# 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 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Cariati, Elena' 'Galli, Simona' 'Macchi, Piero' 'Roberto, Dominique' 'Sironi, A.' 'Srdanov, Vojislav I.' 'Ugo, Renato' _publ_contact_author_name 'Professor A. Sironi' _publ_contact_author_address ; Professor A. Sironi Dipartimento di Chimica Strutturale e Stereochimica Inorganica Universita de Milano Via Venezian Milano 21-20133 ITALY ; _publ_contact_author_email 'ANGELO@CSMTBO.MI.CNR.IT' data_p21_c _database_code_CSD 163020 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 N' _chemical_formula_weight 181.23 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 5.817(4) _cell_length_b 7.528(5) _cell_length_c 11.274(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.260(10) _cell_angle_gamma 90.00 _cell_volume 492.9(6) _cell_formula_units_Z 2 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 192 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10979 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 34.97 _reflns_number_total 2074 _reflns_number_gt 1523 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0901P)^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 2074 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1306 _refine_ls_wR_factor_gt 0.1275 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _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 0.33450(14) -0.04094(10) -0.37092(7) 0.03612(19) Uani 0.50 1 d P . . N1 N 0.33450(14) -0.04094(10) -0.37092(7) 0.03612(19) Uani 0.50 1 d P . . C2 C 0.13239(16) 0.04170(11) -0.34753(7) 0.03441(19) Uani 1 1 d . . . C3 C 0.04994(13) 0.04706(10) -0.23471(6) 0.02850(17) Uani 1 1 d . . . C4 C 0.17428(11) -0.03439(8) -0.13941(6) 0.02424(15) Uani 1 1 d . . . C5 C 0.38090(12) -0.11835(10) -0.16354(7) 0.02967(17) Uani 1 1 d . . . C6 C 0.45612(14) -0.11975(11) -0.27842(8) 0.03446(19) Uani 1 1 d . . . C7 C 0.09687(12) -0.03658(9) -0.01784(6) 0.02570(16) Uani 1 1 d . . . H1 H 0.392(4) -0.040(3) -0.448(3) 0.054(7) Uiso 0.50 1 d P . . H2 H 0.041(2) 0.1009(16) -0.4122(11) 0.046(3) Uiso 1 1 d . . . H3 H -0.0919(19) 0.1111(15) -0.2222(9) 0.040(3) Uiso 1 1 d . . . H5 H 0.4707(19) -0.1798(16) -0.0980(9) 0.040(3) Uiso 1 1 d . . . H6 H 0.600(2) -0.1832(19) -0.2953(10) 0.049(3) Uiso 1 1 d . . . H7 H 0.1984(19) -0.1004(16) 0.0397(10) 0.040(3) Uiso 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 0.0454(4) 0.0320(3) 0.0321(3) -0.0041(3) 0.0122(3) -0.0036(3) N1 0.0454(4) 0.0320(3) 0.0321(3) -0.0041(3) 0.0122(3) -0.0036(3) C2 0.0457(4) 0.0315(4) 0.0261(3) 0.0005(3) 0.0028(3) 0.0013(3) C3 0.0307(3) 0.0280(3) 0.0267(3) 0.0001(2) 0.0014(2) 0.0033(3) C4 0.0249(3) 0.0217(3) 0.0261(3) -0.0013(2) 0.0010(2) -0.0014(2) C5 0.0269(3) 0.0290(3) 0.0331(4) -0.0021(3) 0.0016(3) 0.0014(3) C6 0.0313(4) 0.0321(4) 0.0410(4) -0.0059(3) 0.0108(3) -0.0014(3) C7 0.0269(3) 0.0253(3) 0.0248(3) 0.0009(2) -0.0003(2) 0.0016(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.3624(14) . ? C1 C2 1.3689(14) . ? C2 C3 1.3852(13) . ? C3 C4 1.4018(12) . ? C4 C5 1.3983(12) . ? C4 C7 1.4669(13) . ? C5 C6 1.3905(14) . ? C7 C7 1.3367(15) 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 C6 C1 C2 117.70(8) . . ? C1 C2 C3 122.42(7) . . ? C2 C3 C4 120.04(8) . . ? C5 C4 C3 117.41(7) . . ? C5 C4 C7 119.31(6) . . ? C3 C4 C7 123.28(7) . . ? C6 C5 C4 120.27(7) . . ? C1 C6 C5 122.17(8) . . ? C7 C7 C4 125.83(8) 3 . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 34.97 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.475 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.055 data_pc _database_code_CSD 163021 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 N' _chemical_formula_weight 181.23 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 5.817(4) _cell_length_b 7.528(5) _cell_length_c 11.274(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.260(10) _cell_angle_gamma 90.00 _cell_volume 492.9(6) _cell_formula_units_Z 2 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 192 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10999 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 34.97 _reflns_number_total 4022 _reflns_number_gt 2807 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0901P)^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 2(3) _refine_ls_number_reflns 4022 _refine_ls_number_parameters 85 _refine_ls_number_restraints 42 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1296 _refine_ls_wR_factor_gt 0.1252 _refine_ls_goodness_of_fit_ref 0.869 _refine_ls_restrained_S_all 0.865 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 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 0.3344(4) -0.2891(3) -0.3717(3) 0.03614(14) Uani 1 1 d D . . H1 H 0.3877 -0.2914 -0.4498 0.043 Uiso 1 1 calc RD . . C2 C 0.1308(5) -0.2060(3) -0.34770(17) 0.03440(14) Uani 1 1 d D . . H2 H 0.0436 -0.1493 -0.4107 0.041 Uiso 1 1 calc RD . . C3 C 0.0496(4) -0.2028(3) -0.23439(13) 0.02865(13) Uani 1 1 d D . . H3 H -0.0915 -0.1445 -0.2211 0.034 Uiso 1 1 calc RD . . C4 C 0.1738(3) -0.2848(2) -0.13944(13) 0.02436(12) Uani 1 1 d D . . C5 C 0.3823(3) -0.3664(3) -0.16345(17) 0.02962(13) Uani 1 1 d D . . H5 H 0.4729 -0.4207 -0.1008 0.036 Uiso 1 1 calc RD . . C6 C 0.4576(5) -0.3687(3) -0.27803(16) 0.03443(15) Uani 1 1 d D . . H6 H 0.5983 -0.4268 -0.2924 0.041 Uiso 1 1 calc RD . . C7 C 0.0972(5) -0.2860(3) -0.01781(16) 0.02573(12) Uani 1 1 d D . . H7 H 0.1939 -0.3440 0.0409 0.031 Uiso 1 1 calc RD . . N1 N -0.3341(3) -0.2077(2) 0.3701(3) 0.03614(14) Uani 1 1 d D . . C2A C -0.1345(5) -0.2892(3) 0.34742(17) 0.03440(14) Uani 1 1 d D . . H2A H -0.0480 -0.3438 0.4114 0.041 Uiso 1 1 calc RD . . C3A C -0.0502(4) -0.2967(3) 0.23488(12) 0.02865(13) Uani 1 1 d D . . H3A H 0.0905 -0.3561 0.2227 0.034 Uiso 1 1 calc RD . . C4A C -0.1743(3) -0.2159(2) 0.13938(14) 0.02436(12) Uani 1 1 d D . . C5A C -0.3796(3) -0.1300(2) 0.16380(17) 0.02962(13) Uani 1 1 d D . . H5A H -0.4680 -0.0720 0.1018 0.036 Uiso 1 1 calc RD . . C6A C -0.4543(5) -0.1293(3) 0.27856(16) 0.03443(15) Uani 1 1 d D . . H6A H -0.5951 -0.0715 0.2932 0.041 Uiso 1 1 calc RD . . C7A C -0.0964(5) -0.2128(3) 0.01801(16) 0.02573(12) Uani 1 1 d D . . H7A H -0.1921 -0.1534 -0.0405 0.031 Uiso 1 1 calc RD . . 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 0.0457(3) 0.0318(3) 0.0321(3) -0.0043(2) 0.0125(2) -0.0042(2) C2 0.0460(3) 0.0310(3) 0.0262(3) 0.0006(2) 0.0026(2) 0.0013(3) C3 0.0307(3) 0.0281(3) 0.0271(2) 0.0001(2) 0.00152(19) 0.0033(2) C4 0.0251(2) 0.0216(2) 0.0263(2) -0.00145(18) 0.00113(17) -0.00168(18) C5 0.0269(3) 0.0287(3) 0.0332(3) -0.0018(2) 0.0012(2) 0.0011(2) C6 0.0309(3) 0.0319(3) 0.0415(3) -0.0061(2) 0.0109(2) -0.0016(2) C7 0.0271(2) 0.0252(2) 0.0247(2) 0.00099(18) -0.00061(18) 0.00147(19) N1 0.0457(3) 0.0318(3) 0.0321(3) -0.0043(2) 0.0125(2) -0.0042(2) C2A 0.0460(3) 0.0310(3) 0.0262(3) 0.0006(2) 0.0026(2) 0.0013(3) C3A 0.0307(3) 0.0281(3) 0.0271(2) 0.0001(2) 0.00152(19) 0.0033(2) C4A 0.0251(2) 0.0216(2) 0.0263(2) -0.00145(18) 0.00113(17) -0.00168(18) C5A 0.0269(3) 0.0287(3) 0.0332(3) -0.0018(2) 0.0012(2) 0.0011(2) C6A 0.0309(3) 0.0319(3) 0.0415(3) -0.0061(2) 0.0109(2) -0.0016(2) C7A 0.0271(2) 0.0252(2) 0.0247(2) 0.00099(18) -0.00061(18) 0.00147(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.379(3) . ? C1 C2 1.379(3) . ? C2 C3 1.3872(12) . ? C3 C4 1.4001(10) . ? C4 C5 1.3995(11) . ? C4 C7 1.4657(13) . ? C5 C6 1.3877(12) . ? C7 C7A 1.3366(13) . ? N1 C6A 1.349(2) . ? N1 C2A 1.350(2) . ? C2A C3A 1.3872(12) . ? C3A C4A 1.4004(10) . ? C4A C5A 1.3993(11) . ? C4A C7A 1.4659(13) . ? C5A C6A 1.3879(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 117.5(3) . . ? C1 C2 C3 122.0(2) . . ? C2 C3 C4 120.6(2) . . ? C5 C4 C3 117.4(2) . . ? C5 C4 C7 119.41(19) . . ? C3 C4 C7 123.2(2) . . ? C6 C5 C4 120.6(2) . . ? C1 C6 C5 122.0(3) . . ? C7A C7 C4 125.89(15) . . ? C6A N1 C2A 117.9(3) . . ? N1 C2A C3A 122.9(2) . . ? C2A C3A C4A 119.5(2) . . ? C5A C4A C3A 117.2(2) . . ? C5A C4A C7A 119.26(19) . . ? C3A C4A C7A 123.5(2) . . ? C6A C5A C4A 120.1(2) . . ? N1 C6A C5A 122.3(3) . . ? C7 C7A C4A 125.87(15) . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 34.97 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.470 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.054