# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Brasse, Mikael' 'Ellman, Jonathan' 'Bergman, Robert' _publ_contact_author_name 'Bergman, Robert' _publ_contact_author_email rbergman@berkeley.edu _publ_section_title ; A Facile, Metal- and Solvent Free, Autoxidative Coupling of Quinolines with Indoles and Pyrroles ; # Attachment '- XrayComp3a.cif' data_bergman03 _database_code_depnum_ccdc_archive 'CCDC 809741' #TrackingRef '- XrayComp3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bergman03 ; _chemical_name_common MB-I-47 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 N2' _chemical_formula_weight 258.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.7173(3) _cell_length_b 8.8634(3) _cell_length_c 19.0154(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.350(2) _cell_angle_gamma 90.00 _cell_volume 1298.46(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9939 _cell_measurement_theta_min 4.66 _cell_measurement_theta_max 67.48 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.608 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9306 _exptl_absorpt_correction_T_max 0.9761 _exptl_absorpt_process_details SADABS _diffrn_refln_scan_width 0.5 _diffrn_refln_scan_rate 5 _space_group.centring_type primitive _space_group.IT_number 14 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'microfocus rotating anode' _diffrn_radiation_monochromator 'HELIOS multilayer mirrors' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_reflns_number 16829 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0104 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.66 _diffrn_reflns_theta_max 67.95 _reflns_number_total 2304 _reflns_number_gt 2119 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR-2004 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics ORTEP-32 _computing_publication_material WinGX _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^)+(0.0425P)^2^+0.4587P] 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 2304 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0349 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0865 _refine_ls_wR_factor_gt 0.0837 _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 C1 C 0.37654(14) 0.03967(12) 0.73146(6) 0.0229(3) Uani 1 1 d . . . C2 C 0.42712(15) -0.04120(13) 0.79466(6) 0.0253(3) Uani 1 1 d . . . H2 H 0.5367 -0.0902 0.7991 0.030 Uiso 1 1 calc R . . C3 C 0.31839(15) -0.04766(13) 0.84800(6) 0.0255(3) Uani 1 1 d . . . H3 H 0.3525 -0.0993 0.8903 0.031 Uiso 1 1 calc R . . C4 C 0.15357(15) 0.02294(13) 0.84042(6) 0.0238(3) Uani 1 1 d . . . C5 C 0.02842(15) 0.01345(14) 0.89139(6) 0.0269(3) Uani 1 1 d . . . H5 H 0.0539 -0.0417 0.9336 0.032 Uiso 1 1 calc R . . C6 C -0.12951(15) 0.08289(14) 0.88067(6) 0.0291(3) Uani 1 1 d . . . H6 H -0.2133 0.0751 0.9152 0.035 Uiso 1 1 calc R . . C7 C -0.16769(15) 0.16588(14) 0.81840(6) 0.0293(3) Uani 1 1 d . . . H7 H -0.2767 0.2152 0.8115 0.035 Uiso 1 1 calc R . . C8 C -0.04921(15) 0.17612(14) 0.76777(6) 0.0274(3) Uani 1 1 d . . . H8 H -0.0767 0.2325 0.7261 0.033 Uiso 1 1 calc R . . C9 C 0.11395(14) 0.10346(13) 0.77690(6) 0.0236(3) Uani 1 1 d . . . C10 C 0.65117(15) -0.02479(13) 0.67159(6) 0.0252(3) Uani 1 1 d . . . H10 H 0.7008 -0.0879 0.7078 0.030 Uiso 1 1 calc R . . C11 C 0.49207(14) 0.04519(13) 0.67355(6) 0.0235(3) Uani 1 1 d . . . C12 C 0.46839(14) 0.12780(13) 0.60822(6) 0.0227(3) Uani 1 1 d . . . C13 C 0.33820(15) 0.22221(13) 0.57841(6) 0.0251(3) Uani 1 1 d . . . H13 H 0.2362 0.2420 0.6025 0.030 Uiso 1 1 calc R . . C14 C 0.36125(15) 0.28600(14) 0.51326(6) 0.0279(3) Uani 1 1 d . . . H14 H 0.2740 0.3508 0.4929 0.033 Uiso 1 1 calc R . . C15 C 0.51002(15) 0.25749(14) 0.47657(6) 0.0283(3) Uani 1 1 d . . . H15 H 0.5208 0.3020 0.4316 0.034 Uiso 1 1 calc R . . C16 C 0.64133(15) 0.16590(13) 0.50458(6) 0.0260(3) Uani 1 1 d . . . H16 H 0.7428 0.1469 0.4801 0.031 Uiso 1 1 calc R . . C17 C 0.61815(14) 0.10245(13) 0.57064(6) 0.0239(3) Uani 1 1 d . . . C18 C 0.89901(15) -0.03900(15) 0.59237(7) 0.0316(3) Uani 1 1 d . . . H18A H 0.9434 -0.1154 0.6261 0.047 Uiso 1 1 calc R . . H18B H 0.9774 0.0480 0.5938 0.047 Uiso 1 1 calc R . . H18C H 0.8919 -0.0820 0.5448 0.047 Uiso 1 1 calc R . . N1 N 0.22573(12) 0.11186(11) 0.72365(5) 0.0243(2) Uani 1 1 d . . . N2 N 0.72748(12) 0.00888(11) 0.61076(5) 0.0258(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0248(6) 0.0185(6) 0.0251(6) -0.0019(4) -0.0021(4) -0.0023(4) C2 0.0248(6) 0.0238(6) 0.0269(6) 0.0007(5) -0.0010(5) 0.0011(4) C3 0.0296(6) 0.0225(6) 0.0240(6) 0.0020(4) -0.0025(5) -0.0004(5) C4 0.0269(6) 0.0198(6) 0.0244(6) -0.0024(4) -0.0010(4) -0.0035(4) C5 0.0309(6) 0.0235(6) 0.0263(6) -0.0005(5) 0.0009(5) -0.0038(5) C6 0.0288(6) 0.0270(7) 0.0319(6) -0.0031(5) 0.0053(5) -0.0045(5) C7 0.0245(6) 0.0272(7) 0.0359(7) -0.0030(5) -0.0005(5) 0.0005(5) C8 0.0279(6) 0.0256(6) 0.0281(6) 0.0010(5) -0.0024(5) 0.0001(5) C9 0.0254(6) 0.0200(6) 0.0251(6) -0.0021(4) -0.0014(4) -0.0028(4) C10 0.0285(6) 0.0237(6) 0.0230(6) 0.0003(4) -0.0015(5) 0.0008(5) C11 0.0254(6) 0.0213(6) 0.0234(6) -0.0013(4) -0.0020(4) -0.0014(4) C12 0.0247(6) 0.0204(6) 0.0229(5) -0.0026(4) -0.0012(4) -0.0034(4) C13 0.0253(6) 0.0237(6) 0.0259(6) -0.0018(5) -0.0014(4) -0.0006(5) C14 0.0302(6) 0.0261(6) 0.0267(6) 0.0018(5) -0.0039(5) 0.0004(5) C15 0.0345(6) 0.0276(7) 0.0225(6) 0.0006(5) -0.0007(5) -0.0046(5) C16 0.0280(6) 0.0257(6) 0.0245(6) -0.0036(5) 0.0028(5) -0.0028(5) C17 0.0259(6) 0.0210(6) 0.0246(6) -0.0038(4) -0.0012(4) -0.0020(4) C18 0.0270(6) 0.0368(7) 0.0313(6) 0.0000(5) 0.0028(5) 0.0055(5) N1 0.0256(5) 0.0233(5) 0.0236(5) 0.0004(4) -0.0005(4) -0.0004(4) N2 0.0256(5) 0.0266(5) 0.0251(5) -0.0013(4) 0.0011(4) 0.0018(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 C1 N1 1.3288(15) . ? C1 C2 1.4339(16) . ? C1 C11 1.4575(16) . ? C2 C3 1.3548(16) . ? C2 H2 0.9500 . ? C3 C4 1.4173(16) . ? C3 H3 0.9500 . ? C4 C5 1.4101(16) . ? C4 C9 1.4209(16) . ? C5 C6 1.3699(17) . ? C5 H5 0.9500 . ? C6 C7 1.4105(17) . ? C6 H6 0.9500 . ? C7 C8 1.3690(17) . ? C7 H7 0.9500 . ? C8 C9 1.4159(16) . ? C8 H8 0.9500 . ? C9 N1 1.3700(15) . ? C10 N2 1.3615(15) . ? C10 C11 1.3780(16) . ? C10 H10 0.9500 . ? C11 C12 1.4445(15) . ? C12 C13 1.4015(16) . ? C12 C17 1.4118(16) . ? C13 C14 1.3827(16) . ? C13 H13 0.9500 . ? C14 C15 1.4008(17) . ? C14 H14 0.9500 . ? C15 C16 1.3807(17) . ? C15 H15 0.9500 . ? C16 C17 1.3973(16) . ? C16 H16 0.9500 . ? C17 N2 1.3807(15) . ? C18 N2 1.4522(15) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 121.88(11) . . ? N1 C1 C11 118.03(10) . . ? C2 C1 C11 120.09(10) . . ? C3 C2 C1 119.90(11) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 119.77(10) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 123.40(11) . . ? C5 C4 C9 119.49(11) . . ? C3 C4 C9 117.09(10) . . ? C6 C5 C4 120.67(11) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 119.97(11) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 120.64(11) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 120.62(11) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? N1 C9 C8 118.59(10) . . ? N1 C9 C4 122.83(10) . . ? C8 C9 C4 118.58(11) . . ? N2 C10 C11 110.78(10) . . ? N2 C10 H10 124.6 . . ? C11 C10 H10 124.6 . . ? C10 C11 C12 105.84(10) . . ? C10 C11 C1 126.21(10) . . ? C12 C11 C1 127.91(10) . . ? C13 C12 C17 118.62(10) . . ? C13 C12 C11 134.60(11) . . ? C17 C12 C11 106.76(10) . . ? C14 C13 C12 118.67(11) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C13 C14 C15 121.64(11) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C16 C15 C14 121.22(11) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C17 116.99(11) . . ? C15 C16 H16 121.5 . . ? C17 C16 H16 121.5 . . ? N2 C17 C16 129.22(11) . . ? N2 C17 C12 107.93(10) . . ? C16 C17 C12 122.85(11) . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C1 N1 C9 118.46(10) . . ? C10 N2 C17 108.68(9) . . ? C10 N2 C18 125.89(10) . . ? C17 N2 C18 125.36(10) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.197 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.034 # Attachment '- XrayComp6e.cif' data_bergman05 _database_code_depnum_ccdc_archive 'CCDC 809742' #TrackingRef '- XrayComp6e.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bergman05 ; _chemical_name_common MB-II-194 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 Cl2 N2' _chemical_formula_weight 379.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.5493(10) _cell_length_b 9.3890(11) _cell_length_c 22.288(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.850(7) _cell_angle_gamma 90.00 _cell_volume 1772.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9424 _cell_measurement_theta_min 5.12 _cell_measurement_theta_max 67.62 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 3.344 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6897 _exptl_absorpt_correction_T_max 0.8779 _exptl_absorpt_process_details SADABS _diffrn_refln_scan_width 1.0 _diffrn_refln_scan_rate 5 _space_group.centring_type primitive _space_group.IT_number 14 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'microfocus rotating anode' _diffrn_radiation_monochromator 'HELIOS multilayer mirrors' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_reflns_number 22240 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 4.00 _diffrn_reflns_theta_max 68.04 _reflns_number_total 3206 _reflns_number_gt 2795 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR-2008 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics ORTEP-32 _computing_publication_material WinGX _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^)+(0.0670P)^2^+0.4411P] 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 3206 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.1084 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 C1 C 0.1585(2) 0.3162(2) 0.73921(8) 0.0239(4) Uani 1 1 d . . . H1 H 0.0617 0.3595 0.7456 0.029 Uiso 1 1 calc R . . C2 C 0.1762(2) 0.22143(19) 0.69339(8) 0.0216(4) Uani 1 1 d . . . C3 C 0.3419(2) 0.1838(2) 0.70033(8) 0.0221(4) Uani 1 1 d . . . C4 C 0.4355(2) 0.0982(2) 0.66811(8) 0.0248(4) Uani 1 1 d . . . H4 H 0.3893 0.0464 0.6336 0.030 Uiso 1 1 calc R . . C5 C 0.5960(2) 0.0902(2) 0.68716(8) 0.0280(4) Uani 1 1 d . . . H5 H 0.6598 0.0318 0.6656 0.034 Uiso 1 1 calc R . . C6 C 0.6667(2) 0.1673(2) 0.73805(8) 0.0300(4) Uani 1 1 d . . . H6 H 0.7773 0.1597 0.7502 0.036 Uiso 1 1 calc R . . C7 C 0.5777(2) 0.2536(2) 0.77046(8) 0.0281(4) Uani 1 1 d . . . H7 H 0.6252 0.3063 0.8046 0.034 Uiso 1 1 calc R . . C8 C 0.4151(2) 0.2608(2) 0.75124(8) 0.0242(4) Uani 1 1 d . . . C9 C 0.0550(2) 0.1646(2) 0.64593(7) 0.0218(4) Uani 1 1 d . . . C10 C -0.0755(2) 0.2513(2) 0.61742(8) 0.0219(4) Uani 1 1 d . . . C11 C -0.0937(2) 0.3958(2) 0.63193(8) 0.0246(4) Uani 1 1 d . . . H11 H -0.0173 0.4402 0.6609 0.029 Uiso 1 1 calc R . . C12 C -0.2202(2) 0.4738(2) 0.60486(9) 0.0290(4) Uani 1 1 d . . . H12 H -0.2311 0.5711 0.6152 0.035 Uiso 1 1 calc R . . C13 C -0.3324(2) 0.4089(2) 0.56219(8) 0.0320(5) Uani 1 1 d . . . H13 H -0.4210 0.4622 0.5441 0.038 Uiso 1 1 calc R . . C14 C -0.3163(2) 0.2694(2) 0.54603(8) 0.0288(4) Uani 1 1 d . . . H14 H -0.3930 0.2278 0.5163 0.035 Uiso 1 1 calc R . . C15 C -0.1876(2) 0.1868(2) 0.57289(7) 0.0237(4) Uani 1 1 d . . . C16 C -0.1637(2) 0.0408(2) 0.55609(7) 0.0236(4) Uani 1 1 d . . . C17 C -0.2644(2) -0.0348(2) 0.51127(8) 0.0283(4) Uani 1 1 d . . . H17 H -0.3564 0.0107 0.4914 0.034 Uiso 1 1 calc R . . C18 C -0.2323(2) -0.1713(2) 0.49601(8) 0.0307(4) Uani 1 1 d . . . H18 H -0.3017 -0.2193 0.4657 0.037 Uiso 1 1 calc R . . C19 C -0.0971(2) -0.2415(2) 0.52480(8) 0.0288(4) Uani 1 1 d . . . H19 H -0.0748 -0.3364 0.5139 0.035 Uiso 1 1 calc R . . C20 C 0.0026(2) -0.1716(2) 0.56894(8) 0.0275(4) Uani 1 1 d . . . H20 H 0.0936 -0.2189 0.5887 0.033 Uiso 1 1 calc R . . C21 C -0.0292(2) -0.0307(2) 0.58500(8) 0.0232(4) Uani 1 1 d . . . C22 C 0.5964(3) 0.4343(2) 0.34934(9) 0.0353(5) Uani 1 1 d . . . H22A H 0.6477 0.4169 0.3128 0.042 Uiso 1 1 calc R . . H22B H 0.5122 0.5061 0.3390 0.042 Uiso 1 1 calc R . . N1 N 0.30034(19) 0.33881(18) 0.77416(7) 0.0251(3) Uani 1 1 d . . . H1A H 0.3160 0.3944 0.8062 0.030 Uiso 1 1 calc R . . N2 N 0.07575(18) 0.03242(17) 0.63021(6) 0.0225(3) Uani 1 1 d . . . Cl1 Cl 0.73698(6) 0.50031(6) 0.40795(2) 0.03707(16) Uani 1 1 d . . . Cl2 Cl 0.51181(6) 0.27301(5) 0.37188(2) 0.03286(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0256(9) 0.0251(9) 0.0201(8) 0.0021(7) -0.0002(7) 0.0003(7) C2 0.0238(9) 0.0212(9) 0.0192(8) 0.0024(7) 0.0000(7) 0.0000(7) C3 0.0255(9) 0.0214(9) 0.0181(8) 0.0039(7) -0.0016(7) -0.0023(7) C4 0.0283(9) 0.0255(9) 0.0199(8) 0.0026(7) 0.0007(7) -0.0001(7) C5 0.0274(9) 0.0317(10) 0.0254(9) 0.0037(7) 0.0053(7) 0.0018(8) C6 0.0222(9) 0.0375(11) 0.0290(9) 0.0068(8) -0.0007(7) -0.0035(8) C7 0.0277(10) 0.0315(10) 0.0230(9) 0.0020(7) -0.0036(7) -0.0055(8) C8 0.0286(9) 0.0226(9) 0.0206(8) 0.0023(7) 0.0006(7) -0.0035(7) C9 0.0224(8) 0.0259(9) 0.0169(8) 0.0017(7) 0.0017(6) -0.0009(7) C10 0.0212(8) 0.0264(9) 0.0182(8) 0.0035(7) 0.0032(6) -0.0012(7) C11 0.0242(9) 0.0281(10) 0.0212(8) 0.0019(7) 0.0028(7) 0.0010(7) C12 0.0299(10) 0.0292(10) 0.0281(9) 0.0035(8) 0.0045(7) 0.0059(8) C13 0.0269(9) 0.0425(12) 0.0255(9) 0.0051(8) -0.0001(7) 0.0113(9) C14 0.0248(9) 0.0392(11) 0.0212(9) 0.0013(8) -0.0015(7) 0.0018(8) C15 0.0232(9) 0.0314(10) 0.0169(8) 0.0037(7) 0.0036(7) -0.0004(7) C16 0.0222(9) 0.0302(10) 0.0181(8) 0.0016(7) 0.0019(7) -0.0042(7) C17 0.0250(9) 0.0357(11) 0.0227(9) 0.0007(8) -0.0023(7) -0.0043(8) C18 0.0302(10) 0.0368(11) 0.0239(9) -0.0034(8) -0.0007(7) -0.0115(8) C19 0.0371(11) 0.0251(10) 0.0242(9) -0.0007(7) 0.0037(8) -0.0064(8) C20 0.0311(10) 0.0275(10) 0.0228(9) 0.0015(7) -0.0003(7) -0.0007(8) C21 0.0258(9) 0.0263(9) 0.0169(8) 0.0018(7) 0.0010(7) -0.0037(7) C22 0.0471(12) 0.0313(11) 0.0279(10) 0.0008(8) 0.0067(9) 0.0013(9) N1 0.0288(8) 0.0252(8) 0.0201(7) -0.0035(6) -0.0006(6) -0.0027(6) N2 0.0247(8) 0.0235(8) 0.0181(7) 0.0008(6) -0.0013(6) -0.0004(6) Cl1 0.0344(3) 0.0346(3) 0.0423(3) -0.0005(2) 0.0054(2) -0.0038(2) Cl2 0.0356(3) 0.0271(3) 0.0353(3) -0.00262(18) 0.00257(19) 0.00182(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.365(2) . ? C1 C2 1.378(3) . ? C1 H1 0.9500 . ? C2 C3 1.448(3) . ? C2 C9 1.476(2) . ? C3 C4 1.399(3) . ? C3 C8 1.417(3) . ? C4 C5 1.382(3) . ? C4 H4 0.9500 . ? C5 C6 1.410(3) . ? C5 H5 0.9500 . ? C6 C7 1.381(3) . ? C6 H6 0.9500 . ? C7 C8 1.400(3) . ? C7 H7 0.9500 . ? C8 N1 1.377(3) . ? C9 N2 1.308(3) . ? C9 C10 1.455(2) . ? C10 C11 1.408(3) . ? C10 C15 1.418(3) . ? C11 C12 1.375(3) . ? C11 H11 0.9500 . ? C12 C13 1.395(3) . ? C12 H12 0.9500 . ? C13 C14 1.370(3) . ? C13 H13 0.9500 . ? C14 C15 1.411(3) . ? C14 H14 0.9500 . ? C15 C16 1.443(3) . ? C16 C21 1.409(3) . ? C16 C17 1.417(3) . ? C17 C18 1.363(3) . ? C17 H17 0.9500 . ? C18 C19 1.407(3) . ? C18 H18 0.9500 . ? C19 C20 1.377(3) . ? C19 H19 0.9500 . ? C20 C21 1.407(3) . ? C20 H20 0.9500 . ? C21 N2 1.387(2) . ? C22 Cl1 1.762(2) . ? C22 Cl2 1.780(2) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? N1 H1A 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 110.15(17) . . ? N1 C1 H1 124.9 . . ? C2 C1 H1 124.9 . . ? C1 C2 C3 106.44(15) . . ? C1 C2 C9 128.86(17) . . ? C3 C2 C9 124.70(16) . . ? C4 C3 C8 118.90(17) . . ? C4 C3 C2 134.83(16) . . ? C8 C3 C2 106.22(16) . . ? C5 C4 C3 119.13(17) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 121.20(19) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C7 C6 C5 121.02(18) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 117.60(17) . . ? C6 C7 H7 121.2 . . ? C8 C7 H7 121.2 . . ? N1 C8 C7 129.81(17) . . ? N1 C8 C3 108.05(16) . . ? C7 C8 C3 122.13(18) . . ? N2 C9 C10 122.52(16) . . ? N2 C9 C2 115.31(16) . . ? C10 C9 C2 122.14(17) . . ? C11 C10 C15 119.13(17) . . ? C11 C10 C9 122.74(16) . . ? C15 C10 C9 118.13(17) . . ? C12 C11 C10 121.13(18) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 119.5(2) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 120.80(18) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 120.95(18) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C14 C15 C10 118.40(18) . . ? C14 C15 C16 122.83(17) . . ? C10 C15 C16 118.76(16) . . ? C21 C16 C17 117.59(18) . . ? C21 C16 C15 117.99(16) . . ? C17 C16 C15 124.39(17) . . ? C18 C17 C16 121.54(18) . . ? C18 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? C17 C18 C19 120.50(17) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C20 C19 C18 119.48(19) . . ? C20 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? C19 C20 C21 120.52(18) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? N2 C21 C20 117.26(17) . . ? N2 C21 C16 122.38(18) . . ? C20 C21 C16 120.36(17) . . ? Cl1 C22 Cl2 110.63(11) . . ? Cl1 C22 H22A 109.5 . . ? Cl2 C22 H22A 109.5 . . ? Cl1 C22 H22B 109.5 . . ? Cl2 C22 H22B 109.5 . . ? H22A C22 H22B 108.1 . . ? C1 N1 C8 109.13(15) . . ? C1 N1 H1A 125.4 . . ? C8 N1 H1A 125.4 . . ? C9 N2 C21 120.11(16) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.310 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.071