{2,2′-[(2,2-Dimethyl­propane-1,3-di­yl)­bis­(nitrilo­methyl­idyne)]­diphenolato}­dioxidomolybdenum(VI)

Abbasi, A.; Sheikhshoaie, I.; Saghaei, A.; Monadi, N.

doi:10.1107/S160053680802182X

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page m1036

doi:10.1107/S160053680802182X

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{2,2′-[(2,2-Dimethylpropane-1,3-diyl)bis(nitrilomethylidyne)]diphenolato}dioxidomolybdenum(VI)

Alireza Abbasi,^a ^* Iran Sheikhshoaie,^b Abbas Saghaei ^c and Niaz Monadi ^b

^aSchool of Chemistry, University College of Science, University of Tehran, Iran, ^bChemistry Department, Shahid Bahonar University, Kerman, Iran, and ^cIslamic Azad University, Science and Research Branch, Tehran, Iran
^*Correspondence e-mail: aabbasi@khayam.ut.ac.ir

(Received 28 June 2008; accepted 13 July 2008; online 19 July 2008)

In the structure of the title compound, [Mo(C₁₉H₂₀N₂O₂)O₂], the Mo atom exhibits oxidation state +VI and is surrounded by two O atoms and the tetradentate Schiff base ligand 2,2′-[(2,2-dimethylpropane-1,3-diyl)bis(nitrilomethylidyne)]diphenolate in a distorted octahedral configuration. An intramolecular C—H⋯O hydrogen bond between a methylene group and one O atom of the O=Mo^VI=O unit, as well as additional intermolecular hydrogen bonds between neighboring molecules, lead to a weakly bonded inversion-symmetric dimeric structure.

Related literature

For related structures with O=Mo^VI=O units and for synthesis, see: Arnaiz et al. (2000 ); Holm et al. (1996 ); Syamal & Maurya (1989 ). The crystal structure of the free ligand N,N′-bis(2-hydroxybenzylidene)-2,2-dimethyl-1,3-propanediamine was described by Corden et al. (1996 ).

Experimental

Crystal data

[Mo(C₁₉H₂₀N₂O₂)O₂]
M_r = 436.31
Triclinic, $[P \overline 1]$
a = 9.3875 (10) Å
b = 9.5597 (10) Å
c = 11.0422 (11) Å
α = 104.6790 (17)°
β = 108.1939 (17)°
γ = 101.1218 (17)°
V = 869.87 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.78 mm⁻¹
T = 100 (2) K
0.18 × 0.12 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: none
8420 measured reflections
3413 independent reflections
3204 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.051
S = 1.07
3413 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Selected bond lengths (Å)

Mo1—O1	1.7072 (14)
Mo1—O2	1.7120 (14)
Mo1—O4	1.9373 (13)
Mo1—O3	2.0917 (14)
Mo1—N2	2.1442 (16)
Mo1—N1	2.3402 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O2	0.97	2.49	2.986 (2)	112
C1—H1⋯O1ⁱ	0.93	2.54	3.227 (2)	131
C4—H4B⋯O1ⁱ	0.97	2.56	3.294 (2)	132
C7—H7⋯O2ⁱ	0.93	2.55	3.315 (2)	140
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001 ); software used to prepare material for publication: PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680802182X/wm2183sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802182X/wm2183Isup2.hkl

checkCIF report

Comment top

Numerous chemical reactions are catalyzed by compounds containing complexes with the dioxidomolybdenum(VI) unit O═Mo^VI═O (Arnaiz et al. 2000). Moreover, Schiff base compounds containing molybdenum play a significant role in the chemistry of molybdoenzymes (Holm et al. 1996; Syamal & Maurya, 1989). Therefore we are interested in the structural chemistry of dioxidomolybdenum(VI) complexes and have synthesized and structurally characterized the title compound, MoO₂(C₁₉H₂₀N₂O₂), (I).

The molecular structure of (I) and the atom-numbering scheme are shown in Fig. 1. The molybdenum(VI) atom is in a distorted octahedral coordination by two oxygen atoms and one tetradentate ligand L, where L is N,N'-bis(2-hydroxybenzylidene)-2,2-dimethyl-1,3-propanediamine. The Mo–O distances of the oxido ligands are significantly shorter (average 1.71 Å) than the corresponding distances to the O atoms of the tetradentate ligand (average 2.02 Å). The Mo–N distances are the longest (average 2.24 Å). An intramolecular hydrogen bond is present between the methylene group and one O atom from the O═Mo═O group (C4—H41···O2, 2.985 Å). Much weaker intermolecular hydrogen bonds exist between neighboring molecules, leading to an dimer structure (see hydrogen bond Table and Fig. 2). For a packing plot of the structure, see Fig. 3. Resulting from the coordination of the tetradentate L ligand to the molybdenum ion, the chelate ligand is more twisted than the free ligand, with a larger dihedral angle between two phenyl rings of 75.2 (1)° compared to the free ligand with 68.7 (1)° (Corden et al., 1996).

Related literature top

For related structures with O═Mo^VI═O units and for synthesis, see: Arnaiz et al. (2000); Holm et al. (1996); Syamal & Maurya (1989). The crystal structure of the free ligand N,N'-bis(2-hydroxybenzylidene)-2,2-dimethyl-1,3-propanediamine was described by Corden et al. (1996).

Experimental top

The title compound was prepared by adding MoO₂(acac)₂ and the ligand H₂L (Corden et al., 1996) in the molar ratio 1:1 to 30 mL dry methanol, followed by refluxing the solution for 1 h. Small prismatic, yellowish crystals precipitated which were filtered off and recrystallized from acetonitrile to get a better crystal quality.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. Molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as circles of arbitrary radius. Hydrogen bonds are represented as dotted lines.
	Fig. 2. The inversion-symmetric dimeric structure of (I). Hydrogen bonds are represented as dotted lines.
	Fig. 3. Packing plot of (I) along [001].

{2,2'-[(2,2-Dimethylpropane-1,3- diyl)bis(nitrilomethylidyne)]diphenolato}dioxidomolybdenum(VI) top

Crystal data top

[Mo(C₁₉H₂₀N₂O₂)O₂]	Z = 2
M_r = 436.31	F(000) = 444
Triclinic, P1	D_x = 1.666 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3875 (10) Å	Cell parameters from 8420 reflections
b = 9.5597 (10) Å	θ = 2.5–26.0°
c = 11.0422 (11) Å	µ = 0.78 mm⁻¹
α = 104.6790 (17)°	T = 100 K
β = 108.1939 (17)°	Prism, light yellow
γ = 101.1218 (17)°	0.18 × 0.12 × 0.06 mm
V = 869.87 (16) Å³

Data collection top

Bruker APEXII CCD diffractometer	3204 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 26.0°, θ_min = 2.1°
ω scans	h = −11→11
8420 measured reflections	k = −11→11
3413 independent reflections	l = −13→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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.051	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0184P)² + 0.8169P] where P = (F_o² + 2F_c²)/3
3413 reflections	(Δ/σ)_max = 0.001
237 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Mo(C₁₉H₂₀N₂O₂)O₂]	γ = 101.1218 (17)°
M_r = 436.31	V = 869.87 (16) Å³
Triclinic, P1	Z = 2
a = 9.3875 (10) Å	Mo Kα radiation
b = 9.5597 (10) Å	µ = 0.78 mm⁻¹
c = 11.0422 (11) Å	T = 100 K
α = 104.6790 (17)°	0.18 × 0.12 × 0.06 mm
β = 108.1939 (17)°

Data collection top

Bruker APEXII CCD diffractometer	3204 reflections with I > 2σ(I)
8420 measured reflections	R_int = 0.020
3413 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.051	H-atom parameters constrained
S = 1.07	Δρ_max = 0.42 e Å⁻³
3413 reflections	Δρ_min = −0.53 e Å⁻³
237 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
Mo1	0.742950 (19)	0.625366 (18)	0.282813 (16)	0.01031 (6)
O1	0.70502 (16)	0.74204 (15)	0.19043 (14)	0.0161 (3)
O2	0.84039 (16)	0.52119 (16)	0.20730 (14)	0.0167 (3)
O3	0.59172 (16)	0.68583 (15)	0.37734 (13)	0.0135 (3)
O4	0.90918 (16)	0.76348 (15)	0.44982 (13)	0.0146 (3)
N1	0.75678 (18)	0.46531 (18)	0.41243 (16)	0.0115 (3)
N2	0.52861 (19)	0.44879 (18)	0.15515 (16)	0.0112 (3)
C1	0.3927 (2)	0.4737 (2)	0.11735 (19)	0.0127 (4)
H1	0.3111	0.3981	0.0443	0.015*
C2	0.7108 (2)	0.3002 (2)	0.34369 (19)	0.0122 (4)
H2A	0.7190	0.2512	0.4115	0.015*
H2B	0.7855	0.2782	0.3032	0.015*
C3	0.8231 (2)	0.5116 (2)	0.5423 (2)	0.0121 (4)
H3	0.8229	0.4382	0.5838	0.014*
C4	0.5301 (2)	0.2902 (2)	0.11404 (19)	0.0131 (4)
H4A	0.6177	0.2836	0.0863	0.016*
H4B	0.4339	0.2289	0.0375	0.016*
C5	0.4553 (2)	0.7013 (2)	0.3131 (2)	0.0127 (4)
C6	0.3575 (2)	0.6066 (2)	0.1779 (2)	0.0132 (4)
C7	0.2101 (2)	0.6264 (2)	0.1145 (2)	0.0156 (4)
H7	0.1467	0.5643	0.0262	0.019*
C8	0.1596 (2)	0.7357 (2)	0.1811 (2)	0.0188 (4)
H8	0.0631	0.7486	0.1380	0.023*
C9	0.2546 (3)	0.8278 (2)	0.3146 (2)	0.0189 (4)
H9	0.2204	0.9020	0.3600	0.023*
C10	0.3979 (2)	0.8102 (2)	0.3795 (2)	0.0161 (4)
H10	0.4579	0.8713	0.4688	0.019*
C11	0.9390 (2)	0.7870 (2)	0.58181 (19)	0.0122 (4)
C12	0.8984 (2)	0.6685 (2)	0.62999 (19)	0.0120 (4)
C13	0.9480 (2)	0.6997 (2)	0.7706 (2)	0.0139 (4)
H13	0.9255	0.6212	0.8035	0.017*
C14	1.0294 (2)	0.8440 (2)	0.8609 (2)	0.0154 (4)
H14	1.0595	0.8633	0.9536	0.019*
C15	1.0658 (2)	0.9608 (2)	0.8110 (2)	0.0156 (4)
H15	1.1204	1.0585	0.8712	0.019*
C16	1.0218 (2)	0.9330 (2)	0.6732 (2)	0.0143 (4)
H16	1.0473	1.0118	0.6414	0.017*
C17	0.5230 (2)	0.0591 (2)	0.1785 (2)	0.0166 (4)
H17A	0.5356	0.0183	0.2509	0.025*
H17B	0.5999	0.0428	0.1404	0.025*
H17C	0.4197	0.0095	0.1098	0.025*
C18	0.4199 (2)	0.2557 (2)	0.2899 (2)	0.0156 (4)
H18A	0.3185	0.2163	0.2174	0.023*
H18B	0.4408	0.3623	0.3329	0.023*
H18C	0.4216	0.2051	0.3549	0.023*
C19	0.5451 (2)	0.2294 (2)	0.23343 (19)	0.0119 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mo1	0.01067 (9)	0.01016 (9)	0.00976 (9)	0.00212 (6)	0.00322 (6)	0.00433 (6)
O1	0.0185 (7)	0.0120 (7)	0.0142 (7)	0.0015 (6)	0.0028 (6)	0.0051 (6)
O2	0.0143 (7)	0.0182 (7)	0.0193 (7)	0.0037 (6)	0.0090 (6)	0.0064 (6)
O3	0.0135 (7)	0.0145 (7)	0.0121 (7)	0.0054 (6)	0.0038 (5)	0.0046 (5)
O4	0.0148 (7)	0.0147 (7)	0.0117 (7)	0.0006 (6)	0.0026 (6)	0.0058 (6)
N1	0.0081 (8)	0.0116 (8)	0.0149 (8)	0.0030 (6)	0.0043 (6)	0.0046 (7)
N2	0.0139 (8)	0.0106 (8)	0.0093 (8)	0.0031 (6)	0.0052 (6)	0.0032 (6)
C1	0.0132 (10)	0.0134 (9)	0.0099 (9)	0.0013 (8)	0.0031 (7)	0.0047 (7)
C2	0.0116 (9)	0.0116 (9)	0.0150 (10)	0.0042 (8)	0.0053 (8)	0.0059 (8)
C3	0.0086 (9)	0.0135 (9)	0.0167 (10)	0.0037 (7)	0.0048 (8)	0.0090 (8)
C4	0.0152 (10)	0.0106 (9)	0.0114 (9)	0.0030 (8)	0.0045 (8)	0.0014 (7)
C5	0.0145 (10)	0.0123 (9)	0.0150 (10)	0.0036 (8)	0.0069 (8)	0.0088 (8)
C6	0.0137 (10)	0.0142 (9)	0.0148 (10)	0.0041 (8)	0.0070 (8)	0.0082 (8)
C7	0.0133 (10)	0.0184 (10)	0.0157 (10)	0.0035 (8)	0.0047 (8)	0.0083 (8)
C8	0.0161 (10)	0.0238 (11)	0.0253 (11)	0.0111 (9)	0.0100 (9)	0.0163 (9)
C9	0.0248 (12)	0.0181 (10)	0.0244 (11)	0.0123 (9)	0.0156 (9)	0.0121 (9)
C10	0.0220 (11)	0.0143 (10)	0.0141 (10)	0.0066 (8)	0.0084 (8)	0.0058 (8)
C11	0.0075 (9)	0.0169 (10)	0.0124 (9)	0.0052 (8)	0.0023 (7)	0.0059 (8)
C12	0.0078 (9)	0.0142 (9)	0.0148 (10)	0.0044 (7)	0.0041 (7)	0.0056 (8)
C13	0.0119 (10)	0.0173 (10)	0.0163 (10)	0.0060 (8)	0.0068 (8)	0.0091 (8)
C14	0.0140 (10)	0.0207 (10)	0.0110 (9)	0.0054 (8)	0.0045 (8)	0.0046 (8)
C15	0.0129 (10)	0.0139 (10)	0.0160 (10)	0.0035 (8)	0.0032 (8)	0.0019 (8)
C16	0.0127 (10)	0.0131 (10)	0.0181 (10)	0.0044 (8)	0.0043 (8)	0.0083 (8)
C17	0.0173 (10)	0.0122 (10)	0.0175 (10)	0.0026 (8)	0.0047 (8)	0.0042 (8)
C18	0.0131 (10)	0.0190 (10)	0.0168 (10)	0.0049 (8)	0.0067 (8)	0.0083 (8)
C19	0.0117 (9)	0.0098 (9)	0.0139 (9)	0.0021 (7)	0.0054 (8)	0.0035 (8)

Geometric parameters (Å, º) top

Mo1—O1	1.7072 (14)	C7—C8	1.370 (3)
Mo1—O2	1.7120 (14)	C7—H7	0.9300
Mo1—O4	1.9373 (13)	C8—C9	1.401 (3)
Mo1—O3	2.0917 (14)	C8—H8	0.9300
Mo1—N2	2.1442 (16)	C9—C10	1.378 (3)
Mo1—N1	2.3402 (16)	C9—H9	0.9300
O3—C5	1.313 (2)	C10—H10	0.9300
O4—C11	1.345 (2)	C11—C16	1.395 (3)
N1—C3	1.286 (2)	C11—C12	1.407 (3)
N1—C2	1.477 (2)	C12—C13	1.406 (3)
N2—C1	1.301 (3)	C13—C14	1.379 (3)
N2—C4	1.472 (2)	C13—H13	0.9300
C1—C6	1.428 (3)	C14—C15	1.395 (3)
C1—H1	0.9300	C14—H14	0.9300
C2—C19	1.534 (3)	C15—C16	1.385 (3)
C2—H2A	0.9700	C15—H15	0.9300
C2—H2B	0.9700	C16—H16	0.9300
C3—C12	1.454 (3)	C17—C19	1.534 (3)
C3—H3	0.9300	C17—H17A	0.9600
C4—C19	1.549 (3)	C17—H17B	0.9600
C4—H4A	0.9700	C17—H17C	0.9600
C4—H4B	0.9700	C18—C19	1.525 (3)
C5—C10	1.410 (3)	C18—H18A	0.9600
C5—C6	1.425 (3)	C18—H18B	0.9600
C6—C7	1.415 (3)	C18—H18C	0.9600

O1—Mo1—O2	103.33 (7)	C8—C7—H7	119.5
O1—Mo1—O4	101.99 (6)	C6—C7—H7	119.5
O2—Mo1—O4	102.79 (6)	C7—C8—C9	119.36 (19)
O1—Mo1—O3	90.82 (6)	C7—C8—H8	120.3
O2—Mo1—O3	161.79 (6)	C9—C8—H8	120.3
O4—Mo1—O3	85.05 (6)	C10—C9—C8	120.94 (19)
O1—Mo1—N2	93.87 (6)	C10—C9—H9	119.5
O2—Mo1—N2	88.54 (6)	C8—C9—H9	119.5
O4—Mo1—N2	157.64 (6)	C9—C10—C5	121.24 (19)
O3—Mo1—N2	79.01 (6)	C9—C10—H10	119.4
O1—Mo1—N1	170.94 (6)	C5—C10—H10	119.4
O2—Mo1—N1	84.17 (6)	O4—C11—C16	117.93 (17)
O4—Mo1—N1	80.95 (6)	O4—C11—C12	122.15 (17)
O3—Mo1—N1	80.84 (5)	C16—C11—C12	119.80 (18)
N2—Mo1—N1	81.12 (6)	C13—C12—C11	118.62 (18)
C5—O3—Mo1	123.46 (12)	C13—C12—C3	117.94 (17)
C11—O4—Mo1	134.29 (12)	C11—C12—C3	123.05 (17)
C3—N1—C2	115.90 (16)	C14—C13—C12	121.52 (18)
C3—N1—Mo1	124.12 (13)	C14—C13—H13	119.2
C2—N1—Mo1	119.23 (12)	C12—C13—H13	119.2
C1—N2—C4	117.18 (16)	C13—C14—C15	118.99 (18)
C1—N2—Mo1	122.83 (13)	C13—C14—H14	120.5
C4—N2—Mo1	119.87 (12)	C15—C14—H14	120.5
N2—C1—C6	125.94 (18)	C16—C15—C14	120.85 (19)
N2—C1—H1	117.0	C16—C15—H15	119.6
C6—C1—H1	117.0	C14—C15—H15	119.6
N1—C2—C19	115.73 (15)	C15—C16—C11	120.17 (18)
N1—C2—H2A	108.3	C15—C16—H16	119.9
C19—C2—H2A	108.3	C11—C16—H16	119.9
N1—C2—H2B	108.3	C19—C17—H17A	109.5
C19—C2—H2B	108.3	C19—C17—H17B	109.5
H2A—C2—H2B	107.4	H17A—C17—H17B	109.5
N1—C3—C12	125.78 (17)	C19—C17—H17C	109.5
N1—C3—H3	117.1	H17A—C17—H17C	109.5
C12—C3—H3	117.1	H17B—C17—H17C	109.5
N2—C4—C19	110.04 (15)	C19—C18—H18A	109.5
N2—C4—H4A	109.7	C19—C18—H18B	109.5
C19—C4—H4A	109.7	H18A—C18—H18B	109.5
N2—C4—H4B	109.7	C19—C18—H18C	109.5
C19—C4—H4B	109.7	H18A—C18—H18C	109.5
H4A—C4—H4B	108.2	H18B—C18—H18C	109.5
O3—C5—C10	120.15 (18)	C18—C19—C2	111.61 (16)
O3—C5—C6	122.19 (18)	C18—C19—C17	109.71 (16)
C10—C5—C6	117.62 (18)	C2—C19—C17	106.47 (16)
C7—C6—C5	119.77 (18)	C18—C19—C4	110.70 (16)
C7—C6—C1	119.37 (18)	C2—C19—C4	110.88 (15)
C5—C6—C1	119.60 (17)	C17—C19—C4	107.29 (15)
C8—C7—C6	121.04 (19)

O1—Mo1—O3—C5	41.55 (15)	Mo1—O3—C5—C10	−146.68 (14)
O2—Mo1—O3—C5	−99.9 (2)	Mo1—O3—C5—C6	35.9 (2)
O4—Mo1—O3—C5	143.51 (15)	O3—C5—C6—C7	178.78 (17)
N2—Mo1—O3—C5	−52.23 (14)	C10—C5—C6—C7	1.3 (3)
N1—Mo1—O3—C5	−134.88 (15)	O3—C5—C6—C1	11.6 (3)
O1—Mo1—O4—C11	135.68 (17)	C10—C5—C6—C1	−165.83 (18)
O2—Mo1—O4—C11	−117.46 (17)	N2—C1—C6—C7	171.47 (18)
O3—Mo1—O4—C11	45.89 (17)	N2—C1—C6—C5	−21.3 (3)
N2—Mo1—O4—C11	1.4 (3)	C5—C6—C7—C8	0.1 (3)
N1—Mo1—O4—C11	−35.61 (17)	C1—C6—C7—C8	167.25 (19)
O2—Mo1—N1—C3	121.32 (16)	C6—C7—C8—C9	−0.8 (3)
O4—Mo1—N1—C3	17.34 (15)	C7—C8—C9—C10	0.1 (3)
O3—Mo1—N1—C3	−69.06 (15)	C8—C9—C10—C5	1.3 (3)
N2—Mo1—N1—C3	−149.25 (16)	O3—C5—C10—C9	−179.54 (18)
O2—Mo1—N1—C2	−48.30 (13)	C6—C5—C10—C9	−2.0 (3)
O4—Mo1—N1—C2	−152.29 (13)	Mo1—O4—C11—C16	−150.25 (15)
O3—Mo1—N1—C2	121.32 (13)	Mo1—O4—C11—C12	33.8 (3)
N2—Mo1—N1—C2	41.12 (13)	O4—C11—C12—C13	173.48 (17)
O1—Mo1—N2—C1	−48.07 (15)	C16—C11—C12—C13	−2.4 (3)
O2—Mo1—N2—C1	−151.34 (15)	O4—C11—C12—C3	0.8 (3)
O4—Mo1—N2—C1	87.3 (2)	C16—C11—C12—C3	−175.13 (18)
O3—Mo1—N2—C1	42.02 (15)	N1—C3—C12—C13	172.40 (18)
N1—Mo1—N2—C1	124.33 (15)	N1—C3—C12—C11	−14.9 (3)
O1—Mo1—N2—C4	136.02 (13)	C11—C12—C13—C14	2.7 (3)
O2—Mo1—N2—C4	32.75 (14)	C3—C12—C13—C14	175.75 (18)
O4—Mo1—N2—C4	−88.6 (2)	C12—C13—C14—C15	−1.4 (3)
O3—Mo1—N2—C4	−133.89 (14)	C13—C14—C15—C16	−0.2 (3)
N1—Mo1—N2—C4	−51.57 (13)	C14—C15—C16—C11	0.4 (3)
C4—N2—C1—C6	159.34 (18)	O4—C11—C16—C15	−175.12 (17)
Mo1—N2—C1—C6	−16.7 (3)	C12—C11—C16—C15	1.0 (3)
C3—N1—C2—C19	133.97 (18)	N1—C2—C19—C18	−59.5 (2)
Mo1—N1—C2—C19	−55.57 (19)	N1—C2—C19—C17	−179.21 (16)
C2—N1—C3—C12	170.57 (17)	N1—C2—C19—C4	64.4 (2)
Mo1—N1—C3—C12	0.6 (3)	N2—C4—C19—C18	52.6 (2)
C1—N2—C4—C19	−100.26 (19)	N2—C4—C19—C2	−71.82 (19)
Mo1—N2—C4—C19	75.87 (17)	N2—C4—C19—C17	172.30 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O2	0.97	2.49	2.986 (2)	112
C1—H1···O1ⁱ	0.93	2.54	3.227 (2)	131
C4—H4B···O1ⁱ	0.97	2.56	3.294 (2)	132
C7—H7···O2ⁱ	0.93	2.55	3.315 (2)	140

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Mo(C₁₉H₂₀N₂O₂)O₂]
M_r	436.31
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.3875 (10), 9.5597 (10), 11.0422 (11)
α, β, γ (°)	104.6790 (17), 108.1939 (17), 101.1218 (17)
V (Å³)	869.87 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.78
Crystal size (mm)	0.18 × 0.12 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8420, 3413, 3204
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.051, 1.07
No. of reflections	3413
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.53

Computer programs: APEX2 (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2001), PLATON (Spek, 2003).

Selected bond lengths (Å) top

Mo1—O1	1.7072 (14)	Mo1—O3	2.0917 (14)
Mo1—O2	1.7120 (14)	Mo1—N2	2.1442 (16)
Mo1—O4	1.9373 (13)	Mo1—N1	2.3402 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O2	0.97	2.49	2.986 (2)	111.5
C1—H1···O1ⁱ	0.93	2.54	3.227 (2)	131.0
C4—H4B···O1ⁱ	0.97	2.56	3.294 (2)	132.4
C7—H7···O2ⁱ	0.93	2.55	3.315 (2)	139.9

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

This work was supported by grants from the University of Kerman and the University of Tehran.

References

Arnaiz, F. J., Aguado, R., Pedrosa, M. R., De Cian, A. & Fischer, A. (2000). Polyhedron, 19, 2141–2147. Web of Science CSD CrossRef CAS Google Scholar
Brandenburg, K. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Corden, J. P., Errington, W., Moore, P. & Wallbridge, M. G. H. (1996). Acta Cryst. C52, 125–127. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Holm, R. H., Kennepohl, P. & Solomon, E. I. (1996). Chem. Rev. 96, 2239–2314. CrossRef PubMed CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Syamal, A. & Maurya, M. R. (1989). Coord. Chem. Rev. 95, 183–238. CrossRef CAS Web of Science Google Scholar

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Volume 64| Part 8| August 2008| Page m1036

doi:10.1107/S160053680802182X

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{2,2′-[(2,2-Di­methyl­propane-1,3-di­yl)­bis­­(nitrilo­methyl­­idyne)]­diphenolato}­dioxidomolybdenum(VI)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{2,2′-[(2,2-Dimethylpropane-1,3-diyl)bis(nitrilomethylidyne)]diphenolato}dioxidomolybdenum(VI)