(4-Methyl­benzohydrazidato-κ2N′,O)[2-(4-methyl­benzoyl­hydrazinyl­idene-κ2N,O)-3-phenyl­propionato(2−)]oxido­vanadium(V) methanol monosolvate

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

doi:10.1107/S1600536810011372

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page m481

doi:10.1107/S1600536810011372

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(4-Methylbenzohydrazidato-κ²N′,O)[2-(4-methylbenzoylhydrazinylidene-κ²N,O)-3-phenylpropionato(2−)]oxidovanadium(V) methanol monosolvate

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 25 March 2010; accepted 25 March 2010; online 31 March 2010)

The V^V atom in the title compound, [V(C₈H₉N₂O)(C₁₇H₁₄N₂O₃)O]·CH₃OH, is N,O-chelated by the benzoylhydrazidate anion and O,N,O′-chelated by the (benzoylhydrazono)propionate dianion. The octahedral trans-N₂O₄ coordination geometry is completed by the vanadyl O atom. Two mononuclear complexes and two solvent molecules are linked by O—H⋯O and O—H⋯N hydrogen bonds, generating a centrosymmetric aggregate.

Related literature

For (benzohydrazidato)[2-(benzoylhydrazono)propionato]oxidovanadium(V), see: Wong et al. (2009a ) and for (4-chlorobenzohydrazidato)[2-(4-chlorobenzoylhydrazono)propionato(2−)]oxidovanadium(V), see: Wong et al. (2009,b ).

Experimental

Crystal data

[V(C₈H₉N₂O)(C₁₇H₁₄N₂O₃)O]·CH₄O
M_r = 542.46
Triclinic, $[P \overline 1]$
a = 9.2770 (2) Å
b = 11.2558 (2) Å
c = 13.4691 (3) Å
α = 95.769 (2)°
β = 96.708 (2)°
γ = 109.675 (2)°
V = 1300.48 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 293 K
0.35 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.864, T_max = 0.919
12503 measured reflections
5956 independent reflections
3843 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.167
S = 1.03
5956 reflections
337 parameters
13 restraints
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯O4ⁱ	0.84	2.18	2.821 (5)	133
N1—H1⋯O3ⁱ	0.86	2.13	2.808 (3)	135
N2—H2⋯O6	0.86	1.99	2.800 (4)	156
Symmetry code: (i) -x+1, -y+1, -z+1.

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/S1600536810011372/bt5227sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810011372/bt5227Isup2.hkl

checkCIF report

Comment top

The reaction of vanadyl(IV) sulfate and the Schiff base that is synthesized by condensing a substituted benzhydrazine and a substituted pyruvic acid leads a vanadium(V) derivative of the Schiff base. However, another mole of the Schiff base is cleaved and the resulting benzhydrazine monoanion also chelates to the metal atom (Wong et al., 2009a, 2009b). A similar product is isolated in the present study on the reaction of the Schiff base, 2-[p-methylbenzoylhydrazono]-3-phenylpropionic acid so that the metal atom is chelated by two different ligands. The mononuclear mixed-ligand compound crystallizes as a monosolvate (Scheme I, Fig. 1). The vanadium(V) atom is N,O-chelated by the benzoylhydrazidate anion and O,N,O'-chelated by the (benzoylhydrazono)propionate dianion; the terdentate chelate binds in a meridional mode. The octahedral trans-N₂O₄ coordination geometry is completed by the vanadyl O atom. Two mononuclear complexes and two solvent molecules are linked by hydrogen bonds to generate a centrosymmetric aggregate.

Related literature top

For (benzohydrazidato)[2-(benzoylhydrazono)propionato]oxidovanadium(V), see: Wong et al. (2009a,b).

Experimental top

2-[p-Methylbenzoylhydrazono]-3-phenylpropionic acid prepared from the condensation reaction of p-methylbenzhydrazide and 3-phenylpyruvic acid. The compound (0.85 g, 3 mmol) and vanadyl sulfate (1.25 g, 1.5 mmol) in 50 ml of 95% ethanol for 5 hours. Slow evaporation of the filtrate gave orange crystals. The presence of methanol in the crystal structure is attributed to the methanol present in the techical grade solvent.

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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound with ellipsoids at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

(4-Methylbenzohydrazidato-κ²N',O)[2-(4- methylbenzoylhydrazinylidene-κ²N,O)-3- phenylpropionato(2-)]oxidovanadium(V) methanol monosolvate top

Crystal data top

[V(C₈H₉N₂O)(C₁₇H₁₄N₂O₃)O]·CH₄O	Z = 2
M_r = 542.46	F(000) = 564
Triclinic, P1	D_x = 1.385 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2770 (2) Å	Cell parameters from 2688 reflections
b = 11.2558 (2) Å	θ = 2.5–22.6°
c = 13.4691 (3) Å	µ = 0.43 mm⁻¹
α = 95.769 (2)°	T = 293 K
β = 96.708 (2)°	Block, orange
γ = 109.675 (2)°	0.35 × 0.20 × 0.20 mm
V = 1300.48 (5) Å³

Data collection top

Bruker SMART APEX diffractometer	5956 independent reflections
Radiation source: fine-focus sealed tube	3843 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 27.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
T_min = 0.864, T_max = 0.919	k = −14→14
12503 measured reflections	l = −17→17

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0856P)² + 0.2209P] where P = (F_o² + 2F_c²)/3
5956 reflections	(Δ/σ)_max = 0.001
337 parameters	Δρ_max = 0.55 e Å⁻³
13 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[V(C₈H₉N₂O)(C₁₇H₁₄N₂O₃)O]·CH₄O	γ = 109.675 (2)°
M_r = 542.46	V = 1300.48 (5) Å³
Triclinic, P1	Z = 2
a = 9.2770 (2) Å	Mo Kα radiation
b = 11.2558 (2) Å	µ = 0.43 mm⁻¹
c = 13.4691 (3) Å	T = 293 K
α = 95.769 (2)°	0.35 × 0.20 × 0.20 mm
β = 96.708 (2)°

Data collection top

Bruker SMART APEX diffractometer	5956 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3843 reflections with I > 2σ(I)
T_min = 0.864, T_max = 0.919	R_int = 0.028
12503 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	13 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.03	Δρ_max = 0.55 e Å⁻³
5956 reflections	Δρ_min = −0.48 e Å⁻³
337 parameters

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

	x	y	z	U_iso*/U_eq
V1	0.51795 (6)	0.51791 (5)	0.29034 (4)	0.04766 (18)
O1	0.6537 (2)	0.40109 (19)	0.34261 (14)	0.0526 (5)
O2	0.6733 (2)	0.57531 (19)	0.20087 (15)	0.0542 (5)
O3	0.3375 (2)	0.3810 (2)	0.32493 (15)	0.0557 (5)
O4	0.1695 (3)	0.1820 (2)	0.28159 (19)	0.0734 (7)
O5	0.4366 (3)	0.6198 (2)	0.27738 (17)	0.0633 (6)
O6	0.6859 (6)	0.8379 (3)	0.5277 (3)	0.1379 (14)
H6	0.7610	0.8725	0.5749	0.207*
N1	0.7041 (3)	0.5407 (2)	0.47916 (18)	0.0493 (6)
H1	0.7457	0.5723	0.5409	0.059*
N2	0.6198 (3)	0.5937 (2)	0.42177 (18)	0.0498 (6)
H2	0.6126	0.6646	0.4464	0.060*
N3	0.5391 (3)	0.3913 (2)	0.08943 (17)	0.0475 (6)
N4	0.4523 (3)	0.3744 (2)	0.16640 (17)	0.0450 (5)
C1	0.7176 (3)	0.4347 (3)	0.4322 (2)	0.0466 (7)
C2	0.8042 (3)	0.3663 (3)	0.4855 (2)	0.0480 (7)
C3	0.8251 (4)	0.2638 (3)	0.4316 (3)	0.0645 (9)
H3A	0.7844	0.2400	0.3632	0.077*
C4	0.9055 (5)	0.1970 (4)	0.4783 (3)	0.0740 (10)
H4	0.9209	0.1299	0.4402	0.089*
C5	0.9646 (4)	0.2264 (3)	0.5806 (3)	0.0578 (8)
C6	0.9450 (4)	0.3295 (3)	0.6338 (3)	0.0631 (9)
H6A	0.9854	0.3528	0.7023	0.076*
C7	0.8662 (4)	0.3989 (3)	0.5873 (2)	0.0597 (8)
H7	0.8547	0.4683	0.6248	0.072*
C8	1.0483 (4)	0.1494 (4)	0.6323 (3)	0.0776 (11)
H8A	1.1188	0.2018	0.6908	0.116*
H8B	1.1051	0.1202	0.5863	0.116*
H8C	0.9740	0.0772	0.6528	0.116*
C9	0.7612 (3)	0.5454 (3)	0.0442 (2)	0.0487 (7)
C10	0.8704 (4)	0.6676 (3)	0.0614 (3)	0.0633 (8)
H10	0.8768	0.7232	0.1191	0.076*
C11	0.9708 (4)	0.7072 (4)	−0.0079 (3)	0.0696 (10)
H11	1.0430	0.7899	0.0039	0.083*
C12	0.9656 (4)	0.6271 (4)	−0.0932 (3)	0.0643 (9)
C13	0.8574 (4)	0.5052 (4)	−0.1092 (2)	0.0631 (9)
H13	0.8527	0.4494	−0.1663	0.076*
C14	0.7560 (4)	0.4647 (3)	−0.0425 (2)	0.0577 (8)
H14	0.6831	0.3823	−0.0555	0.069*
C15	1.0760 (4)	0.6718 (5)	−0.1666 (3)	0.0884 (13)
H15A	1.0625	0.6020	−0.2183	0.133*
H15B	1.1808	0.7028	−0.1313	0.133*
H15C	1.0553	0.7392	−0.1969	0.133*
C16	0.6518 (3)	0.5021 (3)	0.1152 (2)	0.0460 (6)
C17	0.3434 (3)	0.2683 (3)	0.1692 (2)	0.0478 (7)
C18	0.2745 (4)	0.2739 (3)	0.2641 (2)	0.0536 (7)
C19	0.2976 (4)	0.1494 (3)	0.0962 (2)	0.0609 (8)
H19A	0.3261	0.1701	0.0313	0.073*
H19B	0.1860	0.1069	0.0868	0.073*
C20	0.3765 (4)	0.0608 (3)	0.1338 (3)	0.0633 (9)
C21	0.5281 (5)	0.0825 (4)	0.1244 (4)	0.1030 (16)
H21	0.5812	0.1509	0.0936	0.124*
C22	0.6049 (6)	0.0033 (5)	0.1603 (6)	0.137 (2)
H22	0.7087	0.0204	0.1548	0.165*
C23	0.5271 (8)	−0.0973 (5)	0.2027 (5)	0.1208 (19)
H23	0.5769	−0.1510	0.2255	0.145*
C24	0.3768 (8)	−0.1209 (4)	0.2124 (4)	0.1169 (19)
H24	0.3236	−0.1910	0.2415	0.140*
C25	0.3016 (6)	−0.0412 (4)	0.1791 (3)	0.0907 (13)
H25	0.1990	−0.0572	0.1876	0.109*
C26	0.5773 (8)	0.9020 (8)	0.5320 (7)	0.192 (3)
H26A	0.5100	0.8688	0.5794	0.287*
H26B	0.5167	0.8886	0.4663	0.287*
H26C	0.6320	0.9917	0.5531	0.287*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.0597 (3)	0.0463 (3)	0.0420 (3)	0.0246 (2)	0.0100 (2)	0.0063 (2)
O1	0.0668 (13)	0.0564 (12)	0.0399 (11)	0.0298 (11)	0.0082 (9)	0.0026 (9)
O2	0.0625 (13)	0.0522 (12)	0.0424 (11)	0.0141 (10)	0.0074 (9)	0.0052 (9)
O3	0.0648 (13)	0.0579 (13)	0.0488 (12)	0.0243 (11)	0.0197 (10)	0.0067 (10)
O4	0.0693 (15)	0.0715 (16)	0.0716 (16)	0.0101 (13)	0.0239 (13)	0.0126 (13)
O5	0.0803 (15)	0.0571 (13)	0.0625 (14)	0.0378 (12)	0.0081 (11)	0.0098 (10)
O6	0.224 (4)	0.093 (2)	0.095 (2)	0.063 (3)	0.004 (3)	0.0042 (19)
N1	0.0582 (15)	0.0502 (14)	0.0392 (12)	0.0195 (12)	0.0072 (11)	0.0048 (11)
N2	0.0612 (15)	0.0452 (13)	0.0477 (13)	0.0234 (12)	0.0136 (11)	0.0065 (10)
N3	0.0502 (13)	0.0548 (15)	0.0402 (12)	0.0211 (12)	0.0099 (10)	0.0082 (11)
N4	0.0507 (13)	0.0482 (14)	0.0409 (12)	0.0236 (12)	0.0069 (10)	0.0073 (10)
C1	0.0482 (16)	0.0497 (16)	0.0430 (16)	0.0149 (13)	0.0156 (13)	0.0099 (13)
C2	0.0472 (16)	0.0563 (17)	0.0449 (16)	0.0204 (14)	0.0132 (12)	0.0130 (13)
C3	0.087 (2)	0.065 (2)	0.0480 (18)	0.0383 (19)	0.0068 (17)	0.0034 (15)
C4	0.097 (3)	0.066 (2)	0.068 (2)	0.043 (2)	0.010 (2)	0.0006 (18)
C5	0.0551 (18)	0.0573 (19)	0.064 (2)	0.0216 (15)	0.0102 (15)	0.0146 (15)
C6	0.069 (2)	0.077 (2)	0.0493 (18)	0.0343 (19)	0.0046 (15)	0.0096 (16)
C7	0.067 (2)	0.068 (2)	0.0499 (18)	0.0332 (17)	0.0084 (15)	0.0012 (15)
C8	0.078 (2)	0.076 (3)	0.086 (3)	0.039 (2)	0.001 (2)	0.018 (2)
C9	0.0483 (16)	0.0611 (19)	0.0412 (15)	0.0244 (15)	0.0032 (12)	0.0143 (13)
C10	0.064 (2)	0.072 (2)	0.0525 (19)	0.0227 (18)	0.0051 (15)	0.0120 (16)
C11	0.0538 (19)	0.075 (2)	0.074 (2)	0.0112 (18)	0.0077 (17)	0.0268 (19)
C12	0.0523 (18)	0.097 (3)	0.0536 (19)	0.035 (2)	0.0096 (15)	0.0272 (19)
C13	0.0589 (19)	0.093 (3)	0.0459 (17)	0.036 (2)	0.0107 (15)	0.0135 (17)
C14	0.0541 (18)	0.073 (2)	0.0489 (18)	0.0246 (16)	0.0087 (14)	0.0125 (15)
C15	0.066 (2)	0.131 (4)	0.084 (3)	0.039 (2)	0.032 (2)	0.047 (3)
C16	0.0522 (16)	0.0533 (17)	0.0379 (15)	0.0251 (14)	0.0050 (12)	0.0105 (12)
C17	0.0507 (16)	0.0483 (17)	0.0465 (16)	0.0205 (14)	0.0051 (13)	0.0083 (13)
C18	0.0531 (17)	0.0575 (19)	0.0533 (18)	0.0218 (16)	0.0118 (14)	0.0098 (15)
C19	0.064 (2)	0.058 (2)	0.0531 (18)	0.0173 (16)	0.0009 (15)	−0.0016 (15)
C20	0.075 (2)	0.0433 (17)	0.066 (2)	0.0184 (16)	0.0049 (17)	−0.0017 (15)
C21	0.081 (3)	0.064 (3)	0.170 (5)	0.029 (2)	0.020 (3)	0.032 (3)
C22	0.096 (4)	0.073 (3)	0.249 (8)	0.037 (3)	0.012 (4)	0.040 (4)
C23	0.139 (5)	0.073 (3)	0.163 (6)	0.055 (3)	0.014 (4)	0.024 (3)
C24	0.176 (6)	0.066 (3)	0.131 (4)	0.054 (4)	0.051 (4)	0.042 (3)
C25	0.105 (3)	0.064 (2)	0.108 (3)	0.028 (2)	0.036 (3)	0.018 (2)
C26	0.147 (5)	0.208 (7)	0.229 (7)	0.077 (5)	0.040 (5)	0.015 (6)

Geometric parameters (Å, º) top

V1—O5	1.583 (2)	C9—C10	1.384 (4)
V1—N2	1.875 (2)	C9—C14	1.391 (4)
V1—O2	1.970 (2)	C9—C16	1.473 (4)
V1—O3	1.996 (2)	C10—C11	1.395 (5)
V1—N4	2.080 (2)	C10—H10	0.9300
V1—O1	2.215 (2)	C11—C12	1.373 (5)
O1—C1	1.241 (3)	C11—H11	0.9300
O2—C16	1.301 (3)	C12—C13	1.378 (5)
O3—C18	1.297 (4)	C12—C15	1.507 (5)
O4—C18	1.224 (4)	C13—C14	1.375 (4)
O6—C26	1.426 (4)	C13—H13	0.9300
O6—H6	0.8400	C14—H14	0.9300
N1—C1	1.344 (4)	C15—H15A	0.9600
N1—N2	1.353 (3)	C15—H15B	0.9600
N1—H1	0.8600	C15—H15C	0.9600
N2—H2	0.8600	C17—C19	1.481 (4)
N3—C16	1.312 (4)	C17—C18	1.500 (4)
N3—N4	1.375 (3)	C19—C20	1.513 (5)
N4—C17	1.286 (4)	C19—H19A	0.9700
C1—C2	1.465 (4)	C19—H19B	0.9700
C2—C3	1.383 (4)	C20—C21	1.368 (5)
C2—C7	1.384 (4)	C20—C25	1.370 (5)
C3—C4	1.372 (5)	C21—C22	1.403 (6)
C3—H3A	0.9300	C21—H21	0.9300
C4—C5	1.385 (5)	C22—C23	1.344 (7)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.377 (5)	C23—C24	1.354 (7)
C5—C8	1.513 (4)	C23—H23	0.9300
C6—C7	1.384 (4)	C24—C25	1.387 (7)
C6—H6A	0.9300	C24—H24	0.9300
C7—H7	0.9300	C25—H25	0.9300
C8—H8A	0.9600	C26—H26A	0.9600
C8—H8B	0.9600	C26—H26B	0.9600
C8—H8C	0.9600	C26—H26C	0.9600

O5—V1—N2	93.97 (11)	C9—C10—H10	120.1
O5—V1—O2	98.37 (11)	C11—C10—H10	120.1
N2—V1—O2	105.98 (10)	C12—C11—C10	121.5 (3)
O5—V1—O3	97.34 (11)	C12—C11—H11	119.2
N2—V1—O3	98.78 (9)	C10—C11—H11	119.2
O2—V1—O3	149.52 (9)	C11—C12—C13	118.2 (3)
O5—V1—N4	112.73 (10)	C11—C12—C15	120.5 (4)
N2—V1—N4	153.13 (10)	C13—C12—C15	121.3 (4)
O2—V1—N4	74.21 (9)	C14—C13—C12	121.3 (3)
O3—V1—N4	75.66 (9)	C14—C13—H13	119.4
O5—V1—O1	167.08 (10)	C12—C13—H13	119.4
N2—V1—O1	73.11 (9)	C13—C14—C9	120.8 (3)
O2—V1—O1	85.61 (8)	C13—C14—H14	119.6
O3—V1—O1	84.85 (8)	C9—C14—H14	119.6
N4—V1—O1	80.17 (8)	C12—C15—H15A	109.5
C1—O1—V1	113.77 (18)	C12—C15—H15B	109.5
C16—O2—V1	116.79 (18)	H15A—C15—H15B	109.5
C18—O3—V1	119.46 (18)	C12—C15—H15C	109.5
C26—O6—H6	109.5	H15A—C15—H15C	109.5
C1—N1—N2	114.8 (2)	H15B—C15—H15C	109.5
C1—N1—H1	122.6	O2—C16—N3	123.4 (3)
N2—N1—H1	122.6	O2—C16—C9	118.2 (3)
N1—N2—V1	122.31 (18)	N3—C16—C9	118.3 (2)
N1—N2—H2	118.8	N4—C17—C19	126.7 (3)
V1—N2—H2	118.8	N4—C17—C18	110.9 (3)
C16—N3—N4	107.1 (2)	C19—C17—C18	122.1 (3)
C17—N4—N3	122.2 (2)	O4—C18—O3	124.2 (3)
C17—N4—V1	119.05 (19)	O4—C18—C17	121.2 (3)
N3—N4—V1	118.32 (17)	O3—C18—C17	114.6 (3)
O1—C1—N1	115.7 (3)	C17—C19—C20	110.7 (3)
O1—C1—C2	123.6 (3)	C17—C19—H19A	109.5
N1—C1—C2	120.7 (3)	C20—C19—H19A	109.5
C3—C2—C7	118.2 (3)	C17—C19—H19B	109.5
C3—C2—C1	118.4 (3)	C20—C19—H19B	109.5
C7—C2—C1	123.4 (3)	H19A—C19—H19B	108.1
C4—C3—C2	120.5 (3)	C21—C20—C25	117.8 (4)
C4—C3—H3A	119.8	C21—C20—C19	120.1 (3)
C2—C3—H3A	119.8	C25—C20—C19	122.2 (4)
C3—C4—C5	121.9 (3)	C20—C21—C22	121.3 (4)
C3—C4—H4	119.0	C20—C21—H21	119.4
C5—C4—H4	119.0	C22—C21—H21	119.4
C6—C5—C4	117.4 (3)	C23—C22—C21	119.4 (5)
C6—C5—C8	121.0 (3)	C23—C22—H22	120.3
C4—C5—C8	121.6 (3)	C21—C22—H22	120.3
C5—C6—C7	121.3 (3)	C22—C23—C24	120.4 (5)
C5—C6—H6A	119.4	C22—C23—H23	119.8
C7—C6—H6A	119.4	C24—C23—H23	119.8
C2—C7—C6	120.7 (3)	C23—C24—C25	120.3 (5)
C2—C7—H7	119.6	C23—C24—H24	119.8
C6—C7—H7	119.6	C25—C24—H24	119.8
C5—C8—H8A	109.5	C20—C25—C24	120.8 (4)
C5—C8—H8B	109.5	C20—C25—H25	119.6
H8A—C8—H8B	109.5	C24—C25—H25	119.6
C5—C8—H8C	109.5	O6—C26—H26A	109.5
H8A—C8—H8C	109.5	O6—C26—H26B	109.5
H8B—C8—H8C	109.5	H26A—C26—H26B	109.5
C10—C9—C14	118.4 (3)	O6—C26—H26C	109.5
C10—C9—C16	120.9 (3)	H26A—C26—H26C	109.5
C14—C9—C16	120.7 (3)	H26B—C26—H26C	109.5
C9—C10—C11	119.9 (3)

O5—V1—O1—C1	5.1 (5)	C4—C5—C6—C7	1.5 (5)
N2—V1—O1—C1	5.47 (19)	C8—C5—C6—C7	−178.9 (3)
O2—V1—O1—C1	113.6 (2)	C3—C2—C7—C6	−0.9 (5)
O3—V1—O1—C1	−95.3 (2)	C1—C2—C7—C6	179.1 (3)
N4—V1—O1—C1	−171.6 (2)	C5—C6—C7—C2	0.2 (5)
O5—V1—O2—C16	−108.5 (2)	C14—C9—C10—C11	0.5 (5)
N2—V1—O2—C16	154.9 (2)	C16—C9—C10—C11	−178.8 (3)
O3—V1—O2—C16	11.8 (3)	C9—C10—C11—C12	−0.7 (5)
N4—V1—O2—C16	2.85 (19)	C10—C11—C12—C13	0.2 (5)
O1—V1—O2—C16	83.9 (2)	C10—C11—C12—C15	−179.6 (3)
O5—V1—O3—C18	115.4 (2)	C11—C12—C13—C14	0.5 (5)
N2—V1—O3—C18	−149.4 (2)	C15—C12—C13—C14	−179.6 (3)
O2—V1—O3—C18	−5.1 (3)	C12—C13—C14—C9	−0.8 (5)
N4—V1—O3—C18	3.8 (2)	C10—C9—C14—C13	0.3 (5)
O1—V1—O3—C18	−77.4 (2)	C16—C9—C14—C13	179.5 (3)
C1—N1—N2—V1	4.3 (3)	V1—O2—C16—N3	−4.0 (4)
O5—V1—N2—N1	174.8 (2)	V1—O2—C16—C9	176.91 (18)
O2—V1—N2—N1	−85.3 (2)	N4—N3—C16—O2	2.2 (4)
O3—V1—N2—N1	76.8 (2)	N4—N3—C16—C9	−178.7 (2)
N4—V1—N2—N1	1.2 (4)	C10—C9—C16—O2	−8.9 (4)
O1—V1—N2—N1	−5.07 (19)	C14—C9—C16—O2	171.9 (3)
C16—N3—N4—C17	−171.9 (2)	C10—C9—C16—N3	172.0 (3)
C16—N3—N4—V1	0.5 (3)	C14—C9—C16—N3	−7.3 (4)
O5—V1—N4—C17	−96.6 (2)	N3—N4—C17—C19	2.4 (4)
N2—V1—N4—C17	76.5 (3)	V1—N4—C17—C19	−169.9 (2)
O2—V1—N4—C17	170.8 (2)	N3—N4—C17—C18	176.7 (2)
O3—V1—N4—C17	−4.5 (2)	V1—N4—C17—C18	4.3 (3)
O1—V1—N4—C17	82.6 (2)	V1—O3—C18—O4	175.6 (2)
O5—V1—N4—N3	90.8 (2)	V1—O3—C18—C17	−2.7 (3)
N2—V1—N4—N3	−96.1 (3)	N4—C17—C18—O4	−179.5 (3)
O2—V1—N4—N3	−1.82 (17)	C19—C17—C18—O4	−4.9 (5)
O3—V1—N4—N3	−177.2 (2)	N4—C17—C18—O3	−1.1 (4)
O1—V1—N4—N3	−90.01 (18)	C19—C17—C18—O3	173.5 (3)
V1—O1—C1—N1	−5.0 (3)	N4—C17—C19—C20	95.4 (4)
V1—O1—C1—C2	175.4 (2)	C18—C17—C19—C20	−78.3 (4)
N2—N1—C1—O1	1.1 (4)	C17—C19—C20—C21	−78.5 (4)
N2—N1—C1—C2	−179.3 (2)	C17—C19—C20—C25	100.5 (4)
O1—C1—C2—C3	4.6 (4)	C25—C20—C21—C22	−0.3 (7)
N1—C1—C2—C3	−175.0 (3)	C19—C20—C21—C22	178.8 (5)
O1—C1—C2—C7	−175.4 (3)	C20—C21—C22—C23	1.5 (9)
N1—C1—C2—C7	5.0 (4)	C21—C22—C23—C24	−1.2 (10)
C7—C2—C3—C4	−0.1 (5)	C22—C23—C24—C25	−0.3 (10)
C1—C2—C3—C4	179.9 (3)	C21—C20—C25—C24	−1.2 (7)
C2—C3—C4—C5	1.9 (6)	C19—C20—C25—C24	179.8 (4)
C3—C4—C5—C6	−2.5 (6)	C23—C24—C25—C20	1.5 (8)
C3—C4—C5—C8	177.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O4ⁱ	0.84	2.18	2.821 (5)	133
N1—H1···O3ⁱ	0.86	2.13	2.808 (3)	135
N2—H2···O6	0.86	1.99	2.800 (4)	156

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[V(C₈H₉N₂O)(C₁₇H₁₄N₂O₃)O]·CH₄O
M_r	542.46
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.2770 (2), 11.2558 (2), 13.4691 (3)
α, β, γ (°)	95.769 (2), 96.708 (2), 109.675 (2)
V (Å³)	1300.48 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.35 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.864, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	12503, 5956, 3843
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.167, 1.03
No. of reflections	5956
No. of parameters	337
No. of restraints	13
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.48

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O4ⁱ	0.84	2.18	2.821 (5)	133
N1—H1···O3ⁱ	0.86	2.13	2.808 (3)	135
N2—H2···O6	0.86	1.99	2.800 (4)	156

Symmetry code: (i) −x+1, −y+1, −z+1.

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
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). publCIF. In preparation. Google Scholar
Wong, H. W., Lo, K. M. & Ng, S. W. (2009a). Acta Cryst. E65, m422. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wong, H. W., Lo, K. M. & Ng, S. W. (2009b). Acta Cryst. E65, m718. Web of Science CSD CrossRef IUCr Journals Google Scholar

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