# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Marcus Cole' 'Sean G Alexander' 'Jonathan C Morris' _publ_contact_author_name 'Marcus Cole' _publ_contact_author_email M.COLE@UNSW.EDU.AU _publ_section_title ; Preparation of a Super Bulky Silver N-Heterocyclic Carbene Complex ; # Attachment 'Combined rev v2.cif' data_COMPOUND1 _database_code_depnum_ccdc_archive 'CCDC 717572' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common '[AgCl(IDitop)]' _chemical_melting_point >588 _chemical_formula_moiety 'C43 H36 Ag Cl N2' _chemical_formula_sum 'C43 H36 Ag Cl N2' _chemical_formula_weight 724.06 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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_int_tables_number 60 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 15.701(2) _cell_length_b 13.1938(16) _cell_length_c 16.310(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3378.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.710 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8711 _exptl_absorpt_correction_T_max 0.9654 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Apex' _diffrn_measurement_method 'psi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20798 _diffrn_reflns_av_R_equivalents 0.0636 _diffrn_reflns_av_sigmaI/netI 0.0540 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.94 _reflns_number_total 3748 _reflns_number_gt 3244 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS Collect Software' _computing_cell_refinement 'Bruker Scalepack' _computing_data_reduction X-Seed _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.0000P)^2^+41.6300P] 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 ? _refine_ls_number_reflns 3748 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1148 _refine_ls_R_factor_gt 0.0989 _refine_ls_wR_factor_ref 0.1637 _refine_ls_wR_factor_gt 0.1580 _refine_ls_goodness_of_fit_ref 1.227 _refine_ls_restrained_S_all 1.227 _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 Ag1 Ag 0.0000 0.61187(5) 0.2500 0.01653(17) Uani 1 2 d S . . Cl1 Cl 0.0000 0.43417(17) 0.2500 0.0327(6) Uani 1 2 d S . . N1 N -0.0031(4) 0.8328(4) 0.3157(3) 0.0135(10) Uani 1 1 d . . . C1 C 0.0000 0.7682(6) 0.2500 0.0148(16) Uani 1 2 d S . . C2 C -0.0024(5) 0.9335(4) 0.2906(3) 0.0157(12) Uani 1 1 d . . . H2 H -0.0050 0.9914 0.3251 0.019 Uiso 1 1 calc R . . C3 C -0.0064(4) 0.7990(4) 0.3996(4) 0.0129(11) Uani 1 1 d . . . C4 C -0.0720(4) 0.7348(5) 0.4240(4) 0.0115(12) Uani 1 1 d . . . C5 C -0.0685(4) 0.6951(5) 0.5022(4) 0.0157(13) Uiso 1 1 d . . . H5 H -0.1106 0.6472 0.5181 0.019 Uiso 1 1 calc R . . C6 C -0.0082(5) 0.7212(5) 0.5572(4) 0.0223(14) Uani 1 1 d . . . H6 H -0.0087 0.6934 0.6109 0.027 Uiso 1 1 calc R . . C7 C 0.0558(4) 0.7906(5) 0.5337(4) 0.0157(13) Uani 1 1 d . . . H7 H 0.0978 0.8109 0.5723 0.019 Uiso 1 1 calc R . . C8 C 0.0580(4) 0.8299(4) 0.4540(4) 0.0096(11) Uani 1 1 d . . . C9 C -0.1482(4) 0.7148(4) 0.3730(4) 0.0086(11) Uani 1 1 d . . . C10 C -0.1753(4) 0.6178(5) 0.3548(4) 0.0170(13) Uani 1 1 d . . . H10 H -0.1427 0.5615 0.3731 0.020 Uiso 1 1 calc R . . C11 C -0.2484(4) 0.6012(5) 0.3107(5) 0.0223(15) Uani 1 1 d . . . H11 H -0.2653 0.5338 0.2981 0.027 Uiso 1 1 calc R . . C12 C -0.2981(4) 0.6820(5) 0.2844(4) 0.0166(13) Uani 1 1 d . . . C13 C -0.2730(4) 0.7796(5) 0.3051(4) 0.0144(13) Uani 1 1 d . . . H13 H -0.3081 0.8356 0.2910 0.017 Uiso 1 1 calc R . . C14 C -0.1975(4) 0.7955(5) 0.3458(4) 0.0106(12) Uani 1 1 d . . . H14 H -0.1787 0.8629 0.3556 0.013 Uiso 1 1 calc R . . C15 C -0.3784(4) 0.6655(5) 0.2345(4) 0.0229(15) Uiso 1 1 d . . . H15A H -0.3894 0.5926 0.2293 0.034 Uiso 1 1 calc R . . H15B H -0.3711 0.6951 0.1799 0.034 Uiso 1 1 calc R . . H15C H -0.4266 0.6980 0.2621 0.034 Uiso 1 1 calc R . . C16 C 0.1288(4) 0.9005(5) 0.4341(4) 0.0115(12) Uani 1 1 d . . . C17 C 0.1922(4) 0.8740(5) 0.3804(4) 0.0174(13) Uani 1 1 d . . . H17 H 0.1873 0.8130 0.3498 0.021 Uiso 1 1 calc R . . C18 C 0.2641(4) 0.9353(5) 0.3700(4) 0.0158(13) Uani 1 1 d . . . H18 H 0.3075 0.9151 0.3329 0.019 Uiso 1 1 calc R . . C19 C 0.2726(4) 1.0255(5) 0.4135(4) 0.0166(13) Uani 1 1 d . . . C20 C 0.2062(5) 1.0528(5) 0.4650(4) 0.0215(15) Uani 1 1 d . . . H20 H 0.2094 1.1153 0.4937 0.026 Uiso 1 1 calc R . . C21 C 0.1357(4) 0.9919(5) 0.4759(4) 0.0179(14) Uani 1 1 d . . . H21 H 0.0917 1.0125 0.5122 0.021 Uiso 1 1 calc R . . C22 C 0.3501(5) 1.0883(6) 0.4037(5) 0.0293(18) Uani 1 1 d . . . H22A H 0.3468 1.1471 0.4402 0.044 Uiso 1 1 calc R . . H22B H 0.3544 1.1115 0.3467 0.044 Uiso 1 1 calc R . . H22C H 0.4005 1.0479 0.4175 0.044 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 Ag1 0.0246(3) 0.0118(3) 0.0132(3) 0.000 0.0020(4) 0.000 Cl1 0.0556(16) 0.0149(10) 0.0277(13) 0.000 0.0003(16) 0.000 N1 0.013(2) 0.019(2) 0.008(2) 0.0004(19) 0.001(2) -0.005(2) C1 0.015(4) 0.011(3) 0.018(4) 0.000 -0.002(4) 0.000 C2 0.020(3) 0.016(3) 0.011(3) -0.006(2) 0.003(3) -0.006(3) C3 0.010(3) 0.016(3) 0.012(3) 0.001(2) -0.004(3) 0.005(3) C4 0.014(3) 0.013(3) 0.008(3) 0.003(2) 0.005(2) 0.005(2) C6 0.020(3) 0.037(4) 0.011(3) 0.005(3) 0.011(3) 0.006(3) C7 0.015(3) 0.029(4) 0.003(3) 0.004(2) 0.000(2) 0.009(3) C8 0.013(3) 0.011(3) 0.005(3) -0.001(2) -0.002(2) 0.007(2) C9 0.013(3) 0.009(3) 0.004(3) 0.001(2) 0.002(2) 0.002(2) C10 0.016(3) 0.013(3) 0.022(3) 0.000(3) 0.001(3) 0.004(3) C11 0.022(3) 0.016(3) 0.029(4) -0.004(3) 0.012(3) -0.007(3) C12 0.013(3) 0.021(3) 0.016(3) 0.000(3) 0.001(3) -0.005(2) C13 0.012(3) 0.017(3) 0.015(3) 0.003(3) -0.001(2) 0.003(2) C14 0.009(3) 0.014(3) 0.008(3) 0.001(2) 0.000(2) -0.002(2) C16 0.013(3) 0.012(3) 0.010(3) -0.005(2) -0.003(2) 0.001(2) C17 0.023(3) 0.010(3) 0.019(3) -0.005(3) 0.002(3) -0.004(3) C18 0.018(3) 0.018(3) 0.011(3) -0.004(3) 0.001(3) -0.005(3) C19 0.019(3) 0.020(3) 0.011(3) 0.001(3) -0.005(3) -0.003(3) C20 0.030(4) 0.020(3) 0.015(3) -0.010(3) 0.000(3) -0.001(3) C21 0.019(3) 0.024(3) 0.011(3) -0.011(3) 0.004(2) -0.002(3) C22 0.028(4) 0.034(4) 0.027(4) -0.003(3) 0.001(3) -0.019(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 C1 2.062(8) . ? Ag1 Cl1 2.345(2) . ? N1 C1 1.371(7) . ? N1 C2 1.390(7) . ? N1 C3 1.439(7) . ? C1 N1 1.371(7) 4 ? C2 C2 1.326(11) 4 ? C3 C4 1.392(9) . ? C3 C8 1.405(8) . ? C4 C5 1.380(9) . ? C4 C9 1.481(8) . ? C5 C6 1.350(10) . ? C6 C7 1.412(10) . ? C7 C8 1.401(8) . ? C8 C16 1.485(8) . ? C9 C10 1.381(8) . ? C9 C14 1.389(8) . ? C10 C11 1.373(10) . ? C11 C12 1.389(10) . ? C12 C13 1.388(9) . ? C12 C15 1.516(9) . ? C13 C14 1.376(8) . ? C16 C17 1.372(9) . ? C16 C21 1.389(8) . ? C17 C18 1.398(9) . ? C18 C19 1.392(9) . ? C19 C20 1.387(9) . ? C19 C22 1.481(9) . ? C20 C21 1.379(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 Ag1 Cl1 180.000(1) . . ? C1 N1 C2 111.3(5) . . ? C1 N1 C3 123.5(5) . . ? C2 N1 C3 125.2(5) . . ? N1 C1 N1 103.1(7) . 4 ? N1 C1 Ag1 128.5(3) . . ? N1 C1 Ag1 128.5(3) 4 . ? C2 C2 N1 107.2(3) 4 . ? C4 C3 C8 121.9(6) . . ? C4 C3 N1 119.2(6) . . ? C8 C3 N1 118.9(6) . . ? C5 C4 C3 117.8(6) . . ? C5 C4 C9 118.9(6) . . ? C3 C4 C9 123.1(5) . . ? C6 C5 C4 123.0(6) . . ? C5 C6 C7 119.0(6) . . ? C8 C7 C6 120.7(6) . . ? C7 C8 C3 117.4(6) . . ? C7 C8 C16 116.9(6) . . ? C3 C8 C16 125.6(5) . . ? C10 C9 C14 118.1(6) . . ? C10 C9 C4 122.4(5) . . ? C14 C9 C4 119.5(5) . . ? C11 C10 C9 121.2(6) . . ? C10 C11 C12 120.6(6) . . ? C13 C12 C11 118.5(6) . . ? C13 C12 C15 120.0(6) . . ? C11 C12 C15 121.5(6) . . ? C14 C13 C12 120.3(6) . . ? C13 C14 C9 121.1(6) . . ? C17 C16 C21 118.5(6) . . ? C17 C16 C8 121.5(5) . . ? C21 C16 C8 119.7(6) . . ? C16 C17 C18 121.1(6) . . ? C19 C18 C17 120.7(6) . . ? C20 C19 C18 117.3(6) . . ? C20 C19 C22 122.5(6) . . ? C18 C19 C22 120.2(6) . . ? C21 C20 C19 122.0(6) . . ? C20 C21 C16 120.3(6) . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.779 _refine_diff_density_min -2.588 _refine_diff_density_rms 0.146 _chemical_compound_source dichloromethane-hexane #===END data_COMPOUND2 _database_code_depnum_ccdc_archive 'CCDC 717573' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common '[AgCl(IBp)].CH2Cl2' _chemical_melting_point 408-410 _chemical_formula_moiety 'C27 H20 Ag Cl N2, C H2 Cl2' _chemical_formula_sum 'C27 H20 Ag Cl N2, C H2 Cl2' _chemical_formula_weight 600.70 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' 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' Ag Ag -0.8971 1.1015 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4785(19) _cell_length_b 10.348(2) _cell_length_c 14.088(3) _cell_angle_alpha 69.73(3) _cell_angle_beta 76.14(3) _cell_angle_gamma 82.22(3) _cell_volume 1256.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.588 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 1.141 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8039 _exptl_absorpt_correction_T_max 0.9451 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Apex' _diffrn_measurement_method 'psi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21644 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 27.99 _reflns_number_total 5938 _reflns_number_gt 5476 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS Collect Software' _computing_cell_refinement 'Bruker Scalepack' _computing_data_reduction X-Seed _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.0332P)^2^+1.9470P] 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 constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5938 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0343 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0791 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ag1 Ag 0.876094(18) 0.988086(16) 0.623256(13) 0.01843(6) Uani 1 1 d . . . Cl1 Cl 0.96757(6) 1.19961(5) 0.51143(4) 0.02102(12) Uani 1 1 d . . . Cl2 Cl 0.31369(15) 0.93471(15) 1.09744(17) 0.1144(7) Uani 1 1 d . . . Cl3 Cl 0.49860(9) 0.70776(8) 1.05494(7) 0.04333(18) Uani 1 1 d . . . N1 N 0.84461(19) 0.70818(18) 0.80289(14) 0.0136(3) Uani 1 1 d . . . N2 N 0.6512(2) 0.76542(18) 0.74174(14) 0.0143(3) Uani 1 1 d . . . C1 C 0.7826(2) 0.8114(2) 0.73198(16) 0.0144(4) Uani 1 1 d . . . C2 C 0.7529(2) 0.6006(2) 0.85538(17) 0.0162(4) Uani 1 1 d . . . H2 H 0.7720 0.5179 0.9083 0.019 Uiso 1 1 calc R . . C3 C 0.6316(2) 0.6367(2) 0.81649(17) 0.0168(4) Uani 1 1 d . . . H3 H 0.5484 0.5840 0.8364 0.020 Uiso 1 1 calc R . . C4 C 0.9828(2) 0.7140(2) 0.82573(16) 0.0135(4) Uani 1 1 d . . . C5 C 1.0824(2) 0.5987(2) 0.83842(16) 0.0141(4) Uani 1 1 d . . . C6 C 1.2079(2) 0.6076(2) 0.87060(17) 0.0181(4) Uani 1 1 d . . . H6 H 1.2754 0.5299 0.8828 0.022 Uiso 1 1 calc R . . C7 C 1.2373(3) 0.7261(3) 0.88524(18) 0.0204(4) Uani 1 1 d . . . H7 H 1.3242 0.7293 0.9066 0.024 Uiso 1 1 calc R . . C8 C 1.1395(3) 0.8399(2) 0.86864(18) 0.0203(4) Uani 1 1 d . . . H8 H 1.1604 0.9224 0.8766 0.024 Uiso 1 1 calc R . . C9 C 1.0113(3) 0.8330(2) 0.84049(17) 0.0178(4) Uani 1 1 d . . . H9 H 0.9426 0.9099 0.8312 0.021 Uiso 1 1 calc R . . C10 C 1.0640(2) 0.4723(2) 0.81575(16) 0.0152(4) Uani 1 1 d . . . C11 C 1.0370(2) 0.4810(2) 0.72052(18) 0.0186(4) Uani 1 1 d . . . H11 H 1.0215 0.5687 0.6713 0.022 Uiso 1 1 calc R . . C12 C 1.0326(3) 0.3615(3) 0.69765(19) 0.0233(5) Uani 1 1 d . . . H12 H 1.0154 0.3679 0.6324 0.028 Uiso 1 1 calc R . . C13 C 1.0532(3) 0.2330(3) 0.7694(2) 0.0271(5) Uani 1 1 d . . . H13 H 1.0499 0.1516 0.7536 0.033 Uiso 1 1 calc R . . C14 C 1.0786(3) 0.2240(3) 0.8643(2) 0.0318(6) Uani 1 1 d . . . H14 H 1.0916 0.1361 0.9141 0.038 Uiso 1 1 calc R . . C15 C 1.0850(3) 0.3430(2) 0.88711(19) 0.0243(5) Uani 1 1 d . . . H15 H 1.1040 0.3361 0.9520 0.029 Uiso 1 1 calc R . . C16 C 0.5414(2) 0.8426(2) 0.68606(17) 0.0156(4) Uani 1 1 d . . . C17 C 0.4765(2) 0.7823(2) 0.63364(17) 0.0164(4) Uani 1 1 d . . . C18 C 0.3594(3) 0.8572(3) 0.59060(18) 0.0212(5) Uani 1 1 d . . . H18 H 0.3103 0.8174 0.5569 0.025 Uiso 1 1 calc R . . C19 C 0.3135(3) 0.9876(3) 0.5961(2) 0.0246(5) Uani 1 1 d . . . H19 H 0.2345 1.0369 0.5658 0.030 Uiso 1 1 calc R . . C20 C 0.3833(3) 1.0466(2) 0.6460(2) 0.0243(5) Uani 1 1 d . . . H20 H 0.3537 1.1372 0.6481 0.029 Uiso 1 1 calc R . . C21 C 0.4959(3) 0.9732(2) 0.69262(19) 0.0203(4) Uani 1 1 d . . . H21 H 0.5417 1.0119 0.7288 0.024 Uiso 1 1 calc R . . C22 C 0.5258(2) 0.6445(2) 0.62310(16) 0.0166(4) Uani 1 1 d . . . C23 C 0.6715(3) 0.6113(3) 0.58557(18) 0.0217(5) Uani 1 1 d . . . H23 H 0.7423 0.6773 0.5672 0.026 Uiso 1 1 calc R . . C24 C 0.7129(3) 0.4827(3) 0.5751(2) 0.0276(5) Uani 1 1 d . . . H24 H 0.8120 0.4613 0.5487 0.033 Uiso 1 1 calc R . . C25 C 0.6108(3) 0.3845(3) 0.6029(2) 0.0310(6) Uani 1 1 d . . . H25 H 0.6402 0.2958 0.5966 0.037 Uiso 1 1 calc R . . C26 C 0.4666(3) 0.4166(3) 0.6396(2) 0.0314(6) Uani 1 1 d . . . H26 H 0.3963 0.3498 0.6587 0.038 Uiso 1 1 calc R . . C27 C 0.4241(3) 0.5460(3) 0.64855(18) 0.0233(5) Uani 1 1 d . . . H27 H 0.3243 0.5680 0.6724 0.028 Uiso 1 1 calc R . . C28 C 0.3368(4) 0.7566(4) 1.1314(3) 0.0524(9) Uani 1 1 d . . . H28A H 0.2522 0.7199 1.1213 0.063 Uiso 1 1 calc R . . H28B H 0.3417 0.7165 1.2054 0.063 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 Ag1 0.01779(10) 0.01479(9) 0.02076(10) -0.00107(6) -0.00622(7) -0.00312(6) Cl1 0.0223(3) 0.0143(2) 0.0231(3) -0.0032(2) -0.0021(2) -0.0025(2) Cl2 0.0623(7) 0.0707(8) 0.2183(19) -0.0918(11) 0.0210(9) -0.0004(6) Cl3 0.0367(4) 0.0362(4) 0.0546(5) -0.0138(3) -0.0121(3) 0.0084(3) N1 0.0124(8) 0.0110(8) 0.0165(8) -0.0036(7) -0.0033(7) 0.0003(6) N2 0.0140(9) 0.0111(8) 0.0178(8) -0.0040(7) -0.0047(7) -0.0002(7) C1 0.0141(10) 0.0141(10) 0.0163(10) -0.0065(8) -0.0042(8) 0.0008(8) C2 0.0157(10) 0.0141(10) 0.0172(10) -0.0036(8) -0.0021(8) -0.0020(8) C3 0.0153(10) 0.0138(10) 0.0194(10) -0.0041(8) -0.0011(8) -0.0025(8) C4 0.0120(9) 0.0137(9) 0.0141(9) -0.0029(8) -0.0035(7) -0.0011(7) C5 0.0165(10) 0.0131(9) 0.0119(9) -0.0035(7) -0.0025(8) -0.0007(8) C6 0.0168(10) 0.0197(11) 0.0175(10) -0.0053(8) -0.0057(8) 0.0023(8) C7 0.0178(11) 0.0258(12) 0.0210(11) -0.0096(9) -0.0066(9) -0.0025(9) C8 0.0229(12) 0.0184(11) 0.0228(11) -0.0082(9) -0.0065(9) -0.0045(9) C9 0.0192(11) 0.0137(10) 0.0204(10) -0.0051(8) -0.0054(8) 0.0003(8) C10 0.0124(10) 0.0146(10) 0.0175(10) -0.0056(8) -0.0015(8) 0.0009(8) C11 0.0187(11) 0.0168(10) 0.0205(11) -0.0053(8) -0.0066(9) 0.0004(8) C12 0.0209(11) 0.0269(12) 0.0271(12) -0.0150(10) -0.0060(9) -0.0002(9) C13 0.0288(13) 0.0184(11) 0.0371(14) -0.0155(10) -0.0025(11) -0.0013(10) C14 0.0472(17) 0.0134(11) 0.0299(13) -0.0039(10) -0.0064(12) 0.0026(11) C15 0.0341(14) 0.0170(11) 0.0204(11) -0.0056(9) -0.0064(10) 0.0027(10) C16 0.0120(10) 0.0147(10) 0.0186(10) -0.0039(8) -0.0037(8) 0.0007(8) C17 0.0131(10) 0.0174(10) 0.0175(10) -0.0050(8) -0.0023(8) -0.0008(8) C18 0.0163(11) 0.0265(12) 0.0214(11) -0.0071(9) -0.0068(9) 0.0000(9) C19 0.0160(11) 0.0261(12) 0.0285(12) -0.0044(10) -0.0088(9) 0.0052(9) C20 0.0195(11) 0.0167(11) 0.0339(13) -0.0066(10) -0.0053(10) 0.0034(9) C21 0.0179(11) 0.0156(10) 0.0278(12) -0.0069(9) -0.0058(9) -0.0009(8) C22 0.0166(10) 0.0186(10) 0.0164(10) -0.0073(8) -0.0044(8) -0.0008(8) C23 0.0188(11) 0.0264(12) 0.0220(11) -0.0101(9) -0.0057(9) 0.0002(9) C24 0.0284(13) 0.0319(14) 0.0253(12) -0.0148(11) -0.0091(10) 0.0102(11) C25 0.0483(17) 0.0222(12) 0.0272(13) -0.0134(10) -0.0121(12) 0.0043(11) C26 0.0451(16) 0.0244(13) 0.0287(13) -0.0116(11) -0.0051(12) -0.0123(11) C27 0.0229(12) 0.0278(12) 0.0227(11) -0.0126(10) -0.0020(9) -0.0064(10) C28 0.051(2) 0.063(2) 0.0398(18) -0.0180(17) -0.0038(15) 0.0031(17) _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 Ag1 C1 2.079(2) . ? Ag1 Cl1 2.3440(11) . ? Cl2 C28 1.733(4) . ? Cl3 C28 1.773(4) . ? N1 C1 1.362(3) . ? N1 C2 1.387(3) . ? N1 C4 1.435(3) . ? N2 C1 1.352(3) . ? N2 C3 1.385(3) . ? N2 C16 1.438(3) . ? C2 C3 1.343(3) . ? C4 C9 1.389(3) . ? C4 C5 1.405(3) . ? C5 C6 1.396(3) . ? C5 C10 1.490(3) . ? C6 C7 1.386(3) . ? C7 C8 1.385(3) . ? C8 C9 1.383(3) . ? C10 C15 1.390(3) . ? C10 C11 1.396(3) . ? C11 C12 1.390(3) . ? C12 C13 1.385(4) . ? C13 C14 1.384(4) . ? C14 C15 1.389(3) . ? C16 C21 1.389(3) . ? C16 C17 1.398(3) . ? C17 C18 1.402(3) . ? C17 C22 1.485(3) . ? C18 C19 1.384(4) . ? C19 C20 1.390(4) . ? C20 C21 1.385(3) . ? C22 C27 1.394(3) . ? C22 C23 1.397(3) . ? C23 C24 1.384(4) . ? C24 C25 1.389(4) . ? C25 C26 1.380(4) . ? C26 C27 1.386(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ag1 Cl1 174.23(6) . . ? C1 N1 C2 111.41(18) . . ? C1 N1 C4 124.36(18) . . ? C2 N1 C4 124.09(18) . . ? C1 N2 C3 111.57(18) . . ? C1 N2 C16 124.72(18) . . ? C3 N2 C16 123.63(18) . . ? N2 C1 N1 103.79(18) . . ? N2 C1 Ag1 127.81(16) . . ? N1 C1 Ag1 128.10(16) . . ? C3 C2 N1 106.38(19) . . ? C2 C3 N2 106.84(19) . . ? C9 C4 C5 121.4(2) . . ? C9 C4 N1 118.23(19) . . ? C5 C4 N1 120.29(18) . . ? C6 C5 C4 116.83(19) . . ? C6 C5 C10 119.08(19) . . ? C4 C5 C10 124.04(19) . . ? C7 C6 C5 122.1(2) . . ? C8 C7 C6 119.8(2) . . ? C9 C8 C7 119.8(2) . . ? C8 C9 C4 120.1(2) . . ? C15 C10 C11 119.1(2) . . ? C15 C10 C5 119.7(2) . . ? C11 C10 C5 121.03(19) . . ? C12 C11 C10 120.1(2) . . ? C13 C12 C11 120.4(2) . . ? C14 C13 C12 119.7(2) . . ? C13 C14 C15 120.2(2) . . ? C14 C15 C10 120.5(2) . . ? C21 C16 C17 121.9(2) . . ? C21 C16 N2 117.89(19) . . ? C17 C16 N2 120.06(19) . . ? C16 C17 C18 117.2(2) . . ? C16 C17 C22 122.88(19) . . ? C18 C17 C22 119.9(2) . . ? C19 C18 C17 121.5(2) . . ? C18 C19 C20 119.9(2) . . ? C21 C20 C19 120.0(2) . . ? C20 C21 C16 119.4(2) . . ? C27 C22 C23 118.5(2) . . ? C27 C22 C17 119.5(2) . . ? C23 C22 C17 121.9(2) . . ? C24 C23 C22 120.2(2) . . ? C23 C24 C25 120.6(2) . . ? C26 C25 C24 119.6(2) . . ? C25 C26 C27 120.0(3) . . ? C26 C27 C22 121.0(2) . . ? Cl2 C28 Cl3 110.5(2) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 1.594 _refine_diff_density_min -1.225 _refine_diff_density_rms 0.086 _chemical_compound_source dichloromethane-hexane #===END data_DitopDAB _database_code_depnum_ccdc_archive 'CCDC 717574' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common DitopDAB _chemical_melting_point 481 _chemical_formula_moiety 'C42 H36 N2' _chemical_formula_sum 'C42 H36 N2' _chemical_formula_weight 568.764 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 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 14.4140(8) _cell_length_b 16.8693(10) _cell_length_c 6.3926(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.377(3) _cell_angle_gamma 90.00 _cell_volume 1554.35(15) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9930 _exptl_absorpt_correction_T_max 0.9930 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Apex' _diffrn_measurement_method 'psi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13663 _diffrn_reflns_av_R_equivalents 0.1345 _diffrn_reflns_av_sigmaI/netI 0.1733 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.17 _reflns_number_total 3727 _reflns_number_gt 1626 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS Collect Software' _computing_cell_refinement 'Bruker Scalepack' _computing_data_reduction X-Seed _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.0649P)^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 constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3727 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2219 _refine_ls_R_factor_gt 0.0796 _refine_ls_wR_factor_ref 0.1660 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _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 N1 N 1.06870(12) 0.07443(13) 0.3889(3) 0.0235(5) Uani 1 1 d . . . C1 C 1.01072(16) 0.01717(15) 0.3988(4) 0.0237(6) Uani 1 1 d . . . H1 H 0.9820 -0.0027 0.2752 0.028 Uiso 1 1 calc R . . C2 C 1.08843(16) 0.10843(15) 0.1906(4) 0.0218(6) Uani 1 1 d . . . C3 C 1.18230(16) 0.12047(15) 0.1418(4) 0.0232(6) Uani 1 1 d . . . C4 C 1.20431(17) 0.15147(15) -0.0545(4) 0.0271(7) Uani 1 1 d . . . H4 H 1.2676 0.1579 -0.0914 0.033 Uiso 1 1 calc R . . C5 C 1.13581(18) 0.17303(15) -0.1962(4) 0.0281(7) Uani 1 1 d . . . H5 H 1.1518 0.1922 -0.3310 0.034 Uiso 1 1 calc R . . C6 C 1.04387(17) 0.16633(15) -0.1392(4) 0.0255(6) Uani 1 1 d . . . H6 H 0.9971 0.1838 -0.2338 0.031 Uiso 1 1 calc R . . C7 C 1.01767(16) 0.13464(14) 0.0529(4) 0.0223(6) Uani 1 1 d . . . C8 C 1.25911(16) 0.10736(15) 0.2956(4) 0.0238(6) Uani 1 1 d . . . C9 C 1.26557(17) 0.04163(16) 0.4271(4) 0.0286(7) Uani 1 1 d . . . H9 H 1.2207 0.0006 0.4161 0.034 Uiso 1 1 calc R . . C10 C 1.33647(17) 0.03525(17) 0.5738(4) 0.0328(7) Uani 1 1 d . . . H10 H 1.3393 -0.0103 0.6611 0.039 Uiso 1 1 calc R . . C11 C 1.40367(17) 0.09409(17) 0.5958(4) 0.0320(7) Uani 1 1 d . . . C12 C 1.39816(17) 0.15873(17) 0.4636(4) 0.0310(7) Uani 1 1 d . . . H12 H 1.4436 0.1994 0.4738 0.037 Uiso 1 1 calc R . . C13 C 1.32761(16) 0.16533(16) 0.3165(4) 0.0286(7) Uani 1 1 d . . . H13 H 1.3258 0.2104 0.2276 0.034 Uiso 1 1 calc R . . C14 C 1.47889(18) 0.08699(19) 0.7620(5) 0.0482(9) Uani 1 1 d . . . H14A H 1.5185 0.1342 0.7584 0.072 Uiso 1 1 calc R . . H14B H 1.5165 0.0397 0.7348 0.072 Uiso 1 1 calc R . . H14C H 1.4502 0.0825 0.9001 0.072 Uiso 1 1 calc R . . C15 C 0.91755(16) 0.13630(14) 0.1099(4) 0.0221(6) Uani 1 1 d . . . C16 C 0.88863(17) 0.16847(15) 0.3005(4) 0.0255(7) Uani 1 1 d . . . H16 H 0.9337 0.1845 0.4011 0.031 Uiso 1 1 calc R . . C17 C 0.79520(16) 0.17732(15) 0.3447(4) 0.0271(7) Uani 1 1 d . . . H17 H 0.7774 0.1986 0.4760 0.033 Uiso 1 1 calc R . . C18 C 0.72716(17) 0.15570(16) 0.2011(4) 0.0296(7) Uani 1 1 d . . . C19 C 0.75529(17) 0.12195(16) 0.0140(4) 0.0327(7) Uani 1 1 d . . . H19 H 0.7099 0.1048 -0.0844 0.039 Uiso 1 1 calc R . . C20 C 0.84888(17) 0.11289(16) -0.0316(4) 0.0297(7) Uani 1 1 d . . . H20 H 0.8663 0.0903 -0.1617 0.036 Uiso 1 1 calc R . . C21 C 0.62590(17) 0.17031(17) 0.2481(5) 0.0424(8) Uani 1 1 d . . . H21A H 0.6105 0.2257 0.2177 0.064 Uiso 1 1 calc R . . H21B H 0.6142 0.1592 0.3961 0.064 Uiso 1 1 calc R . . H21C H 0.5874 0.1354 0.1611 0.064 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 N1 0.0211(11) 0.0260(13) 0.0236(13) 0.0018(10) 0.0021(9) -0.0013(10) C1 0.0219(14) 0.0225(16) 0.0266(16) -0.0009(12) 0.0026(11) 0.0030(12) C2 0.0260(14) 0.0198(15) 0.0196(15) -0.0018(12) 0.0028(11) -0.0025(12) C3 0.0232(14) 0.0200(15) 0.0264(16) -0.0009(12) 0.0030(11) -0.0002(12) C4 0.0259(15) 0.0263(17) 0.0291(17) -0.0032(13) 0.0078(12) -0.0039(12) C5 0.0374(16) 0.0273(16) 0.0196(16) -0.0021(12) 0.0074(13) -0.0019(13) C6 0.0339(16) 0.0245(16) 0.0181(15) -0.0008(12) 0.0006(12) 0.0002(12) C7 0.0271(15) 0.0191(15) 0.0208(15) -0.0029(12) 0.0022(12) -0.0011(12) C8 0.0220(14) 0.0232(15) 0.0263(16) -0.0020(13) 0.0051(11) 0.0026(12) C9 0.0240(14) 0.0290(17) 0.0330(17) -0.0042(13) 0.0028(12) -0.0018(13) C10 0.0280(15) 0.0333(18) 0.0371(19) 0.0026(14) 0.0002(13) 0.0056(14) C11 0.0202(14) 0.0423(19) 0.0335(18) -0.0045(15) 0.0012(12) 0.0033(14) C12 0.0199(15) 0.0364(19) 0.0366(18) -0.0060(14) 0.0027(13) -0.0050(13) C13 0.0254(15) 0.0288(17) 0.0316(18) -0.0001(13) 0.0068(12) -0.0006(13) C14 0.0325(16) 0.062(2) 0.050(2) -0.0006(17) -0.0079(14) -0.0005(16) C15 0.0241(14) 0.0204(15) 0.0217(15) 0.0001(12) -0.0032(11) -0.0002(12) C16 0.0302(16) 0.0221(16) 0.0242(16) -0.0002(12) -0.0009(12) -0.0016(12) C17 0.0314(15) 0.0247(16) 0.0254(16) 0.0013(12) 0.0076(12) 0.0024(13) C18 0.0251(15) 0.0282(17) 0.0354(18) 0.0035(13) -0.0002(13) 0.0013(12) C19 0.0271(15) 0.0363(19) 0.0345(18) -0.0044(14) -0.0070(12) 0.0007(13) C20 0.0310(16) 0.0323(17) 0.0259(16) -0.0036(13) 0.0021(12) 0.0010(13) C21 0.0310(16) 0.043(2) 0.053(2) 0.0016(16) 0.0052(15) 0.0058(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.279(3) . ? N1 C2 1.421(3) . ? C1 C1 1.453(5) 3_756 ? C2 C3 1.405(3) . ? C2 C7 1.414(3) . ? C3 C4 1.398(3) . ? C3 C8 1.493(3) . ? C4 C5 1.384(3) . ? C5 C6 1.381(3) . ? C6 C7 1.394(3) . ? C7 C15 1.491(3) . ? C8 C9 1.394(4) . ? C8 C13 1.395(3) . ? C9 C10 1.386(3) . ? C10 C11 1.393(4) . ? C11 C12 1.381(4) . ? C11 C14 1.518(4) . ? C12 C13 1.385(3) . ? C15 C20 1.393(3) . ? C15 C16 1.400(3) . ? C16 C17 1.386(3) . ? C17 C18 1.388(3) . ? C18 C19 1.387(4) . ? C18 C21 1.512(3) . ? C19 C20 1.390(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 118.9(2) . . ? N1 C1 C1 119.2(3) . 3_756 ? C3 C2 C7 120.5(2) . . ? C3 C2 N1 117.1(2) . . ? C7 C2 N1 122.3(2) . . ? C4 C3 C2 118.6(2) . . ? C4 C3 C8 118.4(2) . . ? C2 C3 C8 122.9(2) . . ? C5 C4 C3 121.4(2) . . ? C6 C5 C4 119.2(2) . . ? C5 C6 C7 122.0(2) . . ? C6 C7 C2 118.1(2) . . ? C6 C7 C15 118.4(2) . . ? C2 C7 C15 123.3(2) . . ? C9 C8 C13 117.1(2) . . ? C9 C8 C3 124.2(2) . . ? C13 C8 C3 118.7(2) . . ? C10 C9 C8 121.0(2) . . ? C9 C10 C11 121.5(3) . . ? C12 C11 C10 117.6(2) . . ? C12 C11 C14 121.9(2) . . ? C10 C11 C14 120.5(3) . . ? C11 C12 C13 121.2(3) . . ? C12 C13 C8 121.6(3) . . ? C20 C15 C16 117.4(2) . . ? C20 C15 C7 121.4(2) . . ? C16 C15 C7 120.9(2) . . ? C17 C16 C15 121.0(2) . . ? C16 C17 C18 121.3(2) . . ? C19 C18 C17 118.0(2) . . ? C19 C18 C21 121.7(2) . . ? C17 C18 C21 120.3(3) . . ? C18 C19 C20 121.0(2) . . ? C19 C20 C15 121.2(3) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 28.17 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.273 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.064 _chemical_compound_source ethanol #===END