metal-organic compounds Acta Crystallographica Section E  = 1.26 mm T = 298 K Structure Reports Online 1 0.45  0.43  0.31 mm Data collection ISSN 1600-5368 (2,20 -Biquinoline-j2N,N0 )dichloridoiron(II) Narjes Rahimi, Nasser Safari,* Vahid Amani and Hamid Reza Khavasi Department of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran Correspondence e-mail: n-safari@cc.sbu.ac.ir Stoe IPDS II diffractometer Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005) Tmin = 0.577, Tmax = 0.681 13058 measured reflections 4323 independent reflections 3739 reflections with I > 2(I) Rint = 0.024 Refinement R[F 2 > 2(F 2)] = 0.037 wR(F 2) = 0.093 S = 1.06 4323 reflections 208 parameters H-atom parameters constrained
max = 0.52 e Å 3
min = 0.44 e Å 3 Table 1 Selected geometric parameters (Å,  ). Received 8 October 2009; accepted 10 October 2009 Key indicators: single-crystal X-ray study; T = 298 K; mean (C–C) = 0.003 Å; R factor = 0.037; wR factor = 0.093; data-to-parameter ratio = 20.8. Fe1—N1 Fe1—N2 N2—Fe1—N1 2.1051 (14) 2.1008 (15) Fe1—Cl2 Fe1—Cl1 2.2265 (6) 2.2341 (7) 78.06 (6) In the title compound, [FeCl2(C18H12N2)], the FeII atom is four-coordinated in a distorted tetrahedral arrangement by an N,N0 -bidentate 2,20 -biquinoline ligand and two chloride ions. In the crystal, there are extensive – contacts between the pyridine rings [centroid–centroid distances = 3.7611 (3), 3.7603 (4), 3.5292 (4), 3.5336 (5) and 3.6656 (4) Å]. Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: XAREA; data reduction: X-RED (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97. Related literature We are grateful to the Shahid Beheshti University for financial support. For related structures, see: Amani et al. (2009); Amani, Safari & Khavasi (2007); Amani, Safari, Khavasi & Mirzaei (2007); Chan & Baird (2004); Gibson et al. (2002); Handley et al. (2001); Khavasi et al. (2007, 2008). For bond-length data, see: Figgis et al. (1983); Kulkarni et al. (1998). Experimental Crystal data [FeCl2(C18H12N2)] Mr = 383.05 Monoclinic, P21 =n a = 7.9777 (6) Å b = 12.2268 (11) Å m1370 Rahimi et al. c = 16.9904 (12) Å = 102.899 (6) V = 1615.5 (2) Å3 Z=4 Mo K radiation Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5133). References Amani, V., Safari, N. & Khavasi, H. R. (2007). Polyhedron, 26, 4257–4262. Amani, V., Safari, N., Khavasi, H. R. & Mirzaei, P. (2007). Polyhedron, 26, 4908–4914. Amani, V., Safari, N., Notash, B. & Khavasi, H. R. (2009). J. Coord. Chem. 62, 1939–1950. Chan, B. C. K. & Baird, M. C. (2004). Inorg. Chim. Acta, 357, 2776–2782. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Figgis, B. N., Patrick, J. M., Reynolds, P. A., Skelton, B. W., White, A. H. & Healy, P. C. (1983). Aust. J. Chem. 36, 2043–2055. Gibson, V. C., Reilly, R. K., Reed, W., Wass, D. F., White, A. J. P. & Williams, D. J. (2002). Chem. Commun. pp. 1850–1851. Handley, D. A., Hitchcock, P. B., Lee, T. H. & Leigh, G. J. (2001). Inorg. Chim. Acta, 314, 14–21. Khavasi, H. R., Amani, V. & Safari, N. (2007). Z. Kristallogr. New Cryst. Struct. 222, 155–156. Khavasi, H. R., Amani, V. & Safari, N. (2008). Z. Kristallogr. New Cryst. Struct. 223, 41–42. Kulkarni, P., Padhye, S. & Sinn, E. (1998). Polyhedron, 17, 2623–2626. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Stoe & Cie (2005). X-AREA, X-SHAPE and X-RED. Stoe & Cie, Darmstadt, Germany. doi:10.1107/S1600536809041439 Acta Cryst. (2009). E65, m1370 supporting information supporting information Acta Cryst. (2009). E65, m1370 [https://doi.org/10.1107/S1600536809041439] (2,2′-Biquinoline-κ2N,N′)dichloridoiron(II) Narjes Rahimi, Nasser Safari, Vahid Amani and Hamid Reza Khavasi S1. Comment Recently, we reported the synthes and crystal structure of iron (III) hetero-ligand complexes such as [Fe(bipy)Cl4] [bipy.H], (II), [Fe(5,5′-dmbpy)2Cl2][FeCl4], (III), (Amani, Safari & Khavasi 2007), [Fe(phen)Cl3(CH3OH)].CH3OH, (IV), (Khavasi et al., 2007), [Fe(bipy)Cl3(DMSO)], (V) and [Fe(phen)Cl3(DMSO)], (VI), (Amani, Safari, khavasi & Mirzaei, 2007), [Fe(phen)Cl4][phen.H], (VII), (Khavasi et al., 2008), [Fe(4,4′-dmbpy)Cl4][4,4′-dmbpy.H], (VIII) and [Fe(4,4′dmbpy)Cl3(DMSO)], (IX), (Amani et al., 2009) [where bipy is 2,2′-bipyridine, 5,5′-dmbpy is 5,5′-dimethyl-2,2′-bipyridine, phen is 1,10-phenanthroline, DMSO is dimethyl sulfoxide and 4,4′-dmbpy is 4,4′-dimethyl-2,2′-bipyridine]. There are several FeII complexes, with formula, [FeCl2(N—N)], such as [FeCl2(6,6′-dmbpy)], (X), (Chan & Baird 2004), [FeCl2(BDP)], (XI), (Handley et al., 2001) and [FeCl2(DEI)], (XII), (Gibson et al., 2002) [where 6,6′-dmbpy is 6, 6′-dimethyl-2, 2′-bipyridine, BDP is 1,3-bis(dimethylamino) propane and DEI is N,N′-dicyclohexyl-1,2-ethanedi-imine] have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound (I). In the molecule of the title compound, (I), (Fig. 1), the FeII atom is four-coordinated in distorted tetrahedral configurations by two N atoms from one 2, 2′-biquinoline and two terminal Cl atoms. The Fe—Cl and Fe—N bond lengths and angles (Table 1) are within normal range (X). In this complex, Fe—N average distance is 2.1029 (15)Å and the Fe—Cl average bond distance is 2.2303 (6) Å. The Fe—N average bond distances in high-spin FeII and FeIII phenanthroline and bipyridine complexes are around 2.2 Å. However, low-spin FeII and FeIII complexes, the Fe—N distances less than 2 Å were reported (Figgis et al., 1983; Kulkarni et al., 1998). Therefore, in the molecule of the title compound, the Fe—N bond distance is unambiguously high-spin FeII. It seems substitution in the 6 position of bipyridine is crucial to stabilize FeII high-spin versus (FeII) especially low-spin. Also, biquinoline result in auto reduce of FeIII to FeII. The π-π contacts between the pyridine rings, Cg2···Cg2i, Cg2···Cg4i, Cg3···Cg3ii, Cg3···Cg5i, Cg4···Cg4ii and Cg5···Cg3ii [symmetry cods: (i) 1-X, 1-Y, 1-Z, (ii) 1-X,-Y,1-Z, where Cg2, Cg3, Cg4 and Cg5 are centroids of the rings (N1/C1/C6— C9), (N2/C10—C13/C18), (C1—C6) and (C13—C18), respectively] further stabilize the structure, with centroid-centroid distance of 3.7611 (3), 3.7603 (4), 3.5292 (4), 3.5336 (5) and 3.6656 (4) Å, respectively. It seems this π-π stacking is effective in the stabilization of the crystal structure (Fig. 2). S2. Experimental A solution of 2,2′-biquinoline (0.20 g, 0.78 mmol) in methanol (6 ml) and chloroform (2 ml) was added to a solution of FeCl3.6H2O (0.07 g, 0.26 mmol) in methanol (6 ml) and chloroform (2 ml) and the resulting yellow solution was stirred for 15 min at room temperature. This solution was left to evaporate slowly at room temperature. After two weeks, red blocks of (I) were isolated (yield 0.07 g, 70.3%). Acta Cryst. (2009). E65, m1370 sup-1 supporting information S3. Refinement All H atoms were positioned geometrically (C—H = 0.93Å) and refined as riding with Uiso(H)=1.2Ueq. Figure 1 The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. Figure 2 Unit-cell packing diagram for (I). (2,2′-Biquinoline-κ2N,N′)dichloridoiron(II) Crystal data [FeCl2(C18H12N2)] Mr = 383.05 Acta Cryst. (2009). E65, m1370 Monoclinic, P21/n Hall symbol: -P 2yn sup-2 supporting information Mo Kα radiation, λ = 0.71073 Å Cell parameters from 1323 reflections θ = 2.1–29.3° µ = 1.26 mm−1 T = 298 K Block, red 0.45 × 0.43 × 0.31 mm a = 7.9777 (6) Å b = 12.2268 (11) Å c = 16.9904 (12) Å β = 102.899 (6)° V = 1615.5 (2) Å3 Z=4 F(000) = 776 Dx = 1.575 Mg m−3 Data collection Stoe IPDS II diffractometer Radiation source: fine-focus sealed tube Graphite monochromator Detector resolution: 0.15 mm pixels mm-1 rotation method scans Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005) Tmin = 0.577, Tmax = 0.681 13058 measured reflections 4323 independent reflections 3739 reflections with I > 2σ(I) Rint = 0.024 θmax = 29.3°, θmin = 2.1° h = −10→10 k = −16→16 l = −23→21 Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.037 wR(F2) = 0.093 S = 1.06 4323 reflections 208 parameters 0 restraints Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ2(Fo2) + (0.0407P)2 + 0.7232P] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max = 0.007 Δρmax = 0.52 e Å−3 Δρmin = −0.44 e Å−3 Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) C1 C2 H2 C3 H3 C4 H4 C5 x y z Uiso*/Ueq 0.2274 (2) 0.3108 (3) 0.3097 0.3929 (3) 0.4477 0.3959 (3) 0.4536 0.3157 (3) 0.95885 (14) 1.01753 (16) 0.9909 1.11314 (18) 1.1515 1.15461 (17) 1.2196 1.10094 (17) 0.02892 (11) 0.09821 (13) 0.1494 0.09004 (15) 0.1359 0.01308 (17) 0.0086 −0.05409 (15) 0.0367 (3) 0.0462 (4) 0.055* 0.0546 (5) 0.066* 0.0571 (6) 0.069* 0.0520 (5) Acta Cryst. (2009). E65, m1370 sup-3 supporting information H5 C6 C7 H7 C8 H8 C9 C10 C11 H11 C12 H12 C13 C14 H14 C15 H15 C16 H16 C17 H17 C18 N1 N2 Fe1 Cl1 Cl2 0.3174 0.2289 (2) 0.1447 (3) 0.1447 0.0630 (3) 0.0069 0.0647 (2) −0.0289 (2) −0.1412 (3) −0.1539 −0.2310 (2) −0.3060 −0.2108 (2) −0.2993 (3) −0.3764 −0.2720 (3) −0.3316 −0.1546 (4) −0.1362 −0.0666 (3) 0.0105 −0.0937 (2) 0.14684 (19) −0.00420 (19) 0.17508 (4) 0.43989 (8) 0.05960 (9) 1.1297 1.00112 (15) 0.94060 (17) 0.9656 0.84538 (16) 0.8052 0.80865 (14) 0.70846 (13) 0.65279 (15) 0.6755 0.56528 (16) 0.5280 0.53109 (15) 0.44022 (17) 0.4011 0.4098 (2) 0.3506 0.4673 (2) 0.4450 0.55570 (18) 0.5933 0.58938 (15) 0.86245 (11) 0.67763 (12) 0.77276 (2) 0.70190 (6) 0.84372 (5) −0.1046 −0.04852 (12) −0.11614 (12) −0.1678 −0.10617 (11) −0.1508 −0.02736 (10) −0.01190 (10) −0.07475 (11) −0.1280 −0.05670 (12) −0.0977 0.02390 (12) 0.04699 (16) 0.0080 0.12585 (17) 0.1404 0.18538 (16) 0.2390 0.16561 (13) 0.2056 0.08446 (11) 0.03785 (8) 0.06478 (8) 0.145770 (14) 0.17323 (4) 0.24216 (3) 0.062* 0.0417 (4) 0.0475 (4) 0.057* 0.0438 (4) 0.053* 0.0352 (3) 0.0352 (3) 0.0426 (4) 0.051* 0.0459 (4) 0.055* 0.0423 (4) 0.0550 (5) 0.066* 0.0637 (6) 0.076* 0.0652 (6) 0.078* 0.0544 (5) 0.065* 0.0398 (4) 0.0349 (3) 0.0361 (3) 0.04109 (9) 0.06732 (17) 0.06434 (17) Atomic displacement parameters (Å2) C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 U11 U22 U33 U12 U13 U23 0.0346 (8) 0.0462 (10) 0.0477 (11) 0.0507 (12) 0.0519 (11) 0.0409 (9) 0.0558 (11) 0.0535 (11) 0.0385 (8) 0.0360 (8) 0.0446 (10) 0.0391 (9) 0.0357 (9) 0.0449 (11) 0.0647 (14) 0.0862 (18) 0.0693 (14) 0.0354 (8) 0.0451 (10) 0.0463 (10) 0.0392 (10) 0.0429 (10) 0.0401 (9) 0.0511 (11) 0.0459 (9) 0.0362 (8) 0.0359 (8) 0.0443 (9) 0.0438 (9) 0.0388 (9) 0.0452 (10) 0.0508 (12) 0.0610 (13) 0.0544 (12) 0.0411 (9) 0.0478 (10) 0.0710 (14) 0.0878 (17) 0.0679 (13) 0.0479 (10) 0.0372 (9) 0.0307 (8) 0.0302 (7) 0.0319 (7) 0.0341 (8) 0.0492 (10) 0.0537 (11) 0.0780 (15) 0.0867 (18) 0.0585 (13) 0.0433 (10) 0.0060 (7) −0.0023 (8) −0.0045 (9) −0.0023 (9) 0.0073 (9) 0.0089 (7) 0.0099 (9) 0.0044 (8) 0.0073 (7) 0.0055 (6) 0.0052 (8) 0.0022 (8) 0.0023 (7) −0.0050 (9) −0.0081 (11) −0.0056 (13) −0.0083 (10) 0.0107 (7) 0.0114 (8) 0.0156 (10) 0.0289 (12) 0.0278 (10) 0.0177 (8) 0.0142 (8) 0.0066 (7) 0.0062 (6) 0.0041 (6) −0.0018 (7) −0.0017 (8) 0.0127 (8) 0.0205 (10) 0.0409 (13) 0.0374 (13) 0.0204 (10) 0.0011 (6) −0.0066 (8) −0.0112 (10) 0.0013 (10) 0.0135 (9) 0.0062 (7) 0.0113 (8) 0.0020 (7) 0.0016 (6) −0.0021 (6) −0.0032 (7) −0.0082 (8) −0.0036 (8) −0.0055 (10) 0.0016 (11) 0.0073 (11) 0.0008 (9) Acta Cryst. (2009). E65, m1370 sup-4 supporting information C18 N1 N2 Fe1 Cl1 Cl2 0.0411 (9) 0.0383 (7) 0.0398 (7) 0.04860 (17) 0.0545 (3) 0.0820 (4) 0.0383 (8) 0.0352 (7) 0.0372 (7) 0.04469 (15) 0.0818 (4) 0.0767 (4) 0.0422 (9) 0.0310 (6) 0.0308 (6) 0.02751 (13) 0.0594 (3) 0.0333 (2) 0.0008 (7) 0.0033 (6) 0.0008 (6) −0.00218 (11) 0.0111 (3) 0.0170 (3) 0.0138 (7) 0.0074 (5) 0.0070 (5) 0.00321 (10) −0.0006 (2) 0.0107 (2) −0.0006 (7) 0.0004 (5) −0.0009 (5) 0.00021 (10) 0.0081 (3) −0.0042 (2) Geometric parameters (Å, º) C1—N1 C1—C2 C1—C6 C2—C3 C2—H2 C3—C4 C3—H3 C4—C5 C4—H4 C5—C6 C5—H5 C6—C7 C7—C8 C7—H7 C8—C9 C8—H8 C9—N1 C9—C10 C10—N2 C10—C11 1.367 (2) 1.412 (3) 1.416 (3) 1.362 (3) 0.9300 1.407 (4) 0.9300 1.348 (3) 0.9300 1.417 (3) 0.9300 1.405 (3) 1.363 (3) 0.9300 1.409 (2) 0.9300 1.329 (2) 1.488 (2) 1.328 (2) 1.407 (2) C11—C12 C11—H11 C12—C13 C12—H12 C13—C18 C13—C14 C14—C15 C14—H14 C15—C16 C15—H15 C16—C17 C16—H16 C17—C18 C17—H17 C18—N2 Fe1—N1 Fe1—N2 Fe1—Cl2 Fe1—Cl1 1.360 (3) 0.9300 1.406 (3) 0.9300 1.418 (3) 1.418 (3) 1.360 (4) 0.9300 1.404 (4) 0.9300 1.371 (3) 0.9300 1.409 (3) 0.9300 1.376 (2) 2.1051 (14) 2.1008 (15) 2.2265 (6) 2.2341 (7) N1—C1—C2 N1—C1—C6 C2—C1—C6 C3—C2—C1 C3—C2—H2 C1—C2—H2 C2—C3—C4 C2—C3—H3 C4—C3—H3 C5—C4—C3 C5—C4—H4 C3—C4—H4 C4—C5—C6 C4—C5—H5 C6—C5—H5 C7—C6—C1 C7—C6—C5 C1—C6—C5 119.43 (16) 121.30 (16) 119.27 (17) 119.9 (2) 120.0 120.0 120.8 (2) 119.6 119.6 120.5 (2) 119.7 119.7 120.6 (2) 119.7 119.7 117.76 (17) 123.42 (19) 118.83 (19) C11—C12—C13 C11—C12—H12 C13—C12—H12 C12—C13—C18 C12—C13—C14 C18—C13—C14 C15—C14—C13 C15—C14—H14 C13—C14—H14 C14—C15—C16 C14—C15—H15 C16—C15—H15 C17—C16—C15 C17—C16—H16 C15—C16—H16 C16—C17—C18 C16—C17—H17 C18—C17—H17 120.10 (17) 119.9 119.9 118.12 (17) 123.11 (19) 118.76 (19) 120.4 (2) 119.8 119.8 120.5 (2) 119.8 119.8 120.9 (2) 119.5 119.5 119.7 (2) 120.2 120.2 Acta Cryst. (2009). E65, m1370 sup-5 supporting information C8—C7—C6 C8—C7—H7 C6—C7—H7 C7—C8—C9 C7—C8—H8 C9—C8—H8 N1—C9—C8 N1—C9—C10 C8—C9—C10 N2—C10—C11 N2—C10—C9 C11—C10—C9 C12—C11—C10 C12—C11—H11 C10—C11—H11 120.19 (17) 119.9 119.9 119.12 (18) 120.4 120.4 122.20 (17) 115.71 (14) 122.08 (16) 122.49 (17) 115.87 (14) 121.60 (15) 119.19 (17) 120.4 120.4 N2—C18—C17 N2—C18—C13 C17—C18—C13 C9—N1—C1 C9—N1—Fe1 C1—N1—Fe1 C10—N2—C18 C10—N2—Fe1 C18—N2—Fe1 N2—Fe1—N1 N2—Fe1—Cl2 N1—Fe1—Cl2 N2—Fe1—Cl1 N1—Fe1—Cl1 Cl2—Fe1—Cl1 119.52 (17) 120.76 (16) 119.71 (18) 119.39 (15) 113.92 (11) 125.75 (11) 119.32 (15) 114.56 (12) 126.12 (12) 78.06 (6) 111.38 (5) 117.15 (4) 113.32 (5) 107.24 (5) 121.65 (3) N1—C1—C2—C3 C6—C1—C2—C3 C1—C2—C3—C4 C2—C3—C4—C5 C3—C4—C5—C6 N1—C1—C6—C7 C2—C1—C6—C7 N1—C1—C6—C5 C2—C1—C6—C5 C4—C5—C6—C7 C4—C5—C6—C1 C1—C6—C7—C8 C5—C6—C7—C8 C6—C7—C8—C9 C7—C8—C9—N1 C7—C8—C9—C10 N1—C9—C10—N2 C8—C9—C10—N2 N1—C9—C10—C11 C8—C9—C10—C11 N2—C10—C11—C12 C9—C10—C11—C12 C10—C11—C12—C13 C11—C12—C13—C18 C11—C12—C13—C14 C12—C13—C14—C15 C18—C13—C14—C15 C13—C14—C15—C16 C14—C15—C16—C17 C15—C16—C17—C18 C16—C17—C18—N2 C16—C17—C18—C13 179.35 (18) −0.6 (3) 0.0 (3) 0.7 (3) −0.8 (3) 0.0 (3) 179.98 (17) −179.45 (16) 0.5 (3) −179.2 (2) 0.2 (3) 0.9 (3) −179.67 (19) −0.2 (3) −1.6 (3) 176.93 (17) −7.2 (2) 174.23 (17) 170.57 (16) −8.0 (3) 1.3 (3) −176.28 (17) −0.2 (3) −0.8 (3) −179.55 (19) 178.8 (2) 0.0 (3) −0.7 (4) 0.8 (4) −0.3 (4) −179.5 (2) −0.4 (3) C12—C13—C18—N2 C14—C13—C18—N2 C12—C13—C18—C17 C14—C13—C18—C17 C8—C9—N1—C1 C10—C9—N1—C1 C8—C9—N1—Fe1 C10—C9—N1—Fe1 C2—C1—N1—C9 C6—C1—N1—C9 C2—C1—N1—Fe1 C6—C1—N1—Fe1 C11—C10—N2—C18 C9—C10—N2—C18 C11—C10—N2—Fe1 C9—C10—N2—Fe1 C17—C18—N2—C10 C13—C18—N2—C10 C17—C18—N2—Fe1 C13—C18—N2—Fe1 C10—N2—Fe1—N1 C18—N2—Fe1—N1 C10—N2—Fe1—Cl2 C18—N2—Fe1—Cl2 C10—N2—Fe1—Cl1 C18—N2—Fe1—Cl1 C9—N1—Fe1—N2 C1—N1—Fe1—N2 C9—N1—Fe1—Cl2 C1—N1—Fe1—Cl2 C9—N1—Fe1—Cl1 C1—N1—Fe1—Cl1 0.7 (3) 179.59 (17) −178.33 (19) 0.5 (3) 2.5 (3) −176.11 (14) −167.08 (14) 14.32 (19) 178.34 (17) −1.7 (2) −13.4 (2) 166.54 (13) −1.3 (3) 176.38 (15) 178.50 (13) −3.78 (19) 179.36 (18) 0.3 (3) −0.4 (3) −179.52 (13) 8.54 (12) −171.64 (15) 123.25 (12) −56.93 (15) −95.27 (12) 84.55 (14) −12.47 (12) 178.74 (14) −120.54 (11) 70.66 (14) 98.51 (12) −70.28 (14) Acta Cryst. (2009). E65, m1370 sup-6