Bis(μ-4-nitro-2-{[2-(oxidometh-yl)phen-yl]imino-meth-yl}phenolato)bis-[chlorido(dimethyl sulfoxide)-iron(III)] dimethyl sulfoxide disolvate.

In the centrosymmetric dimeric title complex, [Fe(2)(C(14)H(10)N(2)O(4))(2)Cl(2)(C(2)H(6)OS)(2)]·2C(2)H(6)OS, two {Fe(L)Cl(DMSO)} units (L is the tridentate ligand 4-nitro-2-{[2-(oxidometh-yl)phen-yl]imino-meth-yl}phenolate; DMSO is dimethyl sulfoxide) are bridged by two O atoms, with an Fe⋯Fe separation of 3.1838 (8) Å. The coordination polyhedron of the Fe(III) atoms can be described as distorted octa-hedral, with four Fe-O, one Fe-N and one Fe-Cl coordination bonds. The L ligand is not planar, the dihedral angle between the 2-(oxidometh-yl)phen-yl]imino and 4-nitro-2-(imino-meth-yl)phenolate planes being 48.54 (9)°. The solvent DMSO molecule is disordered over two orientations with equal occupancy.

Related literature

For background to direct synthesis, see: Vassilyeva et al. (1997 ▶); Babich & Kokozay (1997 ▶); Kovbasyuk et al. (1997 ▶, 1998 ▶); Makhankova et al. (2002 ▶); Vinogradova et al. (2002 ▶); Pryma et al. (2003 ▶); Nesterov et al. (2004 ▶). For the structures of related complexes, see: Elmali et al. (2000 ▶); Chen et al. (2001 ▶); Koikawa et al. (2004 ▶); Madhu et al. (2005 ▶); Malassa et al. (2006 ▶).

Experimental

Crystal data

[Fe2(C14H10N2O4)2Cl2(C2H6OS)2]·2C2H6OS

M = 1035.59

Monoclinic,

a = 13.5003 (10) Å

b = 10.2566 (6) Å

c = 16.7453 (12) Å

β = 97.027 (6)°

V = 2301.3 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.99 mm−1

T = 293 K

0.35 × 0.05 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶). T min = 0.917, T max = 0.961

20394 measured reflections

5457 independent reflections

3448 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.160

S = 1.05

5457 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812017424/br2198sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017424/br2198Isup2.hkl

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

[Fe2(C14H10N2O4)2Cl2(C2H6OS)2]·2C2H6OS	F(000) = 1068
Mr = 1035.59	Dx = 1.495 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 4779 reflections
a = 13.5003 (10) Å	θ = 2.9–28.6°
b = 10.2566 (6) Å	µ = 0.99 mm−1
c = 16.7453 (12) Å	T = 293 K
β = 97.027 (6)°	Prism, dark-red
V = 2301.3 (3) Å3	0.35 × 0.05 × 0.04 mm
Z = 2

Oxford Diffraction Xcalibur Sapphire3 diffractometer	5457 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3448 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
Detector resolution: 16.1827 pixels mm-1	θmax = 28.7°, θmin = 2.9°
ω scans	h = −18→17
Absorption correction: multi-scan CrysAlis PRO, Oxford Diffraction (2010).	k = −12→13
Tmin = 0.917, Tmax = 0.961	l = −22→20
20394 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0648P)2 + 2.0858P] where P = (Fo2 + 2Fc2)/3
5457 reflections	(Δ/σ)max < 0.001
282 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.30 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 > 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe1	0.54824 (4)	0.35880 (5)	0.01293 (3)	0.04140 (18)
Cl1	0.56904 (9)	0.20842 (10)	0.11735 (7)	0.0625 (3)
S1	0.41820 (8)	0.12129 (9)	−0.05553 (7)	0.0503 (3)
S2A	0.9728 (3)	0.8274 (3)	−0.0026 (3)	0.1070 (13)	0.50
S2B	0.9931 (3)	0.7273 (4)	0.0176 (3)	0.1014 (11)	0.50
O1	0.48948 (18)	0.4976 (2)	0.07173 (14)	0.0400 (6)
O2	0.6276 (2)	0.2709 (3)	−0.06064 (17)	0.0525 (7)
O3	0.9361 (4)	0.6035 (5)	−0.2201 (3)	0.1141 (16)
O4	0.8945 (4)	0.4653 (6)	−0.3122 (3)	0.1294 (18)
O5	0.4218 (2)	0.2671 (2)	−0.03552 (17)	0.0511 (7)
O6	0.8873 (4)	0.7636 (6)	−0.0133 (4)	0.149 (2)
N1	0.6840 (2)	0.4594 (3)	0.05581 (19)	0.0418 (7)
N2	0.8868 (4)	0.5106 (6)	−0.2461 (3)	0.0842 (14)
C1	0.7040 (3)	0.5091 (4)	0.1360 (2)	0.0436 (9)
C2	0.6269 (3)	0.5362 (3)	0.1821 (2)	0.0430 (9)
C3	0.6529 (4)	0.5857 (4)	0.2587 (2)	0.0544 (11)
H3	0.6024	0.6068	0.2896	0.065*
C4	0.7499 (4)	0.6049 (5)	0.2908 (3)	0.0647 (13)
H4	0.7644	0.6391	0.3423	0.078*
C5	0.8258 (4)	0.5735 (5)	0.2467 (3)	0.0698 (14)
H5	0.8921	0.5849	0.2682	0.084*
C6	0.8024 (3)	0.5250 (5)	0.1704 (3)	0.0590 (11)
H6	0.8537	0.5020	0.1409	0.071*
C7	0.5167 (3)	0.5185 (4)	0.1551 (2)	0.0460 (9)
H7A	0.4932	0.4450	0.1840	0.055*
H7B	0.4819	0.5954	0.1708	0.055*
C8	0.7399 (3)	0.4989 (4)	0.0034 (2)	0.0482 (10)
H8	0.7824	0.5686	0.0179	0.058*
C9	0.7420 (3)	0.4444 (4)	−0.0756 (2)	0.0475 (9)
C10	0.6896 (3)	0.3290 (4)	−0.1021 (3)	0.0491 (10)
C11	0.7062 (3)	0.2774 (5)	−0.1774 (3)	0.0587 (12)
H11	0.6737	0.2010	−0.1954	0.070*
C12	0.7681 (4)	0.3357 (5)	−0.2244 (3)	0.0669 (14)
H12	0.7770	0.3003	−0.2741	0.080*
C13	0.8176 (3)	0.4479 (5)	−0.1977 (3)	0.0605 (12)
C14	0.8059 (3)	0.5023 (5)	−0.1244 (3)	0.0563 (11)
H14	0.8406	0.5776	−0.1074	0.068*
C15	0.3493 (7)	0.1186 (5)	−0.1514 (4)	0.128 (3)
H15A	0.2846	0.1559	−0.1486	0.192*
H15B	0.3419	0.0302	−0.1699	0.192*
H15C	0.3836	0.1683	−0.1880	0.192*
C16	0.3284 (5)	0.0564 (5)	0.0007 (4)	0.0949 (19)
H16A	0.3556	0.0515	0.0564	0.142*
H16B	0.3099	−0.0294	−0.0187	0.142*
H16C	0.2705	0.1116	−0.0047	0.142*
C17	1.0304 (7)	0.8170 (11)	0.0944 (5)	0.185 (5)
H17A	0.9879	0.8539	0.1304	0.278*	0.50
H17B	1.0924	0.8640	0.0990	0.278*	0.50
H17C	1.0432	0.7271	0.1081	0.278*	0.50
H17D	1.0274	0.9071	0.0788	0.278*	0.50
H17E	1.0979	0.7946	0.1145	0.278*	0.50
H17F	0.9882	0.8027	0.1357	0.278*	0.50
C18	1.0679 (6)	0.7618 (11)	−0.0498 (5)	0.161 (4)
H18A	1.0807	0.6741	−0.0313	0.242*	0.50
H18B	1.1271	0.8134	−0.0374	0.242*	0.50
H18C	1.0487	0.7613	−0.1069	0.242*	0.50
H18D	1.0479	0.7132	−0.0981	0.242*	0.50
H18E	1.1351	0.7390	−0.0291	0.242*	0.50
H18F	1.0643	0.8534	−0.0616	0.242*	0.50

	U11	U22	U33	U12	U13	U23
Fe1	0.0469 (3)	0.0338 (3)	0.0417 (3)	0.0014 (2)	−0.0023 (2)	−0.0014 (2)
Cl1	0.0832 (8)	0.0466 (6)	0.0540 (7)	0.0007 (5)	−0.0065 (6)	0.0103 (5)
S1	0.0594 (6)	0.0376 (5)	0.0516 (6)	−0.0015 (4)	−0.0028 (5)	−0.0012 (4)
S2A	0.091 (2)	0.0677 (19)	0.154 (4)	−0.0049 (17)	−0.022 (2)	0.008 (2)
S2B	0.095 (3)	0.086 (2)	0.122 (3)	0.0097 (19)	0.007 (2)	0.003 (2)
O1	0.0461 (15)	0.0377 (13)	0.0346 (14)	0.0014 (11)	−0.0013 (11)	0.0006 (10)
O2	0.0589 (18)	0.0421 (15)	0.0556 (18)	0.0060 (13)	0.0035 (15)	−0.0089 (13)
O3	0.120 (4)	0.138 (4)	0.093 (3)	−0.038 (3)	0.048 (3)	−0.010 (3)
O4	0.135 (4)	0.185 (5)	0.080 (3)	−0.030 (4)	0.061 (3)	−0.033 (3)
O5	0.0547 (17)	0.0385 (14)	0.0566 (17)	−0.0014 (12)	−0.0075 (14)	−0.0036 (12)
O6	0.106 (4)	0.166 (5)	0.171 (6)	−0.007 (4)	−0.004 (4)	−0.035 (4)
N1	0.0431 (18)	0.0406 (16)	0.0410 (18)	0.0047 (14)	0.0018 (15)	−0.0025 (14)
N2	0.075 (3)	0.116 (4)	0.064 (3)	0.002 (3)	0.021 (2)	−0.007 (3)
C1	0.049 (2)	0.041 (2)	0.039 (2)	−0.0025 (17)	−0.0016 (18)	−0.0005 (16)
C2	0.055 (2)	0.0372 (19)	0.035 (2)	0.0019 (17)	−0.0027 (18)	0.0032 (16)
C3	0.067 (3)	0.056 (2)	0.039 (2)	0.004 (2)	0.002 (2)	0.0011 (19)
C4	0.075 (3)	0.079 (3)	0.037 (2)	−0.005 (3)	−0.006 (2)	−0.005 (2)
C5	0.057 (3)	0.094 (4)	0.054 (3)	−0.007 (3)	−0.010 (2)	−0.007 (3)
C6	0.051 (3)	0.071 (3)	0.053 (3)	0.000 (2)	0.000 (2)	−0.007 (2)
C7	0.052 (2)	0.052 (2)	0.034 (2)	0.0045 (19)	0.0034 (17)	0.0009 (17)
C8	0.048 (2)	0.044 (2)	0.050 (2)	0.0010 (18)	−0.001 (2)	−0.0050 (18)
C9	0.047 (2)	0.054 (2)	0.041 (2)	0.0083 (18)	0.0032 (18)	−0.0002 (19)
C10	0.050 (2)	0.048 (2)	0.047 (2)	0.0150 (18)	−0.0036 (19)	−0.0059 (18)
C11	0.056 (3)	0.065 (3)	0.053 (3)	0.012 (2)	0.000 (2)	−0.016 (2)
C12	0.062 (3)	0.092 (4)	0.046 (3)	0.021 (3)	0.001 (2)	−0.018 (3)
C13	0.049 (3)	0.085 (3)	0.049 (3)	0.014 (2)	0.010 (2)	0.000 (2)
C14	0.049 (2)	0.065 (3)	0.053 (3)	0.007 (2)	0.001 (2)	−0.005 (2)
C15	0.219 (9)	0.055 (3)	0.088 (5)	−0.010 (4)	−0.071 (5)	−0.006 (3)
C16	0.094 (4)	0.061 (3)	0.139 (6)	−0.004 (3)	0.050 (4)	0.003 (3)
C17	0.143 (8)	0.269 (12)	0.129 (7)	0.099 (8)	−0.044 (6)	−0.062 (8)
C18	0.126 (7)	0.210 (10)	0.151 (8)	0.053 (7)	0.030 (6)	0.036 (8)

Fe1—Cl1	2.3228 (11)	C6—H6	0.9300
Fe1—O1	1.954 (2)	C7—H7A	0.9700
Fe1—O1i	2.064 (2)	C7—H7B	0.9700
Fe1—O2	1.949 (3)	C8—H8	0.9300
Fe1—O5	2.030 (3)	C8—C9	1.440 (6)
Fe1—N1	2.149 (3)	C9—C10	1.422 (6)
S1—O5	1.532 (3)	C9—C14	1.391 (6)
S1—C15	1.754 (6)	C10—C11	1.411 (6)
S1—C16	1.755 (6)	C11—H11	0.9300
S2A—O6	1.320 (6)	C11—C12	1.354 (7)
S2A—C17	1.717 (9)	C12—H12	0.9300
S2A—C18	1.724 (9)	C12—C13	1.378 (7)
S2B—O6	1.506 (6)	C13—C14	1.375 (6)
S2B—C17	1.611 (9)	C14—H14	0.9300
S2B—C18	1.641 (9)	C15—H15A	0.9600
O1—Fe1i	2.064 (2)	C15—H15B	0.9600
O1—C7	1.416 (4)	C15—H15C	0.9600
O2—C10	1.296 (5)	C16—H16A	0.9600
O3—N2	1.212 (6)	C16—H16B	0.9600
O4—N2	1.216 (6)	C16—H16C	0.9600
N1—C1	1.431 (5)	C17—H17A	0.9600
N1—C8	1.291 (5)	C17—H17B	0.9600
N2—C13	1.459 (7)	C17—H17C	0.9600
C1—C2	1.398 (6)	C17—H17D	0.9600
C1—C6	1.391 (5)	C17—H17E	0.9600
C2—C3	1.385 (5)	C17—H17F	0.9600
C2—C7	1.512 (5)	C18—H18A	0.9600
C3—H3	0.9300	C18—H18B	0.9600
C3—C4	1.367 (6)	C18—H18C	0.9600
C4—H4	0.9300	C18—H18D	0.9600
C4—C5	1.373 (7)	C18—H18E	0.9600
C5—H5	0.9300	C18—H18F	0.9600
C5—C6	1.370 (6)
O1i—Fe1—Cl1	171.00 (8)	H7A—C7—H7B	107.4
O1—Fe1—Cl1	97.10 (8)	N1—C8—H8	117.2
O1—Fe1—O1i	75.23 (11)	N1—C8—C9	125.6 (4)
O1—Fe1—O5	99.53 (11)	C9—C8—H8	117.2
O1—Fe1—N1	82.16 (11)	C10—C9—C8	123.1 (4)
O1i—Fe1—N1	90.88 (11)	C14—C9—C8	117.2 (4)
O2—Fe1—Cl1	98.25 (9)	C14—C9—C10	119.5 (4)
O2—Fe1—O1	160.70 (12)	O2—C10—C9	123.0 (4)
O2—Fe1—O1i	90.25 (11)	O2—C10—C11	119.4 (4)
O2—Fe1—O5	91.92 (12)	C11—C10—C9	117.7 (4)
O2—Fe1—N1	85.49 (12)	C10—C11—H11	119.0
O5—Fe1—Cl1	90.66 (9)	C12—C11—C10	122.0 (5)
O5—Fe1—O1i	86.06 (10)	C12—C11—H11	119.0
O5—Fe1—N1	175.99 (12)	C11—C12—H12	120.3
N1—Fe1—Cl1	92.74 (9)	C11—C12—C13	119.4 (4)
O5—S1—C15	102.4 (2)	C13—C12—H12	120.3
O5—S1—C16	105.0 (2)	C12—C13—N2	120.4 (5)
C15—S1—C16	99.3 (4)	C14—C13—N2	118.0 (5)
O6—S2A—C17	112.6 (6)	C14—C13—C12	121.5 (5)
O6—S2A—C18	115.6 (5)	C9—C14—H14	120.0
C17—S2A—C18	97.6 (4)	C13—C14—C9	119.9 (4)
O6—S2B—C17	108.9 (4)	C13—C14—H14	120.0
O6—S2B—C18	110.4 (5)	S1—C15—H15A	109.5
C17—S2B—C18	105.5 (6)	S1—C15—H15B	109.5
Fe1—O1—Fe1i	104.77 (11)	S1—C15—H15C	109.5
C7—O1—Fe1	122.3 (2)	H15A—C15—H15B	109.5
C7—O1—Fe1i	125.6 (2)	H15A—C15—H15C	109.5
C10—O2—Fe1	124.5 (2)	H15B—C15—H15C	109.5
S1—O5—Fe1	122.83 (16)	S1—C16—H16A	109.5
C1—N1—Fe1	122.7 (3)	S1—C16—H16B	109.5
C8—N1—Fe1	118.0 (3)	S1—C16—H16C	109.5
C8—N1—C1	117.8 (3)	H16A—C16—H16B	109.5
O3—N2—O4	121.5 (5)	H16A—C16—H16C	109.5
O3—N2—C13	120.5 (5)	H16B—C16—H16C	109.5
O4—N2—C13	117.9 (5)	S2A—C17—H17A	109.5
C2—C1—N1	121.4 (3)	S2A—C17—H17B	109.5
C6—C1—N1	119.5 (4)	S2A—C17—H17C	109.5
C6—C1—C2	119.1 (4)	S2B—C17—H17D	109.5
C1—C2—C7	125.7 (3)	S2B—C17—H17E	109.5
C3—C2—C1	117.6 (4)	S2B—C17—H17F	109.5
C3—C2—C7	116.7 (4)	H17A—C17—H17B	109.5
C2—C3—H3	118.7	H17A—C17—H17C	109.5
C4—C3—C2	122.6 (4)	H17B—C17—H17C	109.5
C4—C3—H3	118.7	H17D—C17—H17E	109.5
C3—C4—H4	120.1	H17D—C17—H17F	109.5
C3—C4—C5	119.8 (4)	H17E—C17—H17F	109.5
C5—C4—H4	120.1	S2A—C18—H18A	109.5
C4—C5—H5	120.5	S2A—C18—H18B	109.5
C6—C5—C4	118.9 (4)	S2A—C18—H18C	109.5
C6—C5—H5	120.5	S2B—C18—H18D	109.5
C1—C6—H6	119.1	S2B—C18—H18E	109.5
C5—C6—C1	121.9 (4)	S2B—C18—H18F	109.5
C5—C6—H6	119.1	H18A—C18—H18B	109.5
O1—C7—C2	116.1 (3)	H18A—C18—H18C	109.5
O1—C7—H7A	108.3	H18B—C18—H18C	109.5
O1—C7—H7B	108.3	H18D—C18—H18E	109.5
C2—C7—H7A	108.3	H18D—C18—H18F	109.5
C2—C7—H7B	108.3	H18E—C18—H18F	109.5