2-(2-Furylmethyl­ammonio)ethane­sulfonate methanol solvate

Du, Z.-X.; Wang, L.-Z.

doi:10.1107/S1600536809020005

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1459

doi:10.1107/S1600536809020005

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2-(2-Furylmethylammonio)ethanesulfonate methanol solvate

Zhong-Xiang Du ^a ^* and Ling-Zhi Wang ^b

^aDepartment of Chemistry, Luoyang Normal University, Luoyang, Henan 471022, People's Republic of China, and ^bEquipment Department, Luoyang Normal University, Luoyang, Henan 471022, People's Republic of China
^*Correspondence e-mail: dzx6281@126.com

(Received 23 May 2009; accepted 26 May 2009; online 6 June 2009)

The organic molecule of the title compound, C₇H₁₁NO₄S·CH₃OH, is a zwitterion and its furan ring displays positional disorder [occupancy 0.563 (5):0.437 (5)]. The crystal structure is extended into a three-dimensional supramolecular architecture through intermolecular O—H⋯O and N—H⋯O hydrogen bonds with participation of the methanol solvent molecules.

Related literature

For a number of reduced or unreduced Schiff base complexes derived from taurine, see: Jiang et al. (2004 , 2006 ); Li et al. (2005 , 2006a ,b , 2007a ,b , 2008a ,b ); Liao et al. (2007 ); Zeng et al. (2003 ); Zhang et al. (2005 ). For the crystal stucture of a similar compound, 2-(2-pyridylmethylammonio) ethanesulfonate dihydrate, see: Li et al. (2006b).

Experimental

Crystal data

C₇H₁₁NO₄S·CH₄O
M_r = 237.27
Monoclinic, P 2₁ /c
a = 10.729 (10) Å
b = 9.174 (8) Å
c = 11.270 (10) Å
β = 91.964 (10)°
V = 1108.6 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 294 K
0.39 × 0.23 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.894, T_max = 0.946
7971 measured reflections
2056 independent reflections
1675 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.109
S = 1.06
2056 reflections
131 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O6ⁱ	0.90	1.92	2.767 (3)	156
N1—H1B⋯O2ⁱⁱ	0.90	2.15	2.940 (3)	147
N1—H1B⋯O2ⁱⁱⁱ	0.90	2.39	3.039 (3)	129
O6—H6⋯O4^iv	0.82	1.90	2.720 (3)	175
Symmetry codes: (i) x, y-1, z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020005/at2791sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809020005/at2791Isup2.hkl

checkCIF report

Comment top

In the previous literatures, a number of reduced or unreduced Schiff base complexes derived from taurine have been reported (Jiang et al., 2004, 2006; Li et al., 2005, 2006a, 2007a,b, 2008a,b); Liao et al., 2007; Zeng et al., 2003; Zhang et al., 2005), and they have shown novel chain (Li et al., 2007b), cubical (Li et al., 2008a) and isomeric (Li et al., 2008b) structures except for the commonly seen mononuclear or binuclear compounds. Taurine, an amino acid containing sulfur, is indispensable to human beings and has important physiological functions. However, there have been sparse reports on the crystal structures of the corresponding free Schiff base ligands so far. In this paper, we report the crystal structure of a reduced Schiff base from taurine, (I) (Fig. 1).

The H atom of the sulfonic acid group is transferred to the amino N atom, forming the zwitterionic amino acid. This structure is completely similar to that of 2-(2-pyridylmethylammonio)ethanesulfonate dihydrate (Li et al., 2006b), where the H atom of the sulfonic acid group is also transferred to the amino N atom. The difference between them is that the furan ring here is positionally disordered. The two positions of furan ring have a dihedral angle of 180°. Other bond length and angles are in good agreement. Methanol molecules are involved in hydrogen bonds both as donors and acceptors, whereas ammonium acts only as a double donor (Table 1, Fig.2). Fig. 3 shows the crystal packing of (I), with hydrogen bonds as dashed lines in ac plane. The crystal of (I) is stabilized via these intermolecular hydrogen bonding interactions.

Related literature top

For a number of reduced or unreduced Schiff base complexes derived from taurine, see: Jiang et al. (2004, 2006); Li et al. (2005, 2006a,b, 2007a,b, 2008a,b); Liao et al. (2007); Zeng et al. (2003); Zhang et al. (2005). For the crystal stucture of a similar compound, 2-(2-pyridylmethylammonio) ethanesulfonate dihydrate, see: Li et al. (2006b).

Experimental top

Furan-2-carbaldehyde (0.96 g, 10 mmol) in MeOH (10 ml) was dropwise added to a solution of 2-aminoethanesulfonic acid (1.25 g, 10 mmol) in methanol (10 ml) containing KOH (0.56 g, 10 mmol). The yellow solution was stirred for about 2 h at room temperature prior to cooling in an ice bath. The intermediate Schiff base that formed was reduced with an excess of KBH₄ (0.79 g, 15 mmol). The yellow colour slowly discharged, and after 3 h the solution was adjusted with concentrated HCl to pH = 6.0. The resulting white solid was filtered off, washed with anhydrous methanol and diethyl ether. The obtained solid was dissolved in a ethanol-methanol mixture (1:1 v/v, 20 ml) and heated. When cooling, colourless granular-shaped crystals were obtained in a yield of 76%. Analysis, found: C 40.42, H 6.37, N 5.85, S 13.55%; C₈H₁₅NO₅S requires: C 40.50, H 6.33, N 5.91, S 13.50%. IR (KBr,ν, cm^-1): 768.7[γ(C═C-H)], 741.0(γCH₂); 1210.1, 1147.5, 1040.8(ν SO₃^-); 1607.6(ν C═C); 3428.4(ν O-H); 3098.8, 3021.3(ν N-H).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), with displacement ellipsoids drawn at the 15% probability level.
	Fig. 2. The crystal packing of (I), showing hydrogen bonds as dashed lines in bc plane. H atoms on C atoms have been omitted.
	Fig. 3. The crystal packing of (I), showing hydrogen bonds as dashed lines in ac plane. H atoms on C atoms have been omitted.

2-(2-Furylmethylammonio)ethanesulfonate methanol solvate top

Crystal data top

C₇H₁₁NO₄S·CH₄O	F(000) = 504
M_r = 237.27	D_x = 1.422 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2624 reflections
a = 10.729 (10) Å	θ = 2.9–26.3°
b = 9.174 (8) Å	µ = 0.29 mm⁻¹
c = 11.27 (1) Å	T = 294 K
β = 91.964 (10)°	Granular, colourless
V = 1108.6 (17) Å³	0.39 × 0.23 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	2056 independent reflections
Radiation source: fine-focus sealed tube	1675 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.894, T_max = 0.946	k = −11→11
7971 measured reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0435P)² + 0.7985P] where P = (F_o² + 2F_c²)/3
2056 reflections	(Δ/σ)_max = 0.001
131 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₇H₁₁NO₄S·CH₄O	V = 1108.6 (17) Å³
M_r = 237.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.729 (10) Å	µ = 0.29 mm⁻¹
b = 9.174 (8) Å	T = 294 K
c = 11.27 (1) Å	0.39 × 0.23 × 0.19 mm
β = 91.964 (10)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2056 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1675 reflections with I > 2σ(I)
T_min = 0.894, T_max = 0.946	R_int = 0.025
7971 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.06	Δρ_max = 0.34 e Å⁻³
2056 reflections	Δρ_min = −0.31 e Å⁻³
131 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.15887 (16)	0.40087 (19)	1.03366 (18)	0.0405 (5)	0.563 (5)
C2	0.06631 (19)	0.3384 (3)	1.0916 (3)	0.0555 (12)	0.563 (5)
H2	0.0190	0.2592	1.0650	0.067*	0.563 (5)
C3	0.0522 (3)	0.4135 (4)	1.2010 (2)	0.0573 (19)	0.563 (5)
H3	−0.0047	0.3950	1.2595	0.069*	0.563 (5)
C4	0.1395 (4)	0.5157 (4)	1.1997 (2)	0.0619 (14)	0.563 (5)
H4	0.1532	0.5825	1.2608	0.074*	0.563 (5)
O1	0.2068 (3)	0.5129 (2)	1.0994 (2)	0.0578 (9)	0.563 (5)
O1'	0.0572 (2)	0.3157 (3)	1.0589 (3)	0.0578 (9)	0.437 (5)
C1'	0.15442 (16)	0.40368 (19)	1.03098 (18)	0.0405 (5)	0.437 (5)
C2'	0.1761 (2)	0.4964 (2)	1.11987 (19)	0.0555 (12)	0.437 (5)
H2'	0.2380	0.5675	1.1222	0.067*	0.437 (5)
C3'	0.0903 (3)	0.4705 (4)	1.2108 (2)	0.0573 (19)	0.437 (5)
H3'	0.0832	0.5187	1.2828	0.069*	0.437 (5)
C4'	0.0230 (3)	0.3605 (4)	1.1674 (3)	0.0619 (14)	0.437 (5)
H4'	−0.0418	0.3180	1.2078	0.074*	0.437 (5)
C5	0.2106 (2)	0.3793 (3)	0.9149 (2)	0.0455 (6)
H5A	0.1911	0.4519	0.8546	0.055*
H5B	0.1656	0.2896	0.8977	0.055*
C6	0.3852 (2)	0.2834 (3)	0.80019 (19)	0.0389 (5)
H6A	0.3740	0.3697	0.7512	0.047*
H6B	0.3372	0.2049	0.7635	0.047*
C7	0.5215 (2)	0.2421 (3)	0.80631 (19)	0.0385 (5)
H7A	0.5316	0.1509	0.8491	0.046*
H7B	0.5684	0.3165	0.8497	0.046*
N1	0.33791 (17)	0.3130 (2)	0.92132 (16)	0.0366 (4)
H1A	0.3355	0.2290	0.9624	0.044*
H1B	0.3908	0.3739	0.9604	0.044*
O2	0.51984 (16)	0.09645 (19)	0.60803 (14)	0.0475 (4)
O3	0.71519 (15)	0.2028 (2)	0.67984 (16)	0.0547 (5)
O4	0.54838 (17)	0.35667 (19)	0.59804 (16)	0.0541 (5)
S1	0.58193 (5)	0.22288 (6)	0.66156 (5)	0.03640 (19)
C8	0.1847 (3)	0.9586 (4)	0.0474 (3)	0.0661 (8)
H8A	0.2158	0.9121	0.1187	0.099*
H8B	0.1539	0.8861	−0.0075	0.099*
H8C	0.1184	1.0241	0.0660	0.099*
O6	0.2791 (2)	1.0353 (2)	−0.0028 (3)	0.0841 (8)
H6	0.3274	0.9783	−0.0334	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0334 (12)	0.0395 (13)	0.0489 (14)	0.0009 (10)	0.0043 (10)	−0.0021 (11)
C2	0.054 (3)	0.057 (3)	0.056 (3)	−0.021 (2)	0.008 (2)	−0.008 (2)
C3	0.053 (3)	0.075 (5)	0.0450 (19)	0.007 (3)	0.015 (2)	−0.008 (3)
C4	0.065 (3)	0.071 (3)	0.051 (2)	0.007 (3)	0.016 (2)	−0.007 (2)
O1	0.0508 (17)	0.0572 (19)	0.0662 (18)	−0.0150 (15)	0.0137 (14)	−0.0136 (15)
O1'	0.0508 (17)	0.0572 (19)	0.0662 (18)	−0.0150 (15)	0.0137 (14)	−0.0136 (15)
C1'	0.0334 (12)	0.0395 (13)	0.0489 (14)	0.0009 (10)	0.0043 (10)	−0.0021 (11)
C2'	0.054 (3)	0.057 (3)	0.056 (3)	−0.021 (2)	0.008 (2)	−0.008 (2)
C3'	0.053 (3)	0.075 (5)	0.0450 (19)	0.007 (3)	0.015 (2)	−0.008 (3)
C4'	0.065 (3)	0.071 (3)	0.051 (2)	0.007 (3)	0.016 (2)	−0.007 (2)
C5	0.0374 (13)	0.0510 (15)	0.0482 (14)	0.0053 (11)	0.0042 (10)	0.0031 (11)
C6	0.0411 (12)	0.0455 (14)	0.0302 (11)	−0.0025 (10)	0.0026 (9)	−0.0033 (10)
C7	0.0417 (12)	0.0456 (13)	0.0282 (11)	0.0026 (10)	0.0018 (9)	−0.0035 (10)
N1	0.0373 (10)	0.0374 (10)	0.0351 (10)	−0.0016 (8)	0.0036 (8)	−0.0042 (8)
O2	0.0572 (11)	0.0450 (10)	0.0400 (9)	−0.0009 (8)	−0.0020 (8)	−0.0118 (7)
O3	0.0383 (9)	0.0731 (13)	0.0530 (11)	0.0057 (9)	0.0040 (8)	−0.0093 (9)
O4	0.0659 (12)	0.0465 (11)	0.0507 (10)	0.0079 (9)	0.0144 (9)	0.0144 (8)
S1	0.0405 (3)	0.0390 (3)	0.0299 (3)	0.0022 (2)	0.0039 (2)	−0.0017 (2)
C8	0.0571 (17)	0.068 (2)	0.074 (2)	−0.0017 (15)	0.0079 (15)	0.0062 (16)
O6	0.0751 (15)	0.0432 (11)	0.137 (2)	0.0023 (11)	0.0486 (14)	0.0045 (13)

Geometric parameters (Å, º) top

C1—C2	1.3365 (17)	C5—H5A	0.9700
C1—O1	1.3579 (17)	C5—H5B	0.9700
C1—C5	1.479 (3)	C6—N1	1.497 (3)
C2—C3	1.4241 (19)	C6—C7	1.510 (3)
C2—H2	0.9300	C6—H6A	0.9700
C3—C4	1.3255 (17)	C6—H6B	0.9700
C3—H3	0.9300	C7—S1	1.785 (3)
C4—O1	1.3616 (18)	C7—H7A	0.9700
C4—H4	0.9300	C7—H7B	0.9700
O1'—C4'	1.3528 (18)	N1—H1A	0.9000
O1'—C1'	1.3636 (18)	N1—H1B	0.9000
C1'—C2'	1.3288 (17)	O2—S1	1.4579 (19)
C1'—C5	1.476 (3)	O3—S1	1.449 (2)
C2'—C3'	1.4210 (18)	O4—S1	1.460 (2)
C2'—H2'	0.9300	C8—O6	1.371 (3)
C3'—C4'	1.3242 (17)	C8—H8A	0.9600
C3'—H3'	0.9300	C8—H8B	0.9600
C4'—H4'	0.9300	C8—H8C	0.9600
C5—N1	1.494 (3)	O6—H6	0.8200

C2—C1—O1	109.4	N1—C5—H5B	96.4
C2—C1—C5	133.87 (18)	H5A—C5—H5B	110.4
O1—C1—C5	116.63 (19)	N1—C6—C7	111.21 (18)
C1—C2—C3	108.6	N1—C6—H6A	109.4
C1—C2—H2	125.7	C7—C6—H6A	109.4
C3—C2—H2	125.7	N1—C6—H6B	109.4
C4—C3—C2	103.7	C7—C6—H6B	109.4
C4—C3—H3	128.2	H6A—C6—H6B	108.0
C2—C3—H3	128.2	C6—C7—S1	111.39 (15)
C3—C4—O1	113.0	C6—C7—H7A	109.3
C3—C4—H4	123.5	S1—C7—H7A	109.3
O1—C4—H4	123.5	C6—C7—H7B	109.3
C1—O1—C4	105.4	S1—C7—H7B	109.3
C4'—O1'—C1'	105.2	H7A—C7—H7B	108.0
C2'—C1'—O1'	108.7	C5—N1—C6	111.57 (17)
C2'—C1'—C5	134.33 (19)	C5—N1—H1A	109.3
O1'—C1'—C5	116.98 (18)	C6—N1—H1A	109.3
C1'—C2'—C3'	109.6	C5—N1—H1B	109.3
C1'—C2'—H2'	125.2	C6—N1—H1B	109.3
C3'—C2'—H2'	125.2	H1A—N1—H1B	108.0
C4'—C3'—C2'	102.7	O3—S1—O2	113.08 (11)
C4'—C3'—H3'	128.6	O3—S1—O4	113.72 (12)
C2'—C3'—H3'	128.6	O2—S1—O4	111.38 (12)
C3'—C4'—O1'	113.8	O3—S1—C7	105.68 (11)
C3'—C4'—H4'	123.1	O2—S1—C7	106.36 (11)
O1'—C4'—H4'	123.1	O4—S1—C7	105.89 (11)
C1'—C5—N1	114.81 (19)	O6—C8—H8A	109.5
C1—C5—N1	112.44 (19)	O6—C8—H8B	109.5
C1'—C5—H5A	115.6	H8A—C8—H8B	109.5
C1—C5—H5A	117.6	O6—C8—H8C	109.5
N1—C5—H5A	119.2	H8A—C8—H8C	109.5
C1'—C5—H5B	95.2	H8B—C8—H8C	109.5
C1—C5—H5B	95.5	C8—O6—H6	109.5

O1—C1—C2—C3	0.2	O1'—C1'—C5—C1	−105.89 (12)
C5—C1—C2—C3	−175.1 (3)	C2'—C1'—C5—N1	71.6 (3)
C1—C2—C3—C4	−0.4	O1'—C1'—C5—N1	−108.9 (2)
C2—C3—C4—O1	0.4	C2—C1—C5—C1'	72.75 (19)
C2—C1—O1—C4	0.0	O1—C1—C5—C1'	−102.27 (13)
C5—C1—O1—C4	176.2 (2)	C2—C1—C5—N1	−110.2 (2)
C3—C4—O1—C1	−0.3	O1—C1—C5—N1	74.7 (2)
C4'—O1'—C1'—C2'	0.0	N1—C6—C7—S1	−174.72 (15)
C4'—O1'—C1'—C5	−179.6 (2)	C1'—C5—N1—C6	176.54 (19)
O1'—C1'—C2'—C3'	−0.2	C1—C5—N1—C6	176.41 (18)
C5—C1'—C2'—C3'	179.3 (3)	C7—C6—N1—C5	169.8 (2)
C1'—C2'—C3'—C4'	0.3	C6—C7—S1—O3	172.61 (17)
C2'—C3'—C4'—O1'	−0.3	C6—C7—S1—O2	−66.9 (2)
C1'—O1'—C4'—C3'	0.2	C6—C7—S1—O4	51.7 (2)
C2'—C1'—C5—C1	74.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O6ⁱ	0.90	1.92	2.767 (3)	156
N1—H1B···O2ⁱⁱ	0.90	2.15	2.940 (3)	147
N1—H1B···O2ⁱⁱⁱ	0.90	2.39	3.039 (3)	129
O6—H6···O4^iv	0.82	1.90	2.720 (3)	175

Symmetry codes: (i) x, y−1, z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₇H₁₁NO₄S·CH₄O
M_r	237.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	10.729 (10), 9.174 (8), 11.27 (1)
β (°)	91.964 (10)
V (Å³)	1108.6 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.39 × 0.23 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.894, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	7971, 2056, 1675
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.109, 1.06
No. of reflections	2056
No. of parameters	131
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.31

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O6ⁱ	0.90	1.92	2.767 (3)	155.7
N1—H1B···O2ⁱⁱ	0.90	2.15	2.940 (3)	146.9
N1—H1B···O2ⁱⁱⁱ	0.90	2.39	3.039 (3)	128.6
O6—H6···O4^iv	0.82	1.90	2.720 (3)	174.7

Symmetry codes: (i) x, y−1, z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, y+1/2, −z+1/2.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20471026) and the Natural Science Foundation of Henan Province (No. 0311021200).

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jiang, Y.-M., Li, J.-M., Xie, F.-Q. & Wang, Y.-F. (2006). Chin. J. Struct. Chem. 25, 767–770. CAS Google Scholar
Jiang, Y.-M., Zeng, J.-L. & Yu, K.-B. (2004). Acta Cryst. C60, m543–m545. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Li, J.-X., Jiang, Y.-M. & Chen, M.-J. (2008a). J. Coord. Chem. 61, 1765–1773. Web of Science CSD CrossRef CAS Google Scholar
Li, J.-X., Jiang, Y.-M. & Li, H.-Y. (2006a). Acta Cryst. E62, m2984–m2986. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, J.-X., Jiang, Y.-M. & Lian, B.-R. (2008b). J. Chem. Crystallogr. 38, 711–715. Web of Science CSD CrossRef CAS Google Scholar
Li, J.-X., Jiang, Y.-M. & Liao, B.-L. (2006b). Acta Cryst. E62, o5609–o5611. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, J.-X., Jiang, Y.-M. & Wang, J.-G. (2007a). Acta Cryst. E63, m213–m215. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, J.-X., Jiang, Y.-M. & Wang, J.-G. (2007b). Acta Cryst. E63, m601–m603. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, J.-M., Jiang, Y.-M., Wang, Y.-F. & Liang, D.-W. (2005). Acta Cryst. E61, m2160–m2162. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liao, B.-L., Li, J.-X. & Jiang, Y.-M. (2007). Acta Cryst. E63, m1974. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zeng, J.-L., Jiang, Y.-M. & Yu, K.-B. (2003). Acta Cryst. E59, m1137–m1139. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, S.-H., Jiang, Y.-M. & Yu, K.-B. (2005). Acta Cryst. E61, m209–m211. CSD CrossRef IUCr Journals Google Scholar