{1,1′-[(2,2-Dimethyl­propane-1,3-di­yl)bis­(nitrilo­methyl­idyne)]di-2-naphthol­ato}dioxidomolybdenum(VI) dichloro­methane 1.75-solvate

Monadi, N.; Sheikhshoaie, I.; Rezaeifard, A.; Stoeckli-Evans, H.

doi:10.1107/S1600536809032759

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages m1124-m1125

doi:10.1107/S1600536809032759

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{1,1′-[(2,2-Dimethylpropane-1,3-diyl)bis(nitrilomethylidyne)]di-2-naphtholato}dioxidomolybdenum(VI) dichloromethane 1.75-solvate

Niaz Monadi,^a Iran Sheikhshoaie,^a ^* Abdoreza Rezaeifard ^b and Helen Stoeckli-Evans ^c

^aChemistry Department, Shahid Bahonar University of Kerman, Kerman, Iran, ^bChemistry Department, Birjand University, Birjand, Iran, and ^cInstitute of Physics, University of Neuchâtel, Rue Emile-Argand 11, CH-2009 Neuchâtel, Switzerland
^*Correspondence e-mail: i_shoaie@yahoo.com

(Received 11 August 2009; accepted 17 August 2009; online 22 August 2009)

In the crystal structure of the title compound, [Mo(C₂₇H₂₄N₂O₂)O₂]·1.75CH₂Cl₂, the Mo^VI ion is coordinated by two oxide O atoms and by two O and two N atoms of the tetradentate 1,1′-[(2,2-dimethylpropane-1,3-diyl)bis(nitrilomethylidyne)]di-2-naphtholate Schiff base ligand in a distorted octahedral configuration. The compound crystallizes with 1.75 molecules of dichloromethane per complex molecule. In the crystal, symmetry-related molecules are linked by a number of C—H⋯O interactions involving both the Schiff base ligand and the partly disordered dichloromethane solvent molecules, leading to the formation of a two-dimensional network extending parallel to (101).

Related literature

For the chemistry of molybdenum(VI)–Schiff base complexes and related structures with O=Mo=O units (metal oxidation state +VI), see: Abbasi et al. (2008 ); Arnaiz et al. (2000 ); Holm et al. (1996 ); Maurya et al. (1997 ); Nakayima et al. (1998 ); Rao et al. (1998 ); Sheikhshoaie et al. (2009 ); Syamal & Maurya (1989 ).

Experimental

Crystal data

[Mo(C₂₇H₂₄N₂O₂)O₂]·1.75CH₂Cl₂
M_r = 685.04
Monoclinic, C 2/c
a = 27.6049 (18) Å
b = 10.7743 (8) Å
c = 21.6474 (14) Å
β = 112.861 (7)°
V = 5932.7 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.79 mm⁻¹
T = 173 K
0.38 × 0.23 × 0.18 mm

Data collection

Stoe IPDS diffractometer
Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009 ) T_min = 0.833, T_max = 0.864
21863 measured reflections
5537 independent reflections
4789 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.106
S = 1.12
5537 reflections
372 parameters
H-atom parameters constrained
Δρ_max = 1.08 e Å⁻³
Δρ_min = −0.83 e Å⁻³

Table 1
Selected bond lengths (Å)

Mo1—O1	2.0888 (19)
Mo1—O2	1.957 (2)
Mo1—O3	1.702 (2)
Mo1—O4	1.713 (2)
Mo1—N1	2.118 (2)
Mo1—N2	2.297 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3ⁱ	0.95	2.43	3.328 (5)	159
C11—H11⋯O4ⁱⁱ	0.95	2.38	3.297 (3)	161
C12—H12A⋯O4	0.99	2.47	2.974 (4)	111
C27—H27A⋯O3ⁱⁱ	0.98	2.55	3.490 (4)	161
C28—H28A⋯O2ⁱⁱⁱ	0.99	2.40	3.213 (5)	139
C28—H28A⋯O4ⁱⁱⁱ	0.99	2.53	3.429 (6)	151
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y-1, z.

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809032759/wm2248sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032759/wm2248Isup2.hkl

checkCIF report

Comment top

Numerous molybdenum(VI) Schiff base complexes have been extensively investigated for over the past twenty years, due to their importance in the domains of stereochemistry (Maurya et al., 1997), structural chemistry (Nakayima, et al., 1998; Syamal & Maurya, 1989), analytical chemistry (Rao et al., 1998), bioinorganic chemistry (Holm et al., 1996), and oxidation catalysis (Abbasi et al., 2008; Arnaiz et al., 2000; Sheikhshoaie et al., 2009). Continuing our interest in the structural chemistry of dioxidomolybdenum(VI) Schiff base complexes, we have synthesized and structurally characterized the title compound.

The molecular structure of the title complex is illustrated in Fig. 1, and geometrical parameters are available in the archived CIF. The Mo^VI atom is in a distorted octahedral environment being coordinated by two oxido O atoms (O1 and O2) and four atoms (two oxygen and two nitrogen atoms) of the tetradentate Schiff base ligand 1,1'-[(2,2-dimethylpropane-1,3-diyl)bis(nitrilomethylidyne)]di-2-naphtholate. The Mo—O distances of the oxido ligands (Mo1O3 and Mo1O4) are significantly shorter [1.702 (2) and 1.713 (2) Å, respectively] than the corresponding Mo—O distances to the O-atoms (O2 and O1) of the tetradentate Schiff base ligand, 1.957 (2) and 2.0888 (19) Å, respectively. The Mo—N distances, to atoms N1 and N2, are even longer being 2.118 (2) and 2.297 (2) Å, respectively.

In the crystal, molecules are linked by a number of C—H···O interactions, involving both the Schiff base ligand and the solvent molecules of crystallization, leading to the formation of a two-dimensional network extending in the (101) plane (Table 1 and Fig. 2).

Related literature top

For the chemistry of molybdenum(VI)–Schiff base complexes and related structures with O═Mo═O units (metal oxidation state +VI), see: Abbasi et al. (2008); Arnaiz et al. (2000); Holm et al. (1996); Maurya et al. (1997); Nakayima et al. (1998); Rao et al. (1998); Sheikhshoaie et al. (2009); Syamal & Maurya (1989).

Experimental top

The title dioxidomolybdenum (VI) complex was prepared by mixing MoO₂(acac)₂ with the ligand, 2,2'-[(2,2-dimethylpropane-1,3-diyl)bis(nitrilomethylidyne)]-dinaphtholate, in a 1:1 molar ratio using 25 ml of dry methanol as solvent, followed by refluxing the solution for 3 h. The small reddish crystals that formed were filtered off and recrystallized from dichloromethane.

Computing details top

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

Figures top

	Fig. 1. A view of the molecular structure of the title complex, with the thermal ellipsoids drawn at the 50% probability level. The dichloromethane molecules of crystallization have been omitted for clarity.
	Fig. 2. A view along the b axis of the crystal packing of the title complex. The H-atoms not involved in C—H···O interactions (dotted blue lines) were omitted for clarity.

{1,1'-[(2,2-Dimethylpropane-1,3-diyl)bis(nitrilomethylidyne)]di-2- naphtholato}dioxidomolybdenum(VI) dichloromethane 1.75-solvate top

Crystal data top

[Mo(C₂₇H₂₄N₂O₂)O₂]·1.75CH₂Cl₂	F(000) = 2780
M_r = 685.04	D_x = 1.534 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7998 reflections
a = 27.6049 (18) Å	θ = 2.0–26.1°
b = 10.7743 (8) Å	µ = 0.79 mm⁻¹
c = 21.6474 (14) Å	T = 173 K
β = 112.861 (7)°	Block, red
V = 5932.7 (7) Å³	0.38 × 0.23 × 0.18 mm
Z = 8

Data collection top

Stoe IPDS diffractometer	5537 independent reflections
Radiation source: fine-focus sealed tube	4789 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ rotation scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009)	h = −33→33
T_min = 0.833, T_max = 0.864	k = −13→13
21863 measured reflections	l = −26→26

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0575P)² + 13.6226P] where P = (F_o² + 2F_c²)/3
5537 reflections	(Δ/σ)_max = 0.001
372 parameters	Δρ_max = 1.08 e Å⁻³
0 restraints	Δρ_min = −0.83 e Å⁻³

Crystal data top

[Mo(C₂₇H₂₄N₂O₂)O₂]·1.75CH₂Cl₂	V = 5932.7 (7) Å³
M_r = 685.04	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 27.6049 (18) Å	µ = 0.79 mm⁻¹
b = 10.7743 (8) Å	T = 173 K
c = 21.6474 (14) Å	0.38 × 0.23 × 0.18 mm
β = 112.861 (7)°

Data collection top

Stoe IPDS diffractometer	5537 independent reflections
Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009)	4789 reflections with I > 2σ(I)
T_min = 0.833, T_max = 0.864	R_int = 0.024
21863 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0575P)² + 13.6226P] where P = (F_o² + 2F_c²)/3
5537 reflections	Δρ_max = 1.08 e Å⁻³
372 parameters	Δρ_min = −0.83 e Å⁻³

Special details top

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

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Mo1	0.15195 (1)	0.99201 (2)	0.16605 (1)	0.0203 (1)
O1	0.11880 (7)	0.83854 (17)	0.10537 (10)	0.0244 (5)
O2	0.07965 (7)	1.05359 (17)	0.13420 (10)	0.0243 (5)
O3	0.17351 (8)	1.04666 (19)	0.10747 (10)	0.0294 (6)
O4	0.18137 (8)	1.08694 (18)	0.23387 (10)	0.0292 (6)
N1	0.21210 (9)	0.8581 (2)	0.20744 (11)	0.0230 (7)
N2	0.11991 (9)	0.8840 (2)	0.23353 (11)	0.0226 (6)
C1	0.14254 (11)	0.7716 (2)	0.07556 (14)	0.0240 (8)
C2	0.11155 (12)	0.7170 (3)	0.01261 (15)	0.0320 (9)
C3	0.13435 (13)	0.6494 (3)	−0.02156 (16)	0.0351 (9)
C4	0.18908 (13)	0.6260 (3)	0.00395 (15)	0.0297 (9)
C5	0.21229 (15)	0.5592 (3)	−0.03334 (16)	0.0359 (10)
C6	0.26506 (15)	0.5380 (3)	−0.00885 (17)	0.0378 (10)
C7	0.29652 (14)	0.5838 (3)	0.05388 (18)	0.0373 (10)
C8	0.27554 (13)	0.6506 (3)	0.09176 (16)	0.0312 (9)
C9	0.22085 (12)	0.6729 (2)	0.06788 (14)	0.0258 (8)
C10	0.19693 (11)	0.7471 (2)	0.10402 (14)	0.0240 (8)
C11	0.22523 (11)	0.7765 (2)	0.17248 (14)	0.0236 (8)
C12	0.23835 (11)	0.8489 (3)	0.28089 (14)	0.0259 (8)
C13	0.20409 (11)	0.7852 (3)	0.31281 (14)	0.0264 (8)
C14	0.15487 (11)	0.8626 (3)	0.30383 (14)	0.0265 (8)
C15	0.07193 (11)	0.8512 (2)	0.21471 (14)	0.0243 (8)
C16	0.03019 (11)	0.8852 (3)	0.15189 (14)	0.0237 (8)
C17	−0.01851 (11)	0.8180 (3)	0.12751 (14)	0.0258 (8)
C18	−0.02482 (13)	0.7013 (3)	0.15323 (16)	0.0317 (9)
C19	−0.07116 (14)	0.6372 (3)	0.12614 (18)	0.0396 (11)
C20	−0.11356 (13)	0.6855 (3)	0.07190 (19)	0.0412 (11)
C21	−0.10943 (12)	0.7981 (3)	0.04577 (16)	0.0347 (9)
C22	−0.06213 (11)	0.8663 (3)	0.07250 (15)	0.0277 (8)
C23	−0.05656 (12)	0.9810 (3)	0.04395 (16)	0.0311 (9)
C24	−0.00985 (11)	1.0411 (3)	0.06555 (15)	0.0276 (8)
C25	0.03480 (11)	0.9914 (2)	0.11817 (15)	0.0231 (8)
C26	0.18840 (13)	0.6549 (3)	0.28459 (17)	0.0347 (9)
C27	0.23717 (13)	0.7789 (3)	0.38843 (15)	0.0342 (9)
Cl1A	0.11134 (12)	0.36651 (18)	0.28031 (10)	0.1016 (8)	0.800
Cl2	0.06716 (6)	0.14580 (16)	0.31642 (8)	0.0913 (6)
C28	0.0768 (2)	0.2286 (5)	0.2529 (2)	0.0657 (17)
Cl1B	0.0605 (5)	0.3839 (7)	0.2649 (4)	0.102 (4)	0.200
Cl3	0.02059 (6)	0.4230 (2)	0.09019 (10)	0.0919 (8)	0.750
Cl4	0.13068 (6)	0.4167 (3)	0.11352 (11)	0.0993 (8)	0.750
C29	0.0693 (3)	0.3744 (8)	0.0643 (4)	0.088 (3)	0.750
H2	0.07450	0.72800	−0.00560	0.0380*
H3	0.11280	0.61660	−0.06420	0.0420*
H5	0.19070	0.52830	−0.07640	0.0430*
H6	0.28020	0.49240	−0.03440	0.0450*
H7	0.33330	0.56880	0.07100	0.0450*
H8	0.29800	0.68190	0.13430	0.0370*
H11	0.25700	0.73220	0.19510	0.0280*
H12A	0.24750	0.93330	0.29990	0.0310*
H12B	0.27150	0.80150	0.29240	0.0310*
H14A	0.13480	0.81950	0.32670	0.0320*
H14B	0.16620	0.94380	0.32610	0.0320*
H15	0.06280	0.80030	0.24440	0.0290*
H18	0.00360	0.66670	0.19000	0.0380*
H19	−0.07450	0.55900	0.14440	0.0480*
H20	−0.14540	0.63980	0.05320	0.0490*
H21	−0.13860	0.83090	0.00930	0.0420*
H23	−0.08610	1.01640	0.00910	0.0370*
H24	−0.00690	1.11740	0.04530	0.0330*
H26A	0.22010	0.60530	0.29290	0.0520*
H26B	0.16780	0.65990	0.23620	0.0520*
H26C	0.16720	0.61560	0.30650	0.0520*
H27A	0.26850	0.72800	0.39650	0.0510*
H27B	0.24790	0.86290	0.40570	0.0510*
H27C	0.21620	0.74190	0.41130	0.0510*
H28A	0.09620	0.17560	0.23290	0.0790*	0.800
H28B	0.04210	0.24780	0.21730	0.0790*	0.800
H28C	0.11240	0.21750	0.25530	0.0790*	0.200
H28D	0.05230	0.20120	0.20920	0.0790*	0.200
H29A	0.06810	0.28270	0.06100	0.1060*	0.750
H29B	0.06140	0.40740	0.01870	0.1060*	0.750

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mo1	0.0189 (1)	0.0204 (1)	0.0216 (1)	−0.0010 (1)	0.0080 (1)	−0.0015 (1)
O1	0.0227 (9)	0.0256 (9)	0.0249 (10)	−0.0011 (7)	0.0092 (8)	−0.0046 (7)
O2	0.0215 (9)	0.0231 (9)	0.0287 (10)	0.0001 (7)	0.0103 (8)	0.0010 (8)
O3	0.0272 (10)	0.0320 (11)	0.0308 (11)	−0.0018 (8)	0.0133 (9)	0.0012 (8)
O4	0.0278 (10)	0.0257 (10)	0.0315 (11)	−0.0013 (8)	0.0086 (9)	−0.0053 (8)
N1	0.0193 (11)	0.0271 (12)	0.0220 (11)	0.0005 (9)	0.0074 (9)	−0.0015 (9)
N2	0.0246 (11)	0.0235 (11)	0.0205 (11)	0.0036 (9)	0.0097 (10)	0.0005 (9)
C1	0.0292 (14)	0.0198 (12)	0.0249 (13)	−0.0016 (10)	0.0127 (12)	0.0000 (10)
C2	0.0312 (15)	0.0290 (15)	0.0301 (15)	0.0010 (12)	0.0058 (13)	−0.0057 (12)
C3	0.0465 (18)	0.0275 (15)	0.0261 (15)	−0.0007 (13)	0.0086 (14)	−0.0046 (11)
C4	0.0446 (17)	0.0215 (13)	0.0280 (14)	−0.0004 (12)	0.0196 (14)	0.0005 (11)
C5	0.060 (2)	0.0229 (14)	0.0318 (16)	−0.0016 (13)	0.0254 (16)	−0.0004 (12)
C6	0.062 (2)	0.0243 (14)	0.0428 (18)	0.0024 (14)	0.0375 (18)	0.0004 (13)
C7	0.0467 (19)	0.0271 (15)	0.0501 (19)	0.0051 (13)	0.0318 (17)	0.0059 (13)
C8	0.0372 (16)	0.0276 (14)	0.0352 (16)	0.0024 (12)	0.0212 (14)	0.0019 (12)
C9	0.0358 (15)	0.0181 (12)	0.0290 (14)	0.0015 (11)	0.0186 (13)	0.0029 (10)
C10	0.0277 (14)	0.0205 (12)	0.0243 (13)	−0.0003 (10)	0.0107 (12)	0.0001 (10)
C11	0.0215 (13)	0.0247 (13)	0.0278 (14)	0.0021 (10)	0.0132 (12)	0.0015 (10)
C12	0.0224 (13)	0.0310 (14)	0.0203 (13)	0.0046 (11)	0.0038 (11)	−0.0023 (11)
C13	0.0263 (14)	0.0291 (14)	0.0221 (13)	0.0048 (11)	0.0077 (12)	−0.0005 (11)
C14	0.0271 (14)	0.0318 (14)	0.0206 (13)	0.0033 (11)	0.0094 (12)	0.0012 (11)
C15	0.0267 (14)	0.0241 (13)	0.0257 (14)	0.0008 (10)	0.0141 (12)	0.0019 (10)
C16	0.0222 (13)	0.0257 (13)	0.0243 (13)	0.0024 (10)	0.0104 (11)	−0.0016 (10)
C17	0.0267 (14)	0.0285 (14)	0.0252 (14)	−0.0004 (11)	0.0133 (12)	−0.0051 (11)
C18	0.0350 (16)	0.0318 (15)	0.0327 (16)	−0.0036 (12)	0.0180 (14)	−0.0024 (12)
C19	0.0454 (19)	0.0353 (17)	0.0453 (19)	−0.0133 (14)	0.0254 (17)	−0.0073 (14)
C20	0.0330 (17)	0.0463 (19)	0.0472 (19)	−0.0173 (14)	0.0188 (16)	−0.0143 (15)
C21	0.0243 (14)	0.0477 (18)	0.0331 (16)	−0.0042 (13)	0.0121 (13)	−0.0106 (14)
C22	0.0216 (13)	0.0359 (15)	0.0274 (14)	−0.0016 (11)	0.0116 (12)	−0.0072 (12)
C23	0.0238 (14)	0.0383 (16)	0.0279 (15)	0.0042 (12)	0.0065 (13)	−0.0009 (12)
C24	0.0261 (14)	0.0284 (14)	0.0283 (14)	0.0043 (11)	0.0106 (12)	0.0036 (11)
C25	0.0209 (13)	0.0230 (13)	0.0263 (14)	0.0011 (10)	0.0101 (12)	−0.0035 (10)
C26	0.0378 (17)	0.0294 (15)	0.0369 (17)	0.0023 (13)	0.0145 (14)	0.0008 (12)
C27	0.0332 (16)	0.0433 (18)	0.0248 (15)	0.0124 (13)	0.0097 (13)	0.0043 (12)
Cl1A	0.150 (2)	0.0683 (11)	0.0748 (11)	−0.0216 (12)	0.0309 (13)	−0.0188 (9)
Cl2	0.0686 (8)	0.1124 (12)	0.0813 (9)	0.0082 (8)	0.0163 (7)	0.0270 (8)
C28	0.067 (3)	0.073 (3)	0.064 (3)	−0.009 (2)	0.033 (2)	−0.027 (2)
Cl1B	0.166 (9)	0.060 (4)	0.073 (4)	0.011 (5)	0.040 (5)	−0.022 (3)
Cl3	0.0444 (8)	0.150 (2)	0.0799 (12)	0.0113 (10)	0.0225 (8)	−0.0222 (12)
Cl4	0.0402 (8)	0.157 (2)	0.0875 (13)	0.0037 (10)	0.0105 (8)	0.0133 (13)
C29	0.057 (4)	0.114 (6)	0.100 (6)	−0.009 (4)	0.038 (4)	−0.048 (5)

Geometric parameters (Å, º) top

Mo1—O1	2.0888 (19)	C18—C19	1.369 (5)
Mo1—O2	1.957 (2)	C19—C20	1.397 (5)
Mo1—O3	1.702 (2)	C20—C21	1.362 (5)
Mo1—O4	1.713 (2)	C21—C22	1.412 (5)
Mo1—N1	2.118 (2)	C22—C23	1.417 (5)
Mo1—N2	2.297 (2)	C23—C24	1.354 (5)
Cl1A—C28	1.741 (6)	C24—C25	1.419 (4)
Cl1B—C28	1.778 (10)	C2—H2	0.9500
Cl2—C28	1.744 (5)	C3—H3	0.9500
Cl3—C29	1.727 (9)	C5—H5	0.9500
Cl4—C29	1.677 (9)	C6—H6	0.9500
O1—C1	1.302 (3)	C7—H7	0.9500
O2—C25	1.330 (4)	C8—H8	0.9500
N1—C12	1.472 (4)	C11—H11	0.9500
N1—C11	1.300 (4)	C12—H12A	0.9900
N2—C14	1.470 (4)	C12—H12B	0.9900
N2—C15	1.275 (4)	C14—H14B	0.9900
C1—C10	1.409 (4)	C14—H14A	0.9900
C1—C2	1.425 (4)	C15—H15	0.9500
C2—C3	1.355 (5)	C18—H18	0.9500
C3—C4	1.415 (5)	C19—H19	0.9500
C4—C5	1.408 (5)	C20—H20	0.9500
C4—C9	1.413 (4)	C21—H21	0.9500
C5—C6	1.362 (6)	C23—H23	0.9500
C6—C7	1.388 (5)	C24—H24	0.9500
C7—C8	1.377 (5)	C26—H26C	0.9800
C8—C9	1.413 (5)	C26—H26B	0.9800
C9—C10	1.445 (4)	C26—H26A	0.9800
C10—C11	1.417 (4)	C27—H27A	0.9800
C12—C13	1.533 (4)	C27—H27B	0.9800
C13—C26	1.525 (5)	C27—H27C	0.9800
C13—C27	1.535 (4)	C28—H28A	0.9900
C13—C14	1.541 (5)	C28—H28D	0.9700
C15—C16	1.447 (4)	C28—H28B	0.9900
C16—C25	1.389 (4)	C28—H28C	0.9700
C16—C17	1.435 (5)	C29—H29A	0.9900
C17—C18	1.413 (5)	C29—H29B	0.9900
C17—C22	1.423 (4)

O1—Mo1—O2	84.79 (8)	C1—C2—H2	120.00
O1—Mo1—O3	90.00 (9)	C3—C2—H2	120.00
O1—Mo1—O4	163.25 (9)	C2—C3—H3	119.00
O1—Mo1—N1	78.85 (8)	C4—C3—H3	119.00
O1—Mo1—N2	79.39 (8)	C4—C5—H5	119.00
O2—Mo1—O3	102.96 (10)	C6—C5—H5	119.00
O2—Mo1—O4	100.28 (10)	C5—C6—H6	120.00
O2—Mo1—N1	154.77 (9)	C7—C6—H6	120.00
O2—Mo1—N2	78.68 (9)	C6—C7—H7	119.00
O3—Mo1—O4	104.21 (10)	C8—C7—H7	119.00
O3—Mo1—N1	96.16 (10)	C7—C8—H8	120.00
O3—Mo1—N2	169.12 (9)	C9—C8—H8	120.00
O4—Mo1—N1	90.65 (9)	N1—C11—H11	117.00
O4—Mo1—N2	85.92 (9)	C10—C11—H11	117.00
N1—Mo1—N2	79.52 (9)	N1—C12—H12A	109.00
Mo1—O1—C1	124.64 (18)	N1—C12—H12B	109.00
Mo1—O2—C25	129.78 (16)	C13—C12—H12A	109.00
Mo1—N1—C11	124.36 (19)	C13—C12—H12B	109.00
Mo1—N1—C12	118.61 (18)	H12A—C12—H12B	108.00
C11—N1—C12	116.8 (2)	N2—C14—H14A	109.00
Mo1—N2—C14	118.55 (19)	N2—C14—H14B	109.00
Mo1—N2—C15	123.10 (18)	C13—C14—H14A	109.00
C14—N2—C15	118.0 (2)	C13—C14—H14B	109.00
O1—C1—C2	118.2 (3)	H14A—C14—H14B	108.00
O1—C1—C10	122.9 (2)	N2—C15—H15	117.00
C2—C1—C10	118.9 (3)	C16—C15—H15	117.00
C1—C2—C3	120.7 (3)	C17—C18—H18	119.00
C2—C3—C4	122.3 (3)	C19—C18—H18	119.00
C3—C4—C5	121.5 (3)	C18—C19—H19	120.00
C3—C4—C9	118.7 (3)	C20—C19—H19	120.00
C5—C4—C9	119.8 (3)	C19—C20—H20	120.00
C4—C5—C6	121.3 (3)	C21—C20—H20	120.00
C5—C6—C7	119.3 (3)	C20—C21—H21	120.00
C6—C7—C8	121.4 (4)	C22—C21—H21	120.00
C7—C8—C9	120.5 (3)	C22—C23—H23	119.00
C4—C9—C8	117.8 (3)	C24—C23—H23	119.00
C4—C9—C10	119.2 (3)	C23—C24—H24	120.00
C8—C9—C10	122.9 (3)	C25—C24—H24	120.00
C1—C10—C9	120.0 (3)	C13—C26—H26A	110.00
C1—C10—C11	118.5 (3)	C13—C26—H26B	110.00
C9—C10—C11	120.5 (3)	C13—C26—H26C	109.00
N1—C11—C10	126.5 (3)	H26A—C26—H26B	109.00
N1—C12—C13	112.7 (2)	H26A—C26—H26C	109.00
C12—C13—C14	111.7 (3)	H26B—C26—H26C	109.00
C12—C13—C26	111.1 (3)	C13—C27—H27A	109.00
C12—C13—C27	106.6 (3)	C13—C27—H27B	109.00
C14—C13—C26	110.4 (3)	C13—C27—H27C	109.00
C14—C13—C27	106.8 (2)	H27A—C27—H27B	109.00
C26—C13—C27	110.2 (3)	H27A—C27—H27C	110.00
N2—C14—C13	114.1 (2)	H27B—C27—H27C	109.00
N2—C15—C16	125.4 (3)	Cl1A—C28—Cl2	113.5 (2)
C15—C16—C17	120.5 (3)	Cl1B—C28—Cl2	104.0 (4)
C15—C16—C25	120.0 (3)	Cl1A—C28—H28A	109.00
C17—C16—C25	119.1 (3)	Cl1A—C28—H28B	109.00
C16—C17—C18	123.1 (3)	Cl2—C28—H28A	109.00
C16—C17—C22	119.4 (3)	Cl2—C28—H28B	109.00
C18—C17—C22	117.5 (3)	Cl2—C28—H28C	111.00
C17—C18—C19	121.2 (3)	Cl2—C28—H28D	111.00
C18—C19—C20	120.7 (3)	Cl1B—C28—H28C	115.00
C19—C20—C21	120.2 (3)	Cl1B—C28—H28D	108.00
C20—C21—C22	120.5 (3)	H28A—C28—H28B	108.00
C17—C22—C21	120.0 (3)	H28C—C28—H28D	109.00
C17—C22—C23	119.0 (3)	Cl3—C29—Cl4	115.7 (5)
C21—C22—C23	121.0 (3)	Cl3—C29—H29A	109.00
C22—C23—C24	121.1 (3)	Cl3—C29—H29B	108.00
C23—C24—C25	120.7 (3)	Cl4—C29—H29A	108.00
O2—C25—C16	123.0 (3)	Cl4—C29—H29B	108.00
O2—C25—C24	116.7 (2)	H29A—C29—H29B	107.00
C16—C25—C24	120.3 (3)

O2—Mo1—O1—C1	149.5 (2)	C9—C4—C5—C6	0.4 (5)
O3—Mo1—O1—C1	46.5 (2)	C3—C4—C9—C8	−178.7 (3)
N1—Mo1—O1—C1	−49.8 (2)	C3—C4—C9—C10	−2.4 (4)
N2—Mo1—O1—C1	−131.1 (2)	C5—C4—C9—C8	0.3 (4)
O1—Mo1—O2—C25	33.1 (2)	C5—C4—C9—C10	176.6 (3)
O3—Mo1—O2—C25	121.9 (2)	C4—C5—C6—C7	−0.4 (5)
O4—Mo1—O2—C25	−130.7 (2)	C5—C6—C7—C8	−0.3 (5)
N1—Mo1—O2—C25	−16.4 (4)	C6—C7—C8—C9	0.9 (5)
N2—Mo1—O2—C25	−47.1 (2)	C7—C8—C9—C4	−0.9 (4)
O1—Mo1—N1—C11	37.9 (2)	C7—C8—C9—C10	−177.1 (3)
O1—Mo1—N1—C12	−137.0 (2)	C4—C9—C10—C1	0.2 (4)
O2—Mo1—N1—C11	88.4 (3)	C4—C9—C10—C11	168.5 (3)
O2—Mo1—N1—C12	−86.5 (3)	C8—C9—C10—C1	176.3 (3)
O3—Mo1—N1—C11	−50.9 (2)	C8—C9—C10—C11	−15.4 (4)
O3—Mo1—N1—C12	134.2 (2)	C1—C10—C11—N1	−23.9 (4)
O4—Mo1—N1—C11	−155.3 (2)	C9—C10—C11—N1	167.7 (3)
O4—Mo1—N1—C12	29.9 (2)	N1—C12—C13—C14	−65.6 (3)
N2—Mo1—N1—C11	119.0 (2)	N1—C12—C13—C26	58.2 (3)
N2—Mo1—N1—C12	−55.9 (2)	N1—C12—C13—C27	178.2 (2)
O1—Mo1—N2—C14	131.0 (2)	C12—C13—C14—N2	60.7 (3)
O1—Mo1—N2—C15	−55.5 (2)	C26—C13—C14—N2	−63.5 (3)
O2—Mo1—N2—C14	−142.3 (2)	C27—C13—C14—N2	176.8 (3)
O2—Mo1—N2—C15	31.3 (2)	N2—C15—C16—C17	163.0 (3)
O4—Mo1—N2—C14	−40.9 (2)	N2—C15—C16—C25	−23.8 (4)
O4—Mo1—N2—C15	132.6 (2)	C15—C16—C17—C18	−14.9 (5)
N1—Mo1—N2—C14	50.5 (2)	C15—C16—C17—C22	168.7 (3)
N1—Mo1—N2—C15	−136.0 (2)	C25—C16—C17—C18	171.9 (3)
Mo1—O1—C1—C2	−147.8 (2)	C25—C16—C17—C22	−4.6 (4)
Mo1—O1—C1—C10	34.8 (3)	C15—C16—C25—O2	12.1 (4)
Mo1—O2—C25—C16	35.8 (4)	C15—C16—C25—C24	−165.6 (3)
Mo1—O2—C25—C24	−146.5 (2)	C17—C16—C25—O2	−174.6 (3)
Mo1—N1—C11—C10	−11.9 (4)	C17—C16—C25—C24	7.7 (4)
C12—N1—C11—C10	163.0 (3)	C16—C17—C18—C19	−176.5 (3)
Mo1—N1—C12—C13	75.1 (3)	C22—C17—C18—C19	0.1 (5)
C11—N1—C12—C13	−100.2 (3)	C16—C17—C22—C21	176.7 (3)
Mo1—N2—C14—C13	−61.8 (3)	C16—C17—C22—C23	−1.1 (5)
C15—N2—C14—C13	124.3 (3)	C18—C17—C22—C21	0.1 (5)
Mo1—N2—C15—C16	−5.7 (4)	C18—C17—C22—C23	−177.8 (3)
C14—N2—C15—C16	167.9 (3)	C17—C18—C19—C20	0.3 (6)
O1—C1—C2—C3	178.1 (3)	C18—C19—C20—C21	−0.8 (6)
C10—C1—C2—C3	−4.4 (4)	C19—C20—C21—C22	0.9 (5)
O1—C1—C10—C9	−179.4 (2)	C20—C21—C22—C17	−0.6 (5)
O1—C1—C10—C11	12.0 (4)	C20—C21—C22—C23	177.3 (3)
C2—C1—C10—C9	3.1 (4)	C17—C22—C23—C24	3.9 (5)
C2—C1—C10—C11	−165.4 (2)	C21—C22—C23—C24	−174.0 (3)
C1—C2—C3—C4	2.2 (5)	C22—C23—C24—C25	−0.8 (5)
C2—C3—C4—C5	−177.8 (3)	C23—C24—C25—O2	177.1 (3)
C2—C3—C4—C9	1.2 (5)	C23—C24—C25—C16	−5.1 (5)
C3—C4—C5—C6	179.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3ⁱ	0.95	2.43	3.328 (5)	159
C11—H11···O4ⁱⁱ	0.95	2.38	3.297 (3)	161
C12—H12A···O4	0.99	2.47	2.974 (4)	111
C27—H27A···O3ⁱⁱ	0.98	2.55	3.490 (4)	161
C28—H28A···O2ⁱⁱⁱ	0.99	2.40	3.213 (5)	139
C28—H28A···O4ⁱⁱⁱ	0.99	2.53	3.429 (6)	151

Symmetry codes: (i) −x+1/2, −y+3/2, −z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Mo(C₂₇H₂₄N₂O₂)O₂]·1.75CH₂Cl₂
M_r	685.04
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	27.6049 (18), 10.7743 (8), 21.6474 (14)
β (°)	112.861 (7)
V (Å³)	5932.7 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.38 × 0.23 × 0.18

Data collection
Diffractometer	Stoe IPDS diffractometer
Absorption correction	Multi-scan (MULscanABS in PLATON; Spek, 2009)
T_min, T_max	0.833, 0.864
No. of measured, independent and observed [I > 2σ(I)] reflections	21863, 5537, 4789
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.106, 1.12
No. of reflections	5537
No. of parameters	372
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0575P)² + 13.6226P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.08, −0.83

Computer programs: EXPOSE in IPDS-I (Stoe & Cie, 2000), CELL in IPDS-I (Stoe & Cie, 2000), INTEGRATE in IPDS-I (Stoe & Cie, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006).

Selected bond lengths (Å) top

Mo1—O1	2.0888 (19)	Mo1—O4	1.713 (2)
Mo1—O2	1.957 (2)	Mo1—N1	2.118 (2)
Mo1—O3	1.702 (2)	Mo1—N2	2.297 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3ⁱ	0.95	2.43	3.328 (5)	159
C11—H11···O4ⁱⁱ	0.95	2.38	3.297 (3)	161
C12—H12A···O4	0.99	2.47	2.974 (4)	111
C27—H27A···O3ⁱⁱ	0.98	2.55	3.490 (4)	161
C28—H28A···O2ⁱⁱⁱ	0.99	2.40	3.213 (5)	139
C28—H28A···O4ⁱⁱⁱ	0.99	2.53	3.429 (6)	151

Symmetry codes: (i) −x+1/2, −y+3/2, −z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x, y−1, z.

References

Abbasi, A., Sheikhshoaie, I., Saghaei, A. & Monadi, N. (2008). Acta Cryst. E64, m1036. Web of Science CSD CrossRef IUCr Journals Google Scholar
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
Holm, R. H., Kennepohl, P. & Solomon, E. I. (1996). Chem. Rev. 96, 2239–2314. CrossRef PubMed CAS Web of Science Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Maurya, M. R., Jayaswal, M. N., Puranik, V. G., Chakrabarti, P., Gopinathan, S. & Gopinathan, C. (1997). Polyhedron, 16, 3977–3983. CSD CrossRef CAS Web of Science Google Scholar
Nakayima, K., Yokoyama, K., Kano, T. & Kojima, M. (1998). Inorg. Chim. Acta, 282, 209–216. Google Scholar
Rao, C. P., Sreedhara, A., Rao, P. V., Lokanath, N. K., Sridhar, M. A., Prasad, J. S. & Rissanen, K. (1998). Polyhedron, 18, 289–297. Web of Science CSD CrossRef Google Scholar
Sheikhshoaie, I., Rezaeifard, A., Monadi, N. & Kaafi, S. (2009). Polyhedron, 28, 733–738. Web of Science CSD CrossRef CAS Google Scholar
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Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 65| Part 9| September 2009| Pages m1124-m1125

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

{1,1′-[(2,2-Di­methyl­propane-1,3-di­yl)bis­­(nitrilo­methyl­­idyne)]di-2-naphthol­ato}dioxidomolybdenum(VI) di­chloro­methane 1.75-solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

{1,1′-[(2,2-Dimethylpropane-1,3-diyl)bis(nitrilomethylidyne)]di-2-naphtholato}dioxidomolybdenum(VI) dichloromethane 1.75-solvate