Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Zao-ying Li' _publ_contact_author_address ; Department of Chemistry Wuhan University Wuhan CHINA ; _publ_contact_author_email ZYLIWUC@WHU.EDU.CN _publ_section_title ; Dipyrrolylquinoxaline-bridged Schiff bases: A new class of fluorescent sensors for mercury(II) ; loop_ _publ_author_name 'Zao-ying Li' 'Jian-Ping Guo' 'Lei Wang' 'Wai-Yeung Wong' ; Wai-Kwok Wong ; 'Xunjin Zhu' data_wy1056wm _database_code_depnum_ccdc_archive 'CCDC 254149' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 N6 Ni' _chemical_formula_weight 425.13 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 13.9137(7) _cell_length_b 16.3936(9) _cell_length_c 24.5367(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5596.7(5) _cell_formula_units_Z 12 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2640 _exptl_absorpt_coefficient_mu 1.062 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.9158 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Smart CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28342 _diffrn_reflns_av_R_equivalents 0.0632 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5459 _reflns_number_gt 3960 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0402P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 5459 _refine_ls_number_parameters 784 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0684 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0856 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.9524(4) 0.7902(3) 0.2837(2) 0.0518(15) Uani 1 1 d . . . C2 C 0.9633(5) 0.8531(4) 0.3225(3) 0.082(2) Uani 1 1 d . . . H2A H 1.0089 0.8938 0.3173 0.098 Uiso 1 1 calc R . . C3 C 0.9064(5) 0.8532(5) 0.3674(3) 0.089(3) Uani 1 1 d . . . H3A H 0.9127 0.8947 0.3930 0.107 Uiso 1 1 calc R . . C4 C 0.8389(5) 0.7923(4) 0.3756(3) 0.0676(19) Uani 1 1 d . . . H4A H 0.8019 0.7931 0.4071 0.081 Uiso 1 1 calc R . . C5 C 0.8253(4) 0.7314(4) 0.3388(3) 0.0578(17) Uani 1 1 d . . . H5A H 0.7783 0.6920 0.3446 0.069 Uiso 1 1 calc R . . C6 C 0.8835(4) 0.7288(3) 0.2918(2) 0.0417(14) Uani 1 1 d . . . C7 C 0.9293(4) 0.6656(3) 0.2111(2) 0.0383(13) Uani 1 1 d . . . C8 C 0.9990(4) 0.7296(3) 0.2016(2) 0.0375(13) Uani 1 1 d . . . C9 C 1.0642(4) 0.7423(3) 0.1556(2) 0.0351(13) Uani 1 1 d . . . C10 C 1.1242(4) 0.8114(3) 0.1518(2) 0.0414(14) Uani 1 1 d . . . H10A H 1.1263 0.8547 0.1763 0.050 Uiso 1 1 calc R . . C11 C 1.1786(4) 0.8038(3) 0.1060(2) 0.0481(15) Uani 1 1 d . . . H11A H 1.2245 0.8405 0.0934 0.058 Uiso 1 1 calc R . . C12 C 1.1524(3) 0.7312(3) 0.0821(2) 0.0376(13) Uani 1 1 d . . . C13 C 1.1827(4) 0.6884(4) 0.0365(3) 0.0517(16) Uani 1 1 d . . . H13A H 1.2324 0.7081 0.0148 0.062 Uiso 1 1 calc R . . C14 C 1.1815(5) 0.5727(4) -0.0211(3) 0.084(2) Uani 1 1 d . . . H14A H 1.1481 0.5869 -0.0545 0.101 Uiso 1 1 calc R . . H14B H 1.2486 0.5873 -0.0256 0.101 Uiso 1 1 calc R . . C15 C 1.1741(5) 0.4842(4) -0.0123(3) 0.084(2) Uani 1 1 d . . . H15A H 1.1773 0.4735 0.0265 0.100 Uiso 1 1 calc R . . H15B H 1.2291 0.4580 -0.0291 0.100 Uiso 1 1 calc R . . C16 C 1.0835(5) 0.4458(5) -0.0347(3) 0.093(3) Uani 1 1 d . . . H16A H 1.0912 0.4373 -0.0736 0.112 Uiso 1 1 calc R . . H16B H 1.0744 0.3929 -0.0178 0.112 Uiso 1 1 calc R . . C17 C 0.9964(5) 0.4962(4) -0.0252(3) 0.078(2) Uani 1 1 d . . . H17A H 0.9404 0.4680 -0.0393 0.094 Uiso 1 1 calc R . . H17B H 1.0025 0.5476 -0.0445 0.094 Uiso 1 1 calc R . . C18 C 0.9149(5) 0.4754(4) 0.0594(3) 0.0504(17) Uani 1 1 d . . . H18A H 0.8815 0.4323 0.0436 0.060 Uiso 1 1 calc R . . C19 C 0.8936(4) 0.5034(3) 0.1120(3) 0.0431(17) Uani 1 1 d . . . C20 C 0.8262(4) 0.4824(3) 0.1511(3) 0.0510(17) Uani 1 1 d . . . H20A H 0.7839 0.4385 0.1496 0.061 Uiso 1 1 calc R . . C21 C 0.8332(4) 0.5386(3) 0.1925(3) 0.0493(16) Uani 1 1 d . . . H21A H 0.7967 0.5401 0.2242 0.059 Uiso 1 1 calc R . . C22 C 0.9077(3) 0.5941(3) 0.1773(2) 0.0352(12) Uani 1 1 d . . . C23 C 0.9658(5) 0.2244(4) 0.9523(3) 0.0675(19) Uani 1 1 d . . . C24 C 0.9771(6) 0.1645(5) 0.9929(4) 0.129(4) Uani 1 1 d . . . H24A H 1.0308 0.1308 0.9921 0.155 Uiso 1 1 calc R . . C25 C 0.9116(6) 0.1554(5) 1.0326(4) 0.115(3) Uani 1 1 d . . . H25A H 0.9199 0.1138 1.0580 0.138 Uiso 1 1 calc R . . C26 C 0.8322(6) 0.2057(4) 1.0371(3) 0.085(2) Uani 1 1 d . . . H26A H 0.7895 0.2002 1.0660 0.102 Uiso 1 1 calc R . . C27 C 0.8183(5) 0.2635(4) 0.9979(3) 0.0651(19) Uani 1 1 d . . . H27A H 0.7642 0.2967 0.9997 0.078 Uiso 1 1 calc R . . C28 C 0.8846(4) 0.2743(3) 0.9547(3) 0.0524(16) Uani 1 1 d . . . C29 C 0.9346(4) 0.3425(3) 0.8766(2) 0.0374(13) Uani 1 1 d . . . C30 C 1.0172(4) 0.2887(3) 0.8740(3) 0.0450(15) Uani 1 1 d . . . C31 C 1.0936(4) 0.2857(3) 0.8331(2) 0.0448(14) Uani 1 1 d . . . C32 C 1.1736(4) 0.2328(4) 0.8393(3) 0.0611(18) Uani 1 1 d . . . H32A H 1.1859 0.1990 0.8689 0.073 Uiso 1 1 calc R . . C33 C 1.2293(4) 0.2408(4) 0.7938(3) 0.069(2) Uani 1 1 d . . . H33A H 1.2862 0.2132 0.7865 0.083 Uiso 1 1 calc R . . C34 C 1.1854(4) 0.2975(4) 0.7608(3) 0.0547(16) Uani 1 1 d . . . C35 C 1.2040(4) 0.3279(4) 0.7091(3) 0.0621(18) Uani 1 1 d . . . H35A H 1.2555 0.3092 0.6884 0.075 Uiso 1 1 calc R . . C36 C 1.1550(6) 0.4086(6) 0.6349(3) 0.111(3) Uani 1 1 d . . . H36A H 1.0922 0.4069 0.6178 0.134 Uiso 1 1 calc R . . H36B H 1.1961 0.3701 0.6160 0.134 Uiso 1 1 calc R . . C37 C 1.1956(7) 0.4920(6) 0.6286(5) 0.139(5) Uani 1 1 d . . . H37A H 1.2040 0.5029 0.5901 0.166 Uiso 1 1 calc R . . H37B H 1.2588 0.4930 0.6454 0.166 Uiso 1 1 calc R . . C38 C 1.1362(7) 0.5594(5) 0.6530(3) 0.123(4) Uani 1 1 d . . . H38A H 1.1495 0.6097 0.6335 0.148 Uiso 1 1 calc R . . H38B H 1.1554 0.5672 0.6906 0.148 Uiso 1 1 calc R . . C39 C 1.0274(5) 0.5424(4) 0.6509(3) 0.082(2) Uani 1 1 d . . . H39A H 0.9926 0.5932 0.6465 0.098 Uiso 1 1 calc R . . H39B H 1.0127 0.5076 0.6200 0.098 Uiso 1 1 calc R . . C40 C 0.9252(4) 0.5357(4) 0.7275(3) 0.0474(15) Uani 1 1 d . . . H40A H 0.8932 0.5805 0.7130 0.057 Uiso 1 1 calc R . . C41 C 0.8980(5) 0.5020(3) 0.7773(3) 0.0467(17) Uani 1 1 d . . . C42 C 0.8266(4) 0.5208(4) 0.8145(3) 0.0508(17) Uani 1 1 d . . . H42A H 0.7820 0.5629 0.8121 0.061 Uiso 1 1 calc R . . C43 C 0.8350(4) 0.4650(4) 0.8555(2) 0.0508(16) Uani 1 1 d . . . H43A H 0.7971 0.4625 0.8867 0.061 Uiso 1 1 calc R . . C44 C 0.9110(3) 0.4120(3) 0.8424(2) 0.0397(13) Uani 1 1 d . . . C45 C 1.0833(4) 0.8087(3) -0.1333(2) 0.0412(13) Uani 1 1 d . . . C46 C 1.1271(4) 0.8190(4) -0.1849(2) 0.0481(15) Uani 1 1 d . . . H46A H 1.1621 0.8660 -0.1925 0.058 Uiso 1 1 calc R . . C47 C 1.1176(4) 0.7600(4) -0.2230(2) 0.0575(16) Uani 1 1 d . . . H47A H 1.1471 0.7664 -0.2567 0.069 Uiso 1 1 calc R . . C48 C 1.0637(5) 0.6889(4) -0.2123(3) 0.0657(19) Uani 1 1 d . . . H48A H 1.0569 0.6492 -0.2391 0.079 Uiso 1 1 calc R . . C49 C 1.0219(5) 0.6787(4) -0.1631(3) 0.0671(19) Uani 1 1 d . . . H49A H 0.9872 0.6313 -0.1564 0.081 Uiso 1 1 calc R . . C50 C 1.0297(4) 0.7380(3) -0.1216(3) 0.0483(15) Uani 1 1 d . . . C51 C 0.9913(3) 0.7861(3) -0.0361(2) 0.0350(13) Uani 1 1 d . . . C52 C 1.0533(4) 0.8563(3) -0.0458(2) 0.0344(12) Uani 1 1 d . . . C53 C 1.0813(3) 0.9208(3) -0.0083(2) 0.0351(12) Uani 1 1 d . . . C54 C 1.1593(4) 0.9731(3) -0.0198(3) 0.0463(15) Uani 1 1 d . . . H54A H 1.1958 0.9732 -0.0515 0.056 Uiso 1 1 calc R . . C55 C 1.1721(4) 1.0238(3) 0.0241(3) 0.0497(16) Uani 1 1 d . . . H55A H 1.2177 1.0649 0.0275 0.060 Uiso 1 1 calc R . . C56 C 1.1032(4) 1.0014(3) 0.0624(3) 0.0385(16) Uani 1 1 d . . . C57 C 1.0790(4) 1.0274(3) 0.1150(2) 0.0440(15) Uani 1 1 d . . . H57A H 1.1137 1.0677 0.1329 0.053 Uiso 1 1 calc R . . C58 C 0.9851(5) 1.0090(4) 0.1953(3) 0.0599(19) Uani 1 1 d . . . H58A H 1.0402 1.0357 0.2117 0.072 Uiso 1 1 calc R . . H58B H 0.9748 0.9578 0.2143 0.072 Uiso 1 1 calc R . . C59 C 0.8984(4) 1.0620(4) 0.2021(3) 0.069(2) Uani 1 1 d . . . H59A H 0.9125 1.1157 0.1875 0.083 Uiso 1 1 calc R . . H59B H 0.8852 1.0683 0.2407 0.083 Uiso 1 1 calc R . . C60 C 0.8087(5) 1.0286(4) 0.1740(3) 0.076(2) Uani 1 1 d . . . H60A H 0.7526 1.0568 0.1880 0.091 Uiso 1 1 calc R . . H60B H 0.8129 1.0396 0.1353 0.091 Uiso 1 1 calc R . . C61 C 0.7961(5) 0.9377(4) 0.1827(3) 0.071(2) Uani 1 1 d . . . H61A H 0.8217 0.9231 0.2182 0.086 Uiso 1 1 calc R . . H61B H 0.7280 0.9249 0.1827 0.086 Uiso 1 1 calc R . . C62 C 0.8070(4) 0.8174(4) 0.1299(2) 0.0442(14) Uani 1 1 d . . . H62A H 0.7581 0.7957 0.1513 0.053 Uiso 1 1 calc R . . C63 C 0.8433(3) 0.7750(3) 0.0850(2) 0.0403(13) Uani 1 1 d . . . C64 C 0.8227(4) 0.6992(3) 0.0613(2) 0.0413(14) Uani 1 1 d . . . H64A H 0.7802 0.6599 0.0742 0.050 Uiso 1 1 calc R . . C65 C 0.8781(4) 0.6950(3) 0.0154(2) 0.0387(14) Uani 1 1 d . . . H65A H 0.8804 0.6514 -0.0089 0.046 Uiso 1 1 calc R . . C66 C 0.9316(3) 0.7685(3) 0.0110(2) 0.0329(12) Uani 1 1 d . . . N1 N 1.0082(3) 0.7894(3) 0.2381(2) 0.0503(13) Uani 1 1 d . . . N2 N 0.8734(3) 0.6682(3) 0.25561(19) 0.0444(12) Uani 1 1 d . . . N3 N 1.0818(3) 0.6929(2) 0.11218(17) 0.0348(11) Uani 1 1 d . . . N4 N 1.1400(3) 0.6205(3) 0.0250(2) 0.0497(13) Uani 1 1 d . . . N5 N 0.9830(4) 0.5124(3) 0.0340(2) 0.0503(14) Uani 1 1 d . . . N6 N 0.9451(3) 0.5711(2) 0.12825(17) 0.0356(10) Uani 1 1 d . . . N7 N 1.0288(4) 0.2313(3) 0.9115(2) 0.0701(16) Uani 1 1 d . . . N8 N 0.8716(3) 0.3325(3) 0.91695(19) 0.0464(11) Uani 1 1 d . . . N9 N 1.1028(3) 0.3268(3) 0.7848(2) 0.0461(12) Uani 1 1 d . . . N10 N 1.1459(4) 0.3840(3) 0.6910(2) 0.0644(15) Uani 1 1 d . . . N11 N 0.9973(4) 0.5020(3) 0.7018(2) 0.0558(16) Uani 1 1 d . . . N12 N 0.9500(3) 0.4352(2) 0.79344(17) 0.0388(10) Uani 1 1 d . . . N13 N 1.0946(3) 0.8663(2) -0.09452(17) 0.0388(10) Uani 1 1 d . . . N14 N 0.9841(3) 0.7290(3) -0.0743(2) 0.0467(11) Uani 1 1 d . . . N15 N 1.0463(3) 0.9388(2) 0.04289(17) 0.0376(10) Uani 1 1 d . . . N16 N 1.0058(4) 0.9922(3) 0.1371(2) 0.0433(13) Uani 1 1 d . . . N17 N 0.8443(3) 0.8879(3) 0.14064(18) 0.0483(12) Uani 1 1 d . . . N18 N 0.9098(3) 0.8172(2) 0.05456(17) 0.0352(11) Uani 1 1 d . . . Ni1 Ni 1.03708(4) 0.59971(4) 0.07533(3) 0.03954(18) Uani 1 1 d . . . Ni2 Ni 1.04675(5) 0.41021(4) 0.74257(3) 0.0452(2) Uani 1 1 d . . . Ni3 Ni 0.95073(4) 0.91022(4) 0.09247(3) 0.03778(18) 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 0.050(4) 0.060(4) 0.045(4) -0.011(3) 0.006(3) -0.003(3) C2 0.086(5) 0.084(5) 0.074(5) -0.034(4) 0.023(5) -0.040(4) C3 0.088(6) 0.112(6) 0.068(5) -0.038(5) 0.016(5) -0.020(5) C4 0.071(5) 0.077(5) 0.055(4) -0.004(4) 0.010(4) -0.001(4) C5 0.053(4) 0.052(4) 0.069(5) 0.000(4) 0.019(4) 0.001(3) C6 0.040(3) 0.045(3) 0.040(4) 0.001(3) 0.004(3) 0.000(3) C7 0.036(3) 0.033(3) 0.045(4) 0.011(3) -0.005(3) 0.002(2) C8 0.033(3) 0.042(3) 0.038(3) 0.004(3) -0.010(3) -0.003(2) C9 0.034(3) 0.031(3) 0.040(3) 0.009(3) -0.003(3) 0.000(2) C10 0.039(3) 0.031(3) 0.054(4) 0.001(3) -0.002(3) -0.007(3) C11 0.037(3) 0.044(3) 0.063(4) 0.018(3) 0.009(3) -0.010(3) C12 0.037(3) 0.039(3) 0.037(3) 0.004(3) 0.010(3) -0.007(2) C13 0.048(4) 0.052(4) 0.056(4) 0.009(3) 0.014(3) -0.009(3) C14 0.090(5) 0.077(5) 0.086(5) -0.026(5) 0.039(5) -0.027(5) C15 0.069(5) 0.098(6) 0.084(6) -0.033(5) 0.010(5) 0.004(5) C16 0.097(6) 0.086(5) 0.096(6) -0.030(5) 0.004(5) -0.008(5) C17 0.071(5) 0.092(6) 0.071(6) -0.034(4) -0.007(5) -0.007(4) C18 0.049(4) 0.043(3) 0.058(5) -0.010(3) -0.006(3) -0.011(3) C19 0.037(4) 0.036(4) 0.057(5) 0.000(3) -0.009(4) -0.007(3) C20 0.045(4) 0.038(3) 0.070(5) 0.005(4) 0.000(4) -0.015(3) C21 0.044(4) 0.046(4) 0.058(4) 0.001(3) 0.005(3) -0.012(3) C22 0.031(3) 0.034(3) 0.041(3) 0.012(3) -0.004(2) 0.002(2) C23 0.076(5) 0.061(4) 0.065(5) 0.011(4) 0.008(4) 0.020(4) C24 0.110(7) 0.136(8) 0.142(9) 0.088(7) 0.045(6) 0.060(6) C25 0.119(7) 0.110(7) 0.116(8) 0.057(6) 0.028(6) 0.032(6) C26 0.102(6) 0.075(5) 0.078(6) 0.016(5) 0.026(5) 0.015(5) C27 0.076(5) 0.062(4) 0.058(4) 0.000(4) 0.013(4) 0.006(4) C28 0.061(4) 0.041(3) 0.055(4) -0.013(3) 0.001(3) -0.004(3) C29 0.034(3) 0.040(3) 0.038(3) -0.012(3) -0.007(3) 0.003(2) C30 0.046(4) 0.040(3) 0.049(4) -0.009(3) -0.005(3) 0.003(3) C31 0.038(3) 0.038(3) 0.058(4) -0.012(3) -0.004(3) 0.004(3) C32 0.048(4) 0.051(4) 0.085(5) -0.005(4) 0.004(4) 0.008(3) C33 0.044(4) 0.054(4) 0.109(6) -0.013(4) 0.005(4) 0.015(3) C34 0.039(3) 0.054(4) 0.071(5) -0.017(4) 0.008(3) 0.005(3) C35 0.041(4) 0.072(4) 0.073(5) -0.021(4) 0.006(4) 0.006(3) C36 0.084(6) 0.172(9) 0.078(6) -0.007(7) 0.027(5) 0.038(7) C37 0.080(7) 0.197(12) 0.138(10) 0.022(9) 0.037(7) -0.041(7) C38 0.156(9) 0.107(7) 0.106(7) -0.047(6) 0.087(7) -0.077(6) C39 0.097(6) 0.079(5) 0.070(5) 0.018(4) 0.042(5) 0.010(5) C40 0.045(4) 0.046(4) 0.050(4) -0.002(3) -0.012(3) 0.001(3) C41 0.050(4) 0.047(4) 0.042(4) -0.004(3) -0.001(4) 0.004(3) C42 0.042(4) 0.051(4) 0.059(5) -0.006(4) -0.002(3) 0.021(3) C43 0.044(4) 0.061(4) 0.048(4) 0.002(3) 0.001(3) 0.014(3) C44 0.031(3) 0.038(3) 0.050(3) -0.009(3) 0.000(3) 0.004(3) C45 0.038(3) 0.044(3) 0.042(3) 0.000(3) -0.005(3) 0.006(3) C46 0.047(4) 0.054(4) 0.043(4) -0.005(3) -0.003(3) 0.009(3) C47 0.057(4) 0.080(5) 0.036(4) 0.008(4) 0.002(3) 0.005(4) C48 0.070(4) 0.081(5) 0.046(4) -0.021(4) -0.004(4) -0.006(4) C49 0.081(5) 0.065(4) 0.056(4) -0.017(4) 0.014(4) -0.027(4) C50 0.052(4) 0.046(3) 0.047(4) -0.007(3) -0.003(3) -0.007(3) C51 0.032(3) 0.035(3) 0.039(3) 0.001(3) -0.004(3) 0.000(2) C52 0.030(3) 0.036(3) 0.038(3) 0.001(2) -0.004(3) -0.002(2) C53 0.032(3) 0.031(3) 0.042(3) 0.000(3) -0.007(2) -0.004(2) C54 0.048(4) 0.039(3) 0.052(4) 0.003(3) 0.008(3) -0.006(3) C55 0.042(4) 0.044(3) 0.063(4) -0.006(3) -0.001(3) -0.011(3) C56 0.036(3) 0.037(3) 0.042(4) -0.006(2) -0.006(3) -0.002(2) C57 0.042(4) 0.036(3) 0.054(4) -0.011(3) -0.011(3) -0.005(3) C58 0.064(5) 0.064(4) 0.051(5) -0.027(3) -0.007(4) -0.005(3) C59 0.077(5) 0.067(4) 0.062(4) -0.029(4) 0.018(4) -0.006(4) C60 0.059(4) 0.073(5) 0.096(6) -0.030(5) 0.007(4) 0.008(4) C61 0.059(4) 0.090(5) 0.065(5) -0.034(4) 0.015(4) -0.015(4) C62 0.036(3) 0.057(4) 0.040(4) 0.005(3) -0.001(3) -0.007(3) C63 0.029(3) 0.045(3) 0.047(4) 0.004(3) -0.006(3) -0.008(2) C64 0.030(3) 0.033(3) 0.061(4) 0.008(3) -0.003(3) -0.007(2) C65 0.034(3) 0.032(3) 0.050(4) 0.003(3) -0.002(3) 0.000(3) C66 0.027(3) 0.035(3) 0.037(3) 0.002(3) -0.007(2) -0.002(2) N1 0.051(3) 0.050(3) 0.050(3) -0.004(3) 0.001(3) -0.016(2) N2 0.042(3) 0.042(3) 0.049(3) 0.002(2) 0.008(2) 0.002(2) N3 0.031(2) 0.037(2) 0.036(3) 0.006(2) -0.001(2) -0.0043(19) N4 0.049(3) 0.053(3) 0.047(3) -0.003(3) 0.003(2) -0.010(3) N5 0.051(3) 0.056(3) 0.044(3) -0.013(3) 0.000(3) -0.005(3) N6 0.032(2) 0.032(2) 0.042(3) 0.007(2) -0.006(2) -0.006(2) N7 0.062(3) 0.071(3) 0.077(4) 0.018(3) 0.012(3) 0.026(3) N8 0.045(3) 0.046(3) 0.048(3) -0.003(3) 0.003(3) 0.005(2) N9 0.037(3) 0.043(3) 0.058(3) -0.015(3) -0.001(2) -0.001(2) N10 0.062(3) 0.087(4) 0.044(3) -0.016(3) 0.013(3) 0.005(3) N11 0.062(4) 0.056(3) 0.049(4) -0.005(3) 0.003(3) -0.004(2) N12 0.035(2) 0.040(2) 0.041(3) -0.008(2) -0.003(2) -0.001(2) N13 0.038(2) 0.037(2) 0.042(3) 0.003(2) -0.002(2) 0.000(2) N14 0.054(3) 0.045(3) 0.041(3) -0.007(3) 0.006(3) -0.012(2) N15 0.041(2) 0.030(2) 0.042(3) -0.001(2) -0.009(2) -0.002(2) N16 0.042(3) 0.045(3) 0.043(3) -0.009(2) -0.005(3) 0.001(2) N17 0.042(3) 0.055(3) 0.048(3) -0.014(3) 0.005(2) -0.007(2) N18 0.030(2) 0.039(2) 0.037(3) 0.003(2) -0.003(2) -0.002(2) Ni1 0.0389(4) 0.0417(4) 0.0380(4) 0.0009(4) -0.0014(4) -0.0067(3) Ni2 0.0390(4) 0.0508(4) 0.0458(4) -0.0126(4) 0.0018(3) 0.0029(4) Ni3 0.0362(4) 0.0383(4) 0.0388(4) -0.0051(3) -0.0013(3) -0.0053(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 C1 N1 1.363(7) . ? C1 C6 1.404(7) . ? C1 C2 1.411(8) . ? C2 C3 1.358(8) . ? C3 C4 1.385(9) . ? C4 C5 1.359(8) . ? C5 C6 1.409(7) . ? C6 N2 1.339(6) . ? C7 N2 1.341(6) . ? C7 C8 1.448(7) . ? C7 C22 1.467(7) . ? C8 N1 1.335(7) . ? C8 C9 1.462(7) . ? C9 N3 1.361(6) . ? C9 C10 1.411(6) . ? C10 C11 1.359(7) . ? C11 C12 1.376(7) . ? C12 N3 1.380(6) . ? C12 C13 1.387(7) . ? C13 N4 1.293(7) . ? C14 C15 1.470(9) . ? C14 N4 1.493(7) . ? C15 C16 1.513(9) . ? C16 C17 1.485(9) . ? C17 N5 1.489(9) . ? C18 N5 1.285(7) . ? C18 C19 1.403(8) . ? C19 N6 1.380(6) . ? C19 C20 1.384(8) . ? C20 C21 1.374(8) . ? C21 C22 1.429(7) . ? C22 N6 1.364(6) . ? C23 N7 1.336(8) . ? C23 C28 1.396(8) . ? C23 C24 1.406(9) . ? C24 C25 1.344(10) . ? C25 C26 1.382(10) . ? C26 C27 1.363(9) . ? C27 C28 1.416(8) . ? C28 N8 1.343(7) . ? C29 N8 1.332(6) . ? C29 C30 1.449(7) . ? C29 C44 1.452(7) . ? C30 N7 1.326(7) . ? C30 C31 1.464(8) . ? C31 N9 1.370(7) . ? C31 C32 1.419(7) . ? C32 C33 1.365(8) . ? C33 C34 1.375(8) . ? C34 N9 1.378(7) . ? C34 C35 1.387(8) . ? C35 N10 1.303(7) . ? C36 N10 1.441(8) . ? C36 C37 1.487(11) . ? C37 C38 1.504(11) . ? C38 C39 1.541(10) . ? C39 N11 1.474(8) . ? C40 N11 1.307(7) . ? C40 C41 1.394(8) . ? C41 N12 1.372(6) . ? C41 C42 1.383(8) . ? C42 C43 1.365(8) . ? C43 C44 1.406(7) . ? C44 N12 1.372(6) . ? C45 N13 1.350(6) . ? C45 C50 1.408(7) . ? C45 C46 1.415(7) . ? C46 C47 1.352(8) . ? C47 C48 1.411(8) . ? C48 C49 1.349(8) . ? C49 C50 1.413(7) . ? C50 N14 1.332(7) . ? C51 N14 1.329(7) . ? C51 C66 1.451(7) . ? C51 C52 1.458(7) . ? C52 N13 1.336(6) . ? C52 C53 1.454(6) . ? C53 N15 1.380(6) . ? C53 C54 1.412(7) . ? C54 C55 1.370(8) . ? C55 C56 1.392(8) . ? C56 N15 1.383(6) . ? C56 C57 1.399(8) . ? C57 N16 1.291(7) . ? C58 N16 1.484(7) . ? C58 C59 1.496(8) . ? C59 C60 1.528(8) . ? C60 C61 1.516(9) . ? C61 N17 1.477(7) . ? C62 N17 1.295(6) . ? C62 C63 1.397(7) . ? C63 N18 1.376(6) . ? C63 C64 1.402(7) . ? C64 C65 1.367(7) . ? C65 C66 1.421(6) . ? C66 N18 1.368(6) . ? N3 Ni1 1.881(4) . ? N4 Ni1 1.922(5) . ? N5 Ni1 1.909(5) . ? N6 Ni1 1.883(4) . ? N9 Ni2 1.884(5) . ? N10 Ni2 1.920(5) . ? N11 Ni2 1.934(5) . ? N12 Ni2 1.881(4) . ? N15 Ni3 1.862(4) . ? N16 Ni3 1.895(4) . ? N17 Ni3 1.929(4) . ? N18 Ni3 1.875(4) . ? 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 N1 C1 C6 119.9(5) . . ? N1 C1 C2 119.9(6) . . ? C6 C1 C2 120.2(5) . . ? C3 C2 C1 119.1(6) . . ? C2 C3 C4 120.7(7) . . ? C5 C4 C3 121.9(6) . . ? C4 C5 C6 119.1(6) . . ? N2 C6 C1 120.6(5) . . ? N2 C6 C5 120.4(5) . . ? C1 C6 C5 119.0(5) . . ? N2 C7 C8 119.8(5) . . ? N2 C7 C22 111.6(4) . . ? C8 C7 C22 128.6(5) . . ? N1 C8 C7 119.2(5) . . ? N1 C8 C9 110.7(5) . . ? C7 C8 C9 130.1(5) . . ? N3 C9 C10 108.6(5) . . ? N3 C9 C8 129.1(5) . . ? C10 C9 C8 122.3(5) . . ? C11 C10 C9 108.1(5) . . ? C10 C11 C12 106.5(5) . . ? C11 C12 N3 110.8(5) . . ? C11 C12 C13 134.5(5) . . ? N3 C12 C13 114.7(5) . . ? N4 C13 C12 118.2(5) . . ? C15 C14 N4 112.4(6) . . ? C14 C15 C16 114.6(7) . . ? C17 C16 C15 113.1(6) . . ? C16 C17 N5 110.7(7) . . ? N5 C18 C19 116.6(6) . . ? N6 C19 C20 110.6(6) . . ? N6 C19 C18 114.7(6) . . ? C20 C19 C18 134.4(6) . . ? C21 C20 C19 107.3(5) . . ? C20 C21 C22 106.6(5) . . ? N6 C22 C21 109.3(5) . . ? N6 C22 C7 130.0(5) . . ? C21 C22 C7 120.6(5) . . ? N7 C23 C28 120.9(6) . . ? N7 C23 C24 121.0(7) . . ? C28 C23 C24 118.0(7) . . ? C25 C24 C23 121.0(8) . . ? C24 C25 C26 122.2(8) . . ? C27 C26 C25 118.2(8) . . ? C26 C27 C28 121.4(7) . . ? N8 C28 C23 119.7(6) . . ? N8 C28 C27 121.2(6) . . ? C23 C28 C27 119.1(6) . . ? N8 C29 C30 118.6(5) . . ? N8 C29 C44 112.1(4) . . ? C30 C29 C44 129.1(5) . . ? N7 C30 C29 119.9(5) . . ? N7 C30 C31 111.3(5) . . ? C29 C30 C31 128.8(5) . . ? N9 C31 C32 108.6(5) . . ? N9 C31 C30 130.2(5) . . ? C32 C31 C30 121.2(6) . . ? C33 C32 C31 107.4(6) . . ? C32 C33 C34 107.1(6) . . ? C33 C34 N9 110.8(6) . . ? C33 C34 C35 134.3(6) . . ? N9 C34 C35 114.8(6) . . ? N10 C35 C34 116.7(6) . . ? N10 C36 C37 112.9(8) . . ? C36 C37 C38 115.2(7) . . ? C37 C38 C39 113.2(7) . . ? N11 C39 C38 109.4(7) . . ? N11 C40 C41 117.7(6) . . ? N12 C41 C42 111.5(6) . . ? N12 C41 C40 115.2(6) . . ? C42 C41 C40 133.3(6) . . ? C43 C42 C41 106.0(5) . . ? C42 C43 C44 108.0(5) . . ? N12 C44 C43 109.1(5) . . ? N12 C44 C29 129.3(5) . . ? C43 C44 C29 121.5(5) . . ? N13 C45 C50 119.6(5) . . ? N13 C45 C46 119.7(5) . . ? C50 C45 C46 120.6(5) . . ? C47 C46 C45 119.4(6) . . ? C46 C47 C48 120.9(6) . . ? C49 C48 C47 119.9(6) . . ? C48 C49 C50 121.7(6) . . ? N14 C50 C45 121.4(5) . . ? N14 C50 C49 121.1(5) . . ? C45 C50 C49 117.4(5) . . ? N14 C51 C66 112.2(4) . . ? N14 C51 C52 119.0(5) . . ? C66 C51 C52 128.8(5) . . ? N13 C52 C53 111.2(4) . . ? N13 C52 C51 119.9(5) . . ? C53 C52 C51 128.9(5) . . ? N15 C53 C54 108.8(5) . . ? N15 C53 C52 129.5(4) . . ? C54 C53 C52 121.5(5) . . ? C55 C54 C53 108.2(5) . . ? C54 C55 C56 106.4(5) . . ? N15 C56 C55 110.8(5) . . ? N15 C56 C57 114.1(5) . . ? C55 C56 C57 135.1(5) . . ? N16 C57 C56 116.2(5) . . ? N16 C58 C59 111.8(6) . . ? C58 C59 C60 113.6(5) . . ? C61 C60 C59 112.6(6) . . ? N17 C61 C60 113.1(5) . . ? N17 C62 C63 117.3(5) . . ? N18 C63 C62 115.0(5) . . ? N18 C63 C64 110.9(5) . . ? C62 C63 C64 134.0(5) . . ? C65 C64 C63 105.8(5) . . ? C64 C65 C66 108.4(5) . . ? N18 C66 C65 108.6(4) . . ? N18 C66 C51 129.3(4) . . ? C65 C66 C51 121.9(5) . . ? C8 N1 C1 120.3(5) . . ? C6 N2 C7 120.2(5) . . ? C9 N3 C12 106.0(4) . . ? C9 N3 Ni1 143.1(3) . . ? C12 N3 Ni1 110.4(3) . . ? C13 N4 C14 116.1(5) . . ? C13 N4 Ni1 110.8(4) . . ? C14 N4 Ni1 133.0(4) . . ? C18 N5 C17 118.7(5) . . ? C18 N5 Ni1 112.8(4) . . ? C17 N5 Ni1 127.1(4) . . ? C22 N6 C19 106.2(5) . . ? C22 N6 Ni1 143.0(4) . . ? C19 N6 Ni1 110.8(4) . . ? C30 N7 C23 120.0(5) . . ? C29 N8 C28 120.8(5) . . ? C31 N9 C34 106.0(5) . . ? C31 N9 Ni2 142.6(4) . . ? C34 N9 Ni2 111.3(4) . . ? C35 N10 C36 117.9(6) . . ? C35 N10 Ni2 112.3(5) . . ? C36 N10 Ni2 129.1(5) . . ? C40 N11 C39 115.9(6) . . ? C40 N11 Ni2 110.6(4) . . ? C39 N11 Ni2 133.4(5) . . ? C44 N12 C41 105.4(5) . . ? C44 N12 Ni2 143.5(4) . . ? C41 N12 Ni2 111.1(4) . . ? C52 N13 C45 119.6(4) . . ? C51 N14 C50 120.1(5) . . ? C53 N15 C56 105.8(4) . . ? C53 N15 Ni3 142.5(3) . . ? C56 N15 Ni3 111.7(4) . . ? C57 N16 C58 118.4(5) . . ? C57 N16 Ni3 113.1(4) . . ? C58 N16 Ni3 127.6(4) . . ? C62 N17 C61 116.9(5) . . ? C62 N17 Ni3 110.7(4) . . ? C61 N17 Ni3 132.3(4) . . ? C66 N18 C63 106.3(4) . . ? C66 N18 Ni3 142.6(3) . . ? C63 N18 Ni3 110.1(3) . . ? N3 Ni1 N6 95.51(18) . . ? N3 Ni1 N5 174.1(2) . . ? N6 Ni1 N5 84.9(2) . . ? N3 Ni1 N4 85.30(19) . . ? N6 Ni1 N4 173.81(19) . . ? N5 Ni1 N4 94.9(2) . . ? N12 Ni2 N9 95.11(19) . . ? N12 Ni2 N10 179.5(2) . . ? N9 Ni2 N10 84.4(2) . . ? N12 Ni2 N11 85.4(2) . . ? N9 Ni2 N11 175.1(2) . . ? N10 Ni2 N11 95.1(2) . . ? N15 Ni3 N18 95.56(17) . . ? N15 Ni3 N16 84.9(2) . . ? N18 Ni3 N16 170.44(19) . . ? N15 Ni3 N17 174.77(18) . . ? N18 Ni3 N17 85.24(18) . . ? N16 Ni3 N17 95.2(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.239 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.054 data_p21c _database_code_depnum_ccdc_archive 'CCDC 254150' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H34 Cl2 N12 Ni2' _chemical_formula_weight 907.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.3090(18) _cell_length_b 26.440(3) _cell_length_c 9.1440(10) _cell_angle_alpha 90.00 _cell_angle_beta 104.061(2) _cell_angle_gamma 90.00 _cell_volume 3824.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1864 _exptl_absorpt_coefficient_mu 1.176 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7192 _exptl_absorpt_correction_T_max 0.8914 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Smart CCD' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19083 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 25.01 _reflns_number_total 6734 _reflns_number_gt 4357 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0905P)^2^+2.5713P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0033(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6734 _refine_ls_number_parameters 533 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0961 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1733 _refine_ls_wR_factor_gt 0.1504 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 Ni1 Ni 0.46060(4) 0.51556(2) 0.79300(7) 0.0454(2) Uani 1 1 d . . . N1 N 0.4399(3) 0.33944(17) 0.5770(5) 0.0538(11) Uani 1 1 d . . . N2 N 0.4114(2) 0.45105(16) 0.7880(4) 0.0478(10) Uani 1 1 d . . . N3 N 0.3816(3) 0.53522(17) 0.9023(5) 0.0528(11) Uani 1 1 d . . . N4 N 0.5072(3) 0.58105(16) 0.7989(5) 0.0514(11) Uani 1 1 d . . . N5 N 0.5453(2) 0.49664(15) 0.6957(4) 0.0441(10) Uani 1 1 d . . . N6 N 0.5962(3) 0.37467(16) 0.5561(5) 0.0511(10) Uani 1 1 d . . . C1 C 0.4898(4) 0.3114(2) 0.5097(5) 0.0550(14) Uani 1 1 d . . . C2 C 0.5712(3) 0.3280(2) 0.5084(6) 0.0517(13) Uani 1 1 d . . . C3 C 0.6242(4) 0.2960(2) 0.4480(6) 0.0651(15) Uani 1 1 d . . . H3A H 0.6790 0.3060 0.4492 0.078 Uiso 1 1 calc R . . C4 C 0.5947(5) 0.2506(2) 0.3885(7) 0.0755(18) Uani 1 1 d . . . H4A H 0.6296 0.2296 0.3487 0.091 Uiso 1 1 calc R . . C5 C 0.5128(5) 0.2350(2) 0.3863(7) 0.081(2) Uani 1 1 d . . . H5A H 0.4937 0.2039 0.3432 0.097 Uiso 1 1 calc R . . C6 C 0.4600(4) 0.2639(2) 0.4454(7) 0.0735(18) Uani 1 1 d . . . H6B H 0.4056 0.2530 0.4437 0.088 Uiso 1 1 calc R . . C7 C 0.4669(3) 0.38416(19) 0.6345(5) 0.0462(12) Uani 1 1 d . . . C8 C 0.5458(3) 0.40522(19) 0.6130(5) 0.0429(11) Uani 1 1 d . . . C9 C 0.4121(3) 0.40415(19) 0.7268(5) 0.0454(12) Uani 1 1 d . . . C10 C 0.3506(3) 0.3742(2) 0.7700(6) 0.0556(13) Uani 1 1 d . . . H10A H 0.3380 0.3407 0.7428 0.067 Uiso 1 1 calc R . . C11 C 0.3126(3) 0.4031(2) 0.8594(6) 0.0596(14) Uani 1 1 d . . . H11A H 0.2701 0.3929 0.9050 0.072 Uiso 1 1 calc R . . C12 C 0.3499(3) 0.4506(2) 0.8685(6) 0.0531(13) Uani 1 1 d . . . C13 C 0.3365(3) 0.4978(2) 0.9304(6) 0.0579(14) Uani 1 1 d . . . H13A H 0.2974 0.5019 0.9884 0.070 Uiso 1 1 calc R . . C14 C 0.3684(4) 0.5851(2) 0.9625(7) 0.0690(16) Uani 1 1 d . . . H14A H 0.4044 0.5886 1.0633 0.083 Uiso 1 1 calc R . . H14B H 0.3101 0.5881 0.9690 0.083 Uiso 1 1 calc R . . C15 C 0.3883(4) 0.6265(2) 0.8626(7) 0.0677(16) Uani 1 1 d . . . H15A H 0.3558 0.6211 0.7599 0.081 Uiso 1 1 calc R . . H15B H 0.3720 0.6589 0.8964 0.081 Uiso 1 1 calc R . . C16 C 0.4804(4) 0.6274(2) 0.8657(6) 0.0619(15) Uani 1 1 d . . . H16A H 0.4922 0.6567 0.8103 0.074 Uiso 1 1 calc R . . H16B H 0.5130 0.6306 0.9692 0.074 Uiso 1 1 calc R . . C17 C 0.5733(3) 0.5828(2) 0.7432(6) 0.0533(13) Uani 1 1 d . . . H17A H 0.6035 0.6126 0.7418 0.064 Uiso 1 1 calc R . . C18 C 0.5962(3) 0.53755(19) 0.6855(5) 0.0476(12) Uani 1 1 d . . . C19 C 0.6609(3) 0.5228(2) 0.6193(6) 0.0561(14) Uani 1 1 d . . . H19A H 0.7033 0.5433 0.5994 0.067 Uiso 1 1 calc R . . C20 C 0.6500(3) 0.4726(2) 0.5898(6) 0.0550(14) Uani 1 1 d . . . H20A H 0.6843 0.4524 0.5463 0.066 Uiso 1 1 calc R . . C21 C 0.5781(3) 0.45621(19) 0.6360(5) 0.0429(11) Uani 1 1 d . . . Ni2 Ni 0.03567(4) 0.50358(2) 0.31766(7) 0.0463(2) Uani 1 1 d . . . N7 N -0.0147(3) 0.32676(16) 0.0995(5) 0.0552(11) Uani 1 1 d . . . N8 N 0.0618(2) 0.43453(16) 0.3414(4) 0.0467(10) Uani 1 1 d . . . N9 N 0.1233(3) 0.51210(17) 0.4948(5) 0.0539(11) Uani 1 1 d . . . N10 N 0.0141(3) 0.57348(16) 0.2949(5) 0.0522(11) Uani 1 1 d . . . N11 N -0.0525(2) 0.49651(15) 0.1431(5) 0.0446(10) Uani 1 1 d . . . N12 N -0.1480(2) 0.38423(16) -0.0578(5) 0.0516(11) Uani 1 1 d . . . C22 C -0.0733(3) 0.3060(2) -0.0134(6) 0.0552(13) Uani 1 1 d . . . C23 C -0.1447(3) 0.3348(2) -0.0877(6) 0.0550(13) Uani 1 1 d . . . C24 C -0.2081(4) 0.3114(2) -0.2007(7) 0.0714(17) Uani 1 1 d . . . H24A H -0.2558 0.3296 -0.2493 0.086 Uiso 1 1 calc R . . C25 C -0.1991(5) 0.2619(3) -0.2384(7) 0.080(2) Uani 1 1 d . . . H25A H -0.2408 0.2467 -0.3130 0.097 Uiso 1 1 calc R . . C26 C -0.1274(5) 0.2337(2) -0.1657(8) 0.0786(18) Uani 1 1 d . . . H26A H -0.1218 0.2003 -0.1939 0.094 Uiso 1 1 calc R . . C27 C -0.0665(4) 0.2549(2) -0.0552(7) 0.0718(17) Uani 1 1 d . . . H27A H -0.0200 0.2358 -0.0065 0.086 Uiso 1 1 calc R . . C28 C -0.0205(3) 0.37525(19) 0.1368(5) 0.0467(12) Uani 1 1 d . . . C29 C -0.0870(3) 0.40650(18) 0.0463(5) 0.0427(11) Uani 1 1 d . . . C30 C 0.0446(3) 0.38857(19) 0.2725(6) 0.0472(12) Uani 1 1 d . . . C31 C 0.0996(4) 0.3524(2) 0.3557(7) 0.0713(17) Uani 1 1 d . . . H31A H 0.1005 0.3181 0.3333 0.086 Uiso 1 1 calc R . . C32 C 0.1520(4) 0.3765(2) 0.4764(7) 0.0730(18) Uani 1 1 d . . . H32A H 0.1948 0.3620 0.5506 0.088 Uiso 1 1 calc R . . C33 C 0.1281(3) 0.4263(2) 0.4649(6) 0.0581(14) Uani 1 1 d . . . C34 C 0.1590(3) 0.4705(2) 0.5456(6) 0.0586(14) Uani 1 1 d . . . H34A H 0.2033 0.4695 0.6316 0.070 Uiso 1 1 calc R . . C35 C 0.1532(4) 0.5597(2) 0.5731(6) 0.0648(16) Uani 1 1 d . . . H35A H 0.2117 0.5558 0.6279 0.078 Uiso 1 1 calc R . . H35B H 0.1202 0.5670 0.6457 0.078 Uiso 1 1 calc R . . C36 C 0.1462(4) 0.6035(2) 0.4656(7) 0.0656(16) Uani 1 1 d . . . H36A H 0.1728 0.6331 0.5200 0.079 Uiso 1 1 calc R . . H36B H 0.1759 0.5954 0.3887 0.079 Uiso 1 1 calc R . . C37 C 0.0554(4) 0.6154(2) 0.3919(7) 0.0651(16) Uani 1 1 d . . . H37A H 0.0251 0.6218 0.4691 0.078 Uiso 1 1 calc R . . H37B H 0.0528 0.6458 0.3316 0.078 Uiso 1 1 calc R . . C38 C -0.0441(3) 0.5838(2) 0.1766(6) 0.0536(13) Uani 1 1 d . . . H38A H -0.0596 0.6171 0.1503 0.064 Uiso 1 1 calc R . . C39 C -0.0837(3) 0.54293(19) 0.0879(6) 0.0492(12) Uani 1 1 d . . . C40 C -0.1453(3) 0.5373(2) -0.0451(6) 0.0535(13) Uani 1 1 d . . . H40A H -0.1752 0.5632 -0.1038 0.064 Uiso 1 1 calc R . . C41 C -0.1538(3) 0.48664(19) -0.0736(6) 0.0497(13) Uani 1 1 d . . . H41A H -0.1907 0.4715 -0.1555 0.060 Uiso 1 1 calc R . . C42 C -0.0961(3) 0.46145(19) 0.0443(5) 0.0442(11) Uani 1 1 d . . . C43 C -0.1853(9) 0.7201(6) -0.0484(15) 0.230(7) Uani 1 1 d . . . H43A H -0.1771 0.7561 -0.0608 0.276 Uiso 1 1 calc R . . H43B H -0.1447 0.7026 -0.0920 0.276 Uiso 1 1 calc R . . Cl1 Cl -0.2775(3) 0.7061(2) -0.1469(6) 0.270(3) Uani 1 1 d . . . Cl2 Cl -0.1597(3) 0.70759(11) 0.1417(4) 0.1820(14) 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 Ni1 0.0455(4) 0.0536(4) 0.0374(4) 0.0042(3) 0.0107(3) 0.0015(3) N1 0.059(3) 0.061(3) 0.042(2) -0.002(2) 0.013(2) -0.009(2) N2 0.040(2) 0.063(3) 0.039(2) 0.008(2) 0.0088(18) -0.0004(19) N3 0.054(3) 0.062(3) 0.045(2) 0.003(2) 0.016(2) 0.004(2) N4 0.054(3) 0.055(3) 0.041(2) 0.002(2) 0.005(2) 0.004(2) N5 0.044(2) 0.049(2) 0.037(2) 0.0058(19) 0.0064(18) -0.0018(19) N6 0.053(3) 0.060(3) 0.041(2) 0.005(2) 0.0117(19) 0.005(2) C1 0.073(4) 0.056(3) 0.035(3) 0.005(2) 0.010(3) -0.002(3) C2 0.064(3) 0.052(3) 0.039(3) 0.004(2) 0.012(2) 0.003(3) C3 0.078(4) 0.065(4) 0.055(4) 0.001(3) 0.023(3) 0.012(3) C4 0.110(6) 0.062(4) 0.061(4) -0.003(3) 0.033(4) 0.012(4) C5 0.123(6) 0.059(4) 0.060(4) -0.008(3) 0.022(4) -0.013(4) C6 0.098(5) 0.072(4) 0.057(4) -0.012(3) 0.029(4) -0.022(4) C7 0.052(3) 0.051(3) 0.034(3) 0.007(2) 0.006(2) -0.001(2) C8 0.039(3) 0.057(3) 0.031(2) 0.004(2) 0.004(2) 0.003(2) C9 0.042(3) 0.051(3) 0.040(3) 0.006(2) 0.003(2) -0.002(2) C10 0.046(3) 0.061(3) 0.057(3) 0.005(3) 0.009(3) -0.005(2) C11 0.047(3) 0.070(4) 0.064(4) 0.014(3) 0.016(3) -0.001(3) C12 0.039(3) 0.074(4) 0.050(3) 0.012(3) 0.017(2) 0.003(3) C13 0.053(3) 0.079(4) 0.045(3) 0.008(3) 0.018(3) 0.014(3) C14 0.077(4) 0.070(4) 0.062(4) -0.002(3) 0.020(3) 0.014(3) C15 0.076(4) 0.058(4) 0.066(4) -0.005(3) 0.013(3) 0.016(3) C16 0.072(4) 0.059(4) 0.051(3) -0.011(3) 0.009(3) 0.007(3) C17 0.052(3) 0.054(3) 0.048(3) 0.007(2) 0.000(3) -0.002(2) C18 0.046(3) 0.052(3) 0.042(3) 0.008(2) 0.005(2) -0.005(2) C19 0.043(3) 0.067(4) 0.059(3) 0.004(3) 0.014(2) -0.007(3) C20 0.043(3) 0.063(4) 0.062(4) 0.009(3) 0.019(3) 0.004(3) C21 0.039(3) 0.055(3) 0.032(2) 0.005(2) 0.004(2) 0.003(2) Ni2 0.0453(4) 0.0532(4) 0.0442(4) 0.0018(3) 0.0179(3) -0.0023(3) N7 0.063(3) 0.049(3) 0.053(3) 0.002(2) 0.012(2) 0.002(2) N8 0.040(2) 0.062(3) 0.039(2) 0.011(2) 0.0124(18) 0.0000(19) N9 0.058(3) 0.063(3) 0.045(3) 0.006(2) 0.020(2) -0.009(2) N10 0.049(2) 0.056(3) 0.058(3) -0.001(2) 0.025(2) -0.003(2) N11 0.042(2) 0.050(3) 0.046(2) 0.0084(19) 0.0209(19) 0.0049(18) N12 0.042(2) 0.059(3) 0.053(3) 0.002(2) 0.011(2) -0.005(2) C22 0.061(3) 0.056(3) 0.052(3) -0.001(3) 0.020(3) -0.002(3) C23 0.060(3) 0.056(4) 0.052(3) -0.001(3) 0.020(3) -0.008(3) C24 0.063(4) 0.071(4) 0.074(4) 0.003(3) 0.006(3) -0.011(3) C25 0.093(5) 0.074(5) 0.071(4) -0.007(4) 0.013(4) -0.030(4) C26 0.105(5) 0.058(4) 0.076(4) -0.008(3) 0.027(4) -0.011(4) C27 0.080(4) 0.060(4) 0.077(4) -0.009(3) 0.021(4) -0.002(3) C28 0.047(3) 0.052(3) 0.045(3) 0.005(2) 0.019(2) -0.002(2) C29 0.037(3) 0.051(3) 0.044(3) 0.002(2) 0.019(2) -0.002(2) C30 0.049(3) 0.049(3) 0.046(3) 0.001(2) 0.015(2) -0.003(2) C31 0.080(4) 0.058(4) 0.066(4) 0.009(3) -0.001(3) 0.017(3) C32 0.071(4) 0.070(4) 0.063(4) 0.014(3) -0.011(3) 0.011(3) C33 0.048(3) 0.072(4) 0.052(3) 0.011(3) 0.008(3) -0.004(3) C34 0.056(3) 0.077(4) 0.042(3) 0.007(3) 0.009(2) -0.010(3) C35 0.060(4) 0.081(4) 0.055(3) -0.010(3) 0.017(3) -0.019(3) C36 0.069(4) 0.066(4) 0.069(4) -0.016(3) 0.031(3) -0.021(3) C37 0.082(4) 0.053(3) 0.066(4) -0.009(3) 0.032(3) -0.008(3) C38 0.057(3) 0.048(3) 0.066(4) 0.008(3) 0.035(3) 0.006(3) C39 0.046(3) 0.050(3) 0.057(3) 0.004(3) 0.025(3) 0.004(2) C40 0.040(3) 0.064(4) 0.061(3) 0.011(3) 0.021(3) 0.010(2) C41 0.039(3) 0.060(3) 0.054(3) -0.001(3) 0.017(2) 0.003(2) C42 0.037(3) 0.057(3) 0.043(3) 0.003(2) 0.017(2) 0.004(2) C43 0.168(12) 0.35(2) 0.155(11) 0.067(13) -0.004(10) -0.068(13) Cl1 0.165(3) 0.319(6) 0.307(6) 0.071(5) 0.020(4) -0.058(4) Cl2 0.236(4) 0.122(2) 0.201(3) -0.004(2) 0.077(3) -0.006(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 Ni1 N2 1.881(4) . ? Ni1 N5 1.883(4) . ? Ni1 N3 1.885(4) . ? Ni1 N4 1.887(4) . ? N1 C7 1.325(6) . ? N1 C1 1.354(7) . ? N2 C9 1.362(6) . ? N2 C12 1.381(6) . ? N3 C13 1.295(7) . ? N3 C14 1.464(7) . ? N4 C17 1.299(7) . ? N4 C16 1.482(6) . ? N5 C21 1.367(6) . ? N5 C18 1.380(6) . ? N6 C2 1.339(6) . ? N6 C8 1.345(6) . ? C1 C2 1.402(7) . ? C1 C6 1.419(8) . ? C2 C3 1.415(7) . ? C3 C4 1.357(8) . ? C4 C5 1.394(9) . ? C5 C6 1.358(9) . ? C7 C8 1.458(7) . ? C7 C9 1.468(7) . ? C8 C21 1.444(7) . ? C9 C10 1.407(7) . ? C10 C11 1.373(7) . ? C11 C12 1.390(7) . ? C12 C13 1.408(8) . ? C14 C15 1.511(8) . ? C15 C16 1.496(8) . ? C17 C18 1.395(7) . ? C18 C19 1.395(7) . ? C19 C20 1.359(7) . ? C20 C21 1.409(7) . ? Ni2 N8 1.875(4) . ? Ni2 N11 1.880(4) . ? Ni2 N10 1.883(4) . ? Ni2 N9 1.895(4) . ? N7 C28 1.336(6) . ? N7 C22 1.343(6) . ? N8 C30 1.366(6) . ? N8 C33 1.378(6) . ? N9 C34 1.278(7) . ? N9 C35 1.472(7) . ? N10 C38 1.284(6) . ? N10 C37 1.475(7) . ? N11 C42 1.367(6) . ? N11 C39 1.377(6) . ? N12 C29 1.335(6) . ? N12 C23 1.340(6) . ? C22 C27 1.415(7) . ? C22 C23 1.418(7) . ? C23 C24 1.414(7) . ? C24 C25 1.370(9) . ? C25 C26 1.410(9) . ? C26 C27 1.354(8) . ? C28 C29 1.451(7) . ? C28 C30 1.468(7) . ? C29 C42 1.460(7) . ? C30 C31 1.402(7) . ? C31 C32 1.378(8) . ? C32 C33 1.369(8) . ? C33 C34 1.409(8) . ? C35 C36 1.504(8) . ? C36 C37 1.503(8) . ? C38 C39 1.411(7) . ? C39 C40 1.384(7) . ? C40 C41 1.366(7) . ? C41 C42 1.414(7) . ? C43 Cl1 1.597(13) . ? C43 Cl2 1.718(13) . ? 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 Ni1 N5 96.04(18) . . ? N2 Ni1 N3 85.43(19) . . ? N5 Ni1 N3 176.14(17) . . ? N2 Ni1 N4 178.45(18) . . ? N5 Ni1 N4 85.44(18) . . ? N3 Ni1 N4 93.12(19) . . ? C7 N1 C1 119.5(4) . . ? C9 N2 C12 107.0(4) . . ? C9 N2 Ni1 142.1(3) . . ? C12 N2 Ni1 110.8(4) . . ? C13 N3 C14 118.1(5) . . ? C13 N3 Ni1 112.9(4) . . ? C14 N3 Ni1 129.0(4) . . ? C17 N4 C16 119.2(5) . . ? C17 N4 Ni1 112.9(4) . . ? C16 N4 Ni1 127.8(4) . . ? C21 N5 C18 106.6(4) . . ? C21 N5 Ni1 143.1(3) . . ? C18 N5 Ni1 110.2(3) . . ? C2 N6 C8 120.8(4) . . ? N1 C1 C2 120.4(5) . . ? N1 C1 C6 119.4(5) . . ? C2 C1 C6 120.2(5) . . ? N6 C2 C1 120.1(5) . . ? N6 C2 C3 120.8(5) . . ? C1 C2 C3 119.0(5) . . ? C4 C3 C2 119.7(6) . . ? C3 C4 C5 120.9(6) . . ? C6 C5 C4 121.6(6) . . ? C5 C6 C1 118.5(6) . . ? N1 C7 C8 120.4(5) . . ? N1 C7 C9 111.1(4) . . ? C8 C7 C9 128.3(5) . . ? N6 C8 C21 112.4(4) . . ? N6 C8 C7 117.8(4) . . ? C21 C8 C7 129.7(4) . . ? N2 C9 C10 108.6(5) . . ? N2 C9 C7 129.1(4) . . ? C10 C9 C7 122.3(5) . . ? C11 C10 C9 108.1(5) . . ? C10 C11 C12 106.5(5) . . ? N2 C12 C11 109.9(5) . . ? N2 C12 C13 114.2(5) . . ? C11 C12 C13 135.8(5) . . ? N3 C13 C12 116.5(5) . . ? N3 C14 C15 110.6(5) . . ? C16 C15 C14 111.3(5) . . ? N4 C16 C15 112.0(5) . . ? N4 C17 C18 116.2(5) . . ? N5 C18 C19 110.0(5) . . ? N5 C18 C17 115.2(5) . . ? C19 C18 C17 134.8(5) . . ? C20 C19 C18 106.4(5) . . ? C19 C20 C21 108.6(5) . . ? N5 C21 C20 108.4(4) . . ? N5 C21 C8 128.6(4) . . ? C20 C21 C8 122.9(5) . . ? N8 Ni2 N11 96.13(17) . . ? N8 Ni2 N10 177.71(17) . . ? N11 Ni2 N10 85.41(18) . . ? N8 Ni2 N9 85.06(18) . . ? N11 Ni2 N9 178.65(19) . . ? N10 Ni2 N9 93.4(2) . . ? C28 N7 C22 120.5(4) . . ? C30 N8 C33 105.6(4) . . ? C30 N8 Ni2 142.9(3) . . ? C33 N8 Ni2 111.1(4) . . ? C34 N9 C35 119.5(5) . . ? C34 N9 Ni2 113.0(4) . . ? C35 N9 Ni2 127.5(4) . . ? C38 N10 C37 118.9(5) . . ? C38 N10 Ni2 112.5(4) . . ? C37 N10 Ni2 128.6(4) . . ? C42 N11 C39 106.0(4) . . ? C42 N11 Ni2 142.8(3) . . ? C39 N11 Ni2 111.2(3) . . ? C29 N12 C23 121.1(4) . . ? N7 C22 C27 120.7(5) . . ? N7 C22 C23 119.7(5) . . ? C27 C22 C23 119.5(5) . . ? N12 C23 C24 121.1(5) . . ? N12 C23 C22 119.7(5) . . ? C24 C23 C22 119.0(5) . . ? C25 C24 C23 119.8(6) . . ? C24 C25 C26 121.0(6) . . ? C27 C26 C25 120.4(6) . . ? C26 C27 C22 120.3(6) . . ? N7 C28 C29 119.4(4) . . ? N7 C28 C30 111.3(4) . . ? C29 C28 C30 129.3(5) . . ? N12 C29 C28 118.6(4) . . ? N12 C29 C42 112.0(4) . . ? C28 C29 C42 129.3(4) . . ? N8 C30 C31 109.0(5) . . ? N8 C30 C28 128.9(5) . . ? C31 C30 C28 122.1(5) . . ? C32 C31 C30 108.0(5) . . ? C33 C32 C31 105.9(5) . . ? C32 C33 N8 111.6(5) . . ? C32 C33 C34 134.3(5) . . ? N8 C33 C34 114.0(5) . . ? N9 C34 C33 116.8(5) . . ? N9 C35 C36 112.2(4) . . ? C37 C36 C35 111.3(5) . . ? N10 C37 C36 111.7(5) . . ? N10 C38 C39 117.5(5) . . ? N11 C39 C40 110.6(5) . . ? N11 C39 C38 113.3(5) . . ? C40 C39 C38 136.1(5) . . ? C41 C40 C39 106.9(5) . . ? C40 C41 C42 107.4(5) . . ? N11 C42 C41 109.1(4) . . ? N11 C42 C29 129.1(4) . . ? C41 C42 C29 121.7(5) . . ? Cl1 C43 Cl2 119.4(9) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.648 _refine_diff_density_min -0.677 _refine_diff_density_rms 0.203 data_wy1104wc _database_code_depnum_ccdc_archive 'CCDC 254888' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H20 N6' _chemical_formula_weight 368.44 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 0.0000 '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 0.0000 '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 25.4999(12) _cell_length_b 4.9181(2) _cell_length_c 28.3899(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3560.4(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour orange _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.6642 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Smart CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16235 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3193 _reflns_number_gt 2859 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0781P)^2^+0.7824P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3193 _refine_ls_number_parameters 521 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1227 _refine_ls_wR_factor_gt 0.1163 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.109 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.004 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 0.12669(14) 1.2393(8) 0.08405(14) 0.0466(9) Uani 1 1 d . . . H1A H 0.1243 1.1954 0.0523 0.056 Uiso 1 1 calc R . . C2 C 0.09557(15) 1.4412(8) 0.10251(15) 0.0488(9) Uani 1 1 d . . . H2A H 0.0722 1.5346 0.0832 0.059 Uiso 1 1 calc R . . C3 C 0.09907(16) 1.5061(9) 0.15058(16) 0.0527(10) Uani 1 1 d . . . H3A H 0.0778 1.6427 0.1628 0.063 Uiso 1 1 calc R . . C4 C 0.13282(16) 1.3737(8) 0.17957(14) 0.0491(10) Uani 1 1 d . . . H4A H 0.1346 1.4207 0.2113 0.059 Uiso 1 1 calc R . . C5 C 0.16526(14) 1.1645(8) 0.16175(13) 0.0413(8) Uani 1 1 d . . . C6 C 0.16232(13) 1.0984(7) 0.11338(13) 0.0387(8) Uani 1 1 d . . . C7 C 0.23003(14) 0.8404(8) 0.17286(12) 0.0395(8) Uani 1 1 d . . . C8 C 0.26461(15) 0.7231(8) 0.20939(13) 0.0421(8) Uani 1 1 d . . . C9 C 0.26692(17) 0.8114(9) 0.25623(14) 0.0537(10) Uani 1 1 d . . . H9A H 0.2466 0.9470 0.2699 0.064 Uiso 1 1 calc R . . C10 C 0.30512(18) 0.6586(10) 0.27810(14) 0.0555(11) Uani 1 1 d . . . H10A H 0.3153 0.6720 0.3095 0.067 Uiso 1 1 calc R . . C11 C 0.32575(16) 0.4806(9) 0.24484(13) 0.0485(10) Uani 1 1 d . . . C12 C 0.36800(17) 0.2970(9) 0.25057(17) 0.0558(11) Uani 1 1 d . . . H12A H 0.3835 0.2860 0.2802 0.067 Uiso 1 1 calc R . . C13 C 0.4322(2) -0.0319(12) 0.2271(2) 0.0749(15) Uani 1 1 d . . . H13A H 0.4208 -0.2192 0.2301 0.090 Uiso 1 1 calc R . . H13B H 0.4486 0.0216 0.2565 0.090 Uiso 1 1 calc R . . C14 C 0.4709(2) -0.0093(13) 0.1879(2) 0.0832(16) Uani 1 1 d . . . H14A H 0.5052 -0.0515 0.2007 0.100 Uiso 1 1 calc R . . H14B H 0.4718 0.1796 0.1781 0.100 Uiso 1 1 calc R . . C15 C 0.46351(18) -0.1817(13) 0.1440(2) 0.0773(15) Uani 1 1 d . . . H15A H 0.4807 -0.0884 0.1181 0.093 Uiso 1 1 calc R . . H15B H 0.4822 -0.3510 0.1488 0.093 Uiso 1 1 calc R . . C16 C 0.40921(18) -0.2523(10) 0.1280(2) 0.0682(13) Uani 1 1 d . . . H16A H 0.4115 -0.3419 0.0976 0.082 Uiso 1 1 calc R . . H16B H 0.3943 -0.3812 0.1501 0.082 Uiso 1 1 calc R . . C17 C 0.34985(15) 0.0301(8) 0.08509(16) 0.0479(9) Uani 1 1 d D . . H17A H 0.3578 -0.0790 0.0593 0.057 Uiso 1 1 calc R . . C18 C 0.31232(13) 0.2386(8) 0.07820(13) 0.0411(8) Uani 1 1 d . . . C19 C 0.28766(15) 0.3125(9) 0.03642(14) 0.0476(9) Uani 1 1 d . . . H19A H 0.2929 0.2352 0.0069 0.057 Uiso 1 1 calc R . . C20 C 0.25366(15) 0.5239(8) 0.04732(13) 0.0446(9) Uani 1 1 d . . . H20A H 0.2322 0.6175 0.0264 0.054 Uiso 1 1 calc R . . C21 C 0.25780(13) 0.5696(7) 0.09630(13) 0.0368(8) Uani 1 1 d . . . C22 C 0.22731(13) 0.7719(7) 0.12275(12) 0.0359(8) Uani 1 1 d . . . C23 C 0.37296(17) 0.9312(9) 0.38539(16) 0.0548(11) Uani 1 1 d . . . H23A H 0.3749 0.9877 0.3542 0.066 Uiso 1 1 calc R . . C24 C 0.33873(17) 1.0508(9) 0.41518(18) 0.0584(11) Uani 1 1 d . . . H24A H 0.3173 1.1908 0.4044 0.070 Uiso 1 1 calc R . . C25 C 0.33513(17) 0.9648(9) 0.46272(18) 0.0564(11) Uani 1 1 d . . . H25A H 0.3111 1.0471 0.4828 0.068 Uiso 1 1 calc R . . C26 C 0.36637(15) 0.7639(8) 0.47911(15) 0.0492(9) Uani 1 1 d . . . H26A H 0.3636 0.7090 0.5104 0.059 Uiso 1 1 calc R . . C27 C 0.40326(14) 0.6366(7) 0.44915(13) 0.0409(8) Uani 1 1 d . . . C28 C 0.40599(14) 0.7188(8) 0.40182(14) 0.0426(8) Uani 1 1 d . . . C29 C 0.47001(13) 0.3255(7) 0.43725(12) 0.0372(8) Uani 1 1 d . . . C30 C 0.50167(14) 0.1204(7) 0.46175(13) 0.0381(8) Uani 1 1 d . . . C31 C 0.49700(16) 0.0563(8) 0.51017(14) 0.0478(9) Uani 1 1 d . . . H31A H 0.4746 0.1380 0.5318 0.057 Uiso 1 1 calc R . . C32 C 0.53190(16) -0.1494(9) 0.51910(15) 0.0527(10) Uani 1 1 d . . . H32A H 0.5373 -0.2344 0.5480 0.063 Uiso 1 1 calc R . . C33 C 0.55783(15) -0.2079(8) 0.47713(14) 0.0460(9) Uani 1 1 d . . . C34 C 0.59636(17) -0.4075(9) 0.46847(18) 0.0568(11) Uani 1 1 d . . . H34A H 0.6048 -0.5236 0.4932 0.068 Uiso 1 1 calc R . . C35 C 0.6570(2) -0.6661(11) 0.4230(3) 0.089(2) Uani 1 1 d . . . H35A H 0.6427 -0.7907 0.3998 0.107 Uiso 1 1 calc R . . H35B H 0.6603 -0.7640 0.4525 0.107 Uiso 1 1 calc R . . C36 C 0.71168(19) -0.5749(14) 0.4068(2) 0.089(2) Uani 1 1 d . . . H36A H 0.7315 -0.7361 0.3984 0.106 Uiso 1 1 calc R . . H36B H 0.7292 -0.4915 0.4334 0.106 Uiso 1 1 calc R . . C37 C 0.7148(2) -0.3623(14) 0.3624(3) 0.098(2) Uani 1 1 d . . . H37A H 0.7101 -0.1797 0.3746 0.117 Uiso 1 1 calc R . . H37B H 0.7498 -0.3721 0.3491 0.117 Uiso 1 1 calc R . . C38 C 0.6783(2) -0.4016(13) 0.3254(2) 0.0861(18) Uani 1 1 d . . . H38A H 0.6695 -0.5929 0.3229 0.103 Uiso 1 1 calc R . . H38B H 0.6936 -0.3442 0.2958 0.103 Uiso 1 1 calc R . . C39 C 0.6127(2) -0.0756(11) 0.3048(2) 0.0707(15) Uani 1 1 d . . . H39A H 0.6291 -0.0676 0.2756 0.085 Uiso 1 1 calc R . . C40 C 0.57020(18) 0.0971(10) 0.31210(15) 0.0570(11) Uani 1 1 d . . . C41 C 0.5498(2) 0.2896(11) 0.28195(15) 0.0697(14) Uani 1 1 d . . . H41A H 0.5607 0.3205 0.2511 0.084 Uiso 1 1 calc R . . C42 C 0.51118(18) 0.4268(11) 0.30495(15) 0.0625(12) Uani 1 1 d . . . H42A H 0.4907 0.5669 0.2930 0.075 Uiso 1 1 calc R . . C43 C 0.50843(15) 0.3135(8) 0.35089(14) 0.0466(9) Uani 1 1 d . . . C44 C 0.47262(14) 0.4079(8) 0.38788(13) 0.0418(8) Uani 1 1 d . . . N1 N 0.19902(12) 1.0303(7) 0.19034(11) 0.0430(7) Uani 1 1 d . . . N2 N 0.30034(13) 0.5229(7) 0.20309(12) 0.0456(8) Uani 1 1 d D . . N3 N 0.38658(15) 0.1441(8) 0.21775(14) 0.0607(10) Uani 1 1 d D . . N4 N 0.37381(13) -0.0214(7) 0.12385(14) 0.0545(9) Uani 1 1 d D . . N5 N 0.29381(11) 0.3956(7) 0.11441(11) 0.0417(7) Uani 1 1 d . . . N6 N 0.19353(11) 0.9033(6) 0.09500(11) 0.0402(7) Uani 1 1 d . . . N7 N 0.43533(11) 0.4403(6) 0.46569(11) 0.0399(7) Uani 1 1 d . . . N8 N 0.53859(12) -0.0416(7) 0.44291(12) 0.0450(7) Uani 1 1 d D . . N9 N 0.62071(14) -0.4427(8) 0.42941(17) 0.0669(11) Uani 1 1 d . . . N10 N 0.63116(18) -0.2442(10) 0.3348(2) 0.0787(13) Uani 1 1 d D . . N11 N 0.54422(13) 0.1129(7) 0.35492(12) 0.0526(9) Uani 1 1 d . . . N12 N 0.44039(13) 0.5991(7) 0.37175(11) 0.0472(8) Uani 1 1 d . . . H2 H 0.304(2) 0.444(12) 0.1737(12) 0.09(2) Uiso 1 1 d D . . H8 H 0.549(2) -0.050(12) 0.4116(9) 0.087(18) Uiso 1 1 d D . . H10 H 0.611(4) -0.26(2) 0.361(3) 0.28(6) Uiso 1 1 d D . . H4 H 0.374(2) 0.14(2) 0.1509(11) 0.31(7) Uiso 1 1 d 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 0.0404(19) 0.053(2) 0.046(2) -0.0028(18) -0.0021(16) -0.0018(17) C2 0.039(2) 0.051(2) 0.056(2) -0.0001(18) 0.0017(17) 0.0006(17) C3 0.049(2) 0.053(2) 0.057(2) -0.001(2) 0.0152(19) 0.0080(19) C4 0.051(2) 0.054(2) 0.043(2) -0.0073(18) 0.0108(18) -0.0002(18) C5 0.0396(19) 0.044(2) 0.041(2) 0.0013(16) 0.0059(15) -0.0061(16) C6 0.0356(18) 0.0404(18) 0.0403(19) -0.0013(15) 0.0049(15) -0.0073(15) C7 0.0382(18) 0.044(2) 0.0359(18) 0.0028(16) 0.0035(15) -0.0100(15) C8 0.0418(19) 0.048(2) 0.0365(18) 0.0037(16) 0.0024(15) -0.0108(16) C9 0.057(2) 0.065(3) 0.039(2) -0.0049(19) 0.0020(18) -0.005(2) C10 0.061(2) 0.072(3) 0.0340(19) 0.0043(19) -0.0051(18) -0.012(2) C11 0.050(2) 0.058(2) 0.038(2) 0.0093(18) -0.0087(17) -0.0134(19) C12 0.054(2) 0.063(3) 0.051(2) 0.019(2) -0.0102(19) -0.013(2) C13 0.062(3) 0.078(3) 0.085(4) 0.022(3) -0.021(3) 0.005(3) C14 0.051(3) 0.094(4) 0.104(4) 0.010(4) -0.008(3) -0.001(3) C15 0.048(2) 0.104(4) 0.080(4) 0.019(3) 0.001(2) 0.012(3) C16 0.054(3) 0.065(3) 0.086(3) 0.005(3) -0.006(2) 0.014(2) C17 0.0383(19) 0.047(2) 0.059(3) -0.0076(19) 0.0054(18) -0.0024(17) C18 0.0350(18) 0.048(2) 0.0404(19) -0.0014(16) 0.0030(15) -0.0044(15) C19 0.043(2) 0.059(2) 0.040(2) -0.0087(18) 0.0029(16) 0.0015(18) C20 0.0407(19) 0.057(2) 0.0364(19) -0.0012(17) -0.0022(16) 0.0042(18) C21 0.0316(17) 0.0397(18) 0.0392(18) 0.0008(15) 0.0018(14) -0.0045(14) C22 0.0336(17) 0.0379(18) 0.0361(18) -0.0015(14) 0.0028(14) -0.0081(14) C23 0.056(2) 0.057(2) 0.051(2) 0.008(2) -0.018(2) -0.007(2) C24 0.045(2) 0.055(2) 0.075(3) 0.003(2) -0.019(2) 0.0032(19) C25 0.043(2) 0.057(3) 0.070(3) -0.005(2) -0.004(2) 0.0051(19) C26 0.043(2) 0.055(2) 0.049(2) -0.0004(19) 0.0008(17) 0.0037(18) C27 0.0378(18) 0.0401(19) 0.045(2) -0.0008(16) -0.0041(15) -0.0062(15) C28 0.0402(19) 0.045(2) 0.0430(19) 0.0013(16) -0.0061(16) -0.0056(17) C29 0.0356(17) 0.0414(19) 0.0347(18) -0.0006(15) -0.0015(14) -0.0064(15) C30 0.0330(17) 0.0418(18) 0.0395(19) -0.0033(15) -0.0017(14) -0.0051(15) C31 0.045(2) 0.060(2) 0.039(2) -0.0008(17) -0.0002(16) 0.0027(19) C32 0.053(2) 0.060(3) 0.045(2) 0.0082(19) -0.0101(18) 0.005(2) C33 0.0372(19) 0.049(2) 0.052(2) -0.0007(18) -0.0103(16) 0.0010(17) C34 0.045(2) 0.050(2) 0.075(3) -0.005(2) -0.014(2) -0.0016(18) C35 0.059(3) 0.068(3) 0.140(6) -0.040(4) 0.002(3) 0.014(3) C36 0.047(3) 0.105(5) 0.115(5) -0.053(4) -0.011(3) 0.016(3) C37 0.057(3) 0.109(5) 0.127(6) -0.053(5) 0.020(3) -0.015(3) C38 0.067(3) 0.087(4) 0.104(4) -0.032(3) 0.022(3) 0.004(3) C39 0.070(3) 0.070(3) 0.072(3) -0.032(3) 0.029(3) -0.023(3) C40 0.057(2) 0.070(3) 0.044(2) -0.016(2) 0.014(2) -0.019(2) C41 0.073(3) 0.097(4) 0.039(2) -0.007(2) 0.016(2) -0.030(3) C42 0.059(3) 0.086(3) 0.042(2) 0.009(2) 0.002(2) -0.009(2) C43 0.046(2) 0.057(2) 0.0372(19) -0.0026(18) 0.0016(17) -0.0102(18) C44 0.0381(19) 0.048(2) 0.0390(19) -0.0013(17) -0.0024(15) -0.0114(16) N1 0.0457(17) 0.0479(17) 0.0355(16) -0.0026(14) 0.0036(14) -0.0020(15) N2 0.0473(17) 0.0524(19) 0.0370(18) 0.0027(15) -0.0033(14) -0.0021(16) N3 0.052(2) 0.062(2) 0.068(2) 0.013(2) -0.0143(18) 0.0003(18) N4 0.0446(18) 0.0519(19) 0.067(2) 0.0036(18) -0.0060(17) 0.0076(15) N5 0.0374(16) 0.0456(17) 0.0421(16) -0.0011(14) 0.0015(13) -0.0028(13) N6 0.0358(15) 0.0458(17) 0.0388(16) -0.0023(14) 0.0001(13) -0.0022(13) N7 0.0358(16) 0.0462(17) 0.0378(16) 0.0015(13) -0.0011(13) 0.0006(13) N8 0.0382(17) 0.0535(19) 0.0433(18) -0.0057(15) 0.0006(14) 0.0011(15) N9 0.0433(19) 0.059(2) 0.098(3) -0.027(2) 0.001(2) 0.0044(17) N10 0.068(3) 0.071(3) 0.098(4) -0.020(3) 0.037(3) 0.000(2) N11 0.0516(19) 0.063(2) 0.0432(18) -0.0124(17) 0.0106(15) -0.0120(18) N12 0.0473(18) 0.0535(19) 0.0407(17) 0.0041(14) -0.0065(14) -0.0079(16) _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 1.375(5) . ? C1 C6 1.414(5) . ? C2 C3 1.404(6) . ? C3 C4 1.357(6) . ? C4 C5 1.413(5) . ? C5 N1 1.355(5) . ? C5 C6 1.413(5) . ? C6 N6 1.351(5) . ? C7 N1 1.321(5) . ? C7 C22 1.464(5) . ? C7 C8 1.478(5) . ? C8 N2 1.353(5) . ? C8 C9 1.400(6) . ? C9 C10 1.378(6) . ? C10 C11 1.391(6) . ? C11 N2 1.367(5) . ? C11 C12 1.415(6) . ? C12 N3 1.288(6) . ? C13 N3 1.474(6) . ? C13 C14 1.491(8) . ? C14 C15 1.521(9) . ? C15 C16 1.498(7) . ? C16 N4 1.455(6) . ? C17 N4 1.284(6) . ? C17 C18 1.416(6) . ? C18 N5 1.369(5) . ? C18 C19 1.391(5) . ? C19 C20 1.389(6) . ? C20 C21 1.412(5) . ? C21 N5 1.357(5) . ? C21 C22 1.469(5) . ? C22 N6 1.334(5) . ? C23 C24 1.350(7) . ? C23 C28 1.421(6) . ? C24 C25 1.418(7) . ? C25 C26 1.352(6) . ? C26 C27 1.414(5) . ? C27 N7 1.350(5) . ? C27 C28 1.405(5) . ? C28 N12 1.358(5) . ? C29 N7 1.324(5) . ? C29 C44 1.460(5) . ? C29 C30 1.467(5) . ? C30 N8 1.344(5) . ? C30 C31 1.415(6) . ? C31 C32 1.371(6) . ? C32 C33 1.393(6) . ? C33 N8 1.361(5) . ? C33 C34 1.411(6) . ? C34 N9 1.283(7) . ? C35 N9 1.448(6) . ? C35 C36 1.535(8) . ? C36 C37 1.639(10) . ? C37 C38 1.417(9) . ? C38 N10 1.454(7) . ? C39 N10 1.278(7) . ? C39 C40 1.392(7) . ? C40 C41 1.378(7) . ? C40 N11 1.387(5) . ? C41 C42 1.361(7) . ? C42 C43 1.420(6) . ? C43 N11 1.349(6) . ? C43 C44 1.467(5) . ? C44 N12 1.330(5) . ? 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 120.0(4) . . ? C1 C2 C3 119.9(4) . . ? C4 C3 C2 121.4(4) . . ? C3 C4 C5 120.2(4) . . ? N1 C5 C4 120.8(4) . . ? N1 C5 C6 120.2(3) . . ? C4 C5 C6 119.0(4) . . ? N6 C6 C1 120.0(3) . . ? N6 C6 C5 120.5(3) . . ? C1 C6 C5 119.6(3) . . ? N1 C7 C22 120.0(3) . . ? N1 C7 C8 111.7(3) . . ? C22 C7 C8 128.4(3) . . ? N2 C8 C9 108.8(4) . . ? N2 C8 C7 126.4(3) . . ? C9 C8 C7 124.8(4) . . ? C10 C9 C8 106.8(4) . . ? C9 C10 C11 107.7(4) . . ? N2 C11 C10 108.3(4) . . ? N2 C11 C12 123.9(4) . . ? C10 C11 C12 127.7(4) . . ? N3 C12 C11 124.7(4) . . ? N3 C13 C14 110.2(4) . . ? C13 C14 C15 119.2(5) . . ? C16 C15 C14 119.5(5) . . ? N4 C16 C15 114.7(4) . . ? N4 C17 C18 125.6(4) . . ? N5 C18 C19 109.7(3) . . ? N5 C18 C17 122.5(3) . . ? C19 C18 C17 127.8(4) . . ? C20 C19 C18 106.7(3) . . ? C19 C20 C21 107.0(3) . . ? N5 C21 C20 108.9(3) . . ? N5 C21 C22 126.3(3) . . ? C20 C21 C22 124.9(3) . . ? N6 C22 C7 119.6(3) . . ? N6 C22 C21 111.6(3) . . ? C7 C22 C21 128.9(3) . . ? C24 C23 C28 119.9(4) . . ? C23 C24 C25 120.5(4) . . ? C26 C25 C24 120.5(4) . . ? C25 C26 C27 120.6(4) . . ? N7 C27 C28 120.6(3) . . ? N7 C27 C26 120.7(3) . . ? C28 C27 C26 118.7(4) . . ? N12 C28 C27 120.6(3) . . ? N12 C28 C23 119.7(4) . . ? C27 C28 C23 119.8(4) . . ? N7 C29 C44 119.8(3) . . ? N7 C29 C30 111.8(3) . . ? C44 C29 C30 128.4(3) . . ? N8 C30 C31 108.3(3) . . ? N8 C30 C29 127.2(3) . . ? C31 C30 C29 124.6(3) . . ? C32 C31 C30 106.8(4) . . ? C31 C32 C33 107.6(4) . . ? N8 C33 C32 108.4(3) . . ? N8 C33 C34 123.0(4) . . ? C32 C33 C34 128.6(4) . . ? N9 C34 C33 125.6(5) . . ? N9 C35 C36 113.4(5) . . ? C35 C36 C37 117.4(5) . . ? C38 C37 C36 116.8(5) . . ? C37 C38 N10 109.5(5) . . ? N10 C39 C40 125.7(5) . . ? C41 C40 N11 109.0(4) . . ? C41 C40 C39 128.3(4) . . ? N11 C40 C39 122.4(5) . . ? C42 C41 C40 108.4(4) . . ? C41 C42 C43 106.4(4) . . ? N11 C43 C42 109.4(4) . . ? N11 C43 C44 126.3(4) . . ? C42 C43 C44 124.3(4) . . ? N12 C44 C29 119.9(3) . . ? N12 C44 C43 111.2(3) . . ? C29 C44 C43 128.9(4) . . ? C7 N1 C5 120.0(3) . . ? C8 N2 C11 108.4(3) . . ? C12 N3 C13 120.2(4) . . ? C17 N4 C16 121.2(4) . . ? C21 N5 C18 107.7(3) . . ? C22 N6 C6 119.7(3) . . ? C29 N7 C27 119.8(3) . . ? C30 N8 C33 108.9(3) . . ? C34 N9 C35 121.4(5) . . ? C39 N10 C38 121.8(5) . . ? C43 N11 C40 106.8(4) . . ? C44 N12 C28 119.3(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.452 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.041 data_p21c_b _database_code_depnum_ccdc_archive 'CCDC 256611' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 N6' _chemical_formula_weight 354.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.2969(8) _cell_length_b 11.0235(10) _cell_length_c 16.9434(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.496(2) _cell_angle_gamma 90.00 _cell_volume 1736.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.9749 _exptl_absorpt_correction_T_max 0.9873 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Smart CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8447 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3048 _reflns_number_gt 1834 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0631P)^2^+0.4027P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3048 _refine_ls_number_parameters 252 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0937 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1418 _refine_ls_wR_factor_gt 0.1167 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 0.7701(2) 0.10111(18) 0.03941(11) 0.0511(5) Uani 1 1 d . . . N2 N 0.9597(2) 0.03111(18) 0.21948(11) 0.0499(5) Uani 1 1 d . . . N3 N 1.0932(3) -0.0129(3) 0.36667(15) 0.0765(7) Uani 1 1 d D . . N4 N 1.3409(3) 0.0702(2) 0.30772(14) 0.0728(7) Uani 1 1 d . . . N5 N 1.1998(2) 0.11942(18) 0.16234(12) 0.0509(5) Uani 1 1 d D . . N6 N 1.0250(2) 0.18955(18) -0.02275(12) 0.0528(5) Uani 1 1 d . . . C1 C 0.7728(3) 0.1459(2) -0.03498(14) 0.0494(6) Uani 1 1 d . . . C2 C 0.9023(3) 0.1896(2) -0.06705(14) 0.0503(6) Uani 1 1 d . . . C3 C 0.9032(3) 0.2330(2) -0.14525(15) 0.0639(7) Uani 1 1 d . . . H3B H 0.9880 0.2619 -0.1671 0.077 Uiso 1 1 calc R . . C4 C 0.7792(3) 0.2324(3) -0.18856(16) 0.0697(8) Uani 1 1 d . . . H4B H 0.7800 0.2607 -0.2403 0.084 Uiso 1 1 calc R . . C5 C 0.6502(3) 0.1896(3) -0.15632(17) 0.0679(8) Uani 1 1 d . . . H5B H 0.5665 0.1903 -0.1868 0.081 Uiso 1 1 calc R . . C6 C 0.6461(3) 0.1473(2) -0.08128(15) 0.0607(7) Uani 1 1 d . . . H6B H 0.5601 0.1192 -0.0604 0.073 Uiso 1 1 calc R . . C7 C 0.8908(2) 0.0952(2) 0.08203(13) 0.0454(6) Uani 1 1 d . . . C8 C 1.0242(2) 0.1436(2) 0.04985(13) 0.0465(6) Uani 1 1 d . . . C9 C 0.8678(2) 0.0330(2) 0.15764(13) 0.0459(6) Uani 1 1 d . . . C10 C 0.7443(3) -0.0353(2) 0.17610(15) 0.0590(7) Uani 1 1 d . . . H10A H 0.6644 -0.0480 0.1437 0.071 Uiso 1 1 calc R . . C11 C 0.7648(3) -0.0792(3) 0.25091(16) 0.0631(7) Uani 1 1 d . . . H11A H 0.7009 -0.1275 0.2788 0.076 Uiso 1 1 calc R . . C12 C 0.8983(2) -0.0385(2) 0.27772(14) 0.0517(6) Uani 1 1 d . . . C13 C 0.9691(3) -0.0590(3) 0.34993(16) 0.0651(7) Uani 1 1 d . . . H13A H 0.9247 -0.1079 0.3873 0.078 Uiso 1 1 calc R . . C14 C 1.1730(3) -0.0339(4) 0.43973(18) 0.0931(11) Uani 1 1 d . . . H14A H 1.1316 -0.1023 0.4674 0.112 Uiso 1 1 calc R . . H14B H 1.1654 0.0369 0.4734 0.112 Uiso 1 1 calc R . . C15 C 1.3266(4) -0.0587(4) 0.4236(2) 0.1078(13) Uani 1 1 d . . . H15A H 1.3315 -0.1322 0.3923 0.129 Uiso 1 1 calc R . . H15B H 1.3740 -0.0756 0.4736 0.129 Uiso 1 1 calc R . . C16 C 1.4106(3) 0.0363(3) 0.38265(18) 0.0845(10) Uani 1 1 d . . . H16A H 1.4188 0.1072 0.4163 0.101 Uiso 1 1 calc R . . H16B H 1.5068 0.0064 0.3725 0.101 Uiso 1 1 calc R . . C17 C 1.4125(3) 0.0998(3) 0.24611(18) 0.0664(8) Uani 1 1 d . . . H17A H 1.5123 0.1020 0.2495 0.080 Uiso 1 1 calc R . . C18 C 1.3452(2) 0.1294(2) 0.17294(16) 0.0548(7) Uani 1 1 d . . . C19 C 1.4058(3) 0.1670(3) 0.10223(16) 0.0653(8) Uani 1 1 d . . . H19A H 1.5028 0.1812 0.0932 0.078 Uiso 1 1 calc R . . C20 C 1.2958(3) 0.1792(2) 0.04818(16) 0.0611(7) Uani 1 1 d . . . H20A H 1.3042 0.2036 -0.0041 0.073 Uiso 1 1 calc R . . C21 C 1.1679(2) 0.1479(2) 0.08716(14) 0.0476(6) Uani 1 1 d . . . H3A H 1.147(6) 0.030(6) 0.329(3) 0.30(4) Uiso 1 1 d D . . H5A H 1.131(3) 0.089(3) 0.2018(16) 0.133(13) Uiso 1 1 d 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 N1 0.0449(11) 0.0548(13) 0.0537(12) -0.0004(10) 0.0017(9) 0.0006(9) N2 0.0445(11) 0.0538(13) 0.0514(12) 0.0056(10) 0.0041(9) 0.0012(9) N3 0.0663(16) 0.092(2) 0.0704(16) 0.0240(14) -0.0149(13) -0.0015(14) N4 0.0624(15) 0.0845(19) 0.0714(16) 0.0018(14) -0.0123(13) -0.0011(13) N5 0.0396(12) 0.0537(13) 0.0595(14) -0.0017(10) 0.0033(10) -0.0030(9) N6 0.0524(13) 0.0499(13) 0.0563(13) 0.0021(10) 0.0066(10) 0.0015(10) C1 0.0511(15) 0.0442(15) 0.0528(15) -0.0030(12) -0.0001(12) 0.0049(11) C2 0.0562(16) 0.0416(15) 0.0531(15) -0.0009(12) 0.0016(12) 0.0031(11) C3 0.0727(18) 0.0556(18) 0.0635(17) 0.0084(14) 0.0059(14) -0.0025(14) C4 0.090(2) 0.0608(19) 0.0584(17) 0.0111(14) -0.0096(16) 0.0015(16) C5 0.0717(19) 0.0620(19) 0.0698(19) 0.0048(15) -0.0122(15) 0.0025(15) C6 0.0564(16) 0.0630(18) 0.0626(17) 0.0032(14) -0.0035(13) -0.0004(13) C7 0.0431(13) 0.0413(14) 0.0518(14) -0.0045(11) 0.0044(11) 0.0030(10) C8 0.0461(14) 0.0415(14) 0.0522(14) -0.0022(11) 0.0074(11) 0.0017(10) C9 0.0398(13) 0.0486(15) 0.0494(14) -0.0008(11) 0.0050(11) 0.0028(11) C10 0.0458(14) 0.0683(19) 0.0629(17) 0.0050(14) 0.0009(12) -0.0105(13) C11 0.0541(16) 0.0640(18) 0.0714(18) 0.0117(15) 0.0093(13) -0.0118(13) C12 0.0488(15) 0.0531(16) 0.0532(15) 0.0099(12) 0.0048(11) -0.0003(11) C13 0.0701(19) 0.0601(19) 0.0653(18) 0.0164(14) 0.0049(14) 0.0004(14) C14 0.086(2) 0.118(3) 0.075(2) 0.033(2) -0.0233(18) -0.006(2) C15 0.100(3) 0.126(3) 0.096(3) 0.028(2) -0.038(2) 0.001(2) C16 0.071(2) 0.105(3) 0.077(2) 0.0021(19) -0.0218(17) -0.0001(19) C17 0.0436(15) 0.0653(19) 0.090(2) -0.0173(16) -0.0110(15) 0.0008(13) C18 0.0385(13) 0.0537(17) 0.0721(18) -0.0082(13) 0.0002(12) -0.0031(11) C19 0.0418(15) 0.070(2) 0.084(2) -0.0060(15) 0.0121(14) -0.0119(13) C20 0.0504(16) 0.0631(19) 0.0699(17) 0.0061(14) 0.0111(13) -0.0051(12) C21 0.0424(13) 0.0426(15) 0.0578(15) -0.0004(12) 0.0068(11) -0.0022(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C7 1.330(3) . ? N1 C1 1.354(3) . ? N2 C9 1.346(3) . ? N2 C12 1.378(3) . ? N3 C13 1.290(3) . ? N3 C14 1.456(4) . ? N4 C17 1.285(3) . ? N4 C16 1.469(3) . ? N5 C21 1.343(3) . ? N5 C18 1.367(3) . ? N6 C8 1.330(3) . ? N6 C2 1.360(3) . ? C1 C6 1.409(3) . ? C1 C2 1.410(3) . ? C2 C3 1.409(3) . ? C3 C4 1.361(3) . ? C4 C5 1.404(4) . ? C5 C6 1.355(3) . ? C7 C8 1.460(3) . ? C7 C9 1.471(3) . ? C8 C21 1.473(3) . ? C9 C10 1.410(3) . ? C10 C11 1.368(3) . ? C11 C12 1.392(3) . ? C12 C13 1.403(3) . ? C14 C15 1.481(5) . ? C15 C16 1.482(5) . ? C17 C18 1.422(4) . ? C18 C19 1.391(4) . ? C19 C20 1.373(3) . ? C20 C21 1.409(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 C7 N1 C1 120.0(2) . . ? C9 N2 C12 107.56(19) . . ? C13 N3 C14 124.9(3) . . ? C17 N4 C16 122.6(2) . . ? C21 N5 C18 108.4(2) . . ? C8 N6 C2 119.9(2) . . ? N1 C1 C6 120.0(2) . . ? N1 C1 C2 120.4(2) . . ? C6 C1 C2 119.6(2) . . ? N6 C2 C3 120.5(2) . . ? N6 C2 C1 120.1(2) . . ? C3 C2 C1 119.4(2) . . ? C4 C3 C2 119.5(3) . . ? C3 C4 C5 121.0(3) . . ? C6 C5 C4 120.8(3) . . ? C5 C6 C1 119.7(3) . . ? N1 C7 C8 119.6(2) . . ? N1 C7 C9 111.6(2) . . ? C8 C7 C9 128.8(2) . . ? N6 C8 C7 119.7(2) . . ? N6 C8 C21 111.87(19) . . ? C7 C8 C21 128.4(2) . . ? N2 C9 C10 109.4(2) . . ? N2 C9 C7 126.1(2) . . ? C10 C9 C7 124.5(2) . . ? C11 C10 C9 106.7(2) . . ? C10 C11 C12 107.8(2) . . ? N2 C12 C11 108.6(2) . . ? N2 C12 C13 121.4(2) . . ? C11 C12 C13 130.0(2) . . ? N3 C13 C12 122.7(3) . . ? N3 C14 C15 110.9(3) . . ? C14 C15 C16 117.9(3) . . ? N4 C16 C15 110.7(3) . . ? N4 C17 C18 122.7(2) . . ? N5 C18 C19 108.5(2) . . ? N5 C18 C17 121.6(2) . . ? C19 C18 C17 129.9(2) . . ? C20 C19 C18 107.4(2) . . ? C19 C20 C21 106.9(2) . . ? N5 C21 C20 108.8(2) . . ? N5 C21 C8 126.3(2) . . ? C20 C21 C8 124.9(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.302 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.037