Poly[[(N,N-dimethyl­formamide-κO)(μ3-pyrazine-2,3-dicarboxyl­ato-κ4N1,O2:O3:O3)copper(II)] monohydrate]

Fan, Z.-Z.; Wang, G.-P.; Li, Y.-S.

doi:10.1107/S1600536809051332

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Pages m10-m11

doi:10.1107/S1600536809051332

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Poly[[(N,N-dimethylformamide-κO)(μ₃-pyrazine-2,3-dicarboxylato-κ⁴N¹,O²:O³:O³)copper(II)] monohydrate]

Zhen-Zhong Fan,^a ^* Guo-Ping Wang ^b and Yu-Sheng Li ^c

^aDepartment of Petroleum Engineering, Daqing Petroleum Institute, Heilongjiang 151400, People's Republic of China, ^bDepartment of Chemistry, Zhejiang University, People's Republic of China, and ^cSecond Oil Recovery Plant, Daqing Oilfields Co, Daqing 163414, People's Republic of China
^*Correspondence e-mail: chem8618@126.com

(Received 11 November 2009; accepted 28 November 2009; online 4 December 2009)

In the title compound, {[Cu(C₆H₂N₂O₄)(C₃H₇NO)]·H₂O}_n, the Cu(II) atom is coordinated by an N,O-bidentate pyrazine-2,3-dicarboxylate (pzdc) dianion, two O atoms from two other pzdc anions and one O atom from the dimethlyformamide ligand, forming a distorted square-pyramidal CuNO₄ geometry. The polymeric character of the structure is established by the formation of layers parallel to (100) via bridging pzdc ligands. O—H⋯O hydrogen bonding between water molecules and uncoordinated carboxylate O atoms leads to additional stabilization of the structure.

Related literature

For related structures with the pyrazine-2,3-dicarboxylate (pzdc) dianion, see: Hua & Liu (2009 ); Konar et al. (2004 ); Li et al. (2004 ); Lin et al. (2009 ); Tombul & Guven (2009 ); Wang et al. (2008 ); Xiang et al. (2004 ); Xu et al. (2008 ).

Experimental

Crystal data

[Cu(C₆H₂N₂O₄)(C₃H₇NO)]·H₂O
M_r = 320.75
Monoclinic, P 2₁ /c
a = 10.1656 (5) Å
b = 13.6310 (8) Å
c = 9.1461 (2) Å
β = 91.430 (2)°
V = 1266.96 (10) Å³
Z = 4
Mo Kα radiation
μ = 1.75 mm⁻¹
T = 298 K
0.39 × 0.10 × 0.06 mm

Data collection

Bruker APEX area-detector diffractometer
Absorption correction: integration (SADABS; Bruker, 2002 ) T_min = 0.549, T_max = 0.902
6222 measured reflections
2283 independent reflections
1600 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.115
S = 0.98
2283 reflections
180 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6B⋯O4ⁱ	0.82 (5)	2.00 (3)	2.771 (5)	156 (7)
O6—H6A⋯O1ⁱⁱ	0.82 (5)	2.38 (3)	3.138 (6)	153 (5)
O6—H6A⋯O2ⁱⁱ	0.82 (5)	2.30 (3)	3.037 (5)	149 (5)
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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 I, global. DOI: 10.1107/S1600536809051332/wm2283sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051332/wm2283Isup2.hkl

checkCIF report

Comment top

Polymeric compounds play an important role in the field of molecular magnetism. Di- and polycarboxylates are capable of bridging and providing effective magnetic exchange pathways. Pyrazine-2,3-dicarboxylic acid (H₂pzdc) has been widely applied to construct polymeric coordination compounds; their structures and magnetic properties were investigated (Li et al., 2004; Xiang et al., 2004; Hua & Liu, 2009; Lin et al., 2009; Tombul & Guven, 2009). We present here the structure of the title compound, {[Cu(pzdc)(DMF)]^.H₂O}_n, (I).

In the structure of compound (I), each Cu(II) atom is coordinated by an N atom of the pyrazine ring and a carboxylic O atom from one pzdc^2- anion, two O atoms from two other pzdc^2- anions, and O atom from DMF, forming a distorted square-pyramidal environment, as depicted in Fig. 1. The four atoms N1, O2, O5 and O3ⁱ form the basal plane, whereas the O3ⁱⁱ atom [symmetry code: (i) -x +1, y - 1/2, -z + 1; (ii) x, -y + 3/2, z -1/2] occupies the apical site with a longer Cu1—O3ⁱⁱ bond length of 2.378 (3) /%A. In the basal plane, the bond distances of Cu1—N1 and Cu1—O3ⁱ are 2.002 (3) and 1.958 (3) Å, which are shorter than those observed for the distorted square-pyramidal CuN₂O₃ coordination in a related structure of a Cu(II)pzdc derivative (Hua & Liu, 2009). The plane defined by carboxylic group O1—C1—C2—C3 is nearly coplanar to the pyrazine ring with the dihedral angle of 3.7 (7)°, while another carboxylate plane defined by the C2—C3—C6—O4 is approximately perpendicular to the pyrazine ring [dihedral angel of 92.9 (5)°]. This conformation was also observed in a series of other transition metal complexes formed with H₂pzdc (Li et al., 2004; Xiang et al., 2004; Konar et al., 2004; Hua et al., 2009). Extensive hydrogen bonding interactions help to stabilize the structure. The carboxylate O atoms take part in a O—H···O hydrogen bonding and are acceptor atoms with O atoms of water molecules as donator atoms (Table 1).

Related literature top

For related structures with the pyrazine-2,3-dicarboxylate (pzdc) dianion, see: Hua & Liu (2009); Konar et al. (2004); Li et al. (2004); Lin et al. (2009); Tombul & Guven (2009); Wang et al. (2008); Xiang et al. (2004); Xu et al. (2008).

Experimental top

Mixed DMF and aqueous solution (15 ml) of CuCl₂^.2H₂O (0.5 mmol) and 2,3-pyrazinedicarboxylic acid ((H₂pzdc, 0.25 mmol) were slowly added into a methanolic (5 ml) solution of triethylene diamine (TED, 0.5 mmol); the resulting mixture was stirred for 5 minutes and allowed to stand at room temperature for about four days until blue single crystals were obtained.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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. The coordination of the Cu(II) atom in the structure of compound (I), showing atom labels and 50% probability displacement ellipsoids for the non-H atoms.
	Fig. 2. The polymeric structure of compound (I); water molecules and DMF have been omitted for clarity.

Poly[[(N,N-dimethylformamide-κO)(µ₃-pyrazine-2,3- dicarboxylato-κ⁴N¹,O²:O³:O³)copper(II)] monohydrate] top

Crystal data top

[Cu(C₆H₂N₂O₄)(C₃H₇NO)]·H₂O	F(000) = 652
M_r = 320.75	D_x = 1.682 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1111 reflections
a = 10.1656 (5) Å	θ = 2.5–22.4°
b = 13.6310 (8) Å	µ = 1.75 mm⁻¹
c = 9.1461 (2) Å	T = 298 K
β = 91.430 (2)°	Prism, blue
V = 1266.96 (10) Å³	0.39 × 0.10 × 0.06 mm
Z = 4

Data collection top

Bruker APEX area-detector diffractometer	2283 independent reflections
Radiation source: fine-focus sealed tube	1600 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
phi and ω scans	θ_max = 25.3°, θ_min = 2.0°
Absorption correction: integration (SADABS; Bruker, 2002)	h = −8→12
T_min = 0.549, T_max = 0.902	k = −16→16
6222 measured reflections	l = −10→10

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0482P)²] where P = (F_o² + 2F_c²)/3
2283 reflections	(Δ/σ)_max < 0.001
180 parameters	Δρ_max = 0.48 e Å⁻³
3 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Cu(C₆H₂N₂O₄)(C₃H₇NO)]·H₂O	V = 1266.96 (10) Å³
M_r = 320.75	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.1656 (5) Å	µ = 1.75 mm⁻¹
b = 13.6310 (8) Å	T = 298 K
c = 9.1461 (2) Å	0.39 × 0.10 × 0.06 mm
β = 91.430 (2)°

Data collection top

Bruker APEX area-detector diffractometer	2283 independent reflections
Absorption correction: integration (SADABS; Bruker, 2002)	1600 reflections with I > 2σ(I)
T_min = 0.549, T_max = 0.902	R_int = 0.058
6222 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	3 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.48 e Å⁻³
2283 reflections	Δρ_min = −0.34 e Å⁻³
180 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
Cu1	0.59999 (5)	0.58784 (3)	0.07521 (6)	0.0402 (2)
O1	0.5775 (3)	0.8747 (2)	0.1085 (4)	0.0526 (10)
O2	0.6295 (3)	0.7254 (2)	0.0382 (4)	0.0463 (9)
O3	0.4380 (3)	0.9489 (2)	0.3914 (3)	0.0386 (8)
O4	0.2821 (3)	0.9362 (2)	0.2189 (4)	0.0511 (9)
O5	0.7494 (3)	0.5510 (2)	−0.0435 (4)	0.0503 (9)
O6	0.2218 (5)	0.1287 (3)	0.1467 (7)	0.121 (2)
N1	0.4710 (3)	0.6417 (2)	0.2162 (4)	0.0298 (8)
N2	0.3001 (3)	0.7442 (2)	0.3914 (4)	0.0402 (9)
N3	0.9066 (4)	0.5894 (4)	−0.2048 (5)	0.0655 (13)
C1	0.5654 (4)	0.7859 (3)	0.1145 (5)	0.0331 (10)
C2	0.4684 (4)	0.7404 (3)	0.2158 (4)	0.0279 (9)
C3	0.3821 (4)	0.7913 (3)	0.3018 (5)	0.0316 (10)
C4	0.3064 (4)	0.6467 (3)	0.3912 (5)	0.0420 (12)
H4	0.2516	0.6118	0.4523	0.050*
C5	0.3912 (4)	0.5951 (3)	0.3039 (5)	0.0381 (11)
H5	0.3920	0.5269	0.3071	0.046*
C6	0.3670 (4)	0.9018 (3)	0.3005 (5)	0.0352 (10)
C7	0.8054 (5)	0.6097 (4)	−0.1238 (6)	0.0554 (14)
H7	0.7732	0.6735	−0.1271	0.066*
C8	0.9664 (6)	0.6630 (5)	−0.2983 (8)	0.112 (3)
H8A	0.9216	0.7244	−0.2874	0.168*
H8B	0.9593	0.6421	−0.3985	0.168*
H8C	1.0575	0.6707	−0.2706	0.168*
C9	0.9607 (6)	0.4924 (5)	−0.2062 (7)	0.092 (2)
H9A	1.0486	0.4937	−0.1655	0.137*
H9B	0.9624	0.4688	−0.3051	0.137*
H9C	0.9073	0.4496	−0.1491	0.137*
H6A	0.277 (5)	0.148 (4)	0.089 (6)	0.110*
H6B	0.219 (6)	0.0685 (9)	0.155 (7)	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0472 (4)	0.0182 (3)	0.0560 (4)	0.0032 (2)	0.0188 (3)	0.0026 (3)
O1	0.075 (2)	0.0191 (15)	0.065 (3)	−0.0083 (15)	0.029 (2)	−0.0011 (16)
O2	0.0559 (19)	0.0221 (15)	0.062 (2)	−0.0013 (14)	0.0282 (17)	0.0013 (16)
O3	0.0467 (17)	0.0189 (14)	0.050 (2)	−0.0034 (13)	0.0072 (16)	−0.0062 (15)
O4	0.060 (2)	0.0361 (18)	0.057 (2)	0.0112 (16)	−0.0027 (19)	−0.0003 (17)
O5	0.047 (2)	0.0345 (17)	0.070 (3)	0.0050 (15)	0.0268 (18)	0.0034 (17)
O6	0.102 (4)	0.071 (3)	0.192 (6)	0.010 (3)	0.078 (4)	0.054 (4)
N1	0.0353 (19)	0.0157 (17)	0.039 (2)	−0.0021 (14)	0.0026 (17)	0.0003 (16)
N2	0.049 (2)	0.029 (2)	0.043 (2)	−0.0043 (17)	0.0103 (19)	−0.0032 (18)
N3	0.041 (2)	0.083 (3)	0.074 (4)	0.010 (2)	0.021 (2)	0.004 (3)
C1	0.040 (2)	0.025 (2)	0.034 (3)	−0.0004 (19)	0.008 (2)	−0.002 (2)
C2	0.036 (2)	0.019 (2)	0.029 (3)	−0.0042 (17)	−0.0021 (19)	−0.0008 (18)
C3	0.038 (2)	0.025 (2)	0.032 (3)	−0.0013 (18)	−0.001 (2)	−0.0019 (19)
C4	0.052 (3)	0.030 (2)	0.045 (3)	−0.010 (2)	0.011 (2)	0.002 (2)
C5	0.050 (3)	0.021 (2)	0.044 (3)	−0.004 (2)	0.007 (2)	0.000 (2)
C6	0.039 (2)	0.026 (2)	0.041 (3)	0.004 (2)	0.014 (2)	0.004 (2)
C7	0.043 (3)	0.053 (3)	0.070 (4)	0.009 (2)	0.005 (3)	−0.007 (3)
C8	0.072 (4)	0.144 (7)	0.121 (7)	0.014 (4)	0.049 (4)	0.053 (5)
C9	0.062 (4)	0.098 (5)	0.116 (6)	0.011 (4)	0.030 (4)	−0.050 (4)

Geometric parameters (Å, º) top

Cu1—O2	1.930 (3)	N2—C3	1.346 (5)
Cu1—O5	1.954 (3)	N3—C7	1.313 (6)
Cu1—O3ⁱ	1.958 (3)	N3—C9	1.432 (6)
Cu1—N1	2.002 (3)	N3—C8	1.460 (7)
Cu1—O3ⁱⁱ	2.378 (3)	C1—C2	1.504 (5)
O1—C1	1.218 (5)	C2—C3	1.380 (5)
O2—C1	1.271 (5)	C3—C6	1.515 (5)
O3—C6	1.263 (5)	C4—C5	1.381 (6)
O3—Cu1ⁱⁱⁱ	1.958 (3)	C4—H4	0.9300
O3—Cu1^iv	2.378 (3)	C5—H5	0.9300
O4—C6	1.220 (5)	C7—H7	0.9300
O5—C7	1.235 (6)	C8—H8A	0.9600
O6—H6A	0.82 (5)	C8—H8B	0.9600
O6—H6B	0.82 (5)	C8—H8C	0.9600
N1—C5	1.318 (5)	C9—H9A	0.9600
N1—C2	1.344 (4)	C9—H9B	0.9600
N2—C4	1.331 (5)	C9—H9C	0.9600

O2—Cu1—O5	91.48 (13)	C3—C2—C1	125.4 (4)
O2—Cu1—O3ⁱ	177.39 (13)	N2—C3—C2	121.3 (4)
O5—Cu1—O3ⁱ	89.82 (13)	N2—C3—C6	114.5 (4)
O2—Cu1—N1	82.17 (12)	C2—C3—C6	124.2 (4)
O5—Cu1—N1	169.37 (13)	N2—C4—C5	122.6 (4)
O3ⁱ—Cu1—N1	96.87 (12)	N2—C4—H4	118.7
O2—Cu1—O3ⁱⁱ	100.87 (12)	C5—C4—H4	118.7
O5—Cu1—O3ⁱⁱ	94.99 (12)	N1—C5—C4	120.6 (4)
O3ⁱ—Cu1—O3ⁱⁱ	76.75 (12)	N1—C5—H5	119.7
N1—Cu1—O3ⁱⁱ	94.57 (12)	C4—C5—H5	119.7
C1—O2—Cu1	116.7 (3)	O4—C6—O3	126.2 (4)
C6—O3—Cu1ⁱⁱⁱ	118.9 (3)	O4—C6—C3	117.2 (4)
C6—O3—Cu1^iv	137.1 (3)	O3—C6—C3	116.4 (4)
Cu1ⁱⁱⁱ—O3—Cu1^iv	103.25 (12)	O5—C7—N3	125.4 (5)
C7—O5—Cu1	122.7 (3)	O5—C7—H7	117.3
H6A—O6—H6B	113.5 (19)	N3—C7—H7	117.3
C5—N1—C2	118.1 (4)	N3—C8—H8A	109.5
C5—N1—Cu1	129.7 (3)	N3—C8—H8B	109.5
C2—N1—Cu1	112.2 (3)	H8A—C8—H8B	109.5
C4—N2—C3	116.4 (4)	N3—C8—H8C	109.5
C7—N3—C9	120.4 (5)	H8A—C8—H8C	109.5
C7—N3—C8	121.9 (5)	H8B—C8—H8C	109.5
C9—N3—C8	117.6 (5)	N3—C9—H9A	109.5
O1—C1—O2	124.5 (4)	N3—C9—H9B	109.5
O1—C1—C2	120.4 (4)	H9A—C9—H9B	109.5
O2—C1—C2	115.1 (3)	N3—C9—H9C	109.5
N1—C2—C3	121.0 (4)	H9A—C9—H9C	109.5
N1—C2—C1	113.7 (3)	H9B—C9—H9C	109.5

O5—Cu1—O2—C1	−169.1 (3)	O1—C1—C2—C3	3.7 (7)
O3ⁱ—Cu1—O2—C1	71 (3)	O2—C1—C2—C3	−175.6 (4)
N1—Cu1—O2—C1	2.3 (3)	C4—N2—C3—C2	−0.4 (6)
O3ⁱⁱ—Cu1—O2—C1	95.5 (3)	C4—N2—C3—C6	177.3 (4)
O2—Cu1—O5—C7	−11.7 (4)	N1—C2—C3—N2	1.5 (6)
O3ⁱ—Cu1—O5—C7	166.0 (4)	C1—C2—C3—N2	−178.8 (4)
N1—Cu1—O5—C7	−64.7 (9)	N1—C2—C3—C6	−176.0 (4)
O3ⁱⁱ—Cu1—O5—C7	89.4 (4)	C1—C2—C3—C6	3.7 (7)
O2—Cu1—N1—C5	179.2 (4)	C3—N2—C4—C5	−0.5 (6)
O5—Cu1—N1—C5	−127.0 (7)	C2—N1—C5—C4	0.8 (6)
O3ⁱ—Cu1—N1—C5	1.7 (4)	Cu1—N1—C5—C4	−178.4 (3)
O3ⁱⁱ—Cu1—N1—C5	78.9 (4)	N2—C4—C5—N1	0.3 (7)
O2—Cu1—N1—C2	0.1 (3)	Cu1ⁱⁱⁱ—O3—C6—O4	7.2 (6)
O5—Cu1—N1—C2	53.8 (8)	Cu1^iv—O3—C6—O4	175.4 (3)
O3ⁱ—Cu1—N1—C2	−177.5 (3)	Cu1ⁱⁱⁱ—O3—C6—C3	−167.7 (3)
O3ⁱⁱ—Cu1—N1—C2	−100.3 (3)	Cu1^iv—O3—C6—C3	0.5 (6)
Cu1—O2—C1—O1	176.6 (4)	N2—C3—C6—O4	−84.7 (5)
Cu1—O2—C1—C2	−4.1 (5)	C2—C3—C6—O4	92.9 (5)
C5—N1—C2—C3	−1.6 (6)	N2—C3—C6—O3	90.7 (4)
Cu1—N1—C2—C3	177.6 (3)	C2—C3—C6—O3	−91.7 (5)
C5—N1—C2—C1	178.7 (4)	Cu1—O5—C7—N3	179.4 (4)
Cu1—N1—C2—C1	−2.1 (4)	C9—N3—C7—O5	0.6 (9)
O1—C1—C2—N1	−176.6 (4)	C8—N3—C7—O5	179.3 (6)
O2—C1—C2—N1	4.1 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6B···O4^v	0.82 (5)	2.00 (3)	2.771 (5)	156 (7)
O6—H6A···O1^vi	0.82 (5)	2.38 (3)	3.138 (6)	153 (5)
O6—H6A···O2^vi	0.82 (5)	2.30 (3)	3.037 (5)	149 (5)

Symmetry codes: (v) x, y−1, z; (vi) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Cu(C₆H₂N₂O₄)(C₃H₇NO)]·H₂O
M_r	320.75
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.1656 (5), 13.6310 (8), 9.1461 (2)
β (°)	91.430 (2)
V (Å³)	1266.96 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.75
Crystal size (mm)	0.39 × 0.10 × 0.06

Data collection
Diffractometer	Bruker APEX area-detector diffractometer
Absorption correction	Integration (SADABS; Bruker, 2002)
T_min, T_max	0.549, 0.902
No. of measured, independent and observed [I > 2σ(I)] reflections	6222, 2283, 1600
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.115, 0.98
No. of reflections	2283
No. of parameters	180
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.34

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
O6—H6B···O4ⁱ	0.82 (5)	2.00 (3)	2.771 (5)	156 (7)
O6—H6A···O1ⁱⁱ	0.82 (5)	2.38 (3)	3.138 (6)	153 (5)
O6—H6A···O2ⁱⁱ	0.82 (5)	2.30 (3)	3.037 (5)	149 (5)

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

Acknowledgements

The project was supported by the Natural Science Foundation of Zhejiang Province, China (No. Y407091).

References

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