# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global #TrackingRef '- X-ray crystal structural data of 4c.cif' _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author_name 'Prof. Yongping Yu' _publ_contact_author_address ; Institute of Materia Medica, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, P. R. China ; _publ_contact_author_email yyu@zju.edu.cn _publ_contact_author_fax '86 0571 88208452' _publ_contact_author_phone '86 0571 88208452' #============================================================================ # TITLE AND AUTHOR LIST _publ_section_title ; "One-Pot" Multicomponent Approach to Polysubstituted 4-Aminopyridines ; loop_ _publ_author_name _publ_author_address 'Jiaan Shao.' ; Institute of Materia Medica, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, P. R. China ; 'Wanwan Yu.' ; Institute of Materia Medica, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, P. R. China ; 'Zhanying Shao.' ; Institute of Materia Medica, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, P. R. China ; 'Yongping Yu.' ; Institute of Materia Medica, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, P. R. China ; #================================================================= data_4c _database_code_depnum_ccdc_archive 'CCDC 862844' #TrackingRef '- X-ray crystal structural data of 4c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H20 Br N3 O' _chemical_formula_sum 'C26 H20 Br N3 O' _chemical_formula_weight 470.36 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9984(6) _cell_length_b 10.6788(7) _cell_length_c 12.6094(9) _cell_angle_alpha 68.7577(18) _cell_angle_beta 86.7228(18) _cell_angle_gamma 66.0269(14) _cell_volume 1140.17(13) _cell_formula_units_Z 2 _cell_measurement_temperature 296(1) _cell_measurement_reflns_used 5885 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 27.4 _exptl_crystal_description chunk _exptl_crystal_colour yellow _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 1.825 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4916 _exptl_absorpt_correction_T_max 0.7196 _exptl_absorpt_process_details 'Higashi, T. (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rolling anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID/ZJUG' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9008 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3964 _reflns_number_gt 2266 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku,2006)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku,2006)' _computing_data_reduction 'CrystalStructure (Rigaku,2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep3 for windows (Farrugia,1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0298P)^2^+1.5931P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0215(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3964 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0940 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1233 _refine_ls_wR_factor_gt 0.0834 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 0.43702(8) 0.78032(7) -0.13089(4) 0.1076(3) Uani 1 1 d . . . O1 O 0.1444(4) 0.2357(4) 1.0522(3) 0.1020(12) Uani 1 1 d . . . N1 N 0.2859(3) 0.5297(3) 0.5534(2) 0.0516(8) Uani 1 1 d . . . N2 N 0.3764(4) 0.8061(4) 0.3837(3) 0.0717(10) Uani 1 1 d . . . N3 N 0.2742(4) 0.3277(4) 0.3278(3) 0.0707(10) Uani 1 1 d . . . H3A H 0.2534 0.2521 0.3505 0.085 Uiso 1 1 calc R . . H3B H 0.2925 0.3622 0.2583 0.085 Uiso 1 1 calc R . . C1 C 0.3497(4) 0.7052(5) 0.4104(3) 0.0572(10) Uani 1 1 d . . . C2 C 0.3137(4) 0.5771(4) 0.4438(3) 0.0499(9) Uani 1 1 d . . . C3 C 0.3111(4) 0.5178(4) 0.3640(3) 0.0518(10) Uani 1 1 d . . . C4 C 0.2782(4) 0.3928(4) 0.4019(3) 0.0535(10) Uani 1 1 d . . . C5 C 0.2489(4) 0.3390(4) 0.5162(3) 0.0485(9) Uani 1 1 d . . . C6 C 0.2545(4) 0.4102(4) 0.5880(3) 0.0471(9) Uani 1 1 d . . . C7 C 0.3415(4) 0.5804(4) 0.2441(3) 0.0544(10) Uani 1 1 d . . . C8 C 0.2288(5) 0.6648(6) 0.1566(4) 0.0857(16) Uani 1 1 d . . . H8 H 0.1322 0.6828 0.1726 0.103 Uiso 1 1 calc R . . C9 C 0.2577(6) 0.7231(6) 0.0454(4) 0.0976(17) Uani 1 1 d . . . H9 H 0.1807 0.7803 -0.0130 0.117 Uiso 1 1 calc R . . C10 C 0.3988(6) 0.6971(5) 0.0208(4) 0.0692(12) Uani 1 1 d . . . C11 C 0.5124(5) 0.6125(5) 0.1063(4) 0.0731(13) Uani 1 1 d . . . H11 H 0.6088 0.5939 0.0896 0.088 Uiso 1 1 calc R . . C12 C 0.4831(5) 0.5548(5) 0.2175(3) 0.0660(12) Uani 1 1 d . . . H12 H 0.5606 0.4975 0.2755 0.079 Uiso 1 1 calc R . . C13 C 0.2108(4) 0.2089(4) 0.5561(3) 0.0512(9) Uani 1 1 d . . . C14 C 0.0744(4) 0.2198(4) 0.5904(4) 0.0648(12) Uani 1 1 d . . . H14 H 0.0038 0.3102 0.5888 0.078 Uiso 1 1 calc R . . C15 C 0.0410(5) 0.0987(5) 0.6269(4) 0.0773(14) Uani 1 1 d . . . H15 H -0.0512 0.1082 0.6508 0.093 Uiso 1 1 calc R . . C16 C 0.1434(5) -0.0381(5) 0.6284(4) 0.0680(12) Uani 1 1 d . . . C17 C 0.2793(5) -0.0486(5) 0.5950(4) 0.0693(12) Uani 1 1 d . . . H17 H 0.3496 -0.1389 0.5959 0.083 Uiso 1 1 calc R . . C18 C 0.3138(5) 0.0718(5) 0.5600(4) 0.0658(12) Uani 1 1 d . . . H18 H 0.4072 0.0612 0.5387 0.079 Uiso 1 1 calc R . . C19 C 0.1055(6) -0.1700(5) 0.6688(5) 0.0998(18) Uani 1 1 d . . . H19A H 0.1672 -0.2409 0.6372 0.150 Uiso 1 1 calc R . . H19B H 0.0042 -0.1389 0.6439 0.150 Uiso 1 1 calc R . . H19C H 0.1210 -0.2142 0.7508 0.150 Uiso 1 1 calc R . . C20 C 0.2270(4) 0.3595(4) 0.7102(3) 0.0520(10) Uani 1 1 d . . . C21 C 0.1261(4) 0.4590(4) 0.7545(3) 0.0582(10) Uani 1 1 d . . . H21 H 0.0748 0.5571 0.7066 0.070 Uiso 1 1 calc R . . C22 C 0.1015(5) 0.4139(5) 0.8679(4) 0.0679(12) Uani 1 1 d . . . H22 H 0.0338 0.4815 0.8960 0.081 Uiso 1 1 calc R . . C23 C 0.1773(5) 0.2680(5) 0.9406(4) 0.0702(12) Uani 1 1 d . . . C24 C 0.2768(5) 0.1698(5) 0.8988(4) 0.0720(13) Uani 1 1 d . . . H24 H 0.3286 0.0720 0.9471 0.086 Uiso 1 1 calc R . . C25 C 0.3006(5) 0.2155(5) 0.7849(3) 0.0650(11) Uani 1 1 d . . . H25 H 0.3685 0.1471 0.7577 0.078 Uiso 1 1 calc R . . C26 C 0.2260(8) 0.0880(7) 1.1310(5) 0.129(2) Uani 1 1 d . . . H26A H 0.2000 0.0211 1.1117 0.193 Uiso 1 1 calc R . . H26B H 0.2031 0.0816 1.2073 0.193 Uiso 1 1 calc R . . H26C H 0.3294 0.0622 1.1269 0.193 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 0.1805(7) 0.1009(5) 0.0491(3) -0.0209(3) 0.0344(3) -0.0746(5) O1 0.128(3) 0.105(3) 0.055(2) -0.017(2) 0.038(2) -0.045(2) N1 0.056(2) 0.0531(19) 0.0422(18) -0.0137(15) 0.0101(15) -0.0229(16) N2 0.086(3) 0.068(2) 0.065(2) -0.020(2) 0.018(2) -0.041(2) N3 0.101(3) 0.074(2) 0.056(2) -0.0318(19) 0.025(2) -0.050(2) C1 0.056(3) 0.061(3) 0.046(2) -0.013(2) 0.0111(19) -0.023(2) C2 0.049(2) 0.050(2) 0.046(2) -0.0139(19) 0.0096(17) -0.0208(18) C3 0.053(2) 0.056(2) 0.044(2) -0.0149(19) 0.0104(18) -0.0246(19) C4 0.054(2) 0.055(2) 0.053(2) -0.023(2) 0.0117(18) -0.0226(19) C5 0.052(2) 0.048(2) 0.043(2) -0.0168(18) 0.0121(17) -0.0195(18) C6 0.047(2) 0.047(2) 0.042(2) -0.0156(18) 0.0118(17) -0.0155(17) C7 0.060(3) 0.063(3) 0.039(2) -0.0126(19) 0.0060(19) -0.029(2) C8 0.066(3) 0.117(4) 0.051(3) -0.006(3) 0.002(2) -0.036(3) C9 0.093(4) 0.112(4) 0.055(3) -0.001(3) -0.012(3) -0.034(3) C10 0.095(4) 0.070(3) 0.052(3) -0.021(2) 0.012(3) -0.045(3) C11 0.075(3) 0.092(3) 0.062(3) -0.027(3) 0.026(3) -0.048(3) C12 0.064(3) 0.082(3) 0.044(2) -0.012(2) 0.007(2) -0.034(2) C13 0.056(2) 0.051(2) 0.046(2) -0.0177(18) 0.0118(18) -0.0217(19) C14 0.055(3) 0.050(2) 0.083(3) -0.021(2) 0.013(2) -0.019(2) C15 0.061(3) 0.066(3) 0.101(4) -0.018(3) 0.009(3) -0.034(2) C16 0.086(3) 0.053(3) 0.065(3) -0.017(2) 0.001(2) -0.033(2) C17 0.094(3) 0.047(2) 0.058(3) -0.019(2) 0.020(2) -0.022(2) C18 0.069(3) 0.058(3) 0.064(3) -0.024(2) 0.028(2) -0.021(2) C19 0.125(5) 0.070(3) 0.119(5) -0.031(3) 0.012(4) -0.058(3) C20 0.058(2) 0.048(2) 0.048(2) -0.0145(19) 0.0151(19) -0.0241(19) C21 0.065(3) 0.054(2) 0.056(3) -0.020(2) 0.021(2) -0.027(2) C22 0.076(3) 0.069(3) 0.061(3) -0.029(2) 0.028(2) -0.031(2) C23 0.090(3) 0.075(3) 0.048(3) -0.018(2) 0.026(2) -0.044(3) C24 0.096(3) 0.057(3) 0.053(3) -0.013(2) 0.016(2) -0.029(2) C25 0.078(3) 0.055(3) 0.051(3) -0.017(2) 0.013(2) -0.020(2) C26 0.179(7) 0.114(5) 0.057(3) 0.000(3) 0.035(4) -0.056(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C10 1.885(4) . ? O1 C23 1.376(5) . ? O1 C26 1.433(6) . ? N1 C2 1.344(4) . ? N1 C6 1.351(4) . ? N2 C1 1.143(5) . ? N3 C4 1.361(5) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? C1 C2 1.464(6) . ? C2 C3 1.376(5) . ? C3 C4 1.412(5) . ? C3 C7 1.485(5) . ? C4 C5 1.409(5) . ? C5 C6 1.393(5) . ? C5 C13 1.493(5) . ? C6 C20 1.487(5) . ? C7 C12 1.375(5) . ? C7 C8 1.377(6) . ? C8 C9 1.381(6) . ? C8 H8 0.9300 . ? C9 C10 1.363(7) . ? C9 H9 0.9300 . ? C10 C11 1.367(6) . ? C11 C12 1.380(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.379(5) . ? C13 C18 1.391(5) . ? C14 C15 1.377(6) . ? C14 H14 0.9300 . ? C15 C16 1.396(6) . ? C15 H15 0.9300 . ? C16 C17 1.372(6) . ? C16 C19 1.510(6) . ? C17 C18 1.378(6) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C25 1.380(5) . ? C20 C21 1.398(5) . ? C21 C22 1.377(5) . ? C21 H21 0.9300 . ? C22 C23 1.388(6) . ? C22 H22 0.9300 . ? C23 C24 1.364(6) . ? C24 C25 1.381(5) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? 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 C23 O1 C26 116.8(4) . . ? C2 N1 C6 115.9(3) . . ? C4 N3 H3A 120.0 . . ? C4 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? N2 C1 C2 179.3(5) . . ? N1 C2 C3 126.7(3) . . ? N1 C2 C1 114.1(3) . . ? C3 C2 C1 119.2(3) . . ? C2 C3 C4 116.5(3) . . ? C2 C3 C7 122.3(3) . . ? C4 C3 C7 121.2(4) . . ? N3 C4 C5 121.4(4) . . ? N3 C4 C3 119.9(3) . . ? C5 C4 C3 118.8(4) . . ? C6 C5 C4 118.8(3) . . ? C6 C5 C13 122.2(3) . . ? C4 C5 C13 119.0(3) . . ? N1 C6 C5 123.3(3) . . ? N1 C6 C20 114.4(3) . . ? C5 C6 C20 122.3(3) . . ? C12 C7 C8 118.3(4) . . ? C12 C7 C3 120.8(4) . . ? C8 C7 C3 120.9(4) . . ? C7 C8 C9 120.6(4) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C8 120.2(5) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 120.0(4) . . ? C9 C10 Br1 119.9(4) . . ? C11 C10 Br1 120.0(4) . . ? C10 C11 C12 119.6(4) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C7 C12 C11 121.2(4) . . ? C7 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C14 C13 C18 117.9(4) . . ? C14 C13 C5 121.7(3) . . ? C18 C13 C5 120.3(3) . . ? C15 C14 C13 121.0(4) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C16 121.0(4) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C17 C16 C15 117.8(4) . . ? C17 C16 C19 121.7(4) . . ? C15 C16 C19 120.4(4) . . ? C16 C17 C18 121.3(4) . . ? C16 C17 H17 119.3 . . ? C18 C17 H17 119.3 . . ? C17 C18 C13 120.9(4) . . ? C17 C18 H18 119.5 . . ? C13 C18 H18 119.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 117.2(4) . . ? C25 C20 C6 122.4(3) . . ? C21 C20 C6 120.4(3) . . ? C22 C21 C20 121.0(4) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C21 C22 C23 120.3(4) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C24 C23 O1 125.3(4) . . ? C24 C23 C22 119.4(4) . . ? O1 C23 C22 115.3(4) . . ? C23 C24 C25 120.0(4) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C24 C25 C20 122.1(4) . . ? C24 C25 H25 118.9 . . ? C20 C25 H25 118.9 . . ? O1 C26 H26A 109.5 . . ? O1 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O1 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 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 C6 N1 C2 C3 1.0(6) . . . . ? C6 N1 C2 C1 -179.0(3) . . . . ? N1 C2 C3 C4 -1.1(6) . . . . ? C1 C2 C3 C4 178.9(3) . . . . ? N1 C2 C3 C7 179.1(4) . . . . ? C1 C2 C3 C7 -0.9(6) . . . . ? C2 C3 C4 N3 -179.8(3) . . . . ? C7 C3 C4 N3 0.1(6) . . . . ? C2 C3 C4 C5 0.8(5) . . . . ? C7 C3 C4 C5 -179.4(4) . . . . ? N3 C4 C5 C6 -179.9(3) . . . . ? C3 C4 C5 C6 -0.5(5) . . . . ? N3 C4 C5 C13 -0.8(6) . . . . ? C3 C4 C5 C13 178.7(3) . . . . ? C2 N1 C6 C5 -0.7(5) . . . . ? C2 N1 C6 C20 179.0(3) . . . . ? C4 C5 C6 N1 0.5(5) . . . . ? C13 C5 C6 N1 -178.7(3) . . . . ? C4 C5 C6 C20 -179.2(3) . . . . ? C13 C5 C6 C20 1.7(5) . . . . ? C2 C3 C7 C12 76.9(5) . . . . ? C4 C3 C7 C12 -102.9(5) . . . . ? C2 C3 C7 C8 -103.4(5) . . . . ? C4 C3 C7 C8 76.8(6) . . . . ? C12 C7 C8 C9 -0.6(8) . . . . ? C3 C7 C8 C9 179.8(5) . . . . ? C7 C8 C9 C10 0.3(9) . . . . ? C8 C9 C10 C11 0.3(8) . . . . ? C8 C9 C10 Br1 -178.7(4) . . . . ? C9 C10 C11 C12 -0.5(7) . . . . ? Br1 C10 C11 C12 178.5(3) . . . . ? C8 C7 C12 C11 0.3(7) . . . . ? C3 C7 C12 C11 180.0(4) . . . . ? C10 C11 C12 C7 0.2(7) . . . . ? C6 C5 C13 C14 63.8(5) . . . . ? C4 C5 C13 C14 -115.3(4) . . . . ? C6 C5 C13 C18 -115.9(4) . . . . ? C4 C5 C13 C18 64.9(5) . . . . ? C18 C13 C14 C15 -0.3(7) . . . . ? C5 C13 C14 C15 180.0(4) . . . . ? C13 C14 C15 C16 -1.1(7) . . . . ? C14 C15 C16 C17 1.5(7) . . . . ? C14 C15 C16 C19 179.9(5) . . . . ? C15 C16 C17 C18 -0.5(7) . . . . ? C19 C16 C17 C18 -179.0(5) . . . . ? C16 C17 C18 C13 -0.8(7) . . . . ? C14 C13 C18 C17 1.2(6) . . . . ? C5 C13 C18 C17 -179.0(4) . . . . ? N1 C6 C20 C25 -127.2(4) . . . . ? C5 C6 C20 C25 52.5(6) . . . . ? N1 C6 C20 C21 51.3(5) . . . . ? C5 C6 C20 C21 -129.1(4) . . . . ? C25 C20 C21 C22 -0.3(6) . . . . ? C6 C20 C21 C22 -178.9(4) . . . . ? C20 C21 C22 C23 0.1(7) . . . . ? C26 O1 C23 C24 2.5(8) . . . . ? C26 O1 C23 C22 -176.9(5) . . . . ? C21 C22 C23 C24 0.3(7) . . . . ? C21 C22 C23 O1 179.7(4) . . . . ? O1 C23 C24 C25 -179.8(4) . . . . ? C22 C23 C24 C25 -0.5(7) . . . . ? C23 C24 C25 C20 0.3(7) . . . . ? C21 C20 C25 C24 0.1(7) . . . . ? C6 C20 C25 C24 178.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.340 _refine_diff_density_min -0.638 _refine_diff_density_rms 0.064 # Attachment '- X-ray crystal structural data of 4h.cif' # Electronic Supplementary Material (ESI) for Chemical Communications # This journal is The Royal Society of Chemistry 2012 data_4h _database_code_depnum_ccdc_archive 'CCDC 862845' #TrackingRef '- X-ray crystal structural data of 4h.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H17 Br N4, C H4 O' _chemical_formula_sum 'C25 H21 Br N4 O' _chemical_formula_weight 473.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' 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 14.3833(8) _cell_length_b 11.4881(6) _cell_length_c 14.3173(8) _cell_angle_alpha 90.00 _cell_angle_beta 107.727(2) _cell_angle_gamma 90.00 _cell_volume 2253.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(1) _cell_measurement_reflns_used 8519 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 27.4 _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 1.848 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4980 _exptl_absorpt_correction_T_max 0.7160 _exptl_absorpt_process_details 'Higashi, T. (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rolling anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID/ZJUG' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14146 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4400 _reflns_number_gt 2434 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku,2006)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku,2006)' _computing_data_reduction 'CrystalStructure (Rigaku,2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep3 for windows (Farrugia,1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0877P)^2^+1.9825P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4400 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1029 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1741 _refine_ls_wR_factor_gt 0.1167 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.005 _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 0.86710(4) 0.94776(5) 0.45168(5) 0.0809(3) Uani 1 1 d . . . N1 N 0.4317(2) 0.5908(3) 0.5955(2) 0.0430(8) Uani 1 1 d . . . N2 N 0.6803(3) 0.5937(4) 0.6821(3) 0.0646(11) Uani 1 1 d . . . N3 N 0.3878(3) 0.8123(3) 0.3548(3) 0.0538(10) Uani 1 1 d . . . H3A H 0.4368 0.8473 0.3449 0.065 Uiso 1 1 calc R . . H3B H 0.3299 0.8241 0.3159 0.065 Uiso 1 1 calc R . . N4 N 0.2562(3) 0.5869(3) 0.6539(3) 0.0561(10) Uani 1 1 d . . . C1 C 0.6030(3) 0.6167(4) 0.6352(3) 0.0464(10) Uani 1 1 d . . . C2 C 0.5055(3) 0.6443(3) 0.5727(3) 0.0412(9) Uani 1 1 d . . . C3 C 0.4965(3) 0.7189(3) 0.4956(3) 0.0389(9) Uani 1 1 d . . . C4 C 0.4017(3) 0.7387(3) 0.4314(3) 0.0396(9) Uani 1 1 d . . . C5 C 0.3219(3) 0.6816(3) 0.4510(3) 0.0401(9) Uani 1 1 d . . . C6 C 0.3427(3) 0.6122(3) 0.5357(3) 0.0401(9) Uani 1 1 d . . . C7 C 0.5842(3) 0.7778(3) 0.4823(3) 0.0389(9) Uani 1 1 d . . . C8 C 0.6282(3) 0.8685(4) 0.5432(3) 0.0570(12) Uani 1 1 d . . . H8 H 0.6008 0.8958 0.5900 0.068 Uiso 1 1 calc R . . C9 C 0.7129(3) 0.9192(4) 0.5350(4) 0.0584(12) Uani 1 1 d . . . H9 H 0.7432 0.9791 0.5770 0.070 Uiso 1 1 calc R . . C10 C 0.7515(3) 0.8797(4) 0.4636(3) 0.0490(10) Uani 1 1 d . . . C11 C 0.7083(3) 0.7913(4) 0.4011(3) 0.0542(11) Uani 1 1 d . . . H11 H 0.7351 0.7656 0.3533 0.065 Uiso 1 1 calc R . . C12 C 0.6236(3) 0.7406(4) 0.4103(3) 0.0497(10) Uani 1 1 d . . . H12 H 0.5932 0.6813 0.3678 0.060 Uiso 1 1 calc R . . C13 C 0.2208(3) 0.7041(4) 0.3877(3) 0.0425(9) Uani 1 1 d . . . C14 C 0.1855(3) 0.6621(4) 0.2932(3) 0.0535(11) Uani 1 1 d . . . H14 H 0.2264 0.6192 0.2669 0.064 Uiso 1 1 calc R . . C15 C 0.0905(3) 0.6830(5) 0.2374(4) 0.0645(13) Uani 1 1 d . . . H15 H 0.0678 0.6513 0.1748 0.077 Uiso 1 1 calc R . . C16 C 0.0281(3) 0.7499(4) 0.2722(4) 0.0581(12) Uani 1 1 d . . . C17 C 0.0639(3) 0.7923(5) 0.3649(4) 0.0662(14) Uani 1 1 d . . . H17 H 0.0237 0.8376 0.3903 0.079 Uiso 1 1 calc R . . C18 C 0.1580(3) 0.7698(4) 0.4222(3) 0.0543(11) Uani 1 1 d . . . H18 H 0.1797 0.7996 0.4855 0.065 Uiso 1 1 calc R . . C19 C -0.0748(4) 0.7743(6) 0.2113(4) 0.0894(19) Uani 1 1 d . . . H19A H -0.0893 0.7316 0.1509 0.134 Uiso 1 1 calc R . . H19B H -0.0823 0.8561 0.1973 0.134 Uiso 1 1 calc R . . H19C H -0.1187 0.7510 0.2466 0.134 Uiso 1 1 calc R . . C20 C 0.2608(3) 0.5572(4) 0.5646(3) 0.0428(9) Uani 1 1 d . . . C21 C 0.1950(3) 0.4812(4) 0.5039(3) 0.0527(11) Uani 1 1 d . . . H21 H 0.2013 0.4611 0.4432 0.063 Uiso 1 1 calc R . . C22 C 0.1201(3) 0.4355(4) 0.5337(4) 0.0650(14) Uani 1 1 d . . . H22 H 0.0746 0.3851 0.4935 0.078 Uiso 1 1 calc R . . C23 C 0.1146(4) 0.4665(4) 0.6246(4) 0.0639(13) Uani 1 1 d . . . H23 H 0.0654 0.4368 0.6474 0.077 Uiso 1 1 calc R . . C24 C 0.1821(4) 0.5415(5) 0.6810(4) 0.0654(14) Uani 1 1 d . . . H24 H 0.1767 0.5624 0.7419 0.079 Uiso 1 1 calc R . . O1 O 0.4804(3) 0.4846(3) 0.7900(3) 0.0768(11) Uani 1 1 d . . . H1 H 0.4489 0.5190 0.7400 0.115 Uiso 1 1 d R . . C25 C 0.5630(4) 0.4159(5) 0.8126(4) 0.0690(14) Uani 1 1 d . . . H25A H 0.5995 0.4328 0.7682 0.103 Uiso 1 1 calc R . . H25B H 0.5444 0.3354 0.8069 0.103 Uiso 1 1 calc R . . H25C H 0.6026 0.4318 0.8786 0.103 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 0.0544(4) 0.0891(4) 0.1156(5) -0.0148(3) 0.0504(3) -0.0206(3) N1 0.0333(18) 0.0491(19) 0.0464(19) 0.0042(16) 0.0119(15) -0.0021(15) N2 0.042(2) 0.085(3) 0.063(3) 0.011(2) 0.012(2) 0.004(2) N3 0.0372(19) 0.068(2) 0.053(2) 0.0175(19) 0.0082(16) 0.0003(17) N4 0.048(2) 0.071(3) 0.053(2) -0.0027(19) 0.0191(18) -0.0135(18) C1 0.032(2) 0.062(3) 0.045(2) 0.003(2) 0.0105(19) 0.0023(19) C2 0.032(2) 0.047(2) 0.045(2) 0.0017(19) 0.0106(17) 0.0025(17) C3 0.033(2) 0.043(2) 0.040(2) -0.0002(18) 0.0102(17) 0.0010(17) C4 0.038(2) 0.042(2) 0.039(2) -0.0006(18) 0.0118(17) 0.0002(17) C5 0.032(2) 0.047(2) 0.041(2) -0.0005(19) 0.0107(17) 0.0015(17) C6 0.032(2) 0.043(2) 0.045(2) -0.0034(19) 0.0122(18) -0.0015(17) C7 0.0277(19) 0.047(2) 0.039(2) 0.0008(19) 0.0068(16) -0.0007(17) C8 0.051(3) 0.063(3) 0.067(3) -0.012(2) 0.034(2) -0.010(2) C9 0.046(3) 0.069(3) 0.066(3) -0.025(2) 0.025(2) -0.016(2) C10 0.034(2) 0.056(3) 0.058(3) 0.001(2) 0.015(2) -0.0041(19) C11 0.051(3) 0.062(3) 0.060(3) -0.001(2) 0.033(2) 0.001(2) C12 0.043(2) 0.052(2) 0.059(3) -0.011(2) 0.024(2) -0.007(2) C13 0.032(2) 0.047(2) 0.046(2) 0.0027(19) 0.0093(18) -0.0015(17) C14 0.040(2) 0.066(3) 0.051(3) -0.006(2) 0.007(2) 0.011(2) C15 0.045(3) 0.083(4) 0.056(3) -0.004(3) 0.002(2) 0.003(2) C16 0.035(2) 0.073(3) 0.062(3) 0.013(3) 0.009(2) 0.000(2) C17 0.042(3) 0.087(4) 0.075(3) 0.003(3) 0.025(2) 0.018(2) C18 0.039(2) 0.074(3) 0.048(2) -0.008(2) 0.010(2) 0.006(2) C19 0.041(3) 0.132(6) 0.086(4) 0.027(4) 0.005(3) 0.019(3) C20 0.034(2) 0.050(2) 0.046(2) 0.003(2) 0.0143(18) -0.0020(18) C21 0.047(3) 0.058(3) 0.056(3) -0.008(2) 0.018(2) -0.012(2) C22 0.048(3) 0.063(3) 0.085(4) -0.006(3) 0.020(3) -0.015(2) C23 0.049(3) 0.077(3) 0.073(3) 0.006(3) 0.028(3) -0.016(2) C24 0.058(3) 0.086(4) 0.058(3) -0.001(3) 0.027(2) -0.014(3) O1 0.090(3) 0.087(3) 0.062(2) 0.0117(19) 0.037(2) 0.029(2) C25 0.066(3) 0.075(3) 0.066(3) 0.005(3) 0.020(3) 0.000(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 C10 1.891(4) . ? N1 C6 1.329(5) . ? N1 C2 1.350(5) . ? N2 C1 1.142(5) . ? N3 C4 1.351(5) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? N4 C20 1.344(5) . ? N4 C24 1.345(6) . ? C1 C2 1.450(5) . ? C2 C3 1.372(5) . ? C3 C4 1.411(5) . ? C3 C7 1.494(5) . ? C4 C5 1.422(5) . ? C5 C6 1.405(5) . ? C5 C13 1.484(5) . ? C6 C20 1.502(5) . ? C7 C8 1.382(6) . ? C7 C12 1.387(5) . ? C8 C9 1.387(6) . ? C8 H8 0.9300 . ? C9 C10 1.380(6) . ? C9 H9 0.9300 . ? C10 C11 1.371(6) . ? C11 C12 1.392(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C18 1.378(6) . ? C13 C14 1.379(6) . ? C14 C15 1.377(6) . ? C14 H14 0.9300 . ? C15 C16 1.384(7) . ? C15 H15 0.9300 . ? C16 C17 1.360(7) . ? C16 C19 1.498(7) . ? C17 C18 1.377(6) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.382(6) . ? C21 C22 1.378(6) . ? C21 H21 0.9300 . ? C22 C23 1.375(7) . ? C22 H22 0.9300 . ? C23 C24 1.363(7) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? O1 C25 1.381(6) . ? O1 H1 0.8213 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C2 115.8(3) . . ? C4 N3 H3A 120.0 . . ? C4 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C20 N4 C24 116.7(4) . . ? N2 C1 C2 178.1(5) . . ? N1 C2 C3 126.2(3) . . ? N1 C2 C1 115.8(3) . . ? C3 C2 C1 118.0(4) . . ? C2 C3 C4 117.4(4) . . ? C2 C3 C7 120.6(3) . . ? C4 C3 C7 122.0(3) . . ? N3 C4 C3 120.3(4) . . ? N3 C4 C5 121.3(4) . . ? C3 C4 C5 118.3(3) . . ? C6 C5 C4 117.4(3) . . ? C6 C5 C13 122.5(3) . . ? C4 C5 C13 120.0(3) . . ? N1 C6 C5 124.8(4) . . ? N1 C6 C20 115.3(3) . . ? C5 C6 C20 119.9(3) . . ? C8 C7 C12 119.2(4) . . ? C8 C7 C3 120.3(4) . . ? C12 C7 C3 120.5(4) . . ? C7 C8 C9 120.6(4) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C8 119.1(4) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C11 C10 C9 121.5(4) . . ? C11 C10 Br1 118.9(3) . . ? C9 C10 Br1 119.6(3) . . ? C10 C11 C12 118.9(4) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C7 C12 C11 120.6(4) . . ? C7 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C18 C13 C14 117.2(4) . . ? C18 C13 C5 120.3(4) . . ? C14 C13 C5 122.5(4) . . ? C15 C14 C13 120.7(4) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 121.7(5) . . ? C14 C15 H15 119.1 . . ? C16 C15 H15 119.1 . . ? C17 C16 C15 117.1(4) . . ? C17 C16 C19 120.9(5) . . ? C15 C16 C19 121.9(5) . . ? C16 C17 C18 121.7(4) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? C13 C18 C17 121.5(4) . . ? C13 C18 H18 119.2 . . ? C17 C18 H18 119.2 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N4 C20 C21 122.4(4) . . ? N4 C20 C6 115.2(4) . . ? C21 C20 C6 122.4(4) . . ? C22 C21 C20 119.8(4) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C23 C22 C21 118.0(5) . . ? C23 C22 H22 121.0 . . ? C21 C22 H22 121.0 . . ? C24 C23 C22 119.2(4) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? N4 C24 C23 123.9(5) . . ? N4 C24 H24 118.0 . . ? C23 C24 H24 118.0 . . ? C25 O1 H1 133.3 . . ? O1 C25 H25A 109.5 . . ? O1 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O1 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 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 C6 N1 C2 C3 1.1(6) . . . . ? C6 N1 C2 C1 -177.1(4) . . . . ? N1 C2 C3 C4 -2.5(6) . . . . ? C1 C2 C3 C4 175.7(4) . . . . ? N1 C2 C3 C7 176.3(4) . . . . ? C1 C2 C3 C7 -5.5(6) . . . . ? C2 C3 C4 N3 179.1(4) . . . . ? C7 C3 C4 N3 0.3(6) . . . . ? C2 C3 C4 C5 0.6(6) . . . . ? C7 C3 C4 C5 -178.2(3) . . . . ? N3 C4 C5 C6 -176.2(4) . . . . ? C3 C4 C5 C6 2.3(6) . . . . ? N3 C4 C5 C13 -1.1(6) . . . . ? C3 C4 C5 C13 177.4(4) . . . . ? C2 N1 C6 C5 2.3(6) . . . . ? C2 N1 C6 C20 -177.0(3) . . . . ? C4 C5 C6 N1 -4.0(6) . . . . ? C13 C5 C6 N1 -179.0(4) . . . . ? C4 C5 C6 C20 175.3(4) . . . . ? C13 C5 C6 C20 0.3(6) . . . . ? C2 C3 C7 C8 -73.9(5) . . . . ? C4 C3 C7 C8 104.9(5) . . . . ? C2 C3 C7 C12 104.8(5) . . . . ? C4 C3 C7 C12 -76.5(5) . . . . ? C12 C7 C8 C9 -2.4(7) . . . . ? C3 C7 C8 C9 176.3(4) . . . . ? C7 C8 C9 C10 1.5(7) . . . . ? C8 C9 C10 C11 -0.2(7) . . . . ? C8 C9 C10 Br1 -179.9(4) . . . . ? C9 C10 C11 C12 -0.1(7) . . . . ? Br1 C10 C11 C12 179.5(3) . . . . ? C8 C7 C12 C11 2.0(6) . . . . ? C3 C7 C12 C11 -176.6(4) . . . . ? C10 C11 C12 C7 -0.8(7) . . . . ? C6 C5 C13 C18 67.5(6) . . . . ? C4 C5 C13 C18 -107.3(5) . . . . ? C6 C5 C13 C14 -113.0(5) . . . . ? C4 C5 C13 C14 72.2(5) . . . . ? C18 C13 C14 C15 -1.7(7) . . . . ? C5 C13 C14 C15 178.7(4) . . . . ? C13 C14 C15 C16 2.4(8) . . . . ? C14 C15 C16 C17 -1.4(8) . . . . ? C14 C15 C16 C19 179.1(5) . . . . ? C15 C16 C17 C18 -0.1(8) . . . . ? C19 C16 C17 C18 179.4(5) . . . . ? C14 C13 C18 C17 0.2(7) . . . . ? C5 C13 C18 C17 179.8(4) . . . . ? C16 C17 C18 C13 0.7(8) . . . . ? C24 N4 C20 C21 -1.8(6) . . . . ? C24 N4 C20 C6 178.4(4) . . . . ? N1 C6 C20 N4 58.2(5) . . . . ? C5 C6 C20 N4 -121.1(4) . . . . ? N1 C6 C20 C21 -121.6(4) . . . . ? C5 C6 C20 C21 59.1(6) . . . . ? N4 C20 C21 C22 1.6(7) . . . . ? C6 C20 C21 C22 -178.6(4) . . . . ? C20 C21 C22 C23 -0.9(7) . . . . ? C21 C22 C23 C24 0.6(8) . . . . ? C20 N4 C24 C23 1.5(7) . . . . ? C22 C23 C24 N4 -0.9(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 0.82 2.17 2.923(5) 152 . N3 H3A O1 0.86 2.24 2.972(5) 142 4_575 N3 H3B N4 0.86 2.46 3.144(5) 137 4_575 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.358 _refine_diff_density_min -0.582 _refine_diff_density_rms 0.092