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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o161
https://doi.org/10.1107/S1600536807064768

4,4′-Di­methyl-2,2′-[1,2-phenyl­enebis(nitrilo­methyl­­idyne)]diphenol

Ke-Wei Lei,a* Hai-Mei Fenga and Tian-Hua Zhoua

aState Key Laboratory Base of Novel Functional Materials and Preparation Science, Institute of Solid Materials Chemistry, Faculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, People's Republic of China
*Correspondence e-mail: leikeweipublic@hotmail.com

(Received 12 November 2007; accepted 30 November 2007; online 6 December 2007)

In the title Schiff base, C22H20N2O2, the benzene ring forms dihedral angles of 53.92 (1) and 3.62 (1)° with the two salicylaldimine groups. There are two strong O—H⋯N intra­molecular hydrogen bonds. The crystal packing is stabilized by weak inter­molecular C—H⋯O hydrogen bonds and π–π stacking inter­actions (average distance 3.39 Å).

Related literature

For related literature, see: Cohen et al. (1964[Cohen, M. D., Schmidt, G. M. J. & Flavian, S. (1964). J. Chem. Soc. pp. 2041-2043.]).

[Scheme 1]

Experimental

Crystal data

  • C22H20N2O2

  • Mr = 344.40

  • Monoclinic, P 21 /c

  • a = 6.0835 (12) Å

  • b = 16.207 (3) Å

  • c = 18.607 (4) Å

  • β = 98.28 (3)°

  • V = 1815.4 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 (2) K

  • 0.33 × 0.28 × 0.21 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.971, Tmax = 0.985

  • 17288 measured reflections

  • 4063 independent reflections

  • 2571 reflections with I > 2σ(I)

  • Rint = 0.037
Refinement

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.134

  • S = 1.03

  • 4063 reflections

  • 237 parameters

  • H-atom parameters constrained

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯N1 0.82 1.87 2.595 (2) 147
O2—H2A⋯N2 0.82 1.86 2.5880 (19) 147
C8—H8A⋯O1i 0.93 2.56 3.407 (2) 152
C18—H18A⋯O1ii 0.93 2.54 3.359 (2) 146
Symmetry codes: (i) x+1, y, z; (ii) -x, -y+2, -z.

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Bruker, 1997[Bruker (1997). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807064768/gk2120sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064768/gk2120Isup2.hkl

checkCIF report


Comment top

Schiff bases have been used extensively as ligands in the field of coordination chemistry. Some of the reasons are that the intramolecular hydrogen bond between the O and N atoms plays an important role in the formation of metal complexes, and that Schiff base compounds show photochromism and thermochromism in the solid state by proton transfer from the hydroxyl O atom to the imine N atom (Cohen et al., 1964). On the basis of structural studies on photochromic and thermochromic salicylaldimine derivatives it was concluded that there is a significant difference in crydtal packing of these molecules: molecules exhibiting thermochromism are planar while those showing photochromism are non-planar (Cohen et al., 1964). In other words, photochromic salicylideneanilines are packed rather loosely in the crystal, in which nonplanar molecules may undergo some conformational changes, while thermochromic salicylideneanilines are packed tightly to form one-dimensional columns. With the aim of gaining a deeper insight into the structural aspects responsible for the observed phenomenon in the solid state, conformational and crystallographic analysis of the non-planar tetra-dentate title compound (I), has been carried out and the results are presented in this paper.

The molecular structure of (I) is illustrated in Fig. 1.

The title molecule is not planar. The salicylaldimine groups C1—C7 (A) and C16—C22 (B) are twisted relative to the phenylene spacer and the angles between the spacer and the salicylaldimino parts A and B are 53.92 (1) and 3.62 (1)°, respectively. The dihedral angle between the salicylaldimine groups A and B is equal to 56.23 (2)°.

In the title molecule there are intramolecular hydrogen bonds between between O1 and N1 and between O2 and N2 atoms (Table 1). Clearly, the enolimine tautomer is favoured over the ketamine form. The crystal packing is stabilized by weak intermolecular hydrogen bonds C—H···O (Table 1) and π···π stacking interactions between benzene ring and salicylaldimine group B.

Related literature top

For related literature, see: Cohen et al. (1964).

Experimental top

1,2-Phenylenediamine(0.01 mol, 1.08 g) and 5-methylsalicylaldehyde (0.02 mol, 2.76 g) were dissolved in ethanol and the solution was refluxed for 3 h. After evaporation, a crude product was recrystallized twice from ethanol to give a pure yellow product. Yield: 90.1%. Melting point: 494–496 K. Calcd. for C22H20N2O2: C, 76.72; H, 5.85; N, 8.13; Found: C, 76.44; H, 5.75; N, 8.07%.

Refinement top

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms (C—H = 0.93 Å or 0.96 Å; O—H = 0.82 Å) and Uiso(H) values equal to 1.2Ueq(C) or 1.5Ueq(O).

Structure description top

Schiff bases have been used extensively as ligands in the field of coordination chemistry. Some of the reasons are that the intramolecular hydrogen bond between the O and N atoms plays an important role in the formation of metal complexes, and that Schiff base compounds show photochromism and thermochromism in the solid state by proton transfer from the hydroxyl O atom to the imine N atom (Cohen et al., 1964). On the basis of structural studies on photochromic and thermochromic salicylaldimine derivatives it was concluded that there is a significant difference in crydtal packing of these molecules: molecules exhibiting thermochromism are planar while those showing photochromism are non-planar (Cohen et al., 1964). In other words, photochromic salicylideneanilines are packed rather loosely in the crystal, in which nonplanar molecules may undergo some conformational changes, while thermochromic salicylideneanilines are packed tightly to form one-dimensional columns. With the aim of gaining a deeper insight into the structural aspects responsible for the observed phenomenon in the solid state, conformational and crystallographic analysis of the non-planar tetra-dentate title compound (I), has been carried out and the results are presented in this paper.

The molecular structure of (I) is illustrated in Fig. 1.

The title molecule is not planar. The salicylaldimine groups C1—C7 (A) and C16—C22 (B) are twisted relative to the phenylene spacer and the angles between the spacer and the salicylaldimino parts A and B are 53.92 (1) and 3.62 (1)°, respectively. The dihedral angle between the salicylaldimine groups A and B is equal to 56.23 (2)°.

In the title molecule there are intramolecular hydrogen bonds between between O1 and N1 and between O2 and N2 atoms (Table 1). Clearly, the enolimine tautomer is favoured over the ketamine form. The crystal packing is stabilized by weak intermolecular hydrogen bonds C—H···O (Table 1) and π···π stacking interactions between benzene ring and salicylaldimine group B.

For related literature, see: Cohen et al. (1964).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. A view of crystal packing of (I).
4,4'-Dimethyl-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenol top
Crystal data top
C22H20N2O2F(000) = 728
Mr = 344.40Dx = 1.260 Mg m−3
Monoclinic, P21/cMelting point = 494–496 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 6.0835 (12) ÅCell parameters from 8652 reflections
b = 16.207 (3) Åθ = 1.0–27.4°
c = 18.607 (4) ŵ = 0.08 mm−1
β = 98.28 (3)°T = 296 K
V = 1815.4 (6) Å3Block, orange
Z = 40.33 × 0.29 × 0.21 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer		4063 independent reflections
Radiation source: fine-focus sealed tube2571 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 0 pixels mm-1θmax = 27.4°, θmin = 3.4°
ω scansh = −7→7
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −21→21
Tmin = 0.971, Tmax = 0.985l = −24→23
17288 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0577P)2 + 0.235P]
where P = (Fo2 + 2Fc2)/3
4063 reflections(Δ/σ)max = 0.003
237 parametersΔρmax = 0.17 e Å−3
0 restraintsΔρmin = −0.15 e Å−3
Crystal data top
C22H20N2O2V = 1815.4 (6) Å3
Mr = 344.40Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.0835 (12) ŵ = 0.08 mm−1
b = 16.207 (3) ÅT = 296 K
c = 18.607 (4) Å0.33 × 0.29 × 0.21 mm
β = 98.28 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		4063 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		2571 reflections with I > 2σ(I)
Tmin = 0.971, Tmax = 0.985Rint = 0.037
17288 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.134H-atom parameters constrained
S = 1.03Δρmax = 0.17 e Å−3
4063 reflectionsΔρmin = −0.15 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
xyzUiso*/Ueq
N10.4005 (2)0.75760 (9)0.02195 (8)0.0530 (4)
O10.1506 (2)0.88529 (8)−0.01297 (7)0.0731 (4)
H10.25200.8526−0.01550.110*
C10.7385 (4)1.07183 (14)−0.30763 (12)0.0790 (6)
H1B0.88851.0532−0.30720.118*
H1C0.73851.1210−0.27890.118*
H1D0.67291.0834−0.35660.118*
O20.2200 (2)0.82823 (8)−0.19143 (7)0.0677 (4)
H2A0.29210.8046−0.15680.101*
N20.5699 (2)0.78862 (9)−0.10188 (7)0.0535 (4)
C20.6061 (3)1.00555 (11)−0.27638 (9)0.0562 (4)
C30.3863 (3)0.99007 (11)−0.30589 (10)0.0606 (5)
H3A0.32321.0202−0.34620.073*
C40.2594 (3)0.93154 (11)−0.27725 (9)0.0586 (5)
H4A0.11260.9233−0.29790.070*
C50.3491 (3)0.88514 (11)−0.21800 (9)0.0508 (4)
C60.5724 (3)0.89744 (11)−0.18760 (8)0.0489 (4)
C70.6942 (3)0.95853 (11)−0.21748 (9)0.0564 (4)
H7A0.84060.9678−0.19680.068*
C80.6787 (3)0.84472 (11)−0.12984 (9)0.0534 (4)
H8A0.82890.8518−0.11280.064*
C90.6778 (3)0.72943 (10)−0.05323 (9)0.0509 (4)
C100.8666 (3)0.68766 (11)−0.06801 (10)0.0592 (5)
H10A0.93400.7028−0.10780.071*
C110.9537 (3)0.62385 (12)−0.02361 (10)0.0645 (5)
H11A1.08010.5962−0.03340.077*
C120.8537 (3)0.60120 (12)0.03489 (11)0.0677 (5)
H12A0.91060.55720.06380.081*
C130.6707 (3)0.64270 (11)0.05125 (10)0.0638 (5)
H13A0.60630.62710.09160.077*
C140.5802 (3)0.70811 (10)0.00797 (9)0.0510 (4)
C150.2992 (3)0.74716 (11)0.07654 (9)0.0540 (4)
H15A0.34310.70420.10860.065*
C160.1188 (3)0.79963 (10)0.09036 (9)0.0513 (4)
C170.0497 (3)0.86653 (11)0.04521 (10)0.0562 (4)
C18−0.1276 (3)0.91440 (12)0.05974 (11)0.0683 (5)
H18A−0.17300.95940.03030.082*
C19−0.2366 (3)0.89569 (12)0.11747 (11)0.0653 (5)
H19A−0.35550.92840.12630.078*
C20−0.1739 (3)0.82931 (11)0.16301 (10)0.0588 (5)
C210.0043 (3)0.78327 (11)0.14885 (9)0.0570 (4)
H21A0.05100.73930.17940.068*
C22−0.2979 (4)0.80766 (14)0.22487 (11)0.0806 (6)
H22A−0.45400.81630.21020.121*
H22B−0.24700.84210.26590.121*
H22C−0.27160.75080.23790.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0519 (8)0.0496 (8)0.0578 (9)0.0005 (6)0.0092 (7)0.0059 (7)
O10.0760 (9)0.0649 (9)0.0824 (9)0.0113 (7)0.0251 (8)0.0276 (7)
C10.0820 (14)0.0738 (14)0.0866 (15)0.0036 (11)0.0310 (12)0.0169 (11)
O20.0551 (7)0.0724 (9)0.0716 (8)−0.0099 (6)−0.0041 (6)0.0130 (7)
N20.0525 (8)0.0601 (9)0.0469 (8)0.0036 (7)0.0038 (7)0.0036 (7)
C20.0619 (11)0.0549 (10)0.0544 (10)0.0081 (8)0.0171 (9)0.0018 (8)
C30.0725 (12)0.0574 (11)0.0504 (10)0.0143 (9)0.0041 (9)0.0025 (8)
C40.0548 (10)0.0607 (11)0.0565 (10)0.0056 (8)−0.0045 (9)−0.0004 (9)
C50.0512 (9)0.0506 (10)0.0500 (9)0.0011 (8)0.0053 (8)−0.0026 (7)
C60.0475 (9)0.0560 (10)0.0437 (8)0.0048 (7)0.0078 (7)−0.0014 (7)
C70.0471 (9)0.0641 (11)0.0589 (10)0.0022 (8)0.0107 (8)−0.0010 (9)
C80.0473 (9)0.0643 (11)0.0475 (9)0.0049 (8)0.0036 (8)−0.0017 (8)
C90.0511 (9)0.0503 (10)0.0490 (9)0.0011 (8)−0.0009 (8)−0.0022 (8)
C100.0597 (11)0.0635 (12)0.0533 (10)0.0061 (9)0.0047 (9)−0.0083 (9)
C110.0679 (12)0.0572 (11)0.0660 (12)0.0145 (9)0.0013 (10)−0.0120 (9)
C120.0792 (13)0.0463 (10)0.0740 (13)0.0137 (9)−0.0010 (11)0.0017 (9)
C130.0757 (13)0.0504 (10)0.0653 (11)0.0052 (9)0.0107 (10)0.0085 (9)
C140.0522 (9)0.0442 (9)0.0549 (10)−0.0001 (7)0.0023 (8)−0.0009 (7)
C150.0586 (10)0.0496 (10)0.0521 (10)0.0027 (8)0.0022 (9)0.0041 (8)
C160.0555 (10)0.0460 (9)0.0512 (9)−0.0030 (7)0.0031 (8)0.0001 (7)
C170.0591 (10)0.0482 (10)0.0620 (11)−0.0025 (8)0.0109 (9)0.0058 (8)
C180.0733 (12)0.0493 (11)0.0827 (13)0.0088 (9)0.0126 (11)0.0116 (10)
C190.0643 (11)0.0550 (11)0.0779 (13)0.0041 (9)0.0152 (10)−0.0081 (10)
C200.0677 (11)0.0542 (11)0.0555 (10)−0.0013 (9)0.0120 (9)−0.0073 (8)
C210.0695 (11)0.0522 (10)0.0484 (10)0.0027 (9)0.0052 (9)0.0031 (8)
C220.0953 (16)0.0850 (16)0.0665 (13)0.0006 (12)0.0286 (12)−0.0062 (11)
Geometric parameters (Å, º) top
N1—C151.273 (2)C9—C141.401 (2)
N1—C141.410 (2)C10—C111.381 (3)
O1—C171.353 (2)C10—H10A0.9300
O1—H10.8200C11—C121.371 (3)
C1—C21.509 (3)C11—H11A0.9300
C1—H1B0.9600C12—C131.372 (3)
C1—H1C0.9600C12—H12A0.9300
C1—H1D0.9600C13—C141.396 (2)
O2—C51.350 (2)C13—H13A0.9300
O2—H2A0.8200C15—C161.440 (2)
N2—C81.279 (2)C15—H15A0.9300
N2—C91.414 (2)C16—C171.399 (2)
C2—C71.379 (2)C16—C211.399 (2)
C2—C31.393 (3)C17—C181.387 (3)
C3—C41.378 (3)C18—C191.375 (3)
C3—H3A0.9300C18—H18A0.9300
C4—C51.380 (2)C19—C201.388 (3)
C4—H4A0.9300C19—H19A0.9300
C5—C61.409 (2)C20—C211.373 (3)
C6—C71.399 (2)C20—C221.505 (3)
C6—C81.450 (2)C21—H21A0.9300
C7—H7A0.9300C22—H22A0.9600
C8—H8A0.9300C22—H22B0.9600
C9—C101.394 (2)C22—H22C0.9600
C15—N1—C14123.29 (15)C12—C11—H11A120.0
C17—O1—H1109.5C10—C11—H11A120.0
C2—C1—H1B109.5C11—C12—C13120.79 (18)
C2—C1—H1C109.5C11—C12—H12A119.6
H1B—C1—H1C109.5C13—C12—H12A119.6
C2—C1—H1D109.5C12—C13—C14120.65 (18)
H1B—C1—H1D109.5C12—C13—H13A119.7
H1C—C1—H1D109.5C14—C13—H13A119.7
C5—O2—H2A109.5C13—C14—C9118.56 (16)
C8—N2—C9121.53 (15)C13—C14—N1125.29 (16)
C7—C2—C3117.08 (17)C9—C14—N1116.11 (15)
C7—C2—C1122.12 (18)N1—C15—C16122.20 (16)
C3—C2—C1120.80 (17)N1—C15—H15A118.9
C4—C3—C2122.07 (17)C16—C15—H15A118.9
C4—C3—H3A119.0C17—C16—C21118.29 (16)
C2—C3—H3A119.0C17—C16—C15121.41 (16)
C3—C4—C5120.33 (17)C21—C16—C15120.28 (16)
C3—C4—H4A119.8O1—C17—C18119.03 (16)
C5—C4—H4A119.8O1—C17—C16121.53 (16)
O2—C5—C4118.72 (15)C18—C17—C16119.43 (16)
O2—C5—C6121.86 (15)C19—C18—C17120.35 (18)
C4—C5—C6119.41 (16)C19—C18—H18A119.8
C7—C6—C5118.43 (15)C17—C18—H18A119.8
C7—C6—C8120.42 (16)C18—C19—C20121.79 (18)
C5—C6—C8121.03 (16)C18—C19—H19A119.1
C2—C7—C6122.65 (17)C20—C19—H19A119.1
C2—C7—H7A118.7C21—C20—C19117.33 (17)
C6—C7—H7A118.7C21—C20—C22121.10 (18)
N2—C8—C6121.25 (16)C19—C20—C22121.57 (18)
N2—C8—H8A119.4C20—C21—C16122.80 (17)
C6—C8—H8A119.4C20—C21—H21A118.6
C10—C9—C14119.88 (16)C16—C21—H21A118.6
C10—C9—N2121.52 (15)C20—C22—H22A109.5
C14—C9—N2118.39 (15)C20—C22—H22B109.5
C11—C10—C9120.10 (17)H22A—C22—H22B109.5
C11—C10—H10A119.9C20—C22—H22C109.5
C9—C10—H10A119.9H22A—C22—H22C109.5
C12—C11—C10119.97 (18)H22B—C22—H22C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.872.595 (2)147
O2—H2A···N20.821.862.5880 (19)147
C8—H8A···O1i0.932.563.407 (2)152
C18—H18A···O1ii0.932.543.359 (2)146
Symmetry codes: (i) x+1, y, z; (ii) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formulaC22H20N2O2
Mr344.40
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)6.0835 (12), 16.207 (3), 18.607 (4)
β (°) 98.28 (3)
V (Å3)1815.4 (6)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.33 × 0.29 × 0.21
Data collection
DiffractometerRigaku R-AXIS RAPID
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.971, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections		17288, 4063, 2571
Rint0.037
(sin θ/λ)max (Å−1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.134, 1.03
No. of reflections4063
No. of parameters237
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.17, −0.15

Computer programs: RAPID-AUTO (Rigaku, 1998), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.872.595 (2)147
O2—H2A···N20.821.862.5880 (19)147
C8—H8A···O1i0.932.563.407 (2)152
C18—H18A···O1ii0.932.543.359 (2)146
Symmetry codes: (i) x+1, y, z; (ii) −x, −y+2, −z.
 

Acknowledgements

This project was supported by the Talent Fund of Ningbo University (grant No. 2006668).

References

First citationBruker (1997). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCohen, M. D., Schmidt, G. M. J. & Flavian, S. (1964). J. Chem. Soc. pp. 2041–2043.  CrossRef Web of Science Google Scholar
 First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationRigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
 First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  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.

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ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o161
https://doi.org/10.1107/S1600536807064768
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