Bis[5-chloro-2-(phenyl-diazenyl-κN(2))pyridine-κN]bis-(thio-cyanato-κN)iron(II).

In the title complex, [Fe(NCS)(2)(C(11)H(8)ClN(3))(2)], the Fe(II) atom is coordinated by two N atoms from the thio-cyanate ligands and four N atoms from two chelating 5-chloro-2-(phenyl-diazen-yl)pyridine ligands, generating a fairly regular FeN(6) octa-hedral coordination geometry. The thio-cyanate ions are in a cis disposition and the pyridine N atoms are in a trans orientation. In the crystal, a short inter-molecular Cl⋯S contact [3.366 (3) Å] is observed.

Related literature

For background to diazenyl complexes, see: Krause & Krause (1980 ▶); Santra et al. (1999 ▶); Hotze, Caspers et al. (2004 ▶); Hotze, Kooijman et al. (2004 ▶). For applications of diazenyl compounds, see: Erkkila et al. (1999 ▶); Wong & Giandomenico (1999 ▶); Velder et al. (2000 ▶); Barf & Sheldon (1995 ▶). For structures of related diazenyl­imine complexes, see: Hansongnern et al. (2008 ▶); Ray et al. (2005 ▶); Senapoti et al. (2002) ▶. For background to diazenyl complexes, see: Byabartta et al. (2001 ▶).

Experimental

Crystal data

[Fe(NCS)2(C11H8ClN3)2]

M = 607.34

Monoclinic,

a = 9.5151 (3) Å

b = 23.7391 (9) Å

c = 12.1550 (4) Å

β = 96.209 (1)°

V = 2729.46 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.93 mm−1

T = 293 K

0.34 × 0.17 × 0.09 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.916, T max = 1.000

29379 measured reflections

4809 independent reflections

4189 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.110

S = 1.08

4809 reflections

334 parameters

H-atom parameters constrained

Δρmax = 0.95 e Å−3

Δρmin = −0.75 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶), WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812014286/hb6716sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014286/hb6716Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Fe(NCS)2(C11H8ClN3)2]	F(000) = 1232
Mr = 607.34	Dx = 1.478 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7953 reflections
a = 9.5151 (3) Å	θ = 2.3–25.4°
b = 23.7391 (9) Å	µ = 0.93 mm−1
c = 12.1550 (4) Å	T = 293 K
β = 96.209 (1)°	Block, red-brown
V = 2729.46 (16) Å3	0.34 × 0.17 × 0.09 mm
Z = 4

Bruker SMART APEX CCD diffractometer	4809 independent reflections
Radiation source: fine-focus sealed tube	4189 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Frames, each covering 0.3 ° in ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −11→11
Tmin = 0.916, Tmax = 1.000	k = −28→28
29379 measured reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0511P)2 + 2.004P] where P = (Fo2 + 2Fc2)/3
4809 reflections	(Δ/σ)max = 0.001
334 parameters	Δρmax = 0.95 e Å−3
0 restraints	Δρmin = −0.75 e Å−3

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 > 2σ(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 al data will be even larger.

	x	y	z	Uiso*/Ueq
Fe1	0.26710 (4)	0.199109 (16)	0.72956 (3)	0.03803 (13)
N1	0.4302 (2)	0.15150 (10)	0.77250 (18)	0.0439 (5)
N2	0.4637 (2)	0.22105 (11)	0.90825 (19)	0.0513 (6)
N3	0.3387 (2)	0.23370 (10)	0.86513 (17)	0.0415 (5)
N4	0.1056 (2)	0.24866 (10)	0.70140 (17)	0.0432 (5)
N5	−0.0086 (2)	0.16663 (12)	0.7497 (2)	0.0536 (6)
N6	0.1197 (2)	0.15144 (10)	0.77242 (18)	0.0451 (5)
N7	0.2284 (2)	0.16225 (10)	0.58695 (19)	0.0490 (6)
N8	0.3889 (2)	0.25196 (11)	0.66138 (19)	0.0470 (5)
S2	0.49476 (8)	0.34626 (3)	0.56230 (8)	0.0626 (2)
S1	0.20586 (13)	0.09807 (7)	0.39640 (12)	0.1316 (7)
C1	0.4725 (3)	0.10415 (13)	0.7267 (3)	0.0522 (7)
H1	0.4145	0.0873	0.6694	0.063*
C2	0.6012 (3)	0.07977 (14)	0.7631 (3)	0.0613 (9)
C3	0.6913 (3)	0.10504 (17)	0.8452 (3)	0.0713 (10)
H3	0.7798	0.0898	0.8675	0.086*
C4	0.6470 (3)	0.15305 (17)	0.8927 (3)	0.0667 (9)
H4	0.7047	0.1709	0.9488	0.080*
C5	0.5151 (3)	0.17485 (14)	0.8567 (2)	0.0494 (7)
C6	0.2817 (3)	0.28345 (12)	0.9103 (2)	0.0458 (6)
C7	0.3583 (4)	0.33294 (15)	0.9139 (3)	0.0676 (9)
H7	0.4501	0.3333	0.8943	0.081*
C8	0.2971 (5)	0.38131 (17)	0.9467 (4)	0.0913 (13)
H8	0.3475	0.4149	0.9496	0.110*
C9	0.1606 (5)	0.38048 (18)	0.9755 (3)	0.0905 (13)
H9	0.1187	0.4137	0.9958	0.109*
C10	0.0864 (4)	0.33076 (17)	0.9743 (3)	0.0717 (10)
H10	−0.0043	0.3303	0.9961	0.086*
C11	0.1460 (3)	0.28201 (14)	0.9411 (2)	0.0520 (7)
H11	0.0958	0.2483	0.9392	0.062*
C12	0.1023 (3)	0.30337 (13)	0.6782 (2)	0.0496 (7)
H12	0.1861	0.3220	0.6685	0.059*
C13	−0.0229 (3)	0.33307 (15)	0.6681 (3)	0.0611 (8)
C14	−0.1487 (4)	0.30664 (18)	0.6787 (3)	0.0751 (11)
H14	−0.2334	0.3265	0.6711	0.090*
C15	−0.1460 (3)	0.25012 (18)	0.7007 (3)	0.0711 (10)
H15	−0.2297	0.2307	0.7069	0.085*
C16	−0.0178 (3)	0.22207 (14)	0.7138 (2)	0.0519 (7)
C17	0.1347 (3)	0.09386 (12)	0.8076 (2)	0.0503 (7)
C18	0.0563 (4)	0.05231 (16)	0.7497 (3)	0.0752 (10)
H18	−0.0066	0.0612	0.6882	0.090*
C19	0.0737 (5)	−0.00269 (18)	0.7856 (4)	0.0987 (15)
H19	0.0232	−0.0313	0.7470	0.118*
C20	0.1640 (5)	−0.01550 (17)	0.8771 (5)	0.0998 (15)
H20	0.1738	−0.0527	0.9007	0.120*
C21	0.2400 (4)	0.02575 (16)	0.9341 (4)	0.0832 (11)
H21	0.3010	0.0167	0.9966	0.100*
C22	0.2266 (3)	0.08071 (13)	0.8994 (3)	0.0580 (8)
H22	0.2792	0.1089	0.9377	0.070*
C23	0.2177 (3)	0.13531 (15)	0.5084 (3)	0.0592 (8)
C24	0.4349 (3)	0.29088 (12)	0.6208 (2)	0.0423 (6)
Cl1	0.64768 (11)	0.01811 (4)	0.70172 (10)	0.0874 (3)
Cl2	−0.01594 (12)	0.40406 (4)	0.64356 (10)	0.0929 (3)

	U11	U22	U33	U12	U13	U23
Fe1	0.0315 (2)	0.0475 (2)	0.0347 (2)	0.00046 (15)	0.00200 (14)	−0.00205 (15)
N1	0.0344 (11)	0.0541 (14)	0.0438 (12)	0.0022 (10)	0.0072 (9)	0.0068 (10)
N2	0.0360 (12)	0.0753 (17)	0.0416 (13)	−0.0022 (11)	−0.0004 (10)	0.0006 (12)
N3	0.0342 (11)	0.0558 (14)	0.0344 (11)	−0.0058 (10)	0.0034 (9)	0.0012 (10)
N4	0.0372 (12)	0.0567 (14)	0.0348 (11)	0.0067 (10)	−0.0001 (9)	−0.0054 (10)
N5	0.0361 (13)	0.0714 (17)	0.0526 (14)	−0.0047 (11)	0.0020 (10)	−0.0058 (12)
N6	0.0369 (12)	0.0562 (14)	0.0422 (12)	−0.0057 (10)	0.0040 (9)	−0.0072 (10)
N7	0.0446 (13)	0.0613 (15)	0.0404 (13)	0.0026 (11)	0.0017 (10)	−0.0108 (11)
N8	0.0423 (13)	0.0547 (14)	0.0447 (13)	0.0013 (11)	0.0084 (10)	0.0003 (11)
S2	0.0505 (4)	0.0526 (5)	0.0840 (6)	0.0021 (3)	0.0047 (4)	0.0187 (4)
S1	0.0840 (8)	0.1876 (15)	0.1193 (10)	0.0205 (8)	−0.0075 (7)	−0.1068 (11)
C1	0.0482 (16)	0.0534 (17)	0.0567 (18)	0.0057 (13)	0.0130 (13)	0.0084 (14)
C2	0.0548 (18)	0.066 (2)	0.067 (2)	0.0172 (16)	0.0222 (16)	0.0224 (16)
C3	0.0431 (17)	0.105 (3)	0.067 (2)	0.0237 (18)	0.0115 (16)	0.025 (2)
C4	0.0398 (16)	0.104 (3)	0.0553 (19)	0.0097 (17)	−0.0004 (14)	0.0079 (18)
C5	0.0355 (14)	0.0702 (19)	0.0423 (15)	−0.0004 (13)	0.0026 (12)	0.0084 (14)
C6	0.0485 (16)	0.0556 (17)	0.0330 (13)	−0.0068 (13)	0.0030 (11)	−0.0059 (12)
C7	0.066 (2)	0.071 (2)	0.067 (2)	−0.0203 (18)	0.0130 (17)	−0.0172 (17)
C8	0.122 (4)	0.066 (2)	0.088 (3)	−0.027 (2)	0.024 (3)	−0.024 (2)
C9	0.127 (4)	0.070 (3)	0.079 (3)	0.012 (3)	0.031 (3)	−0.023 (2)
C10	0.076 (2)	0.087 (3)	0.056 (2)	0.010 (2)	0.0224 (17)	−0.0098 (18)
C11	0.0513 (17)	0.0639 (19)	0.0417 (15)	−0.0032 (14)	0.0093 (12)	−0.0030 (13)
C12	0.0478 (16)	0.0626 (19)	0.0369 (14)	0.0100 (14)	−0.0019 (12)	−0.0028 (13)
C13	0.060 (2)	0.072 (2)	0.0484 (17)	0.0227 (17)	−0.0063 (14)	−0.0040 (15)
C14	0.048 (2)	0.102 (3)	0.072 (2)	0.0312 (19)	−0.0086 (16)	−0.005 (2)
C15	0.0358 (16)	0.100 (3)	0.075 (2)	0.0076 (17)	−0.0038 (15)	−0.003 (2)
C16	0.0358 (15)	0.073 (2)	0.0459 (16)	0.0016 (14)	−0.0026 (12)	−0.0059 (14)
C17	0.0450 (15)	0.0504 (17)	0.0568 (17)	−0.0108 (13)	0.0118 (13)	−0.0095 (13)
C18	0.069 (2)	0.071 (2)	0.083 (2)	−0.0176 (18)	−0.0039 (19)	−0.0160 (19)
C19	0.097 (3)	0.064 (3)	0.133 (4)	−0.033 (2)	0.001 (3)	−0.022 (3)
C20	0.101 (3)	0.055 (2)	0.141 (4)	−0.019 (2)	0.001 (3)	0.006 (3)
C21	0.091 (3)	0.061 (2)	0.095 (3)	−0.014 (2)	−0.003 (2)	0.016 (2)
C22	0.0599 (19)	0.0500 (18)	0.0631 (19)	−0.0108 (14)	0.0020 (15)	0.0015 (14)
C23	0.0355 (15)	0.078 (2)	0.063 (2)	0.0087 (14)	−0.0004 (13)	−0.0181 (17)
C24	0.0346 (13)	0.0487 (16)	0.0428 (14)	0.0077 (12)	0.0004 (11)	−0.0032 (12)
Cl1	0.0880 (7)	0.0692 (6)	0.1091 (8)	0.0340 (5)	0.0298 (6)	0.0175 (5)
Cl2	0.1028 (8)	0.0715 (6)	0.1004 (8)	0.0383 (6)	−0.0082 (6)	0.0028 (5)

Fe1—N3	1.900 (2)	C6—C11	1.384 (4)
Fe1—N6	1.917 (2)	C7—C8	1.366 (5)
Fe1—N4	1.936 (2)	C7—H7	0.9300
Fe1—N7	1.941 (2)	C8—C9	1.381 (6)
Fe1—N1	1.945 (2)	C8—H8	0.9300
Fe1—N8	1.952 (2)	C9—C10	1.375 (6)
N1—C1	1.336 (4)	C9—H9	0.9300
N1—C5	1.352 (4)	C10—C11	1.369 (5)
N2—N3	1.282 (3)	C10—H10	0.9300
N2—C5	1.379 (4)	C11—H11	0.9300
N3—C6	1.433 (4)	C12—C13	1.378 (4)
N4—C12	1.329 (4)	C12—H12	0.9300
N4—C16	1.356 (4)	C13—C14	1.370 (5)
N5—N6	1.274 (3)	C13—Cl2	1.714 (4)
N5—C16	1.386 (4)	C14—C15	1.368 (5)
N6—C17	1.435 (4)	C14—H14	0.9300
N7—C23	1.144 (4)	C15—C16	1.384 (4)
N8—C24	1.156 (4)	C15—H15	0.9300
S2—C24	1.626 (3)	C17—C22	1.378 (4)
S1—C23	1.617 (3)	C17—C18	1.382 (4)
C1—C2	1.383 (4)	C18—C19	1.381 (6)
C1—H1	0.9300	C18—H18	0.9300
C2—C3	1.380 (5)	C19—C20	1.364 (6)
C2—Cl1	1.722 (4)	C19—H19	0.9300
C3—C4	1.365 (5)	C20—C21	1.361 (6)
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.384 (4)	C21—C22	1.373 (5)
C4—H4	0.9300	C21—H21	0.9300
C6—C7	1.380 (4)	C22—H22	0.9300
N3—Fe1—N6	102.92 (9)	C8—C7—H7	120.5
N3—Fe1—N4	95.39 (9)	C6—C7—H7	120.5
N6—Fe1—N4	79.44 (10)	C7—C8—C9	120.2 (4)
N3—Fe1—N7	169.99 (9)	C7—C8—H8	119.9
N6—Fe1—N7	84.43 (10)	C9—C8—H8	119.9
N4—Fe1—N7	92.62 (9)	C10—C9—C8	120.4 (4)
N3—Fe1—N1	79.49 (10)	C10—C9—H9	119.8
N6—Fe1—N1	99.78 (10)	C8—C9—H9	119.8
N4—Fe1—N1	174.56 (9)	C11—C10—C9	120.0 (3)
N7—Fe1—N1	92.66 (10)	C11—C10—H10	120.0
N3—Fe1—N8	85.23 (9)	C9—C10—H10	120.0
N6—Fe1—N8	168.44 (10)	C10—C11—C6	119.2 (3)
N4—Fe1—N8	91.75 (10)	C10—C11—H11	120.4
N7—Fe1—N8	88.54 (10)	C6—C11—H11	120.4
N1—Fe1—N8	89.68 (10)	N4—C12—C13	121.3 (3)
C1—N1—C5	118.6 (2)	N4—C12—H12	119.3
C1—N1—Fe1	130.1 (2)	C13—C12—H12	119.3
C5—N1—Fe1	111.03 (19)	C14—C13—C12	120.9 (3)
N3—N2—C5	111.1 (2)	C14—C13—Cl2	121.1 (3)
N2—N3—C6	114.1 (2)	C12—C13—Cl2	118.0 (3)
N2—N3—Fe1	118.86 (18)	C15—C14—C13	118.0 (3)
C6—N3—Fe1	125.00 (17)	C15—C14—H14	121.0
C12—N4—C16	118.5 (2)	C13—C14—H14	121.0
C12—N4—Fe1	129.2 (2)	C14—C15—C16	119.5 (3)
C16—N4—Fe1	112.2 (2)	C14—C15—H15	120.3
N6—N5—C16	111.3 (2)	C16—C15—H15	120.3
N5—N6—C17	113.3 (2)	N4—C16—C15	121.8 (3)
N5—N6—Fe1	119.1 (2)	N4—C16—N5	116.8 (2)
C17—N6—Fe1	126.25 (18)	C15—C16—N5	121.2 (3)
C23—N7—Fe1	171.1 (3)	C22—C17—C18	120.7 (3)
C24—N8—Fe1	164.8 (2)	C22—C17—N6	119.4 (2)
N1—C1—C2	121.0 (3)	C18—C17—N6	119.9 (3)
N1—C1—H1	119.5	C19—C18—C17	118.3 (4)
C2—C1—H1	119.5	C19—C18—H18	120.8
C3—C2—C1	120.6 (3)	C17—C18—H18	120.8
C3—C2—Cl1	120.9 (3)	C20—C19—C18	120.8 (4)
C1—C2—Cl1	118.5 (3)	C20—C19—H19	119.6
C4—C3—C2	118.2 (3)	C18—C19—H19	119.6
C4—C3—H3	120.9	C21—C20—C19	120.5 (4)
C2—C3—H3	120.9	C21—C20—H20	119.7
C3—C4—C5	119.3 (3)	C19—C20—H20	119.7
C3—C4—H4	120.4	C20—C21—C22	120.0 (4)
C5—C4—H4	120.4	C20—C21—H21	120.0
N1—C5—N2	117.2 (2)	C22—C21—H21	120.0
N1—C5—C4	122.2 (3)	C21—C22—C17	119.6 (3)
N2—C5—C4	120.5 (3)	C21—C22—H22	120.2
C7—C6—C11	121.1 (3)	C17—C22—H22	120.2
C7—C6—N3	119.6 (3)	N7—C23—S1	178.5 (3)
C11—C6—N3	119.1 (3)	N8—C24—S2	178.2 (2)
C8—C7—C6	119.0 (3)
N3—Fe1—N1—C1	173.6 (3)	Cl1—C2—C3—C4	−178.3 (3)
N6—Fe1—N1—C1	72.2 (2)	C2—C3—C4—C5	−0.6 (5)
N7—Fe1—N1—C1	−12.7 (2)	C1—N1—C5—N2	−174.8 (2)
N8—Fe1—N1—C1	−101.2 (2)	Fe1—N1—C5—N2	10.3 (3)
N3—Fe1—N1—C5	−12.28 (18)	C1—N1—C5—C4	3.5 (4)
N6—Fe1—N1—C5	−113.74 (19)	Fe1—N1—C5—C4	−171.4 (2)
N7—Fe1—N1—C5	161.45 (19)	N3—N2—C5—N1	0.3 (4)
N8—Fe1—N1—C5	72.93 (19)	N3—N2—C5—C4	−178.0 (3)
C5—N2—N3—C6	−176.4 (2)	C3—C4—C5—N1	−2.7 (5)
C5—N2—N3—Fe1	−11.8 (3)	C3—C4—C5—N2	175.6 (3)
N6—Fe1—N3—N2	111.7 (2)	N2—N3—C6—C7	53.0 (4)
N4—Fe1—N3—N2	−167.9 (2)	Fe1—N3—C6—C7	−110.6 (3)
N7—Fe1—N3—N2	−24.9 (7)	N2—N3—C6—C11	−132.3 (3)
N1—Fe1—N3—N2	14.0 (2)	Fe1—N3—C6—C11	64.1 (3)
N8—Fe1—N3—N2	−76.6 (2)	C11—C6—C7—C8	−1.1 (5)
N6—Fe1—N3—C6	−85.4 (2)	N3—C6—C7—C8	173.4 (3)
N4—Fe1—N3—C6	−5.0 (2)	C6—C7—C8—C9	−0.1 (6)
N7—Fe1—N3—C6	138.0 (5)	C7—C8—C9—C10	1.7 (7)
N1—Fe1—N3—C6	176.8 (2)	C8—C9—C10—C11	−2.1 (6)
N8—Fe1—N3—C6	86.3 (2)	C9—C10—C11—C6	0.8 (5)
N3—Fe1—N4—C12	67.2 (2)	C7—C6—C11—C10	0.8 (5)
N6—Fe1—N4—C12	169.3 (2)	N3—C6—C11—C10	−173.8 (3)
N7—Fe1—N4—C12	−106.8 (2)	C16—N4—C12—C13	0.8 (4)
N8—Fe1—N4—C12	−18.2 (2)	Fe1—N4—C12—C13	−175.3 (2)
N3—Fe1—N4—C16	−109.20 (19)	N4—C12—C13—C14	−1.9 (5)
N6—Fe1—N4—C16	−7.03 (18)	N4—C12—C13—Cl2	177.4 (2)
N7—Fe1—N4—C16	76.81 (19)	C12—C13—C14—C15	0.7 (5)
N8—Fe1—N4—C16	165.42 (19)	Cl2—C13—C14—C15	−178.5 (3)
C16—N5—N6—C17	−178.6 (2)	C13—C14—C15—C16	1.3 (5)
C16—N5—N6—Fe1	−11.1 (3)	C12—N4—C16—C15	1.3 (4)
N3—Fe1—N6—N5	103.7 (2)	Fe1—N4—C16—C15	178.1 (2)
N4—Fe1—N6—N5	10.6 (2)	C12—N4—C16—N5	−173.2 (2)
N7—Fe1—N6—N5	−83.1 (2)	Fe1—N4—C16—N5	3.6 (3)
N1—Fe1—N6—N5	−174.9 (2)	C14—C15—C16—N4	−2.4 (5)
N8—Fe1—N6—N5	−30.3 (6)	C14—C15—C16—N5	171.9 (3)
N3—Fe1—N6—C17	−90.5 (2)	N6—N5—C16—N4	4.5 (4)
N4—Fe1—N6—C17	176.3 (2)	N6—N5—C16—C15	−170.0 (3)
N7—Fe1—N6—C17	82.6 (2)	N5—N6—C17—C22	−133.9 (3)
N1—Fe1—N6—C17	−9.1 (2)	Fe1—N6—C17—C22	59.6 (3)
N8—Fe1—N6—C17	135.4 (5)	N5—N6—C17—C18	45.6 (4)
N3—Fe1—N8—C24	−87.5 (9)	Fe1—N6—C17—C18	−120.9 (3)
N6—Fe1—N8—C24	47.9 (11)	C22—C17—C18—C19	−0.8 (6)
N4—Fe1—N8—C24	7.8 (9)	N6—C17—C18—C19	179.8 (3)
N7—Fe1—N8—C24	100.4 (9)	C17—C18—C19—C20	1.2 (7)
N1—Fe1—N8—C24	−167.0 (9)	C18—C19—C20—C21	−0.7 (8)
C5—N1—C1—C2	−0.9 (4)	C19—C20—C21—C22	−0.3 (8)
Fe1—N1—C1—C2	172.8 (2)	C20—C21—C22—C17	0.8 (6)
N1—C1—C2—C3	−2.3 (5)	C18—C17—C22—C21	−0.2 (5)
N1—C1—C2—Cl1	179.0 (2)	N6—C17—C22—C21	179.2 (3)
C1—C2—C3—C4	3.1 (5)

Table 1

Selected bond lengths (Å)

Fe1—N3	1.900 (2)
Fe1—N6	1.917 (2)
Fe1—N4	1.936 (2)
Fe1—N7	1.941 (2)
Fe1—N1	1.945 (2)
Fe1—N8	1.952 (2)