Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author 'Stephen J Connon' _publ_contact_author_email connons@tcd.ie loop_ _publ_author_name "Ciaran O'Dalaigh" S.J.Hynes "John E.O'Brian" 'Thomas McCabe' 'Declan Maher' ; G.W.Watson ; 'Stephen L. Connon' _publ_contact_author_name 'Stephen J Connon' data_cod1m _database_code_depnum_ccdc_archive 'CCDC 293598' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 6-Bn _chemical_melting_point 435-437k _chemical_formula_moiety ? _chemical_formula_sum 'C36 H40 Br Cl4 N3 O2' _chemical_formula_weight 768.45 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ORTHORHOMBIC _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.7318(13) _cell_length_b 18.078(2) _cell_length_c 20.751(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3650.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 396(2) _cell_measurement_reflns_used 36703 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 1.4540 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.836663 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 396(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 'Bruker Smart Apex' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28680 _diffrn_reflns_av_R_equivalents 0.0676 _diffrn_reflns_av_sigmaI/netI 0.0591 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6441 _reflns_number_gt 5570 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker Saint' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker Shelxtl' _computing_publication_material 'Bruker Shelxtl' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0431P)^2^+12.9530P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration ad loop_ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.065(17) _refine_ls_number_reflns 6441 _refine_ls_number_parameters 415 _refine_ls_number_restraints 276 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0777 _refine_ls_wR_factor_ref 0.1840 _refine_ls_wR_factor_gt 0.1786 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.149 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.44680(9) 0.48383(4) 0.26100(4) 0.0541(3) Uani 1 1 d . . . C1 C 0.9820(9) 0.7464(4) 0.2019(4) 0.048(2) Uani 1 1 d . . . H1 H 0.9624 0.7904 0.2233 0.058 Uiso 1 1 calc R . . C2 C 0.9044(8) 0.6838(4) 0.2145(4) 0.0393(18) Uani 1 1 d . . . H2 H 0.8325 0.6856 0.2440 0.047 Uiso 1 1 calc R . . C3 C 0.9352(9) 0.6181(4) 0.1827(4) 0.0375(17) Uani 1 1 d . . . C4 C 1.0437(11) 0.6161(4) 0.1405(4) 0.056(2) Uani 1 1 d . . . H3 H 1.0671 0.5719 0.1203 0.067 Uiso 1 1 calc R . . C5 C 1.1197(10) 0.6810(4) 0.1278(4) 0.051(2) Uani 1 1 d . . . H4 H 1.1920 0.6799 0.0985 0.061 Uiso 1 1 calc R . . C6 C 1.0877(9) 0.7439(4) 0.1581(4) 0.046(2) Uani 1 1 d . . . H5 H 1.1376 0.7866 0.1494 0.055 Uiso 1 1 calc R . . C7 C 1.0403(7) 0.4917(3) 0.2634(4) 0.0380(16) Uani 1 1 d . . . H6 H 1.0993 0.5012 0.2291 0.046 Uiso 1 1 calc R . . C8 C 0.9016(7) 0.5127(3) 0.2598(3) 0.0327(14) Uani 1 1 d . . . C9 C 0.8174(9) 0.5014(4) 0.3116(4) 0.046(2) Uani 1 1 d . . . H7 H 0.7259 0.5162 0.3096 0.055 Uiso 1 1 calc R . . C10 C 0.8684(11) 0.4675(4) 0.3681(4) 0.054(2) Uani 1 1 d . . . H8 H 0.8114 0.4604 0.4035 0.065 Uiso 1 1 calc R . . C11 C 1.0046(9) 0.4449(4) 0.3701(4) 0.0405(18) Uani 1 1 d . . . H9 H 1.0390 0.4217 0.4067 0.049 Uiso 1 1 calc R . . C12 C 1.0883(8) 0.4569(4) 0.3180(4) 0.0371(17) Uani 1 1 d . . . H10 H 1.1793 0.4413 0.3195 0.045 Uiso 1 1 calc R . . C13 C 0.8472(8) 0.5497(3) 0.1982(3) 0.0324(16) Uani 1 1 d . . . C14 C 0.8476(8) 0.4956(3) 0.1402(3) 0.0339(17) Uani 1 1 d . . . H11 H 0.9421 0.4801 0.1310 0.041 Uiso 1 1 calc R . . C15 C 0.7831(10) 0.5273(4) 0.0798(4) 0.049(2) Uani 1 1 d . . . H12 H 0.7617 0.5789 0.0857 0.059 Uiso 1 1 d R . . H13 H 0.8543 0.5295 0.0472 0.059 Uiso 1 1 d R . . C17 C 0.6364(9) 0.4289(4) 0.1143(4) 0.0421(19) Uani 1 1 d . . . H14 H 0.6251 0.3819 0.0928 0.051 Uiso 1 1 d R . . H15 H 0.5558 0.4389 0.1399 0.051 Uiso 1 1 d R . . C18 C 0.8247(8) 0.3672(3) 0.1744(3) 0.0290(15) Uani 1 1 d . . . C19 C 0.6319(8) 0.3113(4) 0.2312(3) 0.0358(16) Uani 1 1 d . . . H16 H 0.6065 0.3594 0.2420 0.043 Uiso 1 1 calc R . . C20 C 0.7366(9) 0.3014(3) 0.1877(3) 0.0336(16) Uani 1 1 d . . . C21 C 0.7066(10) 0.1696(4) 0.2046(4) 0.049(2) Uani 1 1 d . . . H17 H 0.7309 0.1205 0.1972 0.058 Uiso 1 1 calc R . . C22 C 0.6054(9) 0.1848(4) 0.2460(5) 0.057(2) Uani 1 1 d . . . H18 H 0.5612 0.1460 0.2668 0.069 Uiso 1 1 calc R . . C23 C 0.9178(13) 0.1360(4) 0.1126(4) 0.067(3) Uani 1 1 d . . . H19 H 0.9565 0.1137 0.1511 0.080 Uiso 1 1 calc R . . H20 H 0.8438 0.1048 0.0970 0.080 Uiso 1 1 calc R . . C24 C 1.0242(15) 0.1459(5) 0.0627(5) 0.084(4) Uani 1 1 d . . . H21 H 1.0302 0.1024 0.0354 0.101 Uiso 1 1 calc R . . H22 H 1.1133 0.1547 0.0822 0.101 Uiso 1 1 calc R . . C25 C 0.9788(14) 0.2116(5) 0.0247(4) 0.074(4) Uani 1 1 d . . . H23 H 0.9070 0.1986 -0.0057 0.089 Uiso 1 1 calc R . . H24 H 1.0550 0.2339 0.0017 0.089 Uiso 1 1 calc R . . C26 C 0.9241(10) 0.2634(4) 0.0781(4) 0.050(2) Uani 1 1 d . . . H25 H 0.9976 0.2929 0.0964 0.060 Uiso 1 1 calc R . . H26 H 0.8533 0.2961 0.0615 0.060 Uiso 1 1 calc R . . C27 C 0.4533(10) 0.2686(5) 0.3062(4) 0.054(2) Uani 1 1 d . . . H27 H 0.4171 0.3180 0.2998 0.065 Uiso 1 1 calc R . . H28 H 0.3794 0.2338 0.2980 0.065 Uiso 1 1 calc R . . C28 C 0.7789(9) 0.2274(3) 0.1710(3) 0.0357(18) Uani 1 1 d . . . C29 C 0.668(2) 0.4858(9) 0.0677(8) 0.144(6) Uani 1 1 d U . . H29 H 0.6779 0.4625 0.0258 0.173 Uiso 1 1 calc R . . H30 H 0.5894 0.5190 0.0651 0.173 Uiso 1 1 calc R . . C30 C 0.5814(13) 0.3115(5) 0.4034(5) 0.076(4) Uani 1 1 d . . . H31 H 0.6107 0.3525 0.3801 0.091 Uiso 1 1 calc R . . C31 C 0.4967(9) 0.2611(6) 0.3735(5) 0.059(2) Uani 1 1 d . . . C32 C 0.4689(14) 0.1942(10) 0.4052(6) 0.133(7) Uani 1 1 d . . . H32 H 0.4253 0.1551 0.3845 0.159 Uiso 1 1 calc R . . C33 C 0.6239(16) 0.3042(8) 0.4652(6) 0.097(4) Uani 1 1 d U . . H33 H 0.6770 0.3404 0.4850 0.117 Uiso 1 1 calc R . . C34 C 0.5100(19) 0.1892(11) 0.4692(8) 0.138(6) Uani 1 1 d U . . H34 H 0.4838 0.1482 0.4933 0.166 Uiso 1 1 calc R . . C35 C 0.5861(16) 0.2419(9) 0.4971(6) 0.100(4) Uani 1 1 d U . . H35 H 0.6140 0.2356 0.5396 0.120 Uiso 1 1 calc R . . C36 C 0.530(3) 0.0138(15) 0.0727(9) 0.201(11) Uani 1 1 d . . . H36 H 0.5520 0.0086 0.1159 0.242 Uiso 1 1 d R . . H37 H 0.4581 -0.0115 0.0877 0.242 Uiso 1 1 d R . . C37 C 0.2580(12) 0.3574(6) 0.1609(5) 0.071(3) Uani 1 1 d . . . H38 H 0.3174 0.3815 0.1920 0.085 Uiso 1 1 calc R . . H39 H 0.1676 0.3520 0.1800 0.085 Uiso 1 1 calc R . . Cl1 Cl 0.2466(4) 0.4127(2) 0.08901(15) 0.0934(10) Uani 1 1 d . . . Cl2 Cl 0.3247(3) 0.26997(18) 0.14129(13) 0.0817(8) Uani 1 1 d . . . Cl3 Cl 0.4941(7) 0.0997(3) 0.0526(2) 0.153(2) Uani 1 1 d U . . Cl4 Cl 0.6498(7) -0.0320(3) 0.0320(2) 0.1509(19) Uani 1 1 d U . . N1 N 0.5653(7) 0.2553(3) 0.2587(3) 0.0444(14) Uani 1 1 d . . . N2 N 0.8674(8) 0.2118(3) 0.1262(3) 0.0428(17) Uani 1 1 d . . . N3 N 0.7623(7) 0.4300(3) 0.1531(3) 0.0315(13) Uani 1 1 d . . . O1 O 0.7093(5) 0.5776(2) 0.2065(2) 0.0381(12) Uani 1 1 d . . . H40 H 0.6605 0.5451 0.2209 0.046 Uiso 1 1 d R . . O2 O 0.9475(6) 0.3636(2) 0.1855(2) 0.0370(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0561(5) 0.0296(3) 0.0766(6) -0.0126(4) 0.0251(5) -0.0033(4) C1 0.067(6) 0.019(3) 0.059(5) -0.008(3) -0.011(4) -0.009(3) C2 0.053(5) 0.025(3) 0.040(4) -0.007(3) 0.002(3) -0.006(3) C3 0.053(5) 0.023(3) 0.036(4) 0.004(3) 0.003(4) 0.002(3) C4 0.085(7) 0.022(3) 0.059(5) -0.002(3) 0.030(5) -0.009(4) C5 0.065(6) 0.039(4) 0.049(5) 0.005(4) 0.009(4) -0.025(4) C6 0.061(6) 0.027(4) 0.050(5) 0.017(3) -0.013(4) -0.020(4) C7 0.049(4) 0.017(3) 0.048(4) -0.008(3) 0.015(4) 0.004(3) C8 0.052(4) 0.018(3) 0.028(3) -0.008(3) 0.007(3) -0.010(3) C9 0.048(5) 0.054(5) 0.036(4) 0.006(4) 0.001(3) -0.001(4) C10 0.075(7) 0.047(5) 0.041(5) 0.011(4) 0.014(4) -0.012(4) C11 0.060(5) 0.031(4) 0.031(4) 0.007(3) -0.003(4) -0.007(3) C12 0.036(4) 0.028(3) 0.047(4) 0.002(3) 0.003(3) -0.004(3) C13 0.044(4) 0.018(3) 0.035(4) 0.000(3) 0.011(3) 0.001(3) C14 0.057(5) 0.006(3) 0.038(4) 0.001(2) 0.016(3) -0.002(3) C15 0.082(6) 0.024(4) 0.041(4) 0.006(3) 0.008(4) -0.002(4) C17 0.057(5) 0.030(4) 0.039(4) 0.002(3) -0.005(4) 0.013(3) C18 0.040(4) 0.010(3) 0.036(4) -0.005(3) 0.007(3) 0.005(3) C19 0.048(4) 0.027(3) 0.033(4) 0.004(3) 0.006(4) -0.003(3) C20 0.058(5) 0.018(3) 0.025(3) 0.005(3) -0.005(4) -0.005(3) C21 0.073(6) 0.015(3) 0.058(5) 0.009(3) -0.003(5) -0.009(4) C22 0.067(6) 0.031(4) 0.074(7) 0.011(4) -0.006(5) -0.023(4) C23 0.130(10) 0.020(4) 0.049(5) -0.008(3) -0.005(6) 0.021(5) C24 0.147(12) 0.059(6) 0.047(5) -0.021(4) 0.002(7) 0.050(7) C25 0.133(11) 0.053(5) 0.036(5) -0.008(4) 0.011(6) 0.039(6) C26 0.074(6) 0.029(4) 0.048(5) -0.008(3) -0.001(4) 0.012(4) C27 0.048(5) 0.066(5) 0.048(5) 0.021(4) 0.003(4) -0.009(5) C28 0.070(5) 0.015(3) 0.022(3) 0.003(3) -0.007(3) -0.002(3) C29 0.180(10) 0.116(8) 0.137(9) 0.034(8) -0.064(8) -0.052(8) C30 0.123(11) 0.053(5) 0.051(6) -0.022(4) -0.006(6) 0.034(6) C31 0.043(5) 0.074(6) 0.061(6) 0.006(5) 0.007(4) -0.009(4) C32 0.090(10) 0.220(17) 0.088(9) 0.108(11) -0.039(8) -0.092(11) C33 0.119(8) 0.096(7) 0.077(7) -0.038(6) 0.004(6) 0.014(6) C34 0.139(10) 0.159(10) 0.116(9) 0.053(8) 0.014(8) -0.043(8) C35 0.107(8) 0.131(8) 0.062(6) 0.012(6) 0.006(6) 0.007(7) C36 0.22(3) 0.27(3) 0.109(14) -0.013(18) -0.011(16) 0.04(3) C37 0.062(6) 0.091(8) 0.060(6) -0.021(5) -0.001(5) 0.000(6) Cl1 0.093(2) 0.108(2) 0.0799(19) 0.0053(17) -0.0003(18) 0.0261(19) Cl2 0.088(2) 0.098(2) 0.0588(15) 0.0017(15) 0.0028(14) -0.0022(17) Cl3 0.227(6) 0.120(3) 0.110(3) 0.012(3) -0.025(3) -0.013(4) Cl4 0.217(5) 0.130(3) 0.106(3) 0.021(3) -0.015(3) -0.038(4) N1 0.048(4) 0.047(3) 0.038(3) 0.009(3) 0.003(3) -0.010(3) N2 0.085(5) 0.016(3) 0.028(3) -0.004(2) -0.007(3) 0.012(3) N3 0.045(4) 0.019(3) 0.030(3) -0.001(2) 0.003(3) -0.001(3) O1 0.048(3) 0.019(2) 0.047(3) -0.008(2) 0.006(2) 0.000(2) O2 0.048(3) 0.015(2) 0.049(3) 0.0044(19) 0.006(3) 0.000(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 C1 C6 1.374(12) . ? C1 C2 1.385(10) . ? C1 H1 0.9300 . ? C2 C3 1.392(10) . ? C2 H2 0.9300 . ? C3 C4 1.371(12) . ? C3 C13 1.537(10) . ? C4 C5 1.412(11) . ? C4 H3 0.9300 . ? C5 C6 1.337(12) . ? C5 H4 0.9300 . ? C6 H5 0.9300 . ? C7 C12 1.378(10) . ? C7 C8 1.404(10) . ? C7 H6 0.9300 . ? C8 C9 1.366(10) . ? C8 C13 1.538(10) . ? C9 C10 1.414(11) . ? C9 H7 0.9300 . ? C10 C11 1.387(13) . ? C10 H8 0.9300 . ? C11 C12 1.372(11) . ? C11 H9 0.9300 . ? C12 H10 0.9300 . ? C13 O1 1.445(9) . ? C13 C14 1.550(9) . ? C14 N3 1.472(8) . ? C14 C15 1.515(11) . ? C14 H11 0.9800 . ? C15 C29 1.376(17) . ? C15 H12 0.9646 . ? C15 H13 0.9692 . ? C17 C29 1.443(17) . ? C17 N3 1.466(10) . ? C17 H14 0.9664 . ? C17 H15 0.9647 . ? C18 O2 1.219(9) . ? C18 N3 1.362(8) . ? C18 C20 1.491(9) . ? C19 N1 1.331(9) . ? C19 C20 1.374(11) . ? C19 H16 0.9300 . ? C20 C28 1.442(9) . ? C21 C22 1.336(12) . ? C21 C28 1.439(10) . ? C21 H17 0.9300 . ? C22 N1 1.359(10) . ? C22 H18 0.9300 . ? C23 C24 1.476(16) . ? C23 N2 1.482(9) . ? C23 H19 0.9700 . ? C23 H20 0.9700 . ? C24 C25 1.492(13) . ? C24 H21 0.9700 . ? C24 H22 0.9700 . ? C25 C26 1.545(11) . ? C25 H23 0.9700 . ? C25 H24 0.9700 . ? C26 N2 1.473(10) . ? C26 H25 0.9700 . ? C26 H26 0.9700 . ? C27 C31 1.464(13) . ? C27 N1 1.490(11) . ? C27 H27 0.9700 . ? C27 H28 0.9700 . ? C28 N2 1.299(10) . ? C29 H29 0.9700 . ? C29 H30 0.9700 . ? C30 C33 1.354(16) . ? C30 C31 1.377(14) . ? C30 H31 0.9300 . ? C31 C32 1.404(15) . ? C32 C34 1.39(2) . ? C32 H32 0.9300 . ? C33 C35 1.36(2) . ? C33 H33 0.9300 . ? C34 C35 1.34(2) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 Cl3 1.65(3) . ? C36 Cl4 1.66(2) . ? C36 H36 0.9264 . ? C36 H37 0.8914 . ? C37 Cl2 1.756(11) . ? C37 Cl1 1.799(11) . ? C37 H38 0.9700 . ? C37 H39 0.9700 . ? O1 H40 0.8116 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 120.4(7) . . ? C6 C1 H1 119.8 . . ? C2 C1 H1 119.8 . . ? C1 C2 C3 119.4(8) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 119.4(7) . . ? C4 C3 C13 122.7(6) . . ? C2 C3 C13 117.8(7) . . ? C3 C4 C5 120.0(7) . . ? C3 C4 H3 120.0 . . ? C5 C4 H3 120.0 . . ? C6 C5 C4 119.8(8) . . ? C6 C5 H4 120.1 . . ? C4 C5 H4 120.1 . . ? C5 C6 C1 120.9(7) . . ? C5 C6 H5 119.5 . . ? C1 C6 H5 119.5 . . ? C12 C7 C8 119.5(7) . . ? C12 C7 H6 120.2 . . ? C8 C7 H6 120.2 . . ? C9 C8 C7 119.7(7) . . ? C9 C8 C13 120.8(6) . . ? C7 C8 C13 119.5(6) . . ? C8 C9 C10 120.4(8) . . ? C8 C9 H7 119.8 . . ? C10 C9 H7 119.8 . . ? C11 C10 C9 119.2(8) . . ? C11 C10 H8 120.4 . . ? C9 C10 H8 120.4 . . ? C12 C11 C10 119.8(7) . . ? C12 C11 H9 120.1 . . ? C10 C11 H9 120.1 . . ? C11 C12 C7 121.3(7) . . ? C11 C12 H10 119.4 . . ? C7 C12 H10 119.4 . . ? O1 C13 C3 105.2(5) . . ? O1 C13 C8 111.8(5) . . ? C3 C13 C8 109.4(6) . . ? O1 C13 C14 108.4(6) . . ? C3 C13 C14 110.1(5) . . ? C8 C13 C14 111.7(5) . . ? N3 C14 C15 102.7(6) . . ? N3 C14 C13 111.5(5) . . ? C15 C14 C13 113.7(5) . . ? N3 C14 H11 109.6 . . ? C15 C14 H11 109.6 . . ? C13 C14 H11 109.6 . . ? C29 C15 C14 106.5(8) . . ? C29 C15 H12 112.0 . . ? C14 C15 H12 110.4 . . ? C29 C15 H13 118.7 . . ? C14 C15 H13 107.3 . . ? H12 C15 H13 101.8 . . ? C29 C17 N3 100.5(9) . . ? C29 C17 H14 109.9 . . ? N3 C17 H14 111.1 . . ? C29 C17 H15 114.1 . . ? N3 C17 H15 112.0 . . ? H14 C17 H15 109.1 . . ? O2 C18 N3 122.9(6) . . ? O2 C18 C20 119.0(6) . . ? N3 C18 C20 118.0(7) . . ? N1 C19 C20 122.9(6) . . ? N1 C19 H16 118.5 . . ? C20 C19 H16 118.5 . . ? C19 C20 C28 119.4(6) . . ? C19 C20 C18 116.3(6) . . ? C28 C20 C18 122.1(7) . . ? C22 C21 C28 121.5(7) . . ? C22 C21 H17 119.3 . . ? C28 C21 H17 119.3 . . ? C21 C22 N1 122.0(7) . . ? C21 C22 H18 119.0 . . ? N1 C22 H18 119.0 . . ? C24 C23 N2 104.6(7) . . ? C24 C23 H19 110.8 . . ? N2 C23 H19 110.8 . . ? C24 C23 H20 110.8 . . ? N2 C23 H20 110.8 . . ? H19 C23 H20 108.9 . . ? C23 C24 C25 105.0(9) . . ? C23 C24 H21 110.7 . . ? C25 C24 H21 110.7 . . ? C23 C24 H22 110.7 . . ? C25 C24 H22 110.7 . . ? H21 C24 H22 108.8 . . ? C24 C25 C26 101.9(7) . . ? C24 C25 H23 111.4 . . ? C26 C25 H23 111.4 . . ? C24 C25 H24 111.4 . . ? C26 C25 H24 111.4 . . ? H23 C25 H24 109.2 . . ? N2 C26 C25 103.3(6) . . ? N2 C26 H25 111.1 . . ? C25 C26 H25 111.1 . . ? N2 C26 H26 111.1 . . ? C25 C26 H26 111.1 . . ? H25 C26 H26 109.1 . . ? C31 C27 N1 113.9(8) . . ? C31 C27 H27 108.8 . . ? N1 C27 H27 108.8 . . ? C31 C27 H28 108.8 . . ? N1 C27 H28 108.8 . . ? H27 C27 H28 107.7 . . ? N2 C28 C21 120.8(6) . . ? N2 C28 C20 124.3(6) . . ? C21 C28 C20 114.7(7) . . ? C15 C29 C17 116.0(12) . . ? C15 C29 H29 108.3 . . ? C17 C29 H29 108.3 . . ? C15 C29 H30 108.3 . . ? C17 C29 H30 108.3 . . ? H29 C29 H30 107.4 . . ? C33 C30 C31 123.0(12) . . ? C33 C30 H31 118.5 . . ? C31 C30 H31 118.5 . . ? C30 C31 C32 118.3(10) . . ? C30 C31 C27 122.8(9) . . ? C32 C31 C27 118.1(10) . . ? C34 C32 C31 116.7(15) . . ? C34 C32 H32 121.7 . . ? C31 C32 H32 121.7 . . ? C30 C33 C35 117.4(13) . . ? C30 C33 H33 121.3 . . ? C35 C33 H33 121.3 . . ? C35 C34 C32 121.8(15) . . ? C35 C34 H34 119.1 . . ? C32 C34 H34 119.1 . . ? C34 C35 C33 122.0(14) . . ? C34 C35 H35 119.0 . . ? C33 C35 H35 119.0 . . ? Cl3 C36 Cl4 119.3(15) . . ? Cl3 C36 H36 112.9 . . ? Cl4 C36 H36 106.2 . . ? Cl3 C36 H37 114.0 . . ? Cl4 C36 H37 118.2 . . ? H36 C36 H37 78.0 . . ? Cl2 C37 Cl1 109.3(5) . . ? Cl2 C37 H38 109.8 . . ? Cl1 C37 H38 109.8 . . ? Cl2 C37 H39 109.8 . . ? Cl1 C37 H39 109.8 . . ? H38 C37 H39 108.3 . . ? C19 N1 C22 119.4(7) . . ? C19 N1 C27 121.2(6) . . ? C22 N1 C27 119.3(7) . . ? C28 N2 C26 126.5(6) . . ? C28 N2 C23 123.8(7) . . ? C26 N2 C23 109.5(7) . . ? C18 N3 C17 122.7(6) . . ? C18 N3 C14 118.6(6) . . ? C17 N3 C14 112.5(6) . . ? C13 O1 H40 109.6 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.883 _refine_diff_density_min -0.580 _refine_diff_density_rms 0.094