############################################################################## ### ### ### Electronic paper (Acta Crystallographica Section E) ### ### ### ############################################################################## # # # This CIF contains the data in a paper accepted for publication in Acta # # Crystallographica Section E. It conforms to the requirements of Notes # # for Authors for Section E, and has been peer reviewed under the auspices # # of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1. # # # # Software is freely available for graphical display of the structure(s) in # # this CIF. For information consult the CIF home page http://www.iucr.org/ # # cif/home.html # # # ############################################################################## data_global _audit_creation_method 'from SHELXL97 CIF and IUCr SHELXL97-template' _journal_date_recd_electronic 2007-10-16 _journal_date_accepted 2007-10-31 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2008 _journal_volume 64 _journal_issue 1 _journal_page_first m135 _journal_page_last m135 _journal_paper_category QM _journal_coeditor_code BQ2041 _publ_contact_author_name 'Shujiang Tu' _publ_contact_author_address ; College of Chemistry and Chemical Engineering Xuzhou Normal University Xuzhou 221116 People's Republic of China ; _publ_contact_author_email laotu2001@263.net _publ_contact_author_fax 86-516-83403163 _publ_contact_author_phone 86-516-83500349 _publ_section_title ; 2-Amino-4-(4-bromophenyl)-6-ferrocenylpyridine-3-carbonitrile in aqueous medium ; loop_ _publ_author_name _publ_author_address 'Run-Hong Jia' ; Lianyungang Teacher's College Lianyungang 222006 People's Republic of China ; 'Shu-Jiang Tu' ; College of Chemistry and Chemical Engineering Xuzhou Normal University Xuzhou 221116 People's Republic of China ; data_I _chemical_name_systematic ; 2-Amino-4-(4-bromophenyl)-6-ferrocenylpyridine-3-carbonitrile ; _chemical_name_common ? _chemical_formula_moiety 'C22 H16 Br Fe N3' _chemical_formula_sum 'C22 H16 Br Fe N3' _chemical_formula_iupac '[Fe (C5 H5) (C17 H11 Br N3)]' _chemical_formula_weight 458.14 _chemical_melting_point '>573' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 12.250(2) _cell_length_b 7.4511(12) _cell_length_c 20.698(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.729(3) _cell_angle_gamma 90.00 _cell_volume 1872.2(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9276 _cell_measurement_theta_min 1.83 _cell_measurement_theta_max 25.01 _cell_measurement_temperature 298(2) _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 1.625 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 2.951 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1998)' _exptl_absorpt_correction_T_min 0.6496 _exptl_absorpt_correction_T_max 0.8201 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9276 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0466 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 24 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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. ; _reflns_number_total 3290 _reflns_number_gt 2327 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_gt 0.0841 _refine_ls_wR_factor_ref 0.0942 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_number_reflns 3290 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0439P)^2^+0.8730P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.410 _refine_diff_density_min -0.501 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' 'Fe' 'Fe' 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material 'SHELXTL (Bruker, 1999)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Fe Fe1 0.88176(4) 0.56744(7) 0.10748(3) 0.03294(17) Uani d . 1 . . Br Br1 1.31762(4) -0.46355(6) 0.38737(3) 0.06095(19) Uani d . 1 . . N N1 0.8559(2) 0.4500(4) 0.27746(15) 0.0335(7) Uani d . 1 . . N N2 0.8621(3) 0.5510(4) 0.38201(16) 0.0441(9) Uani d . 1 . . H H2A 0.8136 0.6301 0.3678 0.053 Uiso calc R 1 . . H H2B 0.8871 0.5466 0.4228 0.053 Uiso calc R 1 . . N N3 1.0484(3) 0.3011(5) 0.48388(19) 0.0596(11) Uani d . 1 . . C C1 0.8991(3) 0.4337(5) 0.34017(18) 0.0319(9) Uani d . 1 . . C C2 0.9785(3) 0.3014(5) 0.36174(18) 0.0302(8) Uani d . 1 . . C C3 1.0146(3) 0.1847(5) 0.31590(18) 0.0302(9) Uani d . 1 . . C C4 0.9720(3) 0.2070(5) 0.25112(18) 0.0313(9) Uani d . 1 . . H H4 0.9956 0.1339 0.2193 0.038 Uiso calc R 1 . . C C5 0.8928(3) 0.3408(5) 0.23362(17) 0.0274(8) Uani d . 1 . . C C6 0.8419(3) 0.3651(5) 0.16587(17) 0.0295(8) Uani d . 1 . . C C7 0.7494(3) 0.4767(5) 0.14559(18) 0.0328(9) Uani d . 1 . . H H7 0.7103 0.5424 0.1731 0.039 Uiso calc R 1 . . C C8 0.7267(3) 0.4714(5) 0.0769(2) 0.0404(10) Uani d . 1 . . H H8 0.6696 0.5310 0.0514 0.048 Uiso calc R 1 . . C C9 0.8063(3) 0.3594(5) 0.05372(19) 0.0384(9) Uani d . 1 . . H H9 0.8107 0.3334 0.0102 0.046 Uiso calc R 1 . . C C10 0.8781(3) 0.2935(5) 0.10802(18) 0.0343(9) Uani d . 1 . . H H10 0.9379 0.2175 0.1064 0.041 Uiso calc R 1 . . C C11 1.0377(4) 0.6526(6) 0.1005(2) 0.0542(12) Uani d . 1 . . H H11 1.0979 0.5798 0.0960 0.065 Uiso calc R 1 . . C C12 1.0040(4) 0.7097(6) 0.1601(3) 0.0596(13) Uani d . 1 . . H H12 1.0381 0.6819 0.2018 0.072 Uiso calc R 1 . . C C13 0.9095(4) 0.8163(6) 0.1444(3) 0.0597(13) Uani d . 1 . . H H13 0.8697 0.8711 0.1741 0.072 Uiso calc R 1 . . C C14 0.8852(4) 0.8261(6) 0.0762(3) 0.0586(13) Uani d . 1 . . H H14 0.8269 0.8885 0.0530 0.070 Uiso calc R 1 . . C C15 0.9639(4) 0.7257(6) 0.0495(2) 0.0533(12) Uani d . 1 . . H H15 0.9671 0.7098 0.0053 0.064 Uiso calc R 1 . . C C16 1.0201(3) 0.2954(5) 0.4291(2) 0.0395(10) Uani d . 1 . . C C17 1.0911(3) 0.0326(5) 0.33629(17) 0.0306(8) Uani d . 1 . . C C18 1.1829(3) 0.0036(5) 0.3047(2) 0.0439(10) Uani d . 1 . . H H18 1.1986 0.0831 0.2725 0.053 Uiso calc R 1 . . C C19 1.2509(3) -0.1418(6) 0.3206(2) 0.0461(11) Uani d . 1 . . H H19 1.3125 -0.1601 0.2996 0.055 Uiso calc R 1 . . C C20 1.2267(3) -0.2594(5) 0.3678(2) 0.0389(10) Uani d . 1 . . C C21 1.1376(3) -0.2323(5) 0.3997(2) 0.0484(11) Uani d . 1 . . H H21 1.1226 -0.3120 0.4320 0.058 Uiso calc R 1 . . C C22 1.0702(3) -0.0868(5) 0.3841(2) 0.0455(11) Uani d . 1 . . H H22 1.0097 -0.0686 0.4060 0.055 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Fe1 0.0303(3) 0.0277(3) 0.0417(3) -0.0076(2) 0.0078(2) 0.0011(2) Br1 0.0584(3) 0.0489(3) 0.0780(4) 0.0306(2) 0.0181(3) 0.0102(3) N1 0.0335(18) 0.0312(17) 0.0363(18) 0.0084(14) 0.0065(14) -0.0016(15) N2 0.048(2) 0.045(2) 0.0387(19) 0.0278(17) 0.0043(16) -0.0063(16) N3 0.070(3) 0.065(3) 0.041(2) 0.031(2) -0.002(2) -0.005(2) C1 0.028(2) 0.030(2) 0.038(2) 0.0045(16) 0.0073(17) -0.0006(18) C2 0.030(2) 0.0270(19) 0.033(2) 0.0053(16) 0.0019(16) -0.0024(16) C3 0.027(2) 0.0275(19) 0.037(2) -0.0008(16) 0.0081(17) 0.0005(17) C4 0.027(2) 0.0300(19) 0.039(2) 0.0041(16) 0.0100(17) -0.0031(17) C5 0.026(2) 0.0267(19) 0.031(2) -0.0012(15) 0.0091(16) -0.0010(16) C6 0.028(2) 0.0263(18) 0.035(2) -0.0034(16) 0.0058(16) -0.0018(17) C7 0.029(2) 0.035(2) 0.036(2) -0.0065(17) 0.0084(16) -0.0015(17) C8 0.033(2) 0.040(2) 0.048(3) -0.0059(18) 0.0007(18) 0.005(2) C9 0.041(2) 0.041(2) 0.034(2) -0.013(2) 0.0084(18) -0.0028(19) C10 0.037(2) 0.0253(19) 0.042(2) -0.0050(17) 0.0114(18) -0.0030(18) C11 0.036(3) 0.052(3) 0.075(4) -0.018(2) 0.012(2) 0.008(3) C12 0.060(3) 0.052(3) 0.064(3) -0.035(3) -0.005(3) 0.003(2) C13 0.067(4) 0.035(2) 0.080(4) -0.021(2) 0.023(3) -0.012(3) C14 0.055(3) 0.035(2) 0.088(4) -0.006(2) 0.020(3) 0.011(3) C15 0.053(3) 0.050(3) 0.059(3) -0.017(2) 0.020(2) 0.011(2) C16 0.042(3) 0.037(2) 0.039(3) 0.0170(19) 0.006(2) -0.0008(19) C17 0.028(2) 0.0270(19) 0.037(2) 0.0028(16) 0.0087(16) -0.0027(17) C18 0.048(3) 0.038(2) 0.049(3) 0.0091(19) 0.018(2) 0.006(2) C19 0.038(2) 0.047(2) 0.058(3) 0.011(2) 0.024(2) 0.003(2) C20 0.033(2) 0.032(2) 0.052(3) 0.0118(17) 0.0080(19) -0.003(2) C21 0.050(3) 0.039(2) 0.061(3) 0.012(2) 0.023(2) 0.013(2) C22 0.040(2) 0.042(2) 0.059(3) 0.012(2) 0.024(2) 0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Fe1 C7 . 2.013(4) ? Fe1 C13 . 2.017(4) ? Fe1 C12 . 2.028(4) ? Fe1 C6 . 2.033(4) ? Fe1 C14 . 2.035(4) ? Fe1 C11 . 2.037(4) ? Fe1 C15 . 2.041(4) ? Fe1 C10 . 2.042(4) ? Fe1 C8 . 2.049(4) ? Fe1 C9 . 2.054(4) ? Br1 C20 . 1.897(4) ? N1 C1 . 1.340(5) ? N1 C5 . 1.342(4) ? N2 C1 . 1.351(4) ? N2 H2A . 0.8600 ? N2 H2B . 0.8600 ? N3 C16 . 1.140(5) ? C1 C2 . 1.415(5) ? C2 C3 . 1.402(5) ? C2 C16 . 1.420(6) ? C3 C4 . 1.382(5) ? C3 C17 . 1.495(5) ? C4 C5 . 1.404(5) ? C4 H4 . 0.9300 ? C5 C6 . 1.468(5) ? C6 C7 . 1.423(5) ? C6 C10 . 1.435(5) ? C7 C8 . 1.412(5) ? C7 H7 . 0.9300 ? C8 C9 . 1.416(5) ? C8 H8 . 0.9300 ? C9 C10 . 1.419(5) ? C9 H9 . 0.9300 ? C10 H10 . 0.9300 ? C11 C15 . 1.404(6) ? C11 C12 . 1.417(6) ? C11 H11 . 0.9300 ? C12 C13 . 1.406(6) ? C12 H12 . 0.9300 ? C13 C14 . 1.404(7) ? C13 H13 . 0.9300 ? C14 C15 . 1.392(6) ? C14 H14 . 0.9300 ? C15 H15 . 0.9300 ? C17 C22 . 1.380(5) ? C17 C18 . 1.392(5) ? C18 C19 . 1.379(5) ? C18 H18 . 0.9300 ? C19 C20 . 1.374(5) ? C19 H19 . 0.9300 ? C20 C21 . 1.365(5) ? C21 C22 . 1.375(5) ? C21 H21 . 0.9300 ? C22 H22 . 0.9300 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C7 Fe1 C13 . . 105.30(18) ? C7 Fe1 C12 . . 122.73(18) ? C13 Fe1 C12 . . 40.67(19) ? C7 Fe1 C6 . . 41.17(14) ? C13 Fe1 C6 . . 119.91(18) ? C12 Fe1 C6 . . 106.72(17) ? C7 Fe1 C14 . . 119.64(17) ? C13 Fe1 C14 . . 40.54(18) ? C12 Fe1 C14 . . 68.3(2) ? C6 Fe1 C14 . . 155.28(18) ? C7 Fe1 C11 . . 160.93(17) ? C13 Fe1 C11 . . 68.2(2) ? C12 Fe1 C11 . . 40.81(18) ? C6 Fe1 C11 . . 125.17(17) ? C14 Fe1 C11 . . 67.84(19) ? C7 Fe1 C15 . . 155.64(17) ? C13 Fe1 C15 . . 67.7(2) ? C12 Fe1 C15 . . 68.07(19) ? C6 Fe1 C15 . . 162.71(17) ? C14 Fe1 C15 . . 39.94(17) ? C11 Fe1 C15 . . 40.27(17) ? C7 Fe1 C10 . . 69.07(15) ? C13 Fe1 C10 . . 156.9(2) ? C12 Fe1 C10 . . 122.33(18) ? C6 Fe1 C10 . . 41.23(14) ? C14 Fe1 C10 . . 161.78(19) ? C11 Fe1 C10 . . 109.48(18) ? C15 Fe1 C10 . . 126.43(17) ? C7 Fe1 C8 . . 40.67(15) ? C13 Fe1 C8 . . 122.68(19) ? C12 Fe1 C8 . . 159.3(2) ? C6 Fe1 C8 . . 68.75(15) ? C14 Fe1 C8 . . 106.87(18) ? C11 Fe1 C8 . . 157.92(18) ? C15 Fe1 C8 . . 122.02(18) ? C10 Fe1 C8 . . 68.44(16) ? C7 Fe1 C9 . . 68.36(15) ? C13 Fe1 C9 . . 160.0(2) ? C12 Fe1 C9 . . 158.7(2) ? C6 Fe1 C9 . . 68.62(15) ? C14 Fe1 C9 . . 124.71(19) ? C11 Fe1 C9 . . 123.72(18) ? C15 Fe1 C9 . . 109.84(17) ? C10 Fe1 C9 . . 40.53(14) ? C8 Fe1 C9 . . 40.36(15) ? C1 N1 C5 . . 118.3(3) ? C1 N2 H2A . . 120.0 ? C1 N2 H2B . . 120.0 ? H2A N2 H2B . . 120.0 ? N1 C1 N2 . . 116.1(3) ? N1 C1 C2 . . 122.3(3) ? N2 C1 C2 . . 121.6(3) ? C3 C2 C1 . . 119.0(3) ? C3 C2 C16 . . 122.8(3) ? C1 C2 C16 . . 118.2(3) ? C4 C3 C2 . . 118.0(3) ? C4 C3 C17 . . 120.4(3) ? C2 C3 C17 . . 121.5(3) ? C3 C4 C5 . . 119.6(3) ? C3 C4 H4 . . 120.2 ? C5 C4 H4 . . 120.2 ? N1 C5 C4 . . 122.7(3) ? N1 C5 C6 . . 115.6(3) ? C4 C5 C6 . . 121.6(3) ? C7 C6 C10 . . 107.1(3) ? C7 C6 C5 . . 125.0(3) ? C10 C6 C5 . . 127.7(3) ? C7 C6 Fe1 . . 68.7(2) ? C10 C6 Fe1 . . 69.7(2) ? C5 C6 Fe1 . . 123.7(2) ? C8 C7 C6 . . 108.8(3) ? C8 C7 Fe1 . . 71.0(2) ? C6 C7 Fe1 . . 70.1(2) ? C8 C7 H7 . . 125.6 ? C6 C7 H7 . . 125.6 ? Fe1 C7 H7 . . 124.8 ? C7 C8 C9 . . 107.8(3) ? C7 C8 Fe1 . . 68.3(2) ? C9 C8 Fe1 . . 70.0(2) ? C7 C8 H8 . . 126.1 ? C9 C8 H8 . . 126.1 ? Fe1 C8 H8 . . 127.2 ? C8 C9 C10 . . 108.5(3) ? C8 C9 Fe1 . . 69.6(2) ? C10 C9 Fe1 . . 69.3(2) ? C8 C9 H9 . . 125.7 ? C10 C9 H9 . . 125.7 ? Fe1 C9 H9 . . 127.0 ? C9 C10 C6 . . 107.7(3) ? C9 C10 Fe1 . . 70.2(2) ? C6 C10 Fe1 . . 69.1(2) ? C9 C10 H10 . . 126.1 ? C6 C10 H10 . . 126.1 ? Fe1 C10 H10 . . 126.2 ? C15 C11 C12 . . 107.7(5) ? C15 C11 Fe1 . . 70.1(2) ? C12 C11 Fe1 . . 69.3(2) ? C15 C11 H11 . . 126.2 ? C12 C11 H11 . . 126.2 ? Fe1 C11 H11 . . 126.1 ? C13 C12 C11 . . 107.2(4) ? C13 C12 Fe1 . . 69.2(2) ? C11 C12 Fe1 . . 69.9(2) ? C13 C12 H12 . . 126.4 ? C11 C12 H12 . . 126.4 ? Fe1 C12 H12 . . 126.0 ? C14 C13 C12 . . 108.6(5) ? C14 C13 Fe1 . . 70.4(3) ? C12 C13 Fe1 . . 70.1(2) ? C14 C13 H13 . . 125.7 ? C12 C13 H13 . . 125.7 ? Fe1 C13 H13 . . 125.3 ? C15 C14 C13 . . 107.8(5) ? C15 C14 Fe1 . . 70.3(2) ? C13 C14 Fe1 . . 69.0(3) ? C15 C14 H14 . . 126.1 ? C13 C14 H14 . . 126.1 ? Fe1 C14 H14 . . 126.2 ? C14 C15 C11 . . 108.7(4) ? C14 C15 Fe1 . . 69.8(2) ? C11 C15 Fe1 . . 69.7(2) ? C14 C15 H15 . . 125.6 ? C11 C15 H15 . . 125.6 ? Fe1 C15 H15 . . 126.5 ? N3 C16 C2 . . 174.9(4) ? C22 C17 C18 . . 118.5(3) ? C22 C17 C3 . . 121.4(3) ? C18 C17 C3 . . 120.0(3) ? C19 C18 C17 . . 120.7(4) ? C19 C18 H18 . . 119.7 ? C17 C18 H18 . . 119.7 ? C20 C19 C18 . . 119.3(4) ? C20 C19 H19 . . 120.4 ? C18 C19 H19 . . 120.4 ? C21 C20 C19 . . 120.9(4) ? C21 C20 Br1 . . 120.0(3) ? C19 C20 Br1 . . 119.1(3) ? C20 C21 C22 . . 119.8(4) ? C20 C21 H21 . . 120.1 ? C22 C21 H21 . . 120.1 ? C21 C22 C17 . . 120.9(4) ? C21 C22 H22 . . 119.5 ? C17 C22 H22 . . 119.5 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H2B N3 3_766 0.86 2.29 3.050(5) 148.0