# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Jie Wu' 'Zhiyuan Chen' 'Xiaodi Yang' _publ_contact_author_name 'Jie Wu' _publ_contact_author_email JIE_WU@FUDAN.EDU.CN _publ_section_title ; AgOTf-Catalyzed Tandem Reaction of N'-(2-Alkynylbenzylidene)hydrazide with Alkyne ; # Attachment '090224.cif' data_090224 _database_code_depnum_ccdc_archive 'CCDC 722722' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21.50 H21 Cl N2' _chemical_formula_weight 342.85 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 Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 11.8040(2) _cell_length_b 13.1961(3) _cell_length_c 23.5991(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3675.96(12) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.770 _exptl_crystal_size_mid 0.680 _exptl_crystal_size_min 0.476 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1448 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.783738 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 19108 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 30.90 _reflns_number_total 10218 _reflns_number_gt 5871 _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^)+(0.2000P)^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 SHELXL _refine_ls_extinction_coef 0.0054(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(3) _refine_ls_number_reflns 10218 _refine_ls_number_parameters 442 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1410 _refine_ls_R_factor_gt 0.0911 _refine_ls_wR_factor_ref 0.3158 _refine_ls_wR_factor_gt 0.2659 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.051 _refine_ls_shift/su_mean 0.002 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 0.4966(2) 0.8498(2) 0.53234(12) 0.0464(6) Uani 1 1 d . . . N2 N 0.5199(2) 0.7496(2) 0.52804(13) 0.0492(7) Uani 1 1 d . . . C1 C 0.4019(3) 0.8955(3) 0.50537(16) 0.0488(8) Uani 1 1 d . . . C2 C 0.3931(3) 0.9968(3) 0.51010(17) 0.0549(9) Uani 1 1 d . . . H2 H 0.3323 1.0288 0.4925 0.066 Uiso 1 1 calc R . . C3 C 0.4722(3) 1.0578(3) 0.54068(16) 0.0502(8) Uani 1 1 d . . . C4 C 0.4624(4) 1.1638(3) 0.54445(18) 0.0600(10) Uani 1 1 d . . . H4 H 0.4024 1.1965 0.5266 0.072 Uiso 1 1 calc R . . C5 C 0.5414(4) 1.2200(3) 0.5746(2) 0.0652(11) Uani 1 1 d . . . H5 H 0.5343 1.2901 0.5764 0.078 Uiso 1 1 calc R . . C6 C 0.6309(4) 1.1727(4) 0.6019(2) 0.0655(11) Uani 1 1 d . . . H6 H 0.6825 1.2112 0.6225 0.079 Uiso 1 1 calc R . . C7 C 0.6442(3) 1.0700(3) 0.59879(17) 0.0562(9) Uani 1 1 d . . . H7 H 0.7047 1.0391 0.6171 0.067 Uiso 1 1 calc R . . C8 C 0.5665(3) 1.0110(3) 0.56794(15) 0.0473(8) Uani 1 1 d . . . C9 C 0.5769(3) 0.9037(3) 0.56238(15) 0.0477(8) Uani 1 1 d . . . C10 C 0.6556(3) 0.8309(3) 0.57840(16) 0.0490(8) Uani 1 1 d . . . H10 H 0.7207 0.8411 0.5998 0.059 Uiso 1 1 calc R . . C11 C 0.6177(3) 0.7403(3) 0.55619(15) 0.0458(7) Uani 1 1 d . . . C12 C 0.6746(3) 0.6393(3) 0.55812(16) 0.0494(8) Uani 1 1 d . . . C13 C 0.7758(3) 0.6281(3) 0.58789(19) 0.0563(9) Uani 1 1 d . . . H13 H 0.8073 0.6829 0.6071 0.068 Uiso 1 1 calc R . . C14 C 0.8303(4) 0.5325(3) 0.5885(2) 0.0699(11) Uani 1 1 d . . . H14 H 0.8979 0.5243 0.6082 0.084 Uiso 1 1 calc R . . C15 C 0.7850(5) 0.4546(4) 0.5611(3) 0.0799(14) Uani 1 1 d . . . H15 H 0.8210 0.3919 0.5623 0.096 Uiso 1 1 calc R . . C16 C 0.6840(5) 0.4644(4) 0.5302(3) 0.0870(16) Uani 1 1 d . . . H16 H 0.6547 0.4099 0.5101 0.104 Uiso 1 1 calc R . . C17 C 0.6297(4) 0.5559(3) 0.5304(2) 0.0694(12) Uani 1 1 d . . . H17 H 0.5610 0.5624 0.5114 0.083 Uiso 1 1 calc R . . C18 C 0.3245(3) 0.8262(3) 0.47581(18) 0.0572(9) Uani 1 1 d . . . H18A H 0.2895 0.7824 0.5038 0.069 Uiso 1 1 calc R . . H18B H 0.3692 0.7834 0.4510 0.069 Uiso 1 1 calc R . . C19 C 0.2318(3) 0.8743(3) 0.44115(17) 0.0561(9) Uani 1 1 d . . . H19A H 0.2659 0.9163 0.4121 0.067 Uiso 1 1 calc R . . H19B H 0.1871 0.9180 0.4655 0.067 Uiso 1 1 calc R . . C20 C 0.1534(4) 0.7972(4) 0.4130(2) 0.0663(11) Uani 1 1 d . . . H20A H 0.1982 0.7531 0.3889 0.080 Uiso 1 1 calc R . . H20B H 0.1189 0.7554 0.4421 0.080 Uiso 1 1 calc R . . C21 C 0.0609(4) 0.8451(5) 0.3779(2) 0.0863(16) Uani 1 1 d . . . H21A H 0.0922 0.8691 0.3428 0.130 Uiso 1 1 calc R . . H21B H 0.0285 0.9008 0.3984 0.130 Uiso 1 1 calc R . . H21C H 0.0032 0.7957 0.3701 0.130 Uiso 1 1 calc R . . N3 N 0.2363(2) 0.8423(2) 0.75639(12) 0.0457(6) Uani 1 1 d . . . N4 N 0.2606(2) 0.7420(2) 0.75637(14) 0.0513(7) Uani 1 1 d . . . C22 C 0.1421(3) 0.8820(3) 0.78448(16) 0.0480(8) Uani 1 1 d . . . C23 C 0.1302(3) 0.9840(3) 0.78156(17) 0.0522(8) Uani 1 1 d . . . H23 H 0.0675 1.0130 0.7991 0.063 Uiso 1 1 calc R . . C24 C 0.2076(3) 1.0497(3) 0.75340(15) 0.0476(8) Uani 1 1 d . . . C25 C 0.1942(3) 1.1572(3) 0.75209(17) 0.0575(9) Uani 1 1 d . . . H25 H 0.1317 1.1865 0.7696 0.069 Uiso 1 1 calc R . . C26 C 0.2711(4) 1.2175(3) 0.72575(19) 0.0620(10) Uani 1 1 d . . . H26 H 0.2607 1.2874 0.7256 0.074 Uiso 1 1 calc R . . C27 C 0.3660(3) 1.1756(3) 0.69875(18) 0.0587(10) Uani 1 1 d . . . H27 H 0.4186 1.2173 0.6810 0.070 Uiso 1 1 calc R . . C28 C 0.3806(3) 1.0714(3) 0.69882(16) 0.0527(9) Uani 1 1 d . . . H28 H 0.4437 1.0438 0.6810 0.063 Uiso 1 1 calc R . . C29 C 0.3022(3) 1.0063(3) 0.72522(14) 0.0452(7) Uani 1 1 d . . . C30 C 0.3155(3) 0.8988(3) 0.72723(14) 0.0431(7) Uani 1 1 d . . . C31 C 0.3956(3) 0.8311(3) 0.70772(17) 0.0504(8) Uani 1 1 d . . . H31 H 0.4601 0.8455 0.6866 0.061 Uiso 1 1 calc R . . C32 C 0.3582(3) 0.7345(3) 0.72699(16) 0.0481(8) Uani 1 1 d . . . C33 C 0.4162(3) 0.6361(3) 0.72286(18) 0.0537(9) Uani 1 1 d . . . C34 C 0.5154(3) 0.6255(3) 0.6916(2) 0.0600(10) Uani 1 1 d . . . H34 H 0.5438 0.6804 0.6714 0.072 Uiso 1 1 calc R . . C35 C 0.5720(4) 0.5334(3) 0.6904(2) 0.0671(11) Uani 1 1 d . . . H35 H 0.6382 0.5273 0.6693 0.081 Uiso 1 1 calc R . . C36 C 0.5324(4) 0.4515(4) 0.7195(2) 0.0760(13) Uani 1 1 d . . . H36 H 0.5711 0.3901 0.7189 0.091 Uiso 1 1 calc R . . C37 C 0.4330(5) 0.4620(4) 0.7501(3) 0.0893(18) Uani 1 1 d . . . H37 H 0.4053 0.4067 0.7702 0.107 Uiso 1 1 calc R . . C38 C 0.3738(4) 0.5520(4) 0.7516(3) 0.0768(14) Uani 1 1 d . . . H38 H 0.3061 0.5566 0.7716 0.092 Uiso 1 1 calc R . . C39 C 0.0652(3) 0.8090(3) 0.81365(18) 0.0522(8) Uani 1 1 d . . . H39A H 0.1106 0.7661 0.8381 0.063 Uiso 1 1 calc R . . H39B H 0.0309 0.7657 0.7852 0.063 Uiso 1 1 calc R . . C40 C -0.0277(3) 0.8554(3) 0.84853(17) 0.0519(8) Uani 1 1 d . . . H40A H -0.0747 0.8972 0.8242 0.062 Uiso 1 1 calc R . . H40B H 0.0057 0.8990 0.8771 0.062 Uiso 1 1 calc R . . C41 C -0.1020(3) 0.7769(4) 0.87766(18) 0.0604(10) Uani 1 1 d . . . H41A H -0.0556 0.7364 0.9029 0.072 Uiso 1 1 calc R . . H41B H -0.1340 0.7320 0.8493 0.072 Uiso 1 1 calc R . . C42 C -0.1979(4) 0.8252(4) 0.9115(2) 0.0773(13) Uani 1 1 d . . . H42A H -0.2578 0.8447 0.8862 0.116 Uiso 1 1 calc R . . H42B H -0.1700 0.8840 0.9310 0.116 Uiso 1 1 calc R . . H42C H -0.2263 0.7773 0.9386 0.116 Uiso 1 1 calc R . . C43 C 0.743(3) 0.5819(11) 0.8953(12) 0.265(16) Uiso 0.50 1 d PD A 1 H43A H 0.8215 0.6008 0.8899 0.318 Uiso 0.50 1 calc PR A 1 H43B H 0.7133 0.6051 0.9314 0.318 Uiso 0.50 1 calc PR A 1 Cl1 Cl 0.6555(7) 0.6028(6) 0.8377(4) 0.199(3) Uiso 0.50 1 d PD A 1 Cl2 Cl 0.7108(10) 0.4604(7) 0.8783(5) 0.237(4) Uiso 0.50 1 d PD A 1 C44 C 0.4926(11) 0.5302(8) 0.8973(6) 0.107(4) Uiso 0.50 1 d PD B 2 H44A H 0.4804 0.5564 0.8593 0.129 Uiso 0.50 1 calc PR B 2 H44B H 0.4225 0.5060 0.9139 0.129 Uiso 0.50 1 calc PR B 2 Cl3 Cl 0.6072(11) 0.4438(8) 0.9027(7) 0.289(5) Uiso 0.50 1 d PD B 2 Cl4 Cl 0.5680(7) 0.6084(6) 0.9399(4) 0.207(3) Uiso 0.50 1 d PD B 2 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 0.0402(13) 0.0498(15) 0.0491(16) 0.0040(13) -0.0010(11) -0.0027(12) N2 0.0448(14) 0.0502(16) 0.0528(16) 0.0038(13) -0.0026(12) -0.0006(12) C1 0.0386(15) 0.058(2) 0.0501(19) 0.0084(16) -0.0045(13) 0.0036(14) C2 0.0472(18) 0.061(2) 0.057(2) 0.0078(18) -0.0006(15) 0.0106(16) C3 0.0442(16) 0.055(2) 0.051(2) 0.0050(16) 0.0053(13) 0.0041(14) C4 0.053(2) 0.065(2) 0.062(2) 0.0006(19) 0.0034(17) 0.0060(18) C5 0.068(2) 0.049(2) 0.079(3) 0.001(2) 0.006(2) -0.0007(18) C6 0.064(2) 0.061(2) 0.071(3) 0.000(2) 0.0007(19) -0.010(2) C7 0.0528(19) 0.060(2) 0.056(2) -0.0012(18) 0.0003(16) -0.0020(17) C8 0.0459(16) 0.0522(19) 0.0438(19) 0.0044(15) 0.0027(13) 0.0018(14) C9 0.0441(15) 0.058(2) 0.0412(17) 0.0065(16) -0.0039(13) -0.0018(14) C10 0.0465(17) 0.054(2) 0.0469(19) 0.0047(15) -0.0064(13) 0.0033(15) C11 0.0439(16) 0.0486(18) 0.0448(17) 0.0051(15) 0.0012(13) 0.0034(14) C12 0.0450(16) 0.050(2) 0.0529(19) 0.0048(16) -0.0008(14) -0.0001(14) C13 0.0539(19) 0.051(2) 0.064(2) -0.0020(18) -0.0087(17) 0.0041(16) C14 0.061(2) 0.060(3) 0.089(3) -0.001(2) -0.007(2) 0.012(2) C15 0.080(3) 0.058(3) 0.101(4) -0.008(2) -0.002(3) 0.005(2) C16 0.077(3) 0.064(3) 0.120(4) -0.005(3) -0.003(3) 0.007(2) C17 0.071(3) 0.050(2) 0.087(3) -0.004(2) -0.014(2) -0.0081(19) C18 0.0435(17) 0.067(2) 0.061(2) -0.0006(19) -0.0042(15) 0.0018(16) C19 0.0458(18) 0.071(3) 0.052(2) -0.0035(18) -0.0077(15) 0.0047(16) C20 0.053(2) 0.082(3) 0.064(3) 0.003(2) -0.0119(17) -0.001(2) C21 0.063(3) 0.114(4) 0.082(3) -0.006(3) -0.033(2) 0.006(3) N3 0.0406(13) 0.0501(16) 0.0464(16) 0.0005(13) 0.0029(11) 0.0001(12) N4 0.0437(14) 0.0513(16) 0.0588(18) -0.0003(14) 0.0061(12) 0.0021(12) C22 0.0362(14) 0.058(2) 0.0502(19) -0.0060(16) 0.0012(13) -0.0016(13) C23 0.0428(16) 0.060(2) 0.053(2) -0.0070(18) 0.0023(14) 0.0029(15) C24 0.0447(15) 0.0523(19) 0.0457(18) 0.0006(15) -0.0026(13) -0.0013(14) C25 0.0554(19) 0.061(2) 0.057(2) -0.0037(19) -0.0018(17) 0.0077(17) C26 0.069(2) 0.057(2) 0.060(2) 0.0026(19) -0.0093(19) 0.0017(18) C27 0.060(2) 0.063(2) 0.054(2) 0.0147(18) -0.0033(17) -0.0101(19) C28 0.0469(17) 0.065(2) 0.047(2) 0.0081(17) 0.0012(14) -0.0041(16) C29 0.0407(14) 0.0544(19) 0.0405(17) 0.0026(15) -0.0060(12) 0.0005(13) C30 0.0387(14) 0.0506(18) 0.0401(16) 0.0009(14) -0.0003(12) 0.0009(13) C31 0.0422(16) 0.056(2) 0.053(2) 0.0037(17) 0.0039(14) -0.0006(15) C32 0.0407(15) 0.0512(19) 0.0525(19) -0.0002(16) 0.0019(13) 0.0012(13) C33 0.0467(17) 0.0495(19) 0.065(2) 0.0005(17) 0.0057(15) 0.0002(14) C34 0.0546(19) 0.053(2) 0.073(3) 0.0048(19) 0.0120(18) 0.0044(17) C35 0.060(2) 0.060(2) 0.081(3) -0.006(2) 0.012(2) 0.005(2) C36 0.067(3) 0.064(3) 0.097(4) 0.006(2) 0.008(2) 0.014(2) C37 0.089(4) 0.054(3) 0.125(5) 0.024(3) 0.029(3) 0.001(2) C38 0.056(2) 0.065(3) 0.108(4) 0.018(3) 0.020(2) 0.0070(19) C39 0.0440(17) 0.054(2) 0.058(2) 0.0005(17) 0.0096(14) -0.0021(15) C40 0.0439(16) 0.059(2) 0.053(2) 0.0005(17) 0.0046(14) 0.0008(15) C41 0.052(2) 0.074(3) 0.055(2) 0.0046(19) 0.0099(15) -0.0041(18) C42 0.058(2) 0.100(4) 0.074(3) -0.007(3) 0.017(2) 0.001(2) _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 N2 1.353(4) . ? N1 C9 1.381(4) . ? N1 C1 1.421(4) . ? N2 C11 1.338(4) . ? C1 C2 1.346(6) . ? C1 C18 1.469(5) . ? C2 C3 1.428(6) . ? C2 H2 0.9300 . ? C3 C4 1.407(6) . ? C3 C8 1.426(5) . ? C4 C5 1.388(6) . ? C4 H4 0.9300 . ? C5 C6 1.387(7) . ? C5 H5 0.9300 . ? C6 C7 1.365(6) . ? C6 H6 0.9300 . ? C7 C8 1.407(5) . ? C7 H7 0.9300 . ? C8 C9 1.426(6) . ? C9 C10 1.390(5) . ? C10 C11 1.379(5) . ? C10 H10 0.9300 . ? C11 C12 1.494(5) . ? C12 C17 1.386(6) . ? C12 C13 1.394(5) . ? C13 C14 1.416(6) . ? C13 H13 0.9300 . ? C14 C15 1.328(7) . ? C14 H14 0.9300 . ? C15 C16 1.402(8) . ? C15 H15 0.9300 . ? C16 C17 1.367(7) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.506(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.528(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.508(6) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? N3 N4 1.354(4) . ? N3 C30 1.380(4) . ? N3 C22 1.397(4) . ? N4 C32 1.348(4) . ? C22 C23 1.355(5) . ? C22 C39 1.492(5) . ? C23 C24 1.423(5) . ? C23 H23 0.9300 . ? C24 C29 1.420(5) . ? C24 C25 1.428(5) . ? C25 C26 1.357(6) . ? C25 H25 0.9300 . ? C26 C27 1.403(6) . ? C26 H26 0.9300 . ? C27 C28 1.385(6) . ? C27 H27 0.9300 . ? C28 C29 1.408(5) . ? C28 H28 0.9300 . ? C29 C30 1.428(5) . ? C30 C31 1.380(5) . ? C31 C32 1.423(5) . ? C31 H31 0.9300 . ? C32 C33 1.472(5) . ? C33 C38 1.393(6) . ? C33 C34 1.391(5) . ? C34 C35 1.389(6) . ? C34 H34 0.9300 . ? C35 C36 1.364(7) . ? C35 H35 0.9300 . ? C36 C37 1.384(7) . ? C36 H36 0.9300 . ? C37 C38 1.379(7) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? C39 C40 1.502(5) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 C41 1.521(5) . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C41 C42 1.525(6) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C43 Cl2 1.695(10) . ? C43 Cl1 1.728(10) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 Cl4 1.693(9) . ? C44 Cl3 1.774(9) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? 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 N2 N1 C9 113.7(3) . . ? N2 N1 C1 122.7(3) . . ? C9 N1 C1 123.4(3) . . ? C11 N2 N1 103.2(3) . . ? C2 C1 N1 116.5(3) . . ? C2 C1 C18 127.6(3) . . ? N1 C1 C18 115.9(3) . . ? C1 C2 C3 123.4(3) . . ? C1 C2 H2 118.3 . . ? C3 C2 H2 118.3 . . ? C4 C3 C8 117.8(4) . . ? C4 C3 C2 122.6(3) . . ? C8 C3 C2 119.6(3) . . ? C5 C4 C3 120.6(4) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C6 C5 C4 120.6(4) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C7 C6 C5 120.6(4) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 120.2(4) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C7 C8 C3 120.1(4) . . ? C7 C8 C9 122.8(3) . . ? C3 C8 C9 117.1(3) . . ? N1 C9 C10 104.0(3) . . ? N1 C9 C8 120.0(3) . . ? C10 C9 C8 136.0(3) . . ? C11 C10 C9 106.2(3) . . ? C11 C10 H10 126.9 . . ? C9 C10 H10 126.9 . . ? N2 C11 C10 112.9(3) . . ? N2 C11 C12 119.0(3) . . ? C10 C11 C12 128.1(3) . . ? C17 C12 C13 118.9(4) . . ? C17 C12 C11 121.5(4) . . ? C13 C12 C11 119.6(3) . . ? C12 C13 C14 119.2(4) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C15 C14 C13 120.2(5) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 121.5(5) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C17 C16 C15 118.7(5) . . ? C17 C16 H16 120.7 . . ? C15 C16 H16 120.7 . . ? C16 C17 C12 121.5(5) . . ? C16 C17 H17 119.2 . . ? C12 C17 H17 119.2 . . ? C1 C18 C19 116.6(3) . . ? C1 C18 H18A 108.1 . . ? C19 C18 H18A 108.1 . . ? C1 C18 H18B 108.2 . . ? C19 C18 H18B 108.1 . . ? H18A C18 H18B 107.3 . . ? C18 C19 C20 113.3(3) . . ? C18 C19 H19A 108.9 . . ? C20 C19 H19A 108.9 . . ? C18 C19 H19B 108.9 . . ? C20 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? C21 C20 C19 113.5(4) . . ? C21 C20 H20A 108.9 . . ? C19 C20 H20A 108.9 . . ? C21 C20 H20B 108.9 . . ? C19 C20 H20B 108.9 . . ? H20A C20 H20B 107.7 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N4 N3 C30 112.6(3) . . ? N4 N3 C22 122.4(3) . . ? C30 N3 C22 125.0(3) . . ? C32 N4 N3 104.7(3) . . ? C23 C22 N3 115.5(3) . . ? C23 C22 C39 127.0(3) . . ? N3 C22 C39 117.5(3) . . ? C22 C23 C24 124.2(3) . . ? C22 C23 H23 117.9 . . ? C24 C23 H23 117.9 . . ? C29 C24 C23 118.5(3) . . ? C29 C24 C25 118.5(3) . . ? C23 C24 C25 122.9(3) . . ? C26 C25 C24 121.2(4) . . ? C26 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? C25 C26 C27 120.7(4) . . ? C25 C26 H26 119.7 . . ? C27 C26 H26 119.7 . . ? C28 C27 C26 119.4(4) . . ? C28 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? C27 C28 C29 121.6(4) . . ? C27 C28 H28 119.2 . . ? C29 C28 H28 119.2 . . ? C28 C29 C24 118.5(3) . . ? C28 C29 C30 123.3(3) . . ? C24 C29 C30 118.1(3) . . ? C31 C30 N3 106.3(3) . . ? C31 C30 C29 135.0(3) . . ? N3 C30 C29 118.6(3) . . ? C30 C31 C32 105.1(3) . . ? C30 C31 H31 127.5 . . ? C32 C31 H31 127.5 . . ? N4 C32 C31 111.3(3) . . ? N4 C32 C33 119.8(3) . . ? C31 C32 C33 128.7(3) . . ? C38 C33 C34 118.8(4) . . ? C38 C33 C32 120.2(4) . . ? C34 C33 C32 121.0(3) . . ? C35 C34 C33 120.3(4) . . ? C35 C34 H34 119.9 . . ? C33 C34 H34 119.9 . . ? C36 C35 C34 121.2(4) . . ? C36 C35 H35 119.4 . . ? C34 C35 H35 119.4 . . ? C35 C36 C37 118.3(4) . . ? C35 C36 H36 120.8 . . ? C37 C36 H36 120.8 . . ? C36 C37 C38 122.0(4) . . ? C36 C37 H37 119.0 . . ? C38 C37 H37 119.0 . . ? C37 C38 C33 119.4(4) . . ? C37 C38 H38 120.3 . . ? C33 C38 H38 120.3 . . ? C22 C39 C40 115.7(3) . . ? C22 C39 H39A 108.4 . . ? C40 C39 H39A 108.4 . . ? C22 C39 H39B 108.4 . . ? C40 C39 H39B 108.4 . . ? H39A C39 H39B 107.4 . . ? C39 C40 C41 113.0(3) . . ? C39 C40 H40A 109.0 . . ? C41 C40 H40A 109.0 . . ? C39 C40 H40B 109.0 . . ? C41 C40 H40B 109.0 . . ? H40A C40 H40B 107.8 . . ? C40 C41 C42 112.3(4) . . ? C40 C41 H41A 109.1 . . ? C42 C41 H41A 109.1 . . ? C40 C41 H41B 109.1 . . ? C42 C41 H41B 109.1 . . ? H41A C41 H41B 107.9 . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? Cl2 C43 Cl1 80.3(7) . . ? Cl2 C43 H43A 115.1 . . ? Cl1 C43 H43A 115.2 . . ? Cl2 C43 H43B 115.3 . . ? Cl1 C43 H43B 115.3 . . ? H43A C43 H43B 112.2 . . ? Cl4 C44 Cl3 87.0(7) . . ? Cl4 C44 H44A 114.2 . . ? Cl3 C44 H44A 114.2 . . ? Cl4 C44 H44B 114.1 . . ? Cl3 C44 H44B 114.2 . . ? H44A C44 H44B 111.3 . . ? 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 N2 C11 0.0(4) . . . . ? C1 N1 N2 C11 176.3(3) . . . . ? N2 N1 C1 C2 -175.7(3) . . . . ? C9 N1 C1 C2 0.2(5) . . . . ? N2 N1 C1 C18 4.7(5) . . . . ? C9 N1 C1 C18 -179.4(3) . . . . ? N1 C1 C2 C3 -0.6(6) . . . . ? C18 C1 C2 C3 178.9(4) . . . . ? C1 C2 C3 C4 179.1(4) . . . . ? C1 C2 C3 C8 0.2(6) . . . . ? C8 C3 C4 C5 -1.0(6) . . . . ? C2 C3 C4 C5 -179.9(4) . . . . ? C3 C4 C5 C6 -0.6(6) . . . . ? C4 C5 C6 C7 1.2(7) . . . . ? C5 C6 C7 C8 -0.3(7) . . . . ? C6 C7 C8 C3 -1.3(6) . . . . ? C6 C7 C8 C9 178.9(4) . . . . ? C4 C3 C8 C7 1.9(5) . . . . ? C2 C3 C8 C7 -179.2(3) . . . . ? C4 C3 C8 C9 -178.3(3) . . . . ? C2 C3 C8 C9 0.6(5) . . . . ? N2 N1 C9 C10 -0.6(4) . . . . ? C1 N1 C9 C10 -176.9(3) . . . . ? N2 N1 C9 C8 176.9(3) . . . . ? C1 N1 C9 C8 0.6(5) . . . . ? C7 C8 C9 N1 178.8(3) . . . . ? C3 C8 C9 N1 -1.0(5) . . . . ? C7 C8 C9 C10 -4.7(7) . . . . ? C3 C8 C9 C10 175.5(4) . . . . ? N1 C9 C10 C11 0.9(4) . . . . ? C8 C9 C10 C11 -175.9(4) . . . . ? N1 N2 C11 C10 0.7(4) . . . . ? N1 N2 C11 C12 -176.8(3) . . . . ? C9 C10 C11 N2 -1.1(4) . . . . ? C9 C10 C11 C12 176.1(4) . . . . ? N2 C11 C12 C17 1.6(6) . . . . ? C10 C11 C12 C17 -175.5(4) . . . . ? N2 C11 C12 C13 -179.2(4) . . . . ? C10 C11 C12 C13 3.8(6) . . . . ? C17 C12 C13 C14 0.5(7) . . . . ? C11 C12 C13 C14 -178.7(4) . . . . ? C12 C13 C14 C15 -0.1(8) . . . . ? C13 C14 C15 C16 1.0(9) . . . . ? C14 C15 C16 C17 -2.3(9) . . . . ? C15 C16 C17 C12 2.8(9) . . . . ? C13 C12 C17 C16 -1.9(8) . . . . ? C11 C12 C17 C16 177.3(5) . . . . ? C2 C1 C18 C19 7.6(6) . . . . ? N1 C1 C18 C19 -172.8(3) . . . . ? C1 C18 C19 C20 -178.6(3) . . . . ? C18 C19 C20 C21 -179.6(4) . . . . ? C30 N3 N4 C32 0.6(4) . . . . ? C22 N3 N4 C32 -177.9(3) . . . . ? N4 N3 C22 C23 178.8(3) . . . . ? C30 N3 C22 C23 0.5(5) . . . . ? N4 N3 C22 C39 -1.9(5) . . . . ? C30 N3 C22 C39 179.8(3) . . . . ? N3 C22 C23 C24 -1.4(5) . . . . ? C39 C22 C23 C24 179.3(4) . . . . ? C22 C23 C24 C29 1.6(6) . . . . ? C22 C23 C24 C25 -178.6(4) . . . . ? C29 C24 C25 C26 -1.5(6) . . . . ? C23 C24 C25 C26 178.7(4) . . . . ? C24 C25 C26 C27 0.3(6) . . . . ? C25 C26 C27 C28 0.4(6) . . . . ? C26 C27 C28 C29 0.2(6) . . . . ? C27 C28 C29 C24 -1.4(5) . . . . ? C27 C28 C29 C30 -178.6(3) . . . . ? C23 C24 C29 C28 -178.1(3) . . . . ? C25 C24 C29 C28 2.0(5) . . . . ? C23 C24 C29 C30 -0.8(5) . . . . ? C25 C24 C29 C30 179.4(3) . . . . ? N4 N3 C30 C31 -0.4(4) . . . . ? C22 N3 C30 C31 178.0(3) . . . . ? N4 N3 C30 C29 -178.2(3) . . . . ? C22 N3 C30 C29 0.2(5) . . . . ? C28 C29 C30 C31 0.1(6) . . . . ? C24 C29 C30 C31 -177.1(4) . . . . ? C28 C29 C30 N3 177.1(3) . . . . ? C24 C29 C30 N3 -0.1(5) . . . . ? N3 C30 C31 C32 0.1(4) . . . . ? C29 C30 C31 C32 177.3(4) . . . . ? N3 N4 C32 C31 -0.5(4) . . . . ? N3 N4 C32 C33 174.3(3) . . . . ? C30 C31 C32 N4 0.3(4) . . . . ? C30 C31 C32 C33 -173.9(4) . . . . ? N4 C32 C33 C38 -3.3(6) . . . . ? C31 C32 C33 C38 170.5(5) . . . . ? N4 C32 C33 C34 178.3(4) . . . . ? C31 C32 C33 C34 -7.9(6) . . . . ? C38 C33 C34 C35 -1.6(7) . . . . ? C32 C33 C34 C35 176.9(4) . . . . ? C33 C34 C35 C36 0.0(8) . . . . ? C34 C35 C36 C37 0.7(9) . . . . ? C35 C36 C37 C38 0.2(10) . . . . ? C36 C37 C38 C33 -1.8(10) . . . . ? C34 C33 C38 C37 2.5(8) . . . . ? C32 C33 C38 C37 -176.0(5) . . . . ? C23 C22 C39 C40 -7.1(6) . . . . ? N3 C22 C39 C40 173.6(3) . . . . ? C22 C39 C40 C41 -179.3(3) . . . . ? C39 C40 C41 C42 -178.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 30.90 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.755 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.072