Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Edwin Kroke' _publ_contact_author_email EDWIN.KROKE@CHEMIE.TU-FREIBERG.DE _publ_section_title ; C6N7Cl[N(C6H5)2]2 * p-C6H4Me2N - A mono-chloro-tri-s-triazine adduct ; loop_ _publ_author_name 'Edwin Kroke' 'Anke Schwarzer' # Attachment 'ansc106_0m.cif' data_ansc106 _database_code_depnum_ccdc_archive 'CCDC 753726' #TrackingRef 'ansc106_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5,8-Bis-(diphenylamino)-1-chloro-tri-s-triazine ; _chemical_name_common 5,8-Bis-(diphenylamino)-1-chloro-tri-s-triazine _chemical_formula_moiety 'C30 H20 Cl N9, C8 H10' _chemical_formula_sum 'C38 H30 Cl N9' _chemical_formula_weight 648.16 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 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.2050(5) _cell_length_b 9.4560(4) _cell_length_c 24.7016(10) _cell_angle_alpha 90.00 _cell_angle_beta 106.356(2) _cell_angle_gamma 90.00 _cell_volume 3183.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9920 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 30.47 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 0.165 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 47117 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 30.00 _reflns_number_total 9271 _reflns_number_gt 6889 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2007)' _computing_cell_refinement 'Bruker SMART (Bruker, 2007)' _computing_data_reduction 'Bruker SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 2007)' _computing_publication_material 'Bruker SHELXTL (Bruker, 2007)' _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^)+(0.0558P)^2^+0.4069P] 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 9271 _refine_ls_number_parameters 435 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1107 _refine_ls_wR_factor_gt 0.1023 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.70896(2) 0.18169(3) 0.047336(13) 0.02078(8) Uani 1 1 d . . . N1 N 0.58786(7) 0.08831(11) 0.09968(4) 0.0156(2) Uani 1 1 d . . . N2 N 0.48412(7) -0.01091(11) 0.14659(4) 0.0156(2) Uani 1 1 d . . . N3 N 0.30847(7) 0.00841(11) 0.10682(4) 0.0156(2) Uani 1 1 d . . . N4 N 0.24505(7) 0.11859(11) 0.02171(4) 0.0154(2) Uani 1 1 d . . . N5 N 0.35320(7) 0.19985(11) -0.03180(4) 0.0156(2) Uani 1 1 d . . . N6 N 0.52119(7) 0.18503(11) 0.00662(4) 0.0161(2) Uani 1 1 d . . . N7 N 0.41665(7) 0.09787(10) 0.05823(4) 0.01278(19) Uani 1 1 d . . . N8 N 0.37393(7) -0.11195(11) 0.18894(4) 0.0154(2) Uani 1 1 d . . . N9 N 0.18413(7) 0.21312(11) -0.06638(4) 0.0159(2) Uani 1 1 d . . . C1 C 0.59099(8) 0.14814(13) 0.05208(5) 0.0150(2) Uani 1 1 d . . . C2 C 0.49673(8) 0.05652(13) 0.10274(5) 0.0139(2) Uani 1 1 d . . . C3 C 0.38962(8) -0.03595(13) 0.14576(5) 0.0142(2) Uani 1 1 d . . . C4 C 0.32146(8) 0.07559(12) 0.06261(5) 0.0138(2) Uani 1 1 d . . . C5 C 0.26370(8) 0.17566(12) -0.02391(5) 0.0142(2) Uani 1 1 d . . . C6 C 0.42902(8) 0.16293(12) 0.01006(5) 0.0139(2) Uani 1 1 d . . . C7 C 0.45002(8) -0.18490(13) 0.22977(5) 0.0153(2) Uani 1 1 d . . . C8 C 0.51162(9) -0.27899(14) 0.21313(5) 0.0189(2) Uani 1 1 d . . . H8 H 0.5054 -0.2936 0.1742 0.023 Uiso 1 1 calc R . . C9 C 0.58240(9) -0.35150(14) 0.25394(6) 0.0228(3) Uani 1 1 d . . . H9 H 0.6247 -0.4160 0.2428 0.027 Uiso 1 1 calc R . . C10 C 0.59201(10) -0.33098(15) 0.31072(6) 0.0250(3) Uani 1 1 d . . . H10 H 0.6416 -0.3795 0.3384 0.030 Uiso 1 1 calc R . . C11 C 0.52892(10) -0.23921(15) 0.32701(6) 0.0249(3) Uani 1 1 d . . . H11 H 0.5345 -0.2263 0.3659 0.030 Uiso 1 1 calc R . . C12 C 0.45755(10) -0.16606(14) 0.28668(5) 0.0204(3) Uani 1 1 d . . . H12 H 0.4142 -0.1035 0.2979 0.024 Uiso 1 1 calc R . . C13 C 0.27476(8) -0.12940(13) 0.19294(5) 0.0152(2) Uani 1 1 d . . . C14 C 0.22790(9) -0.25797(14) 0.17862(5) 0.0199(3) Uani 1 1 d . . . H14 H 0.2594 -0.3332 0.1651 0.024 Uiso 1 1 calc R . . C15 C 0.13379(9) -0.27524(15) 0.18437(6) 0.0230(3) Uani 1 1 d . . . H15 H 0.1005 -0.3627 0.1743 0.028 Uiso 1 1 calc R . . C16 C 0.08838(9) -0.16619(15) 0.20469(5) 0.0221(3) Uani 1 1 d . . . H16 H 0.0245 -0.1791 0.2088 0.027 Uiso 1 1 calc R . . C17 C 0.13633(9) -0.03780(15) 0.21900(5) 0.0219(3) Uani 1 1 d . . . H17 H 0.1054 0.0370 0.2332 0.026 Uiso 1 1 calc R . . C18 C 0.22945(9) -0.01888(14) 0.21259(5) 0.0188(2) Uani 1 1 d . . . H18 H 0.2620 0.0694 0.2216 0.023 Uiso 1 1 calc R . . C19 C 0.18832(8) 0.24961(13) -0.12225(5) 0.0161(2) Uani 1 1 d . . . C20 C 0.13854(9) 0.36877(14) -0.14836(6) 0.0210(3) Uani 1 1 d . . . H20 H 0.1057 0.4284 -0.1286 0.025 Uiso 1 1 calc R . . C21 C 0.13689(9) 0.40061(15) -0.20362(6) 0.0237(3) Uani 1 1 d . . . H21 H 0.1026 0.4818 -0.2216 0.028 Uiso 1 1 calc R . . C22 C 0.18525(9) 0.31414(15) -0.23254(5) 0.0225(3) Uani 1 1 d . . . H22 H 0.1838 0.3355 -0.2703 0.027 Uiso 1 1 calc R . . C23 C 0.23583(9) 0.19612(14) -0.20583(5) 0.0209(3) Uani 1 1 d . . . H23 H 0.2697 0.1375 -0.2254 0.025 Uiso 1 1 calc R . . C24 C 0.23737(9) 0.16302(13) -0.15087(5) 0.0177(2) Uani 1 1 d . . . H24 H 0.2717 0.0818 -0.1329 0.021 Uiso 1 1 calc R . . C25 C 0.08814(8) 0.20008(13) -0.05700(5) 0.0165(2) Uani 1 1 d . . . C26 C 0.05459(10) 0.30668(15) -0.02893(6) 0.0259(3) Uani 1 1 d . . . H26 H 0.0936 0.3882 -0.0163 0.031 Uiso 1 1 calc R . . C27 C -0.03712(11) 0.29328(16) -0.01938(7) 0.0315(3) Uani 1 1 d . . . H27 H -0.0605 0.3656 0.0002 0.038 Uiso 1 1 calc R . . C28 C -0.09413(10) 0.17507(16) -0.03827(6) 0.0263(3) Uani 1 1 d . . . H28 H -0.1570 0.1669 -0.0321 0.032 Uiso 1 1 calc R . . C29 C -0.05979(9) 0.06893(16) -0.06603(5) 0.0239(3) Uani 1 1 d . . . H29 H -0.0987 -0.0128 -0.0786 0.029 Uiso 1 1 calc R . . C30 C 0.03183(9) 0.08140(14) -0.07563(5) 0.0203(3) Uani 1 1 d . . . H30 H 0.0554 0.0086 -0.0949 0.024 Uiso 1 1 calc R . . C31 C 0.30996(10) 0.40040(15) 0.11362(6) 0.0248(3) Uani 1 1 d . . . C32 C 0.32649(11) 0.49009(16) 0.07274(6) 0.0299(3) Uani 1 1 d . . . H32 H 0.2721 0.5327 0.0463 0.036 Uiso 1 1 calc R . . C33 C 0.42079(11) 0.51906(16) 0.06961(6) 0.0287(3) Uani 1 1 d . . . H33 H 0.4296 0.5803 0.0410 0.034 Uiso 1 1 calc R . . C34 C 0.50222(10) 0.45969(15) 0.10779(6) 0.0236(3) Uani 1 1 d . . . C35 C 0.48577(10) 0.36971(14) 0.14897(6) 0.0235(3) Uani 1 1 d . . . H35 H 0.5401 0.3275 0.1756 0.028 Uiso 1 1 calc R . . C36 C 0.39175(11) 0.34093(14) 0.15166(6) 0.0235(3) Uani 1 1 d . . . H36 H 0.3828 0.2791 0.1801 0.028 Uiso 1 1 calc R . . C37 C 0.20809(12) 0.36715(19) 0.11740(7) 0.0370(4) Uani 1 1 d . . . H37A H 0.1648 0.4478 0.1033 0.056 Uiso 1 1 calc R . . H37B H 0.2104 0.3487 0.1568 0.056 Uiso 1 1 calc R . . H37C H 0.1829 0.2834 0.0945 0.056 Uiso 1 1 calc R . . C38 C 0.60480(11) 0.49491(17) 0.10600(7) 0.0357(4) Uani 1 1 d . . . H38A H 0.6082 0.4897 0.0670 0.053 Uiso 1 1 calc R . . H38B H 0.6511 0.4272 0.1293 0.053 Uiso 1 1 calc R . . H38C H 0.6218 0.5907 0.1206 0.053 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01227(13) 0.02722(17) 0.02351(16) 0.00297(12) 0.00614(10) -0.00073(11) N1 0.0121(4) 0.0176(5) 0.0171(5) 0.0010(4) 0.0042(4) -0.0002(4) N2 0.0135(5) 0.0167(5) 0.0163(5) 0.0013(4) 0.0036(4) 0.0001(4) N3 0.0140(5) 0.0179(5) 0.0150(5) 0.0016(4) 0.0041(4) 0.0002(4) N4 0.0127(5) 0.0174(5) 0.0159(5) 0.0021(4) 0.0037(4) 0.0006(4) N5 0.0129(4) 0.0189(5) 0.0149(5) 0.0024(4) 0.0035(3) -0.0011(4) N6 0.0129(5) 0.0191(5) 0.0167(5) 0.0009(4) 0.0051(4) -0.0015(4) N7 0.0110(4) 0.0149(5) 0.0126(4) 0.0003(4) 0.0035(3) -0.0003(4) N8 0.0134(5) 0.0174(5) 0.0165(5) 0.0026(4) 0.0058(4) 0.0005(4) N9 0.0118(4) 0.0196(5) 0.0163(5) 0.0035(4) 0.0040(4) 0.0002(4) C1 0.0118(5) 0.0150(6) 0.0186(6) -0.0014(5) 0.0051(4) -0.0002(4) C2 0.0128(5) 0.0137(6) 0.0148(5) -0.0007(4) 0.0030(4) 0.0012(4) C3 0.0153(5) 0.0140(6) 0.0140(5) -0.0007(4) 0.0050(4) 0.0000(4) C4 0.0120(5) 0.0141(6) 0.0159(5) -0.0017(4) 0.0047(4) -0.0005(4) C5 0.0131(5) 0.0135(6) 0.0156(5) -0.0001(4) 0.0034(4) -0.0011(4) C6 0.0144(5) 0.0136(6) 0.0142(5) -0.0011(4) 0.0050(4) -0.0013(4) C7 0.0147(5) 0.0142(6) 0.0166(6) 0.0029(5) 0.0036(4) -0.0015(4) C8 0.0188(6) 0.0195(6) 0.0203(6) 0.0016(5) 0.0084(5) 0.0006(5) C9 0.0170(6) 0.0217(7) 0.0317(7) 0.0068(6) 0.0100(5) 0.0032(5) C10 0.0185(6) 0.0250(7) 0.0277(7) 0.0104(6) 0.0002(5) -0.0010(5) C11 0.0299(7) 0.0254(7) 0.0166(6) 0.0025(5) 0.0019(5) -0.0025(6) C12 0.0241(6) 0.0185(6) 0.0189(6) -0.0001(5) 0.0067(5) 0.0003(5) C13 0.0143(5) 0.0187(6) 0.0129(5) 0.0036(5) 0.0043(4) 0.0004(4) C14 0.0202(6) 0.0167(6) 0.0224(6) 0.0023(5) 0.0054(5) 0.0013(5) C15 0.0197(6) 0.0213(7) 0.0266(7) 0.0060(5) 0.0042(5) -0.0031(5) C16 0.0150(6) 0.0330(8) 0.0184(6) 0.0069(5) 0.0050(4) -0.0002(5) C17 0.0191(6) 0.0284(7) 0.0197(6) -0.0007(5) 0.0078(5) 0.0041(5) C18 0.0186(6) 0.0199(6) 0.0182(6) -0.0009(5) 0.0054(4) -0.0005(5) C19 0.0126(5) 0.0189(6) 0.0159(5) 0.0030(5) 0.0022(4) -0.0025(4) C20 0.0156(6) 0.0224(7) 0.0254(7) 0.0065(5) 0.0065(5) 0.0031(5) C21 0.0175(6) 0.0266(7) 0.0260(7) 0.0115(6) 0.0045(5) 0.0029(5) C22 0.0185(6) 0.0305(7) 0.0176(6) 0.0049(5) 0.0034(4) -0.0057(5) C23 0.0200(6) 0.0237(7) 0.0191(6) -0.0029(5) 0.0058(5) -0.0037(5) C24 0.0150(5) 0.0167(6) 0.0198(6) 0.0016(5) 0.0021(4) -0.0010(4) C25 0.0121(5) 0.0209(6) 0.0159(6) 0.0046(5) 0.0033(4) 0.0013(4) C26 0.0225(6) 0.0205(7) 0.0364(8) -0.0049(6) 0.0108(5) -0.0018(5) C27 0.0269(7) 0.0299(8) 0.0424(9) -0.0030(7) 0.0174(6) 0.0063(6) C28 0.0159(6) 0.0368(8) 0.0277(7) 0.0078(6) 0.0089(5) 0.0028(5) C29 0.0175(6) 0.0312(8) 0.0218(6) 0.0028(6) 0.0035(5) -0.0060(5) C30 0.0183(6) 0.0242(7) 0.0186(6) 0.0000(5) 0.0054(4) -0.0008(5) C31 0.0280(7) 0.0228(7) 0.0261(7) -0.0081(6) 0.0120(5) -0.0019(5) C32 0.0312(8) 0.0290(8) 0.0270(7) 0.0022(6) 0.0040(6) 0.0023(6) C33 0.0378(8) 0.0273(8) 0.0222(7) 0.0024(6) 0.0104(6) -0.0056(6) C34 0.0286(7) 0.0192(7) 0.0246(7) -0.0077(5) 0.0100(5) -0.0049(5) C35 0.0294(7) 0.0179(7) 0.0208(6) -0.0029(5) 0.0033(5) -0.0003(5) C36 0.0364(8) 0.0181(7) 0.0184(6) -0.0027(5) 0.0115(5) -0.0047(5) C37 0.0331(8) 0.0397(9) 0.0445(9) -0.0112(8) 0.0211(7) -0.0034(7) C38 0.0325(8) 0.0321(9) 0.0470(10) -0.0126(7) 0.0187(7) -0.0118(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1 1.7417(11) . ? N1 C1 1.3168(15) . ? N1 C2 1.3516(14) . ? N2 C2 1.3121(15) . ? N2 C3 1.3575(14) . ? N3 C4 1.3205(15) . ? N3 C3 1.3437(15) . ? N4 C4 1.3217(15) . ? N4 C5 1.3414(15) . ? N5 C6 1.3130(15) . ? N5 C5 1.3587(14) . ? N6 C1 1.3187(15) . ? N6 C6 1.3519(14) . ? N7 C6 1.3939(14) . ? N7 C2 1.3969(14) . ? N7 C4 1.4024(14) . ? N8 C3 1.3557(15) . ? N8 C7 1.4309(15) . ? N8 C13 1.4491(14) . ? N9 C5 1.3549(15) . ? N9 C19 1.4400(15) . ? N9 C25 1.4512(14) . ? C7 C8 1.3887(17) . ? C7 C12 1.3910(17) . ? C8 C9 1.3880(18) . ? C8 H8 0.9500 . ? C9 C10 1.384(2) . ? C9 H9 0.9500 . ? C10 C11 1.386(2) . ? C10 H10 0.9500 . ? C11 C12 1.3891(18) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.3834(18) . ? C13 C18 1.3849(17) . ? C14 C15 1.3931(17) . ? C14 H14 0.9500 . ? C15 C16 1.3834(19) . ? C15 H15 0.9500 . ? C16 C17 1.3882(19) . ? C16 H16 0.9500 . ? C17 C18 1.3874(17) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.3888(18) . ? C19 C24 1.3903(17) . ? C20 C21 1.3916(18) . ? C20 H20 0.9500 . ? C21 C22 1.3882(19) . ? C21 H21 0.9500 . ? C22 C23 1.3893(19) . ? C22 H22 0.9500 . ? C23 C24 1.3873(18) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C30 1.3797(18) . ? C25 C26 1.3821(18) . ? C26 C27 1.3935(19) . ? C26 H26 0.9500 . ? C27 C28 1.382(2) . ? C27 H27 0.9500 . ? C28 C29 1.380(2) . ? C28 H28 0.9500 . ? C29 C30 1.3920(17) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 C32 1.388(2) . ? C31 C36 1.391(2) . ? C31 C37 1.509(2) . ? C32 C33 1.391(2) . ? C32 H32 0.9500 . ? C33 C34 1.389(2) . ? C33 H33 0.9500 . ? C34 C35 1.3954(19) . ? C34 C38 1.5075(19) . ? C35 C36 1.3829(19) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 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 114.77(10) . . ? C2 N2 C3 115.88(10) . . ? C4 N3 C3 116.78(9) . . ? C4 N4 C5 116.87(10) . . ? C6 N5 C5 115.82(10) . . ? C1 N6 C6 114.50(10) . . ? C6 N7 C2 121.66(9) . . ? C6 N7 C4 119.22(9) . . ? C2 N7 C4 119.11(9) . . ? C3 N8 C7 123.45(9) . . ? C3 N8 C13 119.50(9) . . ? C7 N8 C13 116.93(9) . . ? C5 N9 C19 123.65(9) . . ? C5 N9 C25 118.08(10) . . ? C19 N9 C25 117.88(9) . . ? N1 C1 N6 131.90(10) . . ? N1 C1 Cl1 114.42(8) . . ? N6 C1 Cl1 113.67(9) . . ? N2 C2 N1 120.65(10) . . ? N2 C2 N7 121.03(10) . . ? N1 C2 N7 118.32(10) . . ? N3 C3 N8 115.51(10) . . ? N3 C3 N2 127.00(10) . . ? N8 C3 N2 117.48(10) . . ? N3 C4 N4 120.28(10) . . ? N3 C4 N7 119.89(10) . . ? N4 C4 N7 119.80(10) . . ? N4 C5 N9 115.88(10) . . ? N4 C5 N5 127.04(10) . . ? N9 C5 N5 117.08(10) . . ? N5 C6 N6 120.23(10) . . ? N5 C6 N7 121.13(10) . . ? N6 C6 N7 118.63(10) . . ? C8 C7 C12 120.37(11) . . ? C8 C7 N8 120.94(11) . . ? C12 C7 N8 118.58(11) . . ? C9 C8 C7 119.30(12) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C10 C9 C8 120.75(12) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 119.65(12) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C12 120.29(12) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C7 119.60(12) . . ? C11 C12 H12 120.2 . . ? C7 C12 H12 120.2 . . ? C14 C13 C18 121.01(11) . . ? C14 C13 N8 119.32(11) . . ? C18 C13 N8 119.64(11) . . ? C13 C14 C15 118.91(12) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C16 C15 C14 120.56(12) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 119.92(12) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C18 C17 C16 119.93(12) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C13 C18 C17 119.66(12) . . ? C13 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C20 C19 C24 120.28(11) . . ? C20 C19 N9 119.10(11) . . ? C24 C19 N9 120.54(11) . . ? C19 C20 C21 119.79(12) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 120.22(12) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C23 119.56(12) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C24 C23 C22 120.63(12) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C19 119.52(12) . . ? C23 C24 H24 120.2 . . ? C19 C24 H24 120.2 . . ? C30 C25 C26 120.74(11) . . ? C30 C25 N9 119.90(11) . . ? C26 C25 N9 119.36(11) . . ? C25 C26 C27 119.31(13) . . ? C25 C26 H26 120.3 . . ? C27 C26 H26 120.3 . . ? C28 C27 C26 120.21(13) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? C29 C28 C27 120.04(12) . . ? C29 C28 H28 120.0 . . ? C27 C28 H28 120.0 . . ? C28 C29 C30 120.09(13) . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? C25 C30 C29 119.61(12) . . ? C25 C30 H30 120.2 . . ? C29 C30 H30 120.2 . . ? C32 C31 C36 117.27(12) . . ? C32 C31 C37 122.26(13) . . ? C36 C31 C37 120.47(13) . . ? C31 C32 C33 121.58(13) . . ? C31 C32 H32 119.2 . . ? C33 C32 H32 119.2 . . ? C34 C33 C32 120.92(13) . . ? C34 C33 H33 119.5 . . ? C32 C33 H33 119.5 . . ? C33 C34 C35 117.60(12) . . ? C33 C34 C38 121.19(13) . . ? C35 C34 C38 121.18(13) . . ? C36 C35 C34 121.15(13) . . ? C36 C35 H35 119.4 . . ? C34 C35 H35 119.4 . . ? C35 C36 C31 121.49(13) . . ? C35 C36 H36 119.3 . . ? C31 C36 H36 119.3 . . ? C31 C37 H37A 109.5 . . ? C31 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C31 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C34 C38 H38A 109.5 . . ? C34 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C34 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 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 N6 1.0(2) . . . . ? C2 N1 C1 Cl1 -177.36(8) . . . . ? C6 N6 C1 N1 3.1(2) . . . . ? C6 N6 C1 Cl1 -178.47(8) . . . . ? C3 N2 C2 N1 179.18(11) . . . . ? C3 N2 C2 N7 -0.50(16) . . . . ? C1 N1 C2 N2 175.96(11) . . . . ? C1 N1 C2 N7 -4.34(16) . . . . ? C6 N7 C2 N2 -176.58(11) . . . . ? C4 N7 C2 N2 4.58(17) . . . . ? C6 N7 C2 N1 3.73(17) . . . . ? C4 N7 C2 N1 -175.12(10) . . . . ? C4 N3 C3 N8 -176.19(10) . . . . ? C4 N3 C3 N2 4.85(18) . . . . ? C7 N8 C3 N3 170.72(11) . . . . ? C13 N8 C3 N3 -5.21(16) . . . . ? C7 N8 C3 N2 -10.22(17) . . . . ? C13 N8 C3 N2 173.86(10) . . . . ? C2 N2 C3 N3 -4.47(18) . . . . ? C2 N2 C3 N8 176.58(10) . . . . ? C3 N3 C4 N4 177.93(11) . . . . ? C3 N3 C4 N7 -0.23(16) . . . . ? C5 N4 C4 N3 -174.70(11) . . . . ? C5 N4 C4 N7 3.47(16) . . . . ? C6 N7 C4 N3 176.96(11) . . . . ? C2 N7 C4 N3 -4.17(16) . . . . ? C6 N7 C4 N4 -1.22(16) . . . . ? C2 N7 C4 N4 177.65(11) . . . . ? C4 N4 C5 N9 177.12(11) . . . . ? C4 N4 C5 N5 -3.06(18) . . . . ? C19 N9 C5 N4 -167.39(11) . . . . ? C25 N9 C5 N4 5.24(16) . . . . ? C19 N9 C5 N5 12.76(17) . . . . ? C25 N9 C5 N5 -174.60(10) . . . . ? C6 N5 C5 N4 0.00(18) . . . . ? C6 N5 C5 N9 179.82(11) . . . . ? C5 N5 C6 N6 -178.85(11) . . . . ? C5 N5 C6 N7 2.49(17) . . . . ? C1 N6 C6 N5 177.70(11) . . . . ? C1 N6 C6 N7 -3.61(16) . . . . ? C2 N7 C6 N5 179.19(11) . . . . ? C4 N7 C6 N5 -1.96(17) . . . . ? C2 N7 C6 N6 0.52(16) . . . . ? C4 N7 C6 N6 179.36(10) . . . . ? C3 N8 C7 C8 -52.71(17) . . . . ? C13 N8 C7 C8 123.31(12) . . . . ? C3 N8 C7 C12 131.00(12) . . . . ? C13 N8 C7 C12 -52.97(15) . . . . ? C12 C7 C8 C9 -1.56(18) . . . . ? N8 C7 C8 C9 -177.78(11) . . . . ? C7 C8 C9 C10 0.02(19) . . . . ? C8 C9 C10 C11 1.4(2) . . . . ? C9 C10 C11 C12 -1.2(2) . . . . ? C10 C11 C12 C7 -0.3(2) . . . . ? C8 C7 C12 C11 1.70(19) . . . . ? N8 C7 C12 C11 178.01(11) . . . . ? C3 N8 C13 C14 105.08(13) . . . . ? C7 N8 C13 C14 -71.11(14) . . . . ? C3 N8 C13 C18 -76.84(15) . . . . ? C7 N8 C13 C18 106.97(13) . . . . ? C18 C13 C14 C15 -0.14(18) . . . . ? N8 C13 C14 C15 177.90(11) . . . . ? C13 C14 C15 C16 -0.75(19) . . . . ? C14 C15 C16 C17 0.64(19) . . . . ? C15 C16 C17 C18 0.36(19) . . . . ? C14 C13 C18 C17 1.14(18) . . . . ? N8 C13 C18 C17 -176.91(11) . . . . ? C16 C17 C18 C13 -1.24(19) . . . . ? C5 N9 C19 C20 -134.17(13) . . . . ? C25 N9 C19 C20 53.18(15) . . . . ? C5 N9 C19 C24 49.04(17) . . . . ? C25 N9 C19 C24 -123.61(12) . . . . ? C24 C19 C20 C21 0.72(19) . . . . ? N9 C19 C20 C21 -176.08(11) . . . . ? C19 C20 C21 C22 -0.4(2) . . . . ? C20 C21 C22 C23 -0.4(2) . . . . ? C21 C22 C23 C24 0.83(19) . . . . ? C22 C23 C24 C19 -0.46(18) . . . . ? C20 C19 C24 C23 -0.32(18) . . . . ? N9 C19 C24 C23 176.44(11) . . . . ? C5 N9 C25 C30 -96.75(14) . . . . ? C19 N9 C25 C30 76.32(15) . . . . ? C5 N9 C25 C26 82.65(15) . . . . ? C19 N9 C25 C26 -104.28(14) . . . . ? C30 C25 C26 C27 0.1(2) . . . . ? N9 C25 C26 C27 -179.27(12) . . . . ? C25 C26 C27 C28 -0.6(2) . . . . ? C26 C27 C28 C29 0.9(2) . . . . ? C27 C28 C29 C30 -0.7(2) . . . . ? C26 C25 C30 C29 0.00(19) . . . . ? N9 C25 C30 C29 179.39(11) . . . . ? C28 C29 C30 C25 0.30(19) . . . . ? C36 C31 C32 C33 0.3(2) . . . . ? C37 C31 C32 C33 -179.63(14) . . . . ? C31 C32 C33 C34 -0.5(2) . . . . ? C32 C33 C34 C35 0.4(2) . . . . ? C32 C33 C34 C38 -177.69(13) . . . . ? C33 C34 C35 C36 -0.1(2) . . . . ? C38 C34 C35 C36 177.97(13) . . . . ? C34 C35 C36 C31 -0.1(2) . . . . ? C32 C31 C36 C35 0.0(2) . . . . ? C37 C31 C36 C35 179.91(13) . . . . ? 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 C24 H24 N1 0.95 2.51 3.4121(16) 157.8 3_655 C33 H33 N6 0.95 2.69 3.5955(18) 158.8 3_665 C37 H37C N4 0.98 2.71 3.4765(19) 135.5 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.387 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.053