Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Zhang-Jie Shi' _publ_contact_author_email ZSHI@PKU.EDU.CN _publ_section_title ; Controllable Oxidative Dimerization of Indole Derivatives toward 2,3'-Linked or 3,3'-Linked Biindoles via Pd-Catalyzed Direct C-H Tranformations ; loop_ _publ_author_name 'Zhang-Jie Shi.' 'Chun Feng.' 'Bi-Jie Li.' 'Yang Li.' 'Wen-Hua Wang.' ; Shang-Dong Yang ; # Attachment '3a.cif' data_3a _database_code_depnum_ccdc_archive 'CCDC 715135' #TrackingRef '3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic 'CCDC 715135' _chemical_name_common 'CCDC 715135' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 N2' _chemical_formula_weight 260.33 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 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 11.290(2) _cell_length_b 7.2745(15) _cell_length_c 17.151(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.63(3) _cell_angle_gamma 90.00 _cell_volume 1399.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6303 _exptl_absorpt_correction_T_max 0.8322 _exptl_absorpt_process_details sadabs _exptl_special_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3208 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3208 _reflns_number_gt 1841 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0822P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.133(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3208 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0914 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1395 _refine_ls_wR_factor_gt 0.1193 _refine_ls_goodness_of_fit_ref 0.903 _refine_ls_restrained_S_all 0.903 _refine_ls_shift/su_max 0.017 _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 C2 C 0.55423(13) 0.2572(2) 0.21975(8) 0.0477(4) Uani 1 1 d . . . C3 C 0.67476(13) 0.2022(2) 0.21031(9) 0.0484(4) Uani 1 1 d . . . C10 C 0.45700(13) 0.2738(2) 0.15698(9) 0.0476(4) Uani 1 1 d . . . C12 C 0.34559(14) 0.3148(2) 0.04009(9) 0.0539(4) Uani 1 1 d . . . N2 N 0.33733(11) 0.25479(17) 0.16835(7) 0.0502(4) Uani 1 1 d . . . C11 C 0.46271(14) 0.3096(2) 0.07885(9) 0.0547(4) Uani 1 1 d . . . H11 H 0.5321 0.3274 0.0554 0.066 Uiso 1 1 calc R . . C17 C 0.26850(14) 0.2810(2) 0.09790(9) 0.0524(4) Uani 1 1 d . . . C1 C 0.55532(14) 0.2989(2) 0.29811(9) 0.0537(4) Uani 1 1 d . . . H1 H 0.4892 0.3386 0.3211 0.064 Uiso 1 1 calc R . . N1 N 0.66569(12) 0.27451(18) 0.33744(7) 0.0565(4) Uani 1 1 d . . . C8 C 0.74139(14) 0.2152(2) 0.28484(10) 0.0534(4) Uani 1 1 d . . . C4 C 0.73335(14) 0.1414(2) 0.14719(10) 0.0592(4) Uani 1 1 d . . . H4 H 0.6918 0.1298 0.0974 0.071 Uiso 1 1 calc R . . C18 C 0.28946(14) 0.1994(2) 0.24012(9) 0.0593(5) Uani 1 1 d . . . H18A H 0.2742 0.3066 0.2700 0.089 Uiso 1 1 calc R . . H18B H 0.3462 0.1222 0.2706 0.089 Uiso 1 1 calc R . . H18C H 0.2165 0.1328 0.2270 0.089 Uiso 1 1 calc R . . C16 C 0.14507(15) 0.2775(3) 0.07995(12) 0.0675(5) Uani 1 1 d . . . H16 H 0.0952 0.2551 0.1184 0.081 Uiso 1 1 calc R . . C13 C 0.29506(17) 0.3466(3) -0.03738(10) 0.0720(5) Uani 1 1 d . . . H13 H 0.3435 0.3698 -0.0766 0.086 Uiso 1 1 calc R . . C7 C 0.86149(16) 0.1716(3) 0.29754(11) 0.0684(5) Uani 1 1 d . . . H7 H 0.9039 0.1808 0.3472 0.082 Uiso 1 1 calc R . . C9 C 0.69806(18) 0.3040(3) 0.42114(9) 0.0727(5) Uani 1 1 d . . . H9A H 0.6329 0.3616 0.4430 0.109 Uiso 1 1 calc R . . H9B H 0.7670 0.3819 0.4290 0.109 Uiso 1 1 calc R . . H9C H 0.7156 0.1880 0.4466 0.109 Uiso 1 1 calc R . . C5 C 0.85248(15) 0.0992(3) 0.15971(11) 0.0728(5) Uani 1 1 d . . . H5 H 0.8916 0.0600 0.1178 0.087 Uiso 1 1 calc R . . C15 C 0.09992(18) 0.3085(3) 0.00352(13) 0.0836(6) Uani 1 1 d . . . H15 H 0.0178 0.3063 -0.0100 0.100 Uiso 1 1 calc R . . C6 C 0.91566(16) 0.1140(3) 0.23385(12) 0.0791(6) Uani 1 1 d . . . H6 H 0.9963 0.0844 0.2407 0.095 Uiso 1 1 calc R . . C14 C 0.1738(2) 0.3432(3) -0.05454(12) 0.0850(6) Uani 1 1 d . . . H14 H 0.1400 0.3643 -0.1058 0.102 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 C2 0.0521(9) 0.0457(8) 0.0471(8) 0.0009(6) 0.0132(7) -0.0027(7) C3 0.0504(8) 0.0460(8) 0.0502(9) 0.0036(7) 0.0114(7) -0.0063(7) C10 0.0473(8) 0.0476(8) 0.0499(9) -0.0019(7) 0.0138(7) -0.0015(6) C12 0.0604(10) 0.0509(9) 0.0510(9) -0.0050(7) 0.0086(7) -0.0007(7) N2 0.0480(7) 0.0531(8) 0.0518(8) 0.0010(6) 0.0158(6) 0.0019(6) C11 0.0533(9) 0.0649(10) 0.0481(9) 0.0003(7) 0.0150(7) -0.0038(7) C17 0.0548(9) 0.0462(8) 0.0567(9) -0.0063(7) 0.0088(7) 0.0024(7) C1 0.0600(10) 0.0509(9) 0.0521(9) 0.0013(7) 0.0150(8) 0.0005(7) N1 0.0677(9) 0.0562(8) 0.0460(8) 0.0017(6) 0.0075(7) -0.0040(7) C8 0.0555(9) 0.0489(9) 0.0562(9) 0.0070(7) 0.0089(7) -0.0062(7) C4 0.0568(10) 0.0658(11) 0.0578(10) 0.0022(8) 0.0191(7) -0.0036(8) C18 0.0581(10) 0.0626(10) 0.0618(10) 0.0046(8) 0.0264(8) 0.0013(8) C16 0.0526(10) 0.0726(12) 0.0778(12) -0.0102(9) 0.0094(9) 0.0018(8) C13 0.0819(13) 0.0798(13) 0.0535(10) -0.0075(9) 0.0048(9) -0.0015(10) C7 0.0585(10) 0.0728(12) 0.0721(12) 0.0130(9) -0.0002(9) -0.0078(9) C9 0.1009(14) 0.0668(12) 0.0491(10) 0.0003(8) 0.0032(9) -0.0081(10) C5 0.0576(10) 0.0831(13) 0.0823(13) 0.0046(11) 0.0280(9) 0.0005(9) C15 0.0620(11) 0.0975(16) 0.0875(15) -0.0168(12) -0.0082(11) 0.0056(11) C6 0.0482(10) 0.0918(15) 0.0988(15) 0.0167(12) 0.0143(10) -0.0017(9) C14 0.0829(14) 0.0998(16) 0.0674(12) -0.0122(11) -0.0128(11) 0.0055(12) _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 C2 C1 1.376(2) . ? C2 C3 1.445(2) . ? C2 C10 1.451(2) . ? C3 C4 1.404(2) . ? C3 C8 1.410(2) . ? C10 C11 1.374(2) . ? C10 N2 1.3941(18) . ? C12 C13 1.403(2) . ? C12 C11 1.410(2) . ? C12 C17 1.414(2) . ? N2 C17 1.372(2) . ? N2 C18 1.4571(18) . ? C11 H11 0.9300 . ? C17 C16 1.392(2) . ? C1 N1 1.359(2) . ? C1 H1 0.9300 . ? N1 C8 1.382(2) . ? N1 C9 1.456(2) . ? C8 C7 1.385(2) . ? C4 C5 1.372(2) . ? C4 H4 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C16 C15 1.369(3) . ? C16 H16 0.9300 . ? C13 C14 1.367(3) . ? C13 H13 0.9300 . ? C7 C6 1.377(3) . ? C7 H7 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C5 C6 1.388(2) . ? C5 H5 0.9300 . ? C15 C14 1.394(3) . ? C15 H15 0.9300 . ? C6 H6 0.9300 . ? C14 H14 0.9300 . ? 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 C2 C3 105.54(14) . . ? C1 C2 C10 128.83(14) . . ? C3 C2 C10 125.53(14) . . ? C4 C3 C8 118.08(14) . . ? C4 C3 C2 135.01(15) . . ? C8 C3 C2 106.90(13) . . ? C11 C10 N2 108.09(14) . . ? C11 C10 C2 128.51(14) . . ? N2 C10 C2 123.39(14) . . ? C13 C12 C11 135.01(16) . . ? C13 C12 C17 118.46(15) . . ? C11 C12 C17 106.52(14) . . ? C17 N2 C10 108.82(12) . . ? C17 N2 C18 123.68(13) . . ? C10 N2 C18 127.27(13) . . ? C10 C11 C12 108.53(14) . . ? C10 C11 H11 125.7 . . ? C12 C11 H11 125.7 . . ? N2 C17 C16 130.01(15) . . ? N2 C17 C12 108.04(13) . . ? C16 C17 C12 121.96(15) . . ? N1 C1 C2 111.13(14) . . ? N1 C1 H1 124.4 . . ? C2 C1 H1 124.4 . . ? C1 N1 C8 108.52(13) . . ? C1 N1 C9 125.59(15) . . ? C8 N1 C9 125.88(15) . . ? N1 C8 C7 129.57(16) . . ? N1 C8 C3 107.90(14) . . ? C7 C8 C3 122.52(16) . . ? C5 C4 C3 119.37(16) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? 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 . . ? C15 C16 C17 117.47(18) . . ? C15 C16 H16 121.3 . . ? C17 C16 H16 121.3 . . ? C14 C13 C12 119.24(18) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C6 C7 C8 117.46(17) . . ? C6 C7 H7 121.3 . . ? C8 C7 H7 121.3 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C5 C6 121.12(17) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C16 C15 C14 121.76(19) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C7 C6 C5 121.45(17) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C13 C14 C15 121.10(18) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 C4 178.98(17) . . . . ? C10 C2 C3 C4 -4.4(3) . . . . ? C1 C2 C3 C8 -0.14(16) . . . . ? C10 C2 C3 C8 176.51(13) . . . . ? C1 C2 C10 C11 149.26(17) . . . . ? C3 C2 C10 C11 -26.6(2) . . . . ? C1 C2 C10 N2 -30.5(2) . . . . ? C3 C2 C10 N2 153.60(14) . . . . ? C11 C10 N2 C17 -0.76(17) . . . . ? C2 C10 N2 C17 179.07(13) . . . . ? C11 C10 N2 C18 173.79(14) . . . . ? C2 C10 N2 C18 -6.4(2) . . . . ? N2 C10 C11 C12 0.40(17) . . . . ? C2 C10 C11 C12 -179.43(14) . . . . ? C13 C12 C11 C10 179.10(18) . . . . ? C17 C12 C11 C10 0.10(17) . . . . ? C10 N2 C17 C16 -179.29(16) . . . . ? C18 N2 C17 C16 5.9(3) . . . . ? C10 N2 C17 C12 0.82(16) . . . . ? C18 N2 C17 C12 -173.97(13) . . . . ? C13 C12 C17 N2 -179.76(14) . . . . ? C11 C12 C17 N2 -0.57(17) . . . . ? C13 C12 C17 C16 0.3(2) . . . . ? C11 C12 C17 C16 179.53(15) . . . . ? C3 C2 C1 N1 0.05(17) . . . . ? C10 C2 C1 N1 -176.45(13) . . . . ? C2 C1 N1 C8 0.06(17) . . . . ? C2 C1 N1 C9 -179.27(14) . . . . ? C1 N1 C8 C7 -179.67(16) . . . . ? C9 N1 C8 C7 -0.3(3) . . . . ? C1 N1 C8 C3 -0.15(16) . . . . ? C9 N1 C8 C3 179.18(13) . . . . ? C4 C3 C8 N1 -179.11(13) . . . . ? C2 C3 C8 N1 0.18(16) . . . . ? C4 C3 C8 C7 0.4(2) . . . . ? C2 C3 C8 C7 179.74(14) . . . . ? C8 C3 C4 C5 -0.8(2) . . . . ? C2 C3 C4 C5 -179.83(16) . . . . ? N2 C17 C16 C15 -179.91(16) . . . . ? C12 C17 C16 C15 0.0(3) . . . . ? C11 C12 C13 C14 -179.19(19) . . . . ? C17 C12 C13 C14 -0.3(3) . . . . ? N1 C8 C7 C6 179.55(17) . . . . ? C3 C8 C7 C6 0.1(2) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C17 C16 C15 C14 -0.3(3) . . . . ? C8 C7 C6 C5 -0.3(3) . . . . ? C4 C5 C6 C7 -0.1(3) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? C16 C15 C14 C13 0.4(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.315 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.121 # Attachment '4a.cif' data_4a _database_code_depnum_ccdc_archive 'CCDC 755576' #TrackingRef '4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 N2' _chemical_formula_sum 'C18 H16 N2' _chemical_formula_weight 260.33 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 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 6.4851(13) _cell_length_b 13.409(3) _cell_length_c 8.1723(16) _cell_angle_alpha 90.00 _cell_angle_beta 109.73(3) _cell_angle_gamma 90.00 _cell_volume 668.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 435 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9833 _exptl_absorpt_correction_T_max 0.9924 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4364 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1160 _reflns_number_gt 1101 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (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^)+(0.0453P)^2^+0.2941P] 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 1160 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1175 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _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 -0.2375(2) 0.98855(11) 0.25261(18) 0.0309(4) Uani 1 1 d . . . C1 C -0.0721(3) 0.84119(14) 0.4383(2) 0.0339(5) Uani 1 1 d . . . H1A H -0.1583 0.8460 0.5117 0.041 Uiso 1 1 calc R . . C2 C 0.0820(3) 0.76746(15) 0.4615(2) 0.0386(5) Uani 1 1 d . . . H2A H 0.1041 0.7208 0.5532 0.046 Uiso 1 1 calc R . . C3 C 0.2072(3) 0.75997(14) 0.3520(2) 0.0373(5) Uani 1 1 d . . . H3A H 0.3118 0.7079 0.3703 0.045 Uiso 1 1 calc R . . C4 C 0.1818(3) 0.82660(13) 0.2185(2) 0.0306(4) Uani 1 1 d . . . H4A H 0.2674 0.8200 0.1450 0.037 Uiso 1 1 calc R . . C5 C 0.0286(3) 0.90432(12) 0.1914(2) 0.0258(4) Uani 1 1 d . . . C6 C -0.0402(3) 0.98636(12) 0.0707(2) 0.0258(4) Uani 1 1 d . . . C7 C -0.2011(3) 1.03452(14) 0.1148(2) 0.0307(4) Uani 1 1 d . . . H7A H -0.2772 1.0921 0.0575 0.037 Uiso 1 1 calc R . . C8 C -0.0977(3) 0.90903(13) 0.3028(2) 0.0279(4) Uani 1 1 d . . . C9 C -0.3934(3) 1.02045(15) 0.3345(2) 0.0369(5) Uani 1 1 d . . . H9A H -0.4938 0.9655 0.3326 0.055 Uiso 1 1 calc R . . H9B H -0.4770 1.0776 0.2711 0.055 Uiso 1 1 calc R . . H9C H -0.3145 1.0398 0.4552 0.055 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 0.0321(8) 0.0386(9) 0.0271(8) 0.0021(6) 0.0167(6) 0.0009(6) C1 0.0360(10) 0.0399(11) 0.0267(9) 0.0021(7) 0.0118(7) -0.0102(8) C2 0.0432(11) 0.0381(10) 0.0326(10) 0.0097(8) 0.0101(8) -0.0071(9) C3 0.0404(11) 0.0316(10) 0.0380(10) 0.0061(8) 0.0108(8) 0.0015(8) C4 0.0326(10) 0.0308(9) 0.0294(9) 0.0004(7) 0.0119(7) -0.0010(7) C5 0.0274(9) 0.0286(9) 0.0218(8) -0.0023(6) 0.0088(7) -0.0057(7) C6 0.0277(9) 0.0284(9) 0.0230(8) -0.0007(7) 0.0106(7) -0.0019(7) C7 0.0338(10) 0.0348(9) 0.0268(9) 0.0039(7) 0.0145(7) 0.0028(7) C8 0.0286(9) 0.0320(9) 0.0231(8) -0.0023(7) 0.0087(7) -0.0073(7) C9 0.0364(10) 0.0464(12) 0.0351(10) -0.0030(8) 0.0215(8) -0.0013(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C8 1.370(2) . ? N1 C7 1.372(2) . ? N1 C9 1.453(2) . ? C1 C2 1.373(3) . ? C1 C8 1.399(2) . ? C1 H1A 0.9500 . ? C2 C3 1.400(3) . ? C2 H2A 0.9500 . ? C3 C4 1.377(2) . ? C3 H3A 0.9500 . ? C4 C5 1.405(2) . ? C4 H4A 0.9500 . ? C5 C8 1.417(2) . ? C5 C6 1.444(2) . ? C6 C7 1.375(2) . ? C6 C6 1.466(3) 3_575 ? C7 H7A 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 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 C8 N1 C7 108.42(14) . . ? C8 N1 C9 125.77(14) . . ? C7 N1 C9 125.80(16) . . ? C2 C1 C8 117.61(17) . . ? C2 C1 H1A 121.2 . . ? C8 C1 H1A 121.2 . . ? C1 C2 C3 121.07(17) . . ? C1 C2 H2A 119.5 . . ? C3 C2 H2A 119.5 . . ? C4 C3 C2 121.33(18) . . ? C4 C3 H3A 119.3 . . ? C2 C3 H3A 119.3 . . ? C3 C4 C5 119.69(16) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? C4 C5 C8 117.61(15) . . ? C4 C5 C6 135.38(15) . . ? C8 C5 C6 107.01(14) . . ? C7 C6 C5 105.40(14) . . ? C7 C6 C6 126.4(2) . 3_575 ? C5 C6 C6 128.22(19) . 3_575 ? N1 C7 C6 111.10(16) . . ? N1 C7 H7A 124.4 . . ? C6 C7 H7A 124.4 . . ? N1 C8 C1 129.26(16) . . ? N1 C8 C5 108.07(14) . . ? C1 C8 C5 122.67(16) . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 C1 C2 C3 -0.7(3) . . . . ? C1 C2 C3 C4 0.6(3) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C3 C4 C5 C8 -1.3(2) . . . . ? C3 C4 C5 C6 179.14(18) . . . . ? C4 C5 C6 C7 179.32(19) . . . . ? C8 C5 C6 C7 -0.23(18) . . . . ? C4 C5 C6 C6 -0.2(4) . . . 3_575 ? C8 C5 C6 C6 -179.7(2) . . . 3_575 ? C8 N1 C7 C6 0.6(2) . . . . ? C9 N1 C7 C6 178.99(16) . . . . ? C5 C6 C7 N1 -0.2(2) . . . . ? C6 C6 C7 N1 179.3(2) 3_575 . . . ? C7 N1 C8 C1 178.93(17) . . . . ? C9 N1 C8 C1 0.5(3) . . . . ? C7 N1 C8 C5 -0.70(19) . . . . ? C9 N1 C8 C5 -179.12(16) . . . . ? C2 C1 C8 N1 -179.85(17) . . . . ? C2 C1 C8 C5 -0.3(3) . . . . ? C4 C5 C8 N1 -179.07(14) . . . . ? C6 C5 C8 N1 0.57(18) . . . . ? C4 C5 C8 C1 1.3(2) . . . . ? C6 C5 C8 C1 -179.09(15) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.221 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.048