Bis(μ-methano­lato-κ2O:O)bis­{[4-bromo-N′-(1-methyl-3-oxidobut-2-en-1-yl­idene-κO)benzohydrazidato-κ2N′,O]oxido­vanadium(V)}

Wong, H.W.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536811021647

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m902

doi:10.1107/S1600536811021647

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Bis(μ-methanolato-κ²O:O)bis{[4-bromo-N′-(1-methyl-3-oxidobut-2-en-1-ylidene-κO)benzohydrazidato-κ²N′,O]oxidovanadium(V)}

Hon Wee Wong,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 30 May 2011; accepted 5 June 2011; online 11 June 2011)

The dinuclear compound, [V₂(C₁₂H₁₁BrN₂O₂)₂(CH₃O)₂O₂], lies on a center of inversion. The doubly-deprotonated Schiff base O,N,O′-chelates to the V^V atom; two metal atoms are bridged by the methoxide units. The coordination geometry is a distorted octahedron. Weak intermolecular C—H⋯N hydrogen bonding is present in the crystal structure. The bromophenyl unit is disordered over two positions, with the major component being in a 0.909 (6) proportion.

Related literature

For the isotypic compound that has chlorine in place of bromine, see: Sarkar & Pal (2009 ).

Experimental

Crystal data

[V₂(C₁₂H₁₁BrN₂O₂)₂(CH₃O)₂O₂]
M_r = 786.22
Monoclinic, P 2₁ /c
a = 8.7517 (5) Å
b = 12.3409 (7) Å
c = 13.9952 (8) Å
β = 101.8782 (7)°
V = 1479.17 (15) Å³
Z = 2
Mo Kα radiation
μ = 3.39 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.430, T_max = 0.551
18572 measured reflections
3400 independent reflections
3106 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.060
S = 0.99
3400 reflections
221 parameters
44 restraints
H-atom parameters constrained
Δρ_max = 0.96 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Selected bond lengths (Å)

V1—O1	1.9314 (13)
V1—O2	1.8607 (13)
V1—O3	1.5896 (14)
V1—O4	2.3459 (13)
V1—O4ⁱ	1.8289 (13)
V1—N2	2.0770 (15)
Symmetry code: (i) -x, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12C⋯N1ⁱⁱ	0.96	2.59	3.541 (5)	169
Symmetry code: (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811021647/xu5231sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021647/xu5231Isup2.hkl

checkCIF report

Comment top

A recent study detailed the crystal structure of [VO(C₁₂H₁₁ClN₂O₂)(CH₃O)]₂ (Sarkar & Pal, 2009). The title bromo analog (Scheme I) is isostructural, the two compounds crystallizing with matching cell dimensions. However, the title compound shows some disorder in the halophenyl portion (Fig. 1). Dinuclear [VO(C₁₂H₁₁BrN₂O₂)(CH₃O)]₂ lies on a center of inversion. The doubly-deprotonated Schiff base O,N,O'-chelates to the V^V atom; two metal centers are bridged by the methoxide unit. The geometry is an octahedron.

Related literature top

For the isotypic compound that has chlorine in place of bromine, see: Sarkar & Pal (2009).

Experimental top

Bis(acetylacetonato)oxovanadium (0.67 g, 2.5 mmol) was heated with 4-bromobenzoic acid hydrazide (0.54 g, 2.5 mmol) in methanol (50 ml) for 1 h. The solution mixture was then filtered and upon slow cooling of the filtrate, dark brown crystals separated out.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [VO(C₁₂H₁₁BrN₂O₂)(CH₃O)]₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in bromophenyl ring is not shown.

Bis(µ-methanolato-κ²O:O)bis{[4-bromo-N'-(1- methyl-3-oxidobut-2-en-1-ylidene-κO)benzohydrazidato- κ²N',O]oxidovanadium(V)} top

Crystal data top

[V₂(C₁₂H₁₁BrN₂O₂)₂(CH₃O)₂O₂]	F(000) = 784
M_r = 786.22	D_x = 1.765 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8361 reflections
a = 8.7517 (5) Å	θ = 2.2–28.2°
b = 12.3409 (7) Å	µ = 3.39 mm⁻¹
c = 13.9952 (8) Å	T = 100 K
β = 101.8782 (7)°	Prism, brown
V = 1479.17 (15) Å³	0.30 × 0.25 × 0.20 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	3400 independent reflections
Radiation source: fine-focus sealed tube	3106 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.430, T_max = 0.551	k = −16→16
18572 measured reflections	l = −18→18

Refinement top

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.060	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0308P)² + 1.3638P] where P = (F_o² + 2F_c²)/3
3400 reflections	(Δ/σ)_max = 0.001
221 parameters	Δρ_max = 0.96 e Å⁻³
44 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[V₂(C₁₂H₁₁BrN₂O₂)₂(CH₃O)₂O₂]	V = 1479.17 (15) Å³
M_r = 786.22	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.7517 (5) Å	µ = 3.39 mm⁻¹
b = 12.3409 (7) Å	T = 100 K
c = 13.9952 (8) Å	0.30 × 0.25 × 0.20 mm
β = 101.8782 (7)°

Data collection top

Bruker SMART APEX diffractometer	3400 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3106 reflections with I > 2σ(I)
T_min = 0.430, T_max = 0.551	R_int = 0.027
18572 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	44 restraints
wR(F²) = 0.060	H-atom parameters constrained
S = 0.99	Δρ_max = 0.96 e Å⁻³
3400 reflections	Δρ_min = −0.32 e Å⁻³
221 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	0.53762 (15)	0.29274 (14)	0.06235 (3)	0.0224 (2)	0.909 (6)
Br1'	0.5773 (11)	0.3313 (11)	0.0656 (3)	0.0164 (15)	0.091 (6)
V1	0.11414 (4)	0.60960 (2)	0.50419 (2)	0.01169 (8)
O1	0.21661 (15)	0.52544 (10)	0.41937 (9)	0.0152 (3)
O2	−0.04425 (16)	0.69868 (10)	0.52973 (9)	0.0149 (3)
O3	0.25986 (16)	0.67280 (11)	0.56588 (10)	0.0179 (3)
O4	−0.10415 (15)	0.51204 (10)	0.42270 (9)	0.0126 (2)
N1	0.15083 (18)	0.65573 (13)	0.30152 (11)	0.0142 (3)
N2	0.08999 (18)	0.70085 (12)	0.37726 (11)	0.0125 (3)
C1	0.4474 (2)	0.3788 (2)	0.14888 (15)	0.0186 (5)	0.909 (6)
C1'	0.4680 (11)	0.4032 (11)	0.1483 (7)	0.019*	0.091 (6)
C2	0.4295 (3)	0.3360 (2)	0.23695 (18)	0.0202 (6)	0.909 (6)
H2	0.4659	0.2650	0.2558	0.024*	0.909 (6)
C2'	0.455 (3)	0.3560 (15)	0.2361 (13)	0.020*	0.091 (6)
H2'	0.5014	0.2875	0.2544	0.024*	0.091 (6)
C3	0.3573 (3)	0.39817 (19)	0.29774 (18)	0.0181 (5)	0.909 (6)
H3	0.3448	0.3697	0.3587	0.022*	0.909 (6)
C3'	0.373 (3)	0.4097 (14)	0.2974 (13)	0.018*	0.091 (6)
H3'	0.3632	0.3780	0.3577	0.022*	0.091 (6)
C4	0.3030 (2)	0.50212 (18)	0.26988 (16)	0.0154 (4)	0.909 (6)
C4'	0.3054 (10)	0.5095 (9)	0.2697 (8)	0.015*	0.091 (6)
C5	0.3265 (4)	0.5453 (2)	0.18142 (19)	0.0177 (4)	0.909 (6)
H5	0.2927	0.6168	0.1628	0.021*	0.909 (6)
C5'	0.319 (3)	0.5568 (15)	0.1819 (13)	0.018*	0.091 (6)
H5'	0.2728	0.6254	0.1635	0.021*	0.091 (6)
C6	0.3994 (3)	0.4833 (2)	0.12096 (18)	0.0194 (5)	0.909 (6)
H6	0.4161	0.5122	0.0610	0.023*	0.909 (6)
C6'	0.401 (3)	0.5032 (15)	0.1208 (13)	0.019*	0.091 (6)
H6'	0.4110	0.5349	0.0606	0.023*	0.091 (6)
C7	0.2196 (2)	0.56521 (15)	0.33309 (13)	0.0136 (3)
C8	0.0615 (2)	0.86357 (16)	0.27592 (14)	0.0179 (4)
H8A	0.1688	0.8559	0.2664	0.027*
H8B	0.0386	0.9404	0.2839	0.027*
H8C	−0.0112	0.8345	0.2189	0.027*
C9	0.0435 (2)	0.80226 (14)	0.36548 (13)	0.0136 (3)
C10	−0.0241 (2)	0.85486 (15)	0.43769 (13)	0.0149 (4)
H10	−0.0407	0.9309	0.4319	0.018*
C11	−0.0663 (2)	0.80336 (14)	0.51441 (13)	0.0138 (3)
C12	−0.1443 (2)	0.85908 (15)	0.58647 (13)	0.0166 (4)
H12A	−0.2375	0.8183	0.5932	0.025*
H12B	−0.1745	0.9325	0.5635	0.025*
H12C	−0.0718	0.8629	0.6499	0.025*
C13	−0.2359 (2)	0.56198 (17)	0.36097 (15)	0.0209 (4)
H13A	−0.2989	0.5065	0.3209	0.031*
H13B	−0.1997	0.6151	0.3185	0.031*
H13C	−0.2994	0.5986	0.4013	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0193 (3)	0.0288 (5)	0.01969 (13)	0.0092 (3)	0.00564 (12)	−0.00508 (14)
Br1'	0.0125 (19)	0.018 (3)	0.0200 (12)	−0.001 (2)	0.0061 (10)	−0.0048 (12)
V1	0.01496 (16)	0.01018 (15)	0.01058 (15)	−0.00098 (11)	0.00417 (11)	0.00064 (11)
O1	0.0180 (6)	0.0146 (6)	0.0144 (6)	0.0015 (5)	0.0069 (5)	0.0018 (5)
O2	0.0203 (7)	0.0113 (6)	0.0148 (6)	−0.0004 (5)	0.0073 (5)	0.0003 (5)
O3	0.0210 (7)	0.0173 (7)	0.0152 (6)	−0.0046 (5)	0.0033 (5)	0.0012 (5)
O4	0.0145 (6)	0.0121 (6)	0.0114 (6)	0.0006 (5)	0.0030 (5)	0.0018 (5)
N1	0.0173 (8)	0.0144 (7)	0.0119 (7)	−0.0009 (6)	0.0056 (6)	−0.0015 (6)
N2	0.0140 (7)	0.0128 (7)	0.0114 (7)	−0.0009 (6)	0.0045 (6)	−0.0006 (6)
C1	0.0122 (9)	0.0263 (12)	0.0180 (10)	0.0034 (8)	0.0048 (8)	−0.0065 (9)
C2	0.0191 (13)	0.0208 (12)	0.0203 (10)	0.0059 (10)	0.0031 (9)	−0.0011 (9)
C3	0.0184 (12)	0.0198 (11)	0.0170 (10)	0.0021 (9)	0.0058 (8)	−0.0004 (8)
C4	0.0132 (9)	0.0176 (10)	0.0160 (9)	−0.0016 (8)	0.0046 (8)	−0.0020 (8)
C5	0.0184 (11)	0.0178 (11)	0.0180 (10)	0.0001 (9)	0.0061 (8)	−0.0006 (8)
C6	0.0174 (10)	0.0263 (13)	0.0160 (10)	0.0001 (10)	0.0067 (8)	−0.0012 (9)
C7	0.0131 (8)	0.0147 (8)	0.0135 (8)	−0.0036 (7)	0.0033 (7)	−0.0018 (7)
C8	0.0236 (10)	0.0159 (9)	0.0150 (9)	0.0020 (7)	0.0058 (7)	0.0037 (7)
C9	0.0126 (8)	0.0149 (9)	0.0130 (8)	−0.0012 (7)	0.0016 (7)	0.0010 (7)
C10	0.0189 (9)	0.0102 (8)	0.0154 (9)	0.0004 (7)	0.0033 (7)	−0.0002 (7)
C11	0.0141 (8)	0.0124 (8)	0.0142 (8)	0.0003 (6)	0.0011 (7)	−0.0023 (7)
C12	0.0204 (9)	0.0155 (9)	0.0146 (9)	0.0019 (7)	0.0053 (7)	−0.0020 (7)
C13	0.0184 (9)	0.0194 (10)	0.0218 (10)	0.0005 (7)	−0.0032 (8)	0.0065 (8)

Geometric parameters (Å, º) top

Br1—C1	1.9002 (19)	C3'—H3'	0.9500
Br1'—C1'	1.870 (8)	C4—C5	1.401 (3)
V1—O1	1.9314 (13)	C4—C7	1.479 (3)
V1—O2	1.8607 (13)	C4'—C5'	1.389 (9)
V1—O3	1.5896 (14)	C4'—C7	1.448 (8)
V1—O4	2.3459 (13)	C5—C6	1.389 (3)
V1—O4ⁱ	1.8289 (13)	C5—H5	0.9500
V1—N2	2.0770 (15)	C5'—C6'	1.390 (9)
O1—C7	1.309 (2)	C5'—H5'	0.9500
O2—C11	1.317 (2)	C6—H6	0.9500
O4—C13	1.430 (2)	C6'—H6'	0.9500
O4—V1ⁱ	1.8289 (13)	C8—C9	1.500 (2)
N1—C7	1.302 (2)	C8—H8A	0.9800
N1—N2	1.396 (2)	C8—H8B	0.9800
N2—C9	1.316 (2)	C8—H8C	0.9800
C1—C2	1.380 (3)	C9—C10	1.428 (3)
C1—C6	1.387 (3)	C10—C11	1.363 (3)
C1'—C6'	1.385 (9)	C10—H10	0.9500
C1'—C2'	1.386 (9)	C11—C12	1.496 (2)
C2—C3	1.391 (3)	C12—H12A	0.9800
C2—H2	0.9500	C12—H12B	0.9800
C2'—C3'	1.394 (9)	C12—H12C	0.9800
C2'—H2'	0.9500	C13—H13A	0.9800
C3—C4	1.395 (3)	C13—H13B	0.9800
C3—H3	0.9500	C13—H13C	0.9800
C3'—C4'	1.387 (9)

O3—V1—O4ⁱ	102.96 (6)	C3'—C4'—C7	119.7 (7)
O3—V1—O2	98.74 (7)	C5'—C4'—C7	119.6 (7)
O4ⁱ—V1—O2	104.72 (6)	C6—C5—C4	119.90 (19)
O3—V1—O1	100.11 (7)	C6—C5—H5	120.1
O4ⁱ—V1—O1	89.10 (6)	C4—C5—H5	120.1
O2—V1—O1	153.42 (6)	C4'—C5'—C6'	119.5 (6)
O3—V1—N2	97.33 (6)	C4'—C5'—H5'	120.2
O4ⁱ—V1—N2	156.26 (6)	C6'—C5'—H5'	120.2
O2—V1—N2	83.99 (6)	C1—C6—C5	119.38 (19)
O1—V1—N2	75.18 (6)	C1—C6—H6	120.3
O3—V1—O4	176.30 (6)	C5—C6—H6	120.3
O4ⁱ—V1—O4	73.91 (6)	C1'—C6'—C5'	119.7 (6)
O2—V1—O4	80.35 (5)	C1'—C6'—H6'	120.1
O1—V1—O4	81.95 (5)	C5'—C6'—H6'	120.1
N2—V1—O4	86.17 (5)	N1—C7—O1	122.62 (16)
C7—O1—V1	117.75 (12)	N1—C7—C4'	117.5 (5)
C11—O2—V1	129.67 (12)	O1—C7—C4'	119.9 (5)
C13—O4—V1ⁱ	124.48 (12)	N1—C7—C4	119.95 (17)
C13—O4—V1	123.17 (11)	O1—C7—C4	117.43 (17)
V1ⁱ—O4—V1	106.09 (6)	C9—C8—H8A	109.5
C7—N1—N2	107.84 (14)	C9—C8—H8B	109.5
C9—N2—N1	116.14 (15)	H8A—C8—H8B	109.5
C9—N2—V1	126.68 (12)	C9—C8—H8C	109.5
N1—N2—V1	116.45 (11)	H8A—C8—H8C	109.5
C2—C1—C6	121.62 (19)	H8B—C8—H8C	109.5
C2—C1—Br1	119.58 (16)	N2—C9—C10	120.41 (16)
C6—C1—Br1	118.79 (16)	N2—C9—C8	120.12 (17)
C6'—C1'—C2'	120.9 (6)	C10—C9—C8	119.48 (16)
C6'—C1'—Br1'	119.5 (6)	C11—C10—C9	124.39 (17)
C2'—C1'—Br1'	119.7 (6)	C11—C10—H10	117.8
C1—C2—C3	118.99 (19)	C9—C10—H10	117.8
C1—C2—H2	120.5	O2—C11—C10	122.07 (17)
C3—C2—H2	120.5	O2—C11—C12	114.39 (16)
C1'—C2'—C3'	119.5 (6)	C10—C11—C12	123.52 (17)
C1'—C2'—H2'	120.3	C11—C12—H12A	109.5
C3'—C2'—H2'	120.3	C11—C12—H12B	109.5
C2—C3—C4	120.53 (19)	H12A—C12—H12B	109.5
C2—C3—H3	119.7	C11—C12—H12C	109.5
C4—C3—H3	119.7	H12A—C12—H12C	109.5
C4'—C3'—C2'	119.6 (6)	H12B—C12—H12C	109.5
C4'—C3'—H3'	120.2	O4—C13—H13A	109.5
C2'—C3'—H3'	120.2	O4—C13—H13B	109.5
C3—C4—C5	119.52 (18)	H13A—C13—H13B	109.5
C3—C4—C7	119.89 (19)	O4—C13—H13C	109.5
C5—C4—C7	120.59 (19)	H13A—C13—H13C	109.5
C3'—C4'—C5'	120.7 (6)	H13B—C13—H13C	109.5

O3—V1—O1—C7	−94.55 (13)	C2'—C3'—C4'—C7	179.7 (4)
O4ⁱ—V1—O1—C7	162.44 (13)	C3—C4—C5—C6	1.9 (3)
O2—V1—O1—C7	40.0 (2)	C7—C4—C5—C6	−177.37 (19)
N2—V1—O1—C7	0.43 (12)	C3'—C4'—C5'—C6'	0.2 (9)
O4—V1—O1—C7	88.57 (13)	C7—C4'—C5'—C6'	−179.8 (6)
O3—V1—O2—C11	56.92 (16)	C2—C1—C6—C5	−2.2 (3)
O4ⁱ—V1—O2—C11	162.88 (15)	Br1—C1—C6—C5	176.95 (15)
O1—V1—O2—C11	−77.8 (2)	C4—C5—C6—C1	0.3 (3)
N2—V1—O2—C11	−39.60 (16)	C2'—C1'—C6'—C5'	−0.2 (7)
O4—V1—O2—C11	−126.72 (16)	Br1'—C1'—C6'—C5'	179.7 (5)
O4ⁱ—V1—O4—C13	153.18 (16)	C4'—C5'—C6'—C1'	0.0 (9)
O2—V1—O4—C13	44.67 (14)	N2—N1—C7—O1	4.5 (2)
O1—V1—O4—C13	−115.43 (14)	N2—N1—C7—C4'	−173.8 (4)
N2—V1—O4—C13	−39.87 (14)	N2—N1—C7—C4	−176.61 (16)
O4ⁱ—V1—O4—V1ⁱ	0.0	V1—O1—C7—N1	−3.1 (2)
O2—V1—O4—V1ⁱ	−108.51 (7)	V1—O1—C7—C4'	175.2 (4)
O1—V1—O4—V1ⁱ	91.39 (6)	V1—O1—C7—C4	177.94 (13)
N2—V1—O4—V1ⁱ	166.95 (7)	C3'—C4'—C7—N1	−176.1 (15)
C7—N1—N2—C9	167.03 (16)	C5'—C4'—C7—N1	3.8 (16)
C7—N1—N2—V1	−3.84 (18)	C3'—C4'—C7—O1	5.5 (16)
O3—V1—N2—C9	−69.23 (16)	C5'—C4'—C7—O1	−174.6 (15)
O4ⁱ—V1—N2—C9	142.13 (16)	C3'—C4'—C7—C4	−40 (8)
O2—V1—N2—C9	28.85 (16)	C5'—C4'—C7—C4	140 (8)
O1—V1—N2—C9	−167.80 (16)	C3—C4—C7—N1	−170.83 (19)
O4—V1—N2—C9	109.53 (15)	C5—C4—C7—N1	8.4 (3)
O3—V1—N2—N1	100.55 (13)	C3—C4—C7—O1	8.1 (3)
O4ⁱ—V1—N2—N1	−48.1 (2)	C5—C4—C7—O1	−172.6 (2)
O2—V1—N2—N1	−161.38 (13)	C3—C4—C7—C4'	144 (8)
O1—V1—N2—N1	1.97 (11)	C5—C4—C7—C4'	−37 (8)
O4—V1—N2—N1	−80.70 (12)	N1—N2—C9—C10	178.40 (16)
C6—C1—C2—C3	1.91 (17)	V1—N2—C9—C10	−11.8 (3)
Br1—C1—C2—C3	−177.28 (11)	N1—N2—C9—C8	−1.7 (2)
C6'—C1'—C2'—C3'	0.2 (3)	V1—N2—C9—C8	168.13 (13)
Br1'—C1'—C2'—C3'	−179.8 (2)	N2—C9—C10—C11	−9.9 (3)
C1—C2—C3—C4	0.34 (15)	C8—C9—C10—C11	170.21 (18)
C1'—C2'—C3'—C4'	0.0 (3)	V1—O2—C11—C10	32.7 (3)
C2—C3—C4—C5	−2.2 (2)	V1—O2—C11—C12	−148.61 (13)
C2—C3—C4—C7	177.03 (14)	C9—C10—C11—O2	1.7 (3)
C2'—C3'—C4'—C5'	−0.2 (7)	C9—C10—C11—C12	−176.86 (18)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···N1ⁱⁱ	0.96	2.59	3.541 (5)	169

Symmetry code: (ii) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[V₂(C₁₂H₁₁BrN₂O₂)₂(CH₃O)₂O₂]
M_r	786.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.7517 (5), 12.3409 (7), 13.9952 (8)
β (°)	101.8782 (7)
V (Å³)	1479.17 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.39
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.430, 0.551
No. of measured, independent and observed [I > 2σ(I)] reflections	18572, 3400, 3106
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.060, 0.99
No. of reflections	3400
No. of parameters	221
No. of restraints	44
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.96, −0.32

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

V1—O1	1.9314 (13)	V1—O4	2.3459 (13)
V1—O2	1.8607 (13)	V1—O4ⁱ	1.8289 (13)
V1—O3	1.5896 (14)	V1—N2	2.0770 (15)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···N1ⁱⁱ	0.96	2.59	3.541 (5)	169

Symmetry code: (ii) x, −y+3/2, z+1/2.

Acknowledgements

We thank the University of Malaya (RG020/09AFR) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sarkar, A. & Pal, S. (2009). Inorg. Chim. Acta, 362, 3807–3812. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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