catena-Poly[[(diaqua­zinc)-μ-3-carb­oxy­pyrazine-2-carboxyl­ato-κ4N1,O2;N4,O3] nitrate]

Starosta, W.; Leciejewicz, J.

doi:10.1107/S1600536811054031

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page m75

doi:10.1107/S1600536811054031

Open

access

catena-Poly[[(diaquazinc)-μ-3-carboxypyrazine-2-carboxylato-κ⁴N¹,O²;N⁴,O³] nitrate]

Wojciech Starosta ^a and Janusz Leciejewicz ^a ^*

^aInstitute of Nuclear Chemistry and Technology, ul. Dorodna 16, 03-195 Warszawa, Poland
^*Correspondence e-mail: j.leciejewicz@ichtj.waw.pl

(Received 7 December 2011; accepted 15 December 2011; online 21 December 2011)

The crystal structure of the title compound, {[Zn(C₆H₃N₂O₄)(H₂O)₂]NO₃}_n, is built of zigzag cationic chains propagating in [010] with nitrate anions located in the space between the chains. The Zn^II ion is coordinated by N and O atoms of two symmetry-related ligands in equatorial sites, and by two water O atoms at the axial sites of a distorted octahedron. One carboxylate group of the ligand remains protonated, serving as a donor in a short intramolecular O—H⋯O hydrogen bond. The coordinated water molecules are donors and the nitrate O atoms act as acceptors in a network of O—H⋯O hydrogen bonds.

Related literature

For the crystal structures of Zn^II complexes with pyrazine-2,3-dicarboxylato and aqua ligands, see: Richard et al. (1974 ); Ptasiewicz-Bąk & Leciejewicz (1999 ); Gryz et al. (2005 ).

Experimental

Crystal data

[Zn(C₆H₃N₂O₄)(H₂O)₂]NO₃
M_r = 330.52
Monoclinic, P 2₁ /n
a = 8.7431 (17) Å
b = 10.867 (2) Å
c = 11.412 (2) Å
β = 100.48 (3)°
V = 1066.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.36 mm⁻¹
T = 293 K
0.20 × 0.19 × 0.15 mm

Data collection

Kuma KM-4 four-circle diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.636, T_max = 0.747
3232 measured reflections
3101 independent reflections
2397 reflections with I > 2σ(I)
R_int = 0.012
3 standard reflections every 200 reflections intensity decay: 1.6%

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.097
S = 1.03
3101 reflections
192 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O6	2.052 (2)
Zn1—O5	2.069 (2)
Zn1—O4ⁱ	2.0769 (18)
Zn1—O1	2.0816 (17)
Zn1—N1	2.1663 (18)
Zn1—N2ⁱ	2.1946 (19)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H61⋯O13ⁱⁱ	0.84 (4)	1.90 (4)	2.732 (3)	176 (3)
O5—H52⋯O12ⁱⁱⁱ	0.83 (4)	1.88 (4)	2.696 (3)	169 (4)
O6—H62⋯O11ⁱⁱⁱ	0.72 (5)	2.04 (5)	2.758 (3)	175 (5)
O5—H51⋯O3ⁱⁱ	0.73 (6)	2.37 (5)	2.983 (3)	142 (5)
O5—H51⋯O11ⁱ	0.73 (6)	2.63 (6)	3.094 (4)	123 (5)
O2—H3⋯O3	1.20 (5)	1.22 (5)	2.404 (2)	170 (4)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x-1, y, z.

Data collection: KM-4 Software (Kuma, 1996 $[Kuma (1996). KM-4 Software. Kuma Diffraction Ltd, Wrocław, Poland.]$ ); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma, 2001 $[Kuma (2001). DATAPROC. Kuma Diffraction Ltd, Wrocław, Poland.]$ ); 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/S1600536811054031/kp2377sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811054031/kp2377Isup2.hkl

checkCIF report

Comment top

The structures of three Zn^II coordination compounds with pyrazine-2,3-dicarboxylate ligand (2,3-PZDC), each with a different molecular pattern were reported. In the triclinic structure of Zn(2,3-PZDC)(H₂O)₂.H₂O (Richard et al., 1974) molecular ribbons are observed while the monoclinic Zn(2,3-PZDC)(H₂O)₃.H₂O (Ptasiewicz-Bąk & Leciejewicz, 1999) shows a zigzag catenated molecular pattern. The monoclinic structure of (H₃O)⁺₂ [Zn(2,3-PZDC)^2- is built of catenated doubly layered polyanions with hydronium cations in the interstitials (Gryz et al. 2005). The structure of the title compound is composed of zigzag molecular chains propagating along the crystal b axis in which Zn^II ions are coordinated by N,O chelating groups of two singly deprotonated ligand molecules; their planes make a dihedral angle of 82.1 (1)° each to the other (Fig. 1). Two water O atoms complete the coordination of the Zn^II ion to six, located at the apices of a distorted octahedron. O1, N1, O4ⁱ and O5 atoms form its basal plane with r.m.s. of 0.1408 (2) Å. Zn—O and Zn—N bond lengths are close to those observed in the structures of other Zn complexes with the title ligand (Richard, et al., 1974; Ptasiewicz-Bąk & Leciejewicz, 1999; Gryz, et al., 2005). A pyrazine ring is planar [r.m.s. 0.0146 (2) Å, the carboxylate groups C7/O1/O2 and C8/O3/O4 make with it dihedral angles of 4.8 (1)° and 171.9 (1)°, respectively. One of the carboxylate groups remains protonated and participates in a short, intra-molecular hydrogen bond of 2.404 (2) Å. Consequently, each building unit of the chain shows a singly positive charge which is compensated by a nitrate anion located in the space between chains (Fig. 2). Hydrogen bonds are observed between coordinated water molecules which act as donors and nitrate O atoms as acceptors (Table 2).

Related literature top

For the crystal structures of Zn^II complexes with pyrazine-2,3-dicarboxylate and aqua ligands, see: Richard et al. (1974); Ptasiewicz-Bąk & Leciejewicz (1999); Gryz et al. (2005).

Experimental top

Single crystals of the title compound were found incidently in the course of an attempt to obtain dinuclear magnesium-zinc complex with the pyrazine-2,3-dicarboxylate ligand. A solution containing 2 mmols of pyrazine-2,3-dicarboxylic acid dihydrate, 1 mmol of magnesium nitrate dihydrate and a small excess over 1 mmol of zinc nitrate hexahydrate in 100 mL of doubly distilled water was boiled under reflux with stirring for 10 h. After cooling to room temperature, two drops of 95% hydrazine were added to the solution which was left to crystallise. Colourless single-crystal blocks of the title compound and crystals of Zn(H₂O)₆(NO₃)₂ were found in an unidentified polycrystalline material after evaporation to dryness. The crystals of the title complex were extracted, washed with ethanol and dried in air.

Computing details top

Data collection: KM-4 Software (Kuma, 1996); cell refinement: KM-4 Software (Kuma, 1996); data reduction: DATAPROC (Kuma, 2001); 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. A structural unit of the title compound with atom labelling scheme and 50% probability displacement ellipsoids. Symmetry code: (i) -x + 1/2, y + 1/2,-z + 1/2. An intramolecuular hydrogen bond is shown by dashed lines.
	Fig. 2. Packing diagram of the structure viewed along the c axis.

catena-Poly[[(diaquazinc)-µ-3-carboxypyrazine-2-carboxylato- κ⁴N¹,O²;N⁴,O³] nitrate] top

Crystal data top

[Zn(C₆H₃N₂O₄)(H₂O)₂]NO₃	F(000) = 664
M_r = 330.52	D_x = 2.059 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 8.7431 (17) Å	θ = 6–15°
b = 10.867 (2) Å	µ = 2.36 mm⁻¹
c = 11.412 (2) Å	T = 293 K
β = 100.48 (3)°	Blocks, colourless
V = 1066.2 (4) Å³	0.20 × 0.19 × 0.15 mm
Z = 4

Data collection top

Kuma KM-4 four-circle diffractometer	2397 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.012
Graphite monochromator	θ_max = 30.1°, θ_min = 2.6°
profile data from ω/2θ scans	h = −10→12
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	k = −15→0
T_min = 0.636, T_max = 0.747	l = −16→0
3232 measured reflections	3 standard reflections every 200 reflections
3101 independent reflections	intensity decay: 1.6%

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0564P)² + 0.8069P] where P = (F_o² + 2F_c²)/3
3101 reflections	(Δ/σ)_max = 0.001
192 parameters	Δρ_max = 0.81 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Zn(C₆H₃N₂O₄)(H₂O)₂]NO₃	V = 1066.2 (4) Å³
M_r = 330.52	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.7431 (17) Å	µ = 2.36 mm⁻¹
b = 10.867 (2) Å	T = 293 K
c = 11.412 (2) Å	0.20 × 0.19 × 0.15 mm
β = 100.48 (3)°

Data collection top

Kuma KM-4 four-circle diffractometer	2397 reflections with I > 2σ(I)
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	R_int = 0.012
T_min = 0.636, T_max = 0.747	3 standard reflections every 200 reflections
3232 measured reflections	intensity decay: 1.6%
3101 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.81 e Å⁻³
3101 reflections	Δρ_min = −0.48 e Å⁻³
192 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	−0.00406 (3)	0.82559 (2)	0.26307 (2)	0.02503 (9)
C7	0.0503 (2)	0.68275 (19)	0.06020 (18)	0.0235 (4)
C2	0.1549 (2)	0.61605 (18)	0.16261 (17)	0.0212 (4)
N1	0.1442 (2)	0.66517 (17)	0.26888 (16)	0.0255 (4)
C3	0.2546 (2)	0.51569 (19)	0.15702 (18)	0.0214 (4)
C8	0.3008 (3)	0.45650 (19)	0.04721 (19)	0.0247 (4)
C6	0.2221 (3)	0.6151 (2)	0.36834 (19)	0.0303 (5)
H6	0.2153	0.6495	0.4418	0.036*
O5	−0.1653 (2)	0.96368 (18)	0.2120 (2)	0.0403 (4)
N2	0.3300 (2)	0.46525 (17)	0.25858 (16)	0.0246 (3)
O3	0.2334 (2)	0.48857 (16)	−0.05626 (14)	0.0314 (3)
O4	0.4046 (2)	0.37756 (16)	0.06479 (15)	0.0313 (3)
O2	0.0421 (2)	0.64513 (17)	−0.04597 (14)	0.0323 (4)
O1	−0.02615 (19)	0.77131 (15)	0.08585 (14)	0.0295 (3)
O6	−0.1700 (2)	0.71769 (19)	0.3183 (2)	0.0373 (4)
C5	0.3133 (3)	0.5120 (2)	0.36293 (19)	0.0294 (4)
H5	0.3634	0.4752	0.4330	0.035*
O11	0.5234 (3)	0.7166 (3)	0.2043 (2)	0.0568 (6)
O12	0.5562 (3)	0.8786 (3)	0.1012 (3)	0.0758 (9)
O13	0.3449 (2)	0.7771 (2)	0.05949 (19)	0.0463 (5)
N3	0.4762 (2)	0.7915 (2)	0.1237 (2)	0.0366 (5)
H61	−0.166 (4)	0.723 (3)	0.392 (3)	0.035 (8)*
H52	−0.256 (5)	0.946 (4)	0.181 (4)	0.056 (11)*
H62	−0.251 (6)	0.722 (4)	0.289 (4)	0.081 (16)*
H51	−0.165 (6)	1.002 (5)	0.265 (5)	0.095 (19)*
H3	0.143 (5)	0.574 (4)	−0.056 (4)	0.088 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02357 (14)	0.02086 (13)	0.02998 (14)	−0.00042 (9)	0.00303 (9)	−0.00081 (9)
C7	0.0212 (9)	0.0232 (9)	0.0241 (9)	−0.0025 (7)	−0.0014 (7)	0.0015 (7)
C2	0.0199 (8)	0.0202 (8)	0.0224 (9)	−0.0013 (7)	0.0010 (7)	0.0010 (7)
N1	0.0253 (8)	0.0249 (9)	0.0249 (8)	0.0031 (7)	0.0006 (7)	−0.0020 (6)
C3	0.0205 (9)	0.0197 (8)	0.0234 (8)	−0.0014 (7)	0.0022 (7)	−0.0003 (7)
C8	0.0260 (10)	0.0236 (9)	0.0246 (9)	−0.0015 (7)	0.0047 (7)	−0.0003 (7)
C6	0.0353 (11)	0.0328 (11)	0.0214 (9)	0.0080 (9)	0.0016 (8)	−0.0015 (8)
O5	0.0317 (10)	0.0276 (9)	0.0589 (13)	0.0062 (7)	0.0010 (9)	−0.0050 (8)
N2	0.0231 (8)	0.0236 (8)	0.0260 (8)	0.0020 (6)	0.0013 (6)	0.0012 (6)
O3	0.0360 (9)	0.0348 (9)	0.0231 (7)	0.0068 (7)	0.0041 (6)	0.0002 (6)
O4	0.0353 (9)	0.0296 (8)	0.0297 (8)	0.0079 (7)	0.0075 (7)	0.0003 (6)
O2	0.0345 (9)	0.0363 (9)	0.0233 (7)	0.0070 (7)	−0.0022 (6)	−0.0015 (6)
O1	0.0291 (8)	0.0264 (8)	0.0295 (8)	0.0060 (6)	−0.0035 (6)	−0.0009 (6)
O6	0.0315 (10)	0.0400 (10)	0.0393 (11)	−0.0078 (8)	0.0041 (8)	0.0034 (8)
C5	0.0318 (11)	0.0309 (11)	0.0236 (9)	0.0057 (9)	−0.0004 (8)	0.0014 (8)
O11	0.0473 (12)	0.0708 (16)	0.0467 (12)	−0.0080 (11)	−0.0060 (9)	0.0132 (11)
O12	0.0526 (15)	0.0659 (17)	0.100 (2)	−0.0293 (13)	−0.0098 (14)	0.0186 (16)
O13	0.0259 (9)	0.0682 (14)	0.0428 (10)	−0.0089 (9)	0.0006 (8)	0.0042 (10)
N3	0.0265 (10)	0.0452 (12)	0.0379 (11)	−0.0069 (9)	0.0052 (8)	−0.0012 (9)

Geometric parameters (Å, º) top

Zn1—O6	2.052 (2)	C6—C5	1.382 (3)
Zn1—O5	2.069 (2)	C6—H6	0.9300
Zn1—O4ⁱ	2.0769 (18)	O5—H52	0.83 (4)
Zn1—O1	2.0816 (17)	O5—H51	0.73 (6)
Zn1—N1	2.1663 (18)	N2—C5	1.327 (3)
Zn1—N2ⁱ	2.1946 (19)	N2—Zn1ⁱⁱ	2.1947 (19)
C7—O1	1.237 (3)	O3—H3	1.22 (5)
C7—O2	1.268 (3)	O4—Zn1ⁱⁱ	2.0769 (18)
C7—C2	1.529 (3)	O2—H3	1.20 (5)
C2—N1	1.344 (3)	O6—H61	0.84 (4)
C2—C3	1.405 (3)	O6—H62	0.72 (5)
N1—C6	1.330 (3)	C5—H5	0.9300
C3—N2	1.342 (3)	O11—N3	1.241 (3)
C3—C8	1.527 (3)	O12—N3	1.230 (3)
C8—O4	1.238 (3)	O13—N3	1.254 (3)
C8—O3	1.269 (3)

O6—Zn1—O5	90.99 (9)	C2—C3—C8	128.54 (18)
O6—Zn1—O4ⁱ	93.59 (8)	O4—C8—O3	122.9 (2)
O5—Zn1—O4ⁱ	102.46 (9)	O4—C8—C3	117.00 (19)
O6—Zn1—O1	101.00 (8)	O3—C8—C3	120.06 (19)
O5—Zn1—O1	89.65 (9)	N1—C6—C5	120.2 (2)
O4ⁱ—Zn1—O1	160.90 (7)	N1—C6—H6	119.9
O6—Zn1—N1	89.06 (8)	C5—C6—H6	119.9
O5—Zn1—N1	164.96 (9)	Zn1—O5—H52	120 (3)
O4ⁱ—Zn1—N1	92.55 (7)	Zn1—O5—H51	107 (4)
O1—Zn1—N1	75.58 (7)	H52—O5—H51	110 (5)
O6—Zn1—N2ⁱ	166.71 (8)	C5—N2—C3	120.11 (19)
O5—Zn1—N2ⁱ	85.27 (8)	C5—N2—Zn1ⁱⁱ	123.90 (15)
O4ⁱ—Zn1—N2ⁱ	74.86 (7)	C3—N2—Zn1ⁱⁱ	115.27 (14)
O1—Zn1—N2ⁱ	91.74 (7)	C8—O3—H3	114 (2)
N1—Zn1—N2ⁱ	97.85 (7)	C8—O4—Zn1ⁱⁱ	120.67 (15)
O1—C7—O2	122.53 (19)	C7—O2—H3	113 (2)
O1—C7—C2	117.50 (19)	C7—O1—Zn1	119.46 (14)
O2—C7—C2	119.96 (19)	Zn1—O6—H61	112 (2)
N1—C2—C3	119.66 (18)	Zn1—O6—H62	121 (4)
N1—C2—C7	111.79 (18)	H61—O6—H62	108 (4)
C3—C2—C7	128.54 (18)	N2—C5—C6	120.6 (2)
C6—N1—C2	119.93 (19)	N2—C5—H5	119.7
C6—N1—Zn1	124.51 (15)	C6—C5—H5	119.7
C2—N1—Zn1	115.56 (14)	O12—N3—O11	122.2 (2)
N2—C3—C2	119.29 (18)	O12—N3—O13	118.0 (3)
N2—C3—C8	112.05 (18)	O11—N3—O13	119.8 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H61···O13ⁱⁱⁱ	0.84 (4)	1.90 (4)	2.732 (3)	176 (3)
O5—H52···O12^iv	0.83 (4)	1.88 (4)	2.696 (3)	169 (4)
O6—H62···O11^iv	0.72 (5)	2.04 (5)	2.758 (3)	175 (5)
O5—H51···O3ⁱⁱⁱ	0.73 (6)	2.37 (5)	2.983 (3)	142 (5)
O5—H51···O11ⁱ	0.73 (6)	2.63 (6)	3.094 (4)	123 (5)
O2—H3···O3	1.20 (5)	1.22 (5)	2.404 (2)	170 (4)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₆H₃N₂O₄)(H₂O)₂]NO₃
M_r	330.52
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.7431 (17), 10.867 (2), 11.412 (2)
β (°)	100.48 (3)
V (Å³)	1066.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.36
Crystal size (mm)	0.20 × 0.19 × 0.15

Data collection
Diffractometer	Kuma KM-4 four-circle diffractometer
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.636, 0.747
No. of measured, independent and observed [I > 2σ(I)] reflections	3232, 3101, 2397
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.097, 1.03
No. of reflections	3101
No. of parameters	192
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.48

Computer programs: KM-4 Software (Kuma, 1996), DATAPROC (Kuma, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—O6	2.052 (2)	Zn1—O1	2.0816 (17)
Zn1—O5	2.069 (2)	Zn1—N1	2.1663 (18)
Zn1—O4ⁱ	2.0769 (18)	Zn1—N2ⁱ	2.1946 (19)

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H61···O13ⁱⁱ	0.84 (4)	1.90 (4)	2.732 (3)	176 (3)
O5—H52···O12ⁱⁱⁱ	0.83 (4)	1.88 (4)	2.696 (3)	169 (4)
O6—H62···O11ⁱⁱⁱ	0.72 (5)	2.04 (5)	2.758 (3)	175 (5)
O5—H51···O3ⁱⁱ	0.73 (6)	2.37 (5)	2.983 (3)	142 (5)
O5—H51···O11ⁱ	0.73 (6)	2.63 (6)	3.094 (4)	123 (5)
O2—H3···O3	1.20 (5)	1.22 (5)	2.404 (2)	170 (4)

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

References

Gryz, M., Starosta, W. & Leciejewicz, J. (2005). J. Coord. Chem. 58, 931–935. Web of Science CSD CrossRef CAS Google Scholar
Kuma (1996). KM-4 Software. Kuma Diffraction Ltd, Wrocław, Poland. Google Scholar
Kuma (2001). DATAPROC. Kuma Diffraction Ltd, Wrocław, Poland. Google Scholar
Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Ptasiewicz-Bąk, H. & Leciejewicz, J. (1999). Pol. J. Chem. 73, 1887–1893. Google Scholar
Richard, P., Tranqui, D. & Bertaut, E. F. (1974). Acta Cryst. B30, 628–633. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals 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.