Crystal structure of tris­(N-methyl­salicylaldiminato-κ2N,O)vanadium(III)

Hilbert, J.; Kabus, S.; Näther, C.; Bensch, W.

doi:10.1107/S2056989015021453

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 12| December 2015| Page m225

https://doi.org/10.1107/S2056989015021453

Open

access

Crystal structure of tris(N-methylsalicylaldiminato-κ²N,O)vanadium(III)

Jessica Hilbert,^a ^* Sven Kabus,^a Christian Näther ^a and Wolfgang Bensch ^a

^aInstitut für Anorganische Chemie, Christian-Albrechts-Universität zu Kiel, Max-Eyth-Strasse 2, 24118 Kiel, Germany
^*Correspondence e-mail: jhilbert@ac.uni-kiel.de

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 11 November 2015; accepted 12 November 2015; online 18 November 2015)

The structure of the title complex, [V(C₈H₈NO)₃], comprises neutral and discrete complexes, in which the V^III cation is coordinated by three anionic N-methylalicylaldiminate ligands within a slightly distorted mer-N₃O₃ octahedral geometry. In the crystal structure, the molecules are linked via C—H⋯O hydrogen bonds into supramolecular chains that extend along the c axis.

Keywords: crystal structure; vanadium(III); N-methylsalicylaldiminate.

CCDC reference: 1436532

1. Related literature

For structures of discrete complexes of Mo and V with N-methylsaldicylaldiminate as the ligand, see: Davies & Gatehouse (1974 ); Cornman et al. (1997 ). For the synthesis of the starting material, see: Bonadies & Carrano (1986 ).

2. Experimental

2.1. Crystal data

[V(C₈H₈NO)₃]
M_r = 453.40
Monoclinic, P 2₁ /c
a = 7.7414 (3) Å
b = 26.0018 (7) Å
c = 11.1004 (4) Å
β = 103.265 (3)°
V = 2174.79 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 170 K
0.24 × 0.14 × 0.06 mm

2.2. Data collection

STOE IPDS-1 diffractometer
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe, 2008 ) T_min = 0.919, T_max = 0.974
18648 measured reflections
4741 independent reflections
4054 reflections with I > 2σ(I)
R_int = 0.030

2.3. Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.102
S = 1.07
4741 reflections
283 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C27—H27⋯O21ⁱ	0.95	2.56	3.431 (2)	153
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe, 2008); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1436532

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989015021453/tk5408sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015021453/tk5408Isup2.hkl

checkCIF report

Synthesis and crystallization top

Most of the chemicals are commercially available: Sn (Fluka, 99.9%), S (Alfa Aesar, 99.5%), and methylamine (abcr, 40% aqueous solution). (N,N'-Disalicylideneethylenediamine)oxovanadium(IV) was prepared following the procedure of Bonadies & Carrano (1986): (N,N'-disalicylideneethylenediamine)oxovanadium (IV) (83.8 mg, 0.25 mmol ), Sn (29.7 mg, 0.25 mmol) and S (24.1 mg, 0.75 mmol) were reacted in a glass tube (inner volume 11 mL) with methylamine (1.5 mL) and H₂O (0.5 mL) under solvothermal conditions at 120 °C for 24 h. Afterwards, the solid residue was filtered off, washed with water and ethanol, and dried over silica gel. The product contains red blocks of the title complex and a small amount of brown blocks of bis(N-methylsaldicylaliminato)oxovanadium(IV) (Cornman et al. (1997)). Even if Sn and S are not contained in the final product, they are needed for product formation, as otherwise only (N,N'-disalicylideneethylenediamine)oxovanadium(IV) is isolated.

Refinement top

The C—H H atoms were positioned with idealized geometry (methyl H atoms allowed to rotate but not to tip) and were refined isotropically with U_eq(H) = 1.2 U_eq(C) (1.5 for methyl H atoms) using a riding model with C—H = 0.95 Å for aromatic H atoms and 0.98 Å for methyl H atoms.

Related literature top

For structures of discrete complexes of Mo and V with N-methylsaldicylaldiminate as the ligand, see: Davies & Gatehouse (1974); Cornman et al. (1997). For the synthesis of the starting material, see: Bonadies & Carrano (1986).

Structure description top

For structures of discrete complexes of Mo and V with N-methylsaldicylaldiminate as the ligand, see: Davies & Gatehouse (1974); Cornman et al. (1997). For the synthesis of the starting material, see: Bonadies & Carrano (1986).

Synthesis and crystallization top

Refinement details top

Computing details top

Data collection: X-AREA (Stoe, 2008); cell refinement: X-AREA (Stoe, 2008); data reduction: X-AREA (Stoe, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title complex with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Unit cell contents of the crystal structure of the title complex viewed in projection down the a axis with hydrogen bonds shown as dashed lines. For clarity, all H atoms except those that participates in hydrogen bonding are omitted.

Tris(N-methylsalicylaldiminato-κ²N,O)vanadium(III) top

Crystal data top

[V(C₈H₈NO)₃]	F(000) = 944
M_r = 453.40	D_x = 1.385 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.7414 (3) Å	Cell parameters from 18648 reflections
b = 26.0018 (7) Å	θ = 1.6–27.0°
c = 11.1004 (4) Å	µ = 0.49 mm⁻¹
β = 103.265 (3)°	T = 170 K
V = 2174.79 (13) Å³	Block, red
Z = 4	0.24 × 0.14 × 0.06 mm

Data collection top

STOE IPDS-1 diffractometer	4054 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
φ–scans	θ_max = 27.0°, θ_min = 1.6°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe, 2008)	h = −9→9
T_min = 0.919, T_max = 0.974	k = −30→33
18648 measured reflections	l = −14→14
4741 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0523P)² + 0.6659P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
4741 reflections	Δρ_max = 0.30 e Å⁻³
283 parameters	Δρ_min = −0.42 e Å⁻³

Crystal data top

[V(C₈H₈NO)₃]	V = 2174.79 (13) Å³
M_r = 453.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7414 (3) Å	µ = 0.49 mm⁻¹
b = 26.0018 (7) Å	T = 170 K
c = 11.1004 (4) Å	0.24 × 0.14 × 0.06 mm
β = 103.265 (3)°

Data collection top

STOE IPDS-1 diffractometer	4741 independent reflections
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe, 2008)	4054 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.974	R_int = 0.030
18648 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.07	Δρ_max = 0.30 e Å⁻³
4741 reflections	Δρ_min = −0.42 e Å⁻³
283 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
V1	0.60947 (4)	0.34777 (2)	0.43424 (3)	0.03210 (10)
O1	0.58715 (17)	0.39024 (5)	0.28969 (12)	0.0400 (3)
C1	0.6728 (2)	0.39169 (7)	0.19994 (17)	0.0375 (4)
C2	0.8151 (3)	0.35824 (8)	0.19485 (18)	0.0390 (4)
C3	0.8995 (3)	0.36297 (9)	0.0951 (2)	0.0497 (5)
H3	0.9964	0.3410	0.0919	0.060*
C4	0.8448 (3)	0.39846 (10)	0.0029 (2)	0.0578 (6)
H4	0.9030	0.4010	−0.0634	0.069*
C5	0.7033 (3)	0.43068 (10)	0.0075 (2)	0.0550 (6)
H5	0.6646	0.4552	−0.0564	0.066*
C6	0.6186 (3)	0.42752 (9)	0.10360 (19)	0.0466 (5)
H6	0.5221	0.4499	0.1049	0.056*
C7	0.8789 (2)	0.31882 (8)	0.28513 (17)	0.0384 (4)
H7	0.9766	0.2989	0.2733	0.046*
N1	0.81716 (19)	0.30777 (6)	0.38049 (14)	0.0351 (3)
C8	0.9074 (3)	0.26689 (8)	0.46168 (18)	0.0423 (4)
H8A	0.9545	0.2808	0.5448	0.064*
H8B	1.0053	0.2533	0.4287	0.064*
H8C	0.8231	0.2392	0.4659	0.064*
O11	0.78967 (17)	0.38679 (5)	0.54398 (12)	0.0397 (3)
C11	0.7839 (3)	0.42940 (8)	0.60833 (18)	0.0402 (4)
C12	0.6228 (3)	0.45333 (8)	0.61828 (18)	0.0416 (4)
C13	0.6290 (3)	0.49804 (9)	0.6899 (2)	0.0510 (5)
H13	0.5211	0.5143	0.6952	0.061*
C14	0.7869 (4)	0.51892 (9)	0.7524 (2)	0.0580 (6)
H14	0.7882	0.5490	0.8012	0.070*
C15	0.9450 (4)	0.49555 (10)	0.7434 (2)	0.0587 (6)
H15	1.0549	0.5099	0.7863	0.070*
C16	0.9439 (3)	0.45159 (9)	0.6727 (2)	0.0501 (5)
H16	1.0533	0.4362	0.6676	0.060*
C17	0.4494 (3)	0.43340 (8)	0.56016 (18)	0.0430 (4)
H17	0.3499	0.4519	0.5740	0.052*
N11	0.4164 (2)	0.39324 (6)	0.49186 (15)	0.0378 (3)
C18	0.2295 (2)	0.37888 (9)	0.4467 (2)	0.0494 (5)
H18A	0.2020	0.3762	0.3562	0.074*
H18B	0.1538	0.4051	0.4715	0.074*
H18C	0.2079	0.3456	0.4822	0.074*
O21	0.42824 (16)	0.30065 (5)	0.34205 (11)	0.0370 (3)
C21	0.3734 (2)	0.25415 (7)	0.35945 (16)	0.0328 (4)
C22	0.4208 (2)	0.22876 (7)	0.47477 (17)	0.0352 (4)
C23	0.3555 (3)	0.17928 (8)	0.4881 (2)	0.0446 (5)
H23	0.3849	0.1630	0.5668	0.054*
C24	0.2496 (3)	0.15367 (9)	0.3894 (2)	0.0499 (5)
H24	0.2098	0.1197	0.3990	0.060*
C25	0.2023 (3)	0.17858 (8)	0.2756 (2)	0.0439 (5)
H25	0.1293	0.1613	0.2070	0.053*
C26	0.2596 (2)	0.22787 (8)	0.26080 (18)	0.0376 (4)
H26	0.2219	0.2445	0.1830	0.045*
C27	0.5263 (2)	0.25346 (7)	0.58385 (16)	0.0349 (4)
H27	0.5412	0.2352	0.6597	0.042*
N21	0.60191 (18)	0.29761 (6)	0.58834 (13)	0.0342 (3)
C28	0.6848 (3)	0.31610 (9)	0.71350 (17)	0.0426 (4)
H28A	0.6331	0.3493	0.7276	0.064*
H28B	0.8128	0.3201	0.7215	0.064*
H28C	0.6637	0.2912	0.7748	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.03170 (16)	0.03642 (17)	0.02820 (16)	−0.00124 (12)	0.00694 (11)	−0.00003 (12)
O1	0.0416 (7)	0.0421 (7)	0.0386 (7)	0.0028 (6)	0.0140 (5)	0.0045 (6)
C1	0.0413 (9)	0.0401 (10)	0.0313 (9)	−0.0078 (8)	0.0092 (7)	−0.0013 (8)
C2	0.0401 (9)	0.0438 (11)	0.0339 (9)	−0.0078 (8)	0.0101 (7)	−0.0057 (8)
C3	0.0530 (12)	0.0571 (13)	0.0436 (11)	−0.0077 (10)	0.0207 (9)	−0.0064 (10)
C4	0.0709 (15)	0.0681 (15)	0.0409 (12)	−0.0128 (12)	0.0264 (11)	−0.0010 (11)
C5	0.0711 (14)	0.0583 (14)	0.0364 (11)	−0.0081 (11)	0.0141 (10)	0.0083 (10)
C6	0.0543 (11)	0.0454 (11)	0.0398 (10)	−0.0047 (9)	0.0105 (9)	0.0034 (9)
C7	0.0324 (8)	0.0467 (11)	0.0369 (10)	−0.0013 (8)	0.0098 (7)	−0.0075 (8)
N1	0.0322 (7)	0.0392 (8)	0.0325 (8)	−0.0001 (6)	0.0045 (6)	−0.0042 (7)
C8	0.0383 (9)	0.0494 (11)	0.0373 (10)	0.0086 (8)	0.0044 (8)	0.0007 (9)
O11	0.0380 (7)	0.0424 (7)	0.0389 (7)	−0.0036 (5)	0.0095 (5)	−0.0066 (6)
C11	0.0474 (10)	0.0388 (10)	0.0341 (9)	−0.0077 (8)	0.0084 (8)	−0.0013 (8)
C12	0.0548 (11)	0.0368 (10)	0.0343 (9)	0.0009 (8)	0.0121 (8)	0.0004 (8)
C13	0.0704 (14)	0.0423 (11)	0.0411 (11)	0.0029 (10)	0.0145 (10)	−0.0016 (9)
C14	0.0837 (17)	0.0436 (12)	0.0470 (12)	−0.0106 (11)	0.0156 (11)	−0.0081 (10)
C15	0.0691 (15)	0.0558 (14)	0.0484 (12)	−0.0224 (12)	0.0075 (11)	−0.0072 (11)
C16	0.0520 (11)	0.0516 (12)	0.0459 (11)	−0.0129 (10)	0.0095 (9)	−0.0056 (10)
C17	0.0460 (10)	0.0461 (11)	0.0393 (10)	0.0074 (8)	0.0148 (8)	0.0021 (9)
N11	0.0366 (8)	0.0424 (9)	0.0356 (8)	0.0021 (6)	0.0105 (6)	0.0010 (7)
C18	0.0337 (9)	0.0605 (13)	0.0550 (13)	0.0018 (9)	0.0120 (9)	−0.0024 (11)
O21	0.0391 (6)	0.0404 (7)	0.0296 (6)	−0.0041 (5)	0.0041 (5)	0.0024 (5)
C21	0.0287 (8)	0.0365 (9)	0.0333 (9)	0.0011 (7)	0.0076 (6)	−0.0002 (7)
C22	0.0317 (8)	0.0394 (10)	0.0345 (9)	0.0025 (7)	0.0074 (7)	0.0020 (8)
C23	0.0429 (10)	0.0417 (11)	0.0477 (11)	0.0003 (8)	0.0073 (8)	0.0075 (9)
C24	0.0461 (11)	0.0408 (11)	0.0605 (13)	−0.0048 (9)	0.0074 (10)	0.0008 (10)
C25	0.0375 (9)	0.0464 (11)	0.0463 (11)	−0.0026 (8)	0.0062 (8)	−0.0075 (9)
C26	0.0325 (8)	0.0456 (11)	0.0342 (9)	0.0005 (7)	0.0066 (7)	−0.0038 (8)
C27	0.0311 (8)	0.0431 (10)	0.0305 (8)	0.0038 (7)	0.0070 (6)	0.0070 (8)
N21	0.0318 (7)	0.0427 (9)	0.0271 (7)	0.0009 (6)	0.0045 (6)	0.0015 (6)
C28	0.0430 (10)	0.0553 (12)	0.0271 (9)	−0.0048 (9)	0.0032 (7)	0.0012 (9)

Geometric parameters (Å, º) top

V1—O11	1.9183 (13)	C13—H13	0.9500
V1—O1	1.9227 (14)	C14—C15	1.390 (4)
V1—O21	1.9641 (13)	C14—H14	0.9500
V1—N1	2.1126 (15)	C15—C16	1.386 (3)
V1—N11	2.1163 (16)	C15—H15	0.9500
V1—N21	2.1625 (15)	C16—H16	0.9500
O1—C1	1.318 (2)	C17—N11	1.281 (3)
C1—C6	1.408 (3)	C17—H17	0.9500
C1—C2	1.415 (3)	N11—C18	1.467 (2)
C2—C3	1.414 (3)	C18—H18A	0.9800
C2—C7	1.439 (3)	C18—H18B	0.9800
C3—C4	1.371 (3)	C18—H18C	0.9800
C3—H3	0.9500	O21—C21	1.310 (2)
C4—C5	1.389 (4)	C21—C22	1.412 (3)
C4—H4	0.9500	C21—C26	1.414 (2)
C5—C6	1.376 (3)	C22—C23	1.402 (3)
C5—H5	0.9500	C22—C27	1.447 (3)
C6—H6	0.9500	C23—C24	1.379 (3)
C7—N1	1.290 (2)	C23—H23	0.9500
C7—H7	0.9500	C24—C25	1.392 (3)
N1—C8	1.463 (2)	C24—H24	0.9500
C8—H8A	0.9800	C25—C26	1.379 (3)
C8—H8B	0.9800	C25—H25	0.9500
C8—H8C	0.9800	C26—H26	0.9500
O11—C11	1.325 (2)	C27—N21	1.284 (2)
C11—C16	1.404 (3)	C27—H27	0.9500
C11—C12	1.420 (3)	N21—C28	1.471 (2)
C12—C13	1.403 (3)	C28—H28A	0.9800
C12—C17	1.446 (3)	C28—H28B	0.9800
C13—C14	1.371 (3)	C28—H28C	0.9800

O11—V1—O1	98.00 (6)	C14—C13—H13	119.2
O11—V1—O21	171.59 (6)	C12—C13—H13	119.2
O1—V1—O21	90.39 (6)	C13—C14—C15	119.2 (2)
O11—V1—N1	87.14 (6)	C13—C14—H14	120.4
O1—V1—N1	88.60 (6)	C15—C14—H14	120.4
O21—V1—N1	92.56 (6)	C16—C15—C14	120.7 (2)
O11—V1—N11	88.49 (6)	C16—C15—H15	119.7
O1—V1—N11	89.82 (6)	C14—C15—H15	119.7
O21—V1—N11	92.09 (6)	C15—C16—C11	121.1 (2)
N1—V1—N11	175.10 (6)	C15—C16—H16	119.4
O11—V1—N21	87.96 (6)	C11—C16—H16	119.4
O1—V1—N21	173.21 (6)	N11—C17—C12	126.48 (19)
O21—V1—N21	83.70 (5)	N11—C17—H17	116.8
N1—V1—N21	94.99 (6)	C12—C17—H17	116.8
N11—V1—N21	87.06 (6)	C17—N11—C18	117.16 (17)
C1—O1—V1	133.07 (12)	C17—N11—V1	125.15 (13)
O1—C1—C6	118.64 (18)	C18—N11—V1	117.65 (13)
O1—C1—C2	122.96 (17)	N11—C18—H18A	109.5
C6—C1—C2	118.39 (18)	N11—C18—H18B	109.5
C3—C2—C1	118.79 (19)	H18A—C18—H18B	109.5
C3—C2—C7	117.42 (19)	N11—C18—H18C	109.5
C1—C2—C7	123.78 (17)	H18A—C18—H18C	109.5
C4—C3—C2	121.6 (2)	H18B—C18—H18C	109.5
C4—C3—H3	119.2	C21—O21—V1	135.69 (11)
C2—C3—H3	119.2	O21—C21—C22	122.67 (16)
C3—C4—C5	119.3 (2)	O21—C21—C26	119.81 (16)
C3—C4—H4	120.3	C22—C21—C26	117.52 (17)
C5—C4—H4	120.3	C23—C22—C21	119.98 (17)
C6—C5—C4	120.8 (2)	C23—C22—C27	117.86 (17)
C6—C5—H5	119.6	C21—C22—C27	122.03 (17)
C4—C5—H5	119.6	C24—C23—C22	121.5 (2)
C5—C6—C1	121.1 (2)	C24—C23—H23	119.3
C5—C6—H6	119.5	C22—C23—H23	119.3
C1—C6—H6	119.5	C23—C24—C25	118.7 (2)
N1—C7—C2	126.67 (18)	C23—C24—H24	120.6
N1—C7—H7	116.7	C25—C24—H24	120.6
C2—C7—H7	116.7	C26—C25—C24	121.06 (19)
C7—N1—C8	116.91 (16)	C26—C25—H25	119.5
C7—N1—V1	124.86 (13)	C24—C25—H25	119.5
C8—N1—V1	118.07 (12)	C25—C26—C21	121.15 (18)
N1—C8—H8A	109.5	C25—C26—H26	119.4
N1—C8—H8B	109.5	C21—C26—H26	119.4
H8A—C8—H8B	109.5	N21—C27—C22	126.46 (17)
N1—C8—H8C	109.5	N21—C27—H27	116.8
H8A—C8—H8C	109.5	C22—C27—H27	116.8
H8B—C8—H8C	109.5	C27—N21—C28	115.14 (16)
C11—O11—V1	132.48 (12)	C27—N21—V1	127.10 (12)
O11—C11—C16	118.88 (19)	C28—N21—V1	117.71 (12)
O11—C11—C12	123.17 (17)	N21—C28—H28A	109.5
C16—C11—C12	117.93 (19)	N21—C28—H28B	109.5
C13—C12—C11	119.37 (19)	H28A—C28—H28B	109.5
C13—C12—C17	117.2 (2)	N21—C28—H28C	109.5
C11—C12—C17	123.40 (18)	H28A—C28—H28C	109.5
C14—C13—C12	121.7 (2)	H28B—C28—H28C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27···O21ⁱ	0.95	2.56	3.431 (2)	153

Symmetry code: (i) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27···O21ⁱ	0.95	2.56	3.431 (2)	153

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

This work was supported by the State of Schleswig-Holstein.

References

Bonadies, J. A. & Carrano, C. J. (1986). J. Am. Chem. Soc. 108, 4088–4095. CrossRef CAS Web of Science Google Scholar
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Cornman, C. R., Geiser–Bush, K. M., Rowley, S. P. & Boyle, P. D. (1997). CrystEngComm, 36, 6401–6408. CAS Google Scholar
Davies, J. E. & Gatehouse, B. M. (1974). J. Chem. Soc. Dalton Trans. pp. 184–187. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Stoe (2008). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. 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 71| Part 12| December 2015| Page m225

https://doi.org/10.1107/S2056989015021453

Open

access