Methanol{2-meth-oxy-6-[(2-oxidoprop-yl)imino-meth-yl]phenolato}dioxidomolyb-denum(VI).

In the structure of the title compound, [Mo(C(11)H(13)NO(3))O(2)(CH(3)OH)], the Mo(VI) ion is octahedrally coordinated by two oxide O atoms, the N atom and two deprotonated OH groups of the tridentate Schiff base ligand 2-meth-oxy-6-[(2-oxidoprop-yl)imino-meth-yl]phenolate and by a methanol O atom. In the crystal structure, two complexes are linked via O-H⋯O hydrogen bonds, yielding a centrosymmetric arrangement involving the methanol hydr-oxy group and one of the ligand O atoms coordinated to the Mo(VI) ion.

Related literature

For molybdenum (VI) n class="Chemical">Schiff base complexes in bioinorganic chemistry, see: Holm et al. (1996 ▶) and as oxidation catalysts, see: Arnaiz et al. (2000 ▶); Sheikhshoaie et al. (2009 ▶). For similar structures, see: Abbasi et al. (2008 ▶); Monadi et al. (2009 ▶); Syamal & Maurya (1989 ▶).

Experimental

Crystal data

[Mo(C11H13NO3)O2(CH4O)]

M = 367.21

Monoclinic,

a = 6.7551 (5) Å

b = 15.8357 (14) Å

c = 13.1198 (10) Å

β = 98.287 (9)°

V = 1388.79 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.97 mm−1

T = 173 K

0.38 × 0.38 × 0.34 mm

Data collection

Stoe IPDS diffractometer

Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009 ▶) T min = 0.625, T max = 0.716

10555 measured reflections

2666 independent reflections

2601 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.063

S = 1.16

2666 reflections

187 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.60 e Å−3

Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2000 ▶); cell refinement: CELL in IPDS-I; data reduction: INTEGRATE in IPDS-I; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATOn class="Chemical">N (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809047485/fi2093sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047485/fi2093Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Mo(C11H13NO3)O2(CH4O)]	F(000) = 744
Mr = 367.21	Dx = 1.756 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8000 reflections
a = 6.7551 (5) Å	θ = 2.0–26.1°
b = 15.8357 (14) Å	µ = 0.97 mm−1
c = 13.1198 (10) Å	T = 173 K
β = 98.287 (9)°	Block, yellow
V = 1388.79 (19) Å3	0.38 × 0.38 × 0.34 mm
Z = 4

Stoe IPDS diffractometer	2666 independent reflections
Radiation source: fine-focus sealed tube	2601 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ rotation scans	θmax = 25.9°, θmin = 2.6°
Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009)	h = −7→8
Tmin = 0.625, Tmax = 0.716	k = −19→19
10555 measured reflections	l = −16→16

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.0288P)2 + 1.2212P] where P = (Fo2 + 2Fc2)/3
2666 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.41 e Å−3
1 restraint	Δρmin = −0.59 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. The OH H-atom was located in a difference electron-density map and refined with a distance constraint of 0.84 (2) Å and Uiso(H) = 1.5Ueq(parent O-atom). The remainder of the H-atoms could all be located from difference electron-density maps but were included in calculated positions and treated as riding atoms: C—H = 0.95 - 1.00 Å, with Uiso(H) = k × Ueq(parent C-atom), where k = 1.2 for CH and CH2 H-atoms, and 1.5 for methyl H-atoms. Using the Stoe IPDS1, one-circle image plate diffraction system, it is often only possible to access 94% maximum of the Ewald sphere depending on the crystal system and the position of the crystal. Here however, 98% of the data were accessible out to 25° in θ.

	x	y	z	Uiso*/Ueq
Mo1	0.03631 (2)	0.11249 (1)	0.15344 (1)	0.0156 (1)
O1	0.0326 (2)	0.12028 (9)	0.00507 (12)	0.0197 (4)
O2	0.1700 (2)	0.08957 (10)	0.29193 (11)	0.0210 (4)
O3	0.1839 (2)	0.06916 (11)	0.48988 (12)	0.0289 (5)
O4	−0.0341 (2)	0.21363 (10)	0.17290 (12)	0.0236 (4)
O5	−0.1751 (2)	0.05346 (10)	0.15022 (12)	0.0228 (4)
O6	0.1883 (2)	−0.01628 (10)	0.12101 (12)	0.0238 (5)
N1	0.3526 (3)	0.14577 (12)	0.13382 (14)	0.0202 (5)
C1	0.1774 (3)	0.17293 (15)	−0.03365 (18)	0.0261 (6)
C2	0.3783 (3)	0.14935 (16)	0.02534 (17)	0.0270 (7)
C3	0.5000 (3)	0.16301 (13)	0.20319 (17)	0.0203 (6)
C4	0.4983 (3)	0.15205 (13)	0.31189 (17)	0.0200 (6)
C5	0.6718 (3)	0.17449 (15)	0.37898 (19)	0.0263 (7)
C6	0.6822 (3)	0.16196 (17)	0.48262 (19)	0.0319 (7)
C7	0.5213 (4)	0.12683 (16)	0.52236 (19)	0.0294 (7)
C8	0.3482 (3)	0.10346 (14)	0.45824 (18)	0.0223 (6)
C9	0.3363 (3)	0.11557 (12)	0.35135 (17)	0.0189 (6)
C10	0.1682 (4)	0.16163 (15)	−0.14788 (18)	0.0272 (7)
C11	0.1874 (4)	0.05673 (19)	0.59784 (18)	0.0359 (8)
C12	0.3293 (4)	−0.06281 (18)	0.1874 (2)	0.0387 (8)
H1	0.14830	0.23330	−0.01900	0.0310*
H2A	0.42220	0.09380	0.00210	0.0320*
H2B	0.48010	0.19220	0.01460	0.0320*
H3	0.61850	0.18450	0.18150	0.0240*
H5	0.78240	0.19850	0.35210	0.0320*
H6	0.79980	0.17730	0.52760	0.0380*
H6O	0.117 (4)	−0.0505 (16)	0.084 (2)	0.0360*
H7	0.52970	0.11860	0.59460	0.0350*
H10A	0.03800	0.18110	−0.18270	0.0410*
H10B	0.18550	0.10180	−0.16340	0.0410*
H10C	0.27490	0.19470	−0.17210	0.0410*
H11A	0.20460	0.11130	0.63330	0.0540*
H11B	0.29890	0.01940	0.62400	0.0540*
H11C	0.06120	0.03100	0.61040	0.0540*
H12A	0.27690	−0.07390	0.25200	0.0580*
H12B	0.45390	−0.03050	0.20190	0.0580*
H12C	0.35560	−0.11650	0.15480	0.0580*

	U11	U22	U33	U12	U13	U23
Mo1	0.0105 (1)	0.0213 (1)	0.0142 (1)	−0.0008 (1)	−0.0009 (1)	−0.0025 (1)
O1	0.0183 (7)	0.0248 (8)	0.0153 (7)	−0.0021 (6)	−0.0003 (6)	−0.0011 (6)
O2	0.0145 (7)	0.0326 (8)	0.0149 (7)	−0.0038 (6)	−0.0017 (6)	−0.0012 (6)
O3	0.0265 (8)	0.0427 (10)	0.0162 (8)	−0.0051 (7)	−0.0015 (6)	0.0021 (7)
O4	0.0205 (7)	0.0258 (8)	0.0236 (8)	−0.0017 (6)	0.0005 (6)	−0.0059 (6)
O5	0.0163 (7)	0.0257 (8)	0.0254 (8)	−0.0022 (6)	−0.0007 (6)	−0.0022 (6)
O6	0.0233 (8)	0.0236 (8)	0.0215 (8)	0.0028 (6)	−0.0067 (6)	−0.0039 (6)
N1	0.0142 (8)	0.0271 (10)	0.0193 (9)	−0.0012 (7)	0.0022 (7)	0.0005 (7)
C1	0.0287 (11)	0.0255 (11)	0.0239 (11)	−0.0032 (9)	0.0031 (9)	0.0022 (9)
C2	0.0212 (10)	0.0398 (13)	0.0206 (11)	−0.0048 (10)	0.0056 (9)	0.0007 (10)
C3	0.0120 (9)	0.0218 (10)	0.0271 (11)	0.0007 (8)	0.0027 (8)	−0.0034 (9)
C4	0.0142 (9)	0.0210 (10)	0.0237 (11)	0.0027 (8)	−0.0011 (8)	−0.0055 (8)
C5	0.0146 (10)	0.0322 (12)	0.0305 (12)	−0.0005 (9)	−0.0025 (9)	−0.0084 (10)
C6	0.0202 (10)	0.0413 (14)	0.0300 (13)	−0.0010 (10)	−0.0103 (9)	−0.0085 (11)
C7	0.0282 (12)	0.0373 (13)	0.0193 (11)	0.0023 (10)	−0.0076 (10)	−0.0032 (10)
C8	0.0212 (11)	0.0253 (11)	0.0190 (11)	0.0021 (8)	−0.0020 (9)	−0.0024 (8)
C9	0.0152 (10)	0.0201 (10)	0.0196 (11)	0.0035 (7)	−0.0039 (8)	−0.0051 (8)
C10	0.0303 (12)	0.0283 (11)	0.0228 (12)	−0.0026 (9)	0.0036 (9)	0.0054 (9)
C11	0.0410 (14)	0.0494 (16)	0.0166 (11)	−0.0071 (12)	0.0017 (10)	0.0023 (11)
C12	0.0356 (13)	0.0363 (14)	0.0382 (15)	0.0152 (11)	−0.0147 (11)	−0.0059 (11)

Mo1—O1	1.9471 (16)	C6—C7	1.388 (3)
Mo1—O2	1.9431 (14)	C7—C8	1.389 (3)
Mo1—O4	1.7005 (16)	C8—C9	1.406 (3)
Mo1—O5	1.7022 (15)	C1—H1	1.0000
Mo1—O6	2.3493 (16)	C2—H2A	0.9900
Mo1—N1	2.251 (2)	C2—H2B	0.9900
O1—C1	1.433 (3)	C3—H3	0.9500
O2—C9	1.337 (3)	C5—H5	0.9500
O3—C8	1.354 (3)	C6—H6	0.9500
O3—C11	1.427 (3)	C7—H7	0.9500
O6—C12	1.403 (3)	C10—H10A	0.9800
O6—H6O	0.83 (3)	C10—H10B	0.9800
N1—C2	1.460 (3)	C10—H10C	0.9800
N1—C3	1.278 (3)	C11—H11A	0.9800
C1—C2	1.509 (3)	C11—H11B	0.9800
C1—C10	1.502 (3)	C11—H11C	0.9800
C3—C4	1.438 (3)	C12—H12A	0.9800
C4—C9	1.401 (3)	C12—H12B	0.9800
C4—C5	1.406 (3)	C12—H12C	0.9800
C5—C6	1.366 (3)
O1—Mo1—O2	152.13 (6)	C4—C9—C8	119.30 (19)
O1—Mo1—O4	97.29 (7)	O2—C9—C4	123.2 (2)
O1—Mo1—O5	96.90 (7)	O2—C9—C8	117.52 (18)
O1—Mo1—O6	79.45 (6)	O1—C1—H1	109.00
O1—Mo1—N1	75.32 (6)	C2—C1—H1	109.00
O2—Mo1—O4	97.93 (7)	C10—C1—H1	109.00
O2—Mo1—O5	101.30 (7)	N1—C2—H2A	110.00
O2—Mo1—O6	81.43 (6)	N1—C2—H2B	110.00
O2—Mo1—N1	80.20 (6)	C1—C2—H2A	110.00
O4—Mo1—O5	105.61 (7)	C1—C2—H2B	110.00
O4—Mo1—O6	169.64 (6)	H2A—C2—H2B	109.00
O4—Mo1—N1	95.01 (7)	N1—C3—H3	118.00
O5—Mo1—O6	84.60 (6)	C4—C3—H3	118.00
O5—Mo1—N1	158.82 (7)	C4—C5—H5	120.00
O6—Mo1—N1	74.68 (6)	C6—C5—H5	120.00
Mo1—O1—C1	118.70 (13)	C5—C6—H6	120.00
Mo1—O2—C9	136.56 (13)	C7—C6—H6	120.00
C8—O3—C11	117.57 (18)	C6—C7—H7	119.00
Mo1—O6—C12	128.21 (14)	C8—C7—H7	119.00
C12—O6—H6O	107.7 (18)	C1—C10—H10A	109.00
Mo1—O6—H6O	116.1 (19)	C1—C10—H10B	109.00
Mo1—N1—C3	128.57 (15)	C1—C10—H10C	109.00
Mo1—N1—C2	111.65 (13)	H10A—C10—H10B	109.00
C2—N1—C3	119.75 (19)	H10A—C10—H10C	109.00
O1—C1—C10	110.63 (19)	H10B—C10—H10C	110.00
O1—C1—C2	106.47 (18)	O3—C11—H11A	109.00
C2—C1—C10	112.78 (19)	O3—C11—H11B	109.00
N1—C2—C1	106.57 (17)	O3—C11—H11C	110.00
N1—C3—C4	124.3 (2)	H11A—C11—H11B	109.00
C3—C4—C9	122.31 (19)	H11A—C11—H11C	109.00
C3—C4—C5	117.72 (19)	H11B—C11—H11C	109.00
C5—C4—C9	119.9 (2)	O6—C12—H12A	109.00
C4—C5—C6	120.3 (2)	O6—C12—H12B	109.00
C5—C6—C7	120.1 (2)	O6—C12—H12C	110.00
C6—C7—C8	121.1 (2)	H12A—C12—H12B	109.00
O3—C8—C9	115.41 (19)	H12A—C12—H12C	109.00
C7—C8—C9	119.3 (2)	H12B—C12—H12C	109.00
O3—C8—C7	125.3 (2)
O2—Mo1—O1—C1	−55.3 (2)	Mo1—O2—C9—C4	−21.0 (3)
O4—Mo1—O1—C1	67.30 (14)	Mo1—O2—C9—C8	160.43 (15)
O5—Mo1—O1—C1	174.09 (14)	C11—O3—C8—C7	0.7 (3)
O6—Mo1—O1—C1	−102.75 (14)	C11—O3—C8—C9	−179.1 (2)
N1—Mo1—O1—C1	−25.99 (14)	Mo1—N1—C2—C1	28.0 (2)
O1—Mo1—O2—C9	53.8 (3)	C3—N1—C2—C1	−150.1 (2)
O4—Mo1—O2—C9	−68.64 (19)	Mo1—N1—C3—C4	9.8 (3)
O5—Mo1—O2—C9	−176.39 (19)	C2—N1—C3—C4	−172.5 (2)
O6—Mo1—O2—C9	100.92 (19)	O1—C1—C2—N1	−46.5 (2)
N1—Mo1—O2—C9	25.11 (19)	C10—C1—C2—N1	−168.03 (19)
O1—Mo1—O6—C12	151.18 (18)	N1—C3—C4—C5	−179.5 (2)
O2—Mo1—O6—C12	−8.45 (18)	N1—C3—C4—C9	4.4 (3)
O5—Mo1—O6—C12	−110.76 (18)	C3—C4—C5—C6	−177.1 (2)
N1—Mo1—O6—C12	73.67 (18)	C9—C4—C5—C6	−0.9 (3)
O1—Mo1—N1—C2	−3.26 (14)	C3—C4—C9—O2	−1.2 (3)
O1—Mo1—N1—C3	174.7 (2)	C3—C4—C9—C8	177.28 (19)
O2—Mo1—N1—C2	163.30 (16)	C5—C4—C9—O2	−177.24 (19)
O2—Mo1—N1—C3	−18.79 (19)	C5—C4—C9—C8	1.3 (3)
O4—Mo1—N1—C2	−99.50 (15)	C4—C5—C6—C7	0.1 (4)
O4—Mo1—N1—C3	78.4 (2)	C5—C6—C7—C8	0.3 (4)
O5—Mo1—N1—C2	67.3 (3)	C6—C7—C8—O3	−179.7 (2)
O5—Mo1—N1—C3	−114.8 (2)	C6—C7—C8—C9	0.1 (4)
O6—Mo1—N1—C2	79.59 (15)	O3—C8—C9—O2	−2.5 (3)
O6—Mo1—N1—C3	−102.5 (2)	O3—C8—C9—C4	178.94 (19)
Mo1—O1—C1—C2	49.6 (2)	C7—C8—C9—O2	177.7 (2)
Mo1—O1—C1—C10	172.42 (14)	C7—C8—C9—C4	−0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6O···O1i	0.83 (3)	1.81 (3)	2.639 (2)	176 (2)
C3—H3···O4ii	0.95	2.41	3.327 (2)	162
C3—H3···O5ii	0.95	2.57	2.958 (3)	105
C10—H10A···O4iii	0.98	2.52	3.221 (3)	128
C10—H10B···O5i	0.98	2.47	3.407 (3)	161
C11—H11C···O3iv	0.98	2.52	3.280 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6O⋯O1i	0.83 (3)	1.81 (3)	2.639 (2)	176 (2)

Symmetry code: (i) .