Bromidotricarbon-yl[4-chloro-N-(2-pyridyl-methyl-idene)aniline-κN,N']rhenium(I).

In the title compound, [ReBr(C(12)H(9)ClN(2))(CO)(3)], the Re(I) atom has a distorted octa-hedral configuration with the three carbonyl ligands showing a facial arrangement. The main distortion of the octa-hedron is due to a small bite angle of the chelating bidentate diimine ligand [N-Re-N = 75.3 (3)°].

Related literature

For the synthesis of (4-chloro­phen­yl)pyridin-2-yl­methyl­ene­amine, see: Dehghanpour & Mahmoudi (2007 ▶). For related structures, see: Dehghanpour et al. (2009 ▶, 2010 ▶); Dehghanpour & Mahmoudi (2010 ▶)

Experimental

Crystal data

[ReBr(C12H9ClN2)(CO)3]

M = 566.80

Triclinic,

a = 8.6559 (8) Å

b = 8.9037 (8) Å

c = 10.9442 (9) Å

α = 75.691 (5)°

β = 83.001 (5)°

γ = 81.808 (5)°

V = 805.65 (12) Å3

Z = 2

Mo Kα radiation

μ = 10.20 mm−1

T = 150 K

0.10 × 0.09 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.425, T max = 0.734

8206 measured reflections

3651 independent reflections

2722 reflections with I > 2σ(I)

R int = 0.077

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.126

S = 1.03

3651 reflections

208 parameters

H-atom parameters constrained

Δρmax = 3.45 e Å−3

Δρmin = −2.54 e Å−3

Data collection: COLLECT (Nonius, 2002 ▶); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO–SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810044211/gk2300sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044211/gk2300Isup2.hkl

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

[ReBr(C12H9ClN2)(CO)3]	Z = 2
Mr = 566.80	F(000) = 528
Triclinic, P1	Dx = 2.336 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6559 (8) Å	Cell parameters from 8206 reflections
b = 8.9037 (8) Å	θ = 2.7–27.6°
c = 10.9442 (9) Å	µ = 10.20 mm−1
α = 75.691 (5)°	T = 150 K
β = 83.001 (5)°	Plate, orange
γ = 81.808 (5)°	0.10 × 0.09 × 0.03 mm
V = 805.65 (12) Å3

Nonius KappaCCD diffractometer	3651 independent reflections
Radiation source: fine-focus sealed tube	2722 reflections with I > 2σ(I)
graphite	Rint = 0.077
Detector resolution: 9 pixels mm-1	θmax = 27.6°, θmin = 2.7°
φ scans and ω scans with κ offsets	h = −11→11
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −11→11
Tmin = 0.425, Tmax = 0.734	l = −12→14
8206 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0437P)2 + 4.4525P] where P = (Fo2 + 2Fc2)/3
3651 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 3.45 e Å−3
0 restraints	Δρmin = −2.54 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
Re1	0.72202 (5)	0.92191 (4)	0.74692 (4)	0.03208 (15)
Br1	0.79387 (12)	0.78337 (11)	0.97638 (9)	0.0352 (2)
Cl1	1.3685 (3)	0.3425 (4)	0.5681 (3)	0.0536 (7)
O1	0.6432 (7)	1.0842 (8)	0.4811 (7)	0.0348 (16)
O2	0.6196 (9)	1.2317 (8)	0.8222 (7)	0.0454 (19)
O3	1.0512 (9)	1.0234 (8)	0.6675 (7)	0.0440 (18)
N1	0.5004 (9)	0.8272 (9)	0.8084 (7)	0.0324 (19)
N2	0.7661 (10)	0.6836 (9)	0.7214 (7)	0.0299 (18)
C1	0.6666 (12)	1.0207 (11)	0.5736 (11)	0.034 (2)
C2	0.6572 (11)	1.1172 (12)	0.7930 (9)	0.034 (2)
C3	0.9309 (13)	0.9829 (11)	0.6976 (9)	0.034 (2)
C4	0.3679 (12)	0.8976 (13)	0.8541 (9)	0.038 (2)
H4A	0.3654	1.0036	0.8574	0.045*
C5	0.2312 (12)	0.8245 (12)	0.8979 (9)	0.035 (2)
H5A	0.1401	0.8779	0.9327	0.042*
C6	0.2341 (12)	0.6726 (12)	0.8883 (9)	0.035 (2)
H6A	0.1433	0.6199	0.9141	0.042*
C7	0.3699 (12)	0.5983 (12)	0.8409 (10)	0.039 (2)
H7A	0.3730	0.4931	0.8354	0.046*
C8	0.5019 (12)	0.6742 (10)	0.8011 (9)	0.032 (2)
C9	0.6501 (11)	0.6024 (11)	0.7544 (9)	0.034 (2)
H9A	0.6616	0.4968	0.7481	0.041*
C10	0.9115 (12)	0.6014 (10)	0.6875 (9)	0.031 (2)
C11	1.0098 (12)	0.6759 (11)	0.5850 (9)	0.034 (2)
H11A	0.9797	0.7799	0.5405	0.041*
C12	1.1509 (13)	0.5960 (12)	0.5499 (10)	0.041 (3)
H12A	1.2183	0.6454	0.4811	0.050*
C13	1.1937 (12)	0.4441 (12)	0.6150 (9)	0.038 (2)
C14	1.1010 (13)	0.3726 (13)	0.7181 (10)	0.041 (3)
H14A	1.1341	0.2701	0.7641	0.049*
C15	0.9604 (12)	0.4498 (11)	0.7544 (9)	0.035 (2)
H15A	0.8961	0.4000	0.8252	0.043*

	U11	U22	U33	U12	U13	U23
Re1	0.0359 (3)	0.0276 (2)	0.0315 (2)	−0.00496 (16)	−0.00217 (17)	−0.00434 (16)
Br1	0.0400 (6)	0.0342 (5)	0.0299 (5)	−0.0039 (4)	−0.0040 (4)	−0.0047 (4)
Cl1	0.0439 (16)	0.0624 (18)	0.0549 (17)	0.0102 (14)	−0.0067 (14)	−0.0230 (15)
O1	0.022 (4)	0.037 (4)	0.047 (4)	−0.007 (3)	−0.003 (3)	−0.010 (4)
O2	0.056 (5)	0.031 (4)	0.050 (5)	−0.006 (4)	0.000 (4)	−0.014 (3)
O3	0.038 (4)	0.046 (4)	0.045 (4)	−0.010 (4)	−0.004 (4)	−0.002 (3)
N1	0.031 (4)	0.027 (4)	0.035 (4)	0.003 (3)	0.001 (4)	−0.005 (3)
N2	0.041 (5)	0.026 (4)	0.023 (4)	−0.003 (4)	−0.005 (4)	−0.006 (3)
C1	0.028 (5)	0.026 (5)	0.053 (7)	−0.008 (4)	0.011 (5)	−0.022 (5)
C2	0.022 (5)	0.039 (6)	0.038 (6)	0.000 (4)	−0.002 (4)	−0.007 (5)
C3	0.042 (6)	0.030 (5)	0.027 (5)	−0.001 (5)	0.000 (5)	−0.007 (4)
C4	0.030 (6)	0.046 (6)	0.038 (6)	0.000 (5)	−0.007 (5)	−0.014 (5)
C5	0.032 (6)	0.039 (6)	0.034 (5)	0.004 (4)	−0.008 (4)	−0.010 (4)
C6	0.032 (6)	0.044 (6)	0.028 (5)	−0.006 (5)	−0.003 (4)	−0.005 (4)
C7	0.037 (6)	0.035 (5)	0.045 (6)	−0.011 (5)	−0.014 (5)	−0.004 (5)
C8	0.043 (6)	0.022 (4)	0.033 (5)	−0.004 (4)	0.000 (5)	−0.008 (4)
C9	0.030 (5)	0.029 (5)	0.042 (6)	0.004 (4)	−0.009 (4)	−0.007 (4)
C10	0.041 (6)	0.023 (5)	0.035 (5)	−0.006 (4)	−0.004 (5)	−0.016 (4)
C11	0.044 (6)	0.026 (5)	0.032 (5)	−0.003 (4)	−0.003 (5)	−0.007 (4)
C12	0.046 (7)	0.038 (6)	0.039 (6)	−0.003 (5)	−0.001 (5)	−0.009 (5)
C13	0.039 (6)	0.045 (6)	0.033 (5)	0.004 (5)	−0.010 (5)	−0.017 (5)
C14	0.043 (6)	0.039 (6)	0.044 (6)	0.000 (5)	−0.009 (5)	−0.014 (5)
C15	0.043 (6)	0.031 (5)	0.034 (5)	−0.007 (5)	−0.002 (5)	−0.008 (4)

Re1—C2	1.919 (11)	C5—H5A	0.9500
Re1—C3	1.937 (10)	C6—C7	1.374 (14)
Re1—C1	1.969 (13)	C6—H6A	0.9500
Re1—N1	2.170 (8)	C7—C8	1.380 (13)
Re1—N2	2.182 (8)	C7—H7A	0.9500
Re1—Br1	2.6165 (11)	C8—C9	1.443 (13)
Cl1—C13	1.738 (11)	C9—H9A	0.9500
O1—C1	1.058 (12)	C10—C15	1.400 (13)
O2—C2	1.135 (12)	C10—C11	1.409 (13)
O3—C3	1.135 (11)	C11—C12	1.385 (14)
N1—C4	1.330 (12)	C11—H11A	0.9500
N1—C8	1.382 (11)	C12—C13	1.386 (14)
N2—C9	1.285 (12)	C12—H12A	0.9500
N2—C10	1.419 (12)	C13—C14	1.375 (14)
C4—C5	1.408 (13)	C14—C15	1.375 (14)
C4—H4A	0.9500	C14—H14A	0.9500
C5—C6	1.379 (14)	C15—H15A	0.9500
C2—Re1—C3	89.3 (4)	C7—C6—C5	119.2 (9)
C2—Re1—C1	89.3 (4)	C7—C6—H6A	120.4
C3—Re1—C1	89.0 (4)	C5—C6—H6A	120.4
C2—Re1—N1	96.0 (3)	C6—C7—C8	121.0 (9)
C3—Re1—N1	173.6 (3)	C6—C7—H7A	119.5
C1—Re1—N1	94.5 (3)	C8—C7—H7A	119.5
C2—Re1—N2	170.0 (3)	C7—C8—N1	120.6 (9)
C3—Re1—N2	99.1 (4)	C7—C8—C9	124.2 (9)
C1—Re1—N2	96.2 (3)	N1—C8—C9	115.2 (8)
N1—Re1—N2	75.3 (3)	N2—C9—C8	119.0 (9)
C2—Re1—Br1	92.1 (3)	N2—C9—H9A	120.5
C3—Re1—Br1	91.8 (3)	C8—C9—H9A	120.5
C1—Re1—Br1	178.4 (3)	C15—C10—C11	119.4 (9)
N1—Re1—Br1	84.6 (2)	C15—C10—N2	121.8 (8)
N2—Re1—Br1	82.3 (2)	C11—C10—N2	118.8 (8)
C4—N1—C8	117.7 (8)	C12—C11—C10	119.3 (9)
C4—N1—Re1	127.6 (7)	C12—C11—H11A	120.3
C8—N1—Re1	114.6 (6)	C10—C11—H11A	120.3
C9—N2—C10	115.7 (8)	C11—C12—C13	120.0 (9)
C9—N2—Re1	115.9 (7)	C11—C12—H12A	120.0
C10—N2—Re1	127.9 (6)	C13—C12—H12A	120.0
O1—C1—Re1	173.7 (9)	C14—C13—C12	121.0 (10)
O2—C2—Re1	178.9 (9)	C14—C13—Cl1	119.2 (8)
O3—C3—Re1	177.8 (9)	C12—C13—Cl1	119.9 (8)
N1—C4—C5	123.9 (10)	C15—C14—C13	119.9 (10)
N1—C4—H4A	118.1	C15—C14—H14A	120.0
C5—C4—H4A	118.1	C13—C14—H14A	120.0
C6—C5—C4	117.6 (10)	C14—C15—C10	120.4 (9)
C6—C5—H5A	121.2	C14—C15—H15A	119.8
C4—C5—H5A	121.2	C10—C15—H15A	119.8

Table 1

Selected bond lengths (Å)

Re1—C2	1.919 (11)
Re1—C3	1.937 (10)
Re1—C1	1.969 (13)
Re1—N1	2.170 (8)
Re1—N2	2.182 (8)
Re1—Br1	2.6165 (11)