# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Orde Quentin Munro' 'Craig D. Grimmer' 'Sandra D. Strydom' _publ_contact_author_name 'Dr Orde Quentin Munro' _publ_contact_author_address ; School of Chemical & Physical Sciences University of Natal Private Bag X01 Scottsville Pietermaritzburg KwaZulu-Natal 3209 SOUTH AFRICA ; _publ_contact_author_email MUNROO@NU.AC.ZA _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Complementary Hydrogen Bonding in a New Tridentate Schiff Base Ligand: X-Ray, DFT, and Solution NMR Studies ; data_phlig1c2 _database_code_CSD 219663 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-[(1E)-1H-pyrrol-2-ylmethylene]benzene-1,2-diamine ; _chemical_name_common 'Schiff base' _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 N3' _chemical_formula_sum 'C11 H11 N3' _chemical_formula_weight 185.23 _chemical_absolute_configuration unk 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 'C 2' _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 18.373(8) _cell_length_b 5.489(4) _cell_length_c 11.369(4) _cell_angle_alpha 90.00 _cell_angle_beta 124.22(3) _cell_angle_gamma 90.00 _cell_volume 948.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 122(2) _cell_measurement_reflns_used 476 _cell_measurement_theta_min 4 _cell_measurement_theta_max 32 _exptl_crystal_description paralleliped _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9454 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 122(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 'Oxford Diffraction Xcalibur2 CCD' _diffrn_measurement_method '\o-2\t scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4084 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.28 _diffrn_reflns_theta_max 31.56 _reflns_number_total 2065 _reflns_number_gt 1936 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis CCD 170' _computing_cell_refinement 'CrysAlis CCD 170' _computing_data_reduction 'CrysAlis RED 170' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WinGX (Farrugia, 1999)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0759P)^2^+0.0298P] 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 -1.2(18) _refine_ls_number_reflns 2065 _refine_ls_number_parameters 144 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.1016 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 0.40967(8) 1.0943(3) 0.70801(12) 0.0216(3) Uani 1 1 d . . . H1 H 0.4421(6) 1.0273(13) 0.8002(17) 0.026 Uiso 1 1 calc R . . C2 C 0.35664(8) 1.2987(3) 0.66564(13) 0.0225(3) Uani 1 1 d . . . H2 H 0.3459(2) 1.400(2) 0.7259(12) 0.027 Uiso 1 1 calc R . . C3 C 0.32070(8) 1.3353(3) 0.51947(13) 0.0216(3) Uani 1 1 d . . . H3 H 0.2819(8) 1.462(3) 0.4614(13) 0.026 Uiso 1 1 calc R . . C4 C 0.35290(7) 1.1512(2) 0.47705(12) 0.0173(2) Uani 1 1 d . . . C5 C 0.34016(7) 1.1088(3) 0.34175(12) 0.0181(2) Uani 1 1 d . . . H5 H 0.3026(7) 1.217(2) 0.2625(16) 0.022 Uiso 1 1 calc R . . C6 C 0.37299(7) 0.8937(2) 0.19765(12) 0.0171(2) Uani 1 1 d . . . C7 C 0.33255(8) 1.0499(2) 0.08001(12) 0.0206(3) Uani 1 1 d . . . H7 H 0.3007(6) 1.202(3) 0.08034(12) 0.025 Uiso 1 1 calc R . . C8 C 0.33536(9) 1.0004(3) -0.03747(13) 0.0225(3) Uani 1 1 d . . . H8 H 0.3072(6) 1.111(2) -0.1190(16) 0.027 Uiso 1 1 calc R . . C9 C 0.37863(9) 0.7922(3) -0.03796(13) 0.0224(3) Uani 1 1 d . . . H9 H 0.38063(10) 0.7576(7) -0.1196(16) 0.027 Uiso 1 1 calc R . . C10 C 0.41904(8) 0.6333(3) 0.07764(13) 0.0213(3) Uani 1 1 d . . . H10 H 0.4472(7) 0.493(3) 0.07554(13) 0.026 Uiso 1 1 calc R . . C11 C 0.41749(7) 0.6838(2) 0.19727(12) 0.0180(2) Uani 1 1 d . . . N1 N 0.40700(7) 1.0062(2) 0.59322(11) 0.0196(2) Uani 1 1 d . . . N2 N 0.37810(7) 0.9289(2) 0.32532(10) 0.0184(2) Uani 1 1 d . . . N3 N 0.46376(7) 0.5433(2) 0.31958(12) 0.0238(3) Uani 1 1 d . . . H1A H 0.4358(12) 0.877(5) 0.594(2) 0.029 Uiso 1 1 d . . . H3A H 0.4818(13) 0.399(4) 0.3139(19) 0.029 Uiso 1 1 d . . . H3B H 0.4447(12) 0.548(4) 0.375(2) 0.029 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 0.0219(5) 0.0266(6) 0.0171(5) -0.0004(5) 0.0115(4) -0.0010(5) C2 0.0227(5) 0.0261(7) 0.0223(5) -0.0062(5) 0.0148(5) -0.0029(5) C3 0.0189(5) 0.0228(6) 0.0223(5) -0.0013(5) 0.0111(4) 0.0020(4) C4 0.0148(5) 0.0196(6) 0.0165(5) 0.0005(4) 0.0083(4) 0.0012(4) C5 0.0154(4) 0.0220(6) 0.0146(4) -0.0001(4) 0.0070(4) 0.0001(4) C6 0.0163(5) 0.0185(6) 0.0154(4) -0.0016(4) 0.0084(4) -0.0025(4) C7 0.0221(5) 0.0207(6) 0.0168(5) -0.0002(4) 0.0096(4) -0.0008(5) C8 0.0260(6) 0.0241(6) 0.0156(5) -0.0012(4) 0.0104(4) -0.0050(5) C9 0.0251(6) 0.0263(7) 0.0188(5) -0.0051(5) 0.0141(5) -0.0071(5) C10 0.0213(5) 0.0221(6) 0.0229(5) -0.0045(5) 0.0138(4) -0.0027(5) C11 0.0156(5) 0.0197(6) 0.0181(5) -0.0016(4) 0.0090(4) -0.0022(4) N1 0.0197(4) 0.0223(5) 0.0165(4) 0.0017(4) 0.0100(4) 0.0040(4) N2 0.0189(4) 0.0206(5) 0.0160(4) 0.0002(4) 0.0100(4) 0.0004(4) N3 0.0267(5) 0.0234(6) 0.0220(5) 0.0037(4) 0.0142(4) 0.0074(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 1.3666(17) . ? C1 C2 1.383(2) . ? C1 H1 0.9418 . ? C2 C3 1.4157(19) . ? C2 H2 0.9842 . ? C3 C4 1.3876(19) . ? C3 H3 0.9472 . ? C4 N1 1.3745(18) . ? C4 C5 1.4388(16) . ? C5 N2 1.2815(18) . ? C5 H5 0.9703 . ? C6 C7 1.3993(19) . ? C6 N2 1.4142(15) . ? C6 C11 1.414(2) . ? C7 C8 1.3923(17) . ? C7 H7 1.0189 . ? C8 C9 1.394(2) . ? C8 H8 0.9770 . ? C9 C10 1.394(2) . ? C9 H9 0.9681 . ? C10 C11 1.4040(16) . ? C10 H10 0.9361 . ? C11 N3 1.3863(18) . ? N1 H1A 0.88(2) . ? N3 H3A 0.88(2) . ? N3 H3B 0.881(19) . ? 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 108.34(12) . . ? N1 C1 H1 125.8 . . ? C2 C1 H1 125.8 . . ? C1 C2 C3 107.23(12) . . ? C1 C2 H2 126.4 . . ? C3 C2 H2 126.4 . . ? C4 C3 C2 107.22(12) . . ? C4 C3 H3 126.4 . . ? C2 C3 H3 126.4 . . ? N1 C4 C3 107.88(11) . . ? N1 C4 C5 121.93(11) . . ? C3 C4 C5 130.12(12) . . ? N2 C5 C4 120.37(11) . . ? N2 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 N2 126.19(12) . . ? C7 C6 C11 119.57(11) . . ? N2 C6 C11 114.18(11) . . ? C8 C7 C6 120.74(13) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 119.53(13) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 120.80(12) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 119.99(13) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? N3 C11 C10 121.79(12) . . ? N3 C11 C6 118.67(12) . . ? C10 C11 C6 119.37(11) . . ? C1 N1 C4 109.33(12) . . ? C1 N1 H1A 125.5(12) . . ? C4 N1 H1A 125.2(12) . . ? C5 N2 C6 121.82(11) . . ? C11 N3 H3A 118.3(12) . . ? C11 N3 H3B 116.0(13) . . ? H3A N3 H3B 113.6(19) . . ? 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 N1 C1 C2 C3 -0.09(15) . . . . ? C1 C2 C3 C4 0.12(15) . . . . ? C2 C3 C4 N1 -0.10(14) . . . . ? C2 C3 C4 C5 -177.12(12) . . . . ? N1 C4 C5 N2 1.50(18) . . . . ? C3 C4 C5 N2 178.16(13) . . . . ? N2 C6 C7 C8 177.08(12) . . . . ? C11 C6 C7 C8 0.24(18) . . . . ? C6 C7 C8 C9 0.31(19) . . . . ? C7 C8 C9 C10 0.00(19) . . . . ? C8 C9 C10 C11 -0.85(19) . . . . ? C9 C10 C11 N3 -173.84(12) . . . . ? C9 C10 C11 C6 1.38(18) . . . . ? C7 C6 C11 N3 174.30(11) . . . . ? N2 C6 C11 N3 -2.91(16) . . . . ? C7 C6 C11 C10 -1.08(17) . . . . ? N2 C6 C11 C10 -178.28(10) . . . . ? C2 C1 N1 C4 0.03(14) . . . . ? C3 C4 N1 C1 0.05(14) . . . . ? C5 C4 N1 C1 177.36(11) . . . . ? C4 C5 N2 C6 -174.62(10) . . . . ? C7 C6 N2 C5 4.04(18) . . . . ? C11 C6 N2 C5 -178.97(11) . . . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.278 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.043