Crystal structure of di-μ-methano­lato-bis­{[N′-(1-benzoyl­prop-1-en-2-yl)thio­phene-2-carbohydrazidato-κ3O,N′,O′]oxidovanadium(V)}

Carroccia, M.C.; Pesci, R.B.P.; Maia, P.I. da S.; Deflon, V.M.

doi:10.1107/S1600536814020327

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 10| October 2014| Pages m353-m354

doi:10.1107/S1600536814020327

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Crystal structure of di-μ-methanolato-bis{[N′-(1-benzoylprop-1-en-2-yl)thiophene-2-carbohydrazidato-κ³O,N′,O′]oxidovanadium(V)}

Murilo C. Carroccia,^a Rafaela B. P. Pesci,^a Pedro Ivo da S. Maia ^b and Victor M. Deflon ^a ^*

^aInstituto de Química de São Carlos, Universidade de São Paulo, 13560-970, São Carlos, SP, Brazil, and ^bDepartamento de Química, Universidade Federal do Triângulo Mineiro, 38025-440, Uberaba, MG, Brazil
^*Correspondence e-mail: deflon@iqsc.usp.br

Edited by M. Weil, Vienna University of Technology, Austria (Received 3 September 2014; accepted 9 September 2014; online 27 September 2014)

The neutral binuclear molecule of the title complex, [V₂(C₁₅H₁₂N₂O₂S)₂(CH₃O)₂O₂], exhibits inversion symmetry and consists of two oxidovanadium(V) (VO)³⁺ fragments, each coordinated by a dianionic and O,N′,O′-chelating N′-(1-benzoylprop-1-en-2-yl)thiophene-2-carbohydrazidate ligand. The V⁵⁺ cations are bridged by two asymmetrically bonding methanolate ligands [V—O = 1.8155 (12) and 2.3950 (13) Å] originating from the deprotonation of the methanol solvent. The coordination sphere of the V^V atom is distorted octahedral, with the equatorial plane defined by the three donor atoms of the thiophene-2-carbohydrazidate ligand and the O atom of a methanolate unit. The axial positions are occupied by the oxide group and the remaining methanolate ligand. The axially bound methanolate ligand shows a longer V—O bond length due to the trans influence caused by the tightly bonded oxide group. The packing of the complex molecules is dominated by dispersion forces.

Keywords: crystal structure; thiophene-2-carbohydrazide; vanadium(V) complex; dinuclear complex; alkoxide bridging.

CCDC reference: 1023545

1. Related literature

For related structures of binuclear vanadium(V) complexes with O,N,O-chelating hydrazonate ligands and methanolate bridges, see: Sarkar & Pal (2009 ); Monfared et al. (2011 ); Maia et al. (2005 , 2007 ). For synthetic details, see: Mondal et al. (2008 ).

2. Experimental

2.1. Crystal data

[V₂(C₁₅H₁₂N₂O₂S)₂(CH₃O)₂O₂]
M_r = 764.60
Monoclinic, P 2₁ /n
a = 10.9900 (2) Å
b = 15.9297 (3) Å
c = 11.0178 (3) Å
β = 119.884 (1)°
V = 1672.39 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.74 mm⁻¹
T = 296 K
0.21 × 0.21 × 0.10 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.860, T_max = 0.930
20108 measured reflections
3067 independent reflections
2718 reflections with I > 2σ(I)
R_int = 0.020

2.3. Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.083
S = 1.04
3067 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 1023545

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814020327/wm5059sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814020327/wm5059Isup2.hkl

checkCIF report

Related literature top

For related structures of binuclear vanadium(V) complexes with O,N,O-chelating hydrazonate ligands and methanolate bridges, see: Sarkar & Pal (2009); Monfared et al. (2011); Maia et al. (2005, 2007). For synthetic details, see: Mondal et al. (2008).

Experimental top

The synthesis of the complex was developed by a slight modification of the procedure previously described by Mondal et al. (2008). 0.2 mmol (0.053 g) of [VO(acac)₂] and 0.2 mmol of benzoylacetone-2-thinoylhydrazone (0.058 g) were diluted separately in methanol. The solutions were mixed and stirred for 0.5 h. A brown solution was obtained and after slow evaporation of the solvent single crystals were formed.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The binuclear molecular structure of the title compound with atom labels and displacement ellipsoids drawn at the 50% probability level. [Symmettry code: i) -x, -y+2, -z+1.]
	Fig. 2. Packing diagram of the title complex. No hydrogen-bonding interactions are observed.

Di-µ-methanolato-κ⁴O:O-bis{[N'-(1-benzoylprop-1-en-2-yl)thiophene-2-carbohydrazidato-κ³O,N',O']oxidovanadium(V)} top

Crystal data top

[V₂(C₁₅H₁₂N₂O₂S)₂(CH₃O)₂O₂]	F(000) = 784
M_r = 764.60	D_x = 1.518 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 451 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.9900 (2) Å	Cell parameters from 9900 reflections
b = 15.9297 (3) Å	θ = 2.5–25.4°
c = 11.0178 (3) Å	µ = 0.74 mm⁻¹
β = 119.884 (1)°	T = 296 K
V = 1672.39 (6) Å³	Prism, brown
Z = 2	0.21 × 0.21 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	3067 independent reflections
Radiation source: fine-focus sealed tube	2718 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
T_min = 0.860, T_max = 0.930	k = −19→19
20108 measured reflections	l = −10→13

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0427P)² + 0.7671P] where P = (F_o² + 2F_c²)/3
3067 reflections	(Δ/σ)_max = 0.001
219 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[V₂(C₁₅H₁₂N₂O₂S)₂(CH₃O)₂O₂]	V = 1672.39 (6) Å³
M_r = 764.60	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.9900 (2) Å	µ = 0.74 mm⁻¹
b = 15.9297 (3) Å	T = 296 K
c = 11.0178 (3) Å	0.21 × 0.21 × 0.10 mm
β = 119.884 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3067 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2718 reflections with I > 2σ(I)
T_min = 0.860, T_max = 0.930	R_int = 0.020
20108 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.04	Δρ_max = 0.27 e Å⁻³
3067 reflections	Δρ_min = −0.24 e Å⁻³
219 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
V	−0.01766 (3)	0.95609 (2)	0.63227 (3)	0.03545 (12)
S1	−0.33170 (6)	1.19868 (4)	0.71561 (6)	0.05580 (17)
O2	0.17270 (14)	0.93610 (9)	0.73088 (13)	0.0449 (3)
O3	−0.06694 (12)	0.93265 (8)	0.45226 (12)	0.0362 (3)
O4	−0.07281 (16)	0.87680 (9)	0.67733 (15)	0.0525 (4)
N2	0.02549 (16)	1.03306 (10)	0.80379 (16)	0.0382 (4)
N1	−0.08298 (17)	1.08675 (10)	0.78577 (17)	0.0426 (4)
C9	0.26550 (19)	0.93078 (12)	0.86578 (19)	0.0387 (4)
C8	0.2507 (2)	0.97723 (14)	0.9611 (2)	0.0463 (5)
H7	0.3208	0.9727	1.0544	0.056*
C6	0.1366 (2)	1.03221 (13)	0.9298 (2)	0.0417 (4)
C7	0.1447 (2)	1.08777 (15)	1.0428 (2)	0.0539 (5)
H2	0.2270	1.0740	1.1299	0.081*
H3	0.0628	1.0797	1.0515	0.081*
H1	0.1496	1.1453	1.0198	0.081*
C5	−0.1873 (2)	1.07576 (12)	0.6604 (2)	0.0389 (4)
O1	−0.18078 (14)	1.02693 (9)	0.56828 (14)	0.0436 (3)
C4	−0.3193 (2)	1.11904 (12)	0.6175 (2)	0.0404 (4)
C1	−0.5054 (3)	1.21073 (16)	0.6013 (3)	0.0607 (6)
H6	−0.5611	1.2508	0.6118	0.073*
C2	−0.5541 (2)	1.15642 (17)	0.4942 (3)	0.0603 (6)
H4	−0.6476	1.1540	0.4238	0.072*
C3	−0.4478 (2)	1.10288 (14)	0.4995 (2)	0.0473 (5)
H5	−0.4625	1.0625	0.4326	0.057*
C10	0.38325 (19)	0.87296 (12)	0.89970 (19)	0.0380 (4)
C15	0.4093 (2)	0.84603 (14)	0.7951 (2)	0.0473 (5)
H12	0.3543	0.8661	0.7043	0.057*
C14	0.5155 (2)	0.79008 (16)	0.8240 (2)	0.0586 (6)
H11	0.5325	0.7730	0.7532	0.070*
C13	0.5968 (2)	0.75917 (15)	0.9579 (2)	0.0552 (6)
H10	0.6685	0.7212	0.9773	0.066*
C12	0.5717 (2)	0.78462 (14)	1.0622 (2)	0.0506 (5)
H9	0.6258	0.7630	1.1520	0.061*
C11	0.4678 (2)	0.84163 (13)	1.03576 (19)	0.0453 (5)
H8	0.4534	0.8595	1.1079	0.054*
C16	−0.1838 (2)	0.88198 (14)	0.3600 (2)	0.0493 (5)
H15	−0.1841	0.8314	0.4072	0.074*
H13	−0.1768	0.8680	0.2789	0.074*
H14	−0.2692	0.9124	0.3317	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V	0.03501 (19)	0.0397 (2)	0.03146 (18)	0.00311 (13)	0.01640 (14)	−0.00117 (12)
S1	0.0529 (3)	0.0550 (3)	0.0687 (4)	0.0045 (3)	0.0372 (3)	−0.0054 (3)
O2	0.0387 (7)	0.0601 (9)	0.0324 (7)	0.0123 (6)	0.0151 (6)	0.0024 (6)
O3	0.0319 (7)	0.0404 (7)	0.0327 (6)	−0.0024 (5)	0.0133 (5)	−0.0056 (5)
O4	0.0642 (10)	0.0465 (8)	0.0544 (8)	−0.0015 (7)	0.0355 (8)	0.0020 (7)
N2	0.0374 (9)	0.0420 (9)	0.0391 (8)	0.0022 (7)	0.0220 (7)	−0.0014 (7)
N1	0.0407 (9)	0.0434 (9)	0.0484 (9)	0.0061 (7)	0.0258 (8)	−0.0007 (7)
C9	0.0328 (10)	0.0459 (11)	0.0339 (9)	0.0006 (8)	0.0141 (8)	0.0041 (8)
C8	0.0390 (11)	0.0566 (12)	0.0359 (10)	0.0057 (9)	0.0131 (8)	−0.0022 (9)
C6	0.0444 (11)	0.0468 (11)	0.0368 (10)	−0.0043 (9)	0.0224 (9)	−0.0040 (8)
C7	0.0558 (13)	0.0607 (14)	0.0454 (11)	−0.0017 (11)	0.0256 (10)	−0.0133 (10)
C5	0.0395 (10)	0.0371 (10)	0.0486 (11)	0.0018 (8)	0.0285 (9)	0.0045 (8)
O1	0.0362 (7)	0.0522 (8)	0.0435 (7)	0.0058 (6)	0.0207 (6)	−0.0018 (6)
C4	0.0411 (11)	0.0397 (10)	0.0504 (11)	0.0018 (8)	0.0304 (9)	0.0054 (8)
C1	0.0559 (14)	0.0571 (14)	0.0868 (17)	0.0149 (11)	0.0489 (14)	0.0092 (13)
C2	0.0365 (11)	0.0722 (16)	0.0692 (15)	0.0081 (11)	0.0242 (11)	0.0161 (13)
C3	0.0426 (11)	0.0502 (12)	0.0530 (11)	0.0017 (9)	0.0268 (10)	0.0031 (10)
C10	0.0314 (9)	0.0420 (10)	0.0370 (9)	−0.0013 (8)	0.0144 (8)	0.0006 (8)
C15	0.0434 (11)	0.0582 (13)	0.0381 (10)	0.0049 (10)	0.0186 (9)	0.0035 (9)
C14	0.0568 (14)	0.0690 (15)	0.0573 (13)	0.0109 (12)	0.0341 (11)	−0.0018 (11)
C13	0.0409 (12)	0.0560 (13)	0.0616 (13)	0.0113 (10)	0.0202 (10)	0.0004 (11)
C12	0.0414 (11)	0.0503 (12)	0.0429 (11)	0.0047 (9)	0.0079 (9)	0.0019 (9)
C11	0.0433 (11)	0.0535 (12)	0.0335 (9)	0.0052 (9)	0.0150 (8)	0.0005 (8)
C16	0.0420 (11)	0.0522 (12)	0.0445 (11)	−0.0140 (9)	0.0145 (9)	−0.0093 (9)

Geometric parameters (Å, º) top

V—O4	1.5839 (15)	C5—O1	1.308 (2)
V—O3	1.8155 (12)	C5—C4	1.456 (3)
V—O2	1.8421 (13)	C4—C3	1.386 (3)
V—O1	1.9300 (13)	C1—C2	1.341 (4)
V—N2	2.0992 (16)	C1—H6	0.9300
V—O3ⁱ	2.3950 (13)	C2—C3	1.425 (3)
S1—C1	1.695 (3)	C2—H4	0.9300
S1—C4	1.715 (2)	C3—H5	0.9300
O2—C9	1.321 (2)	C10—C15	1.387 (3)
O3—C16	1.426 (2)	C10—C11	1.404 (3)
O3—Vⁱ	2.3950 (13)	C15—C14	1.373 (3)
N2—C6	1.315 (3)	C15—H12	0.9300
N2—N1	1.399 (2)	C14—C13	1.380 (3)
N1—C5	1.295 (3)	C14—H11	0.9300
C9—C8	1.359 (3)	C13—C12	1.370 (3)
C9—C10	1.477 (3)	C13—H10	0.9300
C8—C6	1.424 (3)	C12—C11	1.372 (3)
C8—H7	0.9300	C12—H9	0.9300
C6—C7	1.494 (3)	C11—H8	0.9300
C7—H2	0.9600	C16—H15	0.9600
C7—H3	0.9600	C16—H13	0.9600
C7—H1	0.9600	C16—H14	0.9600

O4—V—O3	103.06 (7)	N1—C5—C4	119.43 (17)
O4—V—O2	100.18 (7)	O1—C5—C4	117.45 (17)
O3—V—O2	103.99 (6)	C5—O1—V	117.66 (12)
O4—V—O1	98.62 (7)	C3—C4—C5	126.90 (19)
O3—V—O1	90.23 (6)	C3—C4—S1	111.43 (15)
O2—V—O1	153.09 (7)	C5—C4—S1	121.67 (15)
O4—V—N2	97.68 (7)	C2—C1—S1	112.87 (18)
O3—V—N2	156.10 (6)	C2—C1—H6	123.6
O2—V—N2	83.64 (6)	S1—C1—H6	123.6
O1—V—N2	74.89 (6)	C1—C2—C3	113.0 (2)
O4—V—O3ⁱ	174.44 (6)	C1—C2—H4	123.5
O3—V—O3ⁱ	71.92 (6)	C3—C2—H4	123.5
O2—V—O3ⁱ	79.07 (6)	C4—C3—C2	111.0 (2)
O1—V—O3ⁱ	83.98 (5)	C4—C3—H5	124.5
N2—V—O3ⁱ	87.73 (5)	C2—C3—H5	124.5
C1—S1—C4	91.68 (11)	C15—C10—C11	118.46 (18)
C9—O2—V	133.45 (13)	C15—C10—C9	120.02 (17)
C16—O3—V	124.60 (12)	C11—C10—C9	121.48 (17)
C16—O3—Vⁱ	121.85 (11)	C14—C15—C10	120.71 (19)
V—O3—Vⁱ	108.08 (6)	C14—C15—H12	119.6
C6—N2—N1	115.69 (16)	C10—C15—H12	119.6
C6—N2—V	128.24 (13)	C15—C14—C13	120.2 (2)
N1—N2—V	115.79 (12)	C15—C14—H11	119.9
C5—N1—N2	107.93 (15)	C13—C14—H11	119.9
O2—C9—C8	120.78 (18)	C12—C13—C14	119.8 (2)
O2—C9—C10	114.37 (16)	C12—C13—H10	120.1
C8—C9—C10	124.84 (17)	C14—C13—H10	120.1
C9—C8—C6	125.28 (18)	C13—C12—C11	120.78 (19)
C9—C8—H7	117.4	C13—C12—H9	119.6
C6—C8—H7	117.4	C11—C12—H9	119.6
N2—C6—C8	120.30 (17)	C12—C11—C10	120.02 (19)
N2—C6—C7	120.84 (19)	C12—C11—H8	120.0
C8—C6—C7	118.85 (18)	C10—C11—H8	120.0
C6—C7—H2	109.5	O3—C16—H15	109.5
C6—C7—H3	109.5	O3—C16—H13	109.5
H2—C7—H3	109.5	H15—C16—H13	109.5
C6—C7—H1	109.5	O3—C16—H14	109.5
H2—C7—H1	109.5	H15—C16—H14	109.5
H3—C7—H1	109.5	H13—C16—H14	109.5
N1—C5—O1	123.12 (17)

O4—V—O2—C9	−63.04 (19)	C9—C8—C6—N2	9.1 (3)
O3—V—O2—C9	−169.38 (18)	C9—C8—C6—C7	−171.7 (2)
O1—V—O2—C9	70.6 (2)	N2—N1—C5—O1	−5.0 (2)
N2—V—O2—C9	33.66 (18)	N2—N1—C5—C4	174.88 (16)
O3ⁱ—V—O2—C9	122.57 (19)	N1—C5—O1—V	9.3 (2)
O4—V—O3—C16	28.39 (16)	C4—C5—O1—V	−170.54 (12)
O2—V—O3—C16	132.56 (15)	O4—V—O1—C5	88.96 (14)
O1—V—O3—C16	−70.51 (15)	O3—V—O1—C5	−167.79 (13)
N2—V—O3—C16	−121.15 (18)	O2—V—O1—C5	−45.0 (2)
O3ⁱ—V—O3—C16	−154.11 (17)	N2—V—O1—C5	−6.73 (13)
O4—V—O3—Vⁱ	−177.50 (7)	O3ⁱ—V—O1—C5	−96.00 (13)
O2—V—O3—Vⁱ	−73.33 (7)	N1—C5—C4—C3	−166.79 (19)
O1—V—O3—Vⁱ	83.59 (6)	O1—C5—C4—C3	13.1 (3)
N2—V—O3—Vⁱ	32.96 (16)	N1—C5—C4—S1	12.3 (3)
O3ⁱ—V—O3—Vⁱ	0.0	O1—C5—C4—S1	−167.85 (14)
O4—V—N2—C6	80.91 (18)	C1—S1—C4—C3	−0.08 (16)
O3—V—N2—C6	−128.97 (18)	C1—S1—C4—C5	−179.28 (17)
O2—V—N2—C6	−18.55 (17)	C4—S1—C1—C2	1.0 (2)
O1—V—N2—C6	177.82 (18)	S1—C1—C2—C3	−1.6 (3)
O3ⁱ—V—N2—C6	−97.81 (17)	C5—C4—C3—C2	178.37 (19)
O4—V—N2—N1	−92.68 (13)	S1—C4—C3—C2	−0.8 (2)
O3—V—N2—N1	57.4 (2)	C1—C2—C3—C4	1.5 (3)
O2—V—N2—N1	167.86 (13)	O2—C9—C10—C15	16.0 (3)
O1—V—N2—N1	4.23 (12)	C8—C9—C10—C15	−162.7 (2)
O3ⁱ—V—N2—N1	88.60 (12)	O2—C9—C10—C11	−161.71 (19)
C6—N2—N1—C5	−175.49 (17)	C8—C9—C10—C11	19.6 (3)
V—N2—N1—C5	−1.07 (19)	C11—C10—C15—C14	0.0 (3)
V—O2—C9—C8	−32.1 (3)	C9—C10—C15—C14	−177.8 (2)
V—O2—C9—C10	149.16 (14)	C10—C15—C14—C13	0.7 (4)
O2—C9—C8—C6	2.4 (3)	C15—C14—C13—C12	−0.2 (4)
C10—C9—C8—C6	−179.02 (19)	C14—C13—C12—C11	−1.0 (4)
N1—N2—C6—C8	177.40 (17)	C13—C12—C11—C10	1.7 (3)
V—N2—C6—C8	3.8 (3)	C15—C10—C11—C12	−1.1 (3)
N1—N2—C6—C7	−1.8 (3)	C9—C10—C11—C12	176.60 (19)
V—N2—C6—C7	−175.38 (15)

Symmetry code: (i) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[V₂(C₁₅H₁₂N₂O₂S)₂(CH₃O)₂O₂]
M_r	764.60
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.9900 (2), 15.9297 (3), 11.0178 (3)
β (°)	119.884 (1)
V (Å³)	1672.39 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.21 × 0.21 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.860, 0.930
No. of measured, independent and observed [I > 2σ(I)] reflections	20108, 3067, 2718
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.083, 1.04
No. of reflections	3067
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.24

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), WinGX (Farrugia, 2012).

Acknowledgements

The authors thank FAPESP (grant Nos. 2009/54011-8, 2011/16160-1 and 2011/16380-1), FAPEMIG, CNPq and CAPES for supporting this work.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Maia, P. I. S., Deflon, V. M., Sousa, G. F., Lemos, S. S., Batista, A. A., Nascimento, O. R. & Niquet, E. (2007). Z. Anorg. Allg. Chem. 633, 783–789. CAS Google Scholar
Maia, P. I. S., Deflon, V. M., Souza, E. J., Garcia, E., Souza, G. F., Batista, A. A., Figueiredo, A. T. & Niquet, E. (2005). Transition Met. Chem. 30, 404–410. Web of Science CSD CrossRef CAS Google Scholar
Mondal, B., Drew, M. G. B., Banerjee, R. & Ghosh, T. (2008). Polyhedron, 27, 3197–3206. Web of Science CSD CrossRef CAS Google Scholar
Monfared, H. H., Kheirabadi, S., Lalami, N. A. & Mayer, P. (2011). Polyhedron, 30, 1375–1384. Web of Science CSD CrossRef Google Scholar
Sarkar, A. & Pal, S. (2009). Inorg. Chim. Acta, 362, 3807–3812. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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