Bromidotricarbon-yl[2-(pyridin-2-yl-κN)-5-p-tolyl-1,3,4-oxadiazole-κN]rhenium(I) dichloro-methane monosolvate.

In the title compound, [ReBr(C(14)H(11)N(3)O)(CO)(3)]·CH(2)Cl(2), the coordination geometry of the Re(I) atom is a distorted ReC(3)N(2)Br octa-hedron with the carbonyl C atoms in a fac arrangement. Within the 2-(pyridin-2-yl)-5-p-tolyl-1,3,4-oxadiazole ligand, the dihedral angles between the oxadiazole ring and the pyridine (py) and benzene (bz) rings are 1.7 (2) and 7.1 (2)°, respectively, and the dihedral angle between the py and bz rings is 5.5 (2)°. In the crystal, aromatic π-π stacking between the oxadiazole rings of adjacent mol-ecules [centroid-centroid separation = 3.465 (3) Å] is seen.

Related literature

For backgroud to phospho­resence in Re(I) complexes, see: Ley et al. (1997 ▶); Zhang et al. (2009 ▶). For a related structure, see: Rajendran et al. (2000 ▶). For the synthesis of the ligand, see: Demko & Sharpless (2001 ▶); Tamoto et al. (1997 ▶).

Experimental

Crystal data

[ReBr(C14H11N3O)(CO)3]·CH2Cl2

M = 672.32

Monoclinic,

a = 12.590 (3) Å

b = 19.621 (4) Å

c = 17.660 (4) Å

β = 101.77 (3)°

V = 4270.8 (15) Å3

Z = 8

Mo Kα radiation

μ = 7.84 mm−1

T = 293 K

0.25 × 0.22 × 0.11 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002) ▶ T min = 0.149, T max = 0.409

20653 measured reflections

4847 independent reflections

4254 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.103

S = 1.05

4847 reflections

262 parameters

H-atom parameters constrained

Δρmax = 2.07 e Å−3

Δρmin = −2.88 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681004969X/hb5758sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004969X/hb5758Isup2.hkl

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

[ReBr(C14H11N3O)(CO)3]·CH2Cl2	F(000) = 2544
Mr = 672.32	Dx = 2.091 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4847 reflections
a = 12.590 (3) Å	θ = 3.1–24.8°
b = 19.621 (4) Å	µ = 7.84 mm−1
c = 17.660 (4) Å	T = 293 K
β = 101.77 (3)°	Block, yellow
V = 4270.8 (15) Å3	0.25 × 0.22 × 0.11 mm
Z = 8

Bruker SMART CCD diffractometer	4847 independent reflections
Radiation source: fine-focus sealed tube	4254 reflections with I > 2σ(I)
graphite	Rint = 0.063
phi and ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −14→16
Tmin = 0.149, Tmax = 0.409	k = −25→25
20653 measured reflections	l = −22→21

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0652P)2 + 4.556P] where P = (Fo2 + 2Fc2)/3
4847 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 2.07 e Å−3
0 restraints	Δρmin = −2.88 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
C1	0.3443 (5)	0.4519 (3)	0.2015 (4)	0.0487 (13)
C2	0.3684 (5)	0.3907 (2)	0.3391 (3)	0.0382 (11)
C3	0.1818 (5)	0.4511 (3)	0.2734 (3)	0.0489 (13)
C4	0.1120 (4)	0.2916 (3)	0.3248 (3)	0.0423 (12)
H4	0.0859	0.3334	0.3378	0.051*
C5	0.0700 (4)	0.2331 (3)	0.3493 (3)	0.0472 (13)
H5	0.0174	0.2355	0.3793	0.057*
C6	0.1068 (4)	0.1700 (3)	0.3287 (3)	0.0462 (12)
H6	0.0786	0.1298	0.3444	0.055*
C7	0.1858 (4)	0.1681 (3)	0.2847 (3)	0.0407 (11)
H7	0.2118	0.1269	0.2700	0.049*
C8	0.2249 (3)	0.2291 (3)	0.2634 (2)	0.0329 (10)
C9	0.3108 (4)	0.2358 (2)	0.2196 (2)	0.0301 (9)
C10	0.4329 (4)	0.2180 (2)	0.1553 (2)	0.0303 (9)
C11	0.5036 (4)	0.1774 (2)	0.1171 (2)	0.0312 (9)
C12	0.5080 (5)	0.1071 (3)	0.1248 (3)	0.0465 (13)
H12	0.4660	0.0851	0.1550	0.056*
C13	0.5751 (5)	0.0698 (3)	0.0873 (3)	0.0534 (14)
H13	0.5771	0.0226	0.0924	0.064*
C14	0.6396 (5)	0.1012 (3)	0.0422 (3)	0.0490 (14)
C15	0.6340 (4)	0.1714 (3)	0.0361 (3)	0.0436 (12)
H15	0.6765	0.1933	0.0062	0.052*
C16	0.5678 (4)	0.2104 (2)	0.0728 (3)	0.0356 (10)
H16	0.5662	0.2576	0.0679	0.043*
C17	0.7105 (7)	0.0591 (4)	0.0005 (4)	0.078 (2)
H17A	0.7491	0.0888	−0.0277	0.117*
H17B	0.6659	0.0285	−0.0348	0.117*
H17C	0.7614	0.0334	0.0375	0.117*
C18	0.1644 (7)	0.1149 (3)	0.0205 (5)	0.068 (2)
H18A	0.2392	0.1028	0.0209	0.082*
H18B	0.1226	0.1075	−0.0314	0.082*
N1	0.1910 (3)	0.2908 (2)	0.2820 (2)	0.0339 (8)
N2	0.3461 (3)	0.2940 (2)	0.2029 (2)	0.0327 (8)
N3	0.4270 (3)	0.2836 (2)	0.1605 (2)	0.0338 (8)
O1	0.3910 (5)	0.4950 (3)	0.1764 (3)	0.0831 (16)
O2	0.4232 (4)	0.3958 (2)	0.3981 (3)	0.0620 (12)
O3	0.1276 (5)	0.4934 (3)	0.2913 (3)	0.094 (2)
O4	0.3618 (3)	0.18424 (16)	0.19223 (18)	0.0326 (7)
Br1	0.12760 (5)	0.36874 (3)	0.11151 (3)	0.04326 (14)
Re1	0.268376 (15)	0.382313 (9)	0.241699 (11)	0.03283 (10)
Cl1	0.1140 (3)	0.06259 (12)	0.08553 (18)	0.1191 (10)
Cl2	0.15734 (14)	0.20035 (8)	0.04467 (9)	0.0578 (4)

	U11	U22	U33	U12	U13	U23
C1	0.058 (3)	0.034 (3)	0.056 (3)	0.000 (2)	0.015 (3)	−0.004 (2)
C2	0.046 (3)	0.026 (2)	0.040 (3)	0.0082 (19)	0.005 (2)	−0.0054 (18)
C3	0.049 (3)	0.046 (3)	0.051 (3)	0.009 (3)	0.009 (3)	−0.013 (2)
C4	0.037 (3)	0.056 (3)	0.037 (3)	0.008 (2)	0.014 (2)	−0.006 (2)
C5	0.046 (3)	0.058 (3)	0.041 (3)	−0.001 (2)	0.017 (2)	0.004 (2)
C6	0.045 (3)	0.048 (3)	0.049 (3)	−0.009 (2)	0.017 (2)	0.006 (2)
C7	0.046 (3)	0.036 (3)	0.043 (3)	−0.001 (2)	0.014 (2)	0.004 (2)
C8	0.036 (3)	0.034 (3)	0.030 (2)	0.0017 (17)	0.008 (2)	0.0021 (16)
C9	0.037 (2)	0.025 (2)	0.029 (2)	0.0035 (17)	0.0067 (18)	−0.0018 (16)
C10	0.036 (2)	0.030 (2)	0.026 (2)	0.0008 (18)	0.0081 (17)	0.0001 (15)
C11	0.041 (2)	0.029 (2)	0.025 (2)	0.0047 (18)	0.0100 (18)	−0.0011 (15)
C12	0.066 (4)	0.029 (3)	0.052 (3)	0.005 (2)	0.029 (3)	0.004 (2)
C13	0.076 (4)	0.032 (3)	0.057 (3)	0.014 (3)	0.025 (3)	−0.003 (2)
C14	0.059 (3)	0.053 (3)	0.040 (3)	0.017 (3)	0.023 (3)	−0.007 (2)
C15	0.048 (3)	0.052 (3)	0.035 (3)	0.007 (2)	0.019 (2)	0.005 (2)
C16	0.045 (3)	0.031 (2)	0.033 (2)	0.005 (2)	0.013 (2)	0.0034 (18)
C17	0.099 (5)	0.083 (5)	0.061 (4)	0.044 (4)	0.038 (4)	−0.010 (3)
C18	0.074 (5)	0.059 (4)	0.077 (5)	0.004 (3)	0.028 (4)	−0.018 (3)
N1	0.035 (2)	0.036 (2)	0.032 (2)	0.0047 (17)	0.0108 (17)	−0.0038 (16)
N2	0.034 (2)	0.031 (2)	0.035 (2)	0.0007 (16)	0.0111 (17)	−0.0032 (15)
N3	0.040 (2)	0.031 (2)	0.033 (2)	0.0015 (16)	0.0155 (17)	−0.0033 (15)
O1	0.093 (4)	0.054 (3)	0.105 (4)	−0.023 (3)	0.028 (3)	0.019 (3)
O2	0.065 (3)	0.059 (3)	0.054 (3)	0.013 (2)	−0.005 (2)	−0.014 (2)
O3	0.112 (5)	0.079 (4)	0.093 (4)	0.055 (4)	0.025 (3)	−0.022 (3)
O4	0.0407 (17)	0.0271 (16)	0.0328 (16)	0.0012 (13)	0.0144 (14)	−0.0017 (12)
Br1	0.0496 (3)	0.0390 (3)	0.0394 (3)	−0.0001 (2)	0.0049 (2)	0.00145 (19)
Re1	0.03905 (14)	0.02488 (12)	0.03580 (14)	0.00306 (6)	0.01052 (10)	−0.00546 (6)
Cl1	0.176 (3)	0.0556 (13)	0.142 (2)	0.0091 (15)	0.072 (2)	0.0206 (13)
Cl2	0.0680 (9)	0.0531 (9)	0.0511 (8)	0.0077 (7)	0.0089 (7)	0.0014 (6)

Re1—C1	1.887 (6)	C10—N3	1.293 (6)
Re1—C2	1.921 (5)	C10—O4	1.380 (5)
Re1—C3	1.890 (5)	C10—C11	1.459 (6)
Re1—N1	2.228 (4)	C11—C12	1.385 (6)
Re1—N2	2.169 (4)	C11—C16	1.395 (6)
Re1—Br1	2.6146 (11)	C12—C13	1.384 (7)
C1—O1	1.168 (7)	C12—H12	0.9300
C2—O2	1.131 (7)	C13—C14	1.392 (9)
C3—O3	1.159 (7)	C13—H13	0.9300
C4—N1	1.366 (6)	C14—C15	1.383 (8)
C4—C5	1.369 (8)	C14—C17	1.512 (7)
C4—H4	0.9300	C15—C16	1.386 (7)
C5—C6	1.397 (8)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.381 (7)	C17—H17A	0.9600
C6—H6	0.9300	C17—H17B	0.9600
C7—C8	1.374 (7)	C17—H17C	0.9600
C7—H7	0.9300	C18—Cl2	1.737 (6)
C8—N1	1.346 (6)	C18—Cl1	1.753 (8)
C8—C9	1.459 (7)	C18—H18A	0.9700
C9—N2	1.283 (6)	C18—H18B	0.9700
C9—O4	1.339 (5)	N2—N3	1.396 (5)
O1—C1—Re1	179.8 (7)	C15—C16—C11	118.5 (5)
O2—C2—Re1	176.8 (5)	C15—C16—H16	120.7
O3—C3—Re1	178.6 (6)	C11—C16—H16	120.7
N1—C4—C5	122.5 (5)	C14—C17—H17A	109.5
N1—C4—H4	118.8	C14—C17—H17B	109.5
C5—C4—H4	118.8	H17A—C17—H17B	109.5
C4—C5—C6	119.4 (5)	C14—C17—H17C	109.5
C4—C5—H5	120.3	H17A—C17—H17C	109.5
C6—C5—H5	120.3	H17B—C17—H17C	109.5
C7—C6—C5	119.0 (5)	Cl2—C18—Cl1	111.1 (4)
C7—C6—H6	120.5	Cl2—C18—H18A	109.4
C5—C6—H6	120.5	Cl1—C18—H18A	109.4
C8—C7—C6	118.1 (5)	Cl2—C18—H18B	109.4
C8—C7—H7	121.0	Cl1—C18—H18B	109.4
C6—C7—H7	121.0	H18A—C18—H18B	108.0
N1—C8—C7	124.5 (4)	C8—N1—C4	116.6 (4)
N1—C8—C9	110.8 (4)	C8—N1—Re1	117.8 (3)
C7—C8—C9	124.7 (4)	C4—N1—Re1	125.6 (4)
N2—C9—O4	112.1 (4)	C9—N2—N3	108.5 (4)
N2—C9—C8	122.1 (4)	C9—N2—Re1	116.1 (3)
O4—C9—C8	125.9 (4)	N3—N2—Re1	135.4 (3)
N3—C10—O4	113.1 (4)	C10—N3—N2	104.1 (4)
N3—C10—C11	128.8 (4)	C9—O4—C10	102.3 (3)
O4—C10—C11	118.2 (4)	C1—Re1—C3	87.8 (3)
C12—C11—C16	120.1 (4)	C1—Re1—C2	89.1 (3)
C12—C11—C10	121.0 (4)	C3—Re1—C2	89.2 (2)
C16—C11—C10	118.9 (4)	C1—Re1—N2	99.4 (2)
C13—C12—C11	119.7 (5)	C3—Re1—N2	171.4 (2)
C13—C12—H12	120.1	C2—Re1—N2	95.53 (18)
C11—C12—H12	120.1	C1—Re1—N1	172.65 (19)
C12—C13—C14	121.6 (5)	C3—Re1—N1	99.5 (2)
C12—C13—H13	119.2	C2—Re1—N1	91.87 (19)
C14—C13—H13	119.2	N2—Re1—N1	73.26 (16)
C15—C14—C13	117.3 (5)	C1—Re1—Br1	92.72 (19)
C15—C14—C17	122.1 (6)	C3—Re1—Br1	90.28 (18)
C13—C14—C17	120.6 (6)	C2—Re1—Br1	178.05 (17)
C14—C15—C16	122.7 (5)	N2—Re1—Br1	84.79 (11)
C14—C15—H15	118.6	N1—Re1—Br1	86.38 (10)
C16—C15—H15	118.6

Table 1

Selected bond lengths (Å)

Re1—C1	1.887 (6)
Re1—C2	1.921 (5)
Re1—C3	1.890 (5)
Re1—N1	2.228 (4)
Re1—N2	2.169 (4)
Re1—Br1	2.6146 (11)