Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Mei Wang' _publ_contact_author_address ; School of Chemical Engineering Dalian University of Technology Zhongshan Road 158-46 Dalian Liaoning 116012 CHINA ; _publ_contact_author_email SYMBUENO@DLUT.EDU.CN _publ_section_title ; Carbene-pyridine chelating 2Fe2S hydrogenase model complexes as highly active catalysts for electrochemical reduction of protons from week acid HOAc ; _publ_contact_author ;Mei Wang Dalian University of technology, Zhongshan Road 158-46, 116012 Dalian, P. R. China, Fax: +86-411-83702185 ; loop_ _publ_author_name 'Mei Wang.' 'Lele Duan.' 'Ping li.' 'Yong Na.' 'Licheng Sun.' 'Ning Wang.' data_1 _database_code_depnum_ccdc_archive 'CCDC 625995' #------------------------------------------------------------------------------ _audit_creation_date 'Oct 31 18:25:00 2006' _audit_creation_method SHELXL-97 _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SMART (Bruker, 1997)' _computing_data_reduction 'SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXP97 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (Bruker, 1997)' #------------------------------------------------------------------------------ _chemical_compound_source ? _chemical_name_common ? _chemical_formula_weight 489.13 _chemical_formula_analytical ? _chemical_formula_sum 'C16 H15 Fe2 N3 O4 S2' _chemical_formula_moiety 'C16 H15 Fe2 N3 O4 S2' _chemical_formula_structural ? _chemical_melting_point ? #------------------------------------------------------------------------------ _cell_length_a 30.443(4) _cell_length_b 7.6038(11) _cell_length_c 18.798(3) _cell_angle_alpha 90.00 _cell_angle_beta 120.551(2) _cell_angle_gamma 90.00 _cell_volume 3747.4(9) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3885 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 25.99 #------------------------------------------------------------------------------ _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' _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.734 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1984 _exptl_absorpt_coefficient_mu 1.799 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6824 _exptl_absorpt_correction_T_max 0.7741 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 273(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 9922 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 26.07 _reflns_number_total 3703 _reflns_number_gt 3130 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 0.995 #------------------------------------------------------------------------------ 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #------------------------------------------------------------------------------ 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 Fe1 Fe 0.097273(14) 0.55447(5) 0.26030(2) 0.03831(12) Uani 1 1 d . . . Fe2 Fe 0.127333(14) 0.85921(4) 0.24600(2) 0.03379(12) Uani 1 1 d . . . S1 S 0.04570(2) 0.79189(9) 0.20181(4) 0.04229(17) Uani 1 1 d . . . S2 S 0.12662(3) 0.62499(8) 0.17523(4) 0.04239(18) Uani 1 1 d . . . N1 N 0.13279(9) 0.9762(3) 0.34603(13) 0.0398(5) Uani 1 1 d . . . N2 N 0.21628(9) 0.9176(3) 0.39681(13) 0.0473(6) Uani 1 1 d . . . N3 N 0.24408(9) 0.8230(3) 0.31943(16) 0.0515(6) Uani 1 1 d . . . O1 O 0.01940(10) 0.2823(3) 0.17627(14) 0.0765(7) Uani 1 1 d . . . O2 O 0.09688(10) 0.6086(4) 0.41400(14) 0.0774(7) Uani 1 1 d . . . O3 O 0.19064(9) 0.3499(3) 0.35225(14) 0.0673(6) Uani 1 1 d . . . O4 O 0.11986(11) 1.1471(3) 0.13899(15) 0.0765(7) Uani 1 1 d . . . C1 C 0.04973(12) 0.3863(4) 0.20793(17) 0.0504(7) Uani 1 1 d . . . C2 C 0.09533(12) 0.5897(4) 0.35204(18) 0.0506(7) Uani 1 1 d . . . C3 C 0.15350(12) 0.4304(4) 0.31607(17) 0.0450(6) Uani 1 1 d . . . C4 C 0.12313(11) 1.0357(4) 0.18364(17) 0.0453(6) Uani 1 1 d . . . C5 C 0.20023(10) 0.8567(3) 0.31710(16) 0.0386(6) Uani 1 1 d . . . C6 C 0.00671(11) 0.7624(5) 0.09000(17) 0.0614(8) Uani 1 1 d . . . H6A H -0.0119 0.6527 0.0793 0.074 Uiso 1 1 calc R . . H6B H -0.0182 0.8566 0.0678 0.074 Uiso 1 1 calc R . . C7 C 0.03500(13) 0.7597(5) 0.04367(17) 0.0641(9) Uani 1 1 d . . . H7A H 0.0104 0.7482 -0.0148 0.077 Uiso 1 1 calc R . . H7B H 0.0522 0.8718 0.0518 0.077 Uiso 1 1 calc R . . C8 C 0.07349(13) 0.6161(4) 0.06837(17) 0.0570(8) Uani 1 1 d . . . H8A H 0.0873 0.6193 0.0319 0.068 Uiso 1 1 calc R . . H8B H 0.0562 0.5043 0.0599 0.068 Uiso 1 1 calc R . . C9 C 0.09453(13) 1.0459(4) 0.35541(19) 0.0533(7) Uani 1 1 d . . . H9A H 0.0616 1.0453 0.3099 0.064 Uiso 1 1 calc R . . C10 C 0.10182(14) 1.1156(4) 0.4269(2) 0.0635(9) Uani 1 1 d . . . H10A H 0.0747 1.1616 0.4305 0.076 Uiso 1 1 calc R . . C11 C 0.15103(14) 1.1163(5) 0.4948(2) 0.0676(9) Uani 1 1 d . . . H11A H 0.1572 1.1616 0.5451 0.081 Uiso 1 1 calc R . . C12 C 0.18989(14) 1.0508(4) 0.48758(18) 0.0629(9) Uani 1 1 d . . . H12A H 0.2230 1.0516 0.5326 0.075 Uiso 1 1 calc R . . C13 C 0.17993(11) 0.9823(4) 0.41236(16) 0.0453(6) Uani 1 1 d . . . C14 C 0.26947(12) 0.9195(5) 0.4447(2) 0.0609(8) Uani 1 1 d . . . H14A H 0.2890 0.9553 0.4995 0.073 Uiso 1 1 calc R . . C15 C 0.28665(13) 0.8614(4) 0.3981(2) 0.0633(8) Uani 1 1 d . . . H15A H 0.3208 0.8476 0.4138 0.076 Uiso 1 1 calc R . . C16 C 0.24880(14) 0.7712(5) 0.2506(2) 0.0700(9) Uani 1 1 d . . . H16C H 0.2208 0.8185 0.2008 0.105 Uiso 1 1 calc R . . H16D H 0.2484 0.6452 0.2472 0.105 Uiso 1 1 calc R . . H16A H 0.2803 0.8152 0.2577 0.105 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 Fe1 0.0420(2) 0.0409(2) 0.0357(2) -0.00276(15) 0.02246(18) -0.00761(16) Fe2 0.0340(2) 0.0356(2) 0.0345(2) -0.00437(14) 0.01930(17) -0.00399(15) S1 0.0350(3) 0.0535(4) 0.0388(3) -0.0009(3) 0.0191(3) -0.0033(3) S2 0.0519(4) 0.0422(4) 0.0435(4) -0.0095(3) 0.0318(3) -0.0097(3) N1 0.0451(13) 0.0376(11) 0.0382(12) -0.0031(9) 0.0223(11) -0.0006(10) N2 0.0401(13) 0.0494(13) 0.0400(12) -0.0026(10) 0.0114(11) -0.0051(10) N3 0.0458(14) 0.0500(14) 0.0625(16) 0.0025(11) 0.0304(13) 0.0019(11) O1 0.0735(16) 0.0722(16) 0.0650(15) -0.0057(12) 0.0215(13) -0.0330(14) O2 0.095(2) 0.1028(19) 0.0543(14) 0.0068(12) 0.0524(15) 0.0155(15) O3 0.0544(14) 0.0739(15) 0.0634(14) 0.0041(11) 0.0225(12) 0.0070(12) O4 0.103(2) 0.0589(14) 0.0680(15) 0.0102(11) 0.0438(15) -0.0143(13) C1 0.0528(18) 0.0543(18) 0.0417(15) -0.0009(13) 0.0223(14) -0.0132(14) C2 0.0520(18) 0.0557(17) 0.0492(17) 0.0054(13) 0.0294(15) 0.0034(14) C3 0.0497(18) 0.0489(16) 0.0393(15) -0.0056(12) 0.0246(14) -0.0085(14) C4 0.0499(17) 0.0425(15) 0.0449(15) -0.0050(12) 0.0251(14) -0.0063(13) C5 0.0358(14) 0.0336(13) 0.0467(15) 0.0020(10) 0.0211(12) -0.0036(11) C6 0.0436(17) 0.086(2) 0.0406(16) 0.0000(16) 0.0116(14) -0.0097(16) C7 0.069(2) 0.079(2) 0.0332(15) -0.0068(15) 0.0183(15) -0.0221(19) C8 0.073(2) 0.066(2) 0.0370(15) -0.0129(13) 0.0317(16) -0.0208(17) C9 0.0605(19) 0.0528(17) 0.0514(17) -0.0029(13) 0.0321(16) 0.0038(15) C10 0.070(2) 0.069(2) 0.062(2) -0.0048(16) 0.0413(19) 0.0133(17) C11 0.068(2) 0.084(2) 0.0454(18) -0.0119(16) 0.0244(18) 0.0080(18) C12 0.068(2) 0.070(2) 0.0380(15) -0.0114(14) 0.0175(16) -0.0034(17) C13 0.0500(17) 0.0419(14) 0.0391(14) -0.0018(11) 0.0192(13) -0.0028(13) C14 0.0418(17) 0.078(2) 0.0470(17) -0.0047(16) 0.0109(15) -0.0037(15) C15 0.0407(17) 0.069(2) 0.064(2) 0.0006(16) 0.0148(16) -0.0026(15) C16 0.069(2) 0.069(2) 0.085(2) -0.0175(19) 0.050(2) -0.0037(18) #------------------------------------------------------------------------------ _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^)+(0.0543P)^2^+0.6365P] 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 3703 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0894 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.587 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.074 #------------------------------------------------------------------------------ _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 Fe1 C3 1.759(3) . ? Fe1 C2 1.776(3) . ? Fe1 C1 1.803(3) . ? Fe1 S2 2.2571(7) . ? Fe1 S1 2.2755(8) . ? Fe1 Fe2 2.5552(6) . ? Fe2 C4 1.743(3) . ? Fe2 C5 1.923(3) . ? Fe2 N1 2.009(2) . ? Fe2 S2 2.2165(7) . ? Fe2 S1 2.2425(8) . ? S1 C6 1.828(3) . ? S2 C8 1.831(3) . ? N1 C13 1.341(3) . ? N1 C9 1.370(4) . ? N2 C13 1.372(4) . ? N2 C14 1.397(4) . ? N2 C5 1.398(3) . ? N3 C5 1.338(3) . ? N3 C15 1.416(4) . ? N3 C16 1.427(4) . ? O1 C1 1.128(3) . ? O2 C2 1.151(3) . ? O3 C3 1.155(3) . ? O4 C4 1.160(3) . ? C6 C7 1.505(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.493(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.354(4) . ? C9 H9A 0.9300 . ? C10 C11 1.389(5) . ? C10 H10A 0.9300 . ? C11 C12 1.353(5) . ? C11 H11A 0.9300 . ? C12 C13 1.388(4) . ? C12 H12A 0.9300 . ? C14 C15 1.304(5) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 H16C 0.9600 . ? C16 H16D 0.9600 . ? C16 H16A 0.9600 . ? #------------------------------------------------------------------------------ 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 C3 Fe1 C2 90.28(13) . . ? C3 Fe1 C1 102.29(14) . . ? C2 Fe1 C1 102.92(13) . . ? C3 Fe1 S2 86.22(9) . . ? C2 Fe1 S2 150.78(10) . . ? C1 Fe1 S2 106.18(9) . . ? C3 Fe1 S1 159.51(9) . . ? C2 Fe1 S1 89.66(10) . . ? C1 Fe1 S1 97.68(10) . . ? S2 Fe1 S1 83.89(3) . . ? C3 Fe1 Fe2 104.89(9) . . ? C2 Fe1 Fe2 98.96(10) . . ? C1 Fe1 Fe2 144.77(9) . . ? S2 Fe1 Fe2 54.422(19) . . ? S1 Fe1 Fe2 54.95(2) . . ? C4 Fe2 C5 98.01(12) . . ? C4 Fe2 N1 103.38(10) . . ? C5 Fe2 N1 80.60(10) . . ? C4 Fe2 S2 103.89(9) . . ? C5 Fe2 S2 93.73(8) . . ? N1 Fe2 S2 152.66(6) . . ? C4 Fe2 S1 103.76(10) . . ? C5 Fe2 S1 157.74(8) . . ? N1 Fe2 S1 89.81(7) . . ? S2 Fe2 S1 85.60(3) . . ? C4 Fe2 Fe1 149.44(9) . . ? C5 Fe2 Fe1 105.45(7) . . ? N1 Fe2 Fe1 99.59(6) . . ? S2 Fe2 Fe1 55.92(2) . . ? S1 Fe2 Fe1 56.17(2) . . ? C6 S1 Fe2 113.81(10) . . ? C6 S1 Fe1 110.10(13) . . ? Fe2 S1 Fe1 68.88(2) . . ? C8 S2 Fe2 114.94(11) . . ? C8 S2 Fe1 108.76(10) . . ? Fe2 S2 Fe1 69.66(2) . . ? C13 N1 C9 116.4(2) . . ? C13 N1 Fe2 115.20(18) . . ? C9 N1 Fe2 128.3(2) . . ? C13 N2 C14 131.0(2) . . ? C13 N2 C5 117.8(2) . . ? C14 N2 C5 110.7(2) . . ? C5 N3 C15 111.3(3) . . ? C5 N3 C16 125.6(3) . . ? C15 N3 C16 122.9(3) . . ? O1 C1 Fe1 178.2(3) . . ? O2 C2 Fe1 176.0(3) . . ? O3 C3 Fe1 179.3(3) . . ? O4 C4 Fe2 176.5(2) . . ? N3 C5 N2 103.2(2) . . ? N3 C5 Fe2 143.6(2) . . ? N2 C5 Fe2 113.15(18) . . ? C7 C6 S1 116.0(2) . . ? C7 C6 H6A 108.3 . . ? S1 C6 H6A 108.3 . . ? C7 C6 H6B 108.3 . . ? S1 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? C8 C7 C6 114.8(3) . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7A 108.6 . . ? C8 C7 H7B 108.6 . . ? C6 C7 H7B 108.6 . . ? H7A C7 H7B 107.5 . . ? C7 C8 S2 115.5(2) . . ? C7 C8 H8A 108.4 . . ? S2 C8 H8A 108.4 . . ? C7 C8 H8B 108.4 . . ? S2 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? C10 C9 N1 123.9(3) . . ? C10 C9 H9A 118.0 . . ? N1 C9 H9A 118.0 . . ? C9 C10 C11 118.0(3) . . ? C9 C10 H10A 121.0 . . ? C11 C10 H10A 121.0 . . ? C12 C11 C10 119.7(3) . . ? C12 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? C11 C12 C13 119.4(3) . . ? C11 C12 H12A 120.3 . . ? C13 C12 H12A 120.3 . . ? N1 C13 N2 112.8(2) . . ? N1 C13 C12 122.5(3) . . ? N2 C13 C12 124.7(3) . . ? C15 C14 N2 107.0(3) . . ? C15 C14 H14A 126.5 . . ? N2 C14 H14A 126.5 . . ? C14 C15 N3 107.8(3) . . ? C14 C15 H15A 126.1 . . ? N3 C15 H15A 126.1 . . ? N3 C16 H16C 109.5 . . ? N3 C16 H16D 109.5 . . ? H16C C16 H16D 109.5 . . ? N3 C16 H16A 109.5 . . ? H16C C16 H16A 109.5 . . ? H16D C16 H16A 109.5 . . ? #===END # Copyright The Royal Society of Chemistry, 2006 # CCDC Number: 625996 data_Py608 _database_code_depnum_ccdc_archive 'CCDC 625996' #------------------------------------------------------------------------------ _audit_creation_date 'Oct 31 18:25:00 2006' _audit_creation_method SHELXL-97 _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SMART (Bruker, 1997)' _computing_data_reduction 'SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXP97 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (Bruker, 1997)' #------------------------------------------------------------------------------ _chemical_compound_source ? _chemical_name_common ? _chemical_formula_weight 608.25 _chemical_formula_analytical ? _chemical_formula_sum 'C23 H20 Fe2 N4 O5 S2' _chemical_formula_moiety 'C23 H20 Fe2 N4 O5 S2' _chemical_formula_structural ? _chemical_melting_point ? #------------------------------------------------------------------------------ _cell_length_a 12.445(9) _cell_length_b 14.269(10) _cell_length_c 28.52(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5065(6) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 2753 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 20.22 #------------------------------------------------------------------------------ _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.595 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2480 _exptl_absorpt_coefficient_mu 1.352 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7033 _exptl_absorpt_correction_T_max 0.8766 _exptl_absorpt_process_details SADABS #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 273(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 26670 _diffrn_reflns_av_R_equivalents 0.0787 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.13 _reflns_number_total 5029 _reflns_number_gt 3369 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.13 _diffrn_measured_fraction_theta_full 0.994 #------------------------------------------------------------------------------ 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #------------------------------------------------------------------------------ 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 Fe1 Fe 0.47623(4) 0.06539(4) 0.404788(18) 0.04375(17) Uani 1 1 d . . . Fe2 Fe 0.64490(4) 0.14866(4) 0.377665(17) 0.03576(15) Uani 1 1 d . . . S1 S 0.54276(7) 0.05478(7) 0.33110(3) 0.0444(3) Uani 1 1 d . . . S2 S 0.64317(7) 0.02535(7) 0.42790(3) 0.0455(3) Uani 1 1 d . . . N1 N 0.6671(3) 0.0572(3) 0.21060(12) 0.0650(10) Uani 1 1 d . . . N2 N 0.8236(2) 0.1615(2) 0.30520(9) 0.0394(7) Uani 1 1 d . . . N3 N 0.8885(2) 0.1496(2) 0.37394(9) 0.0411(8) Uani 1 1 d . . . N4 N 0.9691(3) -0.0243(3) 0.42063(11) 0.0556(9) Uani 1 1 d . . . O1 O 0.3822(3) -0.1226(2) 0.41488(13) 0.0897(11) Uani 1 1 d . . . O2 O 0.3004(3) 0.1787(3) 0.36741(12) 0.0928(12) Uani 1 1 d . . . O3 O 0.4430(3) 0.1561(3) 0.49571(11) 0.0883(11) Uani 1 1 d . . . O4 O 0.5502(2) 0.3043(2) 0.32564(11) 0.0715(9) Uani 1 1 d . . . C1 C 0.4152(3) -0.0481(4) 0.41113(15) 0.0601(12) Uani 1 1 d . . . C2 C 0.3690(3) 0.1338(3) 0.38161(14) 0.0585(12) Uani 1 1 d . . . C3 C 0.4559(3) 0.1185(3) 0.46094(16) 0.0570(12) Uani 1 1 d . . . C4 C 0.5903(3) 0.2439(3) 0.34613(13) 0.0459(10) Uani 1 1 d . . . C5 C 0.6678(3) 0.2173(3) 0.42812(14) 0.0431(9) Uani 1 1 d . . . C6 C 0.7928(3) 0.1494(2) 0.35093(11) 0.0345(8) Uani 1 1 d . . . C7 C 0.5962(3) -0.0628(3) 0.32221(14) 0.0563(11) Uani 1 1 d . . . H7A H 0.5419 -0.1079 0.3316 0.068 Uiso 1 1 calc R . . H7B H 0.6095 -0.0716 0.2890 0.068 Uiso 1 1 calc R . . C8 C 0.6983(3) -0.0839(3) 0.34855(15) 0.0611(12) Uani 1 1 d . . . H8A H 0.7249 -0.1446 0.3385 0.073 Uiso 1 1 calc R . . H8B H 0.7519 -0.0375 0.3401 0.073 Uiso 1 1 calc R . . C9 C 0.6866(3) -0.0848(3) 0.40103(15) 0.0587(12) Uani 1 1 d . . . H9A H 0.7553 -0.1022 0.4146 0.070 Uiso 1 1 calc R . . H9B H 0.6354 -0.1332 0.4094 0.070 Uiso 1 1 calc R . . C10 C 0.6579(5) -0.0228(4) 0.18705(17) 0.0838(16) Uani 1 1 d . . . H10A H 0.6003 -0.0287 0.1665 0.101 Uiso 1 1 calc R . . C11 C 0.7269(5) -0.0969(4) 0.19085(17) 0.0810(16) Uani 1 1 d . . . H11A H 0.7165 -0.1512 0.1734 0.097 Uiso 1 1 calc R . . C12 C 0.8122(4) -0.0887(3) 0.22122(17) 0.0678(13) Uani 1 1 d . . . H12A H 0.8612 -0.1374 0.2247 0.081 Uiso 1 1 calc R . . C13 C 0.8237(3) -0.0066(3) 0.24654(14) 0.0528(11) Uani 1 1 d . . . H13A H 0.8802 0.0005 0.2676 0.063 Uiso 1 1 calc R . . C14 C 0.7499(3) 0.0645(3) 0.24005(12) 0.0437(10) Uani 1 1 d . . . C15 C 0.7542(3) 0.1585(3) 0.26424(12) 0.0458(10) Uani 1 1 d . . . H15A H 0.7789 0.2051 0.2419 0.055 Uiso 1 1 calc R . . H15B H 0.6820 0.1758 0.2737 0.055 Uiso 1 1 calc R . . C16 C 0.9337(3) 0.1693(3) 0.30109(13) 0.0487(10) Uani 1 1 d . . . H16A H 0.9723 0.1785 0.2735 0.058 Uiso 1 1 calc R . . C17 C 0.9741(3) 0.1611(3) 0.34406(14) 0.0518(11) Uani 1 1 d . . . H17A H 1.0464 0.1628 0.3523 0.062 Uiso 1 1 calc R . . C18 C 0.9048(3) 0.1351(3) 0.42444(12) 0.0472(10) Uani 1 1 d . . . H18A H 0.8379 0.1145 0.4385 0.057 Uiso 1 1 calc R . . H18B H 0.9248 0.1941 0.4389 0.057 Uiso 1 1 calc R . . C19 C 0.9910(3) 0.0633(3) 0.43426(12) 0.0434(10) Uani 1 1 d . . . C20 C 1.0838(3) 0.0871(3) 0.45699(13) 0.0594(12) Uani 1 1 d . . . H20A H 1.0965 0.1488 0.4661 0.071 Uiso 1 1 calc R . . C21 C 1.1583(3) 0.0177(5) 0.46621(15) 0.0745(16) Uani 1 1 d . . . H21A H 1.2223 0.0322 0.4814 0.089 Uiso 1 1 calc R . . C22 C 1.1371(4) -0.0722(4) 0.45291(16) 0.0722(15) Uani 1 1 d . . . H22A H 1.1854 -0.1203 0.4593 0.087 Uiso 1 1 calc R . . C23 C 1.0427(4) -0.0893(4) 0.42991(15) 0.0651(13) Uani 1 1 d . . . H23A H 1.0291 -0.1503 0.4201 0.078 Uiso 1 1 calc R . . O5 O 0.6785(2) 0.2587(2) 0.46244(9) 0.0624(8) Uani 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 Fe1 0.0364(3) 0.0460(4) 0.0489(3) 0.0051(3) 0.0045(2) -0.0006(3) Fe2 0.0338(3) 0.0337(3) 0.0397(3) 0.0013(2) 0.0020(2) 0.0013(2) S1 0.0429(6) 0.0457(7) 0.0445(5) -0.0005(5) -0.0017(4) -0.0040(5) S2 0.0429(6) 0.0445(6) 0.0493(6) 0.0103(5) -0.0025(5) 0.0020(5) N1 0.072(3) 0.068(3) 0.055(2) 0.000(2) -0.0215(19) -0.003(2) N2 0.0387(18) 0.043(2) 0.0363(16) 0.0012(14) 0.0004(13) -0.0002(15) N3 0.0364(17) 0.051(2) 0.0363(16) -0.0036(15) 0.0006(14) 0.0002(15) N4 0.049(2) 0.062(3) 0.056(2) -0.0014(19) -0.0037(17) 0.003(2) O1 0.073(2) 0.065(2) 0.131(3) 0.016(2) 0.013(2) -0.022(2) O2 0.069(2) 0.095(3) 0.115(3) 0.013(2) -0.014(2) 0.030(2) O3 0.106(3) 0.097(3) 0.062(2) -0.012(2) 0.0267(19) 0.000(2) O4 0.077(2) 0.056(2) 0.082(2) 0.0176(18) -0.0046(17) 0.0228(18) C1 0.043(3) 0.064(3) 0.073(3) 0.010(3) 0.010(2) -0.004(2) C2 0.051(3) 0.062(3) 0.063(3) 0.008(2) 0.001(2) 0.001(2) C3 0.048(3) 0.057(3) 0.066(3) 0.008(2) 0.014(2) 0.000(2) C4 0.040(2) 0.045(3) 0.053(2) -0.001(2) 0.0052(19) 0.003(2) C5 0.041(2) 0.034(2) 0.054(2) 0.003(2) 0.0073(19) 0.0018(18) C6 0.037(2) 0.032(2) 0.0347(18) -0.0035(17) -0.0009(16) 0.0028(17) C7 0.065(3) 0.042(3) 0.063(3) -0.012(2) 0.008(2) -0.006(2) C8 0.060(3) 0.042(3) 0.081(3) -0.008(2) 0.017(2) 0.003(2) C9 0.055(3) 0.036(3) 0.085(3) 0.012(2) 0.003(2) 0.009(2) C10 0.102(4) 0.085(4) 0.065(3) -0.005(3) -0.031(3) -0.019(4) C11 0.115(5) 0.064(4) 0.064(3) -0.017(3) 0.003(3) -0.018(4) C12 0.078(3) 0.051(3) 0.075(3) -0.004(3) 0.019(3) 0.000(3) C13 0.047(3) 0.058(3) 0.054(3) -0.003(2) 0.0065(19) -0.002(2) C14 0.042(2) 0.054(3) 0.035(2) 0.0032(19) 0.0034(17) -0.001(2) C15 0.042(2) 0.057(3) 0.038(2) 0.005(2) -0.0032(17) 0.009(2) C16 0.039(2) 0.062(3) 0.045(2) 0.000(2) 0.0110(18) -0.007(2) C17 0.033(2) 0.066(3) 0.056(2) -0.005(2) 0.0050(19) -0.006(2) C18 0.039(2) 0.062(3) 0.040(2) -0.008(2) -0.0013(17) 0.001(2) C19 0.033(2) 0.066(3) 0.0318(19) -0.003(2) 0.0009(16) 0.003(2) C20 0.044(2) 0.087(4) 0.047(2) -0.009(2) -0.009(2) -0.009(2) C21 0.037(3) 0.135(5) 0.052(3) 0.015(3) -0.012(2) -0.005(3) C22 0.051(3) 0.107(5) 0.058(3) 0.024(3) 0.008(2) 0.019(3) C23 0.070(3) 0.064(3) 0.062(3) 0.001(2) 0.007(3) 0.001(3) O5 0.079(2) 0.057(2) 0.0514(17) -0.0140(16) 0.0108(15) -0.0077(17) #------------------------------------------------------------------------------ _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^)+(0.0411P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5029 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0874 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0902 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.432 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.070 #------------------------------------------------------------------------------ _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 Fe1 C2 1.781(5) . ? Fe1 C3 1.790(5) . ? Fe1 C1 1.798(5) . ? Fe1 S2 2.2532(17) . ? Fe1 S1 2.2640(18) . ? Fe1 Fe2 2.5329(15) . ? Fe2 C5 1.764(4) . ? Fe2 C4 1.765(4) . ? Fe2 C6 1.993(4) . ? Fe2 S2 2.2691(16) . ? Fe2 S1 2.2746(14) . ? S1 C7 1.823(4) . ? S2 C9 1.830(4) . ? N1 C10 1.329(6) . ? N1 C14 1.333(5) . ? N2 C6 1.370(4) . ? N2 C16 1.380(4) . ? N2 C15 1.453(4) . ? N3 C6 1.360(4) . ? N3 C17 1.374(4) . ? N3 C18 1.469(4) . ? N4 C23 1.329(5) . ? N4 C19 1.337(5) . ? O1 C1 1.144(5) . ? O2 C2 1.142(5) . ? O3 C3 1.139(5) . ? O4 C4 1.156(4) . ? C5 O5 1.151(4) . ? C7 C8 1.507(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.504(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.367(7) . ? C10 H10A 0.9300 . ? C11 C12 1.374(7) . ? C11 H11A 0.9300 . ? C12 C13 1.384(6) . ? C12 H12A 0.9300 . ? C13 C14 1.381(5) . ? C13 H13A 0.9300 . ? C14 C15 1.510(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.330(5) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? C18 C19 1.509(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.367(5) . ? C20 C21 1.383(6) . ? C20 H20A 0.9300 . ? C21 C22 1.363(7) . ? C21 H21A 0.9300 . ? C22 C23 1.368(6) . ? C22 H22A 0.9300 . ? C23 H23A 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 C2 Fe1 C3 89.66(19) . . ? C2 Fe1 C1 102.4(2) . . ? C3 Fe1 C1 103.4(2) . . ? C2 Fe1 S2 159.82(15) . . ? C3 Fe1 S2 88.63(14) . . ? C1 Fe1 S2 97.55(15) . . ? C2 Fe1 S1 88.06(14) . . ? C3 Fe1 S1 155.62(14) . . ? C1 Fe1 S1 100.81(14) . . ? S2 Fe1 S1 85.26(5) . . ? C2 Fe1 Fe2 104.51(15) . . ? C3 Fe1 Fe2 101.08(14) . . ? C1 Fe1 Fe2 143.43(14) . . ? S2 Fe1 Fe2 56.24(5) . . ? S1 Fe1 Fe2 56.28(3) . . ? C5 Fe2 C4 92.87(18) . . ? C5 Fe2 C6 99.18(15) . . ? C4 Fe2 C6 98.99(16) . . ? C5 Fe2 S2 85.26(13) . . ? C4 Fe2 S2 156.18(12) . . ? C6 Fe2 S2 104.75(11) . . ? C5 Fe2 S1 153.36(12) . . ? C4 Fe2 S1 86.61(14) . . ? C6 Fe2 S1 107.22(11) . . ? S2 Fe2 S1 84.65(6) . . ? C5 Fe2 Fe1 98.37(12) . . ? C4 Fe2 Fe1 101.41(13) . . ? C6 Fe2 Fe1 152.25(11) . . ? S2 Fe2 Fe1 55.64(4) . . ? S1 Fe2 Fe1 55.88(5) . . ? C7 S1 Fe1 108.91(14) . . ? C7 S1 Fe2 114.80(15) . . ? Fe1 S1 Fe2 67.85(5) . . ? C9 S2 Fe1 111.58(15) . . ? C9 S2 Fe2 113.50(15) . . ? Fe1 S2 Fe2 68.12(4) . . ? C10 N1 C14 116.9(4) . . ? C6 N2 C16 111.6(3) . . ? C6 N2 C15 126.5(3) . . ? C16 N2 C15 121.6(3) . . ? C6 N3 C17 112.3(3) . . ? C6 N3 C18 126.4(3) . . ? C17 N3 C18 121.2(3) . . ? C23 N4 C19 117.0(4) . . ? O1 C1 Fe1 176.0(4) . . ? O2 C2 Fe1 178.8(4) . . ? O3 C3 Fe1 176.9(4) . . ? O4 C4 Fe2 176.9(4) . . ? O5 C5 Fe2 175.9(3) . . ? N3 C6 N2 102.4(3) . . ? N3 C6 Fe2 128.6(2) . . ? N2 C6 Fe2 128.6(2) . . ? C8 C7 S1 115.0(3) . . ? C8 C7 H7A 108.5 . . ? S1 C7 H7A 108.5 . . ? C8 C7 H7B 108.5 . . ? S1 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C9 C8 C7 114.6(3) . . ? C9 C8 H8A 108.6 . . ? C7 C8 H8A 108.6 . . ? C9 C8 H8B 108.6 . . ? C7 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? C8 C9 S2 116.0(3) . . ? C8 C9 H9A 108.3 . . ? S2 C9 H9A 108.3 . . ? C8 C9 H9B 108.3 . . ? S2 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? N1 C10 C11 124.8(5) . . ? N1 C10 H10A 117.6 . . ? C11 C10 H10A 117.6 . . ? C10 C11 C12 118.0(5) . . ? C10 C11 H11A 121.0 . . ? C12 C11 H11A 121.0 . . ? C11 C12 C13 118.7(5) . . ? C11 C12 H12A 120.6 . . ? C13 C12 H12A 120.6 . . ? C14 C13 C12 118.9(4) . . ? C14 C13 H13A 120.6 . . ? C12 C13 H13A 120.6 . . ? N1 C14 C13 122.8(4) . . ? N1 C14 C15 112.6(4) . . ? C13 C14 C15 124.6(3) . . ? N2 C15 C14 114.5(3) . . ? N2 C15 H15A 108.6 . . ? C14 C15 H15A 108.6 . . ? N2 C15 H15B 108.6 . . ? C14 C15 H15B 108.6 . . ? H15A C15 H15B 107.6 . . ? C17 C16 N2 106.9(3) . . ? C17 C16 H16A 126.6 . . ? N2 C16 H16A 126.6 . . ? C16 C17 N3 106.8(3) . . ? C16 C17 H17A 126.6 . . ? N3 C17 H17A 126.6 . . ? N3 C18 C19 112.1(3) . . ? N3 C18 H18A 109.2 . . ? C19 C18 H18A 109.2 . . ? N3 C18 H18B 109.2 . . ? C19 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? N4 C19 C20 122.8(4) . . ? N4 C19 C18 115.9(3) . . ? C20 C19 C18 121.2(4) . . ? C19 C20 C21 118.6(5) . . ? C19 C20 H20A 120.7 . . ? C21 C20 H20A 120.7 . . ? C22 C21 C20 119.5(4) . . ? C22 C21 H21A 120.3 . . ? C20 C21 H21A 120.3 . . ? C21 C22 C23 117.8(5) . . ? C21 C22 H22A 121.1 . . ? C23 C22 H22A 121.1 . . ? N4 C23 C22 124.3(5) . . ? N4 C23 H23A 117.9 . . ? C22 C23 H23A 117.9 . . ? #===END # Copyright The Royal Society of Chemistry, 2006 # CCDC Number: 625997 data_Py580 _database_code_depnum_ccdc_archive 'CCDC 625997' #------------------------------------------------------------------------------ _audit_creation_date 'Oct 31 18:25:00 2006' _audit_creation_method SHELXL-97 _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SMART (Bruker, 1997)' _computing_data_reduction 'SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXP97 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (Bruker, 1997)' #------------------------------------------------------------------------------ _chemical_compound_source ? _chemical_name_common ? _chemical_formula_weight 580.24 _chemical_formula_analytical ? _chemical_formula_sum 'C22 H20 Fe2 N4 O4 S2' _chemical_formula_moiety 'C22 H20 Fe2 N4 O4 S2' _chemical_formula_structural ? _chemical_melting_point ? #------------------------------------------------------------------------------ _cell_length_a 9.285(4) _cell_length_b 10.784(4) _cell_length_c 12.913(5) _cell_angle_alpha 105.748(5) _cell_angle_beta 97.211(4) _cell_angle_gamma 103.396(5) _cell_volume 1185.8(8) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 2371 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 17.80 #------------------------------------------------------------------------------ _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.625 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 1.437 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5336 _exptl_absorpt_correction_T_max 0.9316 _exptl_absorpt_process_details SADABS #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 273(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 6370 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4548 _reflns_number_gt 3570 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.971 #------------------------------------------------------------------------------ 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #------------------------------------------------------------------------------ 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 Fe1 Fe 0.77936(5) 0.99646(5) 0.37030(4) 0.03098(14) Uani 1 1 d . . . Fe2 Fe 0.60925(5) 0.86429(4) 0.18161(3) 0.02814(13) Uani 1 1 d . . . S1 S 0.72202(9) 1.08668(8) 0.23487(7) 0.03321(19) Uani 1 1 d . . . S2 S 0.52543(9) 0.90563(8) 0.33711(7) 0.0339(2) Uani 1 1 d . . . N1 N 0.7529(3) 0.8400(3) 0.0758(2) 0.0349(6) Uani 1 1 d . . . N2 N 0.6890(3) 0.6146(3) 0.1557(2) 0.0382(7) Uani 1 1 d . . . N3 N 0.4550(3) 0.5754(3) 0.1645(2) 0.0391(7) Uani 1 1 d . . . N4 N 0.0877(4) 0.4957(3) 0.2390(3) 0.0545(8) Uani 1 1 d . . . O1 O 0.8604(4) 1.2122(3) 0.5813(2) 0.0712(9) Uani 1 1 d . . . O2 O 1.0734(3) 1.0324(4) 0.3074(2) 0.0693(9) Uani 1 1 d . . . O3 O 0.7863(3) 0.7614(3) 0.4388(3) 0.0661(8) Uani 1 1 d . . . O4 O 0.3354(3) 0.8225(3) 0.0265(2) 0.0616(8) Uani 1 1 d . . . C1 C 0.8246(4) 1.1307(4) 0.4985(3) 0.0415(8) Uani 1 1 d . . . C2 C 0.9589(4) 1.0181(4) 0.3347(3) 0.0415(8) Uani 1 1 d . . . C3 C 0.7872(4) 0.8553(4) 0.4134(3) 0.0410(8) Uani 1 1 d . . . C4 C 0.4477(4) 0.8390(3) 0.0865(3) 0.0363(7) Uani 1 1 d . . . C6 C 0.5911(5) 1.1879(4) 0.2693(3) 0.0528(10) Uani 1 1 d U . . H6A H 0.6484 1.2816 0.2920 0.063 Uiso 1 1 calc R . . H6B H 0.5188 1.1715 0.2026 0.063 Uiso 1 1 calc R . . C7 C 0.5058(6) 1.1676(5) 0.3545(5) 0.0815(15) Uani 1 1 d U . . H7A H 0.5762 1.2082 0.4246 0.098 Uiso 1 1 calc R . . H7B H 0.4327 1.2189 0.3549 0.098 Uiso 1 1 calc R . . C8 C 0.4251(4) 1.0341(4) 0.3515(3) 0.0522(10) Uani 1 1 d . . . H8A H 0.3386 1.0014 0.2911 0.063 Uiso 1 1 calc R . . H8B H 0.3862 1.0422 0.4186 0.063 Uiso 1 1 calc R . . C9 C 0.7527(4) 0.9022(3) -0.0016(3) 0.0398(8) Uani 1 1 d . . . H9A H 0.6892 0.9574 -0.0021 0.048 Uiso 1 1 calc R . . C10 C 0.8400(5) 0.8894(4) -0.0797(3) 0.0530(10) Uani 1 1 d . . . H10A H 0.8338 0.9335 -0.1320 0.064 Uiso 1 1 calc R . . C11 C 0.9367(5) 0.8107(4) -0.0796(3) 0.0582(11) Uani 1 1 d . . . H11A H 0.9986 0.8014 -0.1309 0.070 Uiso 1 1 calc R . . C12 C 0.9395(4) 0.7460(4) -0.0018(3) 0.0516(10) Uani 1 1 d . . . H12A H 1.0040 0.6919 0.0000 0.062 Uiso 1 1 calc R . . C13 C 0.8466(4) 0.7607(3) 0.0743(3) 0.0387(8) Uani 1 1 d . . . C14 C 0.8434(4) 0.6867(4) 0.1579(3) 0.0441(9) Uani 1 1 d . . . H14A H 0.9034 0.6237 0.1424 0.053 Uiso 1 1 calc R . . H14B H 0.8876 0.7500 0.2305 0.053 Uiso 1 1 calc R . . C5 C 0.5784(4) 0.6769(3) 0.1710(3) 0.0328(7) Uani 1 1 d . . . C15 C 0.6344(5) 0.4777(4) 0.1369(3) 0.0502(10) Uani 1 1 d . . . H15A H 0.6889 0.4148 0.1233 0.060 Uiso 1 1 calc R . . C16 C 0.4892(5) 0.4538(4) 0.1422(3) 0.0512(10) Uani 1 1 d . . . H16A H 0.4227 0.3707 0.1327 0.061 Uiso 1 1 calc R . . C17 C 0.3037(4) 0.5892(4) 0.1734(3) 0.0454(9) Uani 1 1 d . . . H17A H 0.2367 0.5438 0.1023 0.054 Uiso 1 1 calc R . . H17B H 0.3078 0.6835 0.1923 0.054 Uiso 1 1 calc R . . C18 C 0.2380(4) 0.5327(3) 0.2579(3) 0.0439(8) Uani 1 1 d . . . C19 C 0.3267(5) 0.5235(5) 0.3477(4) 0.0660(12) Uani 1 1 d . . . H19A H 0.4315 0.5536 0.3594 0.079 Uiso 1 1 calc R . . C20 C 0.2578(7) 0.4689(6) 0.4203(4) 0.0819(15) Uani 1 1 d . . . H20A H 0.3149 0.4609 0.4814 0.098 Uiso 1 1 calc R . . C21 C 0.1029(7) 0.4268(5) 0.3998(5) 0.0811(16) Uani 1 1 d . . . H21A H 0.0530 0.3871 0.4457 0.097 Uiso 1 1 calc R . . C22 C 0.0234(6) 0.4439(5) 0.3115(5) 0.0737(14) Uani 1 1 d . . . H22A H -0.0815 0.4183 0.3004 0.088 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 Fe1 0.0293(3) 0.0348(3) 0.0296(2) 0.0110(2) 0.00663(19) 0.0090(2) Fe2 0.0297(3) 0.0271(2) 0.0292(2) 0.01058(19) 0.00712(18) 0.00820(19) S1 0.0363(5) 0.0299(4) 0.0362(4) 0.0139(4) 0.0104(3) 0.0086(3) S2 0.0310(4) 0.0394(5) 0.0355(4) 0.0155(4) 0.0121(3) 0.0104(4) N1 0.0365(16) 0.0325(15) 0.0332(14) 0.0069(12) 0.0090(12) 0.0080(12) N2 0.0453(17) 0.0326(15) 0.0405(16) 0.0122(13) 0.0110(13) 0.0158(13) N3 0.0449(17) 0.0278(15) 0.0434(16) 0.0135(13) 0.0086(13) 0.0049(13) N4 0.049(2) 0.0431(19) 0.064(2) 0.0084(16) 0.0196(17) 0.0050(16) O1 0.078(2) 0.063(2) 0.0506(18) -0.0110(16) 0.0025(15) 0.0166(17) O2 0.0405(16) 0.116(3) 0.0702(19) 0.0475(19) 0.0239(14) 0.0276(17) O3 0.073(2) 0.0576(19) 0.079(2) 0.0391(17) 0.0087(16) 0.0203(16) O4 0.0527(17) 0.0577(18) 0.0694(19) 0.0228(15) -0.0131(14) 0.0156(14) C1 0.039(2) 0.041(2) 0.043(2) 0.0110(18) 0.0070(16) 0.0103(17) C2 0.040(2) 0.051(2) 0.0389(19) 0.0188(17) 0.0086(16) 0.0152(17) C3 0.041(2) 0.045(2) 0.0393(19) 0.0155(17) 0.0070(15) 0.0129(17) C4 0.045(2) 0.0288(18) 0.0386(18) 0.0132(15) 0.0087(16) 0.0130(15) C6 0.062(3) 0.040(2) 0.070(3) 0.0244(19) 0.022(2) 0.0277(19) C7 0.078(3) 0.062(3) 0.130(4) 0.036(3) 0.051(3) 0.043(3) C8 0.049(2) 0.066(3) 0.061(2) 0.027(2) 0.0285(19) 0.034(2) C9 0.047(2) 0.0385(19) 0.0325(18) 0.0124(15) 0.0099(15) 0.0067(16) C10 0.066(3) 0.045(2) 0.038(2) 0.0091(18) 0.0201(19) -0.003(2) C11 0.063(3) 0.048(2) 0.056(2) 0.005(2) 0.037(2) 0.000(2) C12 0.045(2) 0.042(2) 0.062(3) 0.0042(19) 0.0212(19) 0.0097(18) C13 0.0366(19) 0.0336(18) 0.0400(19) 0.0030(15) 0.0108(15) 0.0070(15) C14 0.044(2) 0.044(2) 0.049(2) 0.0118(17) 0.0124(17) 0.0235(18) C5 0.0382(19) 0.0305(17) 0.0292(16) 0.0089(14) 0.0057(14) 0.0095(15) C15 0.070(3) 0.033(2) 0.055(2) 0.0166(18) 0.016(2) 0.0220(19) C16 0.064(3) 0.0248(19) 0.060(2) 0.0127(17) 0.010(2) 0.0062(18) C17 0.039(2) 0.041(2) 0.052(2) 0.0201(18) 0.0029(17) -0.0010(16) C18 0.051(2) 0.0287(18) 0.052(2) 0.0124(16) 0.0123(18) 0.0091(16) C19 0.065(3) 0.075(3) 0.068(3) 0.036(3) 0.017(2) 0.020(2) C20 0.104(4) 0.098(4) 0.079(3) 0.059(3) 0.040(3) 0.047(3) C21 0.112(5) 0.069(3) 0.093(4) 0.045(3) 0.066(4) 0.036(3) C22 0.070(3) 0.060(3) 0.090(4) 0.014(3) 0.043(3) 0.011(2) #------------------------------------------------------------------------------ _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^)+(0.0525P)^2^+0.2718P] 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 4548 _refine_ls_number_parameters 307 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1017 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.134 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.075 #------------------------------------------------------------------------------ _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 Fe1 C2 1.765(4) . ? Fe1 C3 1.770(4) . ? Fe1 C1 1.804(4) . ? Fe1 S2 2.2693(12) . ? Fe1 S1 2.2844(11) . ? Fe1 Fe2 2.5629(9) . ? Fe2 C4 1.732(4) . ? Fe2 C5 1.938(3) . ? Fe2 N1 2.035(3) . ? Fe2 S2 2.2143(11) . ? Fe2 S1 2.2542(12) . ? S1 C6 1.831(4) . ? S2 C8 1.823(4) . ? N1 C9 1.346(4) . ? N1 C13 1.352(4) . ? N2 C5 1.359(4) . ? N2 C15 1.387(4) . ? N2 C14 1.456(4) . ? N3 C5 1.365(4) . ? N3 C16 1.384(4) . ? N3 C17 1.462(5) . ? N4 C18 1.330(5) . ? N4 C22 1.347(6) . ? O1 C1 1.136(4) . ? O2 C2 1.152(4) . ? O3 C3 1.146(4) . ? O4 C4 1.164(4) . ? C6 C7 1.468(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.449(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.368(5) . ? C9 H9A 0.9300 . ? C10 C11 1.371(6) . ? C10 H10A 0.9300 . ? C11 C12 1.371(6) . ? C11 H11A 0.9300 . ? C12 C13 1.388(5) . ? C12 H12A 0.9300 . ? C13 C14 1.505(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.326(6) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 C18 1.513(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.376(6) . ? C19 C20 1.383(6) . ? C19 H19A 0.9300 . ? C20 C21 1.371(7) . ? C20 H20A 0.9300 . ? C21 C22 1.358(7) . ? C21 H21A 0.9300 . ? C22 H22A 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 C2 Fe1 C3 94.48(16) . . ? C2 Fe1 C1 99.97(17) . . ? C3 Fe1 C1 102.80(16) . . ? C2 Fe1 S2 153.91(12) . . ? C3 Fe1 S2 84.20(12) . . ? C1 Fe1 S2 105.74(11) . . ? C2 Fe1 S1 84.81(11) . . ? C3 Fe1 S1 150.32(12) . . ? C1 Fe1 S1 106.55(12) . . ? S2 Fe1 S1 83.75(3) . . ? C2 Fe1 Fe2 100.36(12) . . ? C3 Fe1 Fe2 96.23(12) . . ? C1 Fe1 Fe2 150.83(11) . . ? S2 Fe1 Fe2 54.13(3) . . ? S1 Fe1 Fe2 55.06(3) . . ? C4 Fe2 C5 95.56(14) . . ? C4 Fe2 N1 98.13(14) . . ? C5 Fe2 N1 87.75(12) . . ? C4 Fe2 S2 101.41(11) . . ? C5 Fe2 S2 91.47(9) . . ? N1 Fe2 S2 160.43(8) . . ? C4 Fe2 S1 105.28(11) . . ? C5 Fe2 S1 159.12(10) . . ? N1 Fe2 S1 88.07(8) . . ? S2 Fe2 S1 85.72(3) . . ? C4 Fe2 Fe1 148.82(11) . . ? C5 Fe2 Fe1 105.50(10) . . ? N1 Fe2 Fe1 105.30(8) . . ? S2 Fe2 Fe1 56.15(4) . . ? S1 Fe2 Fe1 56.18(3) . . ? C6 S1 Fe2 113.03(14) . . ? C6 S1 Fe1 111.09(13) . . ? Fe2 S1 Fe1 68.76(3) . . ? C8 S2 Fe2 112.40(13) . . ? C8 S2 Fe1 111.55(14) . . ? Fe2 S2 Fe1 69.71(3) . . ? C9 N1 C13 116.5(3) . . ? C9 N1 Fe2 118.9(2) . . ? C13 N1 Fe2 124.5(2) . . ? C5 N2 C15 111.4(3) . . ? C5 N2 C14 122.4(3) . . ? C15 N2 C14 126.2(3) . . ? C5 N3 C16 111.0(3) . . ? C5 N3 C17 125.5(3) . . ? C16 N3 C17 123.4(3) . . ? C18 N4 C22 116.6(4) . . ? O1 C1 Fe1 175.6(3) . . ? O2 C2 Fe1 177.2(3) . . ? O3 C3 Fe1 177.2(3) . . ? O4 C4 Fe2 176.9(3) . . ? C7 C6 S1 118.0(3) . . ? C7 C6 H6A 107.8 . . ? S1 C6 H6A 107.8 . . ? C7 C6 H6B 107.8 . . ? S1 C6 H6B 107.8 . . ? H6A C6 H6B 107.1 . . ? C8 C7 C6 120.9(4) . . ? C8 C7 H7A 107.1 . . ? C6 C7 H7A 107.1 . . ? C8 C7 H7B 107.1 . . ? C6 C7 H7B 107.1 . . ? H7A C7 H7B 106.8 . . ? C7 C8 S2 118.9(3) . . ? C7 C8 H8A 107.6 . . ? S2 C8 H8A 107.6 . . ? C7 C8 H8B 107.6 . . ? S2 C8 H8B 107.6 . . ? H8A C8 H8B 107.0 . . ? N1 C9 C10 124.1(3) . . ? N1 C9 H9A 117.9 . . ? C10 C9 H9A 117.9 . . ? C9 C10 C11 119.2(4) . . ? C9 C10 H10A 120.4 . . ? C11 C10 H10A 120.4 . . ? C12 C11 C10 118.0(3) . . ? C12 C11 H11A 121.0 . . ? C10 C11 H11A 121.0 . . ? C11 C12 C13 120.4(4) . . ? C11 C12 H12A 119.8 . . ? C13 C12 H12A 119.8 . . ? N1 C13 C12 121.7(3) . . ? N1 C13 C14 116.9(3) . . ? C12 C13 C14 121.4(3) . . ? N2 C14 C13 110.8(3) . . ? N2 C14 H14A 109.5 . . ? C13 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? N2 C5 N3 103.5(3) . . ? N2 C5 Fe2 122.2(2) . . ? N3 C5 Fe2 133.9(2) . . ? C16 C15 N2 106.8(3) . . ? C16 C15 H15A 126.6 . . ? N2 C15 H15A 126.6 . . ? C15 C16 N3 107.3(3) . . ? C15 C16 H16A 126.3 . . ? N3 C16 H16A 126.3 . . ? N3 C17 C18 113.7(3) . . ? N3 C17 H17A 108.8 . . ? C18 C17 H17A 108.8 . . ? N3 C17 H17B 108.8 . . ? C18 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? N4 C18 C19 123.2(4) . . ? N4 C18 C17 114.2(3) . . ? C19 C18 C17 122.6(4) . . ? C18 C19 C20 119.0(5) . . ? C18 C19 H19A 120.5 . . ? C20 C19 H19A 120.5 . . ? C21 C20 C19 118.3(5) . . ? C21 C20 H20A 120.9 . . ? C19 C20 H20A 120.9 . . ? C22 C21 C20 119.1(4) . . ? C22 C21 H21A 120.5 . . ? C20 C21 H21A 120.5 . . ? N4 C22 C21 123.8(5) . . ? N4 C22 H22A 118.1 . . ? C21 C22 H22A 118.1 . . ? #===END