{2,2'-[Ethane-1,2-diylbis(nitrilo-methan-yl-yl-idene)]diphenolato}(iso-propano-lato)aluminium di-chloro-methane hemisolvate.

In the title compound, [Al(C16H14N2O2)(C3H7O)]·0.5CH2Cl2, the salen complex is monomeric and the dichlormethane solvent mol-ecule lies on a crystallographic twofold axis. The central Al atom is fivefold coordinated and possesses a square-based pyramidal environment. The Al-OAlk( (i) prop-yl) bond [1.7404 (14) Å] is much shorter than the Al-OAr(salen) bond lengths [1.7974 (15) and 1.8094 (14) Å]. The iso-propyl-oxo group forms an intra-molecular C-H⋯N hydrogen bond. In the crystal, the complex mol-ecules are linked by weak C-H⋯O inter-actions.

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 = 394.82

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.081

S = 1.04

4069 reflections

242 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.32 e Å−3

Absolute structure: Flack (1983 ▶), 1872 Friedel pairs

Absolute structure parameter: −0.09 (7)

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.

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

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813029644/fk2075Isup3.mol

969040

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

[Al(C16H14N2O2)(C3H7O)]·0.5CH2Cl2	F(000) = 3312
Mr = 394.82	Dx = 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

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

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(Fo2) + (0.0417P)2 + 4.145P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
4069 reflections	Δρmax = 0.32 e Å−3
242 parameters	Δρmin = −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)

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
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*

	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

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

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

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) ; (ii) .