{2,2'-[(5-Bromo-pyridine-2,3-di-yl)bis-(nitrilo-methyl-idyne)]diphenolato}chlorido(N,N-dimethyl-formamide)iron(III).

In the title complex, [Fe(C(19)H(12)BrClN(3)O(2))(C(3)H(7)NO)], the Fe(III) atom is coordinated by an N,N,O,O-tetra-dentate Schiff base ligand and trans coordinated by a chloride anion and the O atom of an N,N-dimethyl-formamide mol-ecule. The resulting geometry is distorted octa-hedral within a ClN(2)O(3) donor set.

Related literature

For the optical, electronic, magnetic, biological and catalytic properties of complexes containing salicylaldehyde ligands, see: Alam et al. (2003 ▶); Oshiob et al. (2005 ▶); Zelewsky & von Knof (1999 ▶).

Experimental

Crystal data

[Fe(C19H12BrClN3O2)(C3H7NO)]

M = 558.62

Monoclinic,

a = 13.1626 (11) Å

b = 15.3553 (13) Å

c = 12.6376 (11) Å

β = 118.186 (1)°

V = 2251.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.60 mm−1

T = 293 K

0.21 × 0.15 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.612, T max = 0.763

11869 measured reflections

4421 independent reflections

3468 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.117

S = 1.04

4421 reflections

291 parameters

H-atom parameters constrained

Δρmax = 1.35 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031432/tk2520sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031432/tk2520Isup2.hkl

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

[Fe(C19H12BrClN3O2)(C3H7NO)]	Z = 4
Mr = 558.62	F(000) = 1122
Monoclinic, P21/c	Dx = 1.647 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.1626 (11) Å	µ = 2.60 mm−1
b = 15.3553 (13) Å	T = 293 K
c = 12.6376 (11) Å	Block, red-brown
β = 118.186 (1)°	0.21 × 0.15 × 0.11 mm
V = 2251.4 (3) Å3

Bruker APEXII CCD area-detector diffractometer	4421 independent reflections
Radiation source: fine-focus sealed tube	3468 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.612, Tmax = 0.763	k = −14→18
11869 measured reflections	l = −15→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0664P)2 + 1.0974P] where P = (Fo2 + 2Fc2)/3
4421 reflections	(Δ/σ)max = 0.002
291 parameters	Δρmax = 1.35 e Å−3
0 restraints	Δρmin = −0.39 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
Fe1	0.81172 (4)	0.45734 (3)	0.12689 (4)	0.04193 (15)
Br1	0.45611 (3)	0.63148 (3)	0.36373 (4)	0.06309 (16)
Cl1	0.68099 (7)	0.34010 (6)	0.05361 (9)	0.0584 (3)
O1	0.94591 (19)	0.38509 (16)	0.1821 (2)	0.0511 (6)
O2	0.78233 (19)	0.49869 (16)	−0.0266 (2)	0.0505 (6)
O3	0.9319 (2)	0.56438 (16)	0.2007 (2)	0.0555 (6)
N1	0.8280 (2)	0.45132 (16)	0.3011 (2)	0.0412 (6)
N2	0.6755 (2)	0.54061 (16)	0.1157 (2)	0.0401 (6)
N3	1.0807 (2)	0.63665 (18)	0.1998 (3)	0.0498 (7)
N4	0.7329 (2)	0.48025 (19)	0.4177 (3)	0.0501 (7)
C1	0.7382 (3)	0.4908 (2)	0.3158 (3)	0.0410 (7)
C2	0.6585 (3)	0.53962 (19)	0.2178 (3)	0.0394 (7)
C3	0.5712 (3)	0.5822 (2)	0.2311 (3)	0.0450 (7)
H3	0.5163	0.6158	0.1694	0.054*
C4	0.5694 (3)	0.5727 (2)	0.3380 (3)	0.0472 (8)
C5	0.6484 (3)	0.5206 (2)	0.4282 (3)	0.0515 (8)
H5	0.6426	0.5135	0.4982	0.062*
C6	0.9158 (3)	0.4183 (2)	0.3952 (3)	0.0452 (7)
H6	0.9172	0.4251	0.4690	0.054*
C7	1.0095 (3)	0.3728 (2)	0.3937 (3)	0.0454 (8)
C8	1.0937 (3)	0.3383 (2)	0.5057 (3)	0.0551 (9)
H8	1.0876	0.3493	0.5748	0.066*
C9	1.1837 (3)	0.2891 (3)	0.5130 (4)	0.0632 (11)
H9	1.2383	0.2667	0.5864	0.076*
C10	1.1924 (3)	0.2731 (2)	0.4092 (4)	0.0612 (10)
H10	1.2529	0.2392	0.4141	0.073*
C11	1.1146 (3)	0.3058 (2)	0.3007 (4)	0.0547 (9)
H11	1.1235	0.2947	0.2332	0.066*
C12	1.0196 (3)	0.3567 (2)	0.2898 (3)	0.0448 (8)
C13	0.6053 (3)	0.5821 (2)	0.0183 (3)	0.0414 (7)
H13	0.5427	0.6095	0.0191	0.050*
C14	0.6146 (3)	0.5897 (2)	−0.0883 (3)	0.0424 (7)
C15	0.5322 (3)	0.6421 (2)	−0.1808 (3)	0.0524 (9)
H15	0.4718	0.6658	−0.1716	0.063*
C16	0.5389 (3)	0.6588 (3)	−0.2836 (3)	0.0594 (10)
H16	0.4838	0.6936	−0.3434	0.071*
C17	0.6287 (3)	0.6233 (3)	−0.2976 (4)	0.0604 (10)
H17	0.6344	0.6355	−0.3667	0.072*
C18	0.7094 (3)	0.5704 (2)	−0.2111 (3)	0.0539 (9)
H18	0.7687	0.5475	−0.2229	0.065*
C19	0.7045 (3)	0.5504 (2)	−0.1065 (3)	0.0439 (7)
C20	0.9823 (3)	0.5955 (2)	0.1477 (3)	0.0512 (8)
H20	0.9474	0.5890	0.0647	0.061*
C21	1.1401 (4)	0.6472 (3)	0.3283 (4)	0.0786 (13)
H21A	1.1111	0.6978	0.3498	0.118*
H21B	1.2212	0.6541	0.3553	0.118*
H21C	1.1277	0.5967	0.3654	0.118*
C22	1.1359 (3)	0.6718 (3)	0.1329 (4)	0.0615 (10)
H22A	1.0840	0.6676	0.0484	0.092*
H22B	1.2047	0.6394	0.1519	0.092*
H22C	1.1553	0.7318	0.1542	0.092*

	U11	U22	U33	U12	U13	U23
Fe1	0.0323 (2)	0.0442 (3)	0.0446 (3)	0.00752 (19)	0.0144 (2)	0.0030 (2)
Br1	0.0530 (2)	0.0760 (3)	0.0671 (3)	0.01648 (18)	0.0340 (2)	0.00264 (19)
Cl1	0.0388 (4)	0.0490 (5)	0.0738 (6)	0.0018 (4)	0.0156 (4)	−0.0049 (4)
O1	0.0363 (12)	0.0610 (15)	0.0522 (14)	0.0125 (10)	0.0177 (11)	0.0032 (11)
O2	0.0456 (13)	0.0555 (14)	0.0484 (13)	0.0124 (11)	0.0205 (11)	0.0053 (11)
O3	0.0466 (13)	0.0568 (15)	0.0615 (15)	−0.0083 (11)	0.0242 (12)	−0.0003 (12)
N1	0.0337 (13)	0.0393 (14)	0.0467 (15)	0.0040 (11)	0.0158 (12)	0.0030 (11)
N2	0.0331 (13)	0.0386 (14)	0.0421 (14)	0.0028 (11)	0.0124 (11)	0.0006 (11)
N3	0.0424 (15)	0.0472 (16)	0.0608 (19)	0.0015 (12)	0.0252 (14)	0.0027 (13)
N4	0.0489 (16)	0.0571 (17)	0.0465 (16)	0.0089 (14)	0.0244 (14)	0.0070 (13)
C1	0.0333 (16)	0.0375 (16)	0.0491 (18)	0.0010 (13)	0.0169 (14)	−0.0013 (13)
C2	0.0326 (15)	0.0386 (16)	0.0434 (17)	−0.0005 (12)	0.0151 (13)	−0.0031 (13)
C3	0.0350 (16)	0.0421 (17)	0.0494 (19)	0.0038 (13)	0.0131 (14)	0.0007 (14)
C4	0.0375 (17)	0.0488 (19)	0.057 (2)	0.0019 (14)	0.0239 (16)	−0.0022 (16)
C5	0.053 (2)	0.055 (2)	0.051 (2)	0.0086 (17)	0.0283 (17)	0.0060 (16)
C6	0.0380 (17)	0.0472 (18)	0.0455 (19)	0.0030 (14)	0.0157 (15)	0.0015 (14)
C7	0.0305 (16)	0.0424 (18)	0.054 (2)	0.0017 (13)	0.0119 (14)	0.0072 (14)
C8	0.0396 (18)	0.056 (2)	0.055 (2)	0.0002 (16)	0.0102 (16)	0.0072 (17)
C9	0.0354 (18)	0.057 (2)	0.074 (3)	0.0052 (16)	0.0073 (18)	0.019 (2)
C10	0.0312 (17)	0.051 (2)	0.090 (3)	0.0099 (15)	0.0195 (19)	0.0130 (19)
C11	0.0398 (18)	0.0478 (19)	0.076 (3)	0.0064 (15)	0.0266 (18)	0.0050 (17)
C12	0.0274 (15)	0.0389 (16)	0.060 (2)	0.0006 (12)	0.0140 (15)	0.0058 (14)
C13	0.0313 (15)	0.0369 (16)	0.0504 (19)	0.0021 (13)	0.0145 (14)	0.0007 (14)
C14	0.0333 (15)	0.0376 (16)	0.0442 (18)	−0.0038 (13)	0.0084 (14)	0.0019 (13)
C15	0.0421 (19)	0.053 (2)	0.052 (2)	0.0020 (15)	0.0136 (16)	0.0062 (16)
C16	0.054 (2)	0.059 (2)	0.051 (2)	0.0041 (18)	0.0129 (18)	0.0119 (17)
C17	0.061 (2)	0.068 (2)	0.046 (2)	−0.0066 (19)	0.0198 (18)	0.0068 (17)
C18	0.052 (2)	0.059 (2)	0.052 (2)	−0.0045 (17)	0.0257 (18)	−0.0023 (17)
C19	0.0378 (17)	0.0435 (18)	0.0429 (18)	−0.0063 (13)	0.0128 (14)	−0.0031 (14)
C20	0.0449 (19)	0.051 (2)	0.053 (2)	−0.0002 (16)	0.0191 (17)	−0.0008 (16)
C21	0.061 (3)	0.101 (3)	0.064 (3)	−0.027 (2)	0.022 (2)	−0.004 (2)
C22	0.056 (2)	0.062 (2)	0.080 (3)	0.0015 (18)	0.043 (2)	0.008 (2)

Fe1—O2	1.900 (2)	C7—C8	1.424 (5)
Fe1—O1	1.917 (2)	C8—C9	1.371 (5)
Fe1—N1	2.110 (3)	C8—H8	0.9300
Fe1—N2	2.152 (3)	C9—C10	1.391 (6)
Fe1—O3	2.164 (2)	C9—H9	0.9300
Fe1—Cl1	2.3566 (10)	C10—C11	1.361 (5)
Br1—C4	1.899 (3)	C10—H10	0.9300
O1—C12	1.317 (4)	C11—C12	1.425 (5)
O2—C19	1.312 (4)	C11—H11	0.9300
O3—C20	1.238 (4)	C13—C14	1.414 (5)
N1—C6	1.307 (4)	C13—H13	0.9300
N1—C1	1.416 (4)	C14—C15	1.412 (5)
N2—C13	1.304 (4)	C14—C19	1.441 (5)
N2—C2	1.409 (4)	C15—C16	1.367 (5)
N3—C20	1.306 (4)	C15—H15	0.9300
N3—C21	1.441 (5)	C16—C17	1.388 (6)
N3—C22	1.454 (5)	C16—H16	0.9300
N4—C1	1.332 (4)	C17—C18	1.373 (5)
N4—C5	1.334 (4)	C17—H17	0.9300
C1—C2	1.403 (4)	C18—C19	1.388 (5)
C2—C3	1.399 (4)	C18—H18	0.9300
C3—C4	1.370 (5)	C20—H20	0.9300
C3—H3	0.9300	C21—H21A	0.9600
C4—C5	1.378 (5)	C21—H21B	0.9600
C5—H5	0.9300	C21—H21C	0.9600
C6—C7	1.426 (5)	C22—H22A	0.9600
C6—H6	0.9300	C22—H22B	0.9600
C7—C12	1.404 (5)	C22—H22C	0.9600
O2—Fe1—O1	105.85 (10)	C9—C8—H8	119.5
O2—Fe1—N1	162.06 (10)	C7—C8—H8	119.5
O1—Fe1—N1	88.45 (10)	C8—C9—C10	119.1 (3)
O2—Fe1—N2	88.45 (10)	C8—C9—H9	120.5
O1—Fe1—N2	164.57 (11)	C10—C9—H9	120.5
N1—Fe1—N2	76.44 (10)	C11—C10—C9	121.9 (3)
O2—Fe1—O3	86.61 (10)	C11—C10—H10	119.1
O1—Fe1—O3	85.54 (10)	C9—C10—H10	119.1
N1—Fe1—O3	83.71 (10)	C10—C11—C12	120.5 (4)
N2—Fe1—O3	89.66 (10)	C10—C11—H11	119.7
O2—Fe1—Cl1	95.47 (8)	C12—C11—H11	119.7
O1—Fe1—Cl1	94.43 (8)	O1—C12—C7	124.0 (3)
N1—Fe1—Cl1	94.13 (8)	O1—C12—C11	117.8 (3)
N2—Fe1—Cl1	89.83 (7)	C7—C12—C11	118.2 (3)
O3—Fe1—Cl1	177.85 (8)	N2—C13—C14	126.8 (3)
C12—O1—Fe1	132.1 (2)	N2—C13—H13	116.6
C19—O2—Fe1	134.1 (2)	C14—C13—H13	116.6
C20—O3—Fe1	121.9 (2)	C15—C14—C13	117.3 (3)
C6—N1—C1	118.7 (3)	C15—C14—C19	118.3 (3)
C6—N1—Fe1	125.2 (2)	C13—C14—C19	124.4 (3)
C1—N1—Fe1	116.0 (2)	C16—C15—C14	121.7 (4)
C13—N2—C2	121.4 (3)	C16—C15—H15	119.2
C13—N2—Fe1	123.3 (2)	C14—C15—H15	119.2
C2—N2—Fe1	114.89 (19)	C15—C16—C17	119.3 (4)
C20—N3—C21	120.2 (3)	C15—C16—H16	120.4
C20—N3—C22	122.4 (3)	C17—C16—H16	120.4
C21—N3—C22	117.3 (3)	C18—C17—C16	121.1 (4)
C1—N4—C5	117.8 (3)	C18—C17—H17	119.5
N4—C1—C2	124.0 (3)	C16—C17—H17	119.5
N4—C1—N1	120.2 (3)	C17—C18—C19	121.5 (4)
C2—C1—N1	115.8 (3)	C17—C18—H18	119.2
C3—C2—C1	117.2 (3)	C19—C18—H18	119.2
C3—C2—N2	126.8 (3)	O2—C19—C18	119.8 (3)
C1—C2—N2	116.0 (3)	O2—C19—C14	122.1 (3)
C4—C3—C2	117.8 (3)	C18—C19—C14	118.1 (3)
C4—C3—H3	121.1	O3—C20—N3	124.8 (4)
C2—C3—H3	121.1	O3—C20—H20	117.6
C3—C4—C5	121.3 (3)	N3—C20—H20	117.6
C3—C4—Br1	120.0 (3)	N3—C21—H21A	109.5
C5—C4—Br1	118.7 (3)	N3—C21—H21B	109.5
N4—C5—C4	121.8 (3)	H21A—C21—H21B	109.5
N4—C5—H5	119.1	N3—C21—H21C	109.5
C4—C5—H5	119.1	H21A—C21—H21C	109.5
N1—C6—C7	125.2 (3)	H21B—C21—H21C	109.5
N1—C6—H6	117.4	N3—C22—H22A	109.5
C7—C6—H6	117.4	N3—C22—H22B	109.5
C12—C7—C8	119.4 (3)	H22A—C22—H22B	109.5
C12—C7—C6	124.3 (3)	N3—C22—H22C	109.5
C8—C7—C6	116.2 (3)	H22A—C22—H22C	109.5
C9—C8—C7	120.9 (4)	H22B—C22—H22C	109.5