# Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Green Chemistry' _journal_coden_Cambridge 1048 _publ_contact_author_name 'Tania R. van den Ancker' _publ_contact_author_address ; Department of Biological and Physical Sciences Faculty of Science University of Southern Queensland Toowoomba Queensland 4350 Australia ; _publ_contact_author_phone '+61 7 4631 2363' _publ_contact_author_fax '+61 7 4631 1530' _publ_contact_author_email ancker@usq.edu.au _publ_section_title ; Benign approaches for the synthesis of bis-imine Schiff bases ; loop_ _publ_author_name _publ_author_address 'Colin L. Raston' ; School of Biomedical and Chemical Sciences University of Western Australia Crawley WA 6009 Australia ; 'Gareth W. V. Cave' ; School of Biomedical and Natural Sciences Nottingham Trent University Nottingham NS11 8NS UK ; 'van den Ancker,T.R.' ; Department of Biological and Physical Sciences Faculty of Science University of Southern Queensland Toowoomba Queensland 4350 Australia ; #======================================================= data_bisfuran _database_code_depnum_ccdc_archive 'CCDC 280847' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common N,N'-Bis(furan-2-ylmethylene)cyclohexane-1,2-diamine _chemical_melting_point ? _chemical_formula_moiety OC4H3CHNC6H10NCHC4H3O _chemical_formula_sum 'C16 H18 N2 O2' _chemical_formula_weight 270.32 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 9.4647(2) _cell_length_b 9.9534(2) _cell_length_c 15.7079(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.5090(10) _cell_angle_gamma 90.00 _cell_volume 1463.49(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 area detector diffractometer ; _diffrn_measurement_method ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=0 degree settings ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11417 _diffrn_reflns_av_R_equivalents 0.0657 _diffrn_reflns_av_sigmaI/netI 0.0554 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3316 _reflns_number_gt 2394 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1999)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed (Barbour, 2001)' _computing_publication_material 'local program' _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^)+(0.0587P)^2^+0.2427P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens direct _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3316 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0721 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1285 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 O1 O 0.74680(11) 0.22924(11) -0.03221(7) 0.0409(3) Uani 1 1 d . . . C2 C 0.87989(18) 0.2485(2) 0.01265(11) 0.0464(4) Uani 1 1 d . . . H2 H 0.945(2) 0.1655(19) 0.0236(12) 0.055(5) Uiso 1 1 d . . . C3 C 0.89961(18) 0.37670(19) 0.03396(11) 0.0460(4) Uani 1 1 d . . . H3 H 0.989(2) 0.415(2) 0.0635(12) 0.056(5) Uiso 1 1 d . . . C4 C 0.77235(18) 0.44613(18) 0.00114(10) 0.0407(4) Uani 1 1 d . . . H4 H 0.7514(19) 0.531(2) 0.0033(11) 0.051(5) Uiso 1 1 d . . . C5 C 0.68054(15) 0.35229(15) -0.03838(9) 0.0323(3) Uani 1 1 d . . . C6 C 0.53553(16) 0.35981(15) -0.08241(9) 0.0328(3) Uani 1 1 d . . . H6 H 0.4902(17) 0.4529(18) -0.0807(10) 0.043(4) Uiso 1 1 d . . . N7 N 0.47103(13) 0.26007(12) -0.12053(8) 0.0339(3) Uani 1 1 d . . . C8 C 0.32388(16) 0.27904(15) -0.16259(9) 0.0329(3) Uani 1 1 d . . . H8 H 0.2889(17) 0.3711(16) -0.1485(10) 0.037(4) Uiso 1 1 d . . . C9 C 0.31787(17) 0.26507(18) -0.26000(10) 0.0392(4) Uani 1 1 d . . . C10 C 0.16514(18) 0.27388(18) -0.30634(11) 0.0427(4) Uani 1 1 d . . . C11 C 0.07202(18) 0.16709(19) -0.27283(10) 0.0439(4) Uani 1 1 d . . . C12 C 0.07656(17) 0.17879(19) -0.17585(10) 0.0407(4) Uani 1 1 d . . . C13 C 0.22938(16) 0.17300(15) -0.12806(9) 0.0338(3) Uani 1 1 d . . . H13 H 0.2732(16) 0.0839(16) -0.1383(9) 0.034(4) Uiso 1 1 d . . . N14 N 0.22602(13) 0.19521(13) -0.03657(8) 0.0343(3) Uani 1 1 d . . . C15 C 0.28132(15) 0.10570(15) 0.01529(9) 0.0328(3) Uani 1 1 d . . . H15 H 0.3326(18) 0.0262(17) -0.0045(10) 0.044(4) Uiso 1 1 d . . . C16 C 0.27731(15) 0.10885(14) 0.10716(9) 0.0327(3) Uani 1 1 d . . . C17 C 0.33060(17) 0.02138(16) 0.16970(10) 0.0379(4) Uani 1 1 d . . . H17 H 0.3847(19) -0.0560(18) 0.1603(11) 0.047(5) Uiso 1 1 d . . . C18 C 0.28815(17) 0.06825(17) 0.24742(10) 0.0402(4) Uani 1 1 d . . . H18 H 0.3075(17) 0.0315(17) 0.3022(11) 0.043(4) Uiso 1 1 d . . . C19 C 0.21277(18) 0.18045(18) 0.22726(11) 0.0427(4) Uani 1 1 d . . . H19 H 0.168(2) 0.2424(19) 0.2578(13) 0.055(5) Uiso 1 1 d . . . O20 O 0.20374(11) 0.20930(10) 0.14120(7) 0.0388(3) Uani 1 1 d . . . H9A H 0.379(2) 0.3390(19) -0.2791(12) 0.052(5) Uiso 1 1 d . . . H10A H 0.1230(19) 0.3691(18) -0.2951(11) 0.046(5) Uiso 1 1 d . . . H11A H -0.0287(19) 0.1732(17) -0.2997(11) 0.046(5) Uiso 1 1 d . . . H12A H 0.0305(19) 0.2679(18) -0.1598(11) 0.045(5) Uiso 1 1 d . . . H9B H 0.3609(18) 0.1800(17) -0.2722(10) 0.037(4) Uiso 1 1 d . . . H10B H 0.1685(17) 0.2639(15) -0.3691(12) 0.039(4) Uiso 1 1 d . . . H11B H 0.1081(19) 0.0765(19) -0.2868(11) 0.049(5) Uiso 1 1 d . . . H12B H 0.0257(17) 0.1066(16) -0.1532(10) 0.033(4) 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 O1 0.0365(6) 0.0416(6) 0.0429(6) -0.0043(5) -0.0001(5) 0.0041(5) C2 0.0328(8) 0.0615(11) 0.0434(10) 0.0011(8) 0.0007(7) 0.0019(8) C3 0.0357(9) 0.0644(12) 0.0368(9) 0.0052(8) 0.0018(7) -0.0124(8) C4 0.0482(9) 0.0387(9) 0.0351(9) -0.0022(7) 0.0054(7) -0.0063(8) C5 0.0339(7) 0.0375(8) 0.0257(7) 0.0007(6) 0.0046(6) 0.0002(6) C6 0.0379(8) 0.0353(8) 0.0255(7) -0.0011(6) 0.0059(6) 0.0034(7) N7 0.0329(7) 0.0376(7) 0.0306(7) -0.0038(5) 0.0026(5) 0.0008(5) C8 0.0304(7) 0.0369(8) 0.0304(8) -0.0027(6) 0.0014(6) 0.0050(6) C9 0.0366(8) 0.0491(10) 0.0315(8) -0.0026(7) 0.0037(7) 0.0055(8) C10 0.0407(9) 0.0577(11) 0.0283(8) -0.0014(7) 0.0005(7) 0.0070(8) C11 0.0383(9) 0.0533(10) 0.0365(9) -0.0083(7) -0.0062(7) 0.0034(8) C12 0.0336(8) 0.0513(10) 0.0361(9) -0.0025(7) 0.0016(6) -0.0016(8) C13 0.0359(8) 0.0335(8) 0.0311(8) -0.0034(6) 0.0013(6) 0.0025(7) N14 0.0327(6) 0.0385(7) 0.0312(7) -0.0022(5) 0.0028(5) 0.0029(5) C15 0.0319(7) 0.0315(8) 0.0349(8) -0.0030(6) 0.0045(6) -0.0008(6) C16 0.0313(7) 0.0322(7) 0.0344(8) -0.0024(6) 0.0042(6) -0.0006(6) C17 0.0417(8) 0.0351(8) 0.0365(8) 0.0001(7) 0.0051(7) 0.0002(7) C18 0.0464(9) 0.0437(9) 0.0298(8) 0.0025(7) 0.0036(7) -0.0027(8) C19 0.0434(9) 0.0494(10) 0.0366(9) -0.0070(7) 0.0104(7) 0.0014(8) O20 0.0386(6) 0.0411(6) 0.0372(6) -0.0007(5) 0.0068(5) 0.0071(5) _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 O1 C2 1.3628(19) . ? O1 C5 1.3728(18) . ? C2 C3 1.326(3) . ? C3 C4 1.418(2) . ? C4 C5 1.361(2) . ? C5 C6 1.445(2) . ? C6 N7 1.2683(19) . ? N7 C8 1.4628(18) . ? C8 C9 1.529(2) . ? C8 C13 1.534(2) . ? C9 C10 1.522(2) . ? C10 C11 1.524(3) . ? C11 C12 1.522(2) . ? C12 C13 1.529(2) . ? C13 N14 1.4591(19) . ? N14 C15 1.2669(19) . ? C15 C16 1.450(2) . ? C16 C17 1.353(2) . ? C16 O20 1.3714(17) . ? C17 C18 1.419(2) . ? C18 C19 1.338(2) . ? C19 O20 1.3722(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 C2 O1 C5 106.79(12) . . ? C3 C2 O1 110.52(15) . . ? C2 C3 C4 107.29(15) . . ? C5 C4 C3 106.38(15) . . ? C4 C5 O1 109.02(13) . . ? C4 C5 C6 132.83(15) . . ? O1 C5 C6 118.15(12) . . ? N7 C6 C5 122.84(14) . . ? C6 N7 C8 118.16(13) . . ? N7 C8 C9 109.41(12) . . ? N7 C8 C13 108.52(12) . . ? C9 C8 C13 110.74(12) . . ? C10 C9 C8 111.44(13) . . ? C9 C10 C11 110.59(14) . . ? C12 C11 C10 111.12(14) . . ? C11 C12 C13 111.91(13) . . ? N14 C13 C12 108.73(12) . . ? N14 C13 C8 110.06(12) . . ? C12 C13 C8 111.06(12) . . ? C15 N14 C13 117.36(13) . . ? N14 C15 C16 123.76(14) . . ? C17 C16 O20 110.01(13) . . ? C17 C16 C15 130.32(14) . . ? O20 C16 C15 119.57(12) . . ? C16 C17 C18 106.89(15) . . ? C19 C18 C17 106.24(15) . . ? C18 C19 O20 111.17(15) . . ? C16 O20 C19 105.68(12) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.233 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.041 #==================END data_bispyrrol _database_code_depnum_ccdc_archive 'CCDC 280848' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common N,N'-Bis(1H-pyrrol-2-ylmethylene)cyclohexane-1,2-diamine _chemical_melting_point ? _chemical_formula_moiety C4NH4CHNC6H10NCHC4NH4 _chemical_formula_sum 'C16 H20 N4' _chemical_formula_weight 134.18 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.5478(4) _cell_length_b 8.9189(2) _cell_length_c 9.2148(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.3880(10) _cell_angle_gamma 90.00 _cell_volume 1494.36(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9776 _exptl_absorpt_correction_T_max 0.9898 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 area detector diffractometer ; _diffrn_measurement_method ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=0 degree settings ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3200 _diffrn_reflns_av_R_equivalents 0.0113 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _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 2.24 _diffrn_reflns_theta_max 28.28 _reflns_number_total 1807 _reflns_number_gt 1663 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1999)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed (Barbour, 2001)' _computing_publication_material 'local program' _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^)+(0.0468P)^2^+0.8102P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens direct _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1807 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0989 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 0.14837(4) -0.16521(9) 0.07836(9) 0.0199(2) Uani 1 1 d . . . H1 H 0.1262(8) -0.1551(16) -0.0222(17) 0.039(4) Uiso 1 1 d . . . C2 C 0.19692(5) -0.27515(11) 0.13400(11) 0.0238(2) Uani 1 1 d . . . H2 H 0.2102(7) -0.3523(15) 0.0689(15) 0.035(3) Uiso 1 1 d . . . C3 C 0.21964(5) -0.25199(12) 0.28376(11) 0.0264(2) Uani 1 1 d . . . H3 H 0.2546(8) -0.3146(16) 0.3538(16) 0.040(4) Uiso 1 1 d . . . C4 C 0.18333(5) -0.12279(11) 0.32050(10) 0.0229(2) Uani 1 1 d . . . H4 H 0.1884(7) -0.0749(15) 0.4179(15) 0.033(3) Uiso 1 1 d . . . C5 C 0.13904(5) -0.07050(10) 0.19150(10) 0.0179(2) Uani 1 1 d . . . C6 C 0.09140(5) 0.05888(10) 0.16167(10) 0.0176(2) Uani 1 1 d . . . H6 H 0.0680(6) 0.0759(13) 0.0540(13) 0.023(3) Uiso 1 1 d . . . N7 N 0.07964(4) 0.14927(8) 0.26218(8) 0.0184(2) Uani 1 1 d . . . C8 C 0.03392(5) 0.28080(9) 0.21394(10) 0.0183(2) Uani 1 1 d . . . H8 H 0.0166(6) 0.2794(13) 0.1030(13) 0.020(3) Uiso 1 1 d . . . C9 C 0.07959(5) 0.42291(11) 0.25763(12) 0.0256(2) Uani 1 1 d . . . C10 C 0.03454(6) 0.56539(10) 0.21680(11) 0.0251(2) Uani 1 1 d . . . H9A H 0.0994(7) 0.4202(15) 0.3709(15) 0.031(3) Uiso 1 1 d . . . H10A H 0.0651(7) 0.6550(15) 0.2489(15) 0.033(3) Uiso 1 1 d . . . H9B H 0.1237(8) 0.4206(16) 0.2107(15) 0.038(4) Uiso 1 1 d . . . H10B H 0.0194(7) 0.5720(15) 0.1045(15) 0.034(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 N1 0.0235(4) 0.0190(4) 0.0172(4) 0.0004(3) 0.0043(3) 0.0021(3) C2 0.0251(4) 0.0213(5) 0.0267(5) 0.0017(4) 0.0088(4) 0.0054(3) C3 0.0243(5) 0.0282(5) 0.0259(5) 0.0050(4) 0.0027(4) 0.0076(4) C4 0.0242(4) 0.0244(5) 0.0189(5) 0.0010(3) 0.0010(3) 0.0030(3) C5 0.0193(4) 0.0168(4) 0.0175(4) 0.0002(3) 0.0035(3) -0.0009(3) C6 0.0189(4) 0.0169(4) 0.0166(4) 0.0018(3) 0.0022(3) -0.0012(3) N7 0.0217(4) 0.0151(4) 0.0179(4) 0.0015(3) 0.0026(3) 0.0002(3) C8 0.0234(4) 0.0145(4) 0.0170(4) 0.0020(3) 0.0037(3) 0.0014(3) C9 0.0250(5) 0.0166(4) 0.0353(6) 0.0017(4) 0.0066(4) -0.0021(3) C10 0.0332(5) 0.0146(4) 0.0280(5) 0.0024(3) 0.0068(4) -0.0014(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 N1 C2 1.3613(12) . ? N1 C5 1.3790(11) . ? C2 C3 1.3766(14) . ? C3 C4 1.4093(14) . ? C4 C5 1.3856(12) . ? C5 C6 1.4464(12) . ? C6 N7 1.2786(12) . ? N7 C8 1.4642(11) . ? C8 C9 1.5334(12) . ? C8 C8 1.5346(17) 2 ? C9 C10 1.5266(13) . ? C10 C10 1.525(2) 2 ? 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 C2 N1 C5 109.20(8) . . ? N1 C2 C3 108.56(8) . . ? C2 C3 C4 107.30(8) . . ? C5 C4 C3 107.43(8) . . ? N1 C5 C4 107.50(8) . . ? N1 C5 C6 120.55(8) . . ? C4 C5 C6 131.92(8) . . ? N7 C6 C5 123.41(8) . . ? C6 N7 C8 117.17(7) . . ? N7 C8 C9 109.01(7) . . ? N7 C8 C8 110.11(6) . 2 ? C9 C8 C8 110.12(6) . 2 ? C10 C9 C8 112.10(8) . . ? C10 C10 C9 111.31(6) 2 . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.273 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.033 #==================END data_dipyridine _database_code_depnum_ccdc_archive 'CCDC 280849' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;(N-Pyridin-4-ylmethylene)(N'-pyridin-2-ylmethylene) cyclohexane-1,2-diamine ; _chemical_melting_point ? _chemical_formula_moiety C5NH4CHNC6H10NCHC5NH4 _chemical_formula_sum 'C18 H20 N4' _chemical_formula_weight 292.38 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 35.5824(14) _cell_length_b 5.7010(3) _cell_length_c 16.8318(9) _cell_angle_alpha 90.00 _cell_angle_beta 112.752(2) _cell_angle_gamma 90.00 _cell_volume 3148.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9747 _exptl_absorpt_correction_T_max 0.9925 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 396(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 area detector diffractometer ; _diffrn_measurement_method ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=0 degree settings ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11262 _diffrn_reflns_av_R_equivalents 0.1037 _diffrn_reflns_av_sigmaI/netI 0.0978 _diffrn_reflns_limit_h_min -46 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3804 _reflns_number_gt 2278 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1999)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed (Barbour, 2001)' _computing_publication_material 'local program' _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^)+(0.0833P)^2^+1.5120P] 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 3804 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1266 _refine_ls_R_factor_gt 0.0665 _refine_ls_wR_factor_ref 0.1844 _refine_ls_wR_factor_gt 0.1574 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 0.08119(6) 1.0234(4) 0.12361(13) 0.0307(5) Uani 1 1 d . . . H1 H 0.1063 1.0208 0.1187 0.037 Uiso 1 1 calc R . . C2 C 0.07181(7) 1.1991(4) 0.16802(14) 0.0366(5) Uani 1 1 d . . . H2 H 0.0909 1.3156 0.1941 0.044 Uiso 1 1 calc R . . C3 C 0.03476(7) 1.2060(4) 0.17455(15) 0.0368(6) Uani 1 1 d . . . H3 H 0.0280 1.3269 0.2037 0.044 Uiso 1 1 calc R . . C4 C 0.00788(7) 1.0286(5) 0.13667(16) 0.0440(6) Uani 1 1 d . . . H4 H -0.0173 1.0322 0.1413 0.053 Uiso 1 1 calc R . . N5 N 0.01566(6) 0.8471(4) 0.09261(13) 0.0416(5) Uani 1 1 d . . . C6 C 0.05258(6) 0.8485(4) 0.08584(12) 0.0269(5) Uani 1 1 d . . . C7 C 0.06040(6) 0.6526(4) 0.03756(13) 0.0292(5) Uani 1 1 d . . . H7 H 0.0423 0.5269 0.0216 0.035 Uiso 1 1 calc R . . N8 N 0.09125(5) 0.6507(3) 0.01712(11) 0.0301(4) Uani 1 1 d . . . C9 C 0.09703(6) 0.4432(4) -0.02741(13) 0.0285(5) Uani 1 1 d . . . H9 H 0.0832 0.3096 -0.0140 0.034 Uiso 1 1 calc R . . C10 C 0.07950(7) 0.4827(4) -0.12487(13) 0.0345(5) Uani 1 1 d . . . H10A H 0.0504 0.5106 -0.1447 0.041 Uiso 1 1 calc R . . H10B H 0.0919 0.6210 -0.1380 0.041 Uiso 1 1 calc R . . C11 C 0.08705(7) 0.2734(4) -0.17226(14) 0.0355(5) Uani 1 1 d . . . H11A H 0.0774 0.3090 -0.2333 0.043 Uiso 1 1 calc R . . H11B H 0.0717 0.1400 -0.1652 0.043 Uiso 1 1 calc R . . C12 C 0.13204(7) 0.2098(4) -0.13918(14) 0.0375(6) Uani 1 1 d . . . H12A H 0.1468 0.3337 -0.1540 0.045 Uiso 1 1 calc R . . H12B H 0.1353 0.0668 -0.1670 0.045 Uiso 1 1 calc R . . C13 C 0.14986(7) 0.1747(4) -0.04193(14) 0.0349(5) Uani 1 1 d . . . H13A H 0.1789 0.1450 -0.0225 0.042 Uiso 1 1 calc R . . H13B H 0.1373 0.0390 -0.0275 0.042 Uiso 1 1 calc R . . C14 C 0.14280(6) 0.3902(4) 0.00416(13) 0.0288(5) Uani 1 1 d . . . H14 H 0.1567 0.5251 -0.0083 0.035 Uiso 1 1 calc R . . N15 N 0.15901(5) 0.3509(3) 0.09710(11) 0.0298(4) Uani 1 1 d . . . C16 C 0.18014(6) 0.5139(4) 0.14457(13) 0.0286(5) Uani 1 1 d . . . H16 H 0.1849 0.6488 0.1188 0.034 Uiso 1 1 calc R . . C17 C 0.19764(6) 0.4971(4) 0.23979(13) 0.0276(5) Uani 1 1 d . . . C18 C 0.21996(6) 0.6802(4) 0.28684(14) 0.0302(5) Uani 1 1 d . . . H18 H 0.2238 0.8140 0.2593 0.036 Uiso 1 1 calc R . . C19 C 0.23672(7) 0.6657(4) 0.37533(16) 0.0400(6) Uani 1 1 d . . . H19 H 0.2518 0.7927 0.4060 0.048 Uiso 1 1 calc R . . N20 N 0.23258(6) 0.4799(4) 0.41991(13) 0.0477(6) Uani 1 1 d . . . C21 C 0.21020(8) 0.2986(4) 0.37218(16) 0.0456(6) Uani 1 1 d . . . H21 H 0.2067 0.1663 0.4009 0.055 Uiso 1 1 calc R . . C22 C 0.19249(7) 0.3012(4) 0.28362(15) 0.0354(5) Uani 1 1 d . . . H22 H 0.1773 0.1737 0.2535 0.043 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 C1 0.0288(11) 0.0373(12) 0.0274(11) 0.0069(9) 0.0124(9) 0.0040(9) C2 0.0414(14) 0.0324(12) 0.0344(13) 0.0015(9) 0.0128(11) -0.0018(10) C3 0.0423(14) 0.0370(12) 0.0362(13) 0.0060(10) 0.0207(11) 0.0132(11) C4 0.0350(13) 0.0586(16) 0.0458(15) 0.0146(12) 0.0239(12) 0.0158(12) N5 0.0326(11) 0.0515(12) 0.0403(11) 0.0080(9) 0.0138(9) 0.0041(9) C6 0.0269(11) 0.0335(11) 0.0210(10) 0.0076(8) 0.0101(8) 0.0068(9) C7 0.0266(11) 0.0339(12) 0.0254(11) 0.0039(8) 0.0081(9) -0.0004(9) N8 0.0300(10) 0.0354(10) 0.0262(9) 0.0005(7) 0.0123(8) 0.0009(8) C9 0.0273(11) 0.0341(11) 0.0256(11) -0.0025(8) 0.0120(9) -0.0022(9) C10 0.0335(12) 0.0417(13) 0.0261(11) -0.0012(9) 0.0093(9) 0.0018(10) C11 0.0346(13) 0.0425(13) 0.0281(12) -0.0047(9) 0.0106(10) -0.0032(10) C12 0.0340(13) 0.0481(14) 0.0327(13) -0.0134(10) 0.0153(10) -0.0042(10) C13 0.0263(11) 0.0419(13) 0.0339(12) -0.0083(10) 0.0087(9) 0.0006(10) C14 0.0261(11) 0.0345(11) 0.0267(11) -0.0028(9) 0.0111(9) -0.0037(9) N15 0.0258(9) 0.0341(10) 0.0285(10) -0.0023(8) 0.0091(8) 0.0005(8) C16 0.0265(11) 0.0322(11) 0.0286(12) -0.0004(9) 0.0124(9) -0.0004(9) C17 0.0196(10) 0.0342(12) 0.0296(12) -0.0015(8) 0.0102(9) 0.0032(9) C18 0.0243(11) 0.0323(11) 0.0336(12) 0.0005(9) 0.0108(9) -0.0023(9) C19 0.0269(12) 0.0446(14) 0.0415(14) -0.0044(11) 0.0056(10) -0.0020(10) N20 0.0374(12) 0.0566(14) 0.0413(12) 0.0045(10) 0.0067(9) 0.0052(10) C21 0.0503(16) 0.0422(14) 0.0431(15) 0.0130(11) 0.0165(12) 0.0041(12) C22 0.0351(13) 0.0335(12) 0.0356(13) 0.0005(9) 0.0114(10) -0.0017(10) _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 C2 1.366(3) . ? C1 C6 1.391(3) . ? C2 C3 1.365(3) . ? C3 C4 1.368(3) . ? C4 N5 1.363(3) . ? N5 C6 1.362(3) . ? C6 C7 1.470(3) . ? C7 N8 1.271(3) . ? N8 C9 1.457(3) . ? C9 C10 1.530(3) . ? C9 C14 1.535(3) . ? C10 C11 1.516(3) . ? C11 C12 1.521(3) . ? C12 C13 1.523(3) . ? C13 C14 1.525(3) . ? C14 N15 1.460(3) . ? N15 C16 1.266(3) . ? C16 C17 1.481(3) . ? C17 C18 1.364(3) . ? C17 C22 1.389(3) . ? C18 C19 1.376(3) . ? C19 N20 1.339(3) . ? N20 C21 1.361(3) . ? C21 C22 1.376(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 C2 C1 C6 119.0(2) . . ? C3 C2 C1 120.8(2) . . ? C2 C3 C4 117.7(2) . . ? N5 C4 C3 124.2(2) . . ? C6 N5 C4 116.5(2) . . ? N5 C6 C1 121.69(19) . . ? N5 C6 C7 115.91(19) . . ? C1 C6 C7 122.40(19) . . ? N8 C7 C6 121.61(19) . . ? C7 N8 C9 117.02(18) . . ? N8 C9 C10 110.61(17) . . ? N8 C9 C14 108.88(16) . . ? C10 C9 C14 109.76(16) . . ? C11 C10 C9 111.52(18) . . ? C10 C11 C12 111.75(18) . . ? C11 C12 C13 111.51(18) . . ? C12 C13 C14 111.05(18) . . ? N15 C14 C13 110.32(17) . . ? N15 C14 C9 109.11(15) . . ? C13 C14 C9 110.13(17) . . ? C16 N15 C14 117.12(17) . . ? N15 C16 C17 122.29(19) . . ? C18 C17 C22 118.27(19) . . ? C18 C17 C16 119.04(19) . . ? C22 C17 C16 122.68(18) . . ? C17 C18 C19 119.6(2) . . ? N20 C19 C18 124.0(2) . . ? C19 N20 C21 115.9(2) . . ? N20 C21 C22 123.3(2) . . ? C21 C22 C17 119.0(2) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.299 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.072 #==================END