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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 67| Part 7| July 2011| Page o1626
doi:10.1107/S1600536811021398

Butane-1,2,3,4-tetra­carb­­oxy­lic acid–1,10-phenanthroline–water (1/2/2)

Hong-lin Zhua*

aCenter of Applied Solid State Chemistry Research, Ningbo University, Ningbo, Zhejiang 315211, People's Republic of China
*Correspondence e-mail: zhuhonglin1@nbu.edu.cn

(Received 1 June 2011; accepted 3 June 2011; online 11 June 2011)

The asymmetric unit of the title compound, 2C12H8N2·C8H10O8·2H2O, contains one 1,10-phenanthroline mol­ecule, one half-mol­ecule of butane-1,2,3,4-tetra­carb­oxy­lic acid (H4BTC) and a water mol­ecule, with the complete tetra-acid generated by crystallographic inversion symmetry. Inter­molecular O—H⋯O hydrogen bonds and π–π stacking inter­actions [centroid–centroid distances = 3.672 (2) and 3.708 (2) Å form an extensive three-dimensional network, which consolidates the crystal packing.

Related literature

For the use of H4BTC as a ligand in metal–organic coordination complexes, see: Delgado et al. (2007[Delgado, L. C., Fabelo, O., Pasàn, J., Delgado, F. S., Lloret, F., Julve, M. & Ruiz-Pérez, C. (2007). Inorg. Chem. 46, 7458-7465.]); Liu et al. (2008[Liu, Y. Y., Ma, J. F., Yang, J., Ma, J. C. & Su, Z. M. (2008). CrystEngComm, 10, 894-904.]); Xu et al. (2010[Xu, Y.-Y., Xing, Y.-Y., Duan, X.-Y., Li, Y.-Z., Zhu, H.-Z. & Meng, Q.-J. (2010). CrystEngComm, 12, 567-572.]); Zhu et al. (2011[Zhu, H.-L., Xu, W., Lin, J.-L., Cheng, Y. & Zheng, Y.-Q. (2011). Inorg. Chim. Acta, 366, 27-38.]). For co-crystals involving H4BTC, see: Cheng et al. (2009[Cheng, Y., Wu, J., Zhu, H.-L. & Lin, J. (2009). Acta Cryst. E65, o835.]); Najafpour et al. (2008[Najafpour, M. M., Hołyńska, M. & Lis, T. (2008). Acta Cryst. E64, o985.]). For details of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data

  • 2C12H8N2·C8H10O8·2H2O

  • Mr = 630.60

  • Triclinic, [P \overline 1]

  • a = 7.9472 (16) Å

  • b = 9.884 (2) Å

  • c = 10.628 (2) Å

  • α = 84.37 (3)°

  • β = 70.12 (3)°

  • γ = 72.72 (3)°

  • V = 749.7 (3) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 293 K

  • 0.58 × 0.34 × 0.10 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.950, Tmax = 0.990

  • 7400 measured reflections

  • 3396 independent reflections

  • 1960 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.188

  • S = 1.17

  • 3396 reflections

  • 208 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1A⋯O5iii 0.87 1.70 2.565 (3) 172
O4—H4A⋯N2 0.86 1.90 2.723 (3) 159
O5—H5B⋯O2iv 0.88 1.98 2.817 (3) 160
O5—H5C⋯N1 0.85 2.09 2.858 (3) 149
Symmetry codes: (iii) x-1, y, z; (iv) -x, -y+2, -z+1.

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811021398/sj5157sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021398/sj5157Isup2.hkl

checkCIF report


Comment top

Systems with butane-1,2,3,4-tetracarboxylic acid (H4BTC) as a ligand have been widely studied (Delgado et al., 2007; Liu et al., 2008; Xu et al., 2010; Zhu et al., 2011). A search of the Cambridge structural database (version 5.32, May 2011) (Allen, 2002) showed that most of the literature dealing with butane-1,2,3,4-tetracarboxylic acid concentrated on metal-organic coordination complexes. In contrast, utilization of the butane-1,2,3,4-tetracarboxylic acid seems relatively limited in the construction of co-crystals (Cheng et al., 2009; Najafpour et al., 2008). In this paper, we report the structure of the title cocrystal.

The asymmetric unit of the title cocrystal consists of one 1,10-phenanthroline, unit one half molecule of butane-1,2,3,4-tetracarboxylic acid and a water molecule as depicted in Figure 1. The present 1,10-phenanthroline molecule preserves a nearly perfect coplanarity with a maximum deviation from the best fit meanplane 0.123 (1) Å. The carboxylato group with C1 and C4 atoms is gauche with the C1–C2–C3–C4 torsion angle being 63.35 (2)°. These values agree well with reported structures (Cheng et al., 2009; Najafpour et al., 2008;). The butane-1,2,3,4-tetracarboxylic acid molecules and water molecules are interlinked via O–H···O hydrogen bonds to generate a 1-dimensional supramolecular chain (Figure 2), which is further interconnected by interchain O–H···N hydrogen bonds to construct a 2-dimensional layer parallel to the (001) plane (Figure 3). The resulting layers are arranged in such a way that the 1,10-phenanthroline ligands are each sandwiched between two antiparallel phen neighbors from different adjacent layers, and the mean interplanar distances between the neighboring phen ligands are 3.67 Å and 3.71 Å, suggesting significant intermolecular face-to-face π–π stacking interactions. Such interlayer interactions are regarded as the driving forces to assemble the layers into a three-dimensional supramolecular architecture as shown in Figure 4.

Related literature top

For the use of H4BTC as a ligand in metal–organic coordination complexes, see: Delgado et al.(2007); Liu et al. (2008); Xu et al. (2010); Zhu et al.(2011). For co-crystals involving H4BTC, see: Cheng et al.(2009); Najafpour et al. (2008). For details of the Cambridge Structural Database, see: Allen (2002).

Experimental top

All chemicals were obtained from commerical sources and were used as obtained. 1,10-phenanthroline (0.1983 g, 1.00 mmol) was added to a stirred mixture solution of butane-1,2,3,4-tetracarboxylic acid (0.1173 g, 0.50 mmol) in 10 ml H2O and 10 ml me thanol, and the resulting mixture was stirred for 30 min. Colorless crystals were obtained from the solution after standing at room temperature for two months.

Refinement top

H atoms bonded to C atoms were placed in geometrically calculated positions and were refined using a riding model, with Uiso(H) = 1.2 Ueq(C). H atoms attached to O atoms were found in a difference Fourier synthesis and were refined using a riding model, with the O–H distances fixed as initially found and with Uiso(H) values set at 1.2 Ueq(O).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The content of asymmetric unit showing the atomic numbering and 45% probability displacement ellipsoids [Symmetry codes: (i) -x, -y + 1, -z + 1].
[Figure 2] Fig. 2. Supramolecular assembly of a one-dimensional chain via O–H···O hydrogen bonds.
[Figure 3] Fig. 3. Supramolecular assembly of a two-dimensional layer via O–H···N hydrogen bonds.
[Figure 4] Fig. 4. Supramolecular assembly of three-dimensional architecture through π–π stacking interactions.
Butane-1,2,3,4-tetracarboxylic acid–1,10-phenanthroline–water (1/2/2) top
Crystal data top
2C12H8N2·C8H10O8·2H2OZ = 1
Mr = 630.60F(000) = 330
Triclinic, P1Dx = 1.397 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9472 (16) ÅCell parameters from 4546 reflections
b = 9.884 (2) Åθ = 3.1–27.5°
c = 10.628 (2) ŵ = 0.11 mm−1
α = 84.37 (3)°T = 293 K
β = 70.12 (3)°Block, colorless
γ = 72.72 (3)°0.58 × 0.34 × 0.10 mm
V = 749.7 (3) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer		3396 independent reflections
Radiation source: fine-focus sealed tube1960 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −10→10
Tmin = 0.950, Tmax = 0.990k = −12→12
7400 measured reflectionsl = −13→13
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188H-atom parameters constrained
S = 1.17 w = 1/[σ2(Fo2) + (0.0607P)2 + 0.4694P]
where P = (Fo2 + 2Fc2)/3
3396 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.34 e Å−3
Crystal data top
2C12H8N2·C8H10O8·2H2Oγ = 72.72 (3)°
Mr = 630.60V = 749.7 (3) Å3
Triclinic, P1Z = 1
a = 7.9472 (16) ÅMo Kα radiation
b = 9.884 (2) ŵ = 0.11 mm−1
c = 10.628 (2) ÅT = 293 K
α = 84.37 (3)°0.58 × 0.34 × 0.10 mm
β = 70.12 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		3396 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		1960 reflections with I > 2σ(I)
Tmin = 0.950, Tmax = 0.990Rint = 0.024
7400 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.188H-atom parameters constrained
S = 1.17Δρmax = 0.30 e Å−3
3396 reflectionsΔρmin = −0.34 e Å−3
208 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
O1−0.5184 (3)0.7050 (2)0.4404 (3)0.0745 (7)
H1A−0.58990.79190.44470.089*
O2−0.3498 (3)0.8187 (2)0.4902 (3)0.0734 (7)
C1−0.3757 (4)0.7102 (3)0.4718 (3)0.0434 (6)
C2−0.2475 (4)0.5669 (3)0.4825 (3)0.0484 (6)
H2A−0.22400.51030.40550.058*
H2B−0.30860.52000.56190.058*
C3−0.0619 (3)0.5737 (2)0.4898 (2)0.0389 (5)
H3A−0.08620.63510.56470.047*
C40.0425 (4)0.6356 (2)0.3614 (2)0.0408 (5)
O30.0605 (3)0.5952 (2)0.25216 (19)0.0652 (6)
O40.1121 (3)0.73303 (19)0.37990 (18)0.0532 (5)
H4A0.16390.77060.30540.064*
N10.0963 (3)1.0528 (2)0.2323 (2)0.0514 (6)
C5−0.0353 (5)1.1744 (3)0.2717 (3)0.0613 (8)
H5A−0.08901.19340.36290.074*
C6−0.0969 (5)1.2746 (3)0.1844 (4)0.0705 (9)
H6A−0.19151.35710.21700.085*
C7−0.0175 (5)1.2505 (3)0.0505 (3)0.0677 (9)
H7A−0.05651.3168−0.00960.081*
C80.1230 (4)1.1255 (3)0.0040 (3)0.0546 (7)
C90.2172 (5)1.0959 (4)−0.1356 (3)0.0696 (9)
H9A0.18101.1599−0.19820.084*
C100.3561 (6)0.9781 (4)−0.1774 (3)0.0734 (10)
H10A0.41850.9633−0.26870.088*
C110.4106 (4)0.8744 (3)−0.0853 (3)0.0571 (7)
C120.5552 (5)0.7492 (4)−0.1252 (4)0.0746 (10)
H12A0.62360.7328−0.21540.089*
C130.5961 (5)0.6515 (4)−0.0328 (4)0.0777 (10)
H13A0.69350.5690−0.05860.093*
C140.4888 (5)0.6777 (3)0.1014 (4)0.0709 (9)
H14A0.51490.60930.16390.085*
C150.3153 (4)0.8952 (3)0.0537 (3)0.0466 (6)
C160.1741 (4)1.0267 (3)0.0985 (2)0.0449 (6)
N20.3519 (3)0.7946 (2)0.1444 (2)0.0552 (6)
O50.2570 (3)0.9523 (2)0.4390 (2)0.0597 (6)
H5B0.29321.02750.44040.072*
H5C0.17360.97540.40110.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0631 (13)0.0483 (11)0.131 (2)−0.0092 (10)−0.0622 (14)0.0059 (12)
O20.0697 (14)0.0409 (11)0.124 (2)−0.0077 (10)−0.0544 (14)−0.0078 (11)
C10.0420 (13)0.0434 (13)0.0460 (14)−0.0107 (11)−0.0188 (11)0.0070 (11)
C20.0450 (14)0.0369 (12)0.0677 (17)−0.0104 (11)−0.0269 (13)0.0080 (12)
C30.0394 (12)0.0340 (11)0.0442 (13)−0.0094 (10)−0.0166 (10)0.0046 (10)
C40.0475 (14)0.0363 (12)0.0392 (13)−0.0102 (10)−0.0178 (11)0.0053 (10)
O30.0941 (17)0.0659 (13)0.0441 (11)−0.0352 (12)−0.0239 (11)0.0055 (9)
O40.0683 (13)0.0509 (11)0.0502 (11)−0.0332 (10)−0.0205 (9)0.0110 (8)
N10.0597 (14)0.0524 (13)0.0431 (12)−0.0176 (11)−0.0171 (11)0.0022 (10)
C50.068 (2)0.0575 (17)0.0536 (17)−0.0092 (15)−0.0186 (15)−0.0078 (14)
C60.077 (2)0.0546 (17)0.080 (2)−0.0035 (16)−0.0384 (19)−0.0002 (16)
C70.082 (2)0.0611 (19)0.070 (2)−0.0191 (17)−0.0424 (19)0.0141 (16)
C80.0687 (18)0.0576 (16)0.0503 (16)−0.0299 (15)−0.0282 (14)0.0125 (13)
C90.093 (3)0.083 (2)0.0443 (16)−0.041 (2)−0.0266 (17)0.0164 (16)
C100.091 (3)0.096 (3)0.0380 (15)−0.048 (2)−0.0102 (16)0.0071 (17)
C110.0575 (17)0.0677 (18)0.0488 (16)−0.0326 (15)−0.0060 (13)−0.0067 (14)
C120.066 (2)0.086 (2)0.066 (2)−0.0365 (19)0.0029 (17)−0.0179 (19)
C130.058 (2)0.064 (2)0.098 (3)−0.0149 (16)−0.0048 (19)−0.025 (2)
C140.068 (2)0.0519 (17)0.082 (2)−0.0128 (15)−0.0131 (18)−0.0047 (16)
C150.0533 (15)0.0488 (14)0.0434 (14)−0.0281 (12)−0.0121 (12)0.0034 (11)
C160.0548 (15)0.0496 (14)0.0382 (13)−0.0246 (12)−0.0179 (11)0.0054 (11)
N20.0594 (15)0.0461 (12)0.0576 (14)−0.0170 (11)−0.0144 (12)0.0017 (11)
O50.0634 (13)0.0495 (11)0.0780 (14)−0.0128 (9)−0.0418 (11)0.0047 (10)
Geometric parameters (Å, º) top
O1—C11.302 (3)C7—H7A0.9300
O1—H1A0.8734C8—C161.406 (4)
O2—C11.196 (3)C8—C91.431 (4)
C1—C21.499 (3)C9—C101.333 (5)
C2—C31.525 (3)C9—H9A0.9300
C2—H2A0.9700C10—C111.423 (5)
C2—H2B0.9700C10—H10A0.9300
C3—C41.514 (3)C11—C121.399 (5)
C3—C3i1.540 (4)C11—C151.416 (4)
C3—H3A0.9800C12—C131.359 (5)
C4—O31.214 (3)C12—H12A0.9300
C4—O41.303 (3)C13—C141.393 (5)
O4—H4A0.8635C13—H13A0.9300
N1—C51.330 (4)C14—N21.321 (4)
N1—C161.361 (3)C14—H14A0.9300
C5—C61.387 (4)C15—N21.354 (4)
C5—H5A0.9300C15—C161.438 (4)
C6—C71.359 (5)O5—H5B0.8756
C6—H6A0.9300O5—H5C0.8533
C7—C81.393 (4)
Cg1···Cg3ii3.672 (2)Cg2···Cg3iii3.708 (2)
C1—O1—H1A106.5C7—C8—C16118.4 (3)
O2—C1—O1123.2 (2)C7—C8—C9122.2 (3)
O2—C1—C2123.5 (2)C16—C8—C9119.4 (3)
O1—C1—C2113.4 (2)C10—C9—C8121.1 (3)
C1—C2—C3112.9 (2)C10—C9—H9A119.5
C1—C2—H2A109.0C8—C9—H9A119.5
C3—C2—H2A109.0C9—C10—C11121.3 (3)
C1—C2—H2B109.0C9—C10—H10A119.4
C3—C2—H2B109.0C11—C10—H10A119.4
H2A—C2—H2B107.8C12—C11—C15117.1 (3)
C4—C3—C2109.7 (2)C12—C11—C10123.0 (3)
C4—C3—C3i108.5 (2)C15—C11—C10119.8 (3)
C2—C3—C3i112.0 (2)C13—C12—C11120.3 (3)
C4—C3—H3A108.9C13—C12—H12A119.8
C2—C3—H3A108.9C11—C12—H12A119.8
C3i—C3—H3A108.9C12—C13—C14118.6 (3)
O3—C4—O4124.0 (2)C12—C13—H13A120.7
O3—C4—C3122.1 (2)C14—C13—H13A120.7
O4—C4—C3113.9 (2)N2—C14—C13123.5 (4)
C4—O4—H4A111.9N2—C14—H14A118.2
C5—N1—C16117.5 (2)C13—C14—H14A118.2
N1—C5—C6123.7 (3)N2—C15—C11122.0 (3)
N1—C5—H5A118.1N2—C15—C16119.6 (2)
C6—C5—H5A118.1C11—C15—C16118.5 (3)
C7—C6—C5119.1 (3)N1—C16—C8121.9 (3)
C7—C6—H6A120.4N1—C16—C15118.4 (2)
C5—C6—H6A120.4C8—C16—C15119.7 (2)
C6—C7—C8119.4 (3)C14—N2—C15118.3 (3)
C6—C7—H7A120.3H5B—O5—H5C107.6
C8—C7—H7A120.3
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z; (iii) −x+1, −y+2, −z.
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the N1/C5-C8/C16/, N2/C14-C11/C15, and C8-C11/C15/C16, rings respectively.
D—H···AD—HH···AD···AD—H···A
O1—H1A···O5iv0.871.702.565 (3)172
O4—H4A···N20.861.902.723 (3)159
O5—H5B···O2v0.881.982.817 (3)160
O5—H5C···N10.852.092.858 (3)149
Symmetry codes: (iv) x−1, y, z; (v) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula2C12H8N2·C8H10O8·2H2O
Mr630.60
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.9472 (16), 9.884 (2), 10.628 (2)
α, β, γ (°)84.37 (3), 70.12 (3), 72.72 (3)
V (Å3)749.7 (3)
Z1
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.58 × 0.34 × 0.10
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.950, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections		7400, 3396, 1960
Rint0.024
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.188, 1.17
No. of reflections3396
No. of parameters208
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.30, −0.34

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected interatomic distances (Å) top
Cg1···Cg3i3.672 (2)Cg2···Cg3ii3.708 (2)
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y+2, −z.
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the N1/C5-C8/C16/, N2/C14-C11/C15, and C8-C11/C15/C16, rings respectively.
D—H···AD—HH···AD···AD—H···A
O1—H1A···O5iii0.871.702.565 (3)172
O4—H4A···N20.861.902.723 (3)159
O5—H5B···O2iv0.881.982.817 (3)160
O5—H5C···N10.852.092.858 (3)149
Symmetry codes: (iii) x−1, y, z; (iv) −x, −y+2, −z+1.
 

Acknowledgements

This project was supported by the K. C. Wong Magna Fund of Ningbo University.

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ISSN: 2056-9890
Volume 67| Part 7| July 2011| Page o1626
doi:10.1107/S1600536811021398
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