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

In the title rhenium(I) complex, [ReBr(C(13)H(9)N(3)O)(CO)(3)]·CH(2)Cl(2), the dichloro-methane solvent mol-ecule is disordered over two positions with an occupancy ratio of 0.81 (15):0.19 (15). The Re(I) atom is coordinated by two N atoms from a 2-phenyl-5-(pyridin-2-yl-κN)-1,3,4-oxadiazole (L) ligand, three C atoms from three carbonyl groups and a Br atom in a distorted octa-hedral geometry. The three rings in L are almost coplanar (a mean plane fitted through all non-H atoms of this ligand has an r.m.s. deviation of 0.063 Å), and the carbonyl ligands are coordinated in a fac arrangement.

Related literature

For background to organic light emitting diodes, see: Li et al. (2005 ▶); Wong et al. (2005 ▶). For phospho­rescent materials, see: Kim et al. (2006 ▶); Lee et al. (2005 ▶); Bernhard et al. (2002 ▶). For the use of ReI complexes as phospho­rescent materials, see: Gong et al. (1998 ▶); Li et al. (2001 ▶); Rajendran et al. (2000 ▶); Zhang et al. (2009 ▶). For the synthetic procecure, see: Demko & Sharpless (2001 ▶).

Experimental

Crystal data

[ReBr(C13H9N3O)(CO)3]·CH2Cl2

M = 658.30

Monoclinic,

a = 12.492 (3) Å

b = 19.513 (4) Å

c = 16.835 (3) Å

β = 99.45 (3)°

V = 4047.9 (15) Å3

Z = 8

Mo Kα radiation

μ = 8.27 mm−1

T = 293 K

0.20 × 0.16 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.229, T max = 0.409

19615 measured reflections

4631 independent reflections

3992 reflections with I > 2σ(I)

R int = 0.104

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.107

S = 1.07

4631 reflections

276 parameters

36 restraints

H-atom parameters constrained

Δρmax = 2.88 e Å−3

Δρmin = −1.44 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052360/nk2078sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052360/nk2078Isup2.hkl

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

[ReBr(C13H9N3O)(CO)3]·CH2Cl2	F(000) = 2480
Mr = 658.30	Dx = 2.160 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4631 reflections
a = 12.492 (3) Å	θ = 2.3–27.5°
b = 19.513 (4) Å	µ = 8.27 mm−1
c = 16.835 (3) Å	T = 293 K
β = 99.45 (3)°	Block, yellow
V = 4047.9 (15) Å3	0.20 × 0.16 × 0.11 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	4631 independent reflections
Radiation source: fine-focus sealed tube	3992 reflections with I > 2σ(I)
graphite	Rint = 0.104
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→15
Tmin = 0.229, Tmax = 0.409	k = −25→25
19615 measured reflections	l = −21→21

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0507P)2 + 6.9046P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.002
4631 reflections	Δρmax = 2.88 e Å−3
276 parameters	Δρmin = −1.44 e Å−3
36 restraints	Extinction correction: SHELXS97(Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00089 (8)

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)
Re1	0.763878 (16)	0.394333 (9)	0.240070 (14)	0.03250 (12)
Br1	0.62778 (5)	0.40803 (3)	0.10476 (4)	0.04074 (16)
O1	0.9100 (4)	0.3751 (3)	0.4011 (3)	0.0696 (16)
O2	0.8889 (5)	0.2798 (3)	0.1726 (4)	0.0808 (18)
O3	0.6198 (4)	0.2847 (3)	0.2967 (4)	0.0825 (19)
O4	0.8670 (3)	0.59195 (17)	0.1890 (3)	0.0314 (8)
N1	0.6852 (3)	0.4871 (2)	0.2817 (3)	0.0314 (9)
N2	0.8475 (3)	0.4820 (2)	0.1993 (3)	0.0309 (9)
N3	0.9313 (3)	0.4917 (2)	0.1559 (3)	0.0335 (10)
C1	0.8579 (5)	0.3847 (3)	0.3391 (4)	0.0444 (15)
C2	0.8427 (5)	0.3231 (3)	0.1961 (5)	0.0508 (16)
C3	0.6735 (5)	0.3274 (4)	0.2764 (4)	0.0527 (16)
C4	0.6067 (4)	0.4881 (3)	0.3268 (4)	0.0384 (12)
H4	0.5784	0.4464	0.3403	0.046*
C5	0.5655 (5)	0.5467 (3)	0.3545 (4)	0.0468 (14)
H5	0.5123	0.5446	0.3871	0.056*
C6	0.6049 (5)	0.6097 (3)	0.3328 (4)	0.0445 (15)
H6	0.5779	0.6504	0.3505	0.053*
C7	0.6850 (5)	0.6109 (3)	0.2844 (4)	0.0396 (14)
H7	0.7113	0.6520	0.2673	0.047*
C8	0.7239 (4)	0.5490 (3)	0.2628 (3)	0.0308 (11)
C9	0.8113 (4)	0.5412 (2)	0.2168 (3)	0.0297 (10)
C10	0.9406 (4)	0.5585 (2)	0.1511 (3)	0.0304 (10)
C11	1.0160 (4)	0.5964 (2)	0.1110 (3)	0.0320 (11)
C12	1.0231 (5)	0.6674 (3)	0.1184 (4)	0.0441 (14)
H12	0.9795	0.6912	0.1487	0.053*
C13	1.0960 (5)	0.7015 (3)	0.0798 (5)	0.0534 (16)
H13	1.1024	0.7488	0.0849	0.064*
C14	1.1604 (5)	0.6663 (4)	0.0334 (4)	0.0516 (16)
H14	1.2089	0.6901	0.0073	0.062*
C15	1.1523 (5)	0.5966 (3)	0.0260 (4)	0.0442 (15)
H15	1.1948	0.5732	−0.0056	0.053*
C16	1.0816 (4)	0.5609 (3)	0.0651 (3)	0.0342 (11)
H16	1.0774	0.5134	0.0611	0.041*
Cl1	0.6313 (10)	0.7067 (5)	0.0785 (8)	0.115 (3)	0.810 (15)
Cl2	0.6782 (3)	0.57172 (14)	0.0268 (2)	0.0650 (12)	0.810 (15)
C17	0.6743 (17)	0.6573 (6)	0.0037 (9)	0.102 (5)	0.810 (15)
H17A	0.7460	0.6722	−0.0037	0.123*	0.810 (15)
H17B	0.6254	0.6644	−0.0466	0.123*	0.810 (15)
Cl1'	0.666 (5)	0.7100 (17)	0.087 (3)	0.121 (16)	0.190 (15)
Cl2'	0.715 (4)	0.591 (3)	0.0034 (16)	0.201 (18)	0.190 (15)
C17'	0.660 (9)	0.681 (3)	0.017 (5)	0.102 (5)	0.19
H17C	0.6951	0.7113	−0.0162	0.123*	0.190 (15)
H17D	0.5835	0.6799	−0.0067	0.123*	0.190 (15)

	U11	U22	U33	U12	U13	U23
Re1	0.03620 (16)	0.02314 (14)	0.0399 (2)	−0.00311 (6)	0.01139 (11)	0.00443 (7)
Br1	0.0422 (3)	0.0423 (3)	0.0395 (4)	0.0007 (2)	0.0119 (2)	−0.0024 (2)
O1	0.086 (3)	0.054 (3)	0.061 (4)	−0.020 (3)	−0.013 (3)	0.018 (3)
O2	0.089 (4)	0.043 (3)	0.115 (5)	0.024 (3)	0.032 (3)	−0.016 (3)
O3	0.079 (3)	0.072 (4)	0.100 (5)	−0.041 (3)	0.026 (3)	0.025 (3)
O4	0.0387 (18)	0.0246 (15)	0.034 (2)	−0.0016 (14)	0.0167 (16)	0.0007 (15)
N1	0.037 (2)	0.027 (2)	0.031 (2)	−0.0016 (16)	0.0096 (18)	0.0030 (18)
N2	0.0291 (19)	0.025 (2)	0.041 (3)	−0.0015 (16)	0.0141 (17)	0.0053 (18)
N3	0.033 (2)	0.026 (2)	0.043 (3)	0.0001 (16)	0.0143 (18)	0.0019 (19)
C1	0.046 (3)	0.028 (2)	0.058 (5)	−0.009 (2)	0.005 (3)	0.000 (3)
C2	0.055 (3)	0.035 (3)	0.065 (5)	−0.006 (3)	0.016 (3)	0.001 (3)
C3	0.054 (3)	0.055 (4)	0.050 (4)	−0.006 (3)	0.009 (3)	0.004 (3)
C4	0.038 (3)	0.042 (3)	0.037 (3)	−0.007 (2)	0.014 (2)	0.006 (2)
C5	0.046 (3)	0.056 (4)	0.042 (4)	−0.003 (3)	0.021 (3)	−0.003 (3)
C6	0.045 (3)	0.043 (3)	0.049 (4)	0.003 (2)	0.019 (3)	−0.009 (3)
C7	0.045 (3)	0.029 (3)	0.047 (4)	−0.001 (2)	0.015 (3)	−0.004 (2)
C8	0.032 (2)	0.029 (2)	0.033 (3)	−0.0020 (18)	0.011 (2)	0.0009 (19)
C9	0.038 (2)	0.022 (2)	0.030 (3)	−0.0014 (18)	0.009 (2)	0.0001 (19)
C10	0.033 (2)	0.029 (2)	0.031 (3)	−0.0012 (19)	0.008 (2)	−0.001 (2)
C11	0.039 (3)	0.028 (2)	0.032 (3)	−0.0015 (19)	0.012 (2)	0.001 (2)
C12	0.055 (3)	0.025 (2)	0.057 (4)	−0.001 (2)	0.023 (3)	0.004 (2)
C13	0.060 (4)	0.031 (3)	0.072 (5)	−0.013 (3)	0.018 (3)	0.004 (3)
C14	0.057 (3)	0.053 (4)	0.049 (4)	−0.014 (3)	0.021 (3)	0.010 (3)
C15	0.041 (3)	0.057 (4)	0.039 (4)	−0.005 (3)	0.020 (3)	−0.005 (3)
C16	0.043 (3)	0.030 (2)	0.032 (3)	−0.006 (2)	0.012 (2)	−0.004 (2)
Cl1	0.143 (5)	0.073 (4)	0.129 (7)	0.003 (3)	0.029 (5)	−0.024 (3)
Cl2	0.087 (2)	0.0521 (17)	0.053 (2)	−0.0020 (11)	0.0019 (14)	−0.0019 (11)
C17	0.209 (15)	0.038 (7)	0.074 (9)	0.007 (9)	0.064 (9)	0.010 (6)
Cl1'	0.24 (5)	0.034 (8)	0.084 (13)	−0.008 (15)	−0.01 (2)	−0.005 (8)
Cl2'	0.24 (3)	0.32 (4)	0.044 (12)	0.11 (3)	0.014 (16)	−0.036 (18)
C17'	0.209 (15)	0.038 (7)	0.074 (9)	0.007 (9)	0.064 (9)	0.010 (6)

Re1—C1	1.884 (7)	C7—H7	0.9300
Re1—C3	1.893 (7)	C8—C9	1.446 (7)
Re1—C2	1.920 (7)	C10—C11	1.448 (7)
Re1—N2	2.173 (4)	C11—C12	1.391 (7)
Re1—N1	2.228 (4)	C11—C16	1.399 (7)
Re1—Br1	2.6228 (11)	C12—C13	1.374 (9)
O1—C1	1.152 (8)	C12—H12	0.9300
O2—C2	1.132 (8)	C13—C14	1.392 (10)
O3—C3	1.157 (8)	C13—H13	0.9300
O4—C9	1.337 (6)	C14—C15	1.368 (9)
O4—C10	1.369 (6)	C14—H14	0.9300
N1—C4	1.335 (7)	C15—C16	1.375 (8)
N1—C8	1.357 (6)	C15—H15	0.9300
N2—C9	1.293 (6)	C16—H16	0.9300
N2—N3	1.385 (6)	Cl1—C17	1.739 (19)
N3—C10	1.314 (6)	Cl2—C17	1.713 (12)
C4—C5	1.367 (9)	C17—H17A	0.9700
C4—H4	0.9300	C17—H17B	0.9700
C5—C6	1.395 (8)	Cl1'—C17'	1.30 (9)
C5—H5	0.9300	Cl2'—C17'	1.90 (6)
C6—C7	1.391 (9)	C17'—H17C	0.9700
C6—H6	0.9300	C17'—H17D	0.9700
C7—C8	1.373 (7)
C1—Re1—C3	87.9 (3)	N1—C8—C9	111.2 (4)
C1—Re1—C2	89.1 (3)	C7—C8—C9	124.4 (5)
C3—Re1—C2	89.8 (3)	N2—C9—O4	111.2 (4)
C1—Re1—N2	95.5 (2)	N2—C9—C8	122.6 (4)
C3—Re1—N2	171.3 (2)	O4—C9—C8	126.2 (4)
C2—Re1—N2	98.3 (2)	N3—C10—O4	111.8 (4)
C1—Re1—N1	92.7 (2)	N3—C10—C11	127.4 (5)
C3—Re1—N1	98.1 (3)	O4—C10—C11	120.8 (4)
C2—Re1—N1	171.9 (2)	C12—C11—C16	120.5 (5)
N2—Re1—N1	73.71 (17)	C12—C11—C10	120.3 (5)
C1—Re1—Br1	178.2 (2)	C16—C11—C10	119.2 (4)
C3—Re1—Br1	90.9 (2)	C13—C12—C11	118.6 (6)
C2—Re1—Br1	92.2 (2)	C13—C12—H12	120.7
N2—Re1—Br1	85.55 (12)	C11—C12—H12	120.7
N1—Re1—Br1	86.19 (11)	C12—C13—C14	121.0 (6)
C9—O4—C10	103.8 (4)	C12—C13—H13	119.5
C4—N1—C8	116.3 (5)	C14—C13—H13	119.5
C4—N1—Re1	126.4 (4)	C15—C14—C13	120.0 (6)
C8—N1—Re1	117.2 (3)	C15—C14—H14	120.0
C9—N2—N3	108.7 (4)	C13—C14—H14	120.0
C9—N2—Re1	115.3 (3)	C14—C15—C16	120.3 (6)
N3—N2—Re1	135.9 (3)	C14—C15—H15	119.9
C10—N3—N2	104.5 (4)	C16—C15—H15	119.9
O1—C1—Re1	174.8 (6)	C15—C16—C11	119.6 (5)
O2—C2—Re1	177.5 (7)	C15—C16—H16	120.2
O3—C3—Re1	177.4 (7)	C11—C16—H16	120.2
N1—C4—C5	123.9 (5)	Cl1—C17—Cl2	112.2 (9)
N1—C4—H4	118.0	Cl1—C17—H17A	109.2
C5—C4—H4	118.0	Cl2—C17—H17A	109.2
C4—C5—C6	118.7 (6)	Cl1—C17—H17B	109.2
C4—C5—H5	120.6	Cl2—C17—H17B	109.2
C6—C5—H5	120.6	H17A—C17—H17B	107.9
C7—C6—C5	119.1 (5)	Cl1'—C17'—Cl2'	123 (5)
C7—C6—H6	120.5	Cl1'—C17'—H17C	106.7
C5—C6—H6	120.5	Cl2'—C17'—H17C	106.7
C8—C7—C6	117.4 (5)	Cl1'—C17'—H17D	106.7
C8—C7—H7	121.3	Cl2'—C17'—H17D	106.7
C6—C7—H7	121.3	H17C—C17'—H17D	106.6
N1—C8—C7	124.4 (5)
C1—Re1—N1—C4	−81.4 (5)	C8—N1—C4—C5	−0.4 (8)
C3—Re1—N1—C4	6.9 (5)	Re1—N1—C4—C5	176.1 (4)
C2—Re1—N1—C4	176.2 (15)	N1—C4—C5—C6	1.9 (10)
N2—Re1—N1—C4	−176.3 (5)	C4—C5—C6—C7	−0.5 (10)
Br1—Re1—N1—C4	97.2 (4)	C5—C6—C7—C8	−2.2 (10)
C1—Re1—N1—C8	95.2 (4)	C4—N1—C8—C7	−2.6 (8)
C3—Re1—N1—C8	−176.6 (4)	Re1—N1—C8—C7	−179.5 (4)
C2—Re1—N1—C8	−7.3 (18)	C4—N1—C8—C9	177.6 (5)
N2—Re1—N1—C8	0.2 (3)	Re1—N1—C8—C9	0.7 (6)
Br1—Re1—N1—C8	−86.3 (4)	C6—C7—C8—N1	3.9 (9)
C1—Re1—N2—C9	−92.4 (4)	C6—C7—C8—C9	−176.3 (6)
C3—Re1—N2—C9	20.2 (18)	N3—N2—C9—O4	−1.1 (6)
C2—Re1—N2—C9	177.7 (4)	Re1—N2—C9—O4	−179.6 (3)
N1—Re1—N2—C9	−1.2 (4)	N3—N2—C9—C8	−179.4 (5)
Br1—Re1—N2—C9	86.1 (4)	Re1—N2—C9—C8	2.2 (7)
C1—Re1—N2—N3	89.7 (5)	C10—O4—C9—N2	1.0 (6)
C3—Re1—N2—N3	−157.6 (15)	C10—O4—C9—C8	179.2 (5)
C2—Re1—N2—N3	−0.2 (6)	N1—C8—C9—N2	−1.9 (8)
N1—Re1—N2—N3	−179.1 (5)	C7—C8—C9—N2	178.3 (5)
Br1—Re1—N2—N3	−91.8 (5)	N1—C8—C9—O4	−179.9 (4)
C9—N2—N3—C10	0.8 (6)	C7—C8—C9—O4	0.3 (9)
Re1—N2—N3—C10	178.7 (4)	N2—N3—C10—O4	−0.1 (6)
C3—Re1—C1—O1	0(7)	N2—N3—C10—C11	−179.4 (5)
C2—Re1—C1—O1	−90 (7)	C9—O4—C10—N3	−0.5 (6)
N2—Re1—C1—O1	172 (7)	C9—O4—C10—C11	178.8 (5)
N1—Re1—C1—O1	98 (7)	N3—C10—C11—C12	−173.4 (6)
Br1—Re1—C1—O1	47 (11)	O4—C10—C11—C12	7.4 (8)
C1—Re1—C2—O2	47 (14)	N3—C10—C11—C16	6.4 (8)
C3—Re1—C2—O2	−41 (14)	O4—C10—C11—C16	−172.8 (5)
N2—Re1—C2—O2	142 (14)	C16—C11—C12—C13	−0.1 (9)
N1—Re1—C2—O2	150 (13)	C10—C11—C12—C13	179.6 (6)
Br1—Re1—C2—O2	−132 (14)	C11—C12—C13—C14	0.9 (10)
C1—Re1—C3—O3	−103 (14)	C12—C13—C14—C15	−0.5 (11)
C2—Re1—C3—O3	−13 (14)	C13—C14—C15—C16	−0.7 (10)
N2—Re1—C3—O3	144 (13)	C14—C15—C16—C11	1.5 (9)
N1—Re1—C3—O3	165 (14)	C12—C11—C16—C15	−1.1 (8)
Br1—Re1—C3—O3	79 (14)	C10—C11—C16—C15	179.1 (5)

Table 1

Selected bond lengths (Å)

Re1—C1	1.884 (7)
Re1—C3	1.893 (7)
Re1—C2	1.920 (7)
Re1—N2	2.173 (4)
Re1—N1	2.228 (4)
Re1—Br1	2.6228 (11)