{2,2′-[Ethane-1,2-diylbis(nitrilo­methan­yl­yl­idene)]diphenolato}(iso­propano­lato)aluminium di­chloro­methane hemisolvate

Zaitsev, K.V.; Kuchuk, E.A.; Karlov, S.S.; Zaitseva, G.S.; Churakov, A.V.

doi:10.1107/S1600536813029644

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages m631-m632

doi:10.1107/S1600536813029644

Open

access

{2,2′-[Ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolato}(isopropanolato)aluminium dichloromethane hemisolvate

Kirill V. Zaitsev,^a Ekaterina A. Kuchuk,^a Sergey S. Karlov,^a Galina S. Zaitseva ^a and Andrei V. Churakov ^b ^*

^aDepartment of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russian Federation, and ^bInstitute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii prosp. 31, Moscow 119991, Russian Federation
^*Correspondence e-mail: churakov@igic.ras.ru

(Received 18 October 2013; accepted 28 October 2013; online 6 November 2013)

In the title compound, [Al(C₁₆H₁₄N₂O₂)(C₃H₇O)]·0.5CH₂Cl₂, the salen complex is monomeric and the dichlormethane solvent molecule lies on a crystallographic twofold axis. The central Al atom is fivefold coordinated and possesses a square-based pyramidal environment. The Al—OAlk(ⁱpropyl) bond [1.7404 (14) Å] is much shorter than the Al—OAr(salen) bond lengths [1.7974 (15) and 1.8094 (14) Å]. The isopropyloxo group forms an intramolecular C—H⋯N hydrogen bond. In the crystal, the complex molecules are linked by weak C—H⋯O interactions.

CCDC reference: 969040

Related literature

For general background to the chemistry affording aluminium complexes based on salen-type ligands, see: Matsumoto et al. (2007 ); Gurian et al. (1991 ); Atwood et al. (1997 ); Muñoz-Hernandez et al. (2000 ). For our previous work on main group element complexes with polydentate N,O-ligands, see: Karlov & Zaitseva (2001 ). For structures of related monomeric Al-salen complexes, see: Darensburg & Billodeaux (2005 ); Gurian et al. (1991); Pang et al. (2008 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

[Al(C₁₆H₁₄N₂O₂)(C₃H₇O)]·0.5CH₂Cl₂
M_r = 394.82
Orthorhombic, F d d 2
a = 24.427 (3) Å
b = 30.875 (4) Å
c = 10.0956 (13) Å
V = 7614.0 (16) Å³
Z = 16
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 173 K
0.25 × 0.15 × 0.04 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.936, T_max = 0.989
13794 measured reflections
4069 independent reflections
3687 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.081
S = 1.04
4069 reflections
242 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983 ), 1872 Friedel pairs
Absolute structure parameter: −0.09 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯N1	1.00	2.64	3.204 (3)	116
C18—H18A⋯O3ⁱ	0.99	2.55	3.508 (2)	163
C4—H4⋯O1ⁱⁱ	0.96	2.33	3.2539 (18)	160
Symmetry codes: (i) $[x+{\script{1\over 4}}, -y+{\script{3\over 4}}, z-{\script{1\over 4}}]$ ; (ii) $[-x+{\script{7\over 4}}, y+{\script{1\over 4}}, z-{\script{1\over 4}}]$ .

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

Supporting information

CCDC reference: 969040

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813029644/fk2075sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813029644/fk2075Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813029644/fk2075Isup3.mol

checkCIF report

Comment top

As a part of our investigation on chemistry of main group elements complexes based on tetradentate ligands (Karlov & Zaitseva, 2001) we obtained and studied the structure of the salen title compound [(salen)AlO-ⁱPr]. The aluminium complex is monomeric (Fig. 1) with a fivefold coordinated Al centre. Its coordination geometry is close to square-based pyramidal with the salen ligand occupying the basal plane and the isopropyloxo group in axial position. It was shown, that the closely related methyloxo compound with an unsubstituted salen ligand [(MeO)(salen)Al]₂ is dimeric with two bridging µ₂-alkyloxo ligands (Gurian et al. (1991)). In contrast, a similar compound with bulky trimethylphenoxo substituent (2,4,6-Me₃C₆H₂O)(salen)Al exhibited monomeric nature (Atwood et al. (1997)). Also all Al compounds with substituted salen ligands, like widely studied complexes of bulky (^tBu)₄salen, are monomeric according to CSD data (Allen, 2002), surely due to the steric hindrances. Thus, it may be assumed that the nuclearity of aluminium complexes with an unsubstituted salen ligand depends on the size of the additional alkyloxo group.

The central metal atom is displaced from the basal N,N,O,O plane by 0.4874 (9) Å. Unexpectedly, the Al-O(3)Alk distance (1.7404 (14) Å) is much shorter than Al-OAr bond lengths from the salen ligand (1.7974 (15) and 1.8094 (14) Å). On the other hand, the Al—O(3)—C(1) angle is quite large with 130.54 (12) °. These values indicate the noticeable degree of π- donation from the apical alkyloxo ligand towards the aluminium centre. The same features were previously found in the structure of the closely related monomeric ethyloxo complex (EtO)(salen(^tBu)₄)Al (Muñoz-Hernandez et al. (2000)).

The isopropyloxo group forms an intramolecular hydrogen bond C1—H1A···N1 with H···N with 2.64 Å and C—H···N 116.0 (1)° that is connected with the mutual ecliptic arrangement of N1—Al1 and O3—C1 bonds.

In the crystal packing, the Al-complexes are linked by weak C18—H18A···O3 hydrogen bonds (C···O 3.508 (2) Å, C—H···O 162.9 (1)°). The asymmetric unit contains a solvent dichlormethane molecule that lies on a crystallographic 2-fold axis and forms C4—H4···O1 hydrogen bonds with C···O separations of 3.2539 (18) Å.

Related literature top

For general background to the chemistry affording aluminium complexes based on salen-type ligands, see: Matsumoto et al. (2007); Gurian et al. (1991); Atwood et al. (1997); Muñoz-Hernandez et al. (2000). For our previous work on main group element complexes with polydentate N,O-ligands, see: Karlov & Zaitseva (2001). For structures of related monomeric Al-salen complexes, see: Darensburg & Billodeaux (2005); Gurian et al. (1991); Pang et al. (2008). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

The title compound was obtained from reaction of equimolar amounts of Al(O-iPr)₃ and salen in toluene at reflux as a solid.

¹H NMR (CDCl₃): δ 8.24 (s, 2H, N=CH), 7.40–7.33 (m, 2H, aromatic H atoms), 7.16–7.07 (m, 4H, aromatic H atoms), 6.73–6.67 (m, 2H, aromatic H atoms), 4.12–4.02 (m, 2H, NCH₂), 3.75 (sept, J = 6.1 Hz, 1H, OCH), 3.65–3.58 (m, 2H, NCH₂), 0.91 d (d, J = 6.1 Hz, 6H, OCHMe₂) p.p.m..

¹³C NMR (CDCl₃): δ 168.97 (N=CH), 165.78, 135.46, 132.99, 122.26, 118.74, 116.55 (aromatic carbons), 62.80 (OCH), 54.44 (NCH₂), 27.33 (OCHMe₂) p.p.m..

Computing details top

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

Figures top

Fig. 1. The molecular structure of the title compound. Anisotropic displacement ellipsoids are shown at the 50% probability level. [Symmetry code: (A) 2-x, 1-y, z]

{2,2'-[Ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolato}(isopropanolato)aluminium dichloromethane hemisolvate top

Crystal data top

[Al(C₁₆H₁₄N₂O₂)(C₃H₇O)]·0.5CH₂Cl₂	F(000) = 3312
M_r = 394.82	D_x = 1.378 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 4106 reflections
a = 24.427 (3) Å	θ = 2.3–25.6°
b = 30.875 (4) Å	µ = 0.27 mm⁻¹
c = 10.0956 (13) Å	T = 173 K
V = 7614.0 (16) Å³	Plate, colourless
Z = 16	0.25 × 0.15 × 0.04 mm

Data collection top

Bruker SMART APEXII diffractometer	4069 independent reflections
Radiation source: fine-focus sealed tube	3687 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 27.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −31→31
T_min = 0.936, T_max = 0.989	k = −39→39
13794 measured reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.081	w = 1/[σ²(F_o²) + (0.0417P)² + 4.145P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
4069 reflections	Δρ_max = 0.32 e Å⁻³
242 parameters	Δρ_min = −0.32 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1872 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.09 (7)

Crystal data top

[Al(C₁₆H₁₄N₂O₂)(C₃H₇O)]·0.5CH₂Cl₂	V = 7614.0 (16) Å³
M_r = 394.82	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 24.427 (3) Å	µ = 0.27 mm⁻¹
b = 30.875 (4) Å	T = 173 K
c = 10.0956 (13) Å	0.25 × 0.15 × 0.04 mm

Data collection top

Bruker SMART APEXII diffractometer	4069 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3687 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.989	R_int = 0.032
13794 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.081	Δρ_max = 0.32 e Å⁻³
S = 1.04	Δρ_min = −0.32 e Å⁻³
4069 reflections	Absolute structure: Flack (1983), 1872 Friedel pairs
242 parameters	Absolute structure parameter: −0.09 (7)
1 restraint

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
Al1	0.80543 (2)	0.339391 (17)	0.48762 (6)	0.02073 (13)
O1	0.83307 (5)	0.32093 (4)	0.64267 (15)	0.0274 (3)
O2	0.74619 (5)	0.30520 (4)	0.51299 (14)	0.0244 (3)
O3	0.77795 (5)	0.39121 (4)	0.50117 (16)	0.0280 (3)
N1	0.88207 (6)	0.35385 (5)	0.42972 (17)	0.0233 (4)
N2	0.80155 (6)	0.32532 (5)	0.29380 (17)	0.0237 (4)
C1	0.80382 (8)	0.43157 (6)	0.5214 (2)	0.0265 (4)
H1A	0.8401	0.4311	0.4756	0.032*
C2	0.76904 (10)	0.46682 (7)	0.4601 (3)	0.0408 (6)
H2A	0.7647	0.4612	0.3651	0.061*
H2B	0.7869	0.4949	0.4730	0.061*
H2C	0.7330	0.4671	0.5025	0.061*
C3	0.81316 (11)	0.44040 (8)	0.6673 (3)	0.0438 (6)
H3A	0.8334	0.4162	0.7066	0.066*
H3B	0.7778	0.4435	0.7120	0.066*
H3C	0.8343	0.4672	0.6774	0.066*
C11	0.88005 (8)	0.32767 (6)	0.7048 (2)	0.0247 (4)
C12	0.88427 (9)	0.31743 (7)	0.8386 (2)	0.0332 (5)
H12	0.8533	0.3063	0.8842	0.040*
C13	0.93293 (9)	0.32316 (7)	0.9064 (3)	0.0366 (5)
H13	0.9349	0.3161	0.9978	0.044*
C14	0.97909 (9)	0.33922 (7)	0.8422 (3)	0.0350 (5)
H14	1.0125	0.3426	0.8890	0.042*
C15	0.97586 (9)	0.35001 (7)	0.7114 (3)	0.0328 (5)
H15	1.0073	0.3612	0.6678	0.039*
C16	0.92665 (8)	0.34479 (6)	0.6396 (2)	0.0261 (4)
C17	0.92542 (8)	0.35630 (6)	0.5013 (2)	0.0270 (4)
H17	0.9583	0.3662	0.4610	0.032*
C18	0.88543 (8)	0.36551 (7)	0.2887 (2)	0.0275 (5)
H18A	0.9239	0.3644	0.2578	0.033*
H18B	0.8711	0.3951	0.2742	0.033*
C21	0.70533 (7)	0.29526 (6)	0.4337 (2)	0.0212 (4)
C22	0.65738 (8)	0.27644 (6)	0.4864 (2)	0.0260 (4)
H22	0.6560	0.2686	0.5773	0.031*
C23	0.61261 (8)	0.26946 (6)	0.4067 (2)	0.0304 (5)
H23	0.5805	0.2571	0.4442	0.036*
C24	0.61294 (9)	0.27991 (7)	0.2725 (2)	0.0356 (5)
H24	0.5809	0.2767	0.2200	0.043*
C25	0.66070 (9)	0.29500 (7)	0.2186 (2)	0.0346 (5)
H25	0.6622	0.3008	0.1262	0.041*
C26	0.70752 (8)	0.30217 (6)	0.2965 (2)	0.0270 (4)
C27	0.75757 (8)	0.31427 (6)	0.2327 (2)	0.0269 (4)
H27	0.7583	0.3141	0.1387	0.032*
C28	0.85114 (8)	0.33286 (7)	0.2152 (2)	0.0293 (4)
H28A	0.8413	0.3441	0.1264	0.035*
H28B	0.8717	0.3055	0.2038	0.035*
Cl1	0.96134 (3)	0.46418 (3)	0.61765 (8)	0.0636 (2)
C4	1.0000	0.5000	0.5209 (3)	0.0304 (7)
H4	0.9758	0.5163	0.4650	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Al1	0.0173 (2)	0.0212 (3)	0.0238 (3)	−0.0013 (2)	0.0013 (2)	0.0001 (2)
O1	0.0219 (7)	0.0353 (8)	0.0249 (8)	−0.0063 (6)	−0.0031 (6)	0.0037 (6)
O2	0.0216 (6)	0.0264 (6)	0.0252 (8)	−0.0046 (5)	−0.0003 (6)	0.0029 (6)
O3	0.0210 (6)	0.0211 (6)	0.0418 (9)	−0.0013 (5)	0.0022 (7)	−0.0033 (7)
N1	0.0209 (8)	0.0223 (8)	0.0266 (9)	−0.0007 (6)	0.0031 (7)	0.0016 (7)
N2	0.0232 (8)	0.0241 (8)	0.0238 (9)	−0.0005 (6)	0.0037 (7)	0.0019 (7)
C1	0.0222 (9)	0.0229 (9)	0.0344 (12)	−0.0023 (7)	0.0027 (9)	−0.0023 (8)
C2	0.0459 (13)	0.0263 (10)	0.0502 (17)	0.0013 (9)	−0.0088 (12)	−0.0008 (10)
C3	0.0522 (15)	0.0374 (12)	0.0416 (15)	−0.0125 (11)	−0.0065 (12)	−0.0009 (11)
C11	0.0232 (9)	0.0233 (9)	0.0276 (12)	0.0007 (8)	−0.0031 (8)	−0.0012 (8)
C12	0.0300 (11)	0.0373 (12)	0.0321 (13)	−0.0002 (9)	−0.0016 (9)	0.0001 (10)
C13	0.0365 (12)	0.0431 (13)	0.0301 (13)	0.0050 (10)	−0.0075 (10)	−0.0040 (10)
C14	0.0272 (11)	0.0368 (12)	0.0409 (14)	0.0030 (9)	−0.0107 (10)	−0.0084 (10)
C15	0.0227 (9)	0.0293 (10)	0.0464 (15)	−0.0009 (8)	−0.0030 (9)	−0.0045 (10)
C16	0.0225 (9)	0.0226 (9)	0.0332 (12)	0.0004 (7)	−0.0024 (9)	−0.0028 (8)
C17	0.0200 (9)	0.0221 (9)	0.0390 (13)	−0.0003 (7)	0.0039 (9)	0.0003 (9)
C18	0.0214 (10)	0.0280 (10)	0.0330 (12)	−0.0003 (8)	0.0063 (9)	0.0068 (9)
C21	0.0205 (9)	0.0157 (8)	0.0275 (10)	0.0022 (7)	−0.0015 (8)	−0.0005 (7)
C22	0.0271 (10)	0.0207 (9)	0.0302 (11)	−0.0002 (7)	0.0022 (10)	−0.0006 (9)
C23	0.0222 (10)	0.0257 (10)	0.0433 (14)	−0.0029 (8)	0.0033 (10)	−0.0030 (9)
C24	0.0243 (10)	0.0413 (12)	0.0411 (14)	−0.0034 (9)	−0.0088 (10)	−0.0027 (10)
C25	0.0309 (11)	0.0429 (12)	0.0299 (12)	−0.0047 (9)	−0.0059 (10)	0.0020 (10)
C26	0.0268 (10)	0.0268 (10)	0.0273 (12)	−0.0015 (8)	−0.0016 (9)	−0.0002 (8)
C27	0.0280 (10)	0.0300 (10)	0.0228 (11)	−0.0008 (8)	0.0009 (9)	0.0001 (9)
C28	0.0272 (10)	0.0327 (10)	0.0280 (12)	0.0020 (8)	0.0064 (9)	0.0044 (9)
Cl1	0.0662 (4)	0.0686 (4)	0.0559 (5)	−0.0116 (4)	0.0136 (4)	0.0262 (4)
C4	0.0347 (16)	0.0328 (15)	0.0236 (16)	−0.0003 (12)	0.000	0.000

Geometric parameters (Å, º) top

Al1—O3	1.7404 (14)	C14—C15	1.363 (4)
Al1—O1	1.7974 (15)	C14—H14	0.9500
Al1—O2	1.8094 (14)	C15—C16	1.413 (3)
Al1—N2	2.0066 (18)	C15—H15	0.9500
Al1—N1	2.0115 (17)	C16—C17	1.442 (3)
O1—C11	1.324 (2)	C17—H17	0.9500
O2—C21	1.315 (2)	C18—C28	1.506 (3)
O3—C1	1.412 (2)	C18—H18A	0.9900
N1—C17	1.284 (3)	C18—H18B	0.9900
N1—C18	1.471 (3)	C21—C26	1.403 (3)
N2—C27	1.285 (3)	C21—C22	1.412 (3)
N2—C28	1.467 (2)	C22—C23	1.375 (3)
C1—C2	1.513 (3)	C22—H22	0.9500
C1—C3	1.515 (3)	C23—C24	1.392 (3)
C1—H1A	1.0000	C23—H23	0.9500
C2—H2A	0.9800	C24—C25	1.369 (3)
C2—H2B	0.9800	C24—H24	0.9500
C2—H2C	0.9800	C25—C26	1.406 (3)
C3—H3A	0.9800	C25—H25	0.9500
C3—H3B	0.9800	C26—C27	1.431 (3)
C3—H3C	0.9800	C27—H27	0.9500
C11—C12	1.392 (3)	C28—H28A	0.9900
C11—C16	1.417 (3)	C28—H28B	0.9900
C12—C13	1.383 (3)	Cl1—C4	1.7521 (19)
C12—H12	0.9500	C4—Cl1ⁱ	1.7520 (19)
C13—C14	1.392 (3)	C4—H4	0.9600
C13—H13	0.9500

O3—Al1—O1	111.59 (8)	C15—C14—H14	120.3
O3—Al1—O2	102.52 (7)	C13—C14—H14	120.3
O1—Al1—O2	89.55 (7)	C14—C15—C16	121.2 (2)
O3—Al1—N2	104.92 (8)	C14—C15—H15	119.4
O1—Al1—N2	142.97 (7)	C16—C15—H15	119.4
O2—Al1—N2	88.51 (7)	C15—C16—C11	119.2 (2)
O3—Al1—N1	100.24 (7)	C15—C16—C17	119.13 (19)
O1—Al1—N1	88.50 (7)	C11—C16—C17	121.66 (18)
O2—Al1—N1	156.20 (7)	N1—C17—C16	123.21 (18)
N2—Al1—N1	78.96 (7)	N1—C17—H17	118.4
C11—O1—Al1	133.47 (13)	C16—C17—H17	118.4
C21—O2—Al1	131.06 (13)	N1—C18—C28	106.40 (16)
C1—O3—Al1	130.54 (12)	N1—C18—H18A	110.4
C17—N1—C18	118.95 (17)	C28—C18—H18A	110.4
C17—N1—Al1	128.11 (15)	N1—C18—H18B	110.4
C18—N1—Al1	112.80 (13)	C28—C18—H18B	110.4
C27—N2—C28	118.22 (18)	H18A—C18—H18B	108.6
C27—N2—Al1	124.39 (15)	O2—C21—C26	122.43 (17)
C28—N2—Al1	117.03 (13)	O2—C21—C22	119.78 (18)
O3—C1—C2	108.93 (17)	C26—C21—C22	117.78 (18)
O3—C1—C3	111.52 (18)	C23—C22—C21	120.3 (2)
C2—C1—C3	110.63 (19)	C23—C22—H22	119.9
O3—C1—H1A	108.6	C21—C22—H22	119.9
C2—C1—H1A	108.6	C22—C23—C24	121.9 (2)
C3—C1—H1A	108.6	C22—C23—H23	119.0
C1—C2—H2A	109.5	C24—C23—H23	119.0
C1—C2—H2B	109.5	C25—C24—C23	118.1 (2)
H2A—C2—H2B	109.5	C25—C24—H24	121.0
C1—C2—H2C	109.5	C23—C24—H24	121.0
H2A—C2—H2C	109.5	C24—C25—C26	121.6 (2)
H2B—C2—H2C	109.5	C24—C25—H25	119.2
C1—C3—H3A	109.5	C26—C25—H25	119.2
C1—C3—H3B	109.5	C21—C26—C25	119.85 (19)
H3A—C3—H3B	109.5	C21—C26—C27	121.08 (19)
C1—C3—H3C	109.5	C25—C26—C27	119.0 (2)
H3A—C3—H3C	109.5	N2—C27—C26	124.6 (2)
H3B—C3—H3C	109.5	N2—C27—H27	117.7
O1—C11—C12	119.22 (19)	C26—C27—H27	117.7
O1—C11—C16	122.36 (19)	N2—C28—C18	107.38 (17)
C12—C11—C16	118.41 (19)	N2—C28—H28A	110.2
C13—C12—C11	121.0 (2)	C18—C28—H28A	110.2
C13—C12—H12	119.5	N2—C28—H28B	110.2
C11—C12—H12	119.5	C18—C28—H28B	110.2
C12—C13—C14	120.8 (2)	H28A—C28—H28B	108.5
C12—C13—H13	119.6	Cl1ⁱ—C4—Cl1	112.20 (18)
C14—C13—H13	119.6	Cl1ⁱ—C4—H4	109.3
C15—C14—C13	119.4 (2)	Cl1—C4—H4	109.0

Symmetry code: (i) −x+2, −y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···N1	1.00	2.64	3.204 (3)	116
C18—H18A···O3ⁱⁱ	0.99	2.55	3.508 (2)	163
C4—H4···O1ⁱⁱⁱ	0.96	2.33	3.2539 (18)	160

Symmetry codes: (ii) x+1/4, −y+3/4, z−1/4; (iii) −x+7/4, y+1/4, z−1/4.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···N1	1.00	2.64	3.204 (3)	115.9
C18—H18A···O3ⁱ	0.99	2.55	3.508 (2)	163.0
C4—H4···O1ⁱⁱ	0.96	2.33	3.2539 (18)	160.4

Symmetry codes: (i) x+1/4, −y+3/4, z−1/4; (ii) −x+7/4, y+1/4, z−1/4.

Acknowledgements

This work was partially supported by the RFBR (12–03–00206_a) and a grant from the President of the Russian Federation to support the research of young Russian scientists and doctors (MD-3634.2012.3).

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Atwood, D. A., Jegier, J. A. & Rutherford, D. (1997). Bull. Chem. Soc. Jpn, 70, 2093–2100. CrossRef CAS Web of Science Google Scholar
Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Darensburg, D. J. & Billodeaux, D. R. (2005). Inorg. Chem. 44, 1433–1442. Web of Science PubMed Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gurian, P. L., Cheatham, L. K., Zillerb, J. W. & Barron, A. R. (1991). J. Chem. Soc. Dalton Trans. pp. 1449–1456. CSD CrossRef Web of Science Google Scholar
Karlov, S. S. & Zaitseva, G. S. (2001). Chem. Heterocycl. Compd, 37, 1325–1357. CrossRef CAS Google Scholar
Matsumoto, K., Saito, B. & Katsuki, T. (2007). Chem. Commun. pp. 3619–3627. Web of Science CrossRef Google Scholar
Muñoz-Hernandez, M.-A., Keizer, T. S., Parkin, S., Zhang, Y. & Atwood, D. A. (2000). J. Chem. Crystallogr. 30, 219–222. Google Scholar
Pang, X., Du, H., Chen, X., Wand, X. & Jing, X. (2008). Chem. Eur. J. 14, 3126–3136. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages m631-m632

doi:10.1107/S1600536813029644

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

{2,2′-[Ethane-1,2-diylbis(nitrilo­methan­yl­yl­­idene)]diphenolato}(iso­propano­lato)aluminium di­chloro­methane hemisolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{2,2′-[Ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolato}(isopropanolato)aluminium dichloromethane hemisolvate