Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 186 loop_ _publ_author_name 'Clyburne, Jason A.' 'Abeysekera, Deepa' 'Dickie, Diane A.' 'Jenkins, Hilary A.' _publ_contact_author_name 'Jason A Clyburne' _publ_contact_author_address ; Department of Chemistry Simon Fraser University Burnaby British Coumbia V5A 1S6 CANADA ; _publ_contact_author_email 'CLYBURNE@SFU.CA' _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Double lithiation of 2,4,6-triphenylbromobenzene: Synthesis of bis-amidines and an aluminium bis-amidinate complex ; data_jcc20m _database_code_CSD 180739 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H46 N4' _chemical_formula_weight 558.79 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0339(16) _cell_length_b 10.1074(18) _cell_length_c 18.511(3) _cell_angle_alpha 98.273(3) _cell_angle_beta 90.256(4) _cell_angle_gamma 99.322(4) _cell_volume 1649.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max .3 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.125 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 9644 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0631 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6389 _reflns_number_gt 3847 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0492P)^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 SHELXL _refine_ls_extinction_coef 0.0043(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 6389 _refine_ls_number_parameters 560 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1045 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1160 _refine_ls_wR_factor_gt 0.1016 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.237 _refine_ls_shift/su_mean 0.009 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 0.29433(18) 0.19066(16) 0.17385(9) 0.0407(4) Uani 1 1 d . A . N2 N 0.4576(2) 0.28009(18) 0.27519(9) 0.0455(5) Uani 1 1 d . . . H2A H 0.527(3) 0.324(2) 0.2457(13) 0.075(8) Uiso 1 1 d . . . N3 N -0.11290(19) -0.22923(16) 0.14165(9) 0.0467(5) Uani 1 1 d . . . N4 N 0.0022(2) -0.01187(17) 0.12978(9) 0.0394(4) Uani 1 1 d . . . H4A H 0.084(2) 0.045(2) 0.1382(11) 0.049(7) Uiso 1 1 d . . . C1 C 0.3287(2) 0.20941(18) 0.24295(10) 0.0328(4) Uani 1 1 d . . . C2 C 0.4036(3) 0.2414(2) 0.12192(12) 0.0497(6) Uani 1 1 d . . . H2B H 0.508(2) 0.251(2) 0.1436(11) 0.055(6) Uiso 1 1 d . . . C3 C 0.418(2) 0.128(3) 0.0609(12) 0.085(5) Uani 0.50 1 d P A 1 H3C H 0.283(7) 0.139(7) 0.038(4) 0.102 Uiso 0.50 1 d P B 1 H3A H 0.502(6) 0.166(5) 0.027(3) 0.085(16) Uiso 0.50 1 d P C 1 H3B H 0.444(7) 0.054(6) 0.080(3) 0.09(2) Uiso 0.50 1 d P D 1 C3A C 0.3681(19) 0.149(2) 0.0491(10) 0.070(4) Uani 0.50 1 d P A 2 H3AA H 0.2765 0.1674 0.0277 0.104 Uiso 0.50 1 calc PR A 2 H3AB H 0.3550 0.0554 0.0570 0.104 Uiso 0.50 1 calc PR A 2 H3AC H 0.4502 0.1669 0.0164 0.104 Uiso 0.50 1 calc PR A 2 C4 C 0.3797(4) 0.3779(3) 0.10716(18) 0.1009(11) Uani 1 1 d . A . H4B H 0.4034 0.4432 0.1511 0.151 Uiso 1 1 calc R . . H4C H 0.2757 0.3739 0.0924 0.151 Uiso 1 1 calc R . . H4D H 0.4443 0.4052 0.0684 0.151 Uiso 1 1 calc R . . C5 C 0.5068(2) 0.2938(2) 0.35142(11) 0.0391(5) Uani 1 1 d . . . H5A H 0.416(2) 0.2555(18) 0.3790(10) 0.039(5) Uiso 1 1 d . . . C6 C 0.5536(3) 0.4435(3) 0.38195(17) 0.0627(7) Uani 1 1 d . . . H6A H 0.585(3) 0.456(3) 0.4359(16) 0.091(9) Uiso 1 1 d . . . H6B H 0.657(3) 0.473(2) 0.3539(13) 0.085(8) Uiso 1 1 d . . . H6C H 0.471(3) 0.496(3) 0.3717(13) 0.089(9) Uiso 1 1 d . . . C7 C 0.6355(3) 0.2174(3) 0.35908(15) 0.0578(7) Uani 1 1 d . . . H7B H 0.605(3) 0.116(3) 0.3425(13) 0.082(8) Uiso 1 1 d . . . H7A H 0.733(3) 0.259(3) 0.3281(15) 0.103(9) Uiso 1 1 d . . . H7C H 0.670(2) 0.230(2) 0.4133(14) 0.070(7) Uiso 1 1 d . . . C8 C 0.0072(2) -0.14026(19) 0.14343(10) 0.0373(5) Uani 1 1 d . . . C9 C -0.1043(3) -0.3709(2) 0.14632(13) 0.0505(6) Uani 1 1 d . . . H9A H 0.000(2) -0.382(2) 0.1563(11) 0.059(7) Uiso 1 1 d . . . C10 C -0.1562(5) -0.4534(3) 0.07234(18) 0.0789(9) Uani 1 1 d . . . H10B H -0.087(3) -0.423(3) 0.0319(16) 0.100(10) Uiso 1 1 d . . . H10A H -0.265(4) -0.444(3) 0.0607(17) 0.127(13) Uiso 1 1 d . . . H10C H -0.148(3) -0.548(3) 0.0723(13) 0.082(8) Uiso 1 1 d . . . C11 C -0.2032(4) -0.4204(3) 0.20596(18) 0.0674(8) Uani 1 1 d . . . H11B H -0.157(3) -0.372(3) 0.2569(15) 0.084(9) Uiso 1 1 d . . . H11A H -0.312(3) -0.407(3) 0.2011(13) 0.087(9) Uiso 1 1 d . . . H11C H -0.206(3) -0.515(3) 0.2057(12) 0.074(8) Uiso 1 1 d . . . C12 C -0.1377(3) 0.0382(2) 0.11951(12) 0.0446(5) Uani 1 1 d . . . H12A H -0.215(2) -0.039(2) 0.0940(10) 0.046(6) Uiso 1 1 d . . . C13 C -0.1108(4) 0.1455(3) 0.06932(17) 0.0664(8) Uani 1 1 d . . . H13A H -0.033(3) 0.221(3) 0.0936(14) 0.087(10) Uiso 1 1 d . . . H13B H -0.070(3) 0.110(3) 0.0213(15) 0.086(9) Uiso 1 1 d . . . H13C H -0.214(3) 0.180(3) 0.0599(14) 0.094(9) Uiso 1 1 d . . . C14 C -0.1973(3) 0.0927(3) 0.19181(14) 0.0594(7) Uani 1 1 d . . . H14B H -0.124(3) 0.179(3) 0.2134(14) 0.086(9) Uiso 1 1 d . . . H14A H -0.211(3) 0.031(3) 0.2285(14) 0.081(8) Uiso 1 1 d . . . H14C H -0.299(3) 0.117(2) 0.1851(13) 0.082(8) Uiso 1 1 d . . . C21 C 0.2097(2) 0.14463(18) 0.28955(9) 0.0295(4) Uani 1 1 d . . . C22 C 0.1671(2) 0.00346(18) 0.27673(9) 0.0302(4) Uani 1 1 d . . . C23 C 0.0485(2) -0.0579(2) 0.31418(10) 0.0315(4) Uani 1 1 d . . . H23A H 0.0190(17) -0.1502(17) 0.3039(8) 0.022(4) Uiso 1 1 d . . . C24 C -0.0298(2) 0.01744(18) 0.36502(9) 0.0315(4) Uani 1 1 d . . . C25 C 0.0151(2) 0.15663(19) 0.37788(10) 0.0321(4) Uani 1 1 d . . . H25A H -0.0413(18) 0.2103(16) 0.4097(9) 0.024(5) Uiso 1 1 d . . . C26 C 0.1310(2) 0.22280(18) 0.34038(9) 0.0294(4) Uani 1 1 d . . . C31 C 0.2443(2) -0.08539(17) 0.22206(10) 0.0320(4) Uani 1 1 d . . . C32 C 0.3924(2) -0.0990(2) 0.23351(12) 0.0409(5) Uani 1 1 d . . . H32A H 0.446(2) -0.0522(18) 0.2768(10) 0.036(5) Uiso 1 1 d . . . C33 C 0.4643(3) -0.1816(2) 0.18397(13) 0.0486(6) Uani 1 1 d . . . H33A H 0.569(2) -0.1908(18) 0.1947(10) 0.042(6) Uiso 1 1 d . . . C34 C 0.3871(3) -0.2526(2) 0.12262(13) 0.0496(6) Uani 1 1 d . . . H34A H 0.435(2) -0.3059(19) 0.0891(10) 0.039(5) Uiso 1 1 d . . . C35 C 0.2394(3) -0.2420(2) 0.11057(12) 0.0430(5) Uani 1 1 d . . . H35A H 0.188(2) -0.2860(19) 0.0695(11) 0.040(6) Uiso 1 1 d . . . C36 C 0.1658(2) -0.15835(18) 0.15953(10) 0.0339(5) Uani 1 1 d . . . C41 C -0.1641(2) -0.04701(18) 0.40082(10) 0.0334(5) Uani 1 1 d . . . C42 C -0.2697(2) -0.1450(2) 0.36006(13) 0.0424(5) Uani 1 1 d . . . H42A H -0.2517(19) -0.1713(18) 0.3067(10) 0.038(5) Uiso 1 1 d . . . C43 C -0.3978(3) -0.2026(2) 0.39140(14) 0.0521(6) Uani 1 1 d . . . H43A H -0.471(2) -0.270(2) 0.3615(12) 0.060(7) Uiso 1 1 d . . . C44 C -0.4205(3) -0.1647(3) 0.46428(15) 0.0579(7) Uani 1 1 d . . . H44A H -0.508(3) -0.205(2) 0.4851(12) 0.072(8) Uiso 1 1 d . . . C45 C -0.3175(3) -0.0683(2) 0.50602(14) 0.0514(6) Uani 1 1 d . . . H45A H -0.331(2) -0.041(2) 0.5595(13) 0.066(7) Uiso 1 1 d . . . C46 C -0.1899(2) -0.0087(2) 0.47429(11) 0.0397(5) Uani 1 1 d . . . H46A H -0.116(2) 0.060(2) 0.5065(11) 0.047(6) Uiso 1 1 d . . . C51 C 0.1576(2) 0.37397(18) 0.35309(10) 0.0324(4) Uani 1 1 d . . . C52 C 0.1631(2) 0.4432(2) 0.42434(12) 0.0437(5) Uani 1 1 d . . . H52A H 0.160(2) 0.393(2) 0.4649(11) 0.049(6) Uiso 1 1 d . . . C53 C 0.1807(3) 0.5832(2) 0.43686(14) 0.0536(6) Uani 1 1 d . . . H53A H 0.185(2) 0.629(2) 0.4883(12) 0.057(6) Uiso 1 1 d . . . C54 C 0.1948(3) 0.6556(2) 0.37898(15) 0.0558(7) Uani 1 1 d . . . H54A H 0.209(2) 0.749(2) 0.3859(11) 0.063(7) Uiso 1 1 d . . . C55 C 0.1891(2) 0.5894(2) 0.30880(14) 0.0506(6) Uani 1 1 d . . . H55A H 0.198(2) 0.638(2) 0.2667(11) 0.045(6) Uiso 1 1 d . . . C56 C 0.1700(2) 0.4492(2) 0.29585(12) 0.0404(5) Uani 1 1 d . . . H56A H 0.161(2) 0.4054(18) 0.2481(10) 0.038(5) Uiso 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 N1 0.0496(11) 0.0381(10) 0.0337(10) 0.0069(7) 0.0064(8) 0.0035(8) N2 0.0385(11) 0.0559(12) 0.0407(11) 0.0143(9) 0.0017(8) -0.0028(9) N3 0.0488(11) 0.0316(10) 0.0584(12) 0.0030(8) -0.0059(9) 0.0057(8) N4 0.0442(11) 0.0329(10) 0.0420(10) 0.0052(8) -0.0006(8) 0.0094(9) C1 0.0372(11) 0.0266(10) 0.0357(12) 0.0060(8) 0.0050(9) 0.0074(9) C2 0.0568(16) 0.0539(15) 0.0373(13) 0.0109(11) 0.0083(11) 0.0015(12) C3 0.097(12) 0.090(7) 0.073(10) 0.017(6) 0.047(9) 0.021(9) C3A 0.083(10) 0.082(9) 0.036(4) -0.001(5) 0.022(6) -0.001(7) C4 0.114(3) 0.086(2) 0.121(3) 0.065(2) 0.048(2) 0.0244(19) C5 0.0353(12) 0.0432(12) 0.0390(12) 0.0090(10) 0.0036(10) 0.0046(10) C6 0.0586(18) 0.0513(16) 0.074(2) -0.0008(14) -0.0088(15) 0.0065(14) C7 0.0556(16) 0.0664(18) 0.0538(16) 0.0012(14) -0.0077(13) 0.0239(14) C8 0.0485(13) 0.0322(12) 0.0312(11) -0.0005(9) -0.0006(9) 0.0115(10) C9 0.0536(15) 0.0320(12) 0.0647(16) 0.0020(11) -0.0025(12) 0.0078(11) C10 0.108(3) 0.0418(17) 0.081(2) -0.0058(15) 0.000(2) 0.0074(18) C11 0.075(2) 0.0386(16) 0.087(2) 0.0127(14) 0.0097(17) 0.0016(14) C12 0.0495(14) 0.0397(13) 0.0459(13) 0.0048(10) -0.0074(11) 0.0130(11) C13 0.085(2) 0.0648(19) 0.0623(19) 0.0270(15) 0.0084(16) 0.0350(18) C14 0.0557(17) 0.075(2) 0.0536(16) 0.0088(15) 0.0059(13) 0.0287(15) C21 0.0317(10) 0.0310(10) 0.0266(10) 0.0054(8) 0.0009(8) 0.0066(8) C22 0.0328(11) 0.0299(10) 0.0286(10) 0.0055(8) 0.0011(8) 0.0060(9) C23 0.0368(11) 0.0239(11) 0.0334(11) 0.0055(8) 0.0003(9) 0.0022(9) C24 0.0315(11) 0.0346(11) 0.0291(10) 0.0078(8) 0.0005(8) 0.0053(9) C25 0.0319(11) 0.0335(11) 0.0311(11) 0.0017(9) 0.0022(9) 0.0085(9) C26 0.0307(10) 0.0298(10) 0.0280(10) 0.0052(8) -0.0025(8) 0.0052(8) C31 0.0359(11) 0.0252(10) 0.0367(11) 0.0094(8) 0.0059(9) 0.0060(9) C32 0.0419(13) 0.0330(12) 0.0477(14) 0.0051(10) 0.0020(11) 0.0064(10) C33 0.0413(14) 0.0432(13) 0.0655(16) 0.0105(12) 0.0080(12) 0.0170(11) C34 0.0576(16) 0.0434(13) 0.0524(15) 0.0058(11) 0.0219(13) 0.0224(12) C35 0.0564(15) 0.0373(12) 0.0354(13) 0.0014(10) 0.0053(11) 0.0112(11) C36 0.0417(12) 0.0277(10) 0.0338(11) 0.0076(8) 0.0067(9) 0.0073(9) C41 0.0349(11) 0.0300(11) 0.0386(12) 0.0118(9) 0.0032(9) 0.0085(9) C42 0.0435(13) 0.0369(12) 0.0463(14) 0.0076(10) 0.0058(10) 0.0038(10) C43 0.0423(14) 0.0432(14) 0.0680(17) 0.0116(12) 0.0044(12) -0.0043(11) C44 0.0444(14) 0.0626(16) 0.0697(19) 0.0260(14) 0.0192(13) 0.0034(13) C45 0.0502(15) 0.0638(16) 0.0452(15) 0.0189(12) 0.0160(12) 0.0139(12) C46 0.0388(12) 0.0449(13) 0.0382(12) 0.0129(10) 0.0046(10) 0.0089(10) C51 0.0289(10) 0.0291(10) 0.0388(11) 0.0022(9) 0.0007(8) 0.0061(8) C52 0.0461(13) 0.0385(13) 0.0431(13) 0.0001(10) 0.0018(10) 0.0027(10) C53 0.0557(15) 0.0404(14) 0.0580(16) -0.0134(12) -0.0027(12) 0.0065(11) C54 0.0556(15) 0.0274(13) 0.082(2) 0.0005(13) -0.0065(13) 0.0065(11) C55 0.0544(15) 0.0350(13) 0.0648(16) 0.0147(12) -0.0031(12) 0.0082(11) C56 0.0440(13) 0.0342(12) 0.0431(13) 0.0040(10) -0.0003(10) 0.0079(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 C1 1.295(2) . ? N1 C2 1.466(3) . ? N2 C1 1.350(2) . ? N2 C5 1.458(3) . ? N3 C8 1.289(2) . ? N3 C9 1.461(3) . ? N4 C8 1.365(2) . ? N4 C12 1.457(3) . ? C1 C21 1.507(2) . ? C2 C4 1.493(3) . ? C2 C3 1.51(2) . ? C2 C3A 1.523(19) . ? C5 C7 1.512(3) . ? C5 C6 1.527(3) . ? C8 C36 1.507(3) . ? C9 C11 1.513(3) . ? C9 C10 1.526(4) . ? C12 C14 1.508(3) . ? C12 C13 1.518(3) . ? C21 C22 1.402(2) . ? C21 C26 1.411(2) . ? C22 C23 1.389(2) . ? C22 C31 1.505(2) . ? C23 C24 1.393(3) . ? C24 C25 1.385(3) . ? C24 C41 1.487(2) . ? C25 C26 1.392(2) . ? C26 C51 1.492(2) . ? C31 C32 1.385(3) . ? C31 C36 1.401(2) . ? C32 C33 1.386(3) . ? C33 C34 1.374(3) . ? C34 C35 1.375(3) . ? C35 C36 1.395(3) . ? C41 C42 1.390(3) . ? C41 C46 1.391(3) . ? C42 C43 1.378(3) . ? C43 C44 1.374(3) . ? C44 C45 1.377(3) . ? C45 C46 1.385(3) . ? C51 C56 1.385(3) . ? C51 C52 1.398(3) . ? C52 C53 1.384(3) . ? C53 C54 1.377(3) . ? C54 C55 1.370(3) . ? C55 C56 1.385(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 C1 N1 C2 120.18(17) . . ? C1 N2 C5 128.12(18) . . ? C8 N3 C9 120.83(18) . . ? C8 N4 C12 123.01(19) . . ? N1 C1 N2 126.25(17) . . ? N1 C1 C21 114.62(16) . . ? N2 C1 C21 119.13(17) . . ? N1 C2 C4 110.4(2) . . ? N1 C2 C3 109.2(9) . . ? C4 C2 C3 121.9(8) . . ? N1 C2 C3A 107.0(8) . . ? C4 C2 C3A 104.7(7) . . ? C3 C2 C3A 22.3(9) . . ? N2 C5 C7 110.89(18) . . ? N2 C5 C6 109.79(19) . . ? C7 C5 C6 110.2(2) . . ? N3 C8 N4 121.37(19) . . ? N3 C8 C36 127.54(17) . . ? N4 C8 C36 111.09(17) . . ? N3 C9 C11 110.5(2) . . ? N3 C9 C10 107.5(2) . . ? C11 C9 C10 110.4(2) . . ? N4 C12 C14 110.99(18) . . ? N4 C12 C13 108.8(2) . . ? C14 C12 C13 111.6(2) . . ? C22 C21 C26 119.40(16) . . ? C22 C21 C1 118.55(16) . . ? C26 C21 C1 121.76(16) . . ? C23 C22 C21 119.84(17) . . ? C23 C22 C31 118.13(16) . . ? C21 C22 C31 122.02(15) . . ? C22 C23 C24 121.59(18) . . ? C25 C24 C23 117.90(17) . . ? C25 C24 C41 120.42(17) . . ? C23 C24 C41 121.54(17) . . ? C24 C25 C26 122.48(19) . . ? C25 C26 C21 118.75(17) . . ? C25 C26 C51 117.38(17) . . ? C21 C26 C51 123.75(16) . . ? C32 C31 C36 119.01(18) . . ? C32 C31 C22 120.72(17) . . ? C36 C31 C22 120.25(17) . . ? C31 C32 C33 121.3(2) . . ? C34 C33 C32 119.5(2) . . ? C33 C34 C35 120.2(2) . . ? C34 C35 C36 121.0(2) . . ? C35 C36 C31 118.98(19) . . ? C35 C36 C8 120.60(18) . . ? C31 C36 C8 120.32(16) . . ? C42 C41 C46 118.56(18) . . ? C42 C41 C24 119.87(18) . . ? C46 C41 C24 121.54(17) . . ? C43 C42 C41 120.9(2) . . ? C44 C43 C42 119.7(2) . . ? C43 C44 C45 120.6(2) . . ? C44 C45 C46 119.8(2) . . ? C45 C46 C41 120.5(2) . . ? C56 C51 C52 118.27(18) . . ? C56 C51 C26 121.85(18) . . ? C52 C51 C26 119.80(17) . . ? C53 C52 C51 120.5(2) . . ? C54 C53 C52 120.0(2) . . ? C55 C54 C53 120.2(2) . . ? C54 C55 C56 120.0(2) . . ? C51 C56 C55 120.9(2) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.336 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.032 data_jcc21m _database_code_CSD 190139 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C51.50 H66 Cl4 N4' _chemical_formula_weight 882.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 16.300(2) _cell_length_b 15.3088(19) _cell_length_c 20.157(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.115(2) _cell_angle_gamma 90.00 _cell_volume 5009.9(11) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max .2 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1884 _exptl_absorpt_coefficient_mu 0.273 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 14236 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.00 _reflns_number_total 8381 _reflns_number_gt 6985 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1391P)^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 SHELXL _refine_ls_extinction_coef 0.0014(4) _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 -0.04(6) _refine_ls_number_reflns 8381 _refine_ls_number_parameters 551 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1764 _refine_ls_wR_factor_gt 0.1693 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _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 N1 N 0.40852(17) 0.94825(18) 1.03271(14) 0.0286(6) Uani 1 1 d . . . H1A H 0.4125 0.9802 0.9974 0.034 Uiso 1 1 calc R . . N2 N 0.31826(17) 0.88070(18) 1.09804(15) 0.0299(6) Uani 1 1 d . . . H2A H 0.3602 0.8559 1.1202 0.036 Uiso 1 1 calc R . . N3 N 0.41517(18) 1.06398(18) 0.92497(15) 0.0314(6) Uani 1 1 d . . . N4 N 0.4003(2) 1.21278(18) 0.89607(16) 0.0367(7) Uani 1 1 d . . . H4A H 0.4339 1.2115 0.8649 0.044 Uiso 1 1 calc R . . C1 C 0.2638(2) 0.9679(2) 1.00150(17) 0.0270(7) Uani 1 1 d . . . C2 C 0.2578(2) 1.0590(2) 0.99653(17) 0.0278(7) Uani 1 1 d . . . C3 C 0.1925(2) 1.0948(2) 0.95638(18) 0.0303(7) Uani 1 1 d . . . H3B H 0.1884 1.1559 0.9531 0.036 Uiso 1 1 calc R . . C4 C 0.1332(2) 1.0441(2) 0.92085(17) 0.0291(7) Uani 1 1 d . . . C5 C 0.1438(2) 0.9538(2) 0.92451(18) 0.0307(7) Uani 1 1 d . . . H5A H 0.1062 0.9179 0.8992 0.037 Uiso 1 1 calc R . . C6 C 0.2072(2) 0.9148(2) 0.96370(17) 0.0275(7) Uani 1 1 d . . . C7 C 0.33367(19) 0.9288(2) 1.04737(17) 0.0264(7) Uani 1 1 d . . . C8 C 0.3989(2) 1.1431(2) 0.93825(17) 0.0282(7) Uani 1 1 d . . . C11 C 0.3137(2) 1.1217(2) 1.03590(18) 0.0287(7) Uani 1 1 d . . . C12 C 0.3787(2) 1.1636(2) 1.00790(18) 0.0301(7) Uani 1 1 d . . . C13 C 0.4241(2) 1.2271(2) 1.04484(19) 0.0358(8) Uani 1 1 d . . . H13A H 0.4685 1.2546 1.0266 0.043 Uiso 1 1 calc R . . C14 C 0.4047(2) 1.2503(2) 1.1082(2) 0.0386(8) Uani 1 1 d . . . H14A H 0.4361 1.2926 1.1328 0.046 Uiso 1 1 calc R . . C15 C 0.3387(3) 1.2106(2) 1.1347(2) 0.0391(8) Uani 1 1 d . . . H15A H 0.3242 1.2272 1.1771 0.047 Uiso 1 1 calc R . . C16 C 0.2938(2) 1.1463(2) 1.09890(19) 0.0366(8) Uani 1 1 d . . . H16A H 0.2495 1.1191 1.1175 0.044 Uiso 1 1 calc R . . C21 C 0.0605(2) 1.0845(2) 0.88175(19) 0.0348(8) Uani 1 1 d . . . C22 C 0.0309(3) 1.1646(3) 0.8990(2) 0.0427(9) Uani 1 1 d . . . H22A H 0.0565 1.1949 0.9358 0.051 Uiso 1 1 calc R . . C23 C -0.0370(3) 1.2013(3) 0.8619(3) 0.0525(11) Uani 1 1 d . . . H23A H -0.0560 1.2567 0.8738 0.063 Uiso 1 1 calc R . . C24 C -0.0760(3) 1.1591(3) 0.8094(3) 0.0580(13) Uani 1 1 d . . . H24A H -0.1222 1.1844 0.7856 0.070 Uiso 1 1 calc R . . C25 C -0.0470(3) 1.0765(3) 0.7904(2) 0.0527(12) Uani 1 1 d . . . H25A H -0.0732 1.0467 0.7536 0.063 Uiso 1 1 calc R . . C26 C 0.0202(2) 1.0405(3) 0.8267(2) 0.0424(9) Uani 1 1 d . . . H26A H 0.0396 0.9855 0.8145 0.051 Uiso 1 1 calc R . . C31 C 0.2106(2) 0.8170(2) 0.96407(17) 0.0303(7) Uani 1 1 d . . . C32 C 0.1389(2) 0.7700(2) 0.96989(19) 0.0350(8) Uani 1 1 d . . . H32A H 0.0893 0.8002 0.9735 0.042 Uiso 1 1 calc R . . C33 C 0.1386(3) 0.6794(2) 0.9706(2) 0.0418(9) Uani 1 1 d . . . H33A H 0.0893 0.6486 0.9742 0.050 Uiso 1 1 calc R . . C34 C 0.2110(3) 0.6349(3) 0.9659(2) 0.0460(10) Uani 1 1 d . . . H34A H 0.2113 0.5736 0.9676 0.055 Uiso 1 1 calc R . . C35 C 0.2833(3) 0.6793(3) 0.9588(2) 0.0475(10) Uani 1 1 d . . . H35A H 0.3323 0.6484 0.9543 0.057 Uiso 1 1 calc R . . C36 C 0.2833(2) 0.7713(2) 0.9582(2) 0.0366(8) Uani 1 1 d . . . H36A H 0.3326 0.8019 0.9539 0.044 Uiso 1 1 calc R . . C41 C 0.4852(2) 0.9217(2) 1.06952(18) 0.0303(7) Uani 1 1 d . . . H41A H 0.4748 0.9110 1.1165 0.036 Uiso 1 1 calc R . . C42 C 0.5478(2) 0.9958(3) 1.0675(2) 0.0439(9) Uani 1 1 d . . . H42A H 0.5271 1.0477 1.0891 0.053 Uiso 1 1 calc R . . H42B H 0.5547 1.0107 1.0210 0.053 Uiso 1 1 calc R . . C43 C 0.6312(3) 0.9695(3) 1.1029(3) 0.0513(11) Uani 1 1 d . . . H43A H 0.6708 1.0169 1.0989 0.062 Uiso 1 1 calc R . . H43B H 0.6253 0.9605 1.1504 0.062 Uiso 1 1 calc R . . C44 C 0.6638(3) 0.8867(4) 1.0737(3) 0.0633(14) Uani 1 1 d . . . H44A H 0.7157 0.8700 1.0988 0.076 Uiso 1 1 calc R . . H44B H 0.6750 0.8973 1.0274 0.076 Uiso 1 1 calc R . . C45 C 0.6009(3) 0.8117(3) 1.0761(3) 0.0651(14) Uani 1 1 d . . . H45A H 0.6218 0.7596 1.0550 0.078 Uiso 1 1 calc R . . H45B H 0.5937 0.7974 1.1226 0.078 Uiso 1 1 calc R . . C46 C 0.5182(3) 0.8375(3) 1.0405(2) 0.0494(10) Uani 1 1 d . . . H46A H 0.4785 0.7901 1.0447 0.059 Uiso 1 1 calc R . . H46B H 0.5244 0.8459 0.9930 0.059 Uiso 1 1 calc R . . C51 C 0.2363(2) 0.8641(2) 1.12165(18) 0.0325(8) Uani 1 1 d . . . H51A H 0.1939 0.8824 1.0862 0.039 Uiso 1 1 calc R . . C52 C 0.2251(2) 0.7661(2) 1.1346(2) 0.0368(8) Uani 1 1 d . . . H52A H 0.2326 0.7330 1.0939 0.044 Uiso 1 1 calc R . . H52B H 0.2666 0.7464 1.1696 0.044 Uiso 1 1 calc R . . C53 C 0.1389(2) 0.7498(3) 1.1561(2) 0.0466(10) Uani 1 1 d . . . H53A H 0.0980 0.7638 1.1190 0.056 Uiso 1 1 calc R . . H53B H 0.1332 0.6877 1.1666 0.056 Uiso 1 1 calc R . . C54 C 0.1217(3) 0.8036(3) 1.2159(2) 0.0533(11) Uani 1 1 d . . . H54A H 0.1560 0.7823 1.2550 0.064 Uiso 1 1 calc R . . H54B H 0.0639 0.7963 1.2245 0.064 Uiso 1 1 calc R . . C55 C 0.1394(3) 0.9014(3) 1.2058(3) 0.0641(13) Uani 1 1 d . . . H55A H 0.0982 0.9253 1.1723 0.077 Uiso 1 1 calc R . . H55B H 0.1345 0.9326 1.2477 0.077 Uiso 1 1 calc R . . C56 C 0.2240(3) 0.9162(3) 1.1836(2) 0.0509(11) Uani 1 1 d . . . H56A H 0.2656 0.8990 1.2194 0.061 Uiso 1 1 calc R . . H56B H 0.2314 0.9785 1.1746 0.061 Uiso 1 1 calc R . . C61 C 0.4275(2) 1.0366(2) 0.85676(17) 0.0317(7) Uani 1 1 d . . . H61A H 0.4003 1.0794 0.8252 0.038 Uiso 1 1 calc R . . C62 C 0.5191(2) 1.0314(3) 0.84527(19) 0.0393(9) Uani 1 1 d . . . H62A H 0.5438 1.0896 0.8507 0.047 Uiso 1 1 calc R . . H62B H 0.5473 0.9928 0.8788 0.047 Uiso 1 1 calc R . . C63 C 0.5316(3) 0.9967(3) 0.7757(2) 0.0453(10) Uani 1 1 d . . . H63A H 0.5089 1.0386 0.7422 0.054 Uiso 1 1 calc R . . H63B H 0.5906 0.9907 0.7711 0.054 Uiso 1 1 calc R . . C64 C 0.4898(3) 0.9090(3) 0.7636(2) 0.0520(11) Uani 1 1 d . . . H64A H 0.5174 0.8652 0.7932 0.062 Uiso 1 1 calc R . . H64B H 0.4949 0.8907 0.7176 0.062 Uiso 1 1 calc R . . C65 C 0.3986(3) 0.9132(3) 0.7759(2) 0.0543(11) Uani 1 1 d . . . H65A H 0.3696 0.9512 0.7424 0.065 Uiso 1 1 calc R . . H65B H 0.3746 0.8546 0.7709 0.065 Uiso 1 1 calc R . . C66 C 0.3867(3) 0.9478(3) 0.8446(2) 0.0442(9) Uani 1 1 d . . . H66A H 0.4101 0.9062 0.8781 0.053 Uiso 1 1 calc R . . H66B H 0.3276 0.9529 0.8496 0.053 Uiso 1 1 calc R . . C71 C 0.3472(2) 1.2903(2) 0.90109(19) 0.0350(8) Uani 1 1 d . . . H71A H 0.3245 1.2889 0.9450 0.042 Uiso 1 1 calc R . . C72 C 0.3963(3) 1.3745(2) 0.8966(3) 0.0480(10) Uani 1 1 d . . . H72A H 0.4405 1.3764 0.9329 0.058 Uiso 1 1 calc R . . H72B H 0.4216 1.3760 0.8543 0.058 Uiso 1 1 calc R . . C73 C 0.3409(3) 1.4529(3) 0.9011(3) 0.0543(12) Uani 1 1 d . . . H73A H 0.3732 1.5063 0.8966 0.065 Uiso 1 1 calc R . . H73B H 0.3198 1.4539 0.9451 0.065 Uiso 1 1 calc R . . C74 C 0.2680(4) 1.4521(3) 0.8472(3) 0.0630(14) Uani 1 1 d . . . H74A H 0.2317 1.5018 0.8536 0.076 Uiso 1 1 calc R . . H74B H 0.2884 1.4575 0.8031 0.076 Uiso 1 1 calc R . . C75 C 0.2200(3) 1.3667(3) 0.8512(3) 0.0632(13) Uani 1 1 d . . . H75A H 0.1764 1.3645 0.8145 0.076 Uiso 1 1 calc R . . H75B H 0.1938 1.3653 0.8931 0.076 Uiso 1 1 calc R . . C76 C 0.2757(3) 1.2869(3) 0.8475(2) 0.0452(10) Uani 1 1 d . . . H76A H 0.2435 1.2337 0.8531 0.054 Uiso 1 1 calc R . . H76B H 0.2970 1.2846 0.8036 0.054 Uiso 1 1 calc R . . C100 C -0.0493(7) 0.9104(7) 0.6265(6) 0.075(4) Uani 0.50 1 d P . . H10A H -0.0194 0.9201 0.6703 0.090 Uiso 0.50 1 calc PR . . H10B H -0.0659 0.8489 0.6243 0.090 Uiso 0.50 1 calc PR . . C200 C -0.3659(3) 0.7442(4) 0.2833(3) 0.0630(13) Uani 1 1 d . . . H20A H -0.3645 0.7404 0.3319 0.076 Uiso 1 1 calc R . . H20B H -0.4225 0.7578 0.2659 0.076 Uiso 1 1 calc R . . Cl1 Cl 0.43331(5) 0.78590(6) 1.21959(5) 0.0421(2) Uani 1 1 d . . . Cl10 Cl 0.0173(2) 0.9292(2) 0.56618(15) 0.0892(10) Uani 0.50 1 d P . . Cl11 Cl -0.13729(18) 0.9742(2) 0.62092(17) 0.0860(10) Uani 0.50 1 d P . . Cl20 Cl -0.30013(9) 0.82913(10) 0.26189(9) 0.0798(4) Uani 1 1 d . . . Cl21 Cl -0.33769(12) 0.64368(10) 0.25199(10) 0.0928(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0279(14) 0.0287(14) 0.0293(15) 0.0056(11) 0.0028(12) 0.0020(11) N2 0.0258(13) 0.0307(15) 0.0329(16) 0.0082(12) 0.0010(12) 0.0017(11) N3 0.0342(15) 0.0284(15) 0.0320(16) 0.0025(11) 0.0053(13) 0.0001(11) N4 0.0459(18) 0.0249(15) 0.0415(19) 0.0013(12) 0.0164(15) 0.0038(12) C1 0.0251(16) 0.0281(17) 0.0282(17) 0.0029(13) 0.0047(13) 0.0017(12) C2 0.0252(15) 0.0292(17) 0.0302(18) 0.0007(13) 0.0085(14) 0.0001(13) C3 0.0328(17) 0.0251(16) 0.0338(19) 0.0029(13) 0.0074(15) 0.0022(13) C4 0.0276(17) 0.0322(17) 0.0277(18) 0.0061(13) 0.0028(14) 0.0003(12) C5 0.0272(16) 0.0325(18) 0.0320(19) -0.0001(14) 0.0006(14) -0.0026(13) C6 0.0270(16) 0.0263(16) 0.0299(18) 0.0033(13) 0.0066(14) -0.0021(12) C7 0.0274(16) 0.0228(15) 0.0289(18) -0.0023(12) 0.0014(14) 0.0013(12) C8 0.0239(16) 0.0291(17) 0.0313(19) -0.0011(13) 0.0005(14) -0.0009(12) C11 0.0282(16) 0.0275(16) 0.0305(18) 0.0031(13) 0.0034(14) 0.0053(13) C12 0.0302(17) 0.0269(16) 0.0330(19) 0.0017(13) 0.0018(15) 0.0018(13) C13 0.0350(19) 0.0314(18) 0.040(2) 0.0001(15) -0.0005(16) -0.0032(14) C14 0.044(2) 0.0345(19) 0.036(2) -0.0078(15) -0.0023(17) -0.0001(16) C15 0.048(2) 0.039(2) 0.0298(19) -0.0063(15) 0.0008(17) 0.0044(16) C16 0.041(2) 0.0340(18) 0.035(2) 0.0020(15) 0.0060(16) 0.0015(15) C21 0.0300(18) 0.0390(19) 0.036(2) 0.0098(15) 0.0045(15) 0.0006(14) C22 0.041(2) 0.044(2) 0.043(2) 0.0057(17) 0.0041(17) 0.0094(17) C23 0.048(2) 0.050(2) 0.061(3) 0.016(2) 0.016(2) 0.0199(19) C24 0.035(2) 0.069(3) 0.069(3) 0.036(3) -0.005(2) 0.008(2) C25 0.037(2) 0.075(3) 0.043(2) 0.026(2) -0.0101(19) -0.008(2) C26 0.037(2) 0.048(2) 0.042(2) 0.0110(17) 0.0032(17) -0.0023(16) C31 0.0366(18) 0.0282(17) 0.0261(17) -0.0015(13) 0.0019(14) 0.0007(14) C32 0.0354(19) 0.0331(18) 0.036(2) 0.0003(15) 0.0027(15) -0.0036(14) C33 0.048(2) 0.0338(19) 0.043(2) 0.0025(16) 0.0009(18) -0.0128(17) C34 0.062(3) 0.0293(19) 0.048(2) -0.0023(16) 0.009(2) -0.0018(17) C35 0.057(2) 0.0299(19) 0.057(3) -0.0028(17) 0.012(2) 0.0061(17) C36 0.0379(19) 0.0279(17) 0.045(2) 0.0017(15) 0.0083(17) 0.0002(14) C41 0.0276(16) 0.0323(17) 0.0313(18) 0.0045(13) 0.0045(14) -0.0003(13) C42 0.034(2) 0.040(2) 0.056(3) 0.0080(17) -0.0049(18) -0.0050(16) C43 0.032(2) 0.061(3) 0.060(3) 0.013(2) -0.0026(19) -0.0059(18) C44 0.030(2) 0.100(4) 0.059(3) 0.013(3) -0.002(2) 0.017(2) C45 0.056(3) 0.056(3) 0.079(4) -0.010(2) -0.015(3) 0.031(2) C46 0.046(2) 0.041(2) 0.059(3) -0.0072(19) -0.008(2) 0.0125(18) C51 0.0291(17) 0.0366(19) 0.0317(19) 0.0060(14) 0.0026(15) 0.0023(13) C52 0.0323(18) 0.0385(19) 0.040(2) 0.0028(16) 0.0025(16) -0.0081(15) C53 0.037(2) 0.058(3) 0.045(2) 0.0053(19) 0.0045(18) -0.0147(18) C54 0.046(2) 0.070(3) 0.046(3) 0.015(2) 0.019(2) -0.005(2) C55 0.062(3) 0.065(3) 0.071(3) 0.005(2) 0.036(3) 0.008(2) C56 0.060(3) 0.043(2) 0.053(3) -0.0009(19) 0.022(2) -0.0046(19) C61 0.0405(19) 0.0292(17) 0.0255(18) 0.0015(13) 0.0035(15) 0.0042(14) C62 0.038(2) 0.045(2) 0.035(2) 0.0022(16) 0.0046(17) 0.0004(16) C63 0.051(2) 0.048(2) 0.039(2) 0.0048(17) 0.0125(19) 0.0096(18) C64 0.066(3) 0.046(2) 0.045(3) -0.0103(18) 0.010(2) 0.014(2) C65 0.056(3) 0.055(3) 0.051(3) -0.019(2) 0.001(2) -0.007(2) C66 0.047(2) 0.041(2) 0.045(2) -0.0079(17) 0.0052(19) -0.0075(17) C71 0.041(2) 0.0252(17) 0.039(2) 0.0023(14) 0.0056(16) 0.0049(14) C72 0.051(2) 0.029(2) 0.065(3) 0.0018(18) 0.009(2) -0.0015(16) C73 0.071(3) 0.0279(19) 0.066(3) -0.0029(19) 0.019(3) 0.0071(19) C74 0.084(4) 0.042(2) 0.062(3) 0.006(2) 0.002(3) 0.030(2) C75 0.051(3) 0.073(3) 0.062(3) -0.005(2) -0.010(2) 0.023(2) C76 0.050(2) 0.037(2) 0.047(2) -0.0036(17) -0.0008(19) 0.0024(17) C100 0.093(8) 0.056(6) 0.084(8) 0.034(5) 0.059(7) 0.041(5) C200 0.054(3) 0.087(4) 0.049(3) -0.003(2) 0.014(2) 0.009(3) Cl1 0.0351(5) 0.0483(5) 0.0420(5) 0.0035(4) -0.0013(4) -0.0005(4) Cl10 0.140(3) 0.0760(18) 0.0597(16) -0.0098(13) 0.0525(19) -0.0074(18) Cl11 0.0668(16) 0.094(2) 0.090(2) -0.0383(17) -0.0303(16) 0.0306(14) Cl20 0.0612(8) 0.0734(9) 0.1030(11) -0.0154(8) -0.0027(7) -0.0006(6) Cl21 0.1079(13) 0.0643(9) 0.1124(14) 0.0044(8) 0.0444(11) 0.0076(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C7 1.315(4) . ? N1 C41 1.453(4) . ? N2 C7 1.301(4) . ? N2 C51 1.479(4) . ? N3 C8 1.273(4) . ? N3 C61 1.468(5) . ? N4 C8 1.366(5) . ? N4 C71 1.478(4) . ? C1 C2 1.401(5) . ? C1 C6 1.403(5) . ? C1 C7 1.524(4) . ? C2 C3 1.390(5) . ? C2 C11 1.500(5) . ? C3 C4 1.389(5) . ? C4 C5 1.394(5) . ? C4 C21 1.497(5) . ? C5 C6 1.379(5) . ? C6 C31 1.499(5) . ? C8 C12 1.504(5) . ? C11 C16 1.390(5) . ? C11 C12 1.400(5) . ? C12 C13 1.396(5) . ? C13 C14 1.388(6) . ? C14 C15 1.384(6) . ? C15 C16 1.390(5) . ? C21 C22 1.374(5) . ? C21 C26 1.410(6) . ? C22 C23 1.397(6) . ? C23 C24 1.350(8) . ? C24 C25 1.415(7) . ? C25 C26 1.377(6) . ? C31 C32 1.386(5) . ? C31 C36 1.391(5) . ? C32 C33 1.388(5) . ? C33 C34 1.373(6) . ? C34 C35 1.379(7) . ? C35 C36 1.409(5) . ? C41 C46 1.534(5) . ? C41 C42 1.528(5) . ? C42 C43 1.533(6) . ? C43 C44 1.514(8) . ? C44 C45 1.543(8) . ? C45 C46 1.521(6) . ? C51 C56 1.510(6) . ? C51 C52 1.536(5) . ? C52 C53 1.527(5) . ? C53 C54 1.508(7) . ? C54 C55 1.542(7) . ? C55 C56 1.504(6) . ? C61 C66 1.525(5) . ? C61 C62 1.535(5) . ? C62 C63 1.529(6) . ? C63 C64 1.516(6) . ? C64 C65 1.529(7) . ? C65 C66 1.513(6) . ? C71 C76 1.517(6) . ? C71 C72 1.525(5) . ? C72 C73 1.509(6) . ? C73 C74 1.538(7) . ? C74 C75 1.529(8) . ? C75 C76 1.528(6) . ? C100 Cl10 1.726(10) . ? C100 Cl11 1.730(10) . ? C200 Cl21 1.740(6) . ? C200 Cl20 1.763(6) . ? 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 C41 126.5(3) . . ? C7 N2 C51 126.3(3) . . ? C8 N3 C61 121.1(3) . . ? C8 N4 C71 122.9(3) . . ? C2 C1 C6 120.0(3) . . ? C2 C1 C7 118.6(3) . . ? C6 C1 C7 121.4(3) . . ? C3 C2 C1 118.6(3) . . ? C3 C2 C11 116.9(3) . . ? C1 C2 C11 124.3(3) . . ? C2 C3 C4 122.8(3) . . ? C3 C4 C5 116.7(3) . . ? C3 C4 C21 121.5(3) . . ? C5 C4 C21 121.8(3) . . ? C6 C5 C4 122.9(3) . . ? C5 C6 C1 118.9(3) . . ? C5 C6 C31 117.4(3) . . ? C1 C6 C31 123.7(3) . . ? N2 C7 N1 123.5(3) . . ? N2 C7 C1 120.8(3) . . ? N1 C7 C1 115.6(3) . . ? N3 C8 N4 126.7(3) . . ? N3 C8 C12 117.5(3) . . ? N4 C8 C12 115.8(3) . . ? C16 C11 C12 119.4(3) . . ? C16 C11 C2 118.5(3) . . ? C12 C11 C2 121.7(3) . . ? C13 C12 C11 119.2(3) . . ? C13 C12 C8 119.6(3) . . ? C11 C12 C8 121.2(3) . . ? C14 C13 C12 121.0(3) . . ? C15 C14 C13 119.5(3) . . ? C14 C15 C16 120.0(4) . . ? C15 C16 C11 120.8(4) . . ? C22 C21 C26 118.5(3) . . ? C22 C21 C4 121.0(4) . . ? C26 C21 C4 120.5(3) . . ? C21 C22 C23 120.2(4) . . ? C24 C23 C22 121.5(4) . . ? C23 C24 C25 119.7(4) . . ? C26 C25 C24 119.0(4) . . ? C25 C26 C21 121.2(4) . . ? C32 C31 C36 118.6(3) . . ? C32 C31 C6 119.2(3) . . ? C36 C31 C6 122.2(3) . . ? C31 C32 C33 121.6(4) . . ? C34 C33 C32 119.4(4) . . ? C33 C34 C35 120.7(4) . . ? C34 C35 C36 119.6(4) . . ? C31 C36 C35 120.1(4) . . ? N1 C41 C46 110.8(3) . . ? N1 C41 C42 108.9(3) . . ? C46 C41 C42 110.9(3) . . ? C41 C42 C43 111.0(3) . . ? C44 C43 C42 111.5(4) . . ? C43 C44 C45 110.7(4) . . ? C46 C45 C44 110.8(4) . . ? C45 C46 C41 111.3(4) . . ? N2 C51 C56 111.5(3) . . ? N2 C51 C52 110.3(3) . . ? C56 C51 C52 110.4(3) . . ? C53 C52 C51 109.5(3) . . ? C54 C53 C52 112.3(3) . . ? C53 C54 C55 112.0(4) . . ? C56 C55 C54 111.9(4) . . ? C55 C56 C51 111.0(4) . . ? N3 C61 C66 108.1(3) . . ? N3 C61 C62 111.9(3) . . ? C66 C61 C62 110.2(3) . . ? C63 C62 C61 111.5(3) . . ? C64 C63 C62 111.2(3) . . ? C63 C64 C65 111.4(3) . . ? C66 C65 C64 111.7(4) . . ? C65 C66 C61 111.7(4) . . ? N4 C71 C76 110.0(3) . . ? N4 C71 C72 111.1(3) . . ? C76 C71 C72 111.2(3) . . ? C73 C72 C71 110.4(4) . . ? C72 C73 C74 112.3(4) . . ? C75 C74 C73 109.7(4) . . ? C74 C75 C76 111.8(4) . . ? C71 C76 C75 111.1(3) . . ? Cl10 C100 Cl11 115.5(6) . . ? Cl21 C200 Cl20 112.2(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A Cl1 0.87 2.48 3.287(3) 154.4 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.968 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.085