . ? C22_2 C23_2 1.388(3) . ? C22_2 H22_2 0.9500 . ? C23_2 C24_2 1.383(3) . ? C23_2 N23_2 1.462(3) . ? N23_2 O24_2 1.220(3) . ? N23_2 O23_2 1.229(3) . ? C24_2 C25_2 1.379(4) . ? C24_2 H24_2 0.9500 . ? C25_2 C26_2 1.387(3) . ? C25_2 N25_2 1.478(3) . ? N25_2 O25_2 1.214(3) . ? N25_2 O26_2 1.222(3) . ? 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 C12_1 N11_1 C16_1 121.1(2) . . ? N12_1 C12_1 N11_1 117.9(2) . . ? N12_1 C12_1 C13_1 123.6(2) . . ? N11_1 C12_1 C13_1 118.6(2) . . ? C12_1 N12_1 H12A_1 122(2) . . ? C12_1 N12_1 H12B_1 122(2) . . ? H12A_1 N12_1 H12B_1 116(3) . . ? C14_1 C13_1 C12_1 120.6(2) . . ? C14_1 C13_1 Br1_1 118.73(18) . . ? C12_1 C13_1 Br1_1 120.63(18) . . ? C13_1 C14_1 C15_1 118.9(2) . . ? C13_1 C14_1 H14_1 120.6 . . ? C15_1 C14_1 H14_1 120.6 . . ? C16_1 C15_1 C14_1 119.4(2) . . ? C16_1 C15_1 Br2_1 120.79(19) . . ? C14_1 C15_1 Br2_1 119.78(18) . . ? N11_1 C16_1 C15_1 121.4(2) . . ? N11_1 C16_1 H16_1 119.3 . . ? C15_1 C16_1 H16_1 119.3 . . ? C22_1 C21_1 C26_1 120.7(2) . . ? C22_1 C21_1 C27_1 117.9(2) . . ? C26_1 C21_1 C27_1 121.4(2) . . ? O22_1 C27_1 O21_1 125.7(2) . . ? O22_1 C27_1 C21_1 121.9(2) . . ? O21_1 C27_1 C21_1 112.5(2) . . ? C27_1 O21_1 H21_1 111(2) . . ? C23_1 C22_1 C21_1 118.2(2) . . ? C23_1 C22_1 H22_1 120.9 . . ? C21_1 C22_1 H22_1 120.9 . . ? C22_1 C23_1 C24_1 123.3(2) . . ? C22_1 C23_1 N23_1 118.5(2) . . ? C24_1 C23_1 N23_1 118.2(2) . . ? O24_1 N23_1 O23_1 123.8(2) . . ? O24_1 N23_1 C23_1 117.8(2) . . ? O23_1 N23_1 C23_1 118.4(2) . . ? C25_1 C24_1 C23_1 116.4(2) . . ? C25_1 C24_1 H24_1 121.8 . . ? C23_1 C24_1 H24_1 121.8 . . ? C24_1 C25_1 C26_1 123.0(2) . . ? C24_1 C25_1 N25_1 118.1(2) . . ? C26_1 C25_1 N25_1 118.9(2) . . ? O26_1 N25_1 O25_1 124.8(2) . . ? O26_1 N25_1 C25_1 117.9(2) . . ? O25_1 N25_1 C25_1 117.3(2) . . ? C25_1 C26_1 C21_1 118.3(2) . . ? C25_1 C26_1 H26_1 120.8 . . ? C21_1 C26_1 H26_1 120.8 . . ? C12_2 N11_2 C16_2 121.3(2) . . ? C12_2 N11_2 H21_2 123.7(14) . . ? C16_2 N11_2 H21_2 114.8(14) . . ? N12_2 C12_2 N11_2 118.3(2) . . ? N12_2 C12_2 C13_2 122.9(2) . . ? N11_2 C12_2 C13_2 118.7(2) . . ? C12_2 N12_2 H12A_2 118(2) . . ? C12_2 N12_2 H12B_2 120(2) . . ? H12A_2 N12_2 H12B_2 122(3) . . ? C14_2 C13_2 C12_2 120.4(2) . . ? C14_2 C13_2 Br3_2 119.49(18) . . ? C12_2 C13_2 Br3_2 120.09(18) . . ? C13_2 C14_2 C15_2 118.6(2) . . ? C13_2 C14_2 H14_2 120.7 . . ? C15_2 C14_2 H14_2 120.7 . . ? C16_2 C15_2 C14_2 119.7(2) . . ? C16_2 C15_2 Br4_2 120.92(19) . . ? C14_2 C15_2 Br4_2 119.40(18) . . ? N11_2 C16_2 C15_2 121.3(2) . . ? N11_2 C16_2 H16_2 119.4 . . ? C15_2 C16_2 H16_2 119.4 . . ? C26_2 C21_2 C22_2 120.5(2) . . ? C26_2 C21_2 C27_2 120.9(2) . . ? C22_2 C21_2 C27_2 118.5(2) . . ? O22_2 C27_2 O21_2 126.1(2) . . ? O22_2 C27_2 C21_2 120.5(2) . . ? O21_2 C27_2 C21_2 113.4(2) . . ? C27_2 O21_2 H21_2 116.2(16) . . ? C23_2 C22_2 C21_2 118.4(2) . . ? C23_2 C22_2 H22_2 120.8 . . ? C21_2 C22_2 H22_2 120.8 . . ? C24_2 C23_2 C22_2 123.0(2) . . ? C24_2 C23_2 N23_2 118.4(2) . . ? C22_2 C23_2 N23_2 118.6(2) . . ? O24_2 N23_2 O23_2 124.2(2) . . ? O24_2 N23_2 C23_2 118.1(2) . . ? O23_2 N23_2 C23_2 117.7(2) . . ? C25_2 C24_2 C23_2 116.5(2) . . ? C25_2 C24_2 H24_2 121.7 . . ? C23_2 C24_2 H24_2 121.7 . . ? C24_2 C25_2 C26_2 123.4(2) . . ? C24_2 C25_2 N25_2 117.7(2) . . ? C26_2 C25_2 N25_2 118.9(2) . . ? O25_2 N25_2 O26_2 124.6(3) . . ? O25_2 N25_2 C25_2 117.8(2) . . ? O26_2 N25_2 C25_2 117.7(2) . . ? C25_2 C26_2 C21_2 118.2(2) . . ? C25_2 C26_2 H26_2 120.9 . . ? C21_2 C26_2 H26_2 120.9 . . ? 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 N11_1 C12_1 N12_1 179.8(2) . . . . ? C16_1 N11_1 C12_1 C13_1 0.5(4) . . . . ? N12_1 C12_1 C13_1 C14_1 -179.9(3) . . . . ? N11_1 C12_1 C13_1 C14_1 -0.7(4) . . . . ? N12_1 C12_1 C13_1 Br1_1 -0.1(4) . . . . ? N11_1 C12_1 C13_1 Br1_1 179.12(18) . . . . ? C12_1 C13_1 C14_1 C15_1 0.0(4) . . . . ? Br1_1 C13_1 C14_1 C15_1 -179.83(19) . . . . ? C13_1 C14_1 C15_1 C16_1 0.9(4) . . . . ? C13_1 C14_1 C15_1 Br2_1 -178.2(2) . . . . ? C12_1 N11_1 C16_1 C15_1 0.5(4) . . . . ? C14_1 C15_1 C16_1 N11_1 -1.2(4) . . . . ? Br2_1 C15_1 C16_1 N11_1 177.99(19) . . . . ? C22_1 C21_1 C27_1 O22_1 -6.4(4) . . . . ? C26_1 C21_1 C27_1 O22_1 174.9(2) . . . . ? C22_1 C21_1 C27_1 O21_1 172.6(2) . . . . ? C26_1 C21_1 C27_1 O21_1 -6.2(3) . . . . ? C26_1 C21_1 C22_1 C23_1 0.7(4) . . . . ? C27_1 C21_1 C22_1 C23_1 -178.0(2) . . . . ? C21_1 C22_1 C23_1 C24_1 -0.6(4) . . . . ? C21_1 C22_1 C23_1 N23_1 -179.6(2) . . . . ? C22_1 C23_1 N23_1 O24_1 -173.9(2) . . . . ? C24_1 C23_1 N23_1 O24_1 7.1(4) . . . . ? C22_1 C23_1 N23_1 O23_1 7.0(4) . . . . ? C24_1 C23_1 N23_1 O23_1 -172.0(2) . . . . ? C22_1 C23_1 C24_1 C25_1 0.2(4) . . . . ? N23_1 C23_1 C24_1 C25_1 179.1(2) . . . . ? C23_1 C24_1 C25_1 C26_1 0.2(4) . . . . ? C23_1 C24_1 C25_1 N25_1 -179.1(2) . . . . ? C24_1 C25_1 N25_1 O26_1 -176.1(3) . . . . ? C26_1 C25_1 N25_1 O26_1 4.6(4) . . . . ? C24_1 C25_1 N25_1 O25_1 3.9(4) . . . . ? C26_1 C25_1 N25_1 O25_1 -175.4(3) . . . . ? C24_1 C25_1 C26_1 C21_1 -0.1(4) . . . . ? N25_1 C25_1 C26_1 C21_1 179.2(2) . . . . ? C22_1 C21_1 C26_1 C25_1 -0.4(4) . . . . ? C27_1 C21_1 C26_1 C25_1 178.3(2) . . . . ? C16_2 N11_2 C12_2 N12_2 179.7(2) . . . . ? C16_2 N11_2 C12_2 C13_2 0.8(4) . . . . ? N12_2 C12_2 C13_2 C14_2 -178.9(3) . . . . ? N11_2 C12_2 C13_2 C14_2 -0.1(4) . . . . ? N12_2 C12_2 C13_2 Br3_2 0.9(4) . . . . ? N11_2 C12_2 C13_2 Br3_2 179.74(18) . . . . ? C12_2 C13_2 C14_2 C15_2 -0.4(4) . . . . ? Br3_2 C13_2 C14_2 C15_2 179.76(19) . . . . ? C13_2 C14_2 C15_2 C16_2 0.2(4) . . . . ? C13_2 C14_2 C15_2 Br4_2 179.80(19) . . . . ? C12_2 N11_2 C16_2 C15_2 -1.1(4) . . . . ? C14_2 C15_2 C16_2 N11_2 0.5(4) . . . . ? Br4_2 C15_2 C16_2 N11_2 -179.08(19) . . . . ? C26_2 C21_2 C27_2 O22_2 -178.4(2) . . . . ? C22_2 C21_2 C27_2 O22_2 -2.2(4) . . . . ? C26_2 C21_2 C27_2 O21_2 0.4(3) . . . . ? C22_2 C21_2 C27_2 O21_2 176.6(2) . . . . ? C26_2 C21_2 C22_2 C23_2 0.9(4) . . . . ? C27_2 C21_2 C22_2 C23_2 -175.4(2) . . . . ? C21_2 C22_2 C23_2 C24_2 -0.3(4) . . . . ? C21_2 C22_2 C23_2 N23_2 178.5(2) . . . . ? C24_2 C23_2 N23_2 O24_2 9.8(4) . . . . ? C22_2 C23_2 N23_2 O24_2 -169.1(2) . . . . ? C24_2 C23_2 N23_2 O23_2 -169.6(2) . . . . ? C22_2 C23_2 N23_2 O23_2 11.6(4) . . . . ? C22_2 C23_2 C24_2 C25_2 -0.6(4) . . . . ? N23_2 C23_2 C24_2 C25_2 -179.4(2) . . . . ? C23_2 C24_2 C25_2 C26_2 1.0(4) . . . . ? C23_2 C24_2 C25_2 N25_2 179.4(2) . . . . ? C24_2 C25_2 N25_2 O25_2 -0.9(4) . . . . ? C26_2 C25_2 N25_2 O25_2 177.5(3) . . . . ? C24_2 C25_2 N25_2 O26_2 178.4(3) . . . . ? C26_2 C25_2 N25_2 O26_2 -3.2(4) . . . . ? C24_2 C25_2 C26_2 C21_2 -0.5(4) . . . . ? N25_2 C25_2 C26_2 C21_2 -178.8(2) . . . . ? C22_2 C21_2 C26_2 C25_2 -0.5(4) . . . . ? C27_2 C21_2 C26_2 C25_2 175.6(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 O21_1 H21_1 N11_1 0.83(3) 1.76(4) 2.580(3) 170(3) . O21_2 H21_2 N11_2 1.19(3) 1.35(3) 2.538(3) 173(3) . N12_1 H12A_1 O22_1 0.85(4) 2.21(4) 3.030(3) 161(3) . N12_2 H12A_2 O22_2 0.93(4) 2.03(4) 2.946(3) 170(3) . N12_1 H12B_1 O23_2 0.89(4) 2.20(4) 3.034(3) 157(3) . N12_2 H12B_2 O23_1 0.94(3) 2.22(3) 2.958(3) 135(3) 1_656 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 31.51 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.475 _refine_diff_density_min -0.582 _refine_diff_density_rms 0.114 #END data_ar0820m(E13) _database_code_depnum_ccdc_archive 'CCDC 772254' #TrackingRef '- allcifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; AR-1i-13 2-amino-3,5-dibromopyridine, fumaric acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C5 H4 N2 Br2)2 (C4 H4 O4) ; _chemical_formula_sum 'C14 H12 Br4 N4 O4' _chemical_formula_weight 619.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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)/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 14.0298(10) _cell_length_b 3.8527(3) _cell_length_c 17.5918(13) _cell_angle_alpha 90.00 _cell_angle_beta 102.337(3) _cell_angle_gamma 90.00 _cell_volume 928.92(12) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9480 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 36.11 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.216 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 8.693 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3368 _exptl_absorpt_correction_T_max 0.5431 _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19668 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 33.72 _reflns_number_total 3635 _reflns_number_gt 3187 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0250P)^2^+0.4000P] 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 3635 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0211 _refine_ls_wR_factor_ref 0.0521 _refine_ls_wR_factor_gt 0.0501 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 Br1 Br -0.043775(7) 0.93494(3) 0.601847(6) 0.01667(2) Uani 1 1 d . . . Br2 Br 0.268061(7) 0.90703(3) 0.865653(5) 0.01549(2) Uani 1 1 d . . . N11 N 0.24018(6) 0.5842(2) 0.63863(5) 0.01475(17) Uani 1 1 d . . . C12 C 0.27799(7) 0.6526(3) 0.71422(6) 0.01362(18) Uani 1 1 d . . . N12 N 0.37093(7) 0.5611(3) 0.74308(5) 0.01899(19) Uani 1 1 d . . . H12A H 0.4012(11) 0.472(4) 0.7135(9) 0.023 Uiso 1 1 d . . . H12B H 0.3976(10) 0.613(4) 0.7873(9) 0.023 Uiso 1 1 d . . . C13 C 0.21786(7) 0.8108(2) 0.75964(5) 0.01320(18) Uani 1 1 d . . . C14 C 0.12293(7) 0.8961(2) 0.72703(6) 0.01371(19) Uani 1 1 d . . . H14 H 0.0828 1.0042 0.7573 0.016 Uiso 1 1 calc R . . C15 C 0.08637(7) 0.8207(3) 0.64830(6) 0.01356(18) Uani 1 1 d . . . C16 C 0.14676(7) 0.6646(3) 0.60646(6) 0.01411(19) Uani 1 1 d . . . H16 H 0.1219 0.6117 0.5532 0.017 Uiso 1 1 calc R . . C21 C 0.41575(7) 0.2176(3) 0.55859(6) 0.01468(19) Uani 1 1 d . . . O21 O 0.32880(5) 0.3494(2) 0.53462(4) 0.02116(17) Uani 1 1 d . . . H21 H 0.3073(11) 0.421(4) 0.5728(9) 0.025 Uiso 1 1 d . . . O22 O 0.45866(6) 0.2002(2) 0.62681(4) 0.02294(18) Uani 1 1 d . . . C22 C 0.45851(7) 0.0873(2) 0.49351(6) 0.0149(2) Uani 1 1 d . . . H22 H 0.4254 0.1307 0.4414 0.018 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.01188(4) 0.01981(4) 0.01828(4) 0.00196(3) 0.00315(3) 0.00360(3) Br2 0.01555(4) 0.01837(4) 0.01259(4) -0.00370(3) 0.00311(3) -0.00150(3) N11 0.0120(3) 0.0197(4) 0.0130(3) -0.0014(3) 0.0035(3) 0.0025(3) C12 0.0121(4) 0.0152(4) 0.0137(4) 0.0001(3) 0.0031(3) 0.0003(3) N12 0.0126(3) 0.0301(5) 0.0140(4) -0.0043(3) 0.0022(3) 0.0043(3) C13 0.0140(4) 0.0132(4) 0.0126(4) -0.0019(3) 0.0034(3) -0.0009(3) C14 0.0131(4) 0.0144(4) 0.0151(4) -0.0009(3) 0.0062(3) 0.0001(3) C15 0.0109(3) 0.0144(4) 0.0157(4) 0.0008(3) 0.0036(3) 0.0015(3) C16 0.0120(4) 0.0178(4) 0.0126(4) -0.0001(3) 0.0028(3) 0.0020(3) C21 0.0123(4) 0.0178(4) 0.0145(4) 0.0002(3) 0.0042(3) 0.0028(3) O21 0.0151(3) 0.0356(4) 0.0132(3) -0.0017(3) 0.0038(3) 0.0120(3) O22 0.0181(3) 0.0378(4) 0.0124(3) -0.0019(3) 0.0020(3) 0.0112(3) C22 0.0127(4) 0.0198(4) 0.0123(4) -0.0009(3) 0.0032(3) 0.0029(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C15 1.8862(9) . ? Br2 C13 1.8842(9) . ? N11 C16 1.3479(12) . ? N11 C12 1.3482(12) . ? C12 N12 1.3413(13) . ? C12 C13 1.4177(14) . ? N12 H12A 0.814(16) . ? N12 H12B 0.812(15) . ? C13 C14 1.3727(13) . ? C14 C15 1.4008(13) . ? C14 H14 0.9500 . ? C15 C16 1.3738(14) . ? C16 H16 0.9500 . ? C21 O22 1.2241(12) . ? C21 O21 1.3054(12) . ? C21 C22 1.4888(14) . ? O21 H21 0.839(16) . ? C22 C22 1.3213(19) 3_656 ? C22 H22 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 C16 N11 C12 120.77(9) . . ? N12 C12 N11 117.90(9) . . ? N12 C12 C13 123.16(9) . . ? N11 C12 C13 118.93(8) . . ? C12 N12 H12A 117.8(10) . . ? C12 N12 H12B 120.6(11) . . ? H12A N12 H12B 121.2(15) . . ? C14 C13 C12 120.56(9) . . ? C14 C13 Br2 119.38(7) . . ? C12 C13 Br2 120.05(7) . . ? C13 C14 C15 118.76(9) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? C16 C15 C14 118.88(9) . . ? C16 C15 Br1 121.39(7) . . ? C14 C15 Br1 119.74(7) . . ? N11 C16 C15 122.09(9) . . ? N11 C16 H16 119.0 . . ? C15 C16 H16 119.0 . . ? O22 C21 O21 124.61(10) . . ? O22 C21 C22 122.75(9) . . ? O21 C21 C22 112.65(8) . . ? C21 O21 H21 109.9(10) . . ? C22 C22 C21 121.57(11) 3_656 . ? C22 C22 H22 119.2 3_656 . ? C21 C22 H22 119.2 . . ? 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 C16 N11 C12 N12 178.93(9) . . . . ? C16 N11 C12 C13 0.01(14) . . . . ? N12 C12 C13 C14 -179.45(10) . . . . ? N11 C12 C13 C14 -0.59(15) . . . . ? N12 C12 C13 Br2 0.70(14) . . . . ? N11 C12 C13 Br2 179.56(7) . . . . ? C12 C13 C14 C15 0.62(15) . . . . ? Br2 C13 C14 C15 -179.52(7) . . . . ? C13 C14 C15 C16 -0.09(14) . . . . ? C13 C14 C15 Br1 -179.98(7) . . . . ? C12 N11 C16 C15 0.53(15) . . . . ? C14 C15 C16 N11 -0.49(15) . . . . ? Br1 C15 C16 N11 179.39(8) . . . . ? O22 C21 C22 C22 7.06(19) . . . 3_656 ? O21 C21 C22 C22 -172.88(13) . . . 3_656 ? 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 0.839(16) 1.758(17) 2.5855(12) 168.3(15) . N12 H12A O22 0.814(16) 2.145(16) 2.9510(13) 170.7(14) . N12 H12B O22 0.812(15) 2.272(14) 2.9839(11) 146.5(14) 2_656 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 33.72 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.688 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.094 #END data_ar0728m(F14) _database_code_depnum_ccdc_archive 'CCDC 772255' #TrackingRef '- allcifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (N-5-bromo-2-pyridyl)-acetamide)2, fumaric acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C7 H7 N2 O Br)2 (C4 H6 O4) ; _chemical_formula_sum 'C18 H20 Br2 N4 O6' _chemical_formula_weight 548.20 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' 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 4.9878(3) _cell_length_b 9.9931(7) _cell_length_c 11.4625(8) _cell_angle_alpha 113.250(5) _cell_angle_beta 92.103(5) _cell_angle_gamma 93.352(5) _cell_volume 522.92(6) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1812 _cell_measurement_theta_min 3.88 _cell_measurement_theta_max 22.23 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.741 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 274 _exptl_absorpt_coefficient_mu 3.919 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3561 _exptl_absorpt_correction_T_max 0.6906 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8216 _diffrn_reflns_av_R_equivalents 0.0599 _diffrn_reflns_av_sigmaI/netI 0.0656 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 27.12 _reflns_number_total 2184 _reflns_number_gt 1508 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2184 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0840 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _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 0.78851(9) 0.74834(5) 0.19608(4) 0.04392(19) Uani 1 1 d . . . N11 N 0.3377(6) 0.4022(3) 0.2153(3) 0.0241(7) Uani 1 1 d . . . C12 C 0.4722(7) 0.3743(4) 0.3052(4) 0.0252(8) Uani 1 1 d . . . N12 N 0.3564(6) 0.2573(3) 0.3270(3) 0.0259(8) Uani 1 1 d . . . H12 H 0.225(8) 0.218(4) 0.287(4) 0.031 Uiso 1 1 d . . . C13 C 0.7087(7) 0.4576(4) 0.3700(3) 0.0264(9) Uani 1 1 d . . . H13 H 0.8010 0.4365 0.4340 0.032 Uiso 1 1 calc R . . C14 C 0.8040(7) 0.5704(4) 0.3389(3) 0.0263(9) Uani 1 1 d . . . H14 H 0.9633 0.6288 0.3815 0.032 Uiso 1 1 calc R . . C15 C 0.6666(7) 0.5980(4) 0.2454(4) 0.0277(9) Uani 1 1 d . . . C16 C 0.4315(7) 0.5117(4) 0.1859(4) 0.0273(9) Uani 1 1 d . . . H16 H 0.3351 0.5316 0.1223 0.033 Uiso 1 1 calc R . . C17 C 0.4523(7) 0.1938(4) 0.4050(4) 0.0266(9) Uani 1 1 d . . . O17 O 0.6655(5) 0.2346(3) 0.4691(3) 0.0355(7) Uani 1 1 d . . . C18 C 0.2723(8) 0.0682(4) 0.4044(4) 0.0354(10) Uani 1 1 d . . . H18A H 0.2624 0.0742 0.4915 0.053 Uiso 1 1 calc R . . H18B H 0.3449 -0.0239 0.3514 0.053 Uiso 1 1 calc R . . H18C H 0.0918 0.0721 0.3697 0.053 Uiso 1 1 calc R . . C21 C -0.2002(7) 0.1421(4) 0.0790(3) 0.0223(8) Uani 1 1 d . . . O21 O -0.1108(5) 0.2611(3) 0.0656(3) 0.0291(7) Uani 1 1 d . . . H21 H 0.008(8) 0.295(5) 0.109(4) 0.035 Uiso 1 1 d . . . O22 O -0.0985(5) 0.0972(3) 0.1530(2) 0.0300(6) Uani 1 1 d . . . C22 C -0.4464(7) 0.0672(4) -0.0083(3) 0.0262(9) Uani 1 1 d . . . H22A H -0.5885 0.1364 0.0087 0.031 Uiso 1 1 calc R . . H22B H -0.4003 0.0399 -0.0977 0.031 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0419(3) 0.0453(3) 0.0443(3) 0.0217(2) -0.01249(19) -0.0170(2) N11 0.0183(15) 0.0256(16) 0.0208(17) 0.0022(14) -0.0058(13) 0.0000(13) C12 0.0190(18) 0.0249(19) 0.024(2) 0.0014(17) -0.0021(16) 0.0033(15) N12 0.0190(17) 0.0248(16) 0.0271(18) 0.0049(14) -0.0092(14) -0.0045(13) C13 0.0205(19) 0.028(2) 0.020(2) -0.0005(17) -0.0067(16) -0.0009(16) C14 0.0201(18) 0.030(2) 0.018(2) -0.0010(17) -0.0019(15) -0.0019(16) C15 0.0229(19) 0.029(2) 0.025(2) 0.0044(18) 0.0029(16) 0.0014(16) C16 0.025(2) 0.028(2) 0.022(2) 0.0032(17) -0.0035(16) 0.0019(16) C17 0.0241(19) 0.0252(19) 0.025(2) 0.0048(17) -0.0034(16) 0.0038(16) O17 0.0260(14) 0.0384(15) 0.0366(17) 0.0112(13) -0.0147(12) -0.0030(12) C18 0.033(2) 0.033(2) 0.035(2) 0.011(2) -0.0124(19) -0.0071(18) C21 0.0180(18) 0.025(2) 0.0168(19) 0.0011(17) 0.0003(15) -0.0013(16) O21 0.0229(14) 0.0308(15) 0.0264(15) 0.0060(12) -0.0105(11) -0.0076(12) O22 0.0261(14) 0.0299(14) 0.0294(15) 0.0095(13) -0.0136(12) -0.0066(12) C22 0.0200(18) 0.0292(19) 0.023(2) 0.0050(17) -0.0084(16) -0.0044(16) _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 C15 1.880(4) . ? N11 C16 1.331(4) . ? N11 C12 1.337(4) . ? C12 N12 1.388(5) . ? C12 C13 1.403(4) . ? N12 C17 1.373(5) . ? N12 H12 0.77(4) . ? C13 C14 1.375(5) . ? C13 H13 0.9500 . ? C14 C15 1.377(5) . ? C14 H14 0.9500 . ? C15 C16 1.394(5) . ? C16 H16 0.9500 . ? C17 O17 1.221(4) . ? C17 C18 1.497(5) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C21 O22 1.214(4) . ? C21 O21 1.313(4) . ? C21 C22 1.510(4) . ? O21 H21 0.73(4) . ? C22 C22 1.501(7) 2_455 ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 119.1(3) . . ? N11 C12 N12 113.9(3) . . ? N11 C12 C13 121.9(3) . . ? N12 C12 C13 124.2(3) . . ? C17 N12 C12 128.7(3) . . ? C17 N12 H12 114(3) . . ? C12 N12 H12 117(3) . . ? C14 C13 C12 118.5(3) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C13 C14 C15 119.4(3) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C14 C15 C16 118.9(3) . . ? C14 C15 Br1 121.7(3) . . ? C16 C15 Br1 119.4(3) . . ? N11 C16 C15 122.1(3) . . ? N11 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? O17 C17 N12 123.6(3) . . ? O17 C17 C18 122.5(3) . . ? N12 C17 C18 113.9(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O22 C21 O21 124.3(3) . . ? O22 C21 C22 123.6(3) . . ? O21 C21 C22 112.1(3) . . ? C21 O21 H21 110(3) . . ? C22 C22 C21 112.5(4) 2_455 . ? C22 C22 H22A 109.1 2_455 . ? C21 C22 H22A 109.1 . . ? C22 C22 H22B 109.1 2_455 . ? C21 C22 H22B 109.1 . . ? H22A C22 H22B 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 N12 -179.6(3) . . . . ? C16 N11 C12 C13 0.4(5) . . . . ? N11 C12 N12 C17 174.7(3) . . . . ? C13 C12 N12 C17 -5.2(6) . . . . ? N11 C12 C13 C14 -0.4(6) . . . . ? N12 C12 C13 C14 179.6(3) . . . . ? C12 C13 C14 C15 -0.2(5) . . . . ? C13 C14 C15 C16 0.9(5) . . . . ? C13 C14 C15 Br1 -178.9(3) . . . . ? C12 N11 C16 C15 0.3(5) . . . . ? C14 C15 C16 N11 -0.9(6) . . . . ? Br1 C15 C16 N11 178.9(3) . . . . ? C12 N12 C17 O17 -0.1(6) . . . . ? C12 N12 C17 C18 -179.8(4) . . . . ? O22 C21 C22 C22 1.0(6) . . . 2_455 ? O21 C21 C22 C22 -178.8(4) . . . 2_455 ? 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 0.73(4) 1.99(4) 2.716(4) 174(5) . N12 H12 O22 0.77(4) 2.13(4) 2.900(4) 171(4) . _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.772 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.102 #END