Bromidotricarbon­yl[2-phenyl-5-(pyridin-2-yl-κN)-1,3,4-oxadiazole-κN4]rhenium(I) dichloro­methane monosolvate

Shi, L.-F.; Si, Z.-J.; Li, Y.-W.; Cao, H.-R.; Guan, Y.

doi:10.1107/S1600536810052360

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Pages m88-m89

https://doi.org/10.1107/S1600536810052360

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Bromidotricarbonyl[2-phenyl-5-(pyridin-2-yl-κN)-1,3,4-oxadiazole-κN⁴]rhenium(I) dichloromethane monosolvate

Lin-Fang Shi,^a ^* Zhen-Jun Si,^b Yan-Wei Li,^c Hua-Ru Cao ^a and Ying Guan ^a

^aCollege of Sciences, Zhejiang A&F University, Lin'an, Hangzhou, Zhejiang 311300, People's Republic of China, ^bSchool of Materials Science and Engineering, Changchun University of Science and Technology, Changchun 130000, People's Republic of China, and ^cSchool of Chemical Engineering & Technology, Harbin Institute of Technology, Harbin 150001, People's Republic of China
^*Correspondence e-mail: lfshi2003@163.com

(Received 29 November 2010; accepted 14 December 2010; online 18 December 2010)

In the title rhenium(I) complex, [ReBr(C₁₃H₉N₃O)(CO)₃]·CH₂Cl₂, the dichloromethane solvent molecule 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 octahedral 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 Re^I 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_r = 658.30
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.107
S = 1.07
4631 reflections
276 parameters
36 restraints
H-atom parameters constrained
Δρ_max = 2.88 e Å⁻³
Δρ_min = −1.44 e Å⁻³

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)

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810052360/nk2078Isup2.hkl

checkCIF report

Comment top

Interest in next generation displays and lighting technologies has stimulated research on organic light-emitting materials (Li et al., 2005; Wong et al., 2005), especially phosphorescent materials (Kim et al., 2006; Lee et al., 2005). As a result, transition metal phosphorescent complexes (Bernhard et al., 2002) have been studied intensively throughout the world. In order to further explore novel phosphorescent materials, several researchers paid attention to Re^I complexes (Gong et al., 1998; Li et al., 2001), of which the d⁶ electronic configuration is identical to that of the corresponding Os(II) and Ir(III) systems. Therefore, it is pressing to explore new Re^I complexes served as luminescent materials. In this article, we report the successful synthesis of a novel Re^I complex which contains the oxadiazole ligand of 2-phenyl-5-(pyridin-2-yl)-1,3,4-oxadiazole, and characterized its structure by single-crystal X-ray diffraction analysis. Its luminescent property will be further studied in the coming research.

The structure of complex [Re(CO)₃(L)Br].CH₂Cl₂, is shown in Figure 1. One molecule of solvent dichloromethane is present in the asymmetric unit. This was refined as disordered over two positions, with occupancies of 0.81 (15):0.19 (15).. The coordination geometry at the Re atom is a distorted octahedron with the three CO ligands arranged in a fac-fashion. The distances of C(1), C(2), and C(3) to Re(1) are 1.884 (7), 1.920 (7), and 1.893 (7)Å, respectively, and the Re—N bonds distances are 2.228 (4) and 2.173 (4)Å. The CO ligands are linearly coordinated for the bond angles of O—C—Re are 174.8 (6), 177.5 (7) and 177.4 (7)°, respectively, which are close to 180°. Furthermore, the bond angles between adjacent CO carbon atoms are 87.9 (3), 89.1 (3) and 89.8 (3)°, respectively, which are close to 90°, but the bond angle between the coordinated nitrogen atoms of ligand is 73.71 (17)°, which is much less than 90°. All other bond distances and angles are comparable to those found for the related Re^I complexes (Rajendran et al., 2000).

Furthermore, a kind of inter-molecular face-to-face stacking present in the molecular structure of [Re(CO)₃(L)Br].CH₂Cl₂: the 1,3,4-oxadiazole moiety in one molecule is almost parallel to the other one from another complex , and the approximate distance between the two closest atoms (N2—N3) is only 3.376°. Thus a bonded dual-molecule structure is constructed in the complex molecule which is believed a rigid one and will prevent geometric relaxation effectively (Zhang et al., 2009). Such rigid structure is promised possessing excellent luminescent properties.

Related literature top

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 Re^I 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 top

The oxadiazole ligand was synthesized as follows: 5-(2-pyridyl)tetrazole (Demko et al., 2001)(1.48 g, 10 mmol), pyridine (25 ml) and benzoyl chloride (1.41 g, 10 mmol) were added to a 50 ml round bottom flask and refluxed for 72 h. The crude product was then purified by column chromatography. Yield 1.61 g (59.6%). IR (KBr pellet): 3055 (w), 1616 (w), 1547 (s), 1481 (s), 1452 (vs), 1387 (s), 1146 (m), 1072 (m), 1024 (w), 793 (s), 715 (vs) cm-1. [Re(CO)₃(L)Br] was synthesized according to the following procedure: L (0.05 g, 0.210 mmol) and Re(CO)₅Br (0.08 g, 0.200 mmol) were refluxed in 15 ml of toluene for 6 h. After the mixture was cooled to RT, the solvent was removed in a water bath under reduced pressure. The resulting yellow solid was purified by silica gel column chromatography with acetic acid ethyl ester and dichloromethane (v/v = 10:1). Yellow single crystals of complexes 2 suitable for X-ray diffraction studies were grown from slow evaporation of a CH₂Cl₂ solution.

Structure description top

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 Re^I 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).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of [Re(CO)₃(L)Br].CH₂Cl₂, displacement ellipsoids are drawn at the 30% probability level. The disordered dichloromethane molecule is omitted. (arbitrary spheres for the H atoms).

Bromidotricarbonyl[2-phenyl-5-(pyridin-2-yl-κN)-1,3,4-oxadiazole- κN⁴]rhenium(I) dichloromethane monosolvate top

Crystal data top

[ReBr(C₁₃H₉N₃O)(CO)₃]·CH₂Cl₂	F(000) = 2480
M_r = 658.30	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0507P)² + 6.9046P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.002
4631 reflections	Δρ_max = 2.88 e Å⁻³
276 parameters	Δρ_min = −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)

Crystal data top

[ReBr(C₁₃H₉N₃O)(CO)₃]·CH₂Cl₂	V = 4047.9 (15) Å³
M_r = 658.30	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 12.492 (3) Å	µ = 8.27 mm⁻¹
b = 19.513 (4) Å	T = 293 K
c = 16.835 (3) Å	0.20 × 0.16 × 0.11 mm
β = 99.45 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4631 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3992 reflections with I > 2σ(I)
T_min = 0.229, T_max = 0.409	R_int = 0.104
19615 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	36 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.07	Δρ_max = 2.88 e Å⁻³
4631 reflections	Δρ_min = −1.44 e Å⁻³
276 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	[ReBr(C₁₃H₉N₃O)(CO)₃]·CH₂Cl₂
M_r	658.30
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	12.492 (3), 19.513 (4), 16.835 (3)
β (°)	99.45 (3)
V (Å³)	4047.9 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	8.27
Crystal size (mm)	0.20 × 0.16 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.229, 0.409
No. of measured, independent and observed [I > 2σ(I)] reflections	19615, 4631, 3992
R_int	0.104
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.107, 1.07
No. of reflections	4631
No. of parameters	276
No. of restraints	36
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.88, −1.44

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

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

Acknowledgements

This work was supported by the Zhejiang A & F University Science Foundation (2009FR068).

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