Methano-ldioxido{1-[(2RS)-(2-oxidoprop-yl)iminometh-yl]-2-naphtholato}molybdenium(VI).

Crystals of the title compound, [Mo(C(14)H(13)NO(2))O(2)(CH(4)O)], were obtained by recrystallization from methanol. The Mo(VI) atom is coordinated by two oxide O atoms and by two O atoms and one N atom of the tridentate 1-[(2-oxidoprop-yl)iminometh-yl]-2-naphtholate Schiff base ligand. The coordination sphere is completed by the O atom of a methanol mol-ecule, yielding a distorted octa-hedron. O-H⋯O hydrogen bonding yields centrosymmetric dimers.

Related literature

For related structures with O= MoVI=O units and for the synthesis, see: Arnaiz et al. (2000 ▶); Holm et al. (1996 ▶); Syamal & Maurya (1989 ▶). For the prperties of related compounds, see: Arnold et al. (2001 ▶); Bagherzadeh et al. (2009 ▶); Bruno et al. (2006 ▶); Holm (1987 ▶); Maurya et al. (1997 ▶); Schurig & Betschinger (1992 ▶); Sheikhshoaie et al. (2009 ▶).

Experimental

Crystal data

[Mo(C14H13NO2)O2(CH4O)]

M = 387.24

Monoclinic,

a = 7.9064 (5) Å

b = 15.078 (1) Å

c = 12.6796 (8) Å

β = 93.959 (1)°

V = 1507.96 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.89 mm−1

T = 100 K

0.19 × 0.16 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.849, T max = 0.870

18948 measured reflections

4393 independent reflections

3951 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.056

S = 1.01

4393 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.65 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681000262X/fi2095sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000262X/fi2095Isup2.hkl

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

[Mo(C14H13NO2)O2(CH4O)]	F(000) = 784
Mr = 387.24	Dx = 1.706 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 211 reflections
a = 7.9064 (5) Å	θ = 3–30°
b = 15.078 (1) Å	µ = 0.89 mm−1
c = 12.6796 (8) Å	T = 100 K
β = 93.959 (1)°	Prism, pale yellow
V = 1507.96 (17) Å3	0.19 × 0.16 × 0.16 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4393 independent reflections
Radiation source: fine-focus sealed tube	3951 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 30.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.849, Tmax = 0.870	k = −21→21
18948 measured reflections	l = −17→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0248P)2 + 1.35P] where P = (Fo2 + 2Fc2)/3
4393 reflections	(Δ/σ)max = 0.008
202 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.65 e Å−3

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.

	x	y	z	Uiso*/Ueq
Mo1	0.530764 (16)	0.118564 (9)	0.344992 (10)	0.01228 (4)
O1	0.58279 (14)	0.07661 (8)	0.20452 (9)	0.0154 (2)
O2	0.58637 (14)	0.12750 (7)	0.49712 (9)	0.0149 (2)
O3	0.51942 (15)	0.22791 (8)	0.31257 (10)	0.0203 (2)
O4	0.32656 (14)	0.08304 (9)	0.35495 (10)	0.0197 (2)
O5	0.60141 (16)	−0.02912 (8)	0.38095 (10)	0.0191 (2)
H5O	0.5424	−0.0612	0.4195	0.029 (6)*
N1	0.81591 (16)	0.11919 (9)	0.36213 (10)	0.0132 (2)
C1	0.86943 (19)	0.12061 (10)	0.17666 (12)	0.0122 (3)
C2	0.70542 (19)	0.09463 (10)	0.14066 (12)	0.0129 (3)
C3	0.6632 (2)	0.08250 (11)	0.03095 (13)	0.0157 (3)
H3A	0.5510	0.0660	0.0072	0.019*
C4	0.7821 (2)	0.09422 (11)	−0.04064 (13)	0.0178 (3)
H4A	0.7531	0.0827	−0.1133	0.021*
C5	1.0683 (2)	0.14082 (12)	−0.08389 (13)	0.0197 (3)
H5A	1.0391	0.1293	−0.1565	0.024*
C6	1.2258 (2)	0.17414 (12)	−0.05370 (14)	0.0219 (3)
H6A	1.3049	0.1859	−0.1051	0.026*
C7	1.2691 (2)	0.19074 (11)	0.05381 (14)	0.0191 (3)
H7A	1.3777	0.2143	0.0748	0.023*
C8	1.15642 (19)	0.17334 (11)	0.12916 (13)	0.0156 (3)
H8A	1.1883	0.1850	0.2014	0.019*
C9	0.9488 (2)	0.12333 (11)	−0.00845 (12)	0.0152 (3)
C10	0.99294 (19)	0.13813 (10)	0.10045 (12)	0.0126 (3)
C11	0.91962 (19)	0.12357 (10)	0.28859 (12)	0.0138 (3)
H11A	1.0370	0.1291	0.3090	0.017*
C12	0.8805 (2)	0.11752 (12)	0.47316 (12)	0.0180 (3)
H12A	0.9898	0.1496	0.4824	0.022*
H12B	0.8983	0.0556	0.4975	0.022*
C13	0.7473 (2)	0.16280 (11)	0.53555 (13)	0.0171 (3)
H13A	0.7493	0.2280	0.5215	0.021*
C14	0.7770 (2)	0.14687 (12)	0.65327 (13)	0.0207 (3)
H14A	0.6881	0.1765	0.6904	0.031*
H14B	0.8879	0.1707	0.6782	0.031*
H14C	0.7741	0.0830	0.6675	0.031*
C15	0.6958 (2)	−0.08893 (12)	0.32155 (16)	0.0254 (4)
H15A	0.7596	−0.1296	0.3697	0.038*
H15B	0.7749	−0.0555	0.2805	0.038*
H15C	0.6182	−0.1230	0.2735	0.038*

	U11	U22	U33	U12	U13	U23
Mo1	0.00938 (6)	0.01464 (7)	0.01329 (7)	0.00158 (5)	0.00413 (4)	0.00367 (5)
O1	0.0115 (5)	0.0216 (6)	0.0134 (5)	−0.0023 (4)	0.0032 (4)	0.0024 (4)
O2	0.0145 (5)	0.0171 (5)	0.0139 (5)	−0.0004 (4)	0.0057 (4)	0.0014 (4)
O3	0.0199 (6)	0.0187 (6)	0.0232 (6)	0.0048 (5)	0.0084 (5)	0.0080 (5)
O4	0.0122 (5)	0.0270 (6)	0.0203 (6)	−0.0003 (5)	0.0038 (4)	0.0053 (5)
O5	0.0249 (6)	0.0135 (5)	0.0205 (6)	0.0016 (5)	0.0130 (5)	0.0023 (4)
N1	0.0117 (6)	0.0159 (6)	0.0121 (6)	0.0016 (5)	0.0018 (4)	0.0015 (5)
C1	0.0120 (6)	0.0139 (7)	0.0110 (6)	0.0004 (5)	0.0033 (5)	0.0007 (5)
C2	0.0122 (6)	0.0129 (7)	0.0138 (7)	0.0002 (5)	0.0040 (5)	0.0010 (5)
C3	0.0150 (7)	0.0166 (7)	0.0155 (7)	−0.0029 (6)	0.0014 (5)	−0.0012 (6)
C4	0.0195 (8)	0.0217 (8)	0.0125 (7)	−0.0011 (6)	0.0024 (6)	−0.0024 (6)
C5	0.0208 (8)	0.0255 (8)	0.0137 (7)	0.0009 (6)	0.0073 (6)	0.0007 (6)
C6	0.0201 (8)	0.0260 (9)	0.0212 (8)	−0.0014 (7)	0.0118 (6)	0.0013 (7)
C7	0.0136 (7)	0.0208 (8)	0.0238 (8)	−0.0018 (6)	0.0074 (6)	0.0007 (6)
C8	0.0127 (7)	0.0180 (7)	0.0164 (7)	−0.0005 (5)	0.0032 (6)	0.0007 (6)
C9	0.0159 (7)	0.0169 (7)	0.0133 (7)	0.0008 (6)	0.0048 (5)	0.0001 (5)
C10	0.0129 (6)	0.0120 (7)	0.0132 (7)	0.0006 (5)	0.0043 (5)	0.0015 (5)
C11	0.0117 (6)	0.0159 (7)	0.0139 (7)	0.0003 (5)	0.0016 (5)	0.0010 (5)
C12	0.0143 (7)	0.0290 (8)	0.0109 (7)	0.0033 (6)	0.0019 (5)	−0.0001 (6)
C13	0.0181 (7)	0.0171 (8)	0.0165 (7)	−0.0018 (6)	0.0044 (6)	−0.0002 (6)
C14	0.0238 (8)	0.0252 (8)	0.0135 (7)	−0.0032 (7)	0.0038 (6)	−0.0015 (6)
C15	0.0293 (9)	0.0179 (8)	0.0310 (10)	0.0028 (7)	0.0161 (8)	−0.0015 (7)

Mo1—O3	1.7001 (12)	C5—C9	1.415 (2)
Mo1—O4	1.7140 (12)	C5—H5A	0.9500
Mo1—O2	1.9533 (11)	C6—C7	1.405 (3)
Mo1—O1	1.9604 (11)	C6—H6A	0.9500
Mo1—N1	2.2500 (13)	C7—C8	1.376 (2)
Mo1—O5	2.3331 (12)	C7—H7A	0.9500
O1—C2	1.3334 (18)	C8—C10	1.421 (2)
O2—C13	1.433 (2)	C8—H8A	0.9500
O5—C15	1.420 (2)	C9—C10	1.418 (2)
O5—H5O	0.8499	C11—H11A	0.9500
N1—C11	1.2852 (19)	C12—C13	1.522 (2)
N1—C12	1.464 (2)	C12—H12A	0.9900
C1—C2	1.401 (2)	C12—H12B	0.9900
C1—C10	1.445 (2)	C13—C14	1.514 (2)
C1—C11	1.448 (2)	C13—H13A	1.0000
C2—C3	1.420 (2)	C14—H14A	0.9800
C3—C4	1.362 (2)	C14—H14B	0.9800
C3—H3A	0.9500	C14—H14C	0.9800
C4—C9	1.422 (2)	C15—H15A	0.9800
C4—H4A	0.9500	C15—H15B	0.9800
C5—C6	1.373 (2)	C15—H15C	0.9800
O3—Mo1—O4	106.65 (6)	C7—C6—H6A	120.3
O3—Mo1—O2	100.16 (6)	C8—C7—C6	120.91 (16)
O4—Mo1—O2	95.61 (5)	C8—C7—H7A	119.5
O3—Mo1—O1	95.98 (5)	C6—C7—H7A	119.5
O4—Mo1—O1	102.94 (5)	C7—C8—C10	120.96 (15)
O2—Mo1—O1	150.75 (5)	C7—C8—H8A	119.5
O3—Mo1—N1	93.16 (5)	C10—C8—H8A	119.5
O4—Mo1—N1	159.54 (5)	C5—C9—C10	119.88 (15)
O2—Mo1—N1	75.44 (5)	C5—C9—C4	120.82 (15)
O1—Mo1—N1	79.48 (5)	C10—C9—C4	119.25 (14)
O3—Mo1—O5	168.75 (5)	C9—C10—C8	117.79 (13)
O4—Mo1—O5	84.34 (5)	C9—C10—C1	119.36 (14)
O2—Mo1—O5	80.69 (4)	C8—C10—C1	122.80 (14)
O1—Mo1—O5	78.88 (4)	N1—C11—C1	124.35 (14)
N1—Mo1—O5	76.13 (5)	N1—C11—H11A	117.8
C2—O1—Mo1	133.87 (10)	C1—C11—H11A	117.8
C13—O2—Mo1	119.69 (9)	N1—C12—C13	106.52 (13)
C15—O5—Mo1	129.06 (10)	N1—C12—H12A	110.4
C15—O5—H5O	105.9	C13—C12—H12A	110.4
Mo1—O5—H5O	121.4	N1—C12—H12B	110.4
C11—N1—C12	120.05 (13)	C13—C12—H12B	110.4
C11—N1—Mo1	127.98 (11)	H12A—C12—H12B	108.6
C12—N1—Mo1	111.93 (9)	O2—C13—C14	110.47 (13)
C2—C1—C10	119.11 (14)	O2—C13—C12	106.65 (13)
C2—C1—C11	120.87 (13)	C14—C13—C12	112.07 (14)
C10—C1—C11	119.86 (13)	O2—C13—H13A	109.2
O1—C2—C1	123.69 (14)	C14—C13—H13A	109.2
O1—C2—C3	115.93 (14)	C12—C13—H13A	109.2
C1—C2—C3	120.34 (14)	C13—C14—H14A	109.5
C4—C3—C2	120.66 (15)	C13—C14—H14B	109.5
C4—C3—H3A	119.7	H14A—C14—H14B	109.5
C2—C3—H3A	119.7	C13—C14—H14C	109.5
C3—C4—C9	121.14 (15)	H14A—C14—H14C	109.5
C3—C4—H4A	119.4	H14B—C14—H14C	109.5
C9—C4—H4A	119.4	O5—C15—H15A	109.5
C6—C5—C9	121.00 (16)	O5—C15—H15B	109.5
C6—C5—H5A	119.5	H15A—C15—H15B	109.5
C9—C5—H5A	119.5	O5—C15—H15C	109.5
C5—C6—C7	119.43 (15)	H15A—C15—H15C	109.5
C5—C6—H6A	120.3	H15B—C15—H15C	109.5
O3—Mo1—O1—C2	57.22 (14)	O1—C2—C3—C4	−176.28 (15)
O4—Mo1—O1—C2	165.86 (14)	C1—C2—C3—C4	1.3 (2)
O2—Mo1—O1—C2	−66.15 (18)	C2—C3—C4—C9	−3.3 (3)
N1—Mo1—O1—C2	−34.90 (14)	C9—C5—C6—C7	0.3 (3)
O5—Mo1—O1—C2	−112.66 (14)	C5—C6—C7—C8	0.6 (3)
O3—Mo1—O2—C13	−66.97 (11)	C6—C7—C8—C10	0.0 (3)
O4—Mo1—O2—C13	−175.04 (11)	C6—C5—C9—C10	−1.6 (3)
O1—Mo1—O2—C13	55.48 (15)	C6—C5—C9—C4	175.93 (17)
N1—Mo1—O2—C13	23.68 (11)	C3—C4—C9—C5	−175.91 (16)
O5—Mo1—O2—C13	101.65 (11)	C3—C4—C9—C10	1.6 (2)
O3—Mo1—O5—C15	−43.8 (3)	C5—C9—C10—C8	2.1 (2)
O4—Mo1—O5—C15	124.28 (15)	C4—C9—C10—C8	−175.50 (15)
O2—Mo1—O5—C15	−139.07 (15)	C5—C9—C10—C1	179.57 (15)
O1—Mo1—O5—C15	19.88 (15)	C4—C9—C10—C1	2.0 (2)
N1—Mo1—O5—C15	−61.89 (15)	C7—C8—C10—C9	−1.3 (2)
O3—Mo1—N1—C11	−72.74 (14)	C7—C8—C10—C1	−178.68 (15)
O4—Mo1—N1—C11	121.60 (18)	C2—C1—C10—C9	−3.9 (2)
O2—Mo1—N1—C11	−172.43 (14)	C11—C1—C10—C9	171.46 (14)
O1—Mo1—N1—C11	22.76 (13)	C2—C1—C10—C8	173.43 (15)
O5—Mo1—N1—C11	103.77 (14)	C11—C1—C10—C8	−11.2 (2)
O3—Mo1—N1—C12	104.86 (11)	C12—N1—C11—C1	176.40 (15)
O4—Mo1—N1—C12	−60.8 (2)	Mo1—N1—C11—C1	−6.2 (2)
O2—Mo1—N1—C12	5.18 (10)	C2—C1—C11—N1	−13.1 (2)
O1—Mo1—N1—C12	−159.63 (11)	C10—C1—C11—N1	171.56 (15)
O5—Mo1—N1—C12	−78.62 (11)	C11—N1—C12—C13	148.93 (15)
Mo1—O1—C2—C1	29.3 (2)	Mo1—N1—C12—C13	−28.89 (15)
Mo1—O1—C2—C3	−153.24 (12)	Mo1—O2—C13—C14	−168.83 (10)
C10—C1—C2—O1	179.71 (14)	Mo1—O2—C13—C12	−46.80 (15)
C11—C1—C2—O1	4.4 (2)	N1—C12—C13—O2	45.45 (16)
C10—C1—C2—C3	2.3 (2)	N1—C12—C13—C14	166.45 (13)
C11—C1—C2—C3	−173.00 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5O···O2i	0.85	1.82	2.6667 (16)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5O⋯O2i	0.85	1.82	2.6667 (16)	179

Symmetry code: (i) .