# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 data_a139 _audit_creation_method SHELXL-97 _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' _publ_contact_author_name 'Dr. Thomas Steiner' _publ_contact_author_address ; Institut fur Chemie - Kristallographie Freie Universitat Berlin Takustrasse 6 D-14195 Berlin Germany ; _publ_contact_author_email steiner@chemie.fu-berlin.de _publ_section_title ; A short C-H...N hydrogen bond with a very strong IR spectroscopic effect ; loop_ _publ_author_name _publ_author_address 'Boryczka, Stanislaw' ; Department of Organic Chemistry Silesian School of Medicine 4 Jagiellonska Str. 41-200 Sosnowiec Poland ; 'Rozenberg, Mark S.' ; Institute of Inorganic and Analytic Chemistry The Hebrew University of Jerusalem Jerusdalem, 91904 Israel ; 'Schreurs, Antoine M. M.' ; Bijvoet Center for Biomolecular Research Department of Crystal and Structural Chemistry Utrecht University Padualaan 8 3584 CH Utrecht The Netherlands ; 'Kroon, Jan' ; Bijvoet Center for Biomolecular Research Department of Crystal and Structural Chemistry Utrecht University Padualaan 8 3584 CH Utrecht The Netherlands ; 'Starikov, Evgeni B.' ; Institut fur Chemie - Kristallographie Freie Universitat Berlin Takustr. 6 D-14195 Berlin Germany ; 'Steiner, Thomas' ; Institut fur Chemie - Kristallographie Freie Universitat Berlin Takustr. 6 D-14195 Berlin Germany ; data_(I) _database_code_CSD 166477 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 N S Se' _chemical_formula_weight 292.25 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Se' 'Se' -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6112(3) _cell_length_b 8.8243(3) _cell_length_c 9.2589(3) _cell_angle_alpha 75.170(2) _cell_angle_beta 71.033(3) _cell_angle_gamma 63.780(2) _cell_volume 591.65(3) _cell_formula_units_Z 2 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'plate' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 3.319 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Nonius KappaCCD' _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 8849 _diffrn_reflns_av_R_equivalents 0.0826 _diffrn_reflns_av_sigmaI/netI 0.0505 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2704 _reflns_number_gt 2425 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0744P)^2^+0.2890P] 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 2704 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1089 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 Se1 Se 0.12795(4) 0.82797(3) 0.13401(3) 0.01666(13) Uani 1 1 d . . . S1 S 0.14014(10) 0.46468(9) 0.11853(9) 0.01803(18) Uani 1 1 d . . . N1 N 0.2640(3) 0.3612(3) 0.5272(3) 0.0182(5) Uani 1 1 d . . . C2 C 0.2270(4) 0.3505(4) 0.4048(4) 0.0184(6) Uani 1 1 d . . . H2 H 0.2276 0.2449 0.3969 0.037(12) Uiso 1 1 calc R . . C3 C 0.1859(4) 0.4858(4) 0.2825(3) 0.0146(6) Uani 1 1 d . . . C4 C 0.1847(4) 0.6400(3) 0.2944(3) 0.0136(5) Uani 1 1 d . . . C5 C 0.2235(4) 0.6569(4) 0.4270(3) 0.0151(6) Uani 1 1 d . . . C6 C 0.2253(4) 0.8096(4) 0.4503(4) 0.0193(6) Uani 1 1 d . . . H6 H 0.1961 0.9085 0.3767 0.032(11) Uiso 1 1 calc R . . C7 C 0.2688(4) 0.8144(4) 0.5784(4) 0.0243(7) Uani 1 1 d . . . H7 H 0.2717 0.9163 0.5916 0.030(11) Uiso 1 1 calc R . . C8 C 0.3094(4) 0.6702(4) 0.6912(4) 0.0239(7) Uani 1 1 d . . . H8 H 0.3385 0.6757 0.7797 0.045(13) Uiso 1 1 calc R . . C9 C 0.3068(4) 0.5220(4) 0.6724(4) 0.0199(6) Uani 1 1 d . . . H9 H 0.3336 0.4254 0.7487 0.009(8) Uiso 1 1 calc R . . C10 C 0.2645(4) 0.5120(4) 0.5404(3) 0.0164(6) Uani 1 1 d . . . C11 C 0.1463(4) 0.2504(4) 0.1590(4) 0.0222(7) Uani 1 1 d . . . H11A H 0.2673 0.1682 0.1642 0.029(10) Uiso 1 1 calc R . . H11B H 0.1126 0.2293 0.0769 0.033(11) Uiso 1 1 calc R . . H11C H 0.0624 0.2377 0.2578 0.043(13) Uiso 1 1 calc R . . C12 C 0.3768(4) 0.8092(4) 0.0388(4) 0.0201(6) Uani 1 1 d . . . H12A H 0.4241 0.8308 0.1123 0.040(12) Uiso 1 1 calc R . . H12B H 0.4540 0.6934 0.0102 0.034(11) Uiso 1 1 calc R . . C13 C 0.3743(4) 0.9364(4) -0.0986(4) 0.0182(6) Uani 1 1 d . . . C14 C 0.3654(4) 1.0419(4) -0.2078(4) 0.0215(6) Uani 1 1 d . . . H14 H 0.3583 1.1265 -0.2955 0.037(12) 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 Se1 0.01496(18) 0.01721(18) 0.01704(19) 0.00411(11) -0.00564(12) -0.00788(12) S1 0.0208(4) 0.0205(4) 0.0152(4) -0.0019(3) -0.0047(3) -0.0102(3) N1 0.0175(12) 0.0224(12) 0.0142(12) 0.0007(10) -0.0023(10) -0.0103(10) C2 0.0171(14) 0.0168(14) 0.0189(15) -0.0002(11) -0.0006(12) -0.0084(11) C3 0.0102(12) 0.0184(13) 0.0134(14) -0.0018(11) 0.0000(10) -0.0062(10) C4 0.0113(13) 0.0170(13) 0.0115(13) 0.0015(10) -0.0010(10) -0.0078(10) C5 0.0107(12) 0.0182(13) 0.0147(14) -0.0021(11) 0.0001(10) -0.0063(10) C6 0.0181(14) 0.0223(15) 0.0190(15) -0.0013(12) -0.0024(12) -0.0115(12) C7 0.0248(16) 0.0282(16) 0.0236(17) -0.0069(13) -0.0017(13) -0.0146(14) C8 0.0191(15) 0.0365(18) 0.0182(16) -0.0081(13) -0.0054(12) -0.0098(13) C9 0.0160(14) 0.0280(16) 0.0128(14) -0.0005(12) -0.0014(11) -0.0086(12) C10 0.0121(13) 0.0211(14) 0.0145(14) -0.0006(11) -0.0011(11) -0.0077(11) C11 0.0205(15) 0.0167(14) 0.0314(18) -0.0074(13) -0.0074(13) -0.0059(12) C12 0.0165(14) 0.0216(14) 0.0201(16) 0.0038(12) -0.0037(12) -0.0096(12) C13 0.0163(14) 0.0229(15) 0.0175(15) -0.0017(12) -0.0031(11) -0.0108(12) C14 0.0240(16) 0.0232(15) 0.0203(16) 0.0015(12) -0.0058(13) -0.0139(13) _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 Se1 C4 1.921(3) . ? Se1 C12 1.982(3) . ? S1 C3 1.758(3) . ? S1 C11 1.811(3) . ? N1 C2 1.308(4) . ? N1 C10 1.369(4) . ? C2 C3 1.424(4) . ? C2 H2 0.9500 . ? C3 C4 1.389(4) . ? C4 C5 1.430(4) . ? C5 C10 1.420(4) . ? C5 C6 1.426(4) . ? C6 C7 1.370(5) . ? C6 H6 0.9500 . ? C7 C8 1.413(5) . ? C7 H7 0.9500 . ? C8 C9 1.373(5) . ? C8 H8 0.9500 . ? C9 C10 1.417(4) . ? C9 H9 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.465(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.183(4) . ? C14 H14 0.9500 . ? 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 C4 Se1 C12 95.85(12) . . ? C3 S1 C11 103.24(15) . . ? C2 N1 C10 118.6(3) . . ? N1 C2 C3 124.6(3) . . ? N1 C2 H2 117.7 . . ? C3 C2 H2 117.7 . . ? C4 C3 C2 117.6(3) . . ? C4 C3 S1 119.3(2) . . ? C2 C3 S1 123.1(2) . . ? C3 C4 C5 119.4(3) . . ? C3 C4 Se1 119.5(2) . . ? C5 C4 Se1 121.1(2) . . ? C10 C5 C6 118.6(3) . . ? C10 C5 C4 117.7(3) . . ? C6 C5 C4 123.7(3) . . ? C7 C6 C5 120.3(3) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 121.0(3) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C9 C8 C7 119.9(3) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 120.6(3) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? N1 C10 C9 118.3(3) . . ? N1 C10 C5 122.1(3) . . ? C9 C10 C5 119.6(3) . . ? S1 C11 H11A 109.5 . . ? S1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? S1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 Se1 107.5(2) . . ? C13 C12 H12A 110.2 . . ? Se1 C12 H12A 110.2 . . ? C13 C12 H12B 110.2 . . ? Se1 C12 H12B 110.2 . . ? H12A C12 H12B 108.5 . . ? C14 C13 C12 177.5(3) . . ? C13 C14 H14 180.0 . . ? 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 C10 N1 C2 C3 -0.3(4) . . . . ? N1 C2 C3 C4 -0.1(4) . . . . ? N1 C2 C3 S1 179.0(2) . . . . ? C11 S1 C3 C4 -177.4(2) . . . . ? C11 S1 C3 C2 3.5(3) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? S1 C3 C4 C5 -179.4(2) . . . . ? C2 C3 C4 Se1 -179.4(2) . . . . ? S1 C3 C4 Se1 1.4(3) . . . . ? C12 Se1 C4 C3 -103.9(2) . . . . ? C12 Se1 C4 C5 76.9(2) . . . . ? C3 C4 C5 C10 0.9(4) . . . . ? Se1 C4 C5 C10 -179.9(2) . . . . ? C3 C4 C5 C6 -179.8(3) . . . . ? Se1 C4 C5 C6 -0.7(4) . . . . ? C10 C5 C6 C7 1.1(4) . . . . ? C4 C5 C6 C7 -178.1(3) . . . . ? C5 C6 C7 C8 -1.2(5) . . . . ? C6 C7 C8 C9 0.5(5) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C2 N1 C10 C9 -179.2(3) . . . . ? C2 N1 C10 C5 1.0(4) . . . . ? C8 C9 C10 N1 179.9(3) . . . . ? C8 C9 C10 C5 -0.3(4) . . . . ? C6 C5 C10 N1 179.4(3) . . . . ? C4 C5 C10 N1 -1.4(4) . . . . ? C6 C5 C10 C9 -0.4(4) . . . . ? C4 C5 C10 C9 178.9(3) . . . . ? C4 Se1 C12 C13 176.3(2) . . . . ? Se1 C12 C13 C14 12(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C14 H14 N1 0.95 2.30 3.225(4) 164.9 1_564 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.413 _refine_diff_density_min -1.221 _refine_diff_density_rms 0.137