# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email seidel@rutchem.rutgers.edu _publ_contact_author_name 'Daniel Seidel' loop_ _publ_author_name M.Vecchione A.Sun D.Seidel data_aaron001 _database_code_depnum_ccdc_archive 'CCDC 828268' #TrackingRef '- compound 6a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 N2' _chemical_formula_weight 232.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x, y, -z-1/2' '-x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z-1/2' _cell_length_a 54.319(8) _cell_length_b 4.7958(7) _cell_length_c 18.476(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.058(2) _cell_angle_gamma 90.00 _cell_volume 4549.2(11) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5212 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 26.41 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9690 _exptl_absorpt_correction_T_max 0.9976 _exptl_absorpt_process_details 'Bruker SAINT (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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14989 _diffrn_reflns_av_R_equivalents 0.0670 _diffrn_reflns_av_sigmaI/netI 0.0548 _diffrn_reflns_limit_h_min -62 _diffrn_reflns_limit_h_max 62 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 24.71 _reflns_number_total 3886 _reflns_number_gt 2946 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0790P)^2^+7.9000P] 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 3886 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0858 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.1676 _refine_ls_wR_factor_gt 0.1558 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 N1 N 0.09401(4) -0.0801(5) 0.16842(13) 0.0224(6) Uani 1 1 d . . . N2 N 0.09003(4) -0.4331(5) 0.07511(13) 0.0203(5) Uani 1 1 d . . . C1 C 0.07518(5) 0.0795(6) 0.18657(15) 0.0203(6) Uani 1 1 d . . . C2 C 0.07978(6) 0.2836(6) 0.24328(16) 0.0240(7) Uani 1 1 d . . . H2 H 0.0971 0.3305 0.2736 0.029 Uiso 1 1 calc R . . C3 C 0.05870(6) 0.4160(6) 0.25440(16) 0.0263(7) Uani 1 1 d . . . H3 H 0.0616 0.5545 0.2930 0.032 Uiso 1 1 calc R . . C4 C 0.03323(6) 0.3506(6) 0.21014(16) 0.0267(7) Uani 1 1 d . . . H4 H 0.0191 0.4412 0.2198 0.032 Uiso 1 1 calc R . . C5 C 0.02844(6) 0.1547(6) 0.15222(16) 0.0235(6) Uani 1 1 d . . . H5 H 0.0111 0.1133 0.1211 0.028 Uiso 1 1 calc R . . C6 C 0.04949(5) 0.0193(6) 0.14034(15) 0.0200(6) Uani 1 1 d . . . C7 C 0.05210(5) -0.1915(6) 0.08757(15) 0.0212(6) Uani 1 1 d . . . C8 C 0.03618(5) -0.3294(6) 0.02746(16) 0.0222(6) Uani 1 1 d . . . H8 H 0.0180 -0.2943 0.0109 0.027 Uiso 1 1 calc R . . C9 C 0.04675(6) -0.5305(6) -0.01176(16) 0.0224(6) Uani 1 1 d . . . C10 C 0.03085(6) -0.6800(6) -0.07570(16) 0.0255(7) Uani 1 1 d . . . H10 H 0.0127 -0.6437 -0.0942 0.031 Uiso 1 1 calc R . . C11 C 0.04103(6) -0.8763(6) -0.11177(17) 0.0259(7) Uani 1 1 d . . . H11 H 0.0301 -0.9743 -0.1549 0.031 Uiso 1 1 calc R . . C12 C 0.06773(6) -0.9304(6) -0.08433(16) 0.0263(7) Uani 1 1 d . . . H12 H 0.0748 -1.0684 -0.1087 0.032 Uiso 1 1 calc R . . C13 C 0.08387(6) -0.7884(6) -0.02292(16) 0.0239(7) Uani 1 1 d . . . H13 H 0.1020 -0.8288 -0.0051 0.029 Uiso 1 1 calc R . . C14 C 0.07377(5) -0.5826(6) 0.01399(15) 0.0208(6) Uani 1 1 d . . . C15 C 0.08018(5) -0.2381(6) 0.11130(15) 0.0198(6) Uani 1 1 d . . . C16 C 0.11812(5) -0.4861(6) 0.10291(18) 0.0285(7) Uani 1 1 d . . . H16A H 0.1267 -0.3514 0.1432 0.043 Uiso 1 1 calc R . . H16B H 0.1251 -0.4668 0.0605 0.043 Uiso 1 1 calc R . . H16C H 0.1214 -0.6756 0.1237 0.043 Uiso 1 1 calc R . . N3 N 0.16008(5) 0.5145(5) -0.00485(14) 0.0243(6) Uani 1 1 d . . . N4 N 0.15885(4) 0.1732(5) -0.09965(13) 0.0223(5) Uani 1 1 d . . . C17 C 0.18072(6) 0.6114(6) 0.05831(16) 0.0245(7) Uani 1 1 d . . . C18 C 0.17975(6) 0.8222(6) 0.10917(17) 0.0287(7) Uani 1 1 d . . . H18 H 0.1638 0.9150 0.1044 0.034 Uiso 1 1 calc R . . C19 C 0.20238(6) 0.8932(6) 0.16663(17) 0.0315(8) Uani 1 1 d . . . H19 H 0.2019 1.0373 0.2014 0.038 Uiso 1 1 calc R . . C20 C 0.22609(6) 0.7584(6) 0.17516(17) 0.0311(7) Uani 1 1 d . . . H20 H 0.2414 0.8115 0.2153 0.037 Uiso 1 1 calc R . . C21 C 0.22716(6) 0.5482(6) 0.12503(16) 0.0261(7) Uani 1 1 d . . . H21 H 0.2431 0.4539 0.1306 0.031 Uiso 1 1 calc R . . C22 C 0.20457(6) 0.4775(6) 0.06637(16) 0.0231(7) Uani 1 1 d . . . C23 C 0.19867(5) 0.2803(6) 0.00385(15) 0.0219(6) Uani 1 1 d . . . C24 C 0.21207(5) 0.0876(6) -0.02105(16) 0.0220(6) Uani 1 1 d . . . H24 H 0.2300 0.0562 0.0060 0.026 Uiso 1 1 calc R . . C25 C 0.19917(5) -0.0685(6) -0.08821(16) 0.0212(6) Uani 1 1 d . . . C26 C 0.21221(6) -0.2725(6) -0.11651(16) 0.0240(7) Uani 1 1 d . . . H26 H 0.2301 -0.3084 -0.0897 0.029 Uiso 1 1 calc R . . C27 C 0.19990(6) -0.4209(6) -0.18163(17) 0.0269(7) Uani 1 1 d . . . H27 H 0.2091 -0.5583 -0.1997 0.032 Uiso 1 1 calc R . . C28 C 0.17370(6) -0.3670(6) -0.22091(17) 0.0273(7) Uani 1 1 d . . . H28 H 0.1651 -0.4675 -0.2665 0.033 Uiso 1 1 calc R . . C29 C 0.16004(6) -0.1711(6) -0.19498(16) 0.0254(7) Uani 1 1 d . . . H29 H 0.1422 -0.1377 -0.2226 0.031 Uiso 1 1 calc R . . C30 C 0.17246(5) -0.0209(6) -0.12783(15) 0.0210(6) Uani 1 1 d . . . C31 C 0.17123(5) 0.3236(6) -0.03555(16) 0.0215(6) Uani 1 1 d . . . C32 C 0.13092(5) 0.2111(7) -0.13646(17) 0.0300(7) Uani 1 1 d . . . H32A H 0.1272 0.2439 -0.1913 0.045 Uiso 1 1 calc R . . H32B H 0.1250 0.3716 -0.1137 0.045 Uiso 1 1 calc R . . H32C H 0.1217 0.0432 -0.1291 0.045 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 N1 0.0262(13) 0.0145(12) 0.0267(13) 0.0004(10) 0.0087(11) -0.0018(10) N2 0.0227(13) 0.0132(12) 0.0262(12) 0.0010(10) 0.0096(10) -0.0002(10) C1 0.0274(15) 0.0123(14) 0.0219(14) 0.0030(12) 0.0091(12) -0.0027(12) C2 0.0305(16) 0.0157(15) 0.0259(15) 0.0017(12) 0.0092(13) -0.0034(13) C3 0.0412(18) 0.0121(15) 0.0269(15) -0.0001(12) 0.0130(14) -0.0017(13) C4 0.0364(17) 0.0148(15) 0.0331(17) 0.0031(13) 0.0172(14) 0.0048(13) C5 0.0278(16) 0.0142(14) 0.0297(15) 0.0021(12) 0.0109(12) -0.0008(12) C6 0.0283(15) 0.0096(13) 0.0246(14) 0.0031(12) 0.0120(12) 0.0001(12) C7 0.0260(15) 0.0148(15) 0.0237(15) 0.0036(12) 0.0091(12) -0.0013(12) C8 0.0233(15) 0.0151(15) 0.0286(15) 0.0031(12) 0.0090(12) 0.0001(12) C9 0.0316(16) 0.0129(14) 0.0247(15) 0.0039(12) 0.0121(13) -0.0003(12) C10 0.0322(17) 0.0163(15) 0.0297(16) 0.0024(13) 0.0126(13) -0.0040(13) C11 0.0374(18) 0.0155(15) 0.0264(15) -0.0004(13) 0.0126(13) -0.0063(13) C12 0.0396(18) 0.0142(15) 0.0304(16) -0.0005(13) 0.0188(14) -0.0029(13) C13 0.0292(16) 0.0160(15) 0.0301(15) 0.0026(13) 0.0146(13) -0.0003(13) C14 0.0282(15) 0.0112(14) 0.0250(15) 0.0039(12) 0.0115(12) -0.0017(12) C15 0.0244(15) 0.0127(14) 0.0238(14) 0.0030(12) 0.0098(12) -0.0016(12) C16 0.0251(16) 0.0217(16) 0.0399(18) -0.0017(14) 0.0123(14) 0.0016(13) N3 0.0276(13) 0.0160(13) 0.0319(13) -0.0001(11) 0.0135(11) -0.0024(10) N4 0.0213(12) 0.0179(13) 0.0282(13) 0.0006(11) 0.0087(10) 0.0004(10) C17 0.0359(17) 0.0158(15) 0.0267(15) 0.0029(12) 0.0169(13) -0.0054(13) C18 0.0421(18) 0.0144(15) 0.0360(17) -0.0012(14) 0.0214(15) -0.0042(14) C19 0.053(2) 0.0155(16) 0.0328(17) -0.0003(13) 0.0236(16) -0.0075(15) C20 0.0425(19) 0.0248(17) 0.0260(16) 0.0005(14) 0.0110(14) -0.0124(15) C21 0.0327(17) 0.0167(15) 0.0286(16) 0.0042(13) 0.0095(13) -0.0048(13) C22 0.0325(16) 0.0125(14) 0.0275(15) 0.0055(12) 0.0141(13) -0.0035(12) C23 0.0274(16) 0.0141(14) 0.0258(15) 0.0035(12) 0.0106(12) -0.0043(12) C24 0.0224(15) 0.0156(15) 0.0276(15) 0.0078(12) 0.0077(12) -0.0009(12) C25 0.0265(16) 0.0125(14) 0.0266(15) 0.0039(12) 0.0114(12) -0.0019(12) C26 0.0250(15) 0.0178(15) 0.0309(16) 0.0072(13) 0.0114(13) 0.0021(12) C27 0.0375(18) 0.0147(15) 0.0343(17) 0.0022(13) 0.0199(14) 0.0014(13) C28 0.0317(17) 0.0213(16) 0.0312(16) -0.0029(13) 0.0132(14) -0.0053(13) C29 0.0225(15) 0.0222(16) 0.0323(16) 0.0006(13) 0.0098(13) -0.0016(13) C30 0.0253(15) 0.0129(14) 0.0266(15) 0.0032(12) 0.0110(12) -0.0009(12) C31 0.0282(15) 0.0123(14) 0.0264(15) 0.0008(12) 0.0121(12) -0.0023(12) C32 0.0234(16) 0.0315(18) 0.0338(17) -0.0055(15) 0.0079(13) 0.0031(14) _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 N1 C15 1.317(3) . ? N1 C1 1.403(4) . ? N2 C15 1.357(3) . ? N2 C14 1.385(4) . ? N2 C16 1.465(3) . ? C1 C2 1.395(4) . ? C1 C6 1.408(4) . ? C2 C3 1.382(4) . ? C2 H2 0.9500 . ? C3 C4 1.394(4) . ? C3 H3 0.9500 . ? C4 C5 1.383(4) . ? C4 H4 0.9500 . ? C5 C6 1.394(4) . ? C5 H5 0.9500 . ? C6 C7 1.443(4) . ? C7 C8 1.339(4) . ? C7 C15 1.460(4) . ? C8 C9 1.434(4) . ? C8 H8 0.9500 . ? C9 C14 1.410(4) . ? C9 C10 1.410(4) . ? C10 C11 1.370(4) . ? C10 H10 0.9500 . ? C11 C12 1.395(4) . ? C11 H11 0.9500 . ? C12 C13 1.368(4) . ? C12 H12 0.9500 . ? C13 C14 1.409(4) . ? C13 H13 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N3 C31 1.323(4) . ? N3 C17 1.407(4) . ? N4 C31 1.362(4) . ? N4 C30 1.391(4) . ? N4 C32 1.457(4) . ? C17 C18 1.393(4) . ? C17 C22 1.410(4) . ? C18 C19 1.379(4) . ? C18 H18 0.9500 . ? C19 C20 1.403(5) . ? C19 H19 0.9500 . ? C20 C21 1.383(4) . ? C20 H20 0.9500 . ? C21 C22 1.388(4) . ? C21 H21 0.9500 . ? C22 C23 1.445(4) . ? C23 C24 1.347(4) . ? C23 C31 1.445(4) . ? C24 C25 1.422(4) . ? C24 H24 0.9500 . ? C25 C26 1.405(4) . ? C25 C30 1.414(4) . ? C26 C27 1.370(4) . ? C26 H26 0.9500 . ? C27 C28 1.394(4) . ? C27 H27 0.9500 . ? C28 C29 1.376(4) . ? C28 H28 0.9500 . ? C29 C30 1.403(4) . ? C29 H29 0.9500 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? 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 C15 N1 C1 103.6(2) . . ? C15 N2 C14 120.6(2) . . ? C15 N2 C16 118.7(2) . . ? C14 N2 C16 120.7(2) . . ? C2 C1 N1 126.6(3) . . ? C2 C1 C6 119.9(3) . . ? N1 C1 C6 113.5(2) . . ? C3 C2 C1 118.7(3) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 121.4(3) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 120.4(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 118.8(3) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C5 C6 C1 120.7(3) . . ? C5 C6 C7 134.4(3) . . ? C1 C6 C7 104.9(2) . . ? C8 C7 C6 136.6(3) . . ? C8 C7 C15 120.1(3) . . ? C6 C7 C15 103.2(2) . . ? C7 C8 C9 119.7(3) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C14 C9 C10 118.6(3) . . ? C14 C9 C8 119.5(3) . . ? C10 C9 C8 121.9(3) . . ? C11 C10 C9 121.5(3) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C10 C11 C12 119.2(3) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C13 C12 C11 121.2(3) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 120.3(3) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? N2 C14 C13 120.8(3) . . ? N2 C14 C9 120.0(2) . . ? C13 C14 C9 119.2(3) . . ? N1 C15 N2 125.3(2) . . ? N1 C15 C7 114.8(2) . . ? N2 C15 C7 119.9(2) . . ? N2 C16 H16A 109.5 . . ? N2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C31 N3 C17 103.4(2) . . ? C31 N4 C30 120.5(2) . . ? C31 N4 C32 118.9(2) . . ? C30 N4 C32 120.6(2) . . ? C18 C17 N3 127.1(3) . . ? C18 C17 C22 119.7(3) . . ? N3 C17 C22 113.1(3) . . ? C19 C18 C17 118.5(3) . . ? C19 C18 H18 120.7 . . ? C17 C18 H18 120.7 . . ? C18 C19 C20 121.8(3) . . ? C18 C19 H19 119.1 . . ? C20 C19 H19 119.1 . . ? C21 C20 C19 119.9(3) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C22 118.7(3) . . ? C20 C21 H21 120.6 . . ? C22 C21 H21 120.6 . . ? C21 C22 C17 121.3(3) . . ? C21 C22 C23 133.8(3) . . ? C17 C22 C23 104.9(2) . . ? C24 C23 C31 120.7(3) . . ? C24 C23 C22 135.9(3) . . ? C31 C23 C22 103.4(2) . . ? C23 C24 C25 119.5(3) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? C26 C25 C30 118.5(3) . . ? C26 C25 C24 121.8(3) . . ? C30 C25 C24 119.8(3) . . ? C27 C26 C25 121.8(3) . . ? C27 C26 H26 119.1 . . ? C25 C26 H26 119.1 . . ? C26 C27 C28 118.9(3) . . ? C26 C27 H27 120.5 . . ? C28 C27 H27 120.5 . . ? C29 C28 C27 121.3(3) . . ? C29 C28 H28 119.3 . . ? C27 C28 H28 119.3 . . ? C28 C29 C30 120.0(3) . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? N4 C30 C29 120.9(2) . . ? N4 C30 C25 119.7(2) . . ? C29 C30 C25 119.4(3) . . ? N3 C31 N4 125.1(3) . . ? N3 C31 C23 115.1(2) . . ? N4 C31 C23 119.8(2) . . ? N4 C32 H32A 109.5 . . ? N4 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N4 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 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 C15 N1 C1 C2 -179.3(3) . . . . ? C15 N1 C1 C6 0.1(3) . . . . ? N1 C1 C2 C3 -178.5(3) . . . . ? C6 C1 C2 C3 2.2(4) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? C2 C3 C4 C5 -1.6(4) . . . . ? C3 C4 C5 C6 1.6(4) . . . . ? C4 C5 C6 C1 0.3(4) . . . . ? C4 C5 C6 C7 179.6(3) . . . . ? C2 C1 C6 C5 -2.2(4) . . . . ? N1 C1 C6 C5 178.4(2) . . . . ? C2 C1 C6 C7 178.3(2) . . . . ? N1 C1 C6 C7 -1.1(3) . . . . ? C5 C6 C7 C8 4.5(6) . . . . ? C1 C6 C7 C8 -176.1(3) . . . . ? C5 C6 C7 C15 -177.9(3) . . . . ? C1 C6 C7 C15 1.5(3) . . . . ? C6 C7 C8 C9 179.7(3) . . . . ? C15 C7 C8 C9 2.3(4) . . . . ? C7 C8 C9 C14 0.7(4) . . . . ? C7 C8 C9 C10 -179.5(3) . . . . ? C14 C9 C10 C11 1.3(4) . . . . ? C8 C9 C10 C11 -178.5(3) . . . . ? C9 C10 C11 C12 0.3(4) . . . . ? C10 C11 C12 C13 -0.9(4) . . . . ? C11 C12 C13 C14 -0.1(4) . . . . ? C15 N2 C14 C13 -179.0(2) . . . . ? C16 N2 C14 C13 -0.1(4) . . . . ? C15 N2 C14 C9 0.7(4) . . . . ? C16 N2 C14 C9 179.6(2) . . . . ? C12 C13 C14 N2 -178.5(2) . . . . ? C12 C13 C14 C9 1.8(4) . . . . ? C10 C9 C14 N2 178.0(2) . . . . ? C8 C9 C14 N2 -2.2(4) . . . . ? C10 C9 C14 C13 -2.3(4) . . . . ? C8 C9 C14 C13 177.5(2) . . . . ? C1 N1 C15 N2 -178.7(2) . . . . ? C1 N1 C15 C7 1.0(3) . . . . ? C14 N2 C15 N1 -178.1(2) . . . . ? C16 N2 C15 N1 3.1(4) . . . . ? C14 N2 C15 C7 2.2(4) . . . . ? C16 N2 C15 C7 -176.6(2) . . . . ? C8 C7 C15 N1 176.5(2) . . . . ? C6 C7 C15 N1 -1.7(3) . . . . ? C8 C7 C15 N2 -3.8(4) . . . . ? C6 C7 C15 N2 178.1(2) . . . . ? C31 N3 C17 C18 177.7(3) . . . . ? C31 N3 C17 C22 -0.3(3) . . . . ? N3 C17 C18 C19 -178.2(3) . . . . ? C22 C17 C18 C19 -0.3(4) . . . . ? C17 C18 C19 C20 -0.3(4) . . . . ? C18 C19 C20 C21 0.0(4) . . . . ? C19 C20 C21 C22 0.8(4) . . . . ? C20 C21 C22 C17 -1.4(4) . . . . ? C20 C21 C22 C23 177.9(3) . . . . ? C18 C17 C22 C21 1.1(4) . . . . ? N3 C17 C22 C21 179.3(2) . . . . ? C18 C17 C22 C23 -178.3(2) . . . . ? N3 C17 C22 C23 -0.1(3) . . . . ? C21 C22 C23 C24 1.8(6) . . . . ? C17 C22 C23 C24 -178.9(3) . . . . ? C21 C22 C23 C31 -178.8(3) . . . . ? C17 C22 C23 C31 0.5(3) . . . . ? C31 C23 C24 C25 1.9(4) . . . . ? C22 C23 C24 C25 -178.8(3) . . . . ? C23 C24 C25 C26 -179.8(3) . . . . ? C23 C24 C25 C30 -0.3(4) . . . . ? C30 C25 C26 C27 1.2(4) . . . . ? C24 C25 C26 C27 -179.3(3) . . . . ? C25 C26 C27 C28 0.2(4) . . . . ? C26 C27 C28 C29 -0.8(4) . . . . ? C27 C28 C29 C30 0.1(4) . . . . ? C31 N4 C30 C29 -178.2(2) . . . . ? C32 N4 C30 C29 4.2(4) . . . . ? C31 N4 C30 C25 2.0(4) . . . . ? C32 N4 C30 C25 -175.6(3) . . . . ? C28 C29 C30 N4 -178.4(3) . . . . ? C28 C29 C30 C25 1.3(4) . . . . ? C26 C25 C30 N4 177.9(2) . . . . ? C24 C25 C30 N4 -1.7(4) . . . . ? C26 C25 C30 C29 -1.9(4) . . . . ? C24 C25 C30 C29 178.5(2) . . . . ? C17 N3 C31 N4 -178.9(3) . . . . ? C17 N3 C31 C23 0.7(3) . . . . ? C30 N4 C31 N3 179.2(3) . . . . ? C32 N4 C31 N3 -3.1(4) . . . . ? C30 N4 C31 C23 -0.4(4) . . . . ? C32 N4 C31 C23 177.2(2) . . . . ? C24 C23 C31 N3 178.7(2) . . . . ? C22 C23 C31 N3 -0.8(3) . . . . ? C24 C23 C31 N4 -1.6(4) . . . . ? C22 C23 C31 N4 178.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.244 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.058 # Attachment '- compound 17.cif' data_aaron002 _database_code_depnum_ccdc_archive 'CCDC 828269' #TrackingRef '- compound 17.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 N2' _chemical_formula_weight 308.37 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' _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 14.9876(13) _cell_length_b 5.6399(5) _cell_length_c 18.1283(16) _cell_angle_alpha 90.00 _cell_angle_beta 94.317(2) _cell_angle_gamma 90.00 _cell_volume 1528.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6015 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 31.92 _exptl_crystal_description needles _exptl_crystal_colour orange _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9774 _exptl_absorpt_correction_T_max 0.9984 _exptl_absorpt_process_details 'Bruker SAINT (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 'Bruker APEX SMART CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16429 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 30.51 _reflns_number_total 4628 _reflns_number_gt 3687 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0630P)^2^+0.6300P] 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 4628 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1292 _refine_ls_wR_factor_gt 0.1199 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 N1 N 0.23565(6) -0.13030(19) 0.38146(5) 0.0163(2) Uani 1 1 d . . . N2 N 0.27165(7) 0.17632(19) 0.29892(6) 0.0179(2) Uani 1 1 d . . . C1 C 0.33704(8) 0.3557(2) 0.30452(6) 0.0170(2) Uani 1 1 d . . . C2 C 0.35084(8) 0.5298(2) 0.25231(7) 0.0201(2) Uani 1 1 d . . . H2 H 0.3150 0.5354 0.2068 0.024 Uiso 1 1 calc R . . C3 C 0.41820(8) 0.6954(2) 0.26805(7) 0.0215(3) Uani 1 1 d . . . H3 H 0.4286 0.8143 0.2326 0.026 Uiso 1 1 calc R . . C4 C 0.47100(8) 0.6906(2) 0.33508(7) 0.0215(3) Uani 1 1 d . . . H4 H 0.5167 0.8058 0.3445 0.026 Uiso 1 1 calc R . . C5 C 0.45717(8) 0.5191(2) 0.38792(7) 0.0188(2) Uani 1 1 d . . . H5 H 0.4925 0.5167 0.4337 0.023 Uiso 1 1 calc R . . C6 C 0.39049(7) 0.3506(2) 0.37260(6) 0.0162(2) Uani 1 1 d . . . C7 C 0.35639(7) 0.1528(2) 0.41271(6) 0.0156(2) Uani 1 1 d . . . C8 C 0.37485(8) 0.0499(2) 0.47974(6) 0.0169(2) Uani 1 1 d . . . H8 H 0.4219 0.1087 0.5127 0.020 Uiso 1 1 calc R . . C9 C 0.32257(8) -0.1481(2) 0.50010(6) 0.0168(2) Uani 1 1 d . . . C10 C 0.33930(8) -0.2625(2) 0.56897(7) 0.0205(3) Uani 1 1 d . . . H10 H 0.3871 -0.2083 0.6021 0.025 Uiso 1 1 calc R . . C11 C 0.28818(9) -0.4505(2) 0.58929(7) 0.0239(3) Uani 1 1 d . . . H11 H 0.3009 -0.5264 0.6357 0.029 Uiso 1 1 calc R . . C12 C 0.21726(9) -0.5288(2) 0.54079(7) 0.0232(3) Uani 1 1 d . . . H12 H 0.1812 -0.6571 0.5549 0.028 Uiso 1 1 calc R . . C13 C 0.19894(8) -0.4226(2) 0.47285(7) 0.0201(2) Uani 1 1 d . . . H13 H 0.1502 -0.4775 0.4408 0.024 Uiso 1 1 calc R . . C14 C 0.25182(8) -0.2341(2) 0.45079(6) 0.0164(2) Uani 1 1 d . . . C15 C 0.28433(7) 0.0608(2) 0.36198(6) 0.0156(2) Uani 1 1 d . . . C16 C 0.16361(8) -0.2162(2) 0.32900(6) 0.0177(2) Uani 1 1 d . . . H16A H 0.1642 -0.3917 0.3289 0.021 Uiso 1 1 calc R . . H16B H 0.1752 -0.1620 0.2787 0.021 Uiso 1 1 calc R . . C17 C 0.07163(8) -0.1312(2) 0.34694(6) 0.0168(2) Uani 1 1 d . . . C18 C 0.06047(9) 0.0614(2) 0.39265(8) 0.0261(3) Uani 1 1 d . . . H18 H 0.1114 0.1374 0.4164 0.031 Uiso 1 1 calc R . . C19 C -0.02483(9) 0.1447(3) 0.40419(9) 0.0307(3) Uani 1 1 d . . . H19 H -0.0318 0.2771 0.4356 0.037 Uiso 1 1 calc R . . C20 C -0.09940(9) 0.0352(3) 0.36997(8) 0.0258(3) Uani 1 1 d . . . H20 H -0.1575 0.0933 0.3774 0.031 Uiso 1 1 calc R . . C21 C -0.08914(8) -0.1591(3) 0.32499(7) 0.0233(3) Uani 1 1 d . . . H21 H -0.1403 -0.2351 0.3016 0.028 Uiso 1 1 calc R . . C22 C -0.00392(8) -0.2436(2) 0.31393(7) 0.0205(2) Uani 1 1 d . . . H22 H 0.0028 -0.3790 0.2837 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 N1 0.0146(4) 0.0189(5) 0.0151(4) -0.0009(4) -0.0005(3) -0.0003(4) N2 0.0162(4) 0.0204(5) 0.0169(5) 0.0007(4) -0.0005(3) 0.0002(4) C1 0.0142(5) 0.0199(6) 0.0171(5) -0.0014(4) 0.0021(4) 0.0022(4) C2 0.0195(5) 0.0235(6) 0.0176(5) 0.0010(5) 0.0024(4) 0.0017(5) C3 0.0238(6) 0.0212(6) 0.0203(6) 0.0014(5) 0.0075(5) 0.0000(5) C4 0.0210(6) 0.0218(6) 0.0226(6) -0.0041(5) 0.0067(5) -0.0036(5) C5 0.0169(5) 0.0218(6) 0.0179(5) -0.0050(5) 0.0027(4) -0.0002(4) C6 0.0148(5) 0.0189(6) 0.0152(5) -0.0019(4) 0.0028(4) 0.0018(4) C7 0.0128(5) 0.0182(6) 0.0159(5) -0.0033(4) 0.0013(4) 0.0013(4) C8 0.0144(5) 0.0206(6) 0.0157(5) -0.0031(4) 0.0004(4) 0.0021(4) C9 0.0164(5) 0.0182(6) 0.0157(5) -0.0017(4) 0.0017(4) 0.0034(4) C10 0.0222(6) 0.0230(6) 0.0161(5) -0.0003(5) 0.0010(4) 0.0045(5) C11 0.0294(7) 0.0229(7) 0.0196(6) 0.0037(5) 0.0038(5) 0.0058(5) C12 0.0279(6) 0.0172(6) 0.0251(6) 0.0024(5) 0.0065(5) 0.0014(5) C13 0.0201(5) 0.0178(6) 0.0225(6) -0.0007(5) 0.0028(4) 0.0009(4) C14 0.0167(5) 0.0168(6) 0.0159(5) -0.0006(4) 0.0021(4) 0.0032(4) C15 0.0132(5) 0.0172(5) 0.0163(5) -0.0019(4) 0.0012(4) 0.0008(4) C16 0.0164(5) 0.0188(6) 0.0175(5) -0.0034(4) -0.0012(4) -0.0007(4) C17 0.0156(5) 0.0170(6) 0.0177(5) 0.0009(4) -0.0004(4) -0.0005(4) C18 0.0181(6) 0.0230(7) 0.0366(7) -0.0098(6) -0.0006(5) -0.0009(5) C19 0.0229(6) 0.0254(7) 0.0439(8) -0.0112(6) 0.0039(6) 0.0034(5) C20 0.0174(6) 0.0272(7) 0.0331(7) 0.0032(6) 0.0036(5) 0.0023(5) C21 0.0163(5) 0.0291(7) 0.0240(6) 0.0027(5) -0.0014(4) -0.0049(5) C22 0.0203(6) 0.0222(6) 0.0188(5) -0.0017(5) 0.0002(4) -0.0038(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 N1 C15 1.3628(15) . ? N1 C14 1.3911(15) . ? N1 C16 1.4663(15) . ? N2 C15 1.3172(15) . ? N2 C1 1.4069(16) . ? C1 C2 1.3901(17) . ? C1 C6 1.4201(16) . ? C2 C3 1.3890(18) . ? C2 H2 0.9500 . ? C3 C4 1.3995(18) . ? C3 H3 0.9500 . ? C4 C5 1.3881(18) . ? C4 H4 0.9500 . ? C5 C6 1.3918(17) . ? C5 H5 0.9500 . ? C6 C7 1.4457(17) . ? C7 C8 1.3562(16) . ? C7 C15 1.4602(16) . ? C8 C9 1.4286(17) . ? C8 H8 0.9500 . ? C9 C10 1.4110(17) . ? C9 C14 1.4198(16) . ? C10 C11 1.3747(19) . ? C10 H10 0.9500 . ? C11 C12 1.3989(19) . ? C11 H11 0.9500 . ? C12 C13 1.3782(18) . ? C12 H12 0.9500 . ? C13 C14 1.4024(18) . ? C13 H13 0.9500 . ? C16 C17 1.5177(16) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.3840(18) . ? C17 C22 1.3930(16) . ? C18 C19 1.3926(18) . ? C18 H18 0.9500 . ? C19 C20 1.3825(19) . ? C19 H19 0.9500 . ? C20 C21 1.381(2) . ? C20 H20 0.9500 . ? C21 C22 1.3919(18) . ? C21 H21 0.9500 . ? 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 C15 N1 C14 120.44(10) . . ? C15 N1 C16 118.39(10) . . ? C14 N1 C16 121.11(10) . . ? C15 N2 C1 103.82(9) . . ? C2 C1 N2 126.68(11) . . ? C2 C1 C6 120.20(11) . . ? N2 C1 C6 113.11(10) . . ? C3 C2 C1 118.56(11) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 121.34(12) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 120.58(12) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 118.71(11) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C5 C6 C1 120.61(11) . . ? C5 C6 C7 134.59(11) . . ? C1 C6 C7 104.78(10) . . ? C8 C7 C6 136.46(11) . . ? C8 C7 C15 120.24(11) . . ? C6 C7 C15 103.30(10) . . ? C7 C8 C9 119.16(11) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C14 118.40(11) . . ? C10 C9 C8 121.45(11) . . ? C14 C9 C8 120.16(11) . . ? C11 C10 C9 121.62(12) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C10 C11 C12 119.17(12) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C13 C12 C11 121.03(12) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 120.36(12) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? N1 C14 C13 120.86(11) . . ? N1 C14 C9 119.75(11) . . ? C13 C14 C9 119.38(11) . . ? N2 C15 N1 124.83(10) . . ? N2 C15 C7 114.98(11) . . ? N1 C15 C7 120.19(10) . . ? N1 C16 C17 113.15(10) . . ? N1 C16 H16A 108.9 . . ? C17 C16 H16A 108.9 . . ? N1 C16 H16B 108.9 . . ? C17 C16 H16B 108.9 . . ? H16A C16 H16B 107.8 . . ? C18 C17 C22 118.92(11) . . ? C18 C17 C16 121.93(11) . . ? C22 C17 C16 119.09(11) . . ? C17 C18 C19 120.56(12) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C20 C19 C18 120.14(13) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C21 C20 C19 119.81(12) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C22 120.06(12) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C21 C22 C17 120.48(12) . . ? C21 C22 H22 119.8 . . ? C17 C22 H22 119.8 . . ? 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 C15 N2 C1 C2 -178.81(12) . . . . ? C15 N2 C1 C6 -0.35(13) . . . . ? N2 C1 C2 C3 179.00(11) . . . . ? C6 C1 C2 C3 0.65(17) . . . . ? C1 C2 C3 C4 -0.61(18) . . . . ? C2 C3 C4 C5 -0.07(19) . . . . ? C3 C4 C5 C6 0.69(18) . . . . ? C4 C5 C6 C1 -0.65(17) . . . . ? C4 C5 C6 C7 -179.02(12) . . . . ? C2 C1 C6 C5 -0.03(17) . . . . ? N2 C1 C6 C5 -178.59(10) . . . . ? C2 C1 C6 C7 178.77(11) . . . . ? N2 C1 C6 C7 0.21(13) . . . . ? C5 C6 C7 C8 -0.7(2) . . . . ? C1 C6 C7 C8 -179.24(13) . . . . ? C5 C6 C7 C15 178.56(13) . . . . ? C1 C6 C7 C15 0.01(12) . . . . ? C6 C7 C8 C9 178.75(12) . . . . ? C15 C7 C8 C9 -0.41(17) . . . . ? C7 C8 C9 C10 179.64(11) . . . . ? C7 C8 C9 C14 -0.50(17) . . . . ? C14 C9 C10 C11 -0.99(18) . . . . ? C8 C9 C10 C11 178.88(12) . . . . ? C9 C10 C11 C12 -0.67(19) . . . . ? C10 C11 C12 C13 1.0(2) . . . . ? C11 C12 C13 C14 0.44(19) . . . . ? C15 N1 C14 C13 176.55(11) . . . . ? C16 N1 C14 C13 -0.69(17) . . . . ? C15 N1 C14 C9 -3.28(16) . . . . ? C16 N1 C14 C9 179.47(10) . . . . ? C12 C13 C14 N1 178.04(11) . . . . ? C12 C13 C14 C9 -2.12(18) . . . . ? C10 C9 C14 N1 -177.79(10) . . . . ? C8 C9 C14 N1 2.34(17) . . . . ? C10 C9 C14 C13 2.37(17) . . . . ? C8 C9 C14 C13 -177.50(11) . . . . ? C1 N2 C15 N1 -179.98(11) . . . . ? C1 N2 C15 C7 0.36(13) . . . . ? C14 N1 C15 N2 -177.26(11) . . . . ? C16 N1 C15 N2 0.06(17) . . . . ? C14 N1 C15 C7 2.39(16) . . . . ? C16 N1 C15 C7 179.70(10) . . . . ? C8 C7 C15 N2 179.16(11) . . . . ? C6 C7 C15 N2 -0.25(13) . . . . ? C8 C7 C15 N1 -0.52(17) . . . . ? C6 C7 C15 N1 -179.93(10) . . . . ? C15 N1 C16 C17 -99.36(12) . . . . ? C14 N1 C16 C17 77.93(14) . . . . ? N1 C16 C17 C18 18.72(17) . . . . ? N1 C16 C17 C22 -164.13(11) . . . . ? C22 C17 C18 C19 -1.4(2) . . . . ? C16 C17 C18 C19 175.76(13) . . . . ? C17 C18 C19 C20 0.0(2) . . . . ? C18 C19 C20 C21 0.8(2) . . . . ? C19 C20 C21 C22 -0.3(2) . . . . ? C20 C21 C22 C17 -1.1(2) . . . . ? C18 C17 C22 C21 1.93(19) . . . . ? C16 C17 C22 C21 -175.30(11) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.468 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.055 # Attachment '- compound 11i.cif' data_mv498 _database_code_depnum_ccdc_archive 'CCDC 828270' #TrackingRef '- compound 11i.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H10 Br2 N2' _chemical_formula_sum 'C15 H10 Br2 N2' _chemical_formula_weight 378.07 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' 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 18.7505(12) _cell_length_b 7.0987(4) _cell_length_c 20.0419(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2667.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9424 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 31.67 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.883 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 6.063 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.376 _exptl_absorpt_correction_T_max 0.839 _exptl_absorpt_process_details 'Bruker SAINT (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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 27715 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 31.84 _reflns_number_total 4549 _reflns_number_gt 3440 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The SHELXL restraints used were dfix 0.88 .02 n2 h101 n2 h102 ; _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^)+(0.0380P)^2^+3.0000P] 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 4549 _refine_ls_number_parameters 178 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0854 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 0.084745(14) -0.01457(4) 0.112564(14) 0.02421(8) Uani 1 1 d . . . Br2 Br 0.306464(16) 0.18764(4) 0.290823(11) 0.02310(7) Uani 1 1 d . . . N1 N 0.21031(11) -0.0769(3) 0.01705(10) 0.0164(4) Uani 1 1 d . . . N2 N 0.42261(17) 0.2401(4) -0.06557(15) 0.0403(7) Uani 1 1 d D . . H101 H 0.4473(19) 0.334(4) -0.0793(19) 0.048 Uiso 1 1 d D . . H102 H 0.3900(17) 0.266(5) -0.0370(16) 0.048 Uiso 1 1 d D . . C1 C 0.23320(13) -0.0186(3) 0.07851(11) 0.0144(4) Uani 1 1 d . . . C2 C 0.18289(13) 0.0226(3) 0.12989(12) 0.0164(5) Uani 1 1 d . . . C3 C 0.20341(14) 0.0844(4) 0.19203(12) 0.0185(5) Uani 1 1 d . . . H3 H 0.1690 0.1143 0.2252 0.022 Uiso 1 1 calc R . . C4 C 0.27691(15) 0.1019(3) 0.20505(11) 0.0175(5) Uani 1 1 d . . . C5 C 0.32807(14) 0.0634(4) 0.15873(11) 0.0165(5) Uani 1 1 d . . . H5 H 0.3772 0.0742 0.1697 0.020 Uiso 1 1 calc R . . C6 C 0.30663(13) 0.0066(3) 0.09371(11) 0.0144(4) Uani 1 1 d . . . C7 C 0.35701(13) -0.0214(3) 0.04182(11) 0.0160(4) Uani 1 1 d . . . H7 H 0.4065 -0.0074 0.0505 0.019 Uiso 1 1 calc R . . C8 C 0.33372(13) -0.0690(3) -0.02115(11) 0.0155(4) Uani 1 1 d . . . C9 C 0.25923(13) -0.1000(3) -0.02944(11) 0.0161(4) Uani 1 1 d . . . H9 H 0.2435 -0.1407 -0.0721 0.019 Uiso 1 1 calc R . . C10 C 0.38243(13) -0.0852(4) -0.07941(11) 0.0162(5) Uani 1 1 d . . . C11 C 0.42510(14) 0.0693(4) -0.09911(12) 0.0192(5) Uani 1 1 d . . . C12 C 0.46952(14) 0.0488(4) -0.15488(12) 0.0218(5) Uani 1 1 d . . . H12 H 0.4995 0.1502 -0.1679 0.026 Uiso 1 1 calc R . . C13 C 0.47036(14) -0.1169(4) -0.19126(12) 0.0221(5) Uani 1 1 d . . . H13 H 0.5008 -0.1275 -0.2290 0.027 Uiso 1 1 calc R . . C14 C 0.42744(14) -0.2674(4) -0.17346(13) 0.0237(5) Uani 1 1 d . . . H14 H 0.4279 -0.3806 -0.1987 0.028 Uiso 1 1 calc R . . C15 C 0.38354(14) -0.2493(4) -0.11770(13) 0.0212(5) Uani 1 1 d . . . H15 H 0.3536 -0.3515 -0.1054 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 0.01626(12) 0.02917(15) 0.02720(13) -0.00220(11) 0.00299(10) 0.00243(10) Br2 0.03519(15) 0.02364(13) 0.01045(10) -0.00058(9) -0.00098(10) 0.00143(11) N1 0.0178(10) 0.0172(10) 0.0143(9) 0.0002(7) -0.0003(7) 0.0005(8) N2 0.0539(19) 0.0242(13) 0.0429(16) -0.0093(11) 0.0316(14) -0.0147(13) C1 0.0165(11) 0.0131(11) 0.0136(9) 0.0019(8) -0.0010(8) -0.0007(8) C2 0.0162(11) 0.0157(11) 0.0171(10) 0.0018(8) 0.0027(8) 0.0010(9) C3 0.0238(13) 0.0163(11) 0.0154(10) 0.0014(8) 0.0032(9) 0.0034(10) C4 0.0266(13) 0.0154(11) 0.0104(9) 0.0004(8) -0.0001(9) 0.0010(10) C5 0.0184(11) 0.0188(12) 0.0122(10) 0.0012(8) -0.0003(8) -0.0010(9) C6 0.0184(11) 0.0128(10) 0.0119(9) 0.0014(8) -0.0002(8) -0.0012(9) C7 0.0159(11) 0.0164(11) 0.0157(10) -0.0001(8) -0.0008(8) -0.0001(9) C8 0.0181(11) 0.0162(11) 0.0121(9) 0.0013(8) 0.0024(8) 0.0001(9) C9 0.0203(12) 0.0144(11) 0.0135(9) -0.0012(8) -0.0002(9) -0.0004(9) C10 0.0163(12) 0.0204(12) 0.0120(9) 0.0026(8) 0.0010(8) 0.0015(9) C11 0.0214(13) 0.0200(12) 0.0163(10) 0.0003(9) 0.0039(9) -0.0002(9) C12 0.0206(13) 0.0256(13) 0.0191(11) 0.0014(10) 0.0054(10) -0.0027(10) C13 0.0173(12) 0.0351(15) 0.0139(10) -0.0010(10) 0.0018(9) 0.0021(11) C14 0.0215(13) 0.0292(14) 0.0206(11) -0.0103(10) 0.0017(10) 0.0002(11) C15 0.0209(12) 0.0218(12) 0.0210(11) -0.0031(10) 0.0052(10) -0.0013(10) _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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 1.7222(0.0175) x - 6.8233(0.0019) y + 5.2131(0.0188) z = 0.9624(0.0049) * -0.0249(0.0016) C1 * 0.0137(0.0016) N1 * 0.0091(0.0016) C6 * 0.0166(0.0017) C7 * -0.0271(0.0017) C8 * 0.0127(0.0017) C9 Rms deviation of fitted atoms = 0.0185 13.7819(0.0138) x - 2.4963(0.0074) y + 11.6189(0.0174) z = 4.5466(0.0077) Angle to previous plane(with approximate esd) = 56.20( 0.09 ) * 0.0140(0.0018) C10 * -0.0125(0.0019) C11 * 0.0029(0.0019) C12 * 0.0053(0.0019) C13 * -0.0037(0.0020) C14 * -0.0061(0.0019) C15 -0.0834(0.0049) N2 -0.1370(0.0411) H101 -0.2654(0.0391) H102 Rms deviation of fitted atoms = 0.0086 ; 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 C2 1.891(2) . ? Br2 C4 1.906(2) . ? N1 C9 1.318(3) . ? N1 C1 1.369(3) . ? N2 C11 1.387(4) . ? N2 H101 0.858(18) . ? N2 H102 0.857(18) . ? C1 C6 1.421(3) . ? C1 C2 1.427(3) . ? C2 C3 1.375(3) . ? C3 C4 1.408(4) . ? C3 H3 0.9500 . ? C4 C5 1.363(3) . ? C5 C6 1.422(3) . ? C5 H5 0.9500 . ? C6 C7 1.419(3) . ? C7 C8 1.378(3) . ? C7 H7 0.9500 . ? C8 C9 1.424(3) . ? C8 C10 1.487(3) . ? C9 H9 0.9500 . ? C10 C15 1.395(4) . ? C10 C11 1.414(4) . ? C11 C12 1.402(3) . ? C12 C13 1.384(4) . ? C12 H12 0.9500 . ? C13 C14 1.384(4) . ? C13 H13 0.9500 . ? C14 C15 1.394(4) . ? C14 H14 0.9500 . ? C15 H15 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 C9 N1 C1 117.1(2) . . ? C11 N2 H101 120(3) . . ? C11 N2 H102 122(3) . . ? H101 N2 H102 116(4) . . ? N1 C1 C6 122.3(2) . . ? N1 C1 C2 120.3(2) . . ? C6 C1 C2 117.4(2) . . ? C3 C2 C1 122.3(2) . . ? C3 C2 Br1 118.88(19) . . ? C1 C2 Br1 118.82(18) . . ? C2 C3 C4 118.0(2) . . ? C2 C3 H3 121.0 . . ? C4 C3 H3 121.0 . . ? C5 C4 C3 123.0(2) . . ? C5 C4 Br2 118.3(2) . . ? C3 C4 Br2 118.68(18) . . ? C4 C5 C6 118.8(2) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C7 C6 C1 118.0(2) . . ? C7 C6 C5 121.5(2) . . ? C1 C6 C5 120.4(2) . . ? C8 C7 C6 119.7(2) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 117.1(2) . . ? C7 C8 C10 122.9(2) . . ? C9 C8 C10 119.9(2) . . ? N1 C9 C8 125.6(2) . . ? N1 C9 H9 117.2 . . ? C8 C9 H9 117.2 . . ? C15 C10 C11 119.0(2) . . ? C15 C10 C8 120.4(2) . . ? C11 C10 C8 120.5(2) . . ? N2 C11 C12 119.8(2) . . ? N2 C11 C10 121.6(2) . . ? C12 C11 C10 118.6(2) . . ? C13 C12 C11 121.0(3) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 120.9(2) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C13 C14 C15 118.6(2) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? C14 C15 C10 121.8(3) . . ? C14 C15 H15 119.1 . . ? C10 C15 H15 119.1 . . ? 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 C9 N1 C1 C6 -3.5(3) . . . . ? C9 N1 C1 C2 175.4(2) . . . . ? N1 C1 C2 C3 -179.0(2) . . . . ? C6 C1 C2 C3 0.0(4) . . . . ? N1 C1 C2 Br1 2.5(3) . . . . ? C6 C1 C2 Br1 -178.52(17) . . . . ? C1 C2 C3 C4 -1.7(4) . . . . ? Br1 C2 C3 C4 176.79(18) . . . . ? C2 C3 C4 C5 1.0(4) . . . . ? C2 C3 C4 Br2 179.92(18) . . . . ? C3 C4 C5 C6 1.4(4) . . . . ? Br2 C4 C5 C6 -177.50(18) . . . . ? N1 C1 C6 C7 3.2(3) . . . . ? C2 C1 C6 C7 -175.8(2) . . . . ? N1 C1 C6 C5 -178.6(2) . . . . ? C2 C1 C6 C5 2.5(3) . . . . ? C4 C5 C6 C7 175.0(2) . . . . ? C4 C5 C6 C1 -3.2(4) . . . . ? C1 C6 C7 C8 0.9(3) . . . . ? C5 C6 C7 C8 -177.4(2) . . . . ? C6 C7 C8 C9 -4.1(3) . . . . ? C6 C7 C8 C10 174.8(2) . . . . ? C1 N1 C9 C8 -0.1(4) . . . . ? C7 C8 C9 N1 4.0(4) . . . . ? C10 C8 C9 N1 -175.0(2) . . . . ? C7 C8 C10 C15 126.3(3) . . . . ? C9 C8 C10 C15 -54.8(3) . . . . ? C7 C8 C10 C11 -57.4(3) . . . . ? C9 C8 C10 C11 121.4(3) . . . . ? C15 C10 C11 N2 175.7(3) . . . . ? C8 C10 C11 N2 -0.6(4) . . . . ? C15 C10 C11 C12 -2.8(4) . . . . ? C8 C10 C11 C12 -179.1(2) . . . . ? N2 C11 C12 C13 -176.7(3) . . . . ? C10 C11 C12 C13 1.8(4) . . . . ? C11 C12 C13 C14 -0.2(4) . . . . ? C12 C13 C14 C15 -0.4(4) . . . . ? C13 C14 C15 C10 -0.7(4) . . . . ? C11 C10 C15 C14 2.3(4) . . . . ? C8 C10 C15 C14 178.6(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 N2 H101 Br1 0.858(18) 2.95(3) 3.732(3) 152(3) 4 N2 H102 N1 0.857(18) 2.44(2) 3.262(3) 161(4) 8_665 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 31.84 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.748 _refine_diff_density_min -0.678 _refine_diff_density_rms 0.116 # Attachment '- compound 11p.cif' data_mv507 _database_code_depnum_ccdc_archive 'CCDC 828271' #TrackingRef '- compound 11p.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 Br2 N2' _chemical_formula_sum 'C16 H12 Br2 N2' _chemical_formula_weight 392.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 11.3993(12) _cell_length_b 20.292(2) _cell_length_c 6.8679(7) _cell_angle_alpha 90.00 _cell_angle_beta 116.348(2) _cell_angle_gamma 90.00 _cell_volume 1423.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5433 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 30.44 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.829 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 5.684 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.671 _exptl_absorpt_correction_T_max 0.865 _exptl_absorpt_process_details 'Bruker SAINT (SADABS)' _exptl_special_details ; All H atoms observed on difference Fourier map. ; _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 8280 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0558 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 30.58 _reflns_number_total 4192 _reflns_number_gt 3845 _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^)+(0.0000P)^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 4192 _refine_ls_number_parameters 186 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0304 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0530 _refine_ls_wR_factor_gt 0.0517 _refine_ls_goodness_of_fit_ref 0.881 _refine_ls_restrained_S_all 0.881 _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 0.17717(2) -0.145867(11) 0.10539(3) 0.02082(6) Uani 1 1 d . . . Br2 Br -0.17758(3) 0.065496(14) -0.10468(4) 0.02654(7) Uani 1 1 d . . . N1 N 0.3765(2) -0.03376(10) 0.1990(3) 0.0167(4) Uani 1 1 d . . . N2 N 0.5042(3) 0.16956(14) 0.6149(4) 0.0317(6) Uani 1 1 d . . . H2N H 0.460(3) 0.1388(15) 0.589(5) 0.026(8) Uiso 1 1 d . . . C1 C 0.2530(2) -0.00969(12) 0.1350(4) 0.0146(4) Uani 1 1 d . . . C2 C 0.1458(2) -0.05421(11) 0.0796(4) 0.0169(5) Uani 1 1 d . . . C3 C 0.0208(2) -0.03244(13) 0.0138(4) 0.0181(5) Uani 1 1 d . . . H3 H -0.0490 -0.0628 -0.0200 0.022 Uiso 1 1 calc R . . C4 C -0.0029(3) 0.03592(14) -0.0031(4) 0.0176(4) Uani 1 1 d . . . C5 C 0.0953(2) 0.08090(13) 0.0495(4) 0.0174(5) Uani 1 1 d . . . H5 H 0.0765 0.1268 0.0364 0.021 Uiso 1 1 calc R . . C6 C 0.2255(2) 0.05834(12) 0.1240(4) 0.0155(5) Uani 1 1 d . . . C7 C 0.3320(3) 0.10228(12) 0.1934(4) 0.0166(5) Uani 1 1 d . . . H7 H 0.3169 0.1484 0.1871 0.020 Uiso 1 1 calc R . . C8 C 0.4572(2) 0.07875(12) 0.2699(4) 0.0159(4) Uani 1 1 d . . . C9 C 0.4721(2) 0.00969(12) 0.2615(4) 0.0167(5) Uani 1 1 d . . . H9 H 0.5582 -0.0067 0.3044 0.020 Uiso 1 1 calc R . . C10 C 0.5892(3) 0.16925(13) 0.5214(4) 0.0210(5) Uani 1 1 d . . . C11 C 0.5726(2) 0.12401(12) 0.3555(4) 0.0180(5) Uani 1 1 d . . . C12 C 0.6629(3) 0.12170(13) 0.2719(5) 0.0222(5) Uani 1 1 d . . . H12 H 0.6525 0.0902 0.1630 0.027 Uiso 1 1 calc R . . C13 C 0.7690(3) 0.16493(15) 0.3451(5) 0.0267(6) Uani 1 1 d . . . H13 H 0.8308 0.1628 0.2875 0.032 Uiso 1 1 calc R . . C14 C 0.7829(3) 0.21049(13) 0.5012(5) 0.0247(6) Uani 1 1 d . . . H14 H 0.8543 0.2405 0.5504 0.030 Uiso 1 1 calc R . . C15 C 0.6941(3) 0.21347(13) 0.5885(5) 0.0233(6) Uani 1 1 d . . . H15 H 0.7046 0.2459 0.6949 0.028 Uiso 1 1 calc R . . C16 C 0.5170(3) 0.21566(15) 0.7818(5) 0.0305(7) Uani 1 1 d . . . H16A H 0.6038 0.2110 0.9051 0.046 Uiso 1 1 calc R . . H16B H 0.4495 0.2068 0.8301 0.046 Uiso 1 1 calc R . . H16C H 0.5066 0.2606 0.7243 0.046 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 0.02286(12) 0.01479(10) 0.02493(12) -0.00290(10) 0.01072(9) -0.00268(10) Br2 0.01664(12) 0.03052(15) 0.03208(14) 0.00085(12) 0.01045(10) 0.00342(12) N1 0.0195(10) 0.0164(10) 0.0162(10) -0.0018(8) 0.0098(8) 0.0007(8) N2 0.0397(15) 0.0304(13) 0.0411(15) -0.0199(11) 0.0325(13) -0.0205(12) C1 0.0162(11) 0.0201(12) 0.0095(10) -0.0010(9) 0.0073(8) -0.0023(9) C2 0.0224(12) 0.0146(10) 0.0151(11) -0.0029(9) 0.0098(10) -0.0028(9) C3 0.0164(12) 0.0238(13) 0.0148(11) -0.0013(9) 0.0076(9) -0.0023(10) C4 0.0169(10) 0.0229(12) 0.0145(10) 0.0008(8) 0.0085(9) 0.0040(9) C5 0.0193(12) 0.0177(12) 0.0157(11) 0.0019(9) 0.0081(9) 0.0040(9) C6 0.0192(12) 0.0175(12) 0.0118(11) 0.0014(9) 0.0086(9) 0.0012(9) C7 0.0222(12) 0.0132(11) 0.0171(11) 0.0007(9) 0.0113(10) 0.0013(9) C8 0.0210(12) 0.0148(11) 0.0159(11) -0.0014(9) 0.0118(9) -0.0011(9) C9 0.0157(11) 0.0196(12) 0.0177(12) -0.0001(9) 0.0102(9) 0.0005(9) C10 0.0222(13) 0.0189(12) 0.0266(13) 0.0008(10) 0.0152(11) -0.0009(10) C11 0.0188(11) 0.0155(11) 0.0218(12) 0.0012(9) 0.0108(10) -0.0001(9) C12 0.0240(13) 0.0193(12) 0.0285(13) -0.0002(11) 0.0163(11) 0.0005(10) C13 0.0220(13) 0.0233(13) 0.0416(17) 0.0004(12) 0.0204(13) -0.0021(11) C14 0.0217(13) 0.0189(12) 0.0360(15) -0.0006(11) 0.0151(12) -0.0032(10) C15 0.0262(14) 0.0155(12) 0.0311(14) -0.0021(11) 0.0154(11) -0.0045(10) C16 0.0333(16) 0.0313(15) 0.0343(16) -0.0161(12) 0.0218(14) -0.0122(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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 3.8400(0.0048) x + 0.4849(0.0136) y - 6.8197(0.0008) z = 0.0216(0.0014) * 0.0507 (0.0017) N1 * 0.0246 (0.0020) C1 * -0.0310 (0.0020) C2 * -0.0517 (0.0021) C3 * 0.0058 (0.0021) C4 * 0.0458 (0.0019) C5 * 0.0269 (0.0022) C6 * -0.0160 (0.0019) C7 * -0.0681 (0.0018) C8 * 0.0130 (0.0019) C9 -0.1307 (0.0024) Br1 0.0422 (0.0023) Br2 -0.1872 (0.0033) C11 Rms deviation of fitted atoms = 0.0384 3.0775(0.0124) x - 13.2974(0.0175) y + 3.5189(0.0069) z = 1.3783(0.0085) Angle to previous plane (with approximate esd) = 53.93 ( 0.08 ) * 0.0192 (0.0019) C10 * -0.0144 (0.0018) C11 * 0.0002 (0.0020) C12 * 0.0094 (0.0021) C13 * -0.0043 (0.0020) C14 * -0.0101 (0.0020) C15 0.0824 (0.0046) N2 0.0963 (0.0057) C16 -0.0687 (0.0041) C8 Rms deviation of fitted atoms = 0.0114 ; 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 C2 1.887(2) . ? Br2 C4 1.892(3) . ? N1 C9 1.317(3) . ? N1 C1 1.365(3) . ? N2 C10 1.380(3) . ? N2 C16 1.436(3) . ? N2 H2N 0.77(3) . ? C1 C6 1.410(3) . ? C1 C2 1.429(3) . ? C2 C3 1.363(3) . ? C3 C4 1.408(4) . ? C3 H3 0.9500 . ? C4 C5 1.363(4) . ? C5 C6 1.415(4) . ? C5 H5 0.9500 . ? C6 C7 1.407(3) . ? C7 C8 1.370(4) . ? C7 H7 0.9500 . ? C8 C9 1.416(3) . ? C8 C11 1.494(3) . ? C9 H9 0.9500 . ? C10 C15 1.399(4) . ? C10 C11 1.409(4) . ? C11 C12 1.385(3) . ? C12 C13 1.395(4) . ? C12 H12 0.9500 . ? C13 C14 1.371(4) . ? C13 H13 0.9500 . ? C14 C15 1.387(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 C9 N1 C1 116.9(2) . . ? C10 N2 C16 122.1(2) . . ? C10 N2 H2N 114(2) . . ? C16 N2 H2N 122(2) . . ? N1 C1 C6 122.7(2) . . ? N1 C1 C2 119.8(2) . . ? C6 C1 C2 117.5(2) . . ? C3 C2 C1 121.9(2) . . ? C3 C2 Br1 118.51(18) . . ? C1 C2 Br1 119.59(18) . . ? C2 C3 C4 118.7(2) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 122.2(2) . . ? C5 C4 Br2 119.4(2) . . ? C3 C4 Br2 118.4(2) . . ? C4 C5 C6 119.1(2) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C7 C6 C1 117.7(2) . . ? C7 C6 C5 121.7(2) . . ? C1 C6 C5 120.6(2) . . ? C8 C7 C6 120.3(2) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 116.9(2) . . ? C7 C8 C11 121.5(2) . . ? C9 C8 C11 121.6(2) . . ? N1 C9 C8 125.4(2) . . ? N1 C9 H9 117.3 . . ? C8 C9 H9 117.3 . . ? N2 C10 C15 121.2(2) . . ? N2 C10 C11 120.6(2) . . ? C15 C10 C11 118.2(2) . . ? C12 C11 C10 120.0(2) . . ? C12 C11 C8 120.2(2) . . ? C10 C11 C8 119.9(2) . . ? C11 C12 C13 121.0(3) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C14 C13 C12 119.1(3) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C15 120.9(2) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C14 C15 C10 120.7(3) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? N2 C16 H16A 109.5 . . ? N2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 C9 N1 C1 C6 3.2(3) . . . . ? C9 N1 C1 C2 -175.7(2) . . . . ? N1 C1 C2 C3 -179.7(2) . . . . ? C6 C1 C2 C3 1.4(3) . . . . ? N1 C1 C2 Br1 2.2(3) . . . . ? C6 C1 C2 Br1 -176.73(17) . . . . ? C1 C2 C3 C4 1.1(4) . . . . ? Br1 C2 C3 C4 179.23(19) . . . . ? C2 C3 C4 C5 -1.8(4) . . . . ? C2 C3 C4 Br2 177.73(18) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? Br2 C4 C5 C6 -179.60(18) . . . . ? N1 C1 C6 C7 -3.4(3) . . . . ? C2 C1 C6 C7 175.5(2) . . . . ? N1 C1 C6 C5 177.8(2) . . . . ? C2 C1 C6 C5 -3.3(3) . . . . ? C4 C5 C6 C7 -176.1(2) . . . . ? C4 C5 C6 C1 2.7(4) . . . . ? C1 C6 C7 C8 -0.5(3) . . . . ? C5 C6 C7 C8 178.3(2) . . . . ? C6 C7 C8 C9 4.0(3) . . . . ? C6 C7 C8 C11 -176.7(2) . . . . ? C1 N1 C9 C8 0.8(3) . . . . ? C7 C8 C9 N1 -4.4(4) . . . . ? C11 C8 C9 N1 176.3(2) . . . . ? C16 N2 C10 C15 1.2(5) . . . . ? C16 N2 C10 C11 -179.0(3) . . . . ? N2 C10 C11 C12 -176.3(3) . . . . ? C15 C10 C11 C12 3.6(4) . . . . ? N2 C10 C11 C8 3.9(4) . . . . ? C15 C10 C11 C8 -176.3(2) . . . . ? C7 C8 C11 C12 -125.7(3) . . . . ? C9 C8 C11 C12 53.4(3) . . . . ? C7 C8 C11 C10 54.1(3) . . . . ? C9 C8 C11 C10 -126.7(2) . . . . ? C10 C11 C12 C13 -1.8(4) . . . . ? C8 C11 C12 C13 178.0(3) . . . . ? C11 C12 C13 C14 -0.4(4) . . . . ? C12 C13 C14 C15 0.8(4) . . . . ? C13 C14 C15 C10 1.0(4) . . . . ? N2 C10 C15 C14 176.7(3) . . . . ? C11 C10 C15 C14 -3.2(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N N1 0.77(3) 2.58(3) 3.285(3) 153(3) 2 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.58 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.622 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.080 # Attachment '- compound 6b.cif' data_mv600 _database_code_depnum_ccdc_archive 'CCDC 828272' #TrackingRef '- compound 6b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H11 Br N2' _chemical_formula_weight 311.18 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' 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.7179(3) _cell_length_b 13.9491(9) _cell_length_c 18.8428(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1240.05(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5152 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 31.49 _exptl_crystal_description rod _exptl_crystal_colour orange _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.667 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 3.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5441 _exptl_absorpt_correction_T_max 0.9369 _exptl_absorpt_process_details 'Bruker SAINT (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 9861 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 31.53 _reflns_number_total 4066 _reflns_number_gt 3771 _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^+0.1000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.003(9) _refine_ls_number_reflns 4066 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0743 _refine_ls_wR_factor_gt 0.0722 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 0.97452(5) 0.828829(15) 0.041827(10) 0.01645(6) Uani 1 1 d . . . N1 N 0.3767(4) 1.05715(15) 0.27114(10) 0.0155(4) Uani 1 1 d . . . N2 N 0.0195(5) 0.99791(12) 0.34907(9) 0.0148(4) Uani 1 1 d . . . C1 C 0.2079(5) 0.98904(16) 0.29479(11) 0.0129(4) Uani 1 1 d . . . C2 C 0.5271(5) 1.01250(15) 0.21595(10) 0.0138(4) Uani 1 1 d . . . C3 C 0.7380(5) 1.05403(17) 0.17374(12) 0.0165(5) Uani 1 1 d . . . H3 H 0.7926 1.1189 0.1806 0.020 Uiso 1 1 calc R . . C4 C 0.8660(5) 0.99823(17) 0.12151(11) 0.0151(4) Uani 1 1 d . . . H4 H 1.0093 1.0251 0.0922 0.018 Uiso 1 1 calc R . . C5 C 0.7841(5) 0.90263(17) 0.11196(11) 0.0147(4) Uani 1 1 d . . . C6 C 0.5768(5) 0.85937(16) 0.15302(11) 0.0139(4) Uani 1 1 d . . . H6 H 0.5242 0.7943 0.1460 0.017 Uiso 1 1 calc R . . C7 C 0.4486(5) 0.91557(15) 0.20519(11) 0.0133(4) Uani 1 1 d . . . C8 C 0.2339(5) 0.89696(17) 0.25803(11) 0.0129(4) Uani 1 1 d . . . C9 C 0.0719(5) 0.82153(16) 0.27707(10) 0.0142(4) Uani 1 1 d . . . H9 H 0.0845 0.7628 0.2518 0.017 Uiso 1 1 calc R . . C10 C -0.1191(5) 0.83065(17) 0.33564(10) 0.0141(4) Uani 1 1 d . . . C11 C -0.2864(5) 0.75312(17) 0.35887(12) 0.0159(4) Uani 1 1 d . . . H11 H -0.2738 0.6933 0.3350 0.019 Uiso 1 1 calc R . . C12 C -0.4685(6) 0.76282(17) 0.41576(11) 0.0184(4) Uani 1 1 d . . . H12 H -0.5789 0.7099 0.4313 0.022 Uiso 1 1 calc R . . C13 C -0.4892(5) 0.85131(16) 0.45027(11) 0.0192(4) Uani 1 1 d . . . H13 H -0.6137 0.8577 0.4896 0.023 Uiso 1 1 calc R . . C14 C -0.3326(5) 0.92948(19) 0.42846(12) 0.0190(5) Uani 1 1 d . . . H14 H -0.3524 0.9892 0.4522 0.023 Uiso 1 1 calc R . . C15 C -0.1430(5) 0.92062(16) 0.37088(11) 0.0135(4) Uani 1 1 d . . . C16 C -0.0107(6) 1.09172(15) 0.38298(12) 0.0212(5) Uani 1 1 d . . . H16A H -0.2050 1.1150 0.3766 0.032 Uiso 1 1 calc R . . H16B H 0.1223 1.1371 0.3613 0.032 Uiso 1 1 calc R . . H16C H 0.0305 1.0859 0.4338 0.032 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 0.01754(11) 0.01767(10) 0.01414(9) -0.00147(8) 0.00121(8) 0.00067(9) N1 0.0154(10) 0.0145(9) 0.0167(8) -0.0001(7) -0.0011(7) -0.0002(8) N2 0.0156(10) 0.0142(8) 0.0147(7) -0.0033(6) 0.0003(8) -0.0025(8) C1 0.0112(11) 0.0133(10) 0.0143(9) -0.0013(8) -0.0031(8) 0.0003(8) C2 0.0126(11) 0.0135(9) 0.0154(8) 0.0015(7) -0.0042(8) 0.0021(9) C3 0.0171(12) 0.0148(10) 0.0176(10) 0.0015(8) -0.0016(9) 0.0003(9) C4 0.0146(11) 0.0175(11) 0.0131(9) 0.0025(8) -0.0004(8) -0.0007(9) C5 0.0151(11) 0.0163(11) 0.0127(9) 0.0005(8) -0.0020(8) 0.0026(9) C6 0.0141(11) 0.0135(9) 0.0141(8) -0.0008(7) -0.0023(8) 0.0002(8) C7 0.0119(11) 0.0135(9) 0.0144(8) 0.0020(7) -0.0021(8) 0.0003(8) C8 0.0119(11) 0.0136(10) 0.0132(9) 0.0008(8) -0.0010(8) 0.0007(8) C9 0.0141(10) 0.0126(9) 0.0159(8) 0.0007(8) -0.0023(7) 0.0018(9) C10 0.0121(10) 0.0156(10) 0.0147(8) 0.0018(9) -0.0019(7) 0.0014(9) C11 0.0141(11) 0.0145(10) 0.0190(10) 0.0032(8) -0.0014(8) 0.0005(9) C12 0.0163(11) 0.0200(10) 0.0189(9) 0.0052(8) -0.0005(9) -0.0019(10) C13 0.0169(11) 0.0249(10) 0.0160(8) 0.0016(8) 0.0012(9) -0.0001(9) C14 0.0199(13) 0.0221(12) 0.0150(10) 0.0000(9) 0.0011(9) -0.0006(10) C15 0.0112(10) 0.0158(10) 0.0134(9) 0.0031(8) -0.0008(8) -0.0009(8) C16 0.0242(14) 0.0159(10) 0.0235(10) -0.0068(8) 0.0062(11) -0.0014(11) _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 C5 1.901(2) . ? N1 C1 1.317(3) . ? N1 C2 1.405(3) . ? N2 C1 1.361(3) . ? N2 C15 1.385(3) . ? N2 C16 1.463(3) . ? C1 C8 1.464(3) . ? C2 C3 1.399(3) . ? C2 C7 1.416(3) . ? C3 C4 1.393(3) . ? C3 H3 0.9500 . ? C4 C5 1.400(3) . ? C4 H4 0.9500 . ? C5 C6 1.385(3) . ? C6 C7 1.395(3) . ? C6 H6 0.9500 . ? C7 C8 1.444(3) . ? C8 C9 1.349(3) . ? C9 C10 1.430(3) . ? C9 H9 0.9500 . ? C10 C11 1.409(3) . ? C10 C15 1.424(3) . ? C11 C12 1.380(3) . ? C11 H11 0.9500 . ? C12 C13 1.399(3) . ? C12 H12 0.9500 . ? C13 C14 1.380(3) . ? C13 H13 0.9500 . ? C14 C15 1.412(3) . ? C14 H14 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 C1 N1 C2 103.66(19) . . ? C1 N2 C15 120.90(18) . . ? C1 N2 C16 118.24(19) . . ? C15 N2 C16 120.85(19) . . ? N1 C1 N2 125.7(2) . . ? N1 C1 C8 114.9(2) . . ? N2 C1 C8 119.35(19) . . ? C3 C2 N1 126.6(2) . . ? C3 C2 C7 120.0(2) . . ? N1 C2 C7 113.4(2) . . ? C4 C3 C2 118.6(2) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C5 120.2(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 122.5(2) . . ? C6 C5 Br1 119.08(17) . . ? C4 C5 Br1 118.34(17) . . ? C5 C6 C7 117.0(2) . . ? C5 C6 H6 121.5 . . ? C7 C6 H6 121.5 . . ? C6 C7 C2 121.6(2) . . ? C6 C7 C8 133.5(2) . . ? C2 C7 C8 104.85(19) . . ? C9 C8 C7 136.1(2) . . ? C9 C8 C1 120.7(2) . . ? C7 C8 C1 103.14(19) . . ? C8 C9 C10 119.5(2) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C11 C10 C15 119.2(2) . . ? C11 C10 C9 121.6(2) . . ? C15 C10 C9 119.2(2) . . ? C12 C11 C10 121.0(2) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 119.4(2) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C14 C13 C12 121.5(2) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C15 119.9(2) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? N2 C15 C14 120.7(2) . . ? N2 C15 C10 120.3(2) . . ? C14 C15 C10 119.0(2) . . ? N2 C16 H16A 109.5 . . ? N2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 C2 N1 C1 N2 179.7(2) . . . . ? C2 N1 C1 C8 0.0(3) . . . . ? C15 N2 C1 N1 -178.3(2) . . . . ? C16 N2 C1 N1 2.8(3) . . . . ? C15 N2 C1 C8 1.4(3) . . . . ? C16 N2 C1 C8 -177.5(2) . . . . ? C1 N1 C2 C3 -179.1(2) . . . . ? C1 N1 C2 C7 0.3(3) . . . . ? N1 C2 C3 C4 179.6(2) . . . . ? C7 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 C6 -0.1(3) . . . . ? C3 C4 C5 Br1 -178.07(17) . . . . ? C4 C5 C6 C7 0.2(3) . . . . ? Br1 C5 C6 C7 178.18(16) . . . . ? C5 C6 C7 C2 -0.2(3) . . . . ? C5 C6 C7 C8 -178.7(2) . . . . ? C3 C2 C7 C6 0.0(3) . . . . ? N1 C2 C7 C6 -179.5(2) . . . . ? C3 C2 C7 C8 178.9(2) . . . . ? N1 C2 C7 C8 -0.6(3) . . . . ? C6 C7 C8 C9 -1.5(5) . . . . ? C2 C7 C8 C9 179.7(3) . . . . ? C6 C7 C8 C1 179.3(2) . . . . ? C2 C7 C8 C1 0.5(2) . . . . ? N1 C1 C8 C9 -179.7(2) . . . . ? N2 C1 C8 C9 0.5(3) . . . . ? N1 C1 C8 C7 -0.4(3) . . . . ? N2 C1 C8 C7 179.9(2) . . . . ? C7 C8 C9 C10 178.4(2) . . . . ? C1 C8 C9 C10 -2.5(3) . . . . ? C8 C9 C10 C11 -178.1(2) . . . . ? C8 C9 C10 C15 2.6(3) . . . . ? C15 C10 C11 C12 -1.1(3) . . . . ? C9 C10 C11 C12 179.6(2) . . . . ? C10 C11 C12 C13 0.7(4) . . . . ? C11 C12 C13 C14 0.4(4) . . . . ? C12 C13 C14 C15 -1.1(4) . . . . ? C1 N2 C15 C14 178.3(2) . . . . ? C16 N2 C15 C14 -2.8(3) . . . . ? C1 N2 C15 C10 -1.3(3) . . . . ? C16 N2 C15 C10 177.6(2) . . . . ? C13 C14 C15 N2 -178.9(2) . . . . ? C13 C14 C15 C10 0.7(3) . . . . ? C11 C10 C15 N2 179.9(2) . . . . ? C9 C10 C15 N2 -0.7(3) . . . . ? C11 C10 C15 C14 0.4(3) . . . . ? C9 C10 C15 C14 179.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 31.53 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.624 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.089