# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Guang-Xiang Liu' _publ_contact_author_email LIUGX@LIVE.COM _publ_section_title ; A Series of Novel Ion-pair Complexes Based on TCNQ: Syntheses, Crystal Structures and Properties ; loop_ _publ_author_name 'Guang-Xiang Liu' 'Xiao-Ming Ren' 'Wei-Yin Sum' 'Heng Xu' #========================================================= data_TQ1 _database_code_depnum_ccdc_archive 'CCDC 674961' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H11 Cl N, 1.5(C12 H4 N4)' _chemical_formula_sum 'C30 H17 Cl N7' _chemical_formula_weight 510.96 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' Cl Cl 0.1484 0.1585 '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 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 7.666(2) _cell_length_b 11.987(3) _cell_length_c 13.808(4) _cell_angle_alpha 82.236(4) _cell_angle_beta 88.974(4) _cell_angle_gamma 86.329(4) _cell_volume 1254.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2129 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 26.94 _exptl_crystal_description block _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 526 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9531 _exptl_absorpt_correction_T_max 0.9779 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Aepex 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 6207 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0560 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4333 _reflns_number_gt 3135 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, 1998.' _computing_cell_refinement 'SAINT-PLUS, Ver. 6.0, 1997' _computing_data_reduction 'SAINT-PLUS, Ver. 6.0, 1997' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, Ver. 6.10, Bruker AXS Inc., 2000.' _computing_publication_material 'SHELXTL-Bruker AXS Inc., 1998.' _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^)+(0.1281P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4333 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0846 _refine_ls_R_factor_gt 0.0671 _refine_ls_wR_factor_ref 0.1942 _refine_ls_wR_factor_gt 0.1744 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0881(4) 0.65882(19) -0.01261(18) 0.0441(6) Uani 1 1 d . . . C2 C 1.1676(4) 0.6314(2) -0.0979(2) 0.0505(7) Uani 1 1 d . . . H2 H 1.2880 0.6339 -0.1062 0.061 Uiso 1 1 calc R . . C3 C 1.0679(4) 0.6006(2) -0.1697(2) 0.0567(8) Uani 1 1 d . . . H3 H 1.1204 0.5825 -0.2273 0.068 Uiso 1 1 calc R . . C4 C 0.8904(4) 0.5962(2) -0.15713(19) 0.0549(7) Uani 1 1 d . . . H4 H 0.8241 0.5742 -0.2062 0.066 Uiso 1 1 calc R . . C5 C 0.8091(4) 0.6237(2) -0.0738(2) 0.0507(7) Uani 1 1 d . . . H5 H 0.6886 0.6204 -0.0666 0.061 Uiso 1 1 calc R . . C6 C 0.9084(3) 0.65727(19) 0.00164(17) 0.0413(6) Uani 1 1 d . . . C7 C 0.8194(4) 0.6905(2) 0.09214(19) 0.0528(7) Uani 1 1 d . . . H7A H 0.7007 0.6664 0.0956 0.063 Uiso 1 1 calc R . . H7B H 0.8810 0.6531 0.1495 0.063 Uiso 1 1 calc R . . C8 C 0.7443(3) 0.8844(2) 0.01519(19) 0.0532(7) Uani 1 1 d . . . H8 H 0.6982 0.8539 -0.0365 0.064 Uiso 1 1 calc R . . C9 C 0.7390(4) 0.9984(2) 0.0134(2) 0.0592(8) Uani 1 1 d . . . H9 H 0.6913 1.0460 -0.0396 0.071 Uiso 1 1 calc R . . C10 C 0.8050(4) 1.0425(2) 0.0913(2) 0.0570(8) Uani 1 1 d . . . H10 H 0.8028 1.1202 0.0909 0.068 Uiso 1 1 calc R . . C11 C 0.8735(4) 0.9722(2) 0.1687(2) 0.0567(7) Uani 1 1 d . . . H11 H 0.9168 1.0012 0.2220 0.068 Uiso 1 1 calc R . . C12 C 0.8780(4) 0.8581(2) 0.16706(18) 0.0526(7) Uani 1 1 d . . . H12 H 0.9250 0.8096 0.2197 0.063 Uiso 1 1 calc R . . C13 C 0.4291(3) 0.1910(2) 0.25867(19) 0.0456(6) Uani 1 1 d . . . C14 C 0.1624(3) 0.1876(2) 0.35037(17) 0.0456(6) Uani 1 1 d . . . C15 C 0.3395(3) 0.2148(2) 0.34531(16) 0.0395(6) Uani 1 1 d . . . C16 C 0.4199(3) 0.26609(19) 0.41654(16) 0.0362(5) Uani 1 1 d . . . C17 C 0.5993(3) 0.29058(19) 0.41000(16) 0.0368(6) Uani 1 1 d . . . H17 H 0.6656 0.2725 0.3566 0.044 Uiso 1 1 calc R . . C18 C 0.6757(3) 0.3398(2) 0.47997(16) 0.0376(6) Uani 1 1 d . . . H18 H 0.7933 0.3546 0.4737 0.045 Uiso 1 1 calc R . . C19 C 0.5791(3) 0.36923(19) 0.56258(16) 0.0365(5) Uani 1 1 d . . . C20 C 0.3987(3) 0.3460(2) 0.56869(17) 0.0407(6) Uani 1 1 d . . . H20 H 0.3323 0.3659 0.6214 0.049 Uiso 1 1 calc R . . C21 C 0.3211(3) 0.2955(2) 0.49956(17) 0.0399(6) Uani 1 1 d . . . H21 H 0.2038 0.2802 0.5062 0.048 Uiso 1 1 calc R . . C22 C 0.6553(3) 0.4209(2) 0.63521(17) 0.0413(6) Uani 1 1 d . . . C23 C 0.8374(4) 0.4399(3) 0.6347(2) 0.0577(8) Uani 1 1 d . . . C24 C 0.5559(3) 0.4560(2) 0.71500(18) 0.0454(6) Uani 1 1 d . . . C25 C 0.8509(3) 0.1333(2) 0.62442(16) 0.0396(6) Uani 1 1 d . . . C26 C 0.5938(3) 0.1351(2) 0.72517(17) 0.0399(6) Uani 1 1 d . . . C27 C 0.6731(3) 0.10744(18) 0.63770(15) 0.0329(5) Uani 1 1 d . . . C28 C 0.5875(3) 0.05275(17) 0.56941(15) 0.0303(5) Uani 1 1 d . . . C29 C 0.6746(3) 0.02323(18) 0.48440(15) 0.0316(5) Uani 1 1 d . . . H29 H 0.7911 0.0391 0.4739 0.038 Uiso 1 1 calc R . . C30 C 0.4081(3) 0.02780(18) 0.58232(16) 0.0319(5) Uani 1 1 d . . . H30 H 0.3471 0.0468 0.6372 0.038 Uiso 1 1 calc R . . Cl1 Cl 1.21862(10) 0.69733(6) 0.07759(5) 0.0646(3) Uani 1 1 d . . . N1 N 0.8160(3) 0.81544(17) 0.09136(14) 0.0435(5) Uani 1 1 d . . . N2 N 0.4940(3) 0.1729(2) 0.18676(18) 0.0655(7) Uani 1 1 d . . . N3 N 0.0194(3) 0.1643(2) 0.35071(19) 0.0700(7) Uani 1 1 d . . . N4 N 0.9814(4) 0.4542(3) 0.6384(2) 0.0990(12) Uani 1 1 d . . . N5 N 0.4796(3) 0.4858(2) 0.77945(18) 0.0628(7) Uani 1 1 d . . . N6 N 0.9944(3) 0.1551(2) 0.61541(16) 0.0581(6) Uani 1 1 d . . . N7 N 0.5321(3) 0.1592(2) 0.79679(15) 0.0587(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0546(17) 0.0321(12) 0.0456(14) -0.0041(10) -0.0099(12) -0.0016(11) C2 0.0542(18) 0.0390(14) 0.0577(16) -0.0061(12) 0.0000(13) 0.0001(12) C3 0.078(2) 0.0428(15) 0.0485(16) -0.0073(12) 0.0010(15) 0.0029(14) C4 0.074(2) 0.0451(15) 0.0465(15) -0.0099(12) -0.0147(14) -0.0004(14) C5 0.0546(17) 0.0410(14) 0.0578(16) -0.0097(12) -0.0068(13) -0.0059(12) C6 0.0475(16) 0.0317(12) 0.0444(14) -0.0032(10) -0.0021(11) -0.0031(11) C7 0.0687(19) 0.0426(14) 0.0467(15) -0.0019(11) 0.0027(13) -0.0110(13) C8 0.0530(17) 0.0621(18) 0.0436(14) -0.0078(12) -0.0023(12) 0.0051(13) C9 0.0600(19) 0.0584(18) 0.0543(17) 0.0008(13) 0.0042(14) 0.0139(14) C10 0.0608(19) 0.0447(15) 0.0651(18) -0.0105(13) 0.0197(15) 0.0005(13) C11 0.0606(19) 0.0563(17) 0.0557(17) -0.0165(13) 0.0043(14) -0.0062(14) C12 0.0582(18) 0.0573(17) 0.0419(14) -0.0082(12) -0.0020(12) 0.0018(13) C13 0.0393(15) 0.0557(16) 0.0420(14) -0.0073(12) -0.0087(11) -0.0004(12) C14 0.0379(16) 0.0569(16) 0.0400(13) 0.0017(11) -0.0075(11) -0.0033(12) C15 0.0358(14) 0.0454(14) 0.0351(12) 0.0016(10) -0.0023(10) 0.0009(10) C16 0.0306(13) 0.0391(13) 0.0365(12) 0.0032(10) -0.0027(10) -0.0008(10) C17 0.0302(13) 0.0440(13) 0.0349(12) -0.0012(10) 0.0054(10) -0.0029(10) C18 0.0263(12) 0.0469(14) 0.0388(12) -0.0022(10) 0.0020(10) -0.0048(10) C19 0.0328(13) 0.0365(12) 0.0384(12) 0.0001(10) 0.0024(10) -0.0010(10) C20 0.0372(14) 0.0445(14) 0.0396(13) -0.0044(10) 0.0046(10) 0.0005(11) C21 0.0291(13) 0.0475(14) 0.0412(13) 0.0002(10) 0.0030(10) -0.0024(10) C22 0.0384(14) 0.0450(14) 0.0410(13) -0.0086(10) -0.0038(10) -0.0004(11) C23 0.0409(18) 0.079(2) 0.0617(18) -0.0385(15) 0.0005(13) -0.0050(14) C24 0.0439(16) 0.0464(15) 0.0466(15) -0.0082(12) -0.0032(12) -0.0033(12) C25 0.0426(16) 0.0456(14) 0.0314(12) -0.0073(10) -0.0078(10) -0.0028(11) C26 0.0393(14) 0.0468(14) 0.0349(13) -0.0069(11) -0.0063(10) -0.0088(11) C27 0.0296(13) 0.0379(12) 0.0317(11) -0.0042(9) -0.0023(9) -0.0058(10) C28 0.0274(12) 0.0328(12) 0.0299(11) -0.0012(9) -0.0007(9) -0.0030(9) C29 0.0231(12) 0.0375(12) 0.0342(12) -0.0046(9) 0.0007(9) -0.0035(9) C30 0.0261(12) 0.0378(12) 0.0319(11) -0.0056(9) 0.0027(9) -0.0027(9) Cl1 0.0669(6) 0.0628(5) 0.0662(5) -0.0121(4) -0.0240(4) -0.0058(4) N1 0.0468(13) 0.0457(12) 0.0381(11) -0.0081(9) 0.0028(9) 0.0007(9) N2 0.0575(16) 0.0907(19) 0.0500(15) -0.0196(13) 0.0016(12) 0.0033(13) N3 0.0474(16) 0.092(2) 0.0691(17) 0.0010(14) -0.0085(13) -0.0144(14) N4 0.0445(18) 0.158(3) 0.114(3) -0.087(2) 0.0023(16) -0.0155(18) N5 0.0599(16) 0.0727(17) 0.0576(15) -0.0196(12) 0.0068(12) 0.0018(12) N6 0.0345(14) 0.0891(18) 0.0536(14) -0.0130(12) -0.0044(10) -0.0177(12) N7 0.0616(16) 0.0800(17) 0.0388(13) -0.0205(11) 0.0057(11) -0.0144(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.386(4) . ? C1 C6 1.389(4) . ? C1 Cl1 1.739(3) . ? C2 C3 1.366(4) . ? C2 H2 0.9300 . ? C3 C4 1.372(4) . ? C3 H3 0.9300 . ? C4 C5 1.368(4) . ? C4 H4 0.9300 . ? C5 C6 1.417(4) . ? C5 H5 0.9300 . ? C6 C7 1.502(3) . ? C7 N1 1.495(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.349(3) . ? C8 C9 1.362(4) . ? C8 H8 0.9300 . ? C9 C10 1.378(4) . ? C9 H9 0.9300 . ? C10 C11 1.359(4) . ? C10 H10 0.9300 . ? C11 C12 1.369(4) . ? C11 H11 0.9300 . ? C12 N1 1.331(3) . ? C12 H12 0.9300 . ? C13 N2 1.143(3) . ? C13 C15 1.422(3) . ? C14 N3 1.148(3) . ? C14 C15 1.415(3) . ? C15 C16 1.400(3) . ? C16 C17 1.423(3) . ? C16 C21 1.434(3) . ? C17 C18 1.358(3) . ? C17 H17 0.9300 . ? C18 C19 1.421(3) . ? C18 H18 0.9300 . ? C19 C22 1.402(3) . ? C19 C20 1.427(3) . ? C20 C21 1.362(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C24 1.423(3) . ? C22 C23 1.429(4) . ? C23 N4 1.131(4) . ? C24 N5 1.142(3) . ? C25 N6 1.148(3) . ? C25 C27 1.421(3) . ? C26 N7 1.153(3) . ? C26 C27 1.412(3) . ? C27 C28 1.412(3) . ? C28 C29 1.415(3) . ? C28 C30 1.429(3) . ? C29 C30 1.359(3) 2_656 ? C29 H29 0.9300 . ? C30 C29 1.359(3) 2_656 ? C30 H30 0.9300 . ? 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 C2 C1 C6 121.7(2) . . ? C2 C1 Cl1 118.5(2) . . ? C6 C1 Cl1 119.8(2) . . ? C3 C2 C1 119.6(3) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 120.1(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 121.3(3) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 117.3(2) . . ? C1 C6 C7 122.4(2) . . ? C5 C6 C7 120.2(2) . . ? N1 C7 C6 110.51(19) . . ? N1 C7 H7A 109.5 . . ? C6 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? N1 C8 C9 120.5(3) . . ? N1 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C10 119.1(3) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C11 C10 C9 119.9(3) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 119.1(3) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? N1 C12 C11 121.1(2) . . ? N1 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? N2 C13 C15 176.8(3) . . ? N3 C14 C15 177.2(3) . . ? C16 C15 C14 123.6(2) . . ? C16 C15 C13 121.9(2) . . ? C14 C15 C13 114.5(2) . . ? C15 C16 C17 122.2(2) . . ? C15 C16 C21 120.0(2) . . ? C17 C16 C21 117.9(2) . . ? C18 C17 C16 121.5(2) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C17 C18 C19 121.1(2) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C22 C19 C18 122.0(2) . . ? C22 C19 C20 120.5(2) . . ? C18 C19 C20 117.5(2) . . ? C21 C20 C19 121.9(2) . . ? C21 C20 H20 119.0 . . ? C19 C20 H20 119.0 . . ? C20 C21 C16 120.1(2) . . ? C20 C21 H21 120.0 . . ? C16 C21 H21 120.0 . . ? C19 C22 C24 121.9(2) . . ? C19 C22 C23 122.3(2) . . ? C24 C22 C23 115.9(2) . . ? N4 C23 C22 177.2(3) . . ? N5 C24 C22 178.3(3) . . ? N6 C25 C27 178.6(2) . . ? N7 C26 C27 178.4(2) . . ? C28 C27 C26 123.5(2) . . ? C28 C27 C25 121.19(19) . . ? C26 C27 C25 115.27(19) . . ? C27 C28 C29 121.36(19) . . ? C27 C28 C30 121.1(2) . . ? C29 C28 C30 117.47(19) . . ? C30 C29 C28 121.5(2) 2_656 . ? C30 C29 H29 119.2 2_656 . ? C28 C29 H29 119.2 . . ? C29 C30 C28 121.0(2) 2_656 . ? C29 C30 H30 119.5 2_656 . ? C28 C30 H30 119.5 . . ? C12 N1 C8 120.3(2) . . ? C12 N1 C7 120.1(2) . . ? C8 N1 C7 119.6(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.8(4) . . . . ? Cl1 C1 C2 C3 179.84(19) . . . . ? C1 C2 C3 C4 -0.4(4) . . . . ? C2 C3 C4 C5 0.9(4) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? C2 C1 C6 C5 1.5(4) . . . . ? Cl1 C1 C6 C5 -179.17(17) . . . . ? C2 C1 C6 C7 -177.9(2) . . . . ? Cl1 C1 C6 C7 1.5(3) . . . . ? C4 C5 C6 C1 -1.0(4) . . . . ? C4 C5 C6 C7 178.4(2) . . . . ? C1 C6 C7 N1 73.1(3) . . . . ? C5 C6 C7 N1 -106.2(3) . . . . ? N1 C8 C9 C10 -1.1(4) . . . . ? C8 C9 C10 C11 -0.3(4) . . . . ? C9 C10 C11 C12 1.0(4) . . . . ? C10 C11 C12 N1 -0.2(4) . . . . ? N3 C14 C15 C16 174(6) . . . . ? N3 C14 C15 C13 -3(6) . . . . ? N2 C13 C15 C16 -145(5) . . . . ? N2 C13 C15 C14 32(5) . . . . ? C14 C15 C16 C17 178.9(2) . . . . ? C13 C15 C16 C17 -4.3(3) . . . . ? C14 C15 C16 C21 -1.0(3) . . . . ? C13 C15 C16 C21 175.8(2) . . . . ? C15 C16 C17 C18 -179.7(2) . . . . ? C21 C16 C17 C18 0.3(3) . . . . ? C16 C17 C18 C19 -0.2(3) . . . . ? C17 C18 C19 C22 -179.5(2) . . . . ? C17 C18 C19 C20 -0.6(3) . . . . ? C22 C19 C20 C21 -179.7(2) . . . . ? C18 C19 C20 C21 1.3(3) . . . . ? C19 C20 C21 C16 -1.2(4) . . . . ? C15 C16 C21 C20 -179.6(2) . . . . ? C17 C16 C21 C20 0.4(3) . . . . ? C18 C19 C22 C24 176.4(2) . . . . ? C20 C19 C22 C24 -2.5(4) . . . . ? C18 C19 C22 C23 -4.6(4) . . . . ? C20 C19 C22 C23 176.4(2) . . . . ? C19 C22 C23 N4 -145(7) . . . . ? C24 C22 C23 N4 34(7) . . . . ? C19 C22 C24 N5 -163(10) . . . . ? C23 C22 C24 N5 18(10) . . . . ? N7 C26 C27 C28 -164(10) . . . . ? N7 C26 C27 C25 19(11) . . . . ? N6 C25 C27 C28 -179(100) . . . . ? N6 C25 C27 C26 -2(12) . . . . ? C26 C27 C28 C29 -177.7(2) . . . . ? C25 C27 C28 C29 -1.0(3) . . . . ? C26 C27 C28 C30 4.0(3) . . . . ? C25 C27 C28 C30 -179.4(2) . . . . ? C27 C28 C29 C30 -178.9(2) . . . 2_656 ? C30 C28 C29 C30 -0.5(3) . . . 2_656 ? C27 C28 C30 C29 178.9(2) . . . 2_656 ? C29 C28 C30 C29 0.5(3) . . . 2_656 ? C11 C12 N1 C8 -1.2(4) . . . . ? C11 C12 N1 C7 -178.9(2) . . . . ? C9 C8 N1 C12 1.9(4) . . . . ? C9 C8 N1 C7 179.6(2) . . . . ? C6 C7 N1 C12 -126.5(3) . . . . ? C6 C7 N1 C8 55.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.012 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.075 #======================================================== data_TQ2 _database_code_depnum_ccdc_archive 'CCDC 674962' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 Cl N, C12 H4 N4' _chemical_formula_sum 'C25 H17 Cl N5' _chemical_formula_weight 422.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _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 4.1599(15) _cell_length_b 25.278(9) _cell_length_c 19.840(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.912(5) _cell_angle_gamma 90.00 _cell_volume 2086.1(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1573 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 21.08 _exptl_crystal_description needle _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 0.206 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9295 _exptl_absorpt_correction_T_max 0.9877 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Aepex 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 10494 _diffrn_reflns_av_R_equivalents 0.0503 _diffrn_reflns_av_sigmaI/netI 0.0638 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3826 _reflns_number_gt 2251 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, 1998.' _computing_cell_refinement 'SAINT-PLUS, Ver. 6.0, 1997' _computing_data_reduction 'SAINT-PLUS, Ver. 6.0, 1997' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, Ver. 6.10, Bruker AXS Inc., 2000.' _computing_publication_material 'SHELXTL-Bruker AXS Inc., 1998.' _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^)+(0.0416P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3826 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0890 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1097 _refine_ls_wR_factor_gt 0.0974 _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 C1 C 0.3392(6) 0.42181(9) -0.07090(11) 0.0500(6) Uani 1 1 d . . . C2 C 0.4338(6) 0.42226(9) -0.00352(11) 0.0534(7) Uani 1 1 d . . . H2 H 0.3730 0.4498 0.0246 0.064 Uiso 1 1 calc R . . C3 C 0.6192(6) 0.38124(9) 0.02101(11) 0.0499(6) Uani 1 1 d . . . H3 H 0.6852 0.3815 0.0660 0.060 Uiso 1 1 calc R . . C4 C 0.7096(6) 0.33956(9) -0.01972(10) 0.0441(6) Uani 1 1 d . . . C5 C 0.6076(6) 0.34000(10) -0.08712(11) 0.0529(6) Uani 1 1 d . . . H5 H 0.6643 0.3122 -0.1153 0.064 Uiso 1 1 calc R . . C6 C 0.4247(6) 0.38088(10) -0.11244(11) 0.0566(7) Uani 1 1 d . . . H6 H 0.3592 0.3808 -0.1575 0.068 Uiso 1 1 calc R . . C7 C 0.9250(6) 0.29597(9) 0.00689(11) 0.0516(6) Uani 1 1 d . . . H7A H 1.0399 0.2803 -0.0303 0.062 Uiso 1 1 calc R . . H7B H 1.0826 0.3110 0.0380 0.062 Uiso 1 1 calc R . . C8 C 0.6207(6) 0.21251(9) 0.00701(11) 0.0513(6) Uani 1 1 d . . . H8 H 0.6511 0.2106 -0.0393 0.062 Uiso 1 1 calc R . . C9 C 0.4551(6) 0.17339(9) 0.03928(12) 0.0570(7) Uani 1 1 d . . . H9 H 0.3727 0.1448 0.0151 0.068 Uiso 1 1 calc R . . C10 C 0.4111(6) 0.17666(9) 0.10796(12) 0.0567(7) Uani 1 1 d . . . H10 H 0.2986 0.1501 0.1299 0.068 Uiso 1 1 calc R . . C11 C 0.5327(6) 0.21906(9) 0.14460(11) 0.0479(6) Uani 1 1 d . . . C12 C 0.6961(6) 0.25730(8) 0.10968(10) 0.0453(6) Uani 1 1 d . . . H12 H 0.7789 0.2863 0.1329 0.054 Uiso 1 1 calc R . . C13 C 0.4934(7) 0.22400(10) 0.21998(11) 0.0708(8) Uani 1 1 d . . . H13A H 0.5602 0.2586 0.2343 0.106 Uiso 1 1 calc R . . H13B H 0.6232 0.1978 0.2424 0.106 Uiso 1 1 calc R . . H13C H 0.2718 0.2187 0.2310 0.106 Uiso 1 1 calc R . . C14 C 1.1122(6) 0.35695(8) 0.22138(11) 0.0428(6) Uani 1 1 d . . . C15 C 1.0847(6) 0.32661(9) 0.33625(11) 0.0498(6) Uani 1 1 d . . . C16 C 0.9983(6) 0.36554(8) 0.28763(9) 0.0417(6) Uani 1 1 d . . . C17 C 0.8027(5) 0.40974(8) 0.30349(9) 0.0413(6) Uani 1 1 d . . . C18 C 0.6995(6) 0.41963(8) 0.37029(10) 0.0459(6) Uani 1 1 d . . . H18 H 0.7599 0.3963 0.4045 0.055 Uiso 1 1 calc R . . C19 C 0.5153(6) 0.46210(8) 0.38540(10) 0.0493(6) Uani 1 1 d . . . H19 H 0.4545 0.4675 0.4298 0.059 Uiso 1 1 calc R . . C20 C 0.4133(6) 0.49844(8) 0.33502(10) 0.0431(6) Uani 1 1 d . . . C21 C 0.5177(6) 0.48891(8) 0.26838(10) 0.0474(6) Uani 1 1 d . . . H21 H 0.4582 0.5123 0.2343 0.057 Uiso 1 1 calc R . . C22 C 0.7031(6) 0.44628(8) 0.25322(10) 0.0462(6) Uani 1 1 d . . . H22 H 0.7655 0.4410 0.2089 0.055 Uiso 1 1 calc R . . C23 C 0.2198(6) 0.54304(8) 0.34990(10) 0.0457(6) Uani 1 1 d . . . C24 C 0.1092(6) 0.55493(9) 0.41603(12) 0.0497(6) Uani 1 1 d . . . C25 C 0.1216(6) 0.58022(9) 0.30003(11) 0.0477(6) Uani 1 1 d . . . Cl1 Cl 0.11744(18) 0.47479(3) -0.10296(3) 0.0714(2) Uani 1 1 d . . . N1 N 0.7395(4) 0.25369(7) 0.04227(8) 0.0426(5) Uani 1 1 d . . . N2 N 1.2023(5) 0.34973(8) 0.16765(9) 0.0600(6) Uani 1 1 d . . . N3 N 1.1478(6) 0.29459(9) 0.37559(10) 0.0709(7) Uani 1 1 d . . . N4 N 0.0168(6) 0.56699(8) 0.46782(10) 0.0680(7) Uani 1 1 d . . . N5 N 0.0435(6) 0.61151(8) 0.26123(10) 0.0660(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0494(17) 0.0501(15) 0.0505(14) 0.0132(12) 0.0063(12) -0.0105(12) C2 0.0614(18) 0.0501(15) 0.0492(14) -0.0006(12) 0.0110(13) -0.0084(13) C3 0.0536(17) 0.0593(16) 0.0370(12) 0.0005(12) 0.0060(11) -0.0110(13) C4 0.0421(15) 0.0494(14) 0.0411(12) 0.0044(11) 0.0099(11) -0.0090(12) C5 0.0577(18) 0.0573(16) 0.0440(13) -0.0038(12) 0.0081(12) -0.0058(14) C6 0.065(2) 0.0655(18) 0.0395(13) 0.0015(12) 0.0018(13) -0.0090(15) C7 0.0431(16) 0.0604(16) 0.0517(13) 0.0043(12) 0.0113(12) -0.0103(13) C8 0.0520(17) 0.0534(15) 0.0486(13) -0.0054(12) 0.0019(12) -0.0024(13) C9 0.0587(19) 0.0470(15) 0.0653(16) -0.0044(12) 0.0033(14) -0.0053(13) C10 0.0573(18) 0.0473(15) 0.0655(16) 0.0106(13) 0.0055(13) -0.0042(13) C11 0.0470(16) 0.0445(14) 0.0525(13) 0.0059(12) 0.0068(12) 0.0031(12) C12 0.0456(16) 0.0438(14) 0.0466(13) -0.0044(11) 0.0015(11) 0.0020(12) C13 0.087(2) 0.0722(18) 0.0537(15) 0.0096(13) 0.0177(15) 0.0064(16) C14 0.0478(17) 0.0383(13) 0.0424(13) -0.0044(10) -0.0001(12) 0.0000(11) C15 0.0563(18) 0.0479(15) 0.0455(13) -0.0036(12) 0.0073(12) 0.0053(13) C16 0.0513(16) 0.0417(13) 0.0322(11) 0.0020(10) 0.0027(10) 0.0024(12) C17 0.0532(16) 0.0382(13) 0.0324(11) -0.0011(10) 0.0000(11) 0.0011(11) C18 0.0645(18) 0.0415(14) 0.0317(11) 0.0034(10) 0.0031(11) 0.0045(12) C19 0.0719(19) 0.0465(14) 0.0297(11) -0.0008(10) 0.0054(11) 0.0050(13) C20 0.0546(17) 0.0394(13) 0.0355(12) -0.0033(10) 0.0008(11) 0.0025(11) C21 0.0666(18) 0.0429(14) 0.0326(11) 0.0041(10) 0.0028(11) 0.0036(13) C22 0.0653(18) 0.0441(13) 0.0293(11) 0.0007(10) 0.0060(11) 0.0044(12) C23 0.0563(17) 0.0436(14) 0.0370(12) -0.0032(10) 0.0023(11) 0.0011(12) C24 0.0594(18) 0.0451(14) 0.0446(14) -0.0015(11) 0.0009(12) 0.0074(12) C25 0.0559(17) 0.0444(14) 0.0430(13) -0.0076(11) 0.0028(12) 0.0051(13) Cl1 0.0742(5) 0.0666(5) 0.0735(4) 0.0205(3) 0.0047(4) 0.0016(4) N1 0.0367(12) 0.0438(11) 0.0474(11) 0.0021(9) 0.0046(9) 0.0002(9) N2 0.0713(17) 0.0640(14) 0.0449(12) -0.0090(10) 0.0097(11) 0.0034(12) N3 0.0884(19) 0.0677(15) 0.0568(13) 0.0160(12) 0.0084(12) 0.0215(13) N4 0.0884(19) 0.0687(15) 0.0471(12) -0.0033(11) 0.0100(12) 0.0198(13) N5 0.0849(18) 0.0563(14) 0.0565(13) 0.0047(11) -0.0043(12) 0.0164(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.373(3) . ? C1 C2 1.388(3) . ? C1 Cl1 1.741(2) . ? C2 C3 1.377(3) . ? C2 H2 0.9300 . ? C3 C4 1.384(3) . ? C3 H3 0.9300 . ? C4 C5 1.397(3) . ? C4 C7 1.510(3) . ? C5 C6 1.373(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.499(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.344(3) . ? C8 C9 1.370(3) . ? C8 H8 0.9300 . ? C9 C10 1.380(3) . ? C9 H9 0.9300 . ? C10 C11 1.386(3) . ? C10 H10 0.9300 . ? C11 C12 1.375(3) . ? C11 C13 1.512(3) . ? C12 N1 1.355(3) . ? C12 H12 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N2 1.150(3) . ? C14 C16 1.421(3) . ? C15 N3 1.152(3) . ? C15 C16 1.420(3) . ? C16 C17 1.420(3) . ? C17 C22 1.417(3) . ? C17 C18 1.422(3) . ? C18 C19 1.356(3) . ? C18 H18 0.9300 . ? C19 C20 1.417(3) . ? C19 H19 0.9300 . ? C20 C21 1.419(3) . ? C20 C23 1.419(3) . ? C21 C22 1.361(3) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C25 1.420(3) . ? C23 C24 1.429(3) . ? C24 N4 1.144(3) . ? C25 N5 1.147(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 120.8(2) . . ? C6 C1 Cl1 120.07(18) . . ? C2 C1 Cl1 119.10(19) . . ? C3 C2 C1 118.9(2) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 121.5(2) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C3 C4 C5 118.2(2) . . ? C3 C4 C7 121.11(19) . . ? C5 C4 C7 120.7(2) . . ? C6 C5 C4 120.9(2) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C1 C6 C5 119.6(2) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? N1 C7 C4 112.13(18) . . ? N1 C7 H7A 109.2 . . ? C4 C7 H7A 109.2 . . ? N1 C7 H7B 109.2 . . ? C4 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? N1 C8 C9 119.9(2) . . ? N1 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C8 C9 C10 119.6(2) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C9 C10 C11 120.7(2) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 117.3(2) . . ? C12 C11 C13 120.2(2) . . ? C10 C11 C13 122.6(2) . . ? N1 C12 C11 121.6(2) . . ? N1 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 C16 179.4(3) . . ? N3 C15 C16 178.5(3) . . ? C15 C16 C17 122.30(19) . . ? C15 C16 C14 115.97(19) . . ? C17 C16 C14 121.72(18) . . ? C22 C17 C16 121.28(18) . . ? C22 C17 C18 116.89(19) . . ? C16 C17 C18 121.83(18) . . ? C19 C18 C17 121.71(19) . . ? C19 C18 H18 119.1 . . ? C17 C18 H18 119.1 . . ? C18 C19 C20 121.4(2) . . ? C18 C19 H19 119.3 . . ? C20 C19 H19 119.3 . . ? C19 C20 C21 117.0(2) . . ? C19 C20 C23 122.17(19) . . ? C21 C20 C23 120.79(19) . . ? C22 C21 C20 121.54(19) . . ? C22 C21 H21 119.2 . . ? C20 C21 H21 119.2 . . ? C21 C22 C17 121.40(19) . . ? C21 C22 H22 119.3 . . ? C17 C22 H22 119.3 . . ? C20 C23 C25 122.60(19) . . ? C20 C23 C24 123.38(19) . . ? C25 C23 C24 114.0(2) . . ? N4 C24 C23 176.5(2) . . ? N5 C25 C23 177.8(2) . . ? C8 N1 C12 120.82(19) . . ? C8 N1 C7 119.74(18) . . ? C12 N1 C7 119.44(18) . . ? 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 C1 C2 C3 0.9(4) . . . . ? Cl1 C1 C2 C3 -177.63(18) . . . . ? C1 C2 C3 C4 -0.7(4) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C2 C3 C4 C7 177.3(2) . . . . ? C3 C4 C5 C6 0.5(3) . . . . ? C7 C4 C5 C6 -176.8(2) . . . . ? C2 C1 C6 C5 -0.3(4) . . . . ? Cl1 C1 C6 C5 178.14(18) . . . . ? C4 C5 C6 C1 -0.4(4) . . . . ? C3 C4 C7 N1 84.8(3) . . . . ? C5 C4 C7 N1 -98.0(2) . . . . ? N1 C8 C9 C10 0.1(4) . . . . ? C8 C9 C10 C11 0.0(4) . . . . ? C9 C10 C11 C12 0.2(4) . . . . ? C9 C10 C11 C13 -179.3(2) . . . . ? C10 C11 C12 N1 -0.5(3) . . . . ? C13 C11 C12 N1 179.1(2) . . . . ? N3 C15 C16 C17 74(9) . . . . ? N3 C15 C16 C14 -104(9) . . . . ? N2 C14 C16 C15 84(30) . . . . ? N2 C14 C16 C17 -94(30) . . . . ? C15 C16 C17 C22 -176.0(2) . . . . ? C14 C16 C17 C22 2.3(3) . . . . ? C15 C16 C17 C18 4.4(4) . . . . ? C14 C16 C17 C18 -177.3(2) . . . . ? C22 C17 C18 C19 -0.2(3) . . . . ? C16 C17 C18 C19 179.4(2) . . . . ? C17 C18 C19 C20 0.8(4) . . . . ? C18 C19 C20 C21 -1.2(3) . . . . ? C18 C19 C20 C23 179.9(2) . . . . ? C19 C20 C21 C22 1.1(4) . . . . ? C23 C20 C21 C22 -179.9(2) . . . . ? C20 C21 C22 C17 -0.6(4) . . . . ? C16 C17 C22 C21 -179.5(2) . . . . ? C18 C17 C22 C21 0.2(3) . . . . ? C19 C20 C23 C25 178.8(2) . . . . ? C21 C20 C23 C25 -0.2(4) . . . . ? C19 C20 C23 C24 -0.6(4) . . . . ? C21 C20 C23 C24 -179.6(2) . . . . ? C20 C23 C24 N4 165(5) . . . . ? C25 C23 C24 N4 -15(5) . . . . ? C20 C23 C25 N5 -143(7) . . . . ? C24 C23 C25 N5 37(7) . . . . ? C9 C8 N1 C12 -0.3(3) . . . . ? C9 C8 N1 C7 179.1(2) . . . . ? C11 C12 N1 C8 0.6(3) . . . . ? C11 C12 N1 C7 -178.8(2) . . . . ? C4 C7 N1 C8 88.9(2) . . . . ? C4 C7 N1 C12 -91.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.202 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.041 # Attachment 'CEC0801-revised.cif' data_TQ3 _database_code_depnum_ccdc_archive 'CCDC 674963' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H13 N2, C12 H4 N4' _chemical_formula_sum 'C24 H17 N6' _chemical_formula_weight 389.44 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 'P 21/c' _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 11.702(4) _cell_length_b 8.678(3) _cell_length_c 22.271(7) _cell_angle_alpha 90.00 _cell_angle_beta 113.082(15) _cell_angle_gamma 90.00 _cell_volume 2080.6(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4476 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 27.68 _exptl_crystal_description block _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 812 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9816 _exptl_absorpt_correction_T_max 0.9923 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Aepex 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 9945 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_sigmaI/netI 0.1190 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3660 _reflns_number_gt 2814 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, 1998' _computing_cell_refinement 'SAINT-PLUS, Ver. 6.0, 1997' _computing_data_reduction 'SAINT-PLUS, Ver. 6.0, 1997' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, Ver. 6.10, Bruker AXS Inc., 2000' _computing_publication_material 'SHELXTL-Bruker AXS Inc., 1998' _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^)+(0.0803P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3660 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0703 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1705 _refine_ls_wR_factor_gt 0.1597 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.18011(11) 1.12991(15) 0.74730(6) 0.1078(9) Uani 1 1 d . . . H1 H 0.2430 1.1863 0.7786 0.129 Uiso 1 1 calc R . . C2 C 0.05749(11) 1.18297(15) 0.72425(6) 0.169(2) Uani 1 1 d R . . H2 H 0.0385 1.2757 0.7392 0.203 Uiso 1 1 d R . . C3 C -0.03352(11) 1.09681(15) 0.67970(6) 0.191(2) Uani 1 1 d R . . H3 H -0.1156 1.1295 0.6656 0.229 Uiso 1 1 d R . . C4 C -0.00843(11) 0.96999(15) 0.65642(6) 0.1603(18) Uani 1 1 d R . . H4 H -0.0721 0.9153 0.6248 0.192 Uiso 1 1 d R . . C5 C 0.11208(11) 0.91558(15) 0.67813(6) 0.1081(9) Uani 1 1 d R . . H5 H 0.1290 0.8239 0.6616 0.130 Uiso 1 1 d R . . C6 C 0.20727(11) 0.99730(15) 0.72431(6) 0.0644(5) Uani 1 1 d R . . C7 C 0.33818(16) 0.9378(2) 0.74784(10) 0.0660(5) Uani 1 1 d . . . H7A H 0.3550 0.9028 0.7107 0.079 Uiso 1 1 calc R . . H7B H 0.3954 1.0210 0.7687 0.079 Uiso 1 1 calc R . . C8 C 0.38156(16) 0.6646(2) 0.77971(8) 0.0560(4) Uani 1 1 d . . . H8 H 0.3860 0.6470 0.7395 0.067 Uiso 1 1 calc R . . C9 C 0.39724(16) 0.5452(2) 0.82065(8) 0.0558(4) Uani 1 1 d . . . H9 H 0.4134 0.4476 0.8087 0.067 Uiso 1 1 calc R . . C10 C 0.38932(13) 0.56699(19) 0.88140(7) 0.0496(4) Uani 1 1 d . . . C11 C 0.37119(16) 0.7203(2) 0.89698(8) 0.0580(5) Uani 1 1 d . . . H11 H 0.3687 0.7423 0.9373 0.070 Uiso 1 1 calc R . . C12 C 0.35744(17) 0.8352(2) 0.85387(8) 0.0581(5) Uani 1 1 d . . . H12 H 0.3461 0.9355 0.8653 0.070 Uiso 1 1 calc R . . C13 C 0.33573(14) 1.04385(19) 0.99107(8) 0.0483(4) Uani 1 1 d . . . C14 C 0.37712(14) 0.87013(18) 1.08221(8) 0.0506(4) Uani 1 1 d . . . C15 C 0.29072(14) 0.93665(17) 1.02383(7) 0.0456(4) Uani 1 1 d . . . C16 C 0.16381(13) 0.88763(17) 0.99686(7) 0.0432(4) Uani 1 1 d . . . C17 C 0.12121(13) 0.76769(18) 1.02515(7) 0.0477(4) Uani 1 1 d . . . H17 H 0.1771 0.7181 1.0620 0.057 Uiso 1 1 calc R . . C18 C 0.00000(14) 0.72219(17) 0.99996(8) 0.0488(4) Uani 1 1 d . . . H18 H -0.0253 0.6428 1.0200 0.059 Uiso 1 1 calc R . . C19 C -0.08839(13) 0.79410(17) 0.94352(7) 0.0436(4) Uani 1 1 d . . . C20 C -0.04504(14) 0.91169(19) 0.91419(7) 0.0505(4) Uani 1 1 d . . . H20 H -0.1004 0.9593 0.8766 0.061 Uiso 1 1 calc R . . C21 C 0.07663(14) 0.95743(18) 0.93967(7) 0.0495(4) Uani 1 1 d . . . H21 H 0.1025 1.0354 0.9192 0.059 Uiso 1 1 calc R . . C22 C -0.21540(14) 0.74820(19) 0.91734(7) 0.0475(4) Uani 1 1 d . . . C23 C -0.25995(14) 0.63389(19) 0.94732(8) 0.0505(4) Uani 1 1 d . . . C24 C -0.30110(15) 0.80849(19) 0.85767(8) 0.0529(4) Uani 1 1 d . . . N1 N 0.35970(12) 0.80861(16) 0.79487(7) 0.0517(4) Uani 1 1 d . . . N2 N 0.39642(14) 0.45085(17) 0.92135(8) 0.0678(5) Uani 1 1 d . . . H2A H 0.4062 0.3583 0.9104 0.081 Uiso 1 1 calc R . . H2B H 0.3912 0.4680 0.9582 0.081 Uiso 1 1 calc R . . N3 N 0.36892(15) 1.12874(19) 0.96161(8) 0.0671(5) Uani 1 1 d . . . N4 N 0.44544(14) 0.81610(18) 1.13006(8) 0.0689(5) Uani 1 1 d . . . N5 N -0.29552(15) 0.54040(18) 0.97272(9) 0.0707(5) Uani 1 1 d . . . N6 N -0.36923(15) 0.8566(2) 0.80864(8) 0.0707(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.112(2) 0.0844(15) 0.141(2) 0.0215(17) 0.0638(19) 0.0260(14) C2 0.178(4) 0.150(3) 0.236(5) 0.078(3) 0.142(4) 0.090(3) C3 0.098(3) 0.289(6) 0.206(5) 0.136(5) 0.082(3) 0.080(3) C4 0.0618(16) 0.301(6) 0.0941(19) 0.031(3) 0.0049(15) 0.004(2) C5 0.0640(14) 0.185(3) 0.0653(12) -0.0020(17) 0.0145(11) -0.0064(16) C6 0.0535(10) 0.0818(12) 0.0593(10) 0.0219(10) 0.0236(8) 0.0076(9) C7 0.0534(10) 0.0763(12) 0.0687(11) 0.0180(10) 0.0245(9) -0.0010(9) C8 0.0530(9) 0.0697(11) 0.0479(9) -0.0055(8) 0.0227(8) 0.0014(8) C9 0.0567(10) 0.0565(10) 0.0551(9) -0.0070(8) 0.0232(8) 0.0025(8) C10 0.0391(8) 0.0602(10) 0.0478(9) 0.0002(8) 0.0152(7) -0.0041(7) C11 0.0646(11) 0.0678(11) 0.0451(9) -0.0052(8) 0.0253(8) 0.0044(8) C12 0.0618(10) 0.0568(10) 0.0559(10) -0.0078(9) 0.0234(8) 0.0025(8) C13 0.0432(8) 0.0517(9) 0.0545(9) -0.0060(8) 0.0240(7) 0.0021(7) C14 0.0418(8) 0.0594(10) 0.0538(9) -0.0044(8) 0.0222(8) 0.0009(7) C15 0.0395(7) 0.0520(9) 0.0471(8) -0.0022(7) 0.0190(7) 0.0032(7) C16 0.0402(8) 0.0473(8) 0.0442(8) -0.0029(7) 0.0189(7) 0.0046(6) C17 0.0408(8) 0.0527(9) 0.0471(8) 0.0054(7) 0.0145(7) 0.0066(7) C18 0.0483(9) 0.0478(8) 0.0516(8) 0.0039(7) 0.0211(7) 0.0005(7) C19 0.0408(8) 0.0478(8) 0.0422(8) -0.0056(7) 0.0164(7) 0.0020(6) C20 0.0444(8) 0.0594(9) 0.0434(8) 0.0059(8) 0.0127(7) 0.0039(7) C21 0.0483(9) 0.0539(9) 0.0477(8) 0.0076(7) 0.0204(7) 0.0010(7) C22 0.0417(8) 0.0535(9) 0.0465(8) -0.0031(7) 0.0163(7) 0.0005(7) C23 0.0413(8) 0.0554(9) 0.0557(9) -0.0032(8) 0.0199(7) 0.0017(7) C24 0.0413(8) 0.0671(10) 0.0508(9) -0.0041(8) 0.0187(7) -0.0027(7) N1 0.0456(7) 0.0596(8) 0.0505(7) 0.0030(7) 0.0196(6) -0.0003(6) N2 0.0709(10) 0.0687(10) 0.0659(9) 0.0095(8) 0.0293(8) -0.0010(7) N3 0.0669(10) 0.0681(10) 0.0792(10) 0.0026(9) 0.0426(9) -0.0012(7) N4 0.0537(9) 0.0805(10) 0.0606(9) 0.0058(8) 0.0097(8) 0.0067(7) N5 0.0598(9) 0.0706(10) 0.0871(11) 0.0087(9) 0.0347(8) -0.0006(8) N6 0.0501(8) 0.0990(12) 0.0559(9) 0.0114(9) 0.0132(7) 0.0012(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.3473 . ? C1 C2 1.3989 . ? C1 H1 0.9300 . ? C2 C3 1.3598 . ? C2 H2 0.9300 . ? C3 C4 1.2983 . ? C3 H3 0.9300 . ? C4 C5 1.3824 . ? C4 H4 0.9300 . ? C5 C6 1.3795 . ? C5 H5 0.9300 . ? C6 C7 1.503(2) . ? C7 N1 1.487(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.344(2) . ? C8 N1 1.345(2) . ? C8 H8 0.9300 . ? C9 C10 1.405(3) . ? C9 H9 0.9300 . ? C10 N2 1.325(2) . ? C10 C11 1.412(2) . ? C11 C12 1.349(2) . ? C11 H11 0.9300 . ? C12 N1 1.345(2) . ? C12 H12 0.9300 . ? C13 N3 1.151(2) . ? C13 C15 1.406(2) . ? C14 N4 1.1519(19) . ? C14 C15 1.420(2) . ? C15 C16 1.431(2) . ? C16 C17 1.405(2) . ? C16 C21 1.418(2) . ? C17 C18 1.363(2) . ? C17 H17 0.9300 . ? C18 C19 1.421(2) . ? C18 H18 0.9300 . ? C19 C20 1.409(2) . ? C19 C22 1.424(2) . ? C20 C21 1.369(2) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.405(2) . ? C22 C24 1.414(2) . ? C23 N5 1.156(2) . ? C24 N6 1.149(2) . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? 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 C1 C2 120.2 . . ? C6 C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C3 C2 C1 118.9 . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C4 C3 C2 121.5 . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 120.6 . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 120.0 . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C1 C6 C5 118.7 . . ? C1 C6 C7 121.40(10) . . ? C5 C6 C7 119.87(10) . . ? N1 C7 C6 111.88(14) . . ? N1 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? N1 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C9 C8 N1 122.31(15) . . ? C9 C8 H8 118.8 . . ? N1 C8 H8 118.8 . . ? C8 C9 C10 120.45(16) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? N2 C10 C9 122.28(16) . . ? N2 C10 C11 121.85(15) . . ? C9 C10 C11 115.87(16) . . ? C12 C11 C10 120.61(16) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? N1 C12 C11 121.71(16) . . ? N1 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? N3 C13 C15 176.88(16) . . ? N4 C14 C15 178.65(18) . . ? C13 C15 C14 117.85(14) . . ? C13 C15 C16 121.14(13) . . ? C14 C15 C16 120.86(14) . . ? C17 C16 C21 117.53(13) . . ? C17 C16 C15 121.61(13) . . ? C21 C16 C15 120.85(14) . . ? C18 C17 C16 121.65(14) . . ? C18 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? C17 C18 C19 121.05(15) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C20 C19 C18 117.30(14) . . ? C20 C19 C22 121.36(13) . . ? C18 C19 C22 121.34(15) . . ? C21 C20 C19 121.53(13) . . ? C21 C20 H20 119.2 . . ? C19 C20 H20 119.2 . . ? C20 C21 C16 120.91(15) . . ? C20 C21 H21 119.5 . . ? C16 C21 H21 119.5 . . ? C23 C22 C24 116.69(14) . . ? C23 C22 C19 121.67(14) . . ? C24 C22 C19 121.53(15) . . ? N5 C23 C22 179.16(18) . . ? N6 C24 C22 178.71(19) . . ? C12 N1 C8 118.93(15) . . ? C12 N1 C7 119.74(15) . . ? C8 N1 C7 121.34(15) . . ? C10 N2 H2A 120.0 . . ? C10 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? 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 C1 C2 C3 1.6 . . . . ? C1 C2 C3 C4 -2.6 . . . . ? C2 C3 C4 C5 2.3 . . . . ? C3 C4 C5 C6 -0.9 . . . . ? C2 C1 C6 C5 -0.3 . . . . ? C2 C1 C6 C7 179.65(10) . . . . ? C4 C5 C6 C1 -0.1 . . . . ? C4 C5 C6 C7 179.98(10) . . . . ? C1 C6 C7 N1 103.30(13) . . . . ? C5 C6 C7 N1 -76.79(15) . . . . ? N1 C8 C9 C10 1.0(3) . . . . ? C8 C9 C10 N2 175.66(15) . . . . ? C8 C9 C10 C11 -3.3(2) . . . . ? N2 C10 C11 C12 -176.31(16) . . . . ? C9 C10 C11 C12 2.7(2) . . . . ? C10 C11 C12 N1 0.4(3) . . . . ? N3 C13 C15 C14 142(3) . . . . ? N3 C13 C15 C16 -34(3) . . . . ? N4 C14 C15 C13 145(7) . . . . ? N4 C14 C15 C16 -39(8) . . . . ? C13 C15 C16 C17 172.44(14) . . . . ? C14 C15 C16 C17 -3.0(2) . . . . ? C13 C15 C16 C21 -6.6(2) . . . . ? C14 C15 C16 C21 178.02(14) . . . . ? C21 C16 C17 C18 -1.8(2) . . . . ? C15 C16 C17 C18 179.17(15) . . . . ? C16 C17 C18 C19 0.4(2) . . . . ? C17 C18 C19 C20 1.2(2) . . . . ? C17 C18 C19 C22 -179.35(14) . . . . ? C18 C19 C20 C21 -1.4(2) . . . . ? C22 C19 C20 C21 179.18(16) . . . . ? C19 C20 C21 C16 0.0(3) . . . . ? C17 C16 C21 C20 1.6(2) . . . . ? C15 C16 C21 C20 -179.35(15) . . . . ? C20 C19 C22 C23 -178.27(14) . . . . ? C18 C19 C22 C23 2.3(2) . . . . ? C20 C19 C22 C24 5.8(2) . . . . ? C18 C19 C22 C24 -173.63(15) . . . . ? C24 C22 C23 N5 -153(13) . . . . ? C19 C22 C23 N5 31(13) . . . . ? C23 C22 C24 N6 -122(9) . . . . ? C19 C22 C24 N6 54(9) . . . . ? C11 C12 N1 C8 -2.9(3) . . . . ? C11 C12 N1 C7 177.11(16) . . . . ? C9 C8 N1 C12 2.2(3) . . . . ? C9 C8 N1 C7 -177.78(15) . . . . ? C6 C7 N1 C12 -67.3(2) . . . . ? C6 C7 N1 C8 112.72(18) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.221 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.057 #=================================================== data_TQ4 _database_code_depnum_ccdc_archive 'CCDC 674964' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C16 H13 Br N), 2(C12 H4 N4), C2 H3 N' _chemical_formula_sum 'C58 H37 Br2 N11' _chemical_formula_weight 1047.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 35.313(18) _cell_length_b 7.272(4) _cell_length_c 22.982(11) _cell_angle_alpha 90.00 _cell_angle_beta 124.01(3) _cell_angle_gamma 90.00 _cell_volume 4892(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 999 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 17.95 _exptl_crystal_description platelet _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2128 _exptl_absorpt_coefficient_mu 1.709 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7262 _exptl_absorpt_correction_T_max 0.9348 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Aepex 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 11529 _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_sigmaI/netI 0.0995 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4256 _reflns_number_gt 2525 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, 1998' _computing_cell_refinement 'SAINT-PLUS, Ver. 6.0, 1997' _computing_data_reduction 'SAINT-PLUS, Ver. 6.0, 1997' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, Ver. 6.10, Bruker AXS Inc., 2000' _computing_publication_material 'SHELXTL-Bruker AXS Inc., 1998' _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^)+(0.0107P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4256 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1968 _refine_ls_R_factor_gt 0.0804 _refine_ls_wR_factor_ref 0.1373 _refine_ls_wR_factor_gt 0.1234 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.21837(3) 0.83030(12) 0.21516(5) 0.1003(4) Uani 1 1 d . . . C1 C 0.1841(2) 0.6091(9) 0.1923(4) 0.058(2) Uani 1 1 d . . . C2 C 0.1690(2) 0.5533(11) 0.2325(4) 0.067(2) Uani 1 1 d . . . H2 H 0.1757 0.6212 0.2715 0.080 Uiso 1 1 calc R . . C3 C 0.1436(2) 0.3944(11) 0.2144(4) 0.064(2) Uani 1 1 d . . . H3 H 0.1326 0.3573 0.2411 0.077 Uiso 1 1 calc R . . C4 C 0.1340(2) 0.2896(9) 0.1583(3) 0.0379(17) Uani 1 1 d . . . C5 C 0.1498(2) 0.3492(9) 0.1182(3) 0.0463(19) Uani 1 1 d . . . H5 H 0.1436 0.2797 0.0799 0.056 Uiso 1 1 calc R . . C6 C 0.1745(2) 0.5098(10) 0.1343(4) 0.061(2) Uani 1 1 d . . . H6 H 0.1844 0.5503 0.1067 0.073 Uiso 1 1 calc R . . C7 C 0.1051(2) 0.1194(8) 0.1387(3) 0.0438(18) Uani 1 1 d . . . H7A H 0.1172 0.0413 0.1796 0.053 Uiso 1 1 calc R . . H7B H 0.1062 0.0512 0.1034 0.053 Uiso 1 1 calc R . . C8 C 0.0435(3) 0.1769(9) 0.1555(4) 0.054(2) Uani 1 1 d . . . H8 H 0.0645 0.1390 0.2014 0.065 Uiso 1 1 calc R . . C9 C 0.0029(3) 0.2364(9) 0.1391(4) 0.052(2) Uani 1 1 d . . . H9 H -0.0040 0.2440 0.1726 0.063 Uiso 1 1 calc R . . C10 C -0.0274(3) 0.2847(9) 0.0720(5) 0.057(2) Uani 1 1 d . . . H10 H -0.0560 0.3267 0.0590 0.068 Uiso 1 1 calc R . . C11 C -0.0177(2) 0.2742(8) 0.0203(4) 0.0404(17) Uani 1 1 d . . . C12 C -0.0498(2) 0.3148(8) -0.0514(4) 0.056(2) Uani 1 1 d . . . H12 H -0.0789 0.3554 -0.0663 0.068 Uiso 1 1 calc R . . C13 C -0.0383(3) 0.2948(9) -0.0991(4) 0.056(2) Uani 1 1 d . . . H13 H -0.0599 0.3211 -0.1462 0.067 Uiso 1 1 calc R . . C14 C 0.0042(2) 0.2368(8) -0.0787(4) 0.0485(19) Uani 1 1 d . . . H14 H 0.0113 0.2235 -0.1119 0.058 Uiso 1 1 calc R . . C15 C 0.0365(2) 0.1983(7) -0.0098(4) 0.0403(17) Uani 1 1 d . . . H15 H 0.0658 0.1625 0.0045 0.048 Uiso 1 1 calc R . . C16 C 0.0247(2) 0.2136(7) 0.0398(3) 0.0353(17) Uani 1 1 d . . . C17 C 0.1333(2) 0.8246(10) 0.3341(4) 0.049(2) Uani 1 1 d . . . C18 C 0.1245(2) 0.6953(10) 0.4223(4) 0.051(2) Uani 1 1 d . . . C19 C 0.1529(2) 0.7607(9) 0.4029(3) 0.0423(18) Uani 1 1 d . . . C20 C 0.2014(2) 0.7562(8) 0.4514(3) 0.0404(17) Uani 1 1 d . . . C21 C 0.2321(2) 0.8182(8) 0.4332(3) 0.0441(18) Uani 1 1 d . . . H21 H 0.2201 0.8650 0.3884 0.053 Uiso 1 1 calc R . . C22 C 0.2221(2) 0.6897(8) 0.5208(3) 0.0414(18) Uani 1 1 d . . . H22 H 0.2035 0.6501 0.5352 0.050 Uiso 1 1 calc R . . C23 C 0.1223(3) 0.2556(9) 0.3749(4) 0.051(2) Uani 1 1 d . . . C24 C 0.1410(2) 0.1300(10) 0.4845(4) 0.046(2) Uani 1 1 d . . . C25 C 0.1554(2) 0.2027(9) 0.4428(3) 0.0405(17) Uani 1 1 d . . . C26 C 0.2025(2) 0.2275(8) 0.4720(4) 0.0399(17) Uani 1 1 d . . . C27 C 0.2185(2) 0.2988(9) 0.4322(3) 0.0434(18) Uani 1 1 d . . . H27 H 0.1971 0.3326 0.3859 0.052 Uiso 1 1 calc R . . C28 C 0.2360(2) 0.1794(8) 0.5417(3) 0.0436(17) Uani 1 1 d . . . H28 H 0.2274 0.1324 0.5703 0.052 Uiso 1 1 calc R . . C29 C 0.0000 0.5967(16) 0.2500 0.098(5) Uani 1 2 d S . . C30 C 0.0000 0.7902(19) 0.2500 0.075(4) Uani 1 2 d S . . N1 N 0.05618(17) 0.1680(6) 0.1105(3) 0.0401(14) Uani 1 1 d . . . N2 N 0.0000 0.9492(16) 0.2500 0.126(5) Uani 1 2 d S . . N3 N 0.1177(2) 0.8700(9) 0.2774(3) 0.078(2) Uani 1 1 d . . . N4 N 0.1007(2) 0.6379(9) 0.4364(3) 0.074(2) Uani 1 1 d . . . N5 N 0.0944(2) 0.3001(8) 0.3180(3) 0.0668(19) Uani 1 1 d . . . N6 N 0.12925(19) 0.0773(8) 0.5187(3) 0.0625(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0806(7) 0.0709(6) 0.1233(9) -0.0289(6) 0.0411(6) -0.0345(6) C1 0.038(5) 0.038(5) 0.073(6) -0.015(4) 0.016(5) -0.004(4) C2 0.055(6) 0.085(7) 0.070(6) -0.033(5) 0.041(5) -0.019(5) C3 0.055(6) 0.087(7) 0.055(5) -0.012(5) 0.034(5) -0.011(5) C4 0.029(4) 0.044(5) 0.037(4) 0.001(4) 0.017(4) 0.002(3) C5 0.037(4) 0.049(5) 0.053(5) -0.014(4) 0.026(4) 0.000(4) C6 0.046(5) 0.065(6) 0.057(6) 0.003(5) 0.020(5) -0.008(4) C7 0.033(4) 0.039(4) 0.048(4) 0.006(3) 0.016(4) 0.006(3) C8 0.076(6) 0.043(5) 0.052(5) -0.010(4) 0.040(5) -0.015(4) C9 0.060(6) 0.047(5) 0.061(6) -0.008(4) 0.041(5) -0.001(4) C10 0.057(6) 0.039(5) 0.101(7) -0.021(5) 0.061(6) -0.019(4) C11 0.025(4) 0.026(4) 0.060(5) -0.006(4) 0.017(4) -0.011(3) C12 0.040(5) 0.035(4) 0.076(6) -0.002(4) 0.022(5) -0.003(4) C13 0.053(6) 0.044(5) 0.055(5) -0.007(4) 0.021(5) -0.010(4) C14 0.040(5) 0.036(4) 0.053(5) -0.006(4) 0.015(4) -0.009(4) C15 0.036(4) 0.031(4) 0.056(5) -0.004(4) 0.027(4) -0.006(3) C16 0.043(5) 0.018(4) 0.045(5) -0.006(3) 0.024(4) -0.007(3) C17 0.040(5) 0.062(5) 0.036(5) -0.009(4) 0.016(4) 0.006(4) C18 0.036(5) 0.065(6) 0.051(5) -0.015(4) 0.023(4) -0.007(4) C19 0.043(5) 0.047(5) 0.041(5) -0.002(4) 0.027(4) 0.002(4) C20 0.041(5) 0.043(4) 0.034(4) 0.004(3) 0.019(4) 0.004(4) C21 0.052(5) 0.041(4) 0.037(4) 0.000(4) 0.023(4) -0.001(4) C22 0.040(5) 0.046(5) 0.042(5) -0.003(4) 0.025(4) -0.002(4) C23 0.047(5) 0.050(5) 0.053(5) -0.008(4) 0.026(5) -0.003(4) C24 0.028(4) 0.048(5) 0.055(5) -0.012(4) 0.019(4) 0.002(3) C25 0.036(5) 0.054(5) 0.033(4) 0.003(4) 0.020(4) 0.001(4) C26 0.038(5) 0.035(4) 0.046(5) 0.001(3) 0.023(4) -0.002(3) C27 0.035(5) 0.060(5) 0.034(4) 0.003(4) 0.018(4) 0.000(4) C28 0.050(5) 0.037(4) 0.044(5) 0.002(4) 0.026(4) 0.004(4) C29 0.136(13) 0.053(8) 0.080(9) 0.000 0.044(9) 0.000 C30 0.068(9) 0.090(11) 0.063(8) 0.000 0.034(7) 0.000 N1 0.043(4) 0.035(3) 0.042(4) -0.003(3) 0.024(4) -0.002(3) N2 0.177(13) 0.098(10) 0.145(11) 0.000 0.114(10) 0.000 N3 0.081(5) 0.099(6) 0.043(4) 0.004(4) 0.028(4) 0.025(4) N4 0.054(5) 0.090(5) 0.074(5) -0.021(4) 0.032(4) -0.012(4) N5 0.057(5) 0.076(5) 0.053(4) -0.004(4) 0.022(4) 0.011(4) N6 0.053(4) 0.068(5) 0.076(5) -0.003(4) 0.042(4) -0.006(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 C1 1.902(7) . ? C1 C2 1.361(8) . ? C1 C6 1.380(8) . ? C2 C3 1.377(9) . ? C2 H2 0.9300 . ? C3 C4 1.368(8) . ? C3 H3 0.9300 . ? C4 C5 1.385(7) . ? C4 C7 1.505(8) . ? C5 C6 1.379(8) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.508(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.335(9) . ? C8 N1 1.338(7) . ? C8 H8 0.9300 . ? C9 C10 1.343(8) . ? C9 H9 0.9300 . ? C10 C11 1.412(8) . ? C10 H10 0.9300 . ? C11 C16 1.372(8) . ? C11 C12 1.414(8) . ? C12 C13 1.372(8) . ? C12 H12 0.9300 . ? C13 C14 1.367(8) . ? C13 H13 0.9300 . ? C14 C15 1.367(8) . ? C14 H14 0.9300 . ? C15 C16 1.419(7) . ? C15 H15 0.9300 . ? C16 N1 1.401(7) . ? C17 N3 1.144(7) . ? C17 C19 1.404(8) . ? C18 N4 1.135(8) . ? C18 C19 1.389(9) . ? C19 C20 1.428(8) . ? C20 C22 1.418(7) . ? C20 C21 1.434(8) . ? C21 C22 1.351(8) 7_566 ? C21 H21 0.9300 . ? C22 C21 1.351(8) 7_566 ? C22 H22 0.9300 . ? C23 N5 1.160(8) . ? C23 C25 1.383(9) . ? C24 N6 1.141(7) . ? C24 C25 1.416(8) . ? C25 C26 1.412(8) . ? C26 C28 1.402(8) . ? C26 C27 1.417(8) . ? C27 C28 1.375(8) 7_556 ? C27 H27 0.9300 . ? C28 C27 1.375(8) 7_556 ? C28 H28 0.9300 . ? C29 C30 1.407(15) . ? C30 N2 1.156(14) . ? 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 C2 C1 C6 121.4(7) . . ? C2 C1 Br1 119.7(6) . . ? C6 C1 Br1 119.0(6) . . ? C1 C2 C3 118.8(7) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 121.9(7) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 118.2(7) . . ? C3 C4 C7 120.7(6) . . ? C5 C4 C7 121.1(6) . . ? C6 C5 C4 121.1(6) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 118.6(7) . . ? C5 C6 H6 120.7 . . ? C1 C6 H6 120.7 . . ? C4 C7 N1 111.0(5) . . ? C4 C7 H7A 109.4 . . ? N1 C7 H7A 109.4 . . ? C4 C7 H7B 109.4 . . ? N1 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C9 C8 N1 124.7(7) . . ? C9 C8 H8 117.7 . . ? N1 C8 H8 117.7 . . ? C8 C9 C10 116.6(7) . . ? C8 C9 H9 121.7 . . ? C10 C9 H9 121.7 . . ? C9 C10 C11 122.7(7) . . ? C9 C10 H10 118.7 . . ? C11 C10 H10 118.7 . . ? C16 C11 C10 118.5(7) . . ? C16 C11 C12 117.8(7) . . ? C10 C11 C12 123.7(7) . . ? C13 C12 C11 120.4(7) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 121.2(7) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C15 C14 C13 120.3(7) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 119.1(6) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? C11 C16 N1 117.9(6) . . ? C11 C16 C15 121.2(7) . . ? N1 C16 C15 120.9(6) . . ? N3 C17 C19 177.2(8) . . ? N4 C18 C19 177.8(8) . . ? C18 C19 C17 118.9(6) . . ? C18 C19 C20 120.5(6) . . ? C17 C19 C20 120.5(6) . . ? C22 C20 C19 121.6(6) . . ? C22 C20 C21 115.9(6) . . ? C19 C20 C21 122.4(6) . . ? C22 C21 C20 121.8(6) 7_566 . ? C22 C21 H21 119.1 7_566 . ? C20 C21 H21 119.1 . . ? C21 C22 C20 122.2(6) 7_566 . ? C21 C22 H22 118.9 7_566 . ? C20 C22 H22 118.9 . . ? N5 C23 C25 179.8(9) . . ? N6 C24 C25 177.7(8) . . ? C23 C25 C26 122.0(6) . . ? C23 C25 C24 118.0(6) . . ? C26 C25 C24 119.9(6) . . ? C28 C26 C25 121.9(7) . . ? C28 C26 C27 116.2(6) . . ? C25 C26 C27 121.9(6) . . ? C28 C27 C26 123.5(6) 7_556 . ? C28 C27 H27 118.2 7_556 . ? C26 C27 H27 118.2 . . ? C27 C28 C26 120.3(6) 7_556 . ? C27 C28 H28 119.9 7_556 . ? C26 C28 H28 119.9 . . ? N2 C30 C29 180.000(7) . . ? C8 N1 C16 119.5(6) . . ? C8 N1 C7 118.5(6) . . ? C16 N1 C7 121.9(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 C1 C2 C3 -0.1(12) . . . . ? Br1 C1 C2 C3 178.9(6) . . . . ? C1 C2 C3 C4 1.4(12) . . . . ? C2 C3 C4 C5 -1.3(10) . . . . ? C2 C3 C4 C7 -178.3(7) . . . . ? C3 C4 C5 C6 -0.1(9) . . . . ? C7 C4 C5 C6 176.9(6) . . . . ? C4 C5 C6 C1 1.3(10) . . . . ? C2 C1 C6 C5 -1.2(11) . . . . ? Br1 C1 C6 C5 179.7(5) . . . . ? C3 C4 C7 N1 69.0(7) . . . . ? C5 C4 C7 N1 -107.9(6) . . . . ? N1 C8 C9 C10 2.2(10) . . . . ? C8 C9 C10 C11 0.0(10) . . . . ? C9 C10 C11 C16 -0.5(9) . . . . ? C9 C10 C11 C12 176.5(6) . . . . ? C16 C11 C12 C13 -0.5(9) . . . . ? C10 C11 C12 C13 -177.5(6) . . . . ? C11 C12 C13 C14 -0.5(10) . . . . ? C12 C13 C14 C15 -0.3(10) . . . . ? C13 C14 C15 C16 2.0(9) . . . . ? C10 C11 C16 N1 -1.0(8) . . . . ? C12 C11 C16 N1 -178.1(5) . . . . ? C10 C11 C16 C15 179.4(5) . . . . ? C12 C11 C16 C15 2.2(9) . . . . ? C14 C15 C16 C11 -3.0(9) . . . . ? C14 C15 C16 N1 177.3(5) . . . . ? N4 C18 C19 C17 57(24) . . . . ? N4 C18 C19 C20 -121(23) . . . . ? N3 C17 C19 C18 -98(18) . . . . ? N3 C17 C19 C20 79(18) . . . . ? C18 C19 C20 C22 -1.5(10) . . . . ? C17 C19 C20 C22 -179.0(6) . . . . ? C18 C19 C20 C21 178.5(6) . . . . ? C17 C19 C20 C21 1.0(10) . . . . ? C22 C20 C21 C22 1.1(10) . . . 7_566 ? C19 C20 C21 C22 -178.9(6) . . . 7_566 ? C19 C20 C22 C21 178.9(6) . . . 7_566 ? C21 C20 C22 C21 -1.2(10) . . . 7_566 ? N5 C23 C25 C26 -145(100) . . . . ? N5 C23 C25 C24 32(100) . . . . ? N6 C24 C25 C23 -85(20) . . . . ? N6 C24 C25 C26 91(20) . . . . ? C23 C25 C26 C28 177.9(6) . . . . ? C24 C25 C26 C28 1.1(9) . . . . ? C23 C25 C26 C27 -3.6(10) . . . . ? C24 C25 C26 C27 179.7(6) . . . . ? C28 C26 C27 C28 0.3(10) . . . 7_556 ? C25 C26 C27 C28 -178.3(6) . . . 7_556 ? C25 C26 C28 C27 178.3(6) . . . 7_556 ? C27 C26 C28 C27 -0.3(10) . . . 7_556 ? C9 C8 N1 C16 -3.7(10) . . . . ? C9 C8 N1 C7 172.8(6) . . . . ? C11 C16 N1 C8 3.0(8) . . . . ? C15 C16 N1 C8 -177.4(5) . . . . ? C11 C16 N1 C7 -173.4(5) . . . . ? C15 C16 N1 C7 6.2(8) . . . . ? C4 C7 N1 C8 -91.6(7) . . . . ? C4 C7 N1 C16 84.9(7) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.926 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.100 #===========END