# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Junk, Peter Courtney' 'Cole, Marcus L.' 'Jones, Cameron' _publ_contact_author_name 'Dr Peter Courtney Junk' _publ_contact_author_address ; School of Chemistry Monash University Box 23 Clayton Victoria 3800 AUSTRALIA ; _publ_contact_author_email 'PETER.JUNK@SCI.MONASH.EDU.AU' _publ_section_title ; Studies of the reactivity of N-heterocyclic carbenes with halogen and halide sources ; data_compound1 _database_code_CSD 185383 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 Cl2 N2.50' _chemical_formula_weight 394.34 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 P21/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 10.242(4) _cell_length_b 17.141(6) _cell_length_c 16.496(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.767(8) _cell_angle_gamma 90.00 _cell_volume 2844.9(17) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.921 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 830 _exptl_absorpt_coefficient_mu 0.235 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9328 _exptl_absorpt_correction_T_max 0.9545 _exptl_absorpt_process_details 'SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 13164 _diffrn_reflns_av_R_equivalents 0.0678 _diffrn_reflns_av_sigmaI/netI 0.0670 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 23.25 _reflns_number_total 4212 _reflns_number_gt 2149 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.1253P)^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_number_reflns 4212 _refine_ls_number_parameters 253 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1278 _refine_ls_R_factor_gt 0.0759 _refine_ls_wR_factor_ref 0.2256 _refine_ls_wR_factor_gt 0.1946 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.32684(15) 0.06556(8) 0.27887(8) 0.0883(5) Uani 1 1 d . . . N1 N 0.1744(4) -0.0464(2) 0.1972(2) 0.0624(10) Uani 1 1 d . . . C1 C 0.2226(4) -0.0108(2) 0.2677(3) 0.0616(12) Uani 1 1 d . . . Cl2 Cl 0.0037(2) 0.2500 0.93283(11) 0.0904(7) Uani 1 2 d S . . N2 N 0.1756(4) -0.0454(2) 0.3284(2) 0.0655(10) Uani 1 1 d . . . C2 C 0.0948(5) -0.1075(3) 0.2145(3) 0.0723(13) Uani 1 1 d . . . H2 H 0.0488 -0.1424 0.1764 0.087 Uiso 1 1 calc R . . Cl3 Cl -0.0133(2) 0.2500 0.57136(11) 0.0866(6) Uani 1 2 d S . . N3 N 0.4333(15) 0.2500 -0.0118(8) 0.126(5) Uiso 0.50 2 d SPD . . C3 C 0.0962(5) -0.1072(3) 0.2959(3) 0.0725(13) Uani 1 1 d . . . H3 H 0.0521 -0.1419 0.3248 0.087 Uiso 1 1 calc R . . N4 N 0.2852(15) 0.2500 0.4862(9) 0.114(4) Uiso 0.50 2 d SPD . . C4 C 0.2056(5) -0.0252(3) 0.1180(3) 0.0652(12) Uani 1 1 d . . . C5 C 0.1436(5) 0.0398(3) 0.0768(3) 0.0704(13) Uani 1 1 d . . . C6 C 0.1785(6) 0.0602(3) 0.0022(3) 0.0832(15) Uani 1 1 d . . . H6 H 0.1406 0.1040 -0.0261 0.100 Uiso 1 1 calc R . . C7 C 0.2708(6) 0.0150(4) -0.0309(3) 0.0888(16) Uani 1 1 d . . . C8 C 0.3267(6) -0.0475(3) 0.0121(3) 0.0824(15) Uani 1 1 d . . . H8 H 0.3878 -0.0766 -0.0103 0.099 Uiso 1 1 calc R . . C9 C 0.2988(5) -0.0707(3) 0.0873(3) 0.0723(13) Uani 1 1 d . . . C10 C 0.0435(6) 0.0883(3) 0.1116(3) 0.0948(17) Uani 1 1 d . . . H10A H 0.0883 0.1168 0.1588 0.142 Uiso 1 1 calc R . . H10B H -0.0219 0.0546 0.1278 0.142 Uiso 1 1 calc R . . H10C H 0.0008 0.1241 0.0703 0.142 Uiso 1 1 calc R . . C11 C 0.3055(7) 0.0394(4) -0.1126(3) 0.124(2) Uani 1 1 d . . . H11A H 0.2569 0.0857 -0.1321 0.187 Uiso 1 1 calc R . . H11B H 0.2825 -0.0017 -0.1521 0.187 Uiso 1 1 calc R . . H11C H 0.3991 0.0497 -0.1052 0.187 Uiso 1 1 calc R . . C12 C 0.3601(6) -0.1411(3) 0.1332(4) 0.1015(18) Uani 1 1 d . . . H12A H 0.4086 -0.1255 0.1863 0.152 Uiso 1 1 calc R . . H12B H 0.4196 -0.1657 0.1024 0.152 Uiso 1 1 calc R . . H12C H 0.2915 -0.1772 0.1404 0.152 Uiso 1 1 calc R . . C13 C 0.2075(5) -0.0225(3) 0.4153(2) 0.0642(12) Uani 1 1 d . . . C14 C 0.1375(5) 0.0384(3) 0.4416(3) 0.0745(14) Uani 1 1 d . . . C15 C 0.1729(6) 0.0586(3) 0.5250(3) 0.0861(16) Uani 1 1 d . . . H15 H 0.1286 0.0997 0.5450 0.103 Uiso 1 1 calc R . . C16 C 0.2703(6) 0.0202(3) 0.5785(3) 0.0847(15) Uani 1 1 d . . . C17 C 0.3360(6) -0.0396(3) 0.5484(3) 0.0832(15) Uani 1 1 d . . . H17 H 0.4026 -0.0654 0.5846 0.100 Uiso 1 1 calc R . . C18 C 0.3080(5) -0.0637(3) 0.4665(3) 0.0751(14) Uani 1 1 d . . . C19 C 0.0272(6) 0.0825(3) 0.3851(4) 0.1032(19) Uani 1 1 d . . . H19A H 0.0599 0.1015 0.3379 0.155 Uiso 1 1 calc R . . H19B H -0.0013 0.1256 0.4146 0.155 Uiso 1 1 calc R . . H19C H -0.0465 0.0480 0.3673 0.155 Uiso 1 1 calc R . . C20 C 0.3049(8) 0.0427(4) 0.6690(3) 0.128(2) Uani 1 1 d . . . H20A H 0.3876 0.0707 0.6791 0.191 Uiso 1 1 calc R . . H20B H 0.3131 -0.0036 0.7023 0.191 Uiso 1 1 calc R . . H20C H 0.2359 0.0752 0.6828 0.191 Uiso 1 1 calc R . . C21 C 0.3822(6) -0.1291(3) 0.4367(3) 0.1014(19) Uani 1 1 d . . . H21A H 0.4564 -0.1431 0.4789 0.152 Uiso 1 1 calc R . . H21B H 0.4136 -0.1131 0.3880 0.152 Uiso 1 1 calc R . . H21C H 0.3243 -0.1733 0.4241 0.152 Uiso 1 1 calc R . . C22 C 0.3055(13) 0.2500 0.1101(7) 0.070(3) Uiso 0.50 2 d SPD . . C23 C 0.3845(14) 0.2500 0.0444(8) 0.084(4) Uiso 0.50 2 d SPD . . C26 C 0.384(2) 0.2500 0.3525(11) 0.136(7) Uiso 0.50 2 d SPD . . C27 C 0.3165(18) 0.2500 0.4224(10) 0.110(5) Uiso 0.50 2 d SPD . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1089(11) 0.0806(9) 0.0702(8) 0.0030(6) 0.0031(7) -0.0356(7) N1 0.077(3) 0.061(2) 0.047(2) -0.0010(17) 0.0049(17) -0.0094(19) C1 0.074(3) 0.059(3) 0.049(3) 0.003(2) 0.005(2) -0.007(2) Cl2 0.1303(18) 0.0650(11) 0.0646(11) 0.000 -0.0111(10) 0.000 N2 0.083(3) 0.064(2) 0.047(2) 0.0001(17) 0.0060(18) -0.009(2) C2 0.089(4) 0.065(3) 0.060(3) -0.003(2) 0.007(2) -0.018(3) Cl3 0.1156(16) 0.0756(12) 0.0742(12) 0.000 0.0324(10) 0.000 C3 0.092(4) 0.064(3) 0.061(3) -0.001(2) 0.012(2) -0.024(3) C4 0.083(3) 0.057(3) 0.050(3) 0.002(2) -0.003(2) -0.010(3) C5 0.084(4) 0.068(3) 0.054(3) 0.000(2) -0.003(2) -0.004(3) C6 0.102(4) 0.082(4) 0.057(3) 0.017(3) -0.007(3) -0.005(3) C7 0.108(5) 0.103(4) 0.053(3) 0.004(3) 0.008(3) -0.026(4) C8 0.097(4) 0.084(4) 0.067(3) 0.002(3) 0.019(3) 0.003(3) C9 0.090(4) 0.067(3) 0.058(3) 0.005(2) 0.010(3) -0.003(3) C10 0.099(4) 0.086(4) 0.095(4) 0.004(3) 0.006(3) 0.010(3) C11 0.147(6) 0.166(6) 0.062(4) 0.032(4) 0.023(3) -0.017(5) C12 0.114(5) 0.086(4) 0.109(4) 0.019(3) 0.032(3) 0.025(3) C13 0.082(3) 0.062(3) 0.048(3) 0.000(2) 0.011(2) -0.004(3) C14 0.094(4) 0.058(3) 0.076(3) 0.002(2) 0.026(3) -0.001(3) C15 0.119(5) 0.062(3) 0.086(4) -0.019(3) 0.042(4) -0.007(3) C16 0.105(5) 0.083(4) 0.067(3) -0.010(3) 0.017(3) -0.015(3) C17 0.095(4) 0.095(4) 0.054(3) 0.001(3) -0.001(3) -0.011(3) C18 0.095(4) 0.070(3) 0.060(3) -0.006(2) 0.013(3) -0.007(3) C19 0.107(5) 0.086(4) 0.117(5) 0.014(3) 0.021(4) 0.015(3) C20 0.175(7) 0.147(6) 0.062(4) -0.038(4) 0.024(4) -0.032(5) C21 0.120(5) 0.098(4) 0.084(4) -0.001(3) 0.012(3) 0.036(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1 1.677(4) . ? N1 C1 1.325(5) . ? N1 C2 1.388(5) . ? N1 C4 1.449(5) . ? C1 N2 1.329(5) . ? N2 C3 1.382(5) . ? N2 C13 1.462(5) . ? C2 C3 1.339(6) . ? N3 C23 1.132(8) . ? N4 C27 1.155(8) . ? C4 C5 1.395(6) . ? C4 C9 1.399(7) . ? C5 C6 1.388(7) . ? C5 C10 1.513(7) . ? C6 C7 1.408(7) . ? C7 C8 1.351(7) . ? C7 C11 1.516(7) . ? C8 C9 1.382(7) . ? C9 C12 1.498(7) . ? C13 C14 1.382(6) . ? C13 C18 1.396(6) . ? C14 C15 1.400(7) . ? C14 C19 1.523(7) . ? C15 C16 1.370(7) . ? C16 C17 1.368(7) . ? C16 C20 1.518(7) . ? C17 C18 1.392(6) . ? C18 C21 1.487(7) . ? C22 C23 1.468(8) . ? C26 C27 1.451(8) . ? 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 107.7(4) . . ? C1 N1 C4 124.5(4) . . ? C2 N1 C4 127.7(4) . . ? N1 C1 N2 109.1(4) . . ? N1 C1 Cl1 125.5(3) . . ? N2 C1 Cl1 125.4(3) . . ? C1 N2 C3 108.6(3) . . ? C1 N2 C13 124.9(4) . . ? C3 N2 C13 126.4(4) . . ? C3 C2 N1 107.8(4) . . ? C2 C3 N2 106.7(4) . . ? C5 C4 C9 123.2(4) . . ? C5 C4 N1 118.9(4) . . ? C9 C4 N1 117.9(4) . . ? C6 C5 C4 117.7(5) . . ? C6 C5 C10 120.2(5) . . ? C4 C5 C10 122.2(4) . . ? C5 C6 C7 120.5(5) . . ? C8 C7 C6 118.8(5) . . ? C8 C7 C11 122.6(6) . . ? C6 C7 C11 118.6(6) . . ? C7 C8 C9 124.1(5) . . ? C8 C9 C4 115.7(4) . . ? C8 C9 C12 123.2(5) . . ? C4 C9 C12 121.0(4) . . ? C14 C13 C18 124.1(4) . . ? C14 C13 N2 118.4(4) . . ? C18 C13 N2 117.5(4) . . ? C13 C14 C15 116.2(5) . . ? C13 C14 C19 123.5(5) . . ? C15 C14 C19 120.4(5) . . ? C16 C15 C14 122.6(5) . . ? C17 C16 C15 118.3(5) . . ? C17 C16 C20 120.4(6) . . ? C15 C16 C20 121.2(6) . . ? C16 C17 C18 123.3(5) . . ? C17 C18 C13 115.6(5) . . ? C17 C18 C21 121.3(5) . . ? C13 C18 C21 123.1(4) . . ? N3 C23 C22 173.0(18) . . ? N4 C27 C26 168(2) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.668 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.065 #===END data_compound4 _database_code_CSD 185384 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H22 Br2 N2' _chemical_formula_weight 462.23 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.4179(12) _cell_length_b 14.8370(16) _cell_length_c 13.4527(14) _cell_angle_alpha 90.00 _cell_angle_beta 114.275(2) _cell_angle_gamma 90.00 _cell_volume 2077.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 3.908 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.3417 _exptl_absorpt_correction_T_max 0.3417 _exptl_absorpt_process_details 'SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 9289 _diffrn_reflns_av_R_equivalents 0.0905 _diffrn_reflns_av_sigmaI/netI 0.0705 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 23.28 _reflns_number_total 2995 _reflns_number_gt 2061 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0995P)^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_number_reflns 2995 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1553 _refine_ls_wR_factor_gt 0.1418 _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_restrained_S_all 0.934 _refine_ls_shift/su_max 0.051 _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 Br1 Br 0.26156(6) 0.24970(4) 0.04640(5) 0.0615(3) Uani 1 1 d . . . Br2 Br 0.29409(8) 0.01430(5) -0.02747(6) 0.0883(4) Uani 1 1 d . . . N2 N 0.0616(5) 0.0787(3) -0.1980(4) 0.0571(12) Uani 1 1 d . . . N1 N 0.0424(5) 0.2150(3) -0.1564(4) 0.0575(12) Uani 1 1 d . . . C13 C 0.0409(6) -0.0061(4) -0.2531(5) 0.0603(16) Uani 1 1 d . . . C2 C 0.1546(5) 0.1828(4) -0.0743(5) 0.0537(14) Uani 1 1 d . . . C3 C 0.1648(6) 0.0976(4) -0.1007(5) 0.0603(16) Uani 1 1 d . . . C1 C -0.0179(6) 0.1514(4) -0.2352(5) 0.0590(16) Uani 1 1 d . . . C17 C 0.0689(7) -0.1057(5) -0.3790(5) 0.077(2) Uani 1 1 d . . . H8 H 0.0996 -0.1168 -0.4320 0.093 Uiso 1 1 calc R . . C15 C -0.0435(7) -0.1561(5) -0.2754(6) 0.0734(19) Uani 1 1 d . . . H9 H -0.0869 -0.2017 -0.2571 0.088 Uiso 1 1 calc R . . C18 C 0.0898(6) -0.0213(5) -0.3303(5) 0.0686(18) Uani 1 1 d . . . C4 C -0.0036(6) 0.3073(4) -0.1631(5) 0.0605(16) Uani 1 1 d . . . C5 C -0.0781(6) 0.3296(5) -0.1079(6) 0.0701(18) Uani 1 1 d . . . C16 C 0.0058(7) -0.1724(5) -0.3530(6) 0.079(2) Uani 1 1 d . . . C14 C -0.0288(6) -0.0724(4) -0.2253(5) 0.0625(17) Uani 1 1 d . . . C7 C -0.0836(9) 0.4822(6) -0.1716(8) 0.096(3) Uani 1 1 d . . . C8 C -0.0108(8) 0.4571(5) -0.2263(7) 0.085(2) Uani 1 1 d . . . H22 H 0.0115 0.4999 -0.2660 0.103 Uiso 1 1 calc R . . C21 C 0.1651(8) 0.0518(5) -0.3572(7) 0.090(2) Uani 1 1 d . . . H23A H 0.1158 0.1065 -0.3752 0.135 Uiso 1 1 calc R . . H23B H 0.1823 0.0332 -0.4182 0.135 Uiso 1 1 calc R . . H23C H 0.2448 0.0621 -0.2953 0.135 Uiso 1 1 calc R . . C9 C 0.0304(6) 0.3686(5) -0.2232(5) 0.0651(18) Uani 1 1 d . . . C20 C -0.0112(11) -0.2646(6) -0.4076(9) 0.113(3) Uani 1 1 d . . . H26A H -0.0268 -0.2569 -0.4829 0.170 Uiso 1 1 calc R . . H26B H -0.0829 -0.2951 -0.4028 0.170 Uiso 1 1 calc R . . H26C H 0.0653 -0.2997 -0.3715 0.170 Uiso 1 1 calc R . . C6 C -0.1162(7) 0.4199(6) -0.1129(7) 0.090(2) Uani 1 1 d . . . H27 H -0.1648 0.4377 -0.0753 0.108 Uiso 1 1 calc R . . C10 C -0.1136(9) 0.2603(5) -0.0427(8) 0.096(3) Uani 1 1 d . . . H32A H -0.1561 0.2104 -0.0889 0.144 Uiso 1 1 calc R . . H32B H -0.1702 0.2871 -0.0144 0.144 Uiso 1 1 calc R . . H32C H -0.0372 0.2394 0.0166 0.144 Uiso 1 1 calc R . . C19 C -0.0814(8) -0.0558(5) -0.1410(6) 0.079(2) Uani 1 1 d . . . H1A H -0.1564 -0.0924 -0.1570 0.118 Uiso 1 1 calc R . . H1B H -0.1040 0.0067 -0.1422 0.118 Uiso 1 1 calc R . . H1C H -0.0175 -0.0710 -0.0701 0.118 Uiso 1 1 calc R . . C12 C 0.1067(7) 0.3418(6) -0.2849(6) 0.091(2) Uani 1 1 d . . . H2A H 0.1865 0.3158 -0.2358 0.137 Uiso 1 1 calc R . . H2B H 0.1236 0.3939 -0.3192 0.137 Uiso 1 1 calc R . . H2C H 0.0593 0.2984 -0.3396 0.137 Uiso 1 1 calc R . . C11 C -0.1294(11) 0.5809(6) -0.1784(10) 0.148(5) Uani 1 1 d . . . H6A H -0.0591 0.6208 -0.1679 0.221 Uiso 1 1 calc R . . H6B H -0.1599 0.5916 -0.1227 0.221 Uiso 1 1 calc R . . H6C H -0.1976 0.5916 -0.2487 0.221 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0619(4) 0.0701(5) 0.0457(4) -0.0041(3) 0.0154(3) 0.0016(3) Br2 0.0928(6) 0.0860(6) 0.0597(5) -0.0037(4) 0.0045(4) 0.0348(4) N2 0.061(3) 0.060(3) 0.043(3) -0.001(2) 0.015(2) 0.004(2) N1 0.059(3) 0.053(3) 0.052(3) 0.002(3) 0.015(2) 0.003(2) C13 0.069(4) 0.062(4) 0.041(4) -0.003(3) 0.013(3) 0.008(3) C2 0.054(3) 0.062(4) 0.041(3) 0.001(3) 0.015(3) 0.002(3) C3 0.063(4) 0.066(4) 0.040(4) 0.000(3) 0.010(3) 0.009(3) C1 0.062(4) 0.058(4) 0.048(4) 0.001(3) 0.013(3) 0.001(3) C17 0.079(5) 0.099(6) 0.049(4) -0.020(4) 0.022(4) 0.009(4) C15 0.091(5) 0.059(4) 0.060(4) -0.007(3) 0.020(4) -0.001(4) C18 0.067(4) 0.084(5) 0.049(4) -0.003(3) 0.018(3) 0.008(3) C4 0.059(4) 0.060(4) 0.046(4) 0.000(3) 0.006(3) 0.005(3) C5 0.071(4) 0.077(5) 0.058(4) 0.004(3) 0.023(4) 0.013(4) C16 0.090(5) 0.079(5) 0.063(5) -0.019(4) 0.027(4) 0.004(4) C14 0.077(4) 0.064(4) 0.039(4) -0.005(3) 0.016(3) 0.008(3) C7 0.096(6) 0.072(6) 0.077(6) -0.001(4) -0.007(5) 0.016(5) C8 0.089(5) 0.056(5) 0.077(6) 0.011(4) 0.000(4) -0.006(4) C21 0.101(6) 0.104(6) 0.070(5) -0.004(4) 0.041(4) -0.004(5) C9 0.064(4) 0.069(5) 0.044(4) 0.005(3) 0.004(3) -0.008(3) C20 0.137(8) 0.096(6) 0.113(8) -0.040(5) 0.057(7) -0.001(5) C6 0.091(5) 0.092(6) 0.072(5) -0.004(5) 0.019(4) 0.027(5) C10 0.092(6) 0.119(7) 0.087(6) 0.000(5) 0.047(5) 0.012(5) C19 0.110(6) 0.079(5) 0.055(4) 0.001(4) 0.042(4) -0.002(4) C12 0.090(5) 0.107(6) 0.069(5) 0.005(4) 0.024(4) -0.021(5) C11 0.162(9) 0.061(6) 0.151(10) -0.015(5) -0.005(7) 0.038(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C2 1.866(6) . ? Br2 C3 1.866(6) . ? N2 C1 1.365(8) . ? N2 C3 1.383(7) . ? N2 C13 1.430(8) . ? N1 C1 1.375(8) . ? N1 C2 1.388(7) . ? N1 C4 1.456(8) . ? C13 C18 1.384(9) . ? C13 C14 1.409(9) . ? C2 C3 1.331(8) . ? C17 C16 1.352(11) . ? C17 C18 1.387(9) . ? C15 C14 1.389(9) . ? C15 C16 1.396(10) . ? C18 C21 1.518(10) . ? C4 C9 1.375(9) . ? C4 C5 1.379(9) . ? C5 C6 1.402(10) . ? C5 C10 1.511(10) . ? C16 C20 1.527(10) . ? C14 C19 1.507(9) . ? C7 C6 1.363(12) . ? C7 C8 1.369(11) . ? C7 C11 1.545(11) . ? C8 C9 1.390(10) . ? C9 C12 1.483(9) . ? 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 N2 C3 111.4(5) . . ? C1 N2 C13 124.2(5) . . ? C3 N2 C13 124.3(5) . . ? C1 N1 C2 112.5(5) . . ? C1 N1 C4 123.0(5) . . ? C2 N1 C4 124.4(5) . . ? C18 C13 C14 122.1(6) . . ? C18 C13 N2 120.1(6) . . ? C14 C13 N2 117.9(6) . . ? C3 C2 N1 105.5(5) . . ? C3 C2 Br1 129.8(4) . . ? N1 C2 Br1 124.7(4) . . ? C2 C3 N2 108.2(5) . . ? C2 C3 Br2 128.7(5) . . ? N2 C3 Br2 123.1(5) . . ? N2 C1 N1 102.4(5) . . ? C16 C17 C18 123.0(7) . . ? C14 C15 C16 120.8(7) . . ? C13 C18 C17 117.2(7) . . ? C13 C18 C21 120.3(6) . . ? C17 C18 C21 122.5(7) . . ? C9 C4 C5 123.0(6) . . ? C9 C4 N1 118.4(6) . . ? C5 C4 N1 118.6(6) . . ? C4 C5 C6 116.8(7) . . ? C4 C5 C10 121.5(6) . . ? C6 C5 C10 121.7(7) . . ? C17 C16 C15 119.2(7) . . ? C17 C16 C20 120.5(8) . . ? C15 C16 C20 120.3(8) . . ? C15 C14 C13 117.7(6) . . ? C15 C14 C19 120.4(7) . . ? C13 C14 C19 121.9(6) . . ? C6 C7 C8 119.9(8) . . ? C6 C7 C11 120.7(10) . . ? C8 C7 C11 119.4(10) . . ? C7 C8 C9 120.9(8) . . ? C4 C9 C8 117.9(8) . . ? C4 C9 C12 121.7(7) . . ? C8 C9 C12 120.4(7) . . ? C7 C6 C5 121.5(8) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 23.28 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.666 _refine_diff_density_min -0.803 _refine_diff_density_rms 0.111 #===END data_compound5 _database_code_CSD 185385 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H33 Br2 N5' _chemical_formula_weight 587.40 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 11.5086(15) _cell_length_b 19.474(3) _cell_length_c 13.6523(18) _cell_angle_alpha 90.00 _cell_angle_beta 101.511(2) _cell_angle_gamma 90.00 _cell_volume 2998.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 2.726 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.4952 _exptl_absorpt_correction_T_max 0.5854 _exptl_absorpt_process_details 'SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 13454 _diffrn_reflns_av_R_equivalents 0.0797 _diffrn_reflns_av_sigmaI/netI 0.0658 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 23.27 _reflns_number_total 4298 _reflns_number_gt 3009 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0692P)^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_number_reflns 4298 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1249 _refine_ls_wR_factor_gt 0.1131 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.965 _refine_ls_shift/su_max 0.042 _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 Br1 Br 0.72003(4) 0.15388(3) 0.35880(4) 0.0538(2) Uani 1 1 d . . . Br2 Br 0.79673(5) 0.05679(3) 0.54151(4) 0.0648(2) Uani 1 1 d . . . C20 C 1.1853(5) 0.3600(3) 0.4353(5) 0.0837(19) Uani 1 1 d . . . H20A H 1.2183 0.3266 0.4848 0.125 Uiso 1 1 calc R . . H20B H 1.1758 0.4029 0.4675 0.125 Uiso 1 1 calc R . . H20C H 1.2375 0.3662 0.3893 0.125 Uiso 1 1 calc R . . N2 N 0.7299(3) 0.2681(2) 0.2279(3) 0.0485(10) Uani 1 1 d . . . C4 C 0.4687(4) 0.1642(3) 0.1962(4) 0.0505(13) Uani 1 1 d . . . N1 N 0.5623(3) 0.2135(2) 0.1937(3) 0.0493(10) Uani 1 1 d . . . C13 C 0.8464(4) 0.2898(2) 0.2815(4) 0.0483(12) Uani 1 1 d . . . C14 C 0.9450(4) 0.2741(2) 0.2409(4) 0.0527(13) Uani 1 1 d . . . C9 C 0.4577(4) 0.1079(3) 0.1323(4) 0.0533(13) Uani 1 1 d . . . C2 C 0.5562(5) 0.2682(3) 0.1283(4) 0.0626(14) Uani 1 1 d . . . H2 H 0.4914 0.2797 0.0787 0.075 Uiso 1 1 calc R . . C8 C 0.3641(5) 0.0636(3) 0.1353(4) 0.0622(14) Uani 1 1 d . . . H8 H 0.3554 0.0252 0.0940 0.075 Uiso 1 1 calc R . . C1 C 0.6682(4) 0.2144(2) 0.2537(3) 0.0457(12) Uani 1 1 d . . . C18 C 0.8527(4) 0.3284(3) 0.3673(4) 0.0532(13) Uani 1 1 d . . . C5 C 0.3916(5) 0.1773(3) 0.2614(4) 0.0616(14) Uani 1 1 d . . . C16 C 1.0663(4) 0.3355(3) 0.3794(4) 0.0546(13) Uani 1 1 d . . . C7 C 0.2846(5) 0.0733(3) 0.1952(4) 0.0638(15) Uani 1 1 d . . . C17 C 0.9639(5) 0.3504(2) 0.4154(4) 0.0577(14) Uani 1 1 d . . . H17 H 0.9705 0.3760 0.4737 0.069 Uiso 1 1 calc R . . C3 C 0.6588(5) 0.3014(3) 0.1486(4) 0.0589(14) Uani 1 1 d . . . H3 H 0.6791 0.3400 0.1155 0.071 Uiso 1 1 calc R . . C21 C 0.7434(5) 0.3459(3) 0.4087(5) 0.0815(19) Uani 1 1 d . . . H21A H 0.7083 0.3044 0.4273 0.122 Uiso 1 1 calc R . . H21B H 0.6872 0.3696 0.3586 0.122 Uiso 1 1 calc R . . H21C H 0.7655 0.3749 0.4664 0.122 Uiso 1 1 calc R . . C15 C 1.0537(5) 0.2980(3) 0.2924(4) 0.0614(14) Uani 1 1 d . . . H15 H 1.1212 0.2883 0.2670 0.074 Uiso 1 1 calc R . . C6 C 0.3007(5) 0.1295(3) 0.2583(5) 0.0743(17) Uani 1 1 d . . . H6 H 0.2480 0.1358 0.3011 0.089 Uiso 1 1 calc R . . C19 C 0.9344(5) 0.2361(3) 0.1443(4) 0.087(2) Uani 1 1 d . . . H19A H 1.0117 0.2301 0.1292 0.130 Uiso 1 1 calc R . . H19B H 0.8856 0.2619 0.0917 0.130 Uiso 1 1 calc R . . H19C H 0.8990 0.1920 0.1499 0.130 Uiso 1 1 calc R . . C11 C 0.1810(6) 0.0250(4) 0.1929(5) 0.099(2) Uani 1 1 d . . . H11A H 0.1791 -0.0081 0.1404 0.148 Uiso 1 1 calc R . . H11B H 0.1084 0.0508 0.1807 0.148 Uiso 1 1 calc R . . H11C H 0.1897 0.0017 0.2559 0.148 Uiso 1 1 calc R . . C12 C 0.5437(5) 0.0954(3) 0.0635(4) 0.0816(19) Uani 1 1 d . . . H12A H 0.5096 0.1115 -0.0024 0.122 Uiso 1 1 calc R . . H12B H 0.5598 0.0471 0.0610 0.122 Uiso 1 1 calc R . . H12C H 0.6163 0.1196 0.0882 0.122 Uiso 1 1 calc R . . C10 C 0.4059(6) 0.2383(3) 0.3288(5) 0.096(2) Uani 1 1 d . . . H10A H 0.3451 0.2380 0.3677 0.144 Uiso 1 1 calc R . . H10B H 0.3996 0.2795 0.2894 0.144 Uiso 1 1 calc R . . H10C H 0.4823 0.2367 0.3726 0.144 Uiso 1 1 calc R . . C22 C 0.5476(6) -0.0555(4) 0.2839(7) 0.093(2) Uani 1 1 d . . . N3 N 0.5684(7) -0.0792(4) 0.2144(6) 0.139(3) Uani 1 1 d . . . C23 C 0.5214(7) -0.0243(4) 0.3729(6) 0.119(3) Uani 1 1 d . . . H23A H 0.5774 0.0117 0.3952 0.179 Uiso 1 1 calc R . . H23B H 0.5266 -0.0584 0.4244 0.179 Uiso 1 1 calc R . . H23C H 0.4427 -0.0055 0.3584 0.179 Uiso 1 1 calc R . . C27 C 0.8833(6) -0.0236(4) 0.2994(5) 0.096(2) Uani 1 1 d . . . H27A H 0.8271 -0.0606 0.2877 0.144 Uiso 1 1 calc R . . H27B H 0.8718 0.0024 0.3565 0.144 Uiso 1 1 calc R . . H27C H 0.9623 -0.0420 0.3118 0.144 Uiso 1 1 calc R . . C24 C 0.8219(7) -0.1622(4) 0.4868(6) 0.092(2) Uani 1 1 d . . . C25 C 0.9299(6) -0.1303(4) 0.5390(6) 0.107(2) Uani 1 1 d . . . H25A H 0.9132 -0.0843 0.5575 0.161 Uiso 1 1 calc R . . H25B H 0.9866 -0.1290 0.4962 0.161 Uiso 1 1 calc R . . H25C H 0.9616 -0.1563 0.5980 0.161 Uiso 1 1 calc R . . N5 N 0.8541(7) 0.0532(4) 0.1453(7) 0.138(3) Uani 1 1 d . . . C26 C 0.8665(6) 0.0202(4) 0.2131(6) 0.089(2) Uani 1 1 d . . . N4 N 0.7366(7) -0.1857(4) 0.4487(6) 0.153(3) 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 0.0525(3) 0.0551(4) 0.0519(3) 0.0104(2) 0.0062(2) -0.0007(2) Br2 0.0712(4) 0.0635(4) 0.0599(4) 0.0083(3) 0.0136(3) 0.0133(3) C20 0.060(4) 0.086(5) 0.097(5) -0.005(4) -0.006(3) -0.006(3) N2 0.048(2) 0.051(3) 0.047(2) 0.0062(19) 0.0105(19) -0.0058(19) C4 0.042(3) 0.062(3) 0.046(3) 0.013(3) 0.007(2) -0.003(2) N1 0.048(3) 0.050(3) 0.050(2) 0.007(2) 0.008(2) -0.0041(19) C13 0.045(3) 0.050(3) 0.049(3) 0.005(2) 0.006(2) -0.003(2) C14 0.051(3) 0.050(3) 0.058(3) -0.004(2) 0.014(3) -0.006(2) C9 0.046(3) 0.063(4) 0.052(3) 0.007(3) 0.014(2) 0.000(2) C2 0.047(3) 0.079(4) 0.057(3) 0.017(3) -0.002(3) -0.007(3) C8 0.062(4) 0.062(4) 0.059(3) 0.007(3) 0.005(3) -0.004(3) C1 0.047(3) 0.049(3) 0.041(3) 0.007(2) 0.007(2) 0.003(2) C18 0.055(3) 0.055(3) 0.052(3) 0.001(3) 0.013(3) 0.002(2) C5 0.055(3) 0.072(4) 0.061(3) -0.003(3) 0.020(3) -0.004(3) C16 0.049(3) 0.053(3) 0.058(3) 0.001(3) 0.001(3) -0.004(2) C7 0.054(4) 0.074(4) 0.063(4) 0.018(3) 0.010(3) -0.009(3) C17 0.064(4) 0.056(3) 0.050(3) -0.006(2) 0.005(3) -0.007(3) C3 0.068(4) 0.058(3) 0.049(3) 0.016(3) 0.008(3) 0.002(3) C21 0.070(4) 0.096(5) 0.083(4) -0.019(4) 0.028(3) -0.001(3) C15 0.053(3) 0.065(4) 0.070(4) -0.003(3) 0.022(3) -0.006(3) C6 0.054(4) 0.099(5) 0.078(4) 0.014(4) 0.034(3) 0.002(3) C19 0.080(4) 0.111(5) 0.075(4) -0.037(4) 0.029(3) -0.023(4) C11 0.080(5) 0.116(6) 0.100(5) 0.015(4) 0.017(4) -0.038(4) C12 0.078(4) 0.091(5) 0.083(4) -0.020(4) 0.034(4) -0.020(3) C10 0.093(5) 0.106(5) 0.100(5) -0.036(4) 0.045(4) -0.015(4) C22 0.081(5) 0.092(6) 0.101(6) 0.004(5) 0.001(4) -0.005(4) N3 0.156(7) 0.137(7) 0.120(7) -0.008(5) 0.015(5) 0.026(5) C23 0.105(6) 0.137(7) 0.112(7) -0.019(6) 0.013(5) -0.024(5) C27 0.095(5) 0.098(5) 0.096(5) -0.006(5) 0.020(4) 0.003(4) C24 0.074(5) 0.096(5) 0.106(6) 0.031(4) 0.018(4) 0.007(4) C25 0.078(5) 0.107(6) 0.139(7) 0.006(5) 0.028(5) -0.004(4) N5 0.133(6) 0.128(6) 0.150(7) 0.047(5) 0.022(5) -0.003(5) C26 0.070(5) 0.086(5) 0.110(6) 0.010(5) 0.014(4) 0.002(4) N4 0.107(6) 0.163(7) 0.170(8) 0.029(6) -0.019(5) -0.038(5) _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 Br1 C1 1.861(4) . ? C20 C16 1.506(7) . ? N2 C1 1.349(6) . ? N2 C3 1.381(6) . ? N2 C13 1.456(6) . ? C4 C9 1.391(7) . ? C4 C5 1.399(7) . ? C4 N1 1.449(6) . ? N1 C1 1.326(6) . ? N1 C2 1.383(6) . ? C13 C18 1.383(7) . ? C13 C14 1.393(6) . ? C14 C15 1.388(7) . ? C14 C19 1.496(7) . ? C9 C8 1.386(7) . ? C9 C12 1.515(7) . ? C2 C3 1.326(7) . ? C8 C7 1.357(8) . ? C18 C17 1.384(7) . ? C18 C21 1.517(7) . ? C5 C6 1.395(8) . ? C5 C10 1.492(8) . ? C16 C15 1.377(7) . ? C16 C17 1.395(7) . ? C7 C6 1.381(8) . ? C7 C11 1.514(8) . ? C22 N3 1.124(9) . ? C22 C23 1.443(11) . ? C27 C26 1.437(10) . ? C24 N4 1.113(9) . ? C24 C25 1.444(11) . ? N5 C26 1.112(9) . ? 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 N2 C3 107.9(4) . . ? C1 N2 C13 124.9(4) . . ? C3 N2 C13 126.9(4) . . ? C9 C4 C5 123.5(5) . . ? C9 C4 N1 118.9(4) . . ? C5 C4 N1 117.6(5) . . ? C1 N1 C2 108.0(4) . . ? C1 N1 C4 126.2(4) . . ? C2 N1 C4 125.7(4) . . ? C18 C13 C14 123.2(5) . . ? C18 C13 N2 118.1(4) . . ? C14 C13 N2 118.6(4) . . ? C15 C14 C13 116.7(5) . . ? C15 C14 C19 121.3(5) . . ? C13 C14 C19 122.0(5) . . ? C8 C9 C4 116.5(5) . . ? C8 C9 C12 121.7(5) . . ? C4 C9 C12 121.8(5) . . ? C3 C2 N1 108.2(4) . . ? C7 C8 C9 123.5(6) . . ? N1 C1 N2 108.4(4) . . ? N1 C1 Br1 125.5(3) . . ? N2 C1 Br1 126.0(4) . . ? C13 C18 C17 117.2(4) . . ? C13 C18 C21 122.1(5) . . ? C17 C18 C21 120.7(5) . . ? C6 C5 C4 115.2(5) . . ? C6 C5 C10 122.7(5) . . ? C4 C5 C10 122.1(5) . . ? C15 C16 C17 117.6(5) . . ? C15 C16 C20 122.3(5) . . ? C17 C16 C20 120.1(5) . . ? C8 C7 C6 117.7(5) . . ? C8 C7 C11 121.5(6) . . ? C6 C7 C11 120.8(5) . . ? C18 C17 C16 122.3(5) . . ? C2 C3 N2 107.3(5) . . ? C16 C15 C14 122.9(5) . . ? C7 C6 C5 123.6(5) . . ? N3 C22 C23 179.4(10) . . ? N4 C24 C25 177.6(10) . . ? N5 C26 C27 178.7(9) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.552 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.081 #===END data_compound6 _database_code_CSD 185386 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H25 Br N2' _chemical_formula_weight 385.34 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.7182(9) _cell_length_b 14.0483(15) _cell_length_c 16.2655(18) _cell_angle_alpha 90.00 _cell_angle_beta 101.879(2) _cell_angle_gamma 90.00 _cell_volume 1949.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 2.113 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.6202 _exptl_absorpt_correction_T_max 0.6202 _exptl_absorpt_process_details 'SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 8933 _diffrn_reflns_av_R_equivalents 0.0486 _diffrn_reflns_av_sigmaI/netI 0.0548 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 23.28 _reflns_number_total 5220 _reflns_number_gt 4020 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0559P)^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 0.061(8) _refine_ls_number_reflns 5220 _refine_ls_number_parameters 453 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.0992 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 0.943 _refine_ls_restrained_S_all 0.943 _refine_ls_shift/su_max 0.015 _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 0.32354(7) 1.03550(4) 1.00684(4) 0.0713(2) Uani 1 1 d . . . N1 N 0.0751(5) 0.7816(4) 0.8789(3) 0.0520(11) Uani 1 1 d . . . C1 C 0.0708(7) 0.8493(4) 0.9355(4) 0.0485(14) Uani 1 1 d . . . H1 H 0.129(4) 0.908(3) 0.945(2) 0.019(10) Uiso 1 1 d . . . Br2 Br 0.83462(7) 0.28151(4) 0.57338(4) 0.0684(2) Uani 1 1 d . . . N2 N -0.0289(5) 0.8228(3) 0.9830(3) 0.0510(13) Uani 1 1 d . . . C2 C -0.0282(7) 0.7090(5) 0.8912(4) 0.0600(16) Uani 1 1 d . . . H3 H -0.0491 0.6533 0.8601 0.072 Uiso 1 1 calc R . . H2 H 0.654(5) 0.415(3) 0.521(3) 0.041(13) Uiso 1 1 d . . . N3 N 0.5707(5) 0.5380(4) 0.4566(3) 0.0473(11) Uani 1 1 d . . . C3 C -0.0911(7) 0.7351(4) 0.9561(4) 0.0635(18) Uani 1 1 d . . . H4 H -0.1633 0.7006 0.9788 0.076 Uiso 1 1 calc R . . N4 N 0.4741(6) 0.4876(3) 0.5602(3) 0.0511(13) Uani 1 1 d . . . C4 C 0.1771(6) 0.7824(5) 0.8199(3) 0.0506(13) Uani 1 1 d . . . C5 C 0.1122(6) 0.7917(5) 0.7348(3) 0.0555(14) Uani 1 1 d . . . C6 C 0.2134(7) 0.7918(5) 0.6797(3) 0.0583(15) Uani 1 1 d . . . H5 H 0.1726 0.7974 0.6224 0.070 Uiso 1 1 calc R . . C7 C 0.3752(6) 0.7837(5) 0.7076(3) 0.0536(13) Uani 1 1 d . . . C8 C 0.4317(7) 0.7715(5) 0.7913(4) 0.0570(15) Uani 1 1 d . . . H6 H 0.5389 0.7622 0.8098 0.068 Uiso 1 1 calc R . . C9 C 0.3379(6) 0.7721(5) 0.8505(4) 0.0518(15) Uani 1 1 d . . . C10 C -0.0615(7) 0.8002(5) 0.7013(4) 0.080(2) Uani 1 1 d . . . H8 H -0.0800 0.8272 0.6459 0.121 Uiso 1 1 calc R . . H7 H -0.1065 0.8406 0.7377 0.121 Uiso 1 1 calc R . . H9 H -0.1087 0.7383 0.6990 0.121 Uiso 1 1 calc R . . C11 C 0.4817(7) 0.7875(5) 0.6463(4) 0.0703(16) Uani 1 1 d . . . H12 H 0.5153 0.8519 0.6412 0.105 Uiso 1 1 calc R . . H11 H 0.4265 0.7652 0.5925 0.105 Uiso 1 1 calc R . . H10 H 0.5714 0.7478 0.6659 0.105 Uiso 1 1 calc R . . C12 C 0.4068(7) 0.7610(5) 0.9430(4) 0.0653(19) Uani 1 1 d . . . H13 H 0.5098 0.7340 0.9503 0.098 Uiso 1 1 calc R . . H15 H 0.3412 0.7199 0.9679 0.098 Uiso 1 1 calc R . . H14 H 0.4132 0.8223 0.9698 0.098 Uiso 1 1 calc R . . C13 C -0.0601(6) 0.8757(4) 1.0549(3) 0.0483(14) Uani 1 1 d . . . C14 C 0.0244(7) 0.8513(5) 1.1334(4) 0.0572(17) Uani 1 1 d . . . C15 C -0.0047(7) 0.9015(5) 1.2010(4) 0.0590(16) Uani 1 1 d . . . H16 H 0.0503 0.8863 1.2547 0.071 Uiso 1 1 calc R . . C16 C -0.1146(8) 0.9746(4) 1.1911(4) 0.0581(16) Uani 1 1 d . . . C17 C -0.1970(7) 0.9943(4) 1.1120(4) 0.0582(17) Uani 1 1 d . . . H17 H -0.2734 1.0415 1.1050 0.070 Uiso 1 1 calc R . . C18 C -0.1705(7) 0.9465(4) 1.0418(4) 0.0560(15) Uani 1 1 d . . . C19 C 0.1478(7) 0.7736(7) 1.1447(4) 0.0805(19) Uani 1 1 d . . . H19 H 0.1022 0.7161 1.1186 0.121 Uiso 1 1 calc R . . H20 H 0.1865 0.7625 1.2035 0.121 Uiso 1 1 calc R . . H18 H 0.2327 0.7930 1.1191 0.121 Uiso 1 1 calc R . . C20 C -0.1410(9) 1.0290(7) 1.2678(4) 0.078(2) Uani 1 1 d . . . H22 H -0.0577 1.0741 1.2847 0.116 Uiso 1 1 calc R . . H21 H -0.1425 0.9852 1.3129 0.116 Uiso 1 1 calc R . . H23 H -0.2393 1.0620 1.2543 0.116 Uiso 1 1 calc R . . C21 C -0.2603(8) 0.9732(5) 0.9550(4) 0.0757(19) Uani 1 1 d . . . H25 H -0.2002 1.0178 0.9301 0.113 Uiso 1 1 calc R . . H24 H -0.3586 1.0015 0.9593 0.113 Uiso 1 1 calc R . . H26 H -0.2792 0.9171 0.9207 0.113 Uiso 1 1 calc R . . C22 C 0.5798(7) 0.4712(4) 0.5143(4) 0.0473(14) Uani 1 1 d . . . C23 C 0.4513(7) 0.6004(4) 0.4665(4) 0.0597(17) Uani 1 1 d . . . H27 H 0.4187 0.6543 0.4344 0.072 Uiso 1 1 calc R . . C24 C 0.3933(7) 0.5686(4) 0.5301(4) 0.0582(16) Uani 1 1 d . . . H28 H 0.3120 0.5961 0.5509 0.070 Uiso 1 1 calc R . . C25 C 0.6697(6) 0.5433(4) 0.3949(3) 0.0477(12) Uani 1 1 d . . . C26 C 0.8299(6) 0.5546(4) 0.4255(3) 0.0506(15) Uani 1 1 d . . . C27 C 0.9235(8) 0.5579(5) 0.3664(4) 0.0633(19) Uani 1 1 d . . . H29 H 1.0310 0.5660 0.3849 0.076 Uiso 1 1 calc R . . C28 C 0.8636(8) 0.5499(5) 0.2810(4) 0.0612(18) Uani 1 1 d . . . C29 C 0.7024(7) 0.5394(6) 0.2542(4) 0.0585(15) Uani 1 1 d . . . H30 H 0.6603 0.5340 0.1971 0.070 Uiso 1 1 calc R . . C30 C 0.6043(6) 0.5369(5) 0.3098(4) 0.0546(14) Uani 1 1 d . . . C31 C 0.9040(7) 0.5659(5) 0.5168(4) 0.070(2) Uani 1 1 d . . . H31 H 0.8352 0.6016 0.5443 0.105 Uiso 1 1 calc R . . H33 H 1.0018 0.5991 0.5221 0.105 Uiso 1 1 calc R . . H32 H 0.9224 0.5043 0.5424 0.105 Uiso 1 1 calc R . . C32 C 0.9701(9) 0.5540(7) 0.2193(5) 0.091(2) Uani 1 1 d . . . H34 H 1.0439 0.6049 0.2343 0.136 Uiso 1 1 calc R . . H36 H 0.9089 0.5649 0.1639 0.136 Uiso 1 1 calc R . . H35 H 1.0254 0.4948 0.2202 0.136 Uiso 1 1 calc R . . C33 C 0.4282(7) 0.5307(7) 0.2773(4) 0.0797(19) Uani 1 1 d . . . H39 H 0.3855 0.5937 0.2678 0.120 Uiso 1 1 calc R . . H38 H 0.3809 0.4988 0.3180 0.120 Uiso 1 1 calc R . . H37 H 0.4069 0.4957 0.2255 0.120 Uiso 1 1 calc R . . C34 C 0.4506(7) 0.4303(4) 0.6305(4) 0.0503(15) Uani 1 1 d . . . C35 C 0.3461(6) 0.3549(4) 0.6149(3) 0.0498(15) Uani 1 1 d . . . C36 C 0.3231(7) 0.3024(4) 0.6841(4) 0.0539(16) Uani 1 1 d . . . H40 H 0.2537 0.2513 0.6757 0.065 Uiso 1 1 calc R . . C37 C 0.4011(7) 0.3243(4) 0.7654(4) 0.0557(16) Uani 1 1 d . . . C38 C 0.5020(7) 0.4004(4) 0.7774(4) 0.0591(15) Uani 1 1 d . . . H41 H 0.5521 0.4161 0.8319 0.071 Uiso 1 1 calc R . . C39 C 0.5320(6) 0.4549(4) 0.7108(4) 0.0549(14) Uani 1 1 d . . . C40 C 0.2573(8) 0.3310(5) 0.5286(4) 0.074(2) Uani 1 1 d . . . H43 H 0.2061 0.3871 0.5026 0.111 Uiso 1 1 calc R . . H44 H 0.1803 0.2832 0.5322 0.111 Uiso 1 1 calc R . . H42 H 0.3285 0.3074 0.4956 0.111 Uiso 1 1 calc R . . C41 C 0.3723(8) 0.2666(5) 0.8385(4) 0.0711(19) Uani 1 1 d . . . H46 H 0.2685 0.2403 0.8252 0.107 Uiso 1 1 calc R . . H47 H 0.3826 0.3066 0.8871 0.107 Uiso 1 1 calc R . . H45 H 0.4475 0.2158 0.8497 0.107 Uiso 1 1 calc R . . C42 C 0.6431(7) 0.5383(7) 0.7275(4) 0.0784(18) Uani 1 1 d . . . H50 H 0.7240 0.5307 0.6960 0.118 Uiso 1 1 calc R . . H48 H 0.6893 0.5410 0.7864 0.118 Uiso 1 1 calc R . . H49 H 0.5866 0.5961 0.7108 0.118 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0634(4) 0.0589(4) 0.0852(5) -0.0094(4) 0.0004(3) -0.0010(3) N1 0.050(3) 0.053(3) 0.051(3) 0.001(3) 0.007(2) -0.004(3) C1 0.048(4) 0.046(3) 0.051(4) 0.000(3) 0.009(3) -0.003(3) Br2 0.0569(4) 0.0585(3) 0.0817(4) 0.0015(4) -0.0043(3) 0.0043(3) N2 0.048(3) 0.051(3) 0.054(3) -0.004(2) 0.013(3) -0.004(2) C2 0.059(4) 0.056(4) 0.066(4) -0.012(3) 0.014(3) -0.008(3) N3 0.044(3) 0.048(3) 0.047(3) 0.003(3) 0.003(2) 0.001(3) C3 0.053(4) 0.055(4) 0.083(5) -0.005(3) 0.016(4) -0.016(3) N4 0.044(3) 0.053(3) 0.057(3) -0.001(3) 0.011(3) 0.002(2) C4 0.049(3) 0.053(3) 0.050(3) -0.006(3) 0.012(3) 0.003(3) C5 0.050(3) 0.060(3) 0.053(3) -0.008(3) 0.002(3) -0.002(3) C6 0.069(4) 0.061(4) 0.040(3) -0.003(3) 0.000(3) 0.000(4) C7 0.057(4) 0.053(3) 0.053(3) 0.001(4) 0.015(3) 0.002(3) C8 0.049(3) 0.058(4) 0.062(4) 0.002(4) 0.008(3) 0.011(3) C9 0.047(3) 0.054(4) 0.050(3) -0.002(3) 0.002(3) 0.006(3) C10 0.062(4) 0.099(6) 0.072(4) -0.002(4) -0.006(3) 0.011(4) C11 0.071(4) 0.074(4) 0.069(4) -0.001(4) 0.022(3) -0.002(4) C12 0.062(4) 0.071(5) 0.057(4) 0.003(3) -0.002(3) 0.014(3) C13 0.042(3) 0.054(3) 0.049(3) 0.003(3) 0.009(3) -0.010(3) C14 0.052(4) 0.059(4) 0.058(4) 0.012(3) 0.006(3) -0.009(3) C15 0.054(4) 0.072(4) 0.049(4) 0.010(3) 0.005(3) -0.011(3) C16 0.065(4) 0.058(4) 0.053(4) 0.001(3) 0.016(3) -0.018(3) C17 0.060(4) 0.060(4) 0.056(4) 0.001(3) 0.016(3) 0.002(3) C18 0.053(4) 0.066(4) 0.049(4) 0.001(3) 0.008(3) 0.000(3) C19 0.071(4) 0.082(5) 0.083(5) 0.023(5) 0.001(3) 0.007(4) C20 0.091(5) 0.085(5) 0.063(4) -0.018(5) 0.030(4) -0.022(5) C21 0.074(5) 0.096(5) 0.053(4) 0.000(4) 0.003(3) 0.019(4) C22 0.043(4) 0.048(4) 0.048(4) 0.000(3) 0.004(3) 0.004(3) C23 0.055(4) 0.046(3) 0.071(4) 0.003(3) -0.001(3) 0.011(3) C24 0.051(4) 0.056(4) 0.067(4) -0.001(3) 0.012(3) 0.013(3) C25 0.048(3) 0.044(3) 0.048(3) 0.002(3) 0.003(3) -0.002(3) C26 0.052(4) 0.050(4) 0.050(3) -0.004(3) 0.008(3) -0.004(3) C27 0.053(4) 0.070(5) 0.064(4) 0.011(3) 0.005(3) -0.009(3) C28 0.071(5) 0.052(4) 0.062(4) 0.008(4) 0.017(4) -0.003(3) C29 0.066(4) 0.059(3) 0.047(3) 0.001(4) 0.005(3) -0.011(4) C30 0.052(3) 0.046(3) 0.057(4) 0.005(3) -0.009(3) -0.010(3) C31 0.051(4) 0.092(5) 0.060(4) -0.008(3) -0.007(3) -0.009(3) C32 0.093(6) 0.106(7) 0.077(5) 0.007(5) 0.028(4) -0.011(5) C33 0.062(4) 0.094(5) 0.070(4) 0.002(5) -0.015(3) -0.013(4) C34 0.047(4) 0.053(3) 0.054(4) 0.004(3) 0.016(3) 0.005(3) C35 0.048(4) 0.059(4) 0.045(4) -0.009(3) 0.014(3) -0.002(3) C36 0.060(4) 0.051(4) 0.051(4) -0.009(3) 0.012(3) -0.005(3) C37 0.061(4) 0.048(3) 0.057(4) -0.006(3) 0.011(3) 0.008(3) C38 0.071(4) 0.058(4) 0.045(3) -0.003(3) 0.003(3) 0.008(3) C39 0.042(3) 0.059(4) 0.058(4) -0.002(3) -0.001(3) 0.002(3) C40 0.075(5) 0.087(5) 0.058(4) -0.016(4) 0.009(4) -0.021(4) C41 0.082(5) 0.071(5) 0.058(4) 0.004(3) 0.010(3) 0.004(4) C42 0.071(4) 0.077(4) 0.074(4) -0.003(4) -0.015(3) -0.018(4) _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 Br1 Br1 0.0000(17) 1 ? N1 C1 1.329(8) . ? N1 C2 1.403(8) . ? N1 C4 1.436(6) . ? C1 N2 1.330(7) . ? Br2 Br2 0.000(2) 1 ? N2 C3 1.381(7) . ? N2 C13 1.458(7) . ? C2 C3 1.336(8) . ? N3 C22 1.318(7) . ? N3 C23 1.396(7) . ? N3 C25 1.454(7) . ? N4 C22 1.321(7) . ? N4 C24 1.374(7) . ? N4 C34 1.447(7) . ? C4 C5 1.390(7) . ? C4 C9 1.395(7) . ? C5 C6 1.380(7) . ? C5 C10 1.505(8) . ? C6 C7 1.395(8) . ? C7 C8 1.360(8) . ? C7 C11 1.497(7) . ? C8 C9 1.385(8) . ? C9 C12 1.510(8) . ? C13 C18 1.369(8) . ? C13 C14 1.380(8) . ? C14 C15 1.374(9) . ? C14 C19 1.517(10) . ? C15 C16 1.391(9) . ? C16 C17 1.367(8) . ? C16 C20 1.520(9) . ? C17 C18 1.384(8) . ? C18 C21 1.514(8) . ? C23 C24 1.319(9) . ? C25 C30 1.388(7) . ? C25 C26 1.391(7) . ? C26 C27 1.383(8) . ? C26 C31 1.502(8) . ? C27 C28 1.385(9) . ? C28 C29 1.390(9) . ? C28 C32 1.503(9) . ? C29 C30 1.366(8) . ? C30 C33 1.520(8) . ? C34 C35 1.385(8) . ? C34 C39 1.396(8) . ? C35 C36 1.395(8) . ? C35 C40 1.495(8) . ? C36 C37 1.391(8) . ? C37 C38 1.373(8) . ? C37 C41 1.502(9) . ? C38 C39 1.396(8) . ? C39 C42 1.508(10) . ? 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 108.1(5) . . ? C1 N1 C4 124.6(6) . . ? C2 N1 C4 127.3(6) . . ? N1 C1 N2 108.5(5) . . ? C1 N2 C3 109.1(5) . . ? C1 N2 C13 125.1(5) . . ? C3 N2 C13 125.7(5) . . ? C3 C2 N1 107.1(5) . . ? C22 N3 C23 107.6(5) . . ? C22 N3 C25 124.8(5) . . ? C23 N3 C25 127.6(6) . . ? C2 C3 N2 107.2(6) . . ? C22 N4 C24 108.0(6) . . ? C22 N4 C34 125.3(5) . . ? C24 N4 C34 126.7(6) . . ? C5 C4 C9 122.6(5) . . ? C5 C4 N1 119.0(5) . . ? C9 C4 N1 118.4(5) . . ? C6 C5 C4 117.6(5) . . ? C6 C5 C10 119.7(5) . . ? C4 C5 C10 122.7(5) . . ? C5 C6 C7 121.8(5) . . ? C8 C7 C6 118.0(5) . . ? C8 C7 C11 121.7(5) . . ? C6 C7 C11 120.3(5) . . ? C7 C8 C9 123.4(5) . . ? C8 C9 C4 116.5(5) . . ? C8 C9 C12 121.4(5) . . ? C4 C9 C12 122.1(5) . . ? C18 C13 C14 123.3(6) . . ? C18 C13 N2 119.2(5) . . ? C14 C13 N2 117.6(5) . . ? C15 C14 C13 117.5(6) . . ? C15 C14 C19 121.1(6) . . ? C13 C14 C19 121.4(6) . . ? C14 C15 C16 121.6(6) . . ? C17 C16 C15 118.3(6) . . ? C17 C16 C20 122.2(7) . . ? C15 C16 C20 119.5(7) . . ? C16 C17 C18 122.3(6) . . ? C13 C18 C17 117.1(5) . . ? C13 C18 C21 122.5(5) . . ? C17 C18 C21 120.4(6) . . ? N3 C22 N4 109.3(5) . . ? C24 C23 N3 107.0(5) . . ? C23 C24 N4 108.0(6) . . ? C30 C25 C26 122.7(5) . . ? C30 C25 N3 120.3(5) . . ? C26 C25 N3 117.0(5) . . ? C27 C26 C25 116.6(5) . . ? C27 C26 C31 119.2(5) . . ? C25 C26 C31 124.2(5) . . ? C26 C27 C28 122.6(6) . . ? C27 C28 C29 118.1(6) . . ? C27 C28 C32 120.7(6) . . ? C29 C28 C32 121.2(6) . . ? C30 C29 C28 121.7(6) . . ? C29 C30 C25 118.2(5) . . ? C29 C30 C33 119.8(5) . . ? C25 C30 C33 121.9(5) . . ? C35 C34 C39 123.3(5) . . ? C35 C34 N4 118.4(5) . . ? C39 C34 N4 118.3(5) . . ? C34 C35 C36 117.1(5) . . ? C34 C35 C40 122.5(5) . . ? C36 C35 C40 120.4(5) . . ? C37 C36 C35 121.8(6) . . ? C38 C37 C36 118.8(6) . . ? C38 C37 C41 120.9(6) . . ? C36 C37 C41 120.3(6) . . ? C37 C38 C39 122.2(6) . . ? C38 C39 C34 116.7(5) . . ? C38 C39 C42 120.2(5) . . ? C34 C39 C42 123.1(6) . . ? 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 C1 H1 Br1 0.96(4) 2.53(4) 3.463(6) 163(3) 1 C22 H2 Br2 1.01(5) 2.49(5) 3.475(6) 166(4) 1 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 23.28 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.335 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.054 #===END data_compound7 _database_code_CSD 185387 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C84 H96 Al4 Cl20 N8' _chemical_formula_weight 2034.61 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' 'Al' 'Al' 0.0645 0.0514 '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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 16.952(3) _cell_length_b 18.808(3) _cell_length_c 19.068(3) _cell_angle_alpha 63.838(3) _cell_angle_beta 88.463(4) _cell_angle_gamma 77.431(4) _cell_volume 5309.0(15) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2096 _exptl_absorpt_coefficient_mu 0.590 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.8429 _exptl_absorpt_correction_T_max 0.8763 _exptl_absorpt_process_details 'SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 24829 _diffrn_reflns_av_R_equivalents 0.0964 _diffrn_reflns_av_sigmaI/netI 0.2016 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 23.31 _reflns_number_total 15142 _reflns_number_gt 4196 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0780P)^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_number_reflns 15142 _refine_ls_number_parameters 1069 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2290 _refine_ls_R_factor_gt 0.0688 _refine_ls_wR_factor_ref 0.2101 _refine_ls_wR_factor_gt 0.1462 _refine_ls_goodness_of_fit_ref 0.818 _refine_ls_restrained_S_all 0.818 _refine_ls_shift/su_max 0.530 _refine_ls_shift/su_mean 0.011 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.38101(15) 0.54281(17) -0.26302(18) 0.1272(10) Uani 1 1 d . . . Al1 Al 0.49658(17) 0.46118(18) -0.22163(18) 0.0953(10) Uani 1 1 d . . . Cl2 Cl 0.5877(2) 0.5255(2) -0.2424(3) 0.2057(19) Uani 1 1 d . . . Al2 Al 0.58423(19) -0.0446(2) 0.24698(18) 0.1030(10) Uani 1 1 d . . . Cl3 Cl 0.52291(16) 0.38796(18) -0.28120(16) 0.1280(11) Uani 1 1 d . . . Al3 Al 1.01134(16) 0.03815(18) 0.23021(17) 0.0881(9) Uani 1 1 d . . . Cl4 Cl 0.49560(18) 0.38431(19) -0.10194(16) 0.1400(12) Uani 1 1 d . . . Al4 Al 1.00302(19) 0.50772(19) 0.22377(18) 0.0981(10) Uani 1 1 d . . . Cl5 Cl 0.6914(2) -0.1326(2) 0.2731(2) 0.2051(18) Uani 1 1 d . . . Cl6 Cl 0.59861(19) 0.0678(2) 0.1590(2) 0.1683(14) Uani 1 1 d . . . Cl7 Cl 0.5510(2) -0.0228(3) 0.3439(2) 0.1848(16) Uani 1 1 d . . . Cl8 Cl 0.4887(2) -0.0763(2) 0.2090(2) 0.1833(16) Uani 1 1 d . . . Cl9 Cl 1.11968(14) -0.05443(16) 0.28199(16) 0.1120(9) Uani 1 1 d . . . Cl10 Cl 0.99520(17) 0.11693(18) 0.28334(17) 0.1311(11) Uani 1 1 d . . . Cl11 Cl 0.91155(16) -0.01680(18) 0.2514(2) 0.1498(13) Uani 1 1 d . . . Cl12 Cl 1.02095(18) 0.10587(18) 0.10982(15) 0.1316(11) Uani 1 1 d . . . Cl13 Cl 1.0942(2) 0.4027(2) 0.2708(3) 0.227(2) Uani 1 1 d . . . Cl14 Cl 1.0032(2) 0.5688(3) 0.10188(17) 0.1961(18) Uani 1 1 d . . . Cl15 Cl 1.01687(16) 0.58633(18) 0.27187(17) 0.1257(10) Uani 1 1 d . . . Cl16 Cl 0.88864(17) 0.47909(18) 0.25368(17) 0.1273(10) Uani 1 1 d . . . Cl1A Cl 0.82092(13) 0.27864(16) 0.52108(16) 0.1025(9) Uani 1 1 d . . . N1A N 0.8537(4) 0.3532(4) 0.6025(4) 0.070(2) Uani 1 1 d . . . C1A C 0.7996(6) 0.3292(5) 0.5743(5) 0.066(2) Uani 1 1 d . . . N2A N 0.7259(5) 0.3508(4) 0.5961(4) 0.068(2) Uani 1 1 d . . . C2A C 0.8113(6) 0.3927(6) 0.6443(5) 0.093(3) Uani 1 1 d . . . H2A H 0.8340 0.4163 0.6700 0.112 Uiso 1 1 calc R . . C3A C 0.7330(6) 0.3910(6) 0.6413(5) 0.093(3) Uani 1 1 d . . . H3A H 0.6917 0.4122 0.6646 0.112 Uiso 1 1 calc R . . C4A C 0.9392(6) 0.3461(7) 0.5867(7) 0.071(3) Uani 1 1 d . . . C5A C 0.9561(6) 0.3999(7) 0.5143(7) 0.083(3) Uani 1 1 d . . . C6A C 1.0368(7) 0.3929(7) 0.4982(6) 0.101(3) Uani 1 1 d . . . H6A H 1.0513 0.4295 0.4507 0.121 Uiso 1 1 calc R . . C7A C 1.0959(7) 0.3317(9) 0.5526(9) 0.103(4) Uani 1 1 d . . . C8A C 1.0752(7) 0.2785(7) 0.6241(8) 0.095(3) Uani 1 1 d . . . H8A H 1.1158 0.2382 0.6605 0.115 Uiso 1 1 calc R . . C9A C 0.9959(7) 0.2839(6) 0.6423(6) 0.077(3) Uani 1 1 d . . . C10A C 0.8937(6) 0.4667(6) 0.4535(5) 0.111(3) Uani 1 1 d . . . H10A H 0.8701 0.4454 0.4238 0.167 Uiso 1 1 calc R . . H10B H 0.9189 0.5091 0.4190 0.167 Uiso 1 1 calc R . . H10C H 0.8522 0.4883 0.4787 0.167 Uiso 1 1 calc R . . C11A C 1.1845(6) 0.3211(7) 0.5337(7) 0.166(5) Uani 1 1 d . . . H11A H 1.2131 0.3427 0.5597 0.249 Uiso 1 1 calc R . . H11B H 1.1874 0.3497 0.4781 0.249 Uiso 1 1 calc R . . H11C H 1.2086 0.2643 0.5515 0.249 Uiso 1 1 calc R . . C12A C 0.9715(6) 0.2266(6) 0.7188(6) 0.106(3) Uani 1 1 d . . . H12A H 0.9498 0.2559 0.7480 0.159 Uiso 1 1 calc R . . H12B H 1.0180 0.1846 0.7481 0.159 Uiso 1 1 calc R . . H12C H 0.9311 0.2026 0.7093 0.159 Uiso 1 1 calc R . . C13A C 0.6504(5) 0.3403(6) 0.5724(6) 0.067(2) Uani 1 1 d . . . C14A C 0.6090(6) 0.4035(6) 0.5040(6) 0.081(3) Uani 1 1 d . . . C15A C 0.5361(6) 0.3903(7) 0.4824(6) 0.093(3) Uani 1 1 d . . . H15A H 0.5064 0.4296 0.4362 0.112 Uiso 1 1 calc R . . C16A C 0.5073(6) 0.3223(7) 0.5265(7) 0.087(3) Uani 1 1 d . . . C17A C 0.5521(6) 0.2634(6) 0.5919(6) 0.085(3) Uani 1 1 d . . . H17A H 0.5334 0.2165 0.6210 0.102 Uiso 1 1 calc R . . C18A C 0.6255(6) 0.2702(6) 0.6176(6) 0.074(3) Uani 1 1 d . . . C19A C 0.6394(5) 0.4796(6) 0.4548(5) 0.107(3) Uani 1 1 d . . . H19A H 0.5964 0.5268 0.4432 0.160 Uiso 1 1 calc R . . H19B H 0.6568 0.4787 0.4069 0.160 Uiso 1 1 calc R . . H19C H 0.6841 0.4814 0.4834 0.160 Uiso 1 1 calc R . . C20A C 0.4278(6) 0.3129(7) 0.5007(7) 0.146(5) Uani 1 1 d . . . H20A H 0.4221 0.3359 0.4446 0.219 Uiso 1 1 calc R . . H20B H 0.3836 0.3407 0.5185 0.219 Uiso 1 1 calc R . . H20C H 0.4274 0.2562 0.5228 0.219 Uiso 1 1 calc R . . C21A C 0.6735(6) 0.2023(6) 0.6922(5) 0.120(4) Uani 1 1 d . . . H21A H 0.7163 0.1688 0.6787 0.181 Uiso 1 1 calc R . . H21B H 0.6382 0.1698 0.7245 0.181 Uiso 1 1 calc R . . H21C H 0.6964 0.2257 0.7203 0.181 Uiso 1 1 calc R . . Cl1B Cl 0.66581(13) 0.24082(15) 0.43289(15) 0.0955(8) Uani 1 1 d . . . N1B N 0.6414(5) 0.1610(4) 0.3530(4) 0.076(2) Uani 1 1 d . . . C1B C 0.6929(6) 0.1822(5) 0.3871(5) 0.066(2) Uani 1 1 d . . . N2B N 0.7693(5) 0.1534(4) 0.3772(4) 0.070(2) Uani 1 1 d . . . C2B C 0.6880(7) 0.1146(6) 0.3203(6) 0.100(3) Uani 1 1 d . . . H2B H 0.6684 0.0910 0.2926 0.120 Uiso 1 1 calc R . . C3B C 0.7653(6) 0.1102(6) 0.3354(6) 0.092(3) Uani 1 1 d . . . H3B H 0.8095 0.0825 0.3203 0.111 Uiso 1 1 calc R . . C4B C 0.5549(6) 0.1791(7) 0.3549(7) 0.076(3) Uani 1 1 d . . . C5B C 0.5225(7) 0.1351(6) 0.4218(7) 0.082(3) Uani 1 1 d . . . C6B C 0.4387(7) 0.1527(7) 0.4225(7) 0.105(4) Uani 1 1 d . . . H6B H 0.4143 0.1225 0.4667 0.126 Uiso 1 1 calc R . . C7B C 0.3917(7) 0.2144(9) 0.3583(9) 0.108(4) Uani 1 1 d . . . C8B C 0.4262(8) 0.2571(7) 0.2919(8) 0.112(4) Uani 1 1 d . . . H8B H 0.3934 0.2975 0.2481 0.134 Uiso 1 1 calc R . . C9B C 0.5096(8) 0.2409(7) 0.2887(7) 0.092(3) Uani 1 1 d . . . C10B C 0.5752(6) 0.0678(6) 0.4909(6) 0.120(4) Uani 1 1 d . . . H10D H 0.6180 0.0385 0.4731 0.179 Uiso 1 1 calc R . . H10E H 0.5434 0.0314 0.5241 0.179 Uiso 1 1 calc R . . H10F H 0.5982 0.0903 0.5197 0.179 Uiso 1 1 calc R . . C11B C 0.2984(6) 0.2348(7) 0.3601(7) 0.154(5) Uani 1 1 d . . . H11D H 0.2819 0.2821 0.3690 0.231 Uiso 1 1 calc R . . H11E H 0.2821 0.1896 0.4016 0.231 Uiso 1 1 calc R . . H11F H 0.2734 0.2453 0.3109 0.231 Uiso 1 1 calc R . . C12B C 0.5495(7) 0.2886(7) 0.2165(6) 0.137(4) Uani 1 1 d . . . H12D H 0.5730 0.2541 0.1928 0.205 Uiso 1 1 calc R . . H12E H 0.5912 0.3080 0.2310 0.205 Uiso 1 1 calc R . . H12F H 0.5097 0.3340 0.1798 0.205 Uiso 1 1 calc R . . C13B C 0.8413(5) 0.1628(6) 0.4054(6) 0.065(2) Uani 1 1 d . . . C14B C 0.8804(6) 0.1017(7) 0.4764(7) 0.082(3) Uani 1 1 d . . . C15B C 0.9528(7) 0.1102(7) 0.5023(6) 0.092(3) Uani 1 1 d . . . H15B H 0.9799 0.0702 0.5496 0.110 Uiso 1 1 calc R . . C16B C 0.9844(6) 0.1764(8) 0.4592(8) 0.093(3) Uani 1 1 d . . . C17B C 0.9425(7) 0.2360(6) 0.3889(7) 0.086(3) Uani 1 1 d . . . H17B H 0.9639 0.2809 0.3595 0.104 Uiso 1 1 calc R . . C18B C 0.8692(6) 0.2314(6) 0.3601(6) 0.078(3) Uani 1 1 d . . . C19B C 0.8478(6) 0.0281(6) 0.5268(6) 0.118(4) Uani 1 1 d . . . H19D H 0.8124 0.0399 0.5624 0.177 Uiso 1 1 calc R . . H19E H 0.8920 -0.0170 0.5561 0.177 Uiso 1 1 calc R . . H19F H 0.8181 0.0145 0.4941 0.177 Uiso 1 1 calc R . . C20B C 1.0647(6) 0.1851(6) 0.4863(7) 0.142(5) Uani 1 1 d . . . H20D H 1.1067 0.1741 0.4553 0.213 Uiso 1 1 calc R . . H20E H 1.0787 0.1471 0.5405 0.213 Uiso 1 1 calc R . . H20F H 1.0588 0.2395 0.4802 0.213 Uiso 1 1 calc R . . C21B C 0.8277(6) 0.2949(6) 0.2833(5) 0.110(3) Uani 1 1 d . . . H21D H 0.8083 0.2694 0.2555 0.166 Uiso 1 1 calc R . . H21E H 0.8652 0.3259 0.2530 0.166 Uiso 1 1 calc R . . H21F H 0.7827 0.3305 0.2918 0.166 Uiso 1 1 calc R . . Cl1C Cl 0.25033(17) 0.42970(15) 0.12152(14) 0.1123(9) Uani 1 1 d . . . N1C N 0.2586(4) 0.3506(5) 0.0323(5) 0.076(2) Uani 1 1 d . . . C1C C 0.2534(5) 0.4206(7) 0.0374(6) 0.072(3) Uani 1 1 d . . . N2C N 0.2498(4) 0.4814(5) -0.0320(5) 0.070(2) Uani 1 1 d . . . C2C C 0.2590(6) 0.3675(7) -0.0455(6) 0.100(3) Uani 1 1 d . . . H2C H 0.2633 0.3305 -0.0661 0.121 Uiso 1 1 calc R . . C3C C 0.2518(5) 0.4491(7) -0.0863(6) 0.088(3) Uani 1 1 d . . . H3C H 0.2488 0.4785 -0.1405 0.105 Uiso 1 1 calc R . . C4C C 0.2682(7) 0.2708(6) 0.0993(6) 0.078(3) Uani 1 1 d . . . C5C C 0.2016(6) 0.2467(7) 0.1359(7) 0.088(3) Uani 1 1 d . . . C6C C 0.2173(7) 0.1718(8) 0.2006(7) 0.094(3) Uani 1 1 d . . . H6C H 0.1735 0.1538 0.2275 0.113 Uiso 1 1 calc R . . C7C C 0.2920(8) 0.1229(7) 0.2276(6) 0.090(3) Uani 1 1 d . . . C8C C 0.3562(6) 0.1509(7) 0.1873(7) 0.095(3) Uani 1 1 d . . . H8C H 0.4083 0.1187 0.2052 0.114 Uiso 1 1 calc R . . C9C C 0.3465(6) 0.2241(7) 0.1223(6) 0.084(3) Uani 1 1 d . . . C10C C 0.1168(5) 0.2973(6) 0.1106(6) 0.132(4) Uani 1 1 d . . . H10G H 0.0794 0.2662 0.1408 0.198 Uiso 1 1 calc R . . H10H H 0.1052 0.3134 0.0560 0.198 Uiso 1 1 calc R . . H10I H 0.1115 0.3449 0.1188 0.198 Uiso 1 1 calc R . . C11C C 0.3072(6) 0.0420(6) 0.2988(6) 0.128(4) Uani 1 1 d . . . H11G H 0.3145 0.0496 0.3446 0.191 Uiso 1 1 calc R . . H11H H 0.3552 0.0069 0.2940 0.191 Uiso 1 1 calc R . . H11I H 0.2618 0.0180 0.3033 0.191 Uiso 1 1 calc R . . C12C C 0.4194(5) 0.2528(5) 0.0792(6) 0.114(4) Uani 1 1 d . . . H12G H 0.4681 0.2120 0.1045 0.171 Uiso 1 1 calc R . . H12H H 0.4230 0.3026 0.0803 0.171 Uiso 1 1 calc R . . H12I H 0.4129 0.2620 0.0258 0.171 Uiso 1 1 calc R . . C13C C 0.2442(6) 0.5663(6) -0.0493(4) 0.065(2) Uani 1 1 d . . . C14C C 0.3142(5) 0.5900(6) -0.0427(5) 0.074(3) Uani 1 1 d . . . C15C C 0.3055(5) 0.6698(6) -0.0587(5) 0.077(3) Uani 1 1 d . . . H15C H 0.3517 0.6874 -0.0546 0.093 Uiso 1 1 calc R . . C16C C 0.2319(7) 0.7256(6) -0.0804(5) 0.079(3) Uani 1 1 d . . . C17C C 0.1640(6) 0.6991(7) -0.0856(5) 0.084(3) Uani 1 1 d . . . H17C H 0.1138 0.7357 -0.0989 0.101 Uiso 1 1 calc R . . C18C C 0.1681(5) 0.6188(6) -0.0715(5) 0.069(3) Uani 1 1 d . . . C19C C 0.3955(5) 0.5310(6) -0.0184(6) 0.122(4) Uani 1 1 d . . . H19G H 0.4134 0.5185 -0.0607 0.182 Uiso 1 1 calc R . . H19H H 0.3911 0.4819 0.0266 0.182 Uiso 1 1 calc R . . H19I H 0.4340 0.5549 -0.0055 0.182 Uiso 1 1 calc R . . C20C C 0.2258(6) 0.8148(6) -0.0987(5) 0.111(3) Uani 1 1 d . . . H20G H 0.2384 0.8442 -0.1518 0.166 Uiso 1 1 calc R . . H20H H 0.2634 0.8173 -0.0636 0.166 Uiso 1 1 calc R . . H20I H 0.1717 0.8387 -0.0922 0.166 Uiso 1 1 calc R . . C21C C 0.0937(5) 0.5912(6) -0.0792(6) 0.112(4) Uani 1 1 d . . . H21G H 0.0957 0.5802 -0.1239 0.167 Uiso 1 1 calc R . . H21H H 0.0464 0.6332 -0.0859 0.167 Uiso 1 1 calc R . . H21I H 0.0912 0.5427 -0.0327 0.167 Uiso 1 1 calc R . . Cl1D Cl 0.7761(2) -0.00626(17) 0.08784(16) 0.1378(12) Uani 1 1 d . . . N1D N 0.7509(4) -0.0776(5) -0.0006(5) 0.070(2) Uani 1 1 d . . . C1D C 0.7604(5) -0.0120(7) 0.0046(6) 0.070(3) Uani 1 1 d . . . N2D N 0.7651(4) 0.0460(5) -0.0657(5) 0.0623(19) Uani 1 1 d . . . C2D C 0.7483(5) -0.0598(7) -0.0781(6) 0.083(3) Uani 1 1 d . . . H2D H 0.7422 -0.0946 -0.0993 0.100 Uiso 1 1 calc R . . C3D C 0.7559(5) 0.0155(7) -0.1173(5) 0.080(3) Uani 1 1 d . . . H3D H 0.7552 0.0437 -0.1715 0.096 Uiso 1 1 calc R . . C4D C 0.7407(6) -0.1515(6) 0.0652(5) 0.066(2) Uani 1 1 d . . . C5D C 0.6607(6) -0.1597(6) 0.0803(6) 0.084(3) Uani 1 1 d . . . C6D C 0.6530(6) -0.2294(7) 0.1451(7) 0.096(3) Uani 1 1 d . . . H6D H 0.6012 -0.2374 0.1573 0.115 Uiso 1 1 calc R . . C7D C 0.7188(8) -0.2884(7) 0.1930(6) 0.093(3) Uani 1 1 d . . . C8D C 0.7947(6) -0.2769(6) 0.1754(6) 0.092(3) Uani 1 1 d . . . H8D H 0.8388 -0.3153 0.2083 0.111 Uiso 1 1 calc R . . C9D C 0.8091(5) -0.2096(6) 0.1097(6) 0.074(3) Uani 1 1 d . . . C10D C 0.5885(5) -0.0956(6) 0.0287(6) 0.118(4) Uani 1 1 d . . . H10J H 0.5969 -0.0425 0.0155 0.178 Uiso 1 1 calc R . . H10K H 0.5404 -0.1026 0.0562 0.178 Uiso 1 1 calc R . . H10L H 0.5824 -0.1011 -0.0185 0.178 Uiso 1 1 calc R . . C11D C 0.7058(6) -0.3608(6) 0.2669(6) 0.129(4) Uani 1 1 d . . . H11J H 0.6615 -0.3431 0.2923 0.194 Uiso 1 1 calc R . . H11K H 0.7541 -0.3841 0.3018 0.194 Uiso 1 1 calc R . . H11L H 0.6934 -0.4008 0.2534 0.194 Uiso 1 1 calc R . . C12D C 0.8938(5) -0.1983(6) 0.0908(6) 0.116(4) Uani 1 1 d . . . H12J H 0.9000 -0.1851 0.0365 0.174 Uiso 1 1 calc R . . H12K H 0.9324 -0.2478 0.1229 0.174 Uiso 1 1 calc R . . H12L H 0.9031 -0.1550 0.1009 0.174 Uiso 1 1 calc R . . C13D C 0.7716(6) 0.1287(5) -0.0848(4) 0.062(2) Uani 1 1 d . . . C14D C 0.8476(5) 0.1448(6) -0.0869(5) 0.071(3) Uani 1 1 d . . . C15D C 0.8506(5) 0.2230(6) -0.1051(5) 0.074(3) Uani 1 1 d . . . H15D H 0.9011 0.2356 -0.1085 0.089 Uiso 1 1 calc R . . C16D C 0.7823(6) 0.2842(6) -0.1186(5) 0.072(2) Uani 1 1 d . . . C17D C 0.7075(6) 0.2650(6) -0.1155(5) 0.077(3) Uani 1 1 d . . . H17D H 0.6606 0.3057 -0.1257 0.092 Uiso 1 1 calc R . . C18D C 0.7007(5) 0.1872(6) -0.0975(5) 0.073(3) Uani 1 1 d . . . C19D C 0.9245(5) 0.0798(5) -0.0708(5) 0.102(3) Uani 1 1 d . . . H19J H 0.9163 0.0286 -0.0319 0.153 Uiso 1 1 calc R . . H19K H 0.9678 0.0940 -0.0520 0.153 Uiso 1 1 calc R . . H19L H 0.9382 0.0757 -0.1182 0.153 Uiso 1 1 calc R . . C20D C 0.7882(5) 0.3698(5) -0.1380(5) 0.090(3) Uani 1 1 d . . . H20J H 0.7580 0.4071 -0.1871 0.136 Uiso 1 1 calc R . . H20K H 0.8440 0.3730 -0.1418 0.136 Uiso 1 1 calc R . . H20L H 0.7665 0.3836 -0.0974 0.136 Uiso 1 1 calc R . . C21D C 0.6170(5) 0.1678(5) -0.0897(5) 0.097(3) Uani 1 1 d . . . H21J H 0.6056 0.1537 -0.1304 0.145 Uiso 1 1 calc R . . H21K H 0.5768 0.2145 -0.0942 0.145 Uiso 1 1 calc R . . H21L H 0.6161 0.1229 -0.0395 0.145 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.102(2) 0.103(2) 0.145(3) -0.045(2) -0.0137(18) 0.0175(16) Al1 0.087(2) 0.089(2) 0.092(2) -0.033(2) -0.0032(18) 0.0002(17) Cl2 0.124(3) 0.139(3) 0.325(6) -0.069(4) -0.017(3) -0.044(2) Al2 0.116(3) 0.109(3) 0.096(3) -0.051(2) 0.024(2) -0.040(2) Cl3 0.116(2) 0.151(3) 0.107(2) -0.072(2) -0.0068(18) 0.0213(19) Al3 0.085(2) 0.084(2) 0.090(2) -0.0425(19) 0.0094(17) -0.0009(16) Cl4 0.145(3) 0.149(3) 0.092(2) -0.049(2) 0.0155(19) 0.022(2) Al4 0.116(2) 0.107(3) 0.081(2) -0.048(2) 0.0140(19) -0.035(2) Cl5 0.202(4) 0.173(4) 0.178(4) -0.063(3) -0.021(3) 0.047(3) Cl6 0.145(3) 0.128(3) 0.191(4) -0.034(3) 0.046(3) -0.036(2) Cl7 0.182(3) 0.296(5) 0.160(3) -0.160(4) 0.065(3) -0.094(3) Cl8 0.202(4) 0.239(4) 0.181(4) -0.122(3) 0.043(3) -0.133(3) Cl9 0.0902(18) 0.109(2) 0.114(2) -0.0428(19) 0.0005(16) 0.0066(15) Cl10 0.147(2) 0.138(3) 0.129(3) -0.093(2) 0.016(2) -0.002(2) Cl11 0.100(2) 0.101(2) 0.227(4) -0.059(3) 0.004(2) -0.0135(17) Cl12 0.152(3) 0.131(3) 0.081(2) -0.0411(19) 0.0143(18) 0.013(2) Cl13 0.199(4) 0.171(4) 0.238(5) -0.067(4) 0.051(3) 0.043(3) Cl14 0.258(4) 0.284(5) 0.078(2) -0.067(3) 0.032(3) -0.156(4) Cl15 0.123(2) 0.160(3) 0.141(3) -0.095(2) 0.0048(19) -0.061(2) Cl16 0.141(2) 0.150(3) 0.122(2) -0.069(2) 0.014(2) -0.076(2) Cl1A 0.0865(17) 0.145(2) 0.132(2) -0.110(2) 0.0184(16) -0.0319(16) N1A 0.073(5) 0.089(6) 0.065(5) -0.050(5) -0.004(4) -0.017(4) C1A 0.080(7) 0.076(7) 0.059(6) -0.042(5) 0.006(5) -0.024(5) N2A 0.077(6) 0.087(6) 0.059(5) -0.049(4) 0.014(4) -0.021(4) C2A 0.088(7) 0.134(9) 0.100(8) -0.087(8) 0.014(7) -0.033(7) C3A 0.079(7) 0.123(9) 0.102(8) -0.073(7) 0.002(6) -0.020(6) C4A 0.062(7) 0.097(9) 0.073(8) -0.054(7) 0.010(6) -0.020(6) C5A 0.068(7) 0.115(10) 0.082(9) -0.054(8) 0.007(7) -0.033(7) C6A 0.098(9) 0.121(11) 0.096(9) -0.052(8) 0.011(8) -0.044(8) C7A 0.068(8) 0.135(12) 0.129(12) -0.079(10) 0.022(9) -0.026(8) C8A 0.074(8) 0.105(10) 0.129(11) -0.077(9) -0.007(8) -0.005(7) C9A 0.073(7) 0.076(8) 0.090(9) -0.046(7) 0.000(7) -0.015(6) C10A 0.107(8) 0.142(10) 0.078(7) -0.032(7) 0.004(7) -0.050(8) C11A 0.079(8) 0.201(14) 0.253(16) -0.139(13) 0.042(9) -0.020(8) C12A 0.130(9) 0.091(9) 0.096(9) -0.042(7) -0.006(7) -0.021(7) C13A 0.060(6) 0.075(8) 0.069(7) -0.036(6) 0.004(6) -0.011(6) C14A 0.086(7) 0.083(9) 0.073(7) -0.031(7) -0.006(6) -0.023(6) C15A 0.092(8) 0.095(9) 0.082(8) -0.035(7) -0.017(6) -0.007(7) C16A 0.078(8) 0.085(9) 0.107(10) -0.052(8) 0.008(7) -0.018(7) C17A 0.079(7) 0.084(9) 0.091(8) -0.037(7) 0.022(6) -0.027(6) C18A 0.076(7) 0.065(8) 0.074(7) -0.025(6) 0.012(6) -0.019(6) C19A 0.111(8) 0.088(8) 0.095(8) -0.015(7) -0.022(6) -0.026(7) C20A 0.092(8) 0.186(13) 0.190(13) -0.102(11) -0.003(8) -0.051(8) C21A 0.121(8) 0.103(9) 0.086(8) 0.001(7) -0.011(7) -0.018(7) Cl1B 0.0882(17) 0.114(2) 0.114(2) -0.0819(19) 0.0015(15) -0.0123(15) N1B 0.092(6) 0.082(6) 0.075(6) -0.049(5) 0.015(5) -0.036(5) C1B 0.082(7) 0.069(7) 0.061(6) -0.039(5) 0.013(5) -0.027(6) N2B 0.074(6) 0.084(6) 0.069(5) -0.044(5) 0.010(4) -0.030(5) C2B 0.113(9) 0.123(10) 0.114(9) -0.085(8) 0.024(8) -0.057(8) C3B 0.096(8) 0.104(9) 0.114(9) -0.076(7) 0.030(7) -0.036(7) C4B 0.071(7) 0.088(9) 0.080(8) -0.049(7) -0.007(7) -0.008(7) C5B 0.089(9) 0.087(9) 0.080(9) -0.043(7) 0.001(7) -0.026(7) C6B 0.088(9) 0.128(11) 0.117(11) -0.069(9) 0.017(8) -0.030(8) C7B 0.096(10) 0.118(12) 0.123(12) -0.075(10) -0.003(9) -0.003(8) C8B 0.103(10) 0.128(11) 0.093(10) -0.044(9) -0.019(8) -0.012(8) C9B 0.097(9) 0.096(9) 0.087(9) -0.045(8) -0.002(8) -0.024(7) C10B 0.114(8) 0.112(10) 0.091(8) -0.008(8) 0.005(7) -0.028(7) C11B 0.081(8) 0.199(13) 0.197(13) -0.118(11) -0.021(8) 0.009(8) C12B 0.146(10) 0.147(11) 0.080(8) -0.023(8) -0.007(8) -0.021(8) C13B 0.067(7) 0.074(8) 0.066(7) -0.041(6) 0.013(6) -0.019(6) C14B 0.076(7) 0.094(9) 0.081(8) -0.042(8) 0.017(7) -0.024(7) C15B 0.095(9) 0.098(10) 0.072(8) -0.036(7) 0.004(7) -0.007(7) C16B 0.083(8) 0.100(10) 0.115(10) -0.066(9) 0.014(8) -0.018(8) C17B 0.098(8) 0.081(9) 0.096(9) -0.053(8) 0.035(7) -0.028(7) C18B 0.086(8) 0.085(9) 0.092(9) -0.059(8) 0.020(7) -0.031(7) C19B 0.121(9) 0.100(9) 0.106(9) -0.019(7) 0.012(7) -0.032(7) C20B 0.094(8) 0.152(11) 0.222(14) -0.127(11) -0.025(8) -0.010(7) C21B 0.159(10) 0.086(8) 0.070(7) -0.021(7) -0.001(7) -0.028(7) Cl1C 0.175(3) 0.086(2) 0.0654(17) -0.0367(16) -0.0067(17) -0.0013(18) N1C 0.083(5) 0.074(7) 0.077(7) -0.045(6) -0.005(5) -0.002(5) C1C 0.071(6) 0.085(9) 0.055(7) -0.033(7) -0.006(5) -0.001(6) N2C 0.081(5) 0.067(6) 0.055(5) -0.024(5) -0.005(4) -0.011(4) C2C 0.109(8) 0.110(10) 0.059(8) -0.032(7) -0.017(6) 0.011(7) C3C 0.102(7) 0.111(9) 0.055(7) -0.048(7) -0.007(6) -0.006(7) C4C 0.079(8) 0.071(8) 0.073(8) -0.028(7) -0.007(7) -0.002(7) C5C 0.072(8) 0.086(9) 0.102(9) -0.045(8) -0.003(7) 0.000(7) C6C 0.082(8) 0.105(10) 0.103(9) -0.053(8) 0.014(7) -0.026(7) C7C 0.098(9) 0.082(9) 0.076(8) -0.024(7) 0.000(7) -0.021(8) C8C 0.082(8) 0.085(9) 0.102(9) -0.028(8) -0.016(7) -0.015(7) C9C 0.082(8) 0.084(9) 0.078(8) -0.030(7) 0.003(7) -0.019(7) C10C 0.086(8) 0.136(10) 0.137(10) -0.040(9) -0.002(7) 0.002(7) C11C 0.154(10) 0.094(9) 0.101(9) -0.011(8) -0.004(8) -0.030(8) C12C 0.083(7) 0.089(8) 0.128(9) -0.017(7) 0.005(7) -0.007(6) C13C 0.076(7) 0.062(7) 0.046(6) -0.020(5) 0.000(5) -0.001(6) C14C 0.061(6) 0.069(8) 0.090(7) -0.040(6) -0.002(5) 0.001(6) C15C 0.072(7) 0.078(8) 0.073(7) -0.029(6) 0.011(5) -0.013(6) C16C 0.097(8) 0.074(8) 0.053(6) -0.025(6) 0.002(6) 0.002(7) C17C 0.085(8) 0.085(9) 0.056(6) -0.028(6) -0.008(6) 0.024(6) C18C 0.067(6) 0.081(8) 0.054(6) -0.035(6) -0.004(5) 0.002(6) C19C 0.062(6) 0.113(9) 0.186(11) -0.077(9) -0.023(7) 0.012(6) C20C 0.150(9) 0.082(9) 0.087(8) -0.034(7) -0.018(7) -0.003(7) C21C 0.065(6) 0.136(10) 0.147(10) -0.080(8) 0.000(6) -0.013(6) Cl1D 0.229(3) 0.109(2) 0.086(2) -0.0453(19) 0.026(2) -0.056(2) N1D 0.075(5) 0.066(6) 0.073(6) -0.031(5) 0.010(5) -0.020(4) C1D 0.080(6) 0.083(8) 0.054(7) -0.036(7) 0.011(5) -0.021(6) N2D 0.063(5) 0.065(6) 0.052(5) -0.023(5) 0.002(4) -0.008(4) C2D 0.105(7) 0.080(9) 0.058(7) -0.030(7) 0.000(6) -0.007(6) C3D 0.102(7) 0.076(8) 0.053(7) -0.021(7) -0.004(6) -0.021(6) C4D 0.068(7) 0.063(7) 0.071(7) -0.034(6) 0.015(6) -0.016(6) C5D 0.083(8) 0.073(8) 0.089(8) -0.029(7) 0.012(7) -0.022(6) C6D 0.082(8) 0.092(10) 0.119(10) -0.048(8) 0.024(8) -0.028(7) C7D 0.103(9) 0.091(9) 0.087(9) -0.036(8) 0.034(8) -0.038(8) C8D 0.085(8) 0.071(8) 0.093(9) -0.013(7) 0.005(7) -0.016(6) C9D 0.062(6) 0.082(8) 0.076(7) -0.032(6) 0.007(6) -0.022(6) C10D 0.067(6) 0.114(9) 0.132(9) -0.027(8) 0.003(7) 0.000(6) C11D 0.159(10) 0.108(10) 0.102(9) -0.021(8) 0.038(8) -0.054(8) C12D 0.079(7) 0.111(9) 0.124(9) -0.015(7) 0.008(7) -0.038(6) C13D 0.075(7) 0.052(7) 0.052(6) -0.021(5) 0.002(5) -0.003(5) C14D 0.061(6) 0.069(8) 0.076(7) -0.029(6) 0.006(5) -0.009(6) C15D 0.062(6) 0.078(8) 0.075(7) -0.026(6) 0.007(5) -0.016(6) C16D 0.084(7) 0.067(7) 0.065(6) -0.029(6) -0.004(6) -0.016(6) C17D 0.076(7) 0.069(8) 0.087(7) -0.038(6) 0.000(6) -0.011(6) C18D 0.065(7) 0.083(8) 0.074(7) -0.039(6) 0.009(5) -0.017(6) C19D 0.067(6) 0.082(8) 0.142(10) -0.044(7) 0.002(6) 0.003(5) C20D 0.110(8) 0.073(8) 0.083(7) -0.029(6) 0.019(6) -0.025(6) C21D 0.076(7) 0.094(8) 0.125(9) -0.055(7) 0.001(6) -0.013(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 Al1 2.127(4) . ? Al1 Cl2 2.088(4) . ? Al1 Cl4 2.097(4) . ? Al1 Cl3 2.114(4) . ? Al2 Cl5 2.074(5) . ? Al2 Cl8 2.091(4) . ? Al2 Cl7 2.101(4) . ? Al2 Cl6 2.102(4) . ? Al3 Cl12 2.100(4) . ? Al3 Cl10 2.105(4) . ? Al3 Cl11 2.109(4) . ? Al3 Cl9 2.137(4) . ? Al4 Cl13 2.069(5) . ? Al4 Cl14 2.090(4) . ? Al4 Cl15 2.107(4) . ? Al4 Cl16 2.121(4) . ? Cl1A C1A 1.658(8) . ? N1A C1A 1.324(8) . ? N1A C2A 1.399(9) . ? N1A C4A 1.462(10) . ? C1A N2A 1.341(9) . ? N2A C3A 1.395(9) . ? N2A C13A 1.449(9) . ? C2A C3A 1.338(10) . ? C4A C9A 1.375(11) . ? C4A C5A 1.374(12) . ? C5A C6A 1.385(11) . ? C5A C10A 1.498(12) . ? C6A C7A 1.380(13) . ? C7A C8A 1.380(13) . ? C7A C11A 1.527(12) . ? C8A C9A 1.373(12) . ? C9A C12A 1.494(11) . ? C13A C18A 1.371(11) . ? C13A C14A 1.387(11) . ? C14A C15A 1.417(11) . ? C14A C19A 1.518(11) . ? C15A C16A 1.373(12) . ? C16A C17A 1.350(12) . ? C16A C20A 1.518(12) . ? C17A C18A 1.401(11) . ? C18A C21A 1.525(11) . ? Cl1B C1B 1.672(8) . ? N1B C1B 1.325(9) . ? N1B C2B 1.389(10) . ? N1B C4B 1.435(10) . ? C1B N2B 1.332(9) . ? N2B C3B 1.377(9) . ? N2B C13B 1.424(10) . ? C2B C3B 1.327(10) . ? C4B C5B 1.357(12) . ? C4B C9B 1.380(12) . ? C5B C6B 1.388(12) . ? C5B C10B 1.495(12) . ? C6B C7B 1.370(13) . ? C7B C8B 1.364(13) . ? C7B C11B 1.547(13) . ? C8B C9B 1.385(13) . ? C9B C12B 1.511(12) . ? C13B C18B 1.377(11) . ? C13B C14B 1.391(11) . ? C14B C15B 1.400(12) . ? C14B C19B 1.511(11) . ? C15B C16B 1.370(12) . ? C16B C17B 1.392(12) . ? C16B C20B 1.535(12) . ? C17B C18B 1.405(11) . ? C18B C21B 1.489(11) . ? Cl1C C1C 1.684(9) . ? N1C C1C 1.346(10) . ? N1C C2C 1.373(10) . ? N1C C4C 1.459(10) . ? C1C N2C 1.305(9) . ? N2C C3C 1.408(9) . ? N2C C13C 1.461(10) . ? C2C C3C 1.358(11) . ? C4C C5C 1.367(12) . ? C4C C9C 1.381(11) . ? C5C C6C 1.378(12) . ? C5C C10C 1.497(11) . ? C6C C7C 1.351(12) . ? C7C C8C 1.378(12) . ? C7C C11C 1.500(12) . ? C8C C9C 1.366(11) . ? C9C C12C 1.530(11) . ? C13C C14C 1.382(10) . ? C13C C18C 1.388(10) . ? C14C C15C 1.369(10) . ? C14C C19C 1.504(10) . ? C15C C16C 1.379(11) . ? C16C C17C 1.372(11) . ? C16C C20C 1.535(11) . ? C17C C18C 1.398(11) . ? C18C C21C 1.499(10) . ? Cl1D C1D 1.670(9) . ? N1D C1D 1.323(9) . ? N1D C2D 1.364(10) . ? N1D C4D 1.447(10) . ? C1D N2D 1.317(9) . ? N2D C3D 1.364(9) . ? N2D C13D 1.463(9) . ? C2D C3D 1.313(10) . ? C4D C9D 1.394(10) . ? C4D C5D 1.405(11) . ? C5D C6D 1.378(12) . ? C5D C10D 1.516(11) . ? C6D C7D 1.390(12) . ? C7D C8D 1.360(11) . ? C7D C11D 1.520(12) . ? C8D C9D 1.396(11) . ? C9D C12D 1.509(10) . ? C13D C14D 1.382(10) . ? C13D C18D 1.385(10) . ? C14D C15D 1.367(10) . ? C14D C19D 1.510(10) . ? C15D C16D 1.382(10) . ? C16D C17D 1.384(10) . ? C16D C20D 1.510(10) . ? C17D C18D 1.380(10) . ? C18D C21D 1.527(10) . ? 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 Cl2 Al1 Cl4 111.5(2) . . ? Cl2 Al1 Cl3 106.98(19) . . ? Cl4 Al1 Cl3 108.11(17) . . ? Cl2 Al1 Cl1 110.51(19) . . ? Cl4 Al1 Cl1 108.96(17) . . ? Cl3 Al1 Cl1 110.78(17) . . ? Cl5 Al2 Cl8 112.0(2) . . ? Cl5 Al2 Cl7 111.5(2) . . ? Cl8 Al2 Cl7 108.99(19) . . ? Cl5 Al2 Cl6 110.6(2) . . ? Cl8 Al2 Cl6 108.3(2) . . ? Cl7 Al2 Cl6 105.1(2) . . ? Cl12 Al3 Cl10 108.68(18) . . ? Cl12 Al3 Cl11 111.82(19) . . ? Cl10 Al3 Cl11 108.23(16) . . ? Cl12 Al3 Cl9 109.92(15) . . ? Cl10 Al3 Cl9 109.16(17) . . ? Cl11 Al3 Cl9 108.97(17) . . ? Cl13 Al4 Cl14 111.5(2) . . ? Cl13 Al4 Cl15 110.2(2) . . ? Cl14 Al4 Cl15 109.1(2) . . ? Cl13 Al4 Cl16 110.0(2) . . ? Cl14 Al4 Cl16 109.42(19) . . ? Cl15 Al4 Cl16 106.50(16) . . ? C1A N1A C2A 106.4(7) . . ? C1A N1A C4A 126.3(7) . . ? C2A N1A C4A 127.1(7) . . ? N1A C1A N2A 110.1(7) . . ? N1A C1A Cl1A 124.5(7) . . ? N2A C1A Cl1A 125.4(7) . . ? C1A N2A C3A 108.2(7) . . ? C1A N2A C13A 126.4(7) . . ? C3A N2A C13A 125.2(8) . . ? C3A C2A N1A 109.3(8) . . ? C2A C3A N2A 106.0(8) . . ? C9A C4A C5A 124.7(10) . . ? C9A C4A N1A 118.5(10) . . ? C5A C4A N1A 116.6(10) . . ? C4A C5A C6A 117.1(11) . . ? C4A C5A C10A 124.4(10) . . ? C6A C5A C10A 118.5(11) . . ? C7A C6A C5A 120.0(11) . . ? C6A C7A C8A 120.4(11) . . ? C6A C7A C11A 120.3(13) . . ? C8A C7A C11A 119.3(13) . . ? C9A C8A C7A 121.2(11) . . ? C8A C9A C4A 116.4(10) . . ? C8A C9A C12A 122.5(11) . . ? C4A C9A C12A 121.0(10) . . ? C18A C13A C14A 125.1(9) . . ? C18A C13A N2A 118.9(9) . . ? C14A C13A N2A 116.0(9) . . ? C13A C14A C15A 114.2(9) . . ? C13A C14A C19A 123.5(9) . . ? C15A C14A C19A 122.3(10) . . ? C16A C15A C14A 123.2(10) . . ? C17A C16A C15A 118.6(10) . . ? C17A C16A C20A 121.0(11) . . ? C15A C16A C20A 120.4(12) . . ? C16A C17A C18A 122.6(10) . . ? C13A C18A C17A 116.4(9) . . ? C13A C18A C21A 123.0(10) . . ? C17A C18A C21A 120.6(10) . . ? C1B N1B C2B 106.5(8) . . ? C1B N1B C4B 125.6(8) . . ? C2B N1B C4B 127.8(8) . . ? N1B C1B N2B 110.9(7) . . ? N1B C1B Cl1B 124.5(8) . . ? N2B C1B Cl1B 124.5(8) . . ? C1B N2B C3B 106.3(7) . . ? C1B N2B C13B 127.6(8) . . ? C3B N2B C13B 126.1(8) . . ? C3B C2B N1B 107.7(8) . . ? C2B C3B N2B 108.6(8) . . ? C5B C4B C9B 123.9(10) . . ? C5B C4B N1B 118.2(11) . . ? C9B C4B N1B 117.9(12) . . ? C4B C5B C6B 117.6(11) . . ? C4B C5B C10B 121.0(10) . . ? C6B C5B C10B 121.4(12) . . ? C7B C6B C5B 120.2(12) . . ? C8B C7B C6B 120.6(12) . . ? C8B C7B C11B 119.4(14) . . ? C6B C7B C11B 120.0(14) . . ? C7B C8B C9B 120.8(12) . . ? C4B C9B C8B 116.8(11) . . ? C4B C9B C12B 121.3(11) . . ? C8B C9B C12B 121.9(12) . . ? C18B C13B C14B 123.6(10) . . ? C18B C13B N2B 118.0(10) . . ? C14B C13B N2B 118.4(10) . . ? C13B C14B C15B 117.9(10) . . ? C13B C14B C19B 123.1(10) . . ? C15B C14B C19B 119.0(11) . . ? C16B C15B C14B 121.2(11) . . ? C15B C16B C17B 118.4(11) . . ? C15B C16B C20B 121.5(13) . . ? C17B C16B C20B 120.1(12) . . ? C16B C17B C18B 123.1(10) . . ? C13B C18B C17B 115.7(10) . . ? C13B C18B C21B 122.7(10) . . ? C17B C18B C21B 121.4(10) . . ? C1C N1C C2C 108.1(9) . . ? C1C N1C C4C 124.6(9) . . ? C2C N1C C4C 127.1(9) . . ? N2C C1C N1C 110.9(8) . . ? N2C C1C Cl1C 124.1(9) . . ? N1C C1C Cl1C 125.0(9) . . ? C1C N2C C3C 106.5(8) . . ? C1C N2C C13C 126.2(8) . . ? C3C N2C C13C 127.2(9) . . ? C3C C2C N1C 106.4(9) . . ? C2C C3C N2C 108.1(9) . . ? C5C C4C C9C 124.0(10) . . ? C5C C4C N1C 119.7(10) . . ? C9C C4C N1C 116.3(10) . . ? C4C C5C C6C 115.3(9) . . ? C4C C5C C10C 123.9(11) . . ? C6C C5C C10C 120.8(11) . . ? C7C C6C C5C 124.4(11) . . ? C6C C7C C8C 117.0(11) . . ? C6C C7C C11C 123.1(12) . . ? C8C C7C C11C 119.8(11) . . ? C9C C8C C7C 122.7(10) . . ? C8C C9C C4C 116.5(10) . . ? C8C C9C C12C 121.0(10) . . ? C4C C9C C12C 122.4(10) . . ? C14C C13C C18C 123.5(9) . . ? C14C C13C N2C 118.8(8) . . ? C18C C13C N2C 117.7(9) . . ? C15C C14C C13C 116.5(8) . . ? C15C C14C C19C 121.7(9) . . ? C13C C14C C19C 121.8(9) . . ? C14C C15C C16C 123.4(9) . . ? C17C C16C C15C 118.0(10) . . ? C17C C16C C20C 120.7(9) . . ? C15C C16C C20C 121.3(10) . . ? C16C C17C C18C 121.9(9) . . ? C13C C18C C17C 116.6(9) . . ? C13C C18C C21C 122.0(9) . . ? C17C C18C C21C 121.4(9) . . ? C1D N1D C2D 107.3(8) . . ? C1D N1D C4D 124.6(9) . . ? C2D N1D C4D 128.0(9) . . ? N2D C1D N1D 110.1(8) . . ? N2D C1D Cl1D 124.1(9) . . ? N1D C1D Cl1D 125.5(9) . . ? C1D N2D C3D 106.3(8) . . ? C1D N2D C13D 126.5(8) . . ? C3D N2D C13D 127.0(8) . . ? C3D C2D N1D 107.2(9) . . ? C2D C3D N2D 109.1(9) . . ? C9D C4D C5D 124.0(9) . . ? C9D C4D N1D 119.2(9) . . ? C5D C4D N1D 116.8(9) . . ? C6D C5D C4D 115.3(10) . . ? C6D C5D C10D 122.9(10) . . ? C4D C5D C10D 121.8(9) . . ? C5D C6D C7D 123.4(10) . . ? C8D C7D C6D 118.5(10) . . ? C8D C7D C11D 120.8(11) . . ? C6D C7D C11D 120.6(11) . . ? C7D C8D C9D 122.6(10) . . ? C4D C9D C8D 116.1(9) . . ? C4D C9D C12D 122.1(9) . . ? C8D C9D C12D 121.7(9) . . ? C14D C13D C18D 122.9(9) . . ? C14D C13D N2D 119.1(8) . . ? C18D C13D N2D 118.0(9) . . ? C15D C14D C13D 116.9(8) . . ? C15D C14D C19D 120.9(9) . . ? C13D C14D C19D 122.2(9) . . ? C14D C15D C16D 123.2(9) . . ? C15D C16D C17D 117.7(9) . . ? C15D C16D C20D 121.5(9) . . ? C17D C16D C20D 120.7(9) . . ? C18D C17D C16D 121.7(9) . . ? C17D C18D C13D 117.6(9) . . ? C17D C18D C21D 119.8(8) . . ? C13D C18D C21D 122.6(9) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 23.31 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.354 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.057