Diaqua­bis­[5-(pyrazin-2-yl)-3-(pyridin-4-yl)-1H-1,2,4-triazol-1-ido-κN1]zinc

Li, B.; Liu, P.-W.; Chen, J.

doi:10.1107/S1600536812002061

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page m203

doi:10.1107/S1600536812002061

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Diaquabis[5-(pyrazin-2-yl)-3-(pyridin-4-yl)-1H-1,2,4-triazol-1-ido-κN¹]zinc

Bo Li,^a Peng-Wen Liu ^a and Jing Chen ^a ^*

^aCollege of Chemistry, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Tianjin Normal University, Tianjin 300387, People's Republic of China
^*Correspondence e-mail: hxxychj@mail.tjnu.edu.cn

(Received 11 January 2012; accepted 17 January 2012; online 25 January 2012)

The title mononuclear complex, [Zn(C₁₁H₇N₆)₂(H₂O)₂], is composed of one Zn^II ion, two deprotonated ppt ligands [Hppt = 5-(pyrazin-2-yl)-3-(pyridin-4-yl)-1H-1,2,4-triazole] and two coordinating water molecules. The asymmetric unit consists of one half-molecule that is completed by application of a centre of symmetry. The Zn^II atom is six-coordinated in an octahedral environment, surrounded by two O atoms in the axial positions and four N atoms in the equatorial plane. Adjacent mononuclear units are further linked via O—H⋯N hydrogen-bonding interactions, forming a two-dimensional network along (100).

Related literature

For the use of multidentate ligands containing N-donor heterocyclic groups in the preparation of metal complexes, see: Du et al. (2006 ); Li et al. (2010 , 2011 ); Wang et al. (2012 ). For crystal structures based on the 5-(pyrazin-2-yl)-3-(pyridin-4-yl)-1H-1,2,4-triazole ligand, see: Liu et al. (2009 ).

Experimental

Crystal data

[Zn(C₁₁H₇N₆)₂(H₂O)₂]
M_r = 547.85
Monoclinic, P 2₁ /c
a = 10.568 (10) Å
b = 12.574 (11) Å
c = 9.373 (8) Å
β = 114.483 (14)°
V = 1133.5 (17) Å³
Z = 2
Mo Kα radiation
μ = 1.13 mm⁻¹
T = 296 K
0.28 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1996 ) T_min = 0.742, T_max = 0.805
5516 measured reflections
1995 independent reflections
1476 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.100
S = 1.13
1995 reflections
170 parameters
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −1.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯N5ⁱ	0.85	1.99	2.833 (4)	173
O1—H1A⋯N2ⁱⁱ	0.85	2.13	2.975 (4)	175
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{5\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812002061/vm2152sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002061/vm2152Isup2.hkl

checkCIF report

Comment top

Multidentate ligands containing N-donor heterocyclic groups, such as the pyridyl, pyrazinyl, imidazolyl, oxadiazolyl, and triazolyl (see Du et al., 2006; Li et al., 2010; Li et al., 2011;Wang et al., 2012), have been widely used to prepare diverse metallo supramolecular complexes. In this context, 5-(pyrazin-2-yl)-3-(pyridin-4-yl)-1H-1,2,4-triazole (Hppt), an asymmetric ligand with multiple binding sites, has attracted little attention thus far (see Liu et al., 2009). Herein, we report on the title complex [Zn(ppt)₂(H₂O)₂] crystallizing in the monoclinic space group P2₁/c, which shows a mononuclear coordination motif and H-bonding supramolecular layers.

The molecular structure of the title complex is centrosymmetric. As illustrated in Fig. 1, the asymmetric unit of this mononuclear complex is provided by a half-occupied Zn^II center as well as one deprotonated ppt and one water ligands. The Zn^II ion is six-coordinated to four nitrogen atoms from two ppt ligands with the Zn—N distances of 2.040 (3) Å and 2.212 (3) Å, as well as two axial water molecules with the Zn—O distance of 2.252 (3) Å. The deprotonated ppt ligand adopts the chelating coordination mode by using the pyrazinyl and triazolyl groups with the N1—Zn1—N3 angle of 77.52 (11)°.

As shown in Fig. 2, the adjacent mononuclear molecules are further linked to form a two-dimensional network via O1—H1A···N2ⁱⁱ [symmetry operation (ii) = -x+2, y-1/2, -z+5/2] hydrogen bonding between the water ligands and the uncoordinated pyrazinyl nitrogen atoms, as well as O1—H1B···N5ⁱ [symmetry operation (i) = x, -y+1/2, z+1/2] between the water ligands and 4-position nitrogen atoms of triazole (Table 1). Furthermore, intralayered π···π stacking interactions are also observed between the triazole (N3, N4, N5, C5, C6) and pyrazine (N1, N2, C1—C4) rings with the center-to-center distance of 3.558 (4) Å and dihedral angle between both best planes of 9.5 (2) °, as well as between the triazole ring (N3, N4, N5, C5, C6) and pyridyl groups (N6, C7—C11) with the center-to-center distance of 3.807 (4) Å and dihedral angle of 8.5 (2) °.

Related literature top

For the use of multidentate ligands containing N-donor heterocyclic groups in the preparation of metal complexes, see: Du et al. (2006); Li et al. (2010, 2011); Wang et al. (2012). For crystal structures based on the 5-(pyrazin-2-yl)-3-(pyridin-4-yl)-1H-1,2,4-triazole ligand, see: Liu et al. (2009).

Experimental top

A CH₃OH solution (3 ml) of Hppt (11.2 mg, 0.05 mmol) was carefully layered onto an aqueous solution of Zn(OAc)₂.2H₂O (21.9 mg, 0.1 mmol) in a straight glass tube. After evaporating the solvents slowly for ca 1 week, colorless block single crystals suitable for X-ray analysis were produced. Analysis, calculated for C₂₂H₁₈ZnN₁₂O₂: C, 48.23; H, 3.31; N, 30.68%; found: C, 49.05; H, 3.38; N, 30.59%.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title complex showing displacement ellipsoids for all non-H atoms drawn at the 30% probability level. [Symmetry code (A): -x+2, -y, -z+2.]
	Fig. 2. View of the two-dimensional network connected via O–H···N hydrogen bonds (red dashed lines).

Diaquabis[5-(pyrazin-2-yl)-3-(pyridin-4-yl)-1H-1,2,4-triazol-1-ido- κN¹]zinc top

Crystal data top

[Zn(C₁₁H₇N₆)₂(H₂O)₂]	F(000) = 560
M_r = 547.85	D_x = 1.605 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2124 reflections
a = 10.568 (10) Å	θ = 2.1–27.2°
b = 12.574 (11) Å	µ = 1.13 mm⁻¹
c = 9.373 (8) Å	T = 296 K
β = 114.483 (14)°	Block, colourless
V = 1133.5 (17) Å³	0.28 × 0.22 × 0.20 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	1995 independent reflections
Radiation source: fine-focus sealed tube	1476 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
phi and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1996)	h = −9→12
T_min = 0.742, T_max = 0.805	k = −12→14
5516 measured reflections	l = −11→8

Refinement top

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0319P)² + 1.4706P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max < 0.001
1995 reflections	Δρ_max = 0.78 e Å⁻³
170 parameters	Δρ_min = −1.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0049 (8)

Crystal data top

[Zn(C₁₁H₇N₆)₂(H₂O)₂]	V = 1133.5 (17) Å³
M_r = 547.85	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.568 (10) Å	µ = 1.13 mm⁻¹
b = 12.574 (11) Å	T = 296 K
c = 9.373 (8) Å	0.28 × 0.22 × 0.20 mm
β = 114.483 (14)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1995 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1996)	1476 reflections with I > 2σ(I)
T_min = 0.742, T_max = 0.805	R_int = 0.032
5516 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.13	Δρ_max = 0.78 e Å⁻³
1995 reflections	Δρ_min = −1.16 e Å⁻³
170 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
Zn1	1.0000	0.0000	1.0000	0.0345 (2)
O1	0.8507 (3)	0.03619 (18)	1.1088 (3)	0.0401 (7)
H1A	0.8598	−0.0073	1.1819	0.060*
H1B	0.8382	0.1011	1.1252	0.060*
N1	1.0865 (3)	0.1612 (2)	1.0734 (3)	0.0289 (7)
N2	1.1330 (4)	0.3772 (2)	1.1491 (3)	0.0373 (8)
N3	0.8842 (3)	0.0902 (2)	0.8093 (3)	0.0315 (7)
N4	0.7855 (3)	0.0703 (2)	0.6615 (3)	0.0339 (8)
N5	0.8335 (3)	0.2478 (2)	0.6850 (3)	0.0279 (7)
N6	0.4516 (4)	0.1950 (3)	0.1161 (4)	0.0556 (10)
C1	1.1805 (4)	0.1930 (3)	1.2132 (4)	0.0335 (9)
H1	1.2312	0.1424	1.2872	0.040*
C2	1.2040 (4)	0.3003 (3)	1.2501 (4)	0.0370 (9)
H2	1.2712	0.3196	1.3481	0.044*
C3	1.0395 (4)	0.3452 (3)	1.0079 (4)	0.0346 (10)
H3	0.9898	0.3963	0.9342	0.042*
C4	1.0145 (4)	0.2375 (3)	0.9682 (3)	0.0270 (8)
C5	0.9116 (4)	0.1956 (2)	0.8199 (3)	0.0269 (8)
C6	0.7575 (4)	0.1661 (2)	0.5912 (4)	0.0286 (8)
C7	0.6541 (4)	0.1783 (3)	0.4281 (4)	0.0325 (9)
C8	0.6080 (4)	0.2768 (3)	0.3576 (4)	0.0385 (10)
H8	0.6421	0.3394	0.4131	0.046*
C9	0.5105 (5)	0.2796 (3)	0.2035 (4)	0.0462 (11)
H9	0.4840	0.3461	0.1573	0.055*
C10	0.4974 (6)	0.1014 (4)	0.1848 (5)	0.0703 (16)
H10	0.4603	0.0403	0.1264	0.084*
C11	0.5966 (5)	0.0888 (3)	0.3376 (4)	0.0611 (14)
H11	0.6241	0.0212	0.3788	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0508 (4)	0.0163 (3)	0.0241 (3)	0.0012 (3)	0.0031 (3)	0.0024 (2)
O1	0.064 (2)	0.0205 (12)	0.0351 (13)	0.0068 (12)	0.0202 (13)	0.0035 (10)
N1	0.037 (2)	0.0235 (15)	0.0227 (14)	0.0021 (13)	0.0087 (13)	−0.0003 (11)
N2	0.048 (2)	0.0283 (16)	0.0275 (15)	−0.0072 (14)	0.0081 (14)	−0.0059 (12)
N3	0.044 (2)	0.0180 (15)	0.0244 (14)	−0.0005 (13)	0.0063 (13)	0.0009 (11)
N4	0.046 (2)	0.0230 (15)	0.0229 (14)	−0.0020 (14)	0.0039 (13)	0.0004 (11)
N5	0.0378 (19)	0.0204 (14)	0.0219 (13)	0.0003 (13)	0.0089 (13)	0.0017 (11)
N6	0.058 (3)	0.067 (3)	0.0285 (17)	−0.003 (2)	0.0046 (16)	0.0041 (17)
C1	0.037 (2)	0.033 (2)	0.0236 (17)	0.0025 (17)	0.0055 (16)	0.0005 (14)
C2	0.044 (3)	0.036 (2)	0.0243 (16)	−0.0060 (18)	0.0069 (16)	−0.0065 (15)
C3	0.050 (3)	0.0229 (18)	0.0250 (16)	−0.0016 (16)	0.0094 (18)	0.0020 (14)
C4	0.039 (2)	0.0207 (17)	0.0214 (16)	0.0010 (15)	0.0123 (15)	0.0009 (12)
C5	0.039 (2)	0.0180 (16)	0.0228 (16)	0.0014 (15)	0.0116 (15)	0.0009 (13)
C6	0.037 (2)	0.0223 (17)	0.0244 (16)	−0.0002 (15)	0.0103 (15)	0.0013 (13)
C7	0.042 (2)	0.0292 (19)	0.0235 (16)	−0.0015 (17)	0.0115 (16)	0.0006 (14)
C8	0.047 (3)	0.033 (2)	0.0306 (18)	0.0029 (18)	0.0116 (18)	0.0024 (15)
C9	0.047 (3)	0.052 (3)	0.034 (2)	0.009 (2)	0.0109 (19)	0.0141 (18)
C10	0.090 (4)	0.054 (3)	0.036 (2)	−0.018 (3)	−0.005 (2)	−0.008 (2)
C11	0.088 (4)	0.034 (2)	0.037 (2)	−0.009 (2)	0.001 (2)	0.0009 (18)

Geometric parameters (Å, º) top

Zn1—N3	2.040 (3)	N6—C9	1.329 (5)
Zn1—N3ⁱ	2.040 (3)	N6—C10	1.332 (6)
Zn1—N1ⁱ	2.212 (3)	C1—C2	1.390 (5)
Zn1—N1	2.212 (3)	C1—H1	0.9300
Zn1—O1	2.252 (3)	C2—H2	0.9300
Zn1—O1ⁱ	2.252 (3)	C3—C4	1.401 (5)
O1—H1A	0.8501	C3—H3	0.9300
O1—H1B	0.8502	C4—C5	1.463 (5)
N1—C1	1.336 (4)	C6—C7	1.474 (5)
N1—C4	1.361 (4)	C7—C11	1.388 (5)
N2—C2	1.343 (5)	C7—C8	1.393 (5)
N2—C3	1.343 (4)	C8—C9	1.385 (5)
N3—C5	1.352 (4)	C8—H8	0.9300
N3—N4	1.368 (4)	C9—H9	0.9300
N4—C6	1.346 (4)	C10—C11	1.390 (6)
N5—C5	1.359 (4)	C10—H10	0.9300
N5—C6	1.375 (4)	C11—H11	0.9300

N3—Zn1—N3ⁱ	180.00 (12)	N2—C2—C1	122.2 (3)
N3—Zn1—N1ⁱ	102.48 (11)	N2—C2—H2	118.9
N3ⁱ—Zn1—N1ⁱ	77.52 (11)	C1—C2—H2	118.9
N3—Zn1—N1	77.52 (11)	N2—C3—C4	122.1 (3)
N3ⁱ—Zn1—N1	102.48 (11)	N2—C3—H3	118.9
N1ⁱ—Zn1—N1	180.0	C4—C3—H3	118.9
N3—Zn1—O1	90.35 (12)	N1—C4—C3	120.1 (3)
N3ⁱ—Zn1—O1	89.65 (12)	N1—C4—C5	114.0 (3)
N1ⁱ—Zn1—O1	92.83 (11)	C3—C4—C5	125.8 (3)
N1—Zn1—O1	87.17 (11)	N3—C5—N5	112.2 (3)
N3—Zn1—O1ⁱ	89.65 (12)	N3—C5—C4	118.4 (3)
N3ⁱ—Zn1—O1ⁱ	90.35 (12)	N5—C5—C4	129.5 (3)
N1ⁱ—Zn1—O1ⁱ	87.17 (11)	N4—C6—N5	113.9 (3)
N1—Zn1—O1ⁱ	92.83 (11)	N4—C6—C7	121.3 (3)
O1—Zn1—O1ⁱ	180.0	N5—C6—C7	124.8 (3)
Zn1—O1—H1A	111.6	C11—C7—C8	116.9 (3)
Zn1—O1—H1B	117.7	C11—C7—C6	119.9 (3)
H1A—O1—H1B	116.5	C8—C7—C6	123.2 (3)
C1—N1—C4	117.7 (3)	C9—C8—C7	118.7 (3)
C1—N1—Zn1	128.5 (2)	C9—C8—H8	120.7
C4—N1—Zn1	112.7 (2)	C7—C8—H8	120.7
C2—N2—C3	116.6 (3)	N6—C9—C8	125.4 (4)
C5—N3—N4	107.7 (3)	N6—C9—H9	117.3
C5—N3—Zn1	116.6 (2)	C8—C9—H9	117.3
N4—N3—Zn1	135.6 (2)	N6—C10—C11	124.5 (4)
C6—N4—N3	104.6 (3)	N6—C10—H10	117.7
C5—N5—C6	101.6 (3)	C11—C10—H10	117.7
C9—N6—C10	115.2 (3)	C7—C11—C10	119.3 (4)
N1—C1—C2	121.3 (3)	C7—C11—H11	120.3
N1—C1—H1	119.4	C10—C11—H11	120.3
C2—C1—H1	119.4

N3—Zn1—N1—C1	173.8 (3)	N2—C3—C4—C5	177.7 (4)
N3ⁱ—Zn1—N1—C1	−6.2 (3)	N4—N3—C5—N5	0.8 (4)
O1—Zn1—N1—C1	82.8 (3)	Zn1—N3—C5—N5	177.4 (2)
O1ⁱ—Zn1—N1—C1	−97.2 (3)	N4—N3—C5—C4	179.8 (3)
N3—Zn1—N1—C4	6.1 (2)	Zn1—N3—C5—C4	−3.6 (4)
N3ⁱ—Zn1—N1—C4	−173.9 (2)	C6—N5—C5—N3	−0.5 (4)
O1—Zn1—N1—C4	−84.9 (2)	C6—N5—C5—C4	−179.4 (4)
O1ⁱ—Zn1—N1—C4	95.1 (2)	N1—C4—C5—N3	9.0 (5)
N1ⁱ—Zn1—N3—C5	178.8 (3)	C3—C4—C5—N3	−169.2 (4)
N1—Zn1—N3—C5	−1.2 (3)	N1—C4—C5—N5	−172.2 (3)
O1—Zn1—N3—C5	85.8 (3)	C3—C4—C5—N5	9.6 (6)
O1ⁱ—Zn1—N3—C5	−94.2 (3)	N3—N4—C6—N5	0.4 (4)
N1ⁱ—Zn1—N3—N4	−5.9 (4)	N3—N4—C6—C7	−179.8 (3)
N1—Zn1—N3—N4	174.1 (4)	C5—N5—C6—N4	0.0 (4)
O1—Zn1—N3—N4	−98.8 (4)	C5—N5—C6—C7	−179.8 (3)
O1ⁱ—Zn1—N3—N4	81.2 (4)	N4—C6—C7—C11	−8.2 (6)
C5—N3—N4—C6	−0.7 (4)	N5—C6—C7—C11	171.6 (4)
Zn1—N3—N4—C6	−176.3 (3)	N4—C6—C7—C8	171.0 (4)
C4—N1—C1—C2	0.1 (5)	N5—C6—C7—C8	−9.2 (6)
Zn1—N1—C1—C2	−167.1 (3)	C11—C7—C8—C9	−0.8 (6)
C3—N2—C2—C1	−1.5 (6)	C6—C7—C8—C9	180.0 (4)
N1—C1—C2—N2	0.8 (6)	C10—N6—C9—C8	−2.9 (7)
C2—N2—C3—C4	1.3 (6)	C7—C8—C9—N6	2.6 (7)
C1—N1—C4—C3	−0.3 (5)	C9—N6—C10—C11	1.5 (8)
Zn1—N1—C4—C3	168.9 (3)	C8—C7—C11—C10	−0.4 (7)
C1—N1—C4—C5	−178.6 (3)	C6—C7—C11—C10	178.9 (5)
Zn1—N1—C4—C5	−9.5 (4)	N6—C10—C11—C7	0.0 (9)
N2—C3—C4—N1	−0.4 (6)

Symmetry code: (i) −x+2, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···N5ⁱⁱ	0.85	1.99	2.833 (4)	173
O1—H1A···N2ⁱⁱⁱ	0.85	2.13	2.975 (4)	175

Symmetry codes: (ii) x, −y+1/2, z+1/2; (iii) −x+2, y−1/2, −z+5/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₁H₇N₆)₂(H₂O)₂]
M_r	547.85
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.568 (10), 12.574 (11), 9.373 (8)
β (°)	114.483 (14)
V (Å³)	1133.5 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.13
Crystal size (mm)	0.28 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1996)
T_min, T_max	0.742, 0.805
No. of measured, independent and observed [I > 2σ(I)] reflections	5516, 1995, 1476
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.100, 1.13
No. of reflections	1995
No. of parameters	170
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −1.16

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···N5ⁱ	0.85	1.99	2.833 (4)	172.7
O1—H1A···N2ⁱⁱ	0.85	2.13	2.975 (4)	175.1

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, y−1/2, −z+5/2.

Acknowledgements

This work was supported financially by Tianjin Normal University (No. 52XQ1104).

References

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