{4-Bromo-2-[(5-chloro-2-oxidophen­yl)imino­methyl]­phenolato-κ3O,N,O′}(methanol-κO)(methano­lato-κO)­oxidovanadium(V)

Shahverdizadeh, G.H.; Ng, S.W.; Tiekink, E.R.T.; Mirtamizdoust, B.

doi:10.1107/S160053681200311X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages m221-m222

doi:10.1107/S160053681200311X

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{4-Bromo-2-[(5-chloro-2-oxidophenyl)iminomethyl]phenolato-κ³O,N,O′}(methanol-κO)(methanolato-κO)oxidovanadium(V)

Gholam Hossein Shahverdizadeh,^a ‡ Seik Weng Ng,^b,^c Edward R. T. Tiekink ^b ^* and Babak Mirtamizdoust ^d

^aDepartment of Chemistry, Faculty of Science, Tabriz Branch, Islamic Azad University, PO Box 1655, Tabriz, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, and ^dDepartment of Inorganic Chemistry, Faculty of Chemistry, University of Tabriz, PO Box 5166616471, Tabriz, Iran
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 24 January 2012; accepted 25 January 2012; online 31 January 2012)

The title Schiff base complex, [V(C₁₃H₇BrClNO₂)(CH₃O)O(CH₃OH)], features a vanadyl group, a tridentate Schiff base ligand, and coordinated methanol and methanolate ligands. The NO₅ donor set is based on a distorted octahedron. Helical supramolecular chains along [010] are found in the crystal structure mediated by O—H⋯O hydrogen bonds formed between the coordinating methanol molecule and the phenolate O atom of the chlorobenzene residue.

Related literature

For the structures of (E)-2-(2-hydroxybenzylideneamino)phenolates containing halide atoms on the aromatic ring(s), see: Yenişehirli et al. (2010 ). For related Schiff base vanadyl complexes containing alcohol and alkoxide ligands, see: Hartung et al. (2007 ); Clague et al. (1993 ). For the crystallization procedure, see: Harrowfield et al. (1996 ).

Experimental

Crystal data

[V(C₁₃H₇BrClNO₂)(CH₃O)O(CH₄O)]
M_r = 454.57
Monoclinic, P 2₁ /n
a = 9.9585 (2) Å
b = 9.8949 (2) Å
c = 17.3612 (3) Å
β = 100.746 (2)°
V = 1680.74 (6) Å³
Z = 4
Cu Kα radiation
μ = 9.42 mm⁻¹
T = 100 K
0.20 × 0.20 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.255, T_max = 0.834
6974 measured reflections
3453 independent reflections
3125 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.131
S = 1.04
3453 reflections
221 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.37 e Å⁻³
Δρ_min = −0.93 e Å⁻³

Table 1
Selected bond lengths (Å)

V—O1	1.872 (2)
V—O2	1.937 (2)
V—O3	2.266 (2)
V—O4	1.766 (2)
V—O5	1.596 (2)
V—N1	2.170 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.84 (1)	1.89 (2)	2.702 (3)	163 (5)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681200311X/hg5167sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681200311X/hg5167Isup2.hkl

checkCIF report

Comment top

Structural studies of complexes with (E)-2-(2-hydroxybenzylideneamino)phenolates containing halide atoms on the aromatic ring(s) are comparatively rare (Yenişehirli et al., 2010) and those of complexes containing the (E)-4-bromo-2-((5-chloro-2-hydroxyphenylimino)methyl)phenolate ligand have not been reported. Herein we report the oxo-vanadium(V) complex of this ligand, (I).

The V atom in (I) is coordinated by the O,N,O-tridentate Schiff base ligand, an oxido-O atom, an O atom of the methoxido ligand and an O atom of the methanol ligand. The resulting NO₅ donor set is based on an octahedron. The methanol ligand is trans to the oxido group and the V—O(methanol) bond length is significantly longer than the V—O(methanolate) bond, Table 1. The coordination geometry resembles those found in related V═O Schiff base compounds containing neutral and anionic forms of alcohols (Clague et al., 1993; Hartung et al., 2007).

The most prominent feature of the crystal packing is the formation of helical supramolecular chains along [010], Fig. 1 and Table 2. The connections between molecules are of the type O—H···O and involve the coordinated methanol molecule as the donor and the phenoxide-O atom of the chloro-substituted benzene ring as the acceptor.

Related literature top

For the structures of (E)-2-(2-hydroxybenzylideneamino)phenolates containing halide atoms on the aromatic ring(s), see: Yenişehirli et al. (2010). For related Schiff base vanadyl complexes containing alcohol and alkoxide ligands, see: Hartung et al. (2007); Clague et al. (1993). For the crystallization procedure, see: Harrowfield et al. (1996).

Experimental top

A solution of 4-chlorosalicylaldehyde (10 mmol) in EtOH (25 ml) was added drop-wise to a solution of 2-(aminomethyl)-4-bromophenol (10 mmol) in EtOH (15 ml). The mixture was refluxed for 5 h. The yellow precipitate was removed by filtration and recrystallized from MeOH solution. Then the ligand (0.8 mmol) was placed in one arm of a branched tube (Harrowfield et al., 1996) and oxovanadium(IV) bis(acetylacetonate) (0.8 mmol) placed in the other. Methanol was then added to fill both arms. The tube was sealed and the ligand-containing arm immersed in a bath at 333 K, while the other was left at ambient temperature. After two weeks, crystals were deposited in the arm held at ambient temperature. They were filtered off, washed with acetone and ether, and air-dried. Yield: 61%. M.pt.: 517 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the helical supramolecular chain along [010] in (I). The O—H···O hydrogen bonds are shown as orange dashed lines.

{2-[(5-Chloro-2-oxidophenyl)iminomethyl]-4-bromophenolato- κ³O,N,O'}(methanol-κO)(methanolato- κO)oxidovanadium(V) top

Crystal data top

[V(C₁₃H₇BrClNO₂)(CH₃O)O(CH₄O)]	F(000) = 904
M_r = 454.57	D_x = 1.796 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 3765 reflections
a = 9.9585 (2) Å	θ = 4.5–76.3°
b = 9.8949 (2) Å	µ = 9.42 mm⁻¹
c = 17.3612 (3) Å	T = 100 K
β = 100.746 (2)°	Plate, brown
V = 1680.74 (6) Å³	0.20 × 0.20 × 0.02 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3453 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3125 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.5°, θ_min = 4.8°
ω scan	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→12
T_min = 0.255, T_max = 0.834	l = −10→21
6974 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0869P)² + 1.3682P] where P = (F_o² + 2F_c²)/3
3453 reflections	(Δ/σ)_max = 0.001
221 parameters	Δρ_max = 1.37 e Å⁻³
1 restraint	Δρ_min = −0.93 e Å⁻³

Crystal data top

[V(C₁₃H₇BrClNO₂)(CH₃O)O(CH₄O)]	V = 1680.74 (6) Å³
M_r = 454.57	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 9.9585 (2) Å	µ = 9.42 mm⁻¹
b = 9.8949 (2) Å	T = 100 K
c = 17.3612 (3) Å	0.20 × 0.20 × 0.02 mm
β = 100.746 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3453 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3125 reflections with I > 2σ(I)
T_min = 0.255, T_max = 0.834	R_int = 0.029
6974 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	1 restraint
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 1.37 e Å⁻³
3453 reflections	Δρ_min = −0.93 e Å⁻³
221 parameters

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

	x	y	z	U_iso*/U_eq
Br	0.21340 (4)	0.40275 (4)	0.54299 (2)	0.03558 (16)
V	0.58605 (5)	1.02259 (5)	0.71783 (3)	0.01590 (16)
Cl	0.86189 (8)	1.03418 (8)	0.37755 (4)	0.02228 (19)
O1	0.4952 (2)	0.8625 (2)	0.73417 (12)	0.0202 (4)
O2	0.7315 (2)	1.1284 (2)	0.68762 (12)	0.0177 (4)
O3	0.7673 (2)	0.8869 (2)	0.76214 (13)	0.0194 (4)
H3	0.752 (5)	0.8057 (17)	0.771 (3)	0.041 (13)*
O4	0.6177 (2)	1.0892 (2)	0.81386 (13)	0.0211 (5)
O5	0.4594 (2)	1.1120 (2)	0.67670 (13)	0.0220 (5)
N1	0.6091 (3)	0.9280 (3)	0.60826 (15)	0.0169 (5)
C1	0.4304 (3)	0.7660 (3)	0.68900 (17)	0.0181 (6)
C2	0.3401 (3)	0.6813 (3)	0.72029 (19)	0.0216 (6)
H2	0.3230	0.6980	0.7715	0.026*
C3	0.2760 (3)	0.5739 (3)	0.6771 (2)	0.0234 (7)
H3A	0.2160	0.5164	0.6986	0.028*
C4	0.3008 (3)	0.5516 (3)	0.6017 (2)	0.0237 (7)
C5	0.3868 (3)	0.6329 (3)	0.56906 (19)	0.0218 (6)
H5	0.4016	0.6157	0.5175	0.026*
C6	0.4529 (3)	0.7419 (3)	0.61230 (18)	0.0191 (6)
C7	0.5457 (3)	0.8232 (3)	0.57644 (17)	0.0182 (6)
H7	0.5606	0.7972	0.5260	0.022*
C8	0.7007 (3)	1.0031 (3)	0.57077 (18)	0.0171 (6)
C9	0.7317 (3)	0.9777 (3)	0.49641 (17)	0.0172 (6)
H9	0.6910	0.9041	0.4654	0.021*
C10	0.8226 (3)	1.0625 (3)	0.46973 (17)	0.0189 (6)
C11	0.8838 (3)	1.1709 (3)	0.51455 (18)	0.0212 (6)
H11	0.9462	1.2277	0.4946	0.025*
C12	0.8540 (3)	1.1961 (3)	0.58772 (18)	0.0202 (6)
H12	0.8950	1.2701	0.6182	0.024*
C13	0.7623 (3)	1.1110 (3)	0.61637 (17)	0.0169 (6)
C14	0.8841 (3)	0.9337 (4)	0.8166 (2)	0.0259 (7)
H14A	0.9514	0.8607	0.8278	0.039*
H14B	0.8559	0.9619	0.8653	0.039*
H14C	0.9250	1.0107	0.7939	0.039*
C15	0.5543 (4)	1.2004 (4)	0.84499 (19)	0.0256 (7)
H15A	0.5968	1.2136	0.9001	0.038*
H15B	0.4567	1.1817	0.8412	0.038*
H15C	0.5660	1.2822	0.8152	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.0332 (2)	0.0270 (2)	0.0455 (3)	−0.01347 (15)	0.00452 (18)	−0.01039 (15)
V	0.0176 (3)	0.0136 (3)	0.0168 (3)	−0.00055 (19)	0.0040 (2)	−0.00131 (18)
Cl	0.0255 (4)	0.0234 (4)	0.0193 (4)	0.0001 (3)	0.0078 (3)	0.0003 (3)
O1	0.0231 (11)	0.0182 (10)	0.0201 (10)	−0.0041 (9)	0.0057 (8)	−0.0012 (8)
O2	0.0203 (10)	0.0146 (10)	0.0188 (10)	−0.0018 (8)	0.0051 (8)	−0.0001 (8)
O3	0.0208 (11)	0.0135 (10)	0.0228 (10)	−0.0017 (8)	0.0008 (8)	0.0025 (8)
O4	0.0231 (11)	0.0203 (11)	0.0209 (10)	−0.0001 (9)	0.0068 (8)	−0.0028 (8)
O5	0.0212 (11)	0.0203 (11)	0.0241 (11)	0.0011 (9)	0.0035 (9)	−0.0008 (8)
N1	0.0175 (12)	0.0151 (12)	0.0182 (11)	0.0005 (10)	0.0036 (9)	−0.0008 (9)
C1	0.0169 (13)	0.0140 (14)	0.0225 (14)	0.0021 (11)	0.0017 (11)	0.0013 (11)
C2	0.0185 (14)	0.0193 (15)	0.0276 (15)	−0.0004 (12)	0.0058 (12)	0.0011 (12)
C3	0.0174 (15)	0.0196 (15)	0.0334 (17)	−0.0030 (12)	0.0052 (12)	0.0026 (13)
C4	0.0184 (15)	0.0161 (14)	0.0338 (17)	−0.0032 (12)	−0.0025 (12)	−0.0014 (13)
C5	0.0213 (15)	0.0183 (15)	0.0244 (15)	0.0007 (12)	0.0006 (12)	−0.0023 (12)
C6	0.0179 (14)	0.0146 (14)	0.0242 (14)	−0.0001 (12)	0.0024 (11)	0.0018 (11)
C7	0.0198 (14)	0.0160 (14)	0.0190 (13)	0.0020 (12)	0.0039 (11)	0.0003 (11)
C8	0.0178 (14)	0.0132 (13)	0.0203 (14)	0.0002 (11)	0.0038 (11)	0.0005 (11)
C9	0.0203 (15)	0.0142 (14)	0.0171 (14)	0.0016 (11)	0.0031 (11)	−0.0001 (10)
C10	0.0197 (14)	0.0201 (15)	0.0167 (13)	0.0032 (12)	0.0031 (11)	−0.0003 (11)
C11	0.0220 (15)	0.0202 (15)	0.0219 (14)	−0.0014 (12)	0.0055 (11)	0.0040 (12)
C12	0.0205 (14)	0.0169 (14)	0.0224 (14)	−0.0014 (12)	0.0016 (11)	−0.0012 (11)
C13	0.0173 (14)	0.0148 (13)	0.0181 (13)	0.0023 (11)	0.0019 (11)	0.0012 (11)
C14	0.0204 (16)	0.0208 (15)	0.0322 (17)	−0.0014 (13)	−0.0063 (13)	0.0010 (13)
C15	0.0266 (16)	0.0259 (16)	0.0260 (15)	0.0014 (14)	0.0092 (13)	−0.0092 (13)

Geometric parameters (Å, º) top

Br—C4	1.906 (3)	C4—C5	1.372 (5)
V—O1	1.872 (2)	C5—C6	1.405 (4)
V—O2	1.937 (2)	C5—H5	0.9500
V—O3	2.266 (2)	C6—C7	1.451 (4)
V—O4	1.766 (2)	C7—H7	0.9500
V—O5	1.596 (2)	C8—C13	1.400 (4)
V—N1	2.170 (3)	C8—C9	1.405 (4)
Cl—C10	1.740 (3)	C9—C10	1.377 (4)
O1—C1	1.324 (4)	C9—H9	0.9500
O2—C13	1.340 (4)	C10—C11	1.397 (4)
O3—C14	1.433 (4)	C11—C12	1.380 (4)
O3—H3	0.835 (10)	C11—H11	0.9500
O4—C15	1.424 (4)	C12—C13	1.400 (4)
N1—C7	1.284 (4)	C12—H12	0.9500
N1—C8	1.425 (4)	C14—H14A	0.9800
C1—C6	1.411 (4)	C14—H14B	0.9800
C1—C2	1.411 (4)	C14—H14C	0.9800
C2—C3	1.385 (5)	C15—H15A	0.9800
C2—H2	0.9500	C15—H15B	0.9800
C3—C4	1.396 (5)	C15—H15C	0.9800
C3—H3A	0.9500

O5—V—O4	101.68 (11)	C6—C5—H5	120.1
O5—V—O1	99.96 (11)	C5—C6—C1	119.6 (3)
O4—V—O1	100.33 (10)	C5—C6—C7	118.0 (3)
O5—V—O2	98.49 (11)	C1—C6—C7	122.5 (3)
O4—V—O2	92.46 (10)	N1—C7—C6	124.4 (3)
O1—V—O2	154.86 (10)	N1—C7—H7	117.8
O5—V—N1	92.90 (11)	C6—C7—H7	117.8
O4—V—N1	163.59 (11)	C13—C8—C9	120.5 (3)
O1—V—N1	84.30 (10)	C13—C8—N1	112.9 (3)
O2—V—N1	77.84 (9)	C9—C8—N1	126.5 (3)
O5—V—O3	173.36 (10)	C10—C9—C8	118.1 (3)
O4—V—O3	84.85 (10)	C10—C9—H9	120.9
O1—V—O3	79.86 (9)	C8—C9—H9	120.9
O2—V—O3	79.85 (9)	C9—C10—C11	121.8 (3)
N1—V—O3	80.47 (9)	C9—C10—Cl	119.1 (2)
C1—O1—V	135.74 (19)	C11—C10—Cl	119.1 (2)
C13—O2—V	119.48 (19)	C12—C11—C10	120.3 (3)
C14—O3—V	122.00 (19)	C12—C11—H11	119.8
C14—O3—H3	110 (3)	C10—C11—H11	119.8
V—O3—H3	118 (4)	C11—C12—C13	119.0 (3)
C15—O4—V	129.3 (2)	C11—C12—H12	120.5
C7—N1—C8	122.0 (3)	C13—C12—H12	120.5
C7—N1—V	127.0 (2)	O2—C13—C12	121.8 (3)
C8—N1—V	110.89 (19)	O2—C13—C8	117.9 (3)
O1—C1—C6	122.4 (3)	C12—C13—C8	120.3 (3)
O1—C1—C2	118.4 (3)	O3—C14—H14A	109.5
C6—C1—C2	119.2 (3)	O3—C14—H14B	109.5
C3—C2—C1	120.7 (3)	H14A—C14—H14B	109.5
C3—C2—H2	119.7	O3—C14—H14C	109.5
C1—C2—H2	119.7	H14A—C14—H14C	109.5
C2—C3—C4	119.0 (3)	H14B—C14—H14C	109.5
C2—C3—H3A	120.5	O4—C15—H15A	109.5
C4—C3—H3A	120.5	O4—C15—H15B	109.5
C5—C4—C3	121.8 (3)	H15A—C15—H15B	109.5
C5—C4—Br	119.4 (3)	O4—C15—H15C	109.5
C3—C4—Br	118.8 (3)	H15A—C15—H15C	109.5
C4—C5—C6	119.7 (3)	H15B—C15—H15C	109.5
C4—C5—H5	120.1

O5—V—O1—C1	69.0 (3)	C2—C3—C4—C5	0.0 (5)
O4—V—O1—C1	172.9 (3)	C2—C3—C4—Br	179.5 (2)
O2—V—O1—C1	−67.7 (4)	C3—C4—C5—C6	0.2 (5)
N1—V—O1—C1	−23.0 (3)	Br—C4—C5—C6	−179.2 (2)
O3—V—O1—C1	−104.3 (3)	C4—C5—C6—C1	0.3 (5)
O5—V—O2—C13	−82.2 (2)	C4—C5—C6—C7	178.4 (3)
O4—V—O2—C13	175.6 (2)	O1—C1—C6—C5	176.3 (3)
O1—V—O2—C13	54.6 (3)	C2—C1—C6—C5	−1.0 (4)
N1—V—O2—C13	8.9 (2)	O1—C1—C6—C7	−1.7 (5)
O3—V—O2—C13	91.2 (2)	C2—C1—C6—C7	−179.1 (3)
O4—V—O3—C14	−36.8 (2)	C8—N1—C7—C6	179.1 (3)
O1—V—O3—C14	−138.3 (2)	V—N1—C7—C6	−5.0 (4)
O2—V—O3—C14	56.6 (2)	C5—C6—C7—N1	177.6 (3)
N1—V—O3—C14	135.9 (2)	C1—C6—C7—N1	−4.3 (5)
O5—V—O4—C15	−4.4 (3)	C7—N1—C8—C13	−178.1 (3)
O1—V—O4—C15	−106.9 (3)	V—N1—C8—C13	5.4 (3)
O2—V—O4—C15	94.8 (3)	C7—N1—C8—C9	1.7 (5)
N1—V—O4—C15	147.9 (4)	V—N1—C8—C9	−174.8 (3)
O3—V—O4—C15	174.4 (3)	C13—C8—C9—C10	−0.7 (5)
O5—V—N1—C7	−85.7 (3)	N1—C8—C9—C10	179.6 (3)
O4—V—N1—C7	121.4 (4)	C8—C9—C10—C11	0.2 (5)
O1—V—N1—C7	14.0 (3)	C8—C9—C10—Cl	−179.5 (2)
O2—V—N1—C7	176.2 (3)	C9—C10—C11—C12	0.0 (5)
O3—V—N1—C7	94.6 (3)	Cl—C10—C11—C12	179.7 (2)
O5—V—N1—C8	90.5 (2)	C10—C11—C12—C13	0.4 (5)
O4—V—N1—C8	−62.3 (4)	V—O2—C13—C12	171.7 (2)
O1—V—N1—C8	−169.7 (2)	V—O2—C13—C8	−8.8 (4)
O2—V—N1—C8	−7.54 (19)	C11—C12—C13—O2	178.6 (3)
O3—V—N1—C8	−89.1 (2)	C11—C12—C13—C8	−0.9 (5)
V—O1—C1—C6	21.3 (5)	C9—C8—C13—O2	−178.4 (3)
V—O1—C1—C2	−161.3 (2)	N1—C8—C13—O2	1.4 (4)
O1—C1—C2—C3	−176.2 (3)	C9—C8—C13—C12	1.0 (5)
C6—C1—C2—C3	1.3 (5)	N1—C8—C13—C12	−179.2 (3)
C1—C2—C3—C4	−0.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.84 (1)	1.89 (2)	2.702 (3)	163 (5)

Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[V(C₁₃H₇BrClNO₂)(CH₃O)O(CH₄O)]
M_r	454.57
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.9585 (2), 9.8949 (2), 17.3612 (3)
β (°)	100.746 (2)
V (Å³)	1680.74 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	9.42
Crystal size (mm)	0.20 × 0.20 × 0.02

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.255, 0.834
No. of measured, independent and observed [I > 2σ(I)] reflections	6974, 3453, 3125
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.131, 1.04
No. of reflections	3453
No. of parameters	221
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.37, −0.93

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

V—O1	1.872 (2)	V—O4	1.766 (2)
V—O2	1.937 (2)	V—O5	1.596 (2)
V—O3	2.266 (2)	V—N1	2.170 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.835 (10)	1.893 (18)	2.702 (3)	163 (5)

Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.

Footnotes

‡Additional correspondence author, e-mail: shahverdizadeh@iaut.ac.ir.

Acknowledgements

We gratefully acknowledge support of this study by Tabriz Azad University, and thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

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