Diaqua­bis­(2,2′-bi-1H-imidazole)­man­ganese(II) benzene-1,4-di­carboxyl­ate

Yang, L.; Zhi, Y.; Hei, J.; Miao, Y.

doi:10.1107/S160053681202199X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m829

doi:10.1107/S160053681202199X

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Diaquabis(2,2′-bi-1H-imidazole)manganese(II) benzene-1,4-dicarboxylate

Lining Yang,^a ^* Yanxiang Zhi,^b Jiahui Hei ^b and Yanqing Miao ^a

^aDepartment of Pharmacy, Xi'an Medical University, Xi'an, Shaanxi 710021, People's Republic of China, and ^bDepartment of Chemistry, Northwest University, Xi'an, Shaanxi 710069, People's Republic of China
^*Correspondence e-mail: zyfyln828@163.com

(Received 27 April 2012; accepted 15 May 2012; online 26 May 2012)

The asymmetric unit of the title compound, [Mn(C₆H₆N₄)₂(H₂O)₂](C₈H₄O₄), contains one-half each of the centrosymmetric cation and anion. The Mn^II atom is coordinated by four N atoms [Mn—N = 2.2168 (14) and 2.2407 (14) Å] from two 2,2′-biimidazole ligands and two water molecules [Mn—O = 2.2521 (14) Å] in a distorted octahedral geometry. Intermolecular N—H⋯O and O—H⋯O hydrogen bonds consolidate the crystal packing, which also exhibits π–π interactions between five-membered rings, with a centroid–centroid distance of 3.409 (2) Å.

Related literature

For related structures, see: Fortin & Beauchamp (2001 ); Sang et al. (2002 ); Atencio et al. (2004 ); Wang et al. (2007 ). For background to supramolecular assemblies, see: Ramirez et al. (2002 ); Baca et al. (2003 ).

Experimental

Crystal data

[Mn(C₆H₆N₄)₂(H₂O)₂](C₈H₄O₄)
M_r = 523.38
Monoclinic, P 2₁ /n
a = 8.2666 (10) Å
b = 10.9027 (13) Å
c = 12.6734 (16) Å
β = 93.986 (2)°
V = 1139.5 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.63 mm⁻¹
T = 293 K
0.46 × 0.19 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.761, T_max = 0.960
5689 measured reflections
2024 independent reflections
1712 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.075
S = 1.04
2024 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3B⋯O1ⁱ	0.80 (3)	2.09 (3)	2.850 (2)	159 (3)
O3—H3A⋯O2ⁱⁱ	0.87 (3)	1.85 (3)	2.711 (2)	170 (3)
N4—H4⋯O1	0.86	1.87	2.7101 (19)	165
N2—H2A⋯O2	0.86	1.89	2.7482 (19)	173
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681202199X/cv5293sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681202199X/cv5293Isup2.hkl

checkCIF report

Comment top

Supramolecular assemblies have provided numerous materials with very attractive properties (Ramirez et al., 2002). One of the best strategies to construct such materials relies on the use of both the building block approach and the additional hydrogen bonding of the coordinated ligands to their linking capability (Baca et al., 2003). The 2,2'-biimidazole (H₂biim) possesses these properties - coordination to metal centre and acting as a donor in hydrogen bonding interaction (Fortin & Beauchamp, 2001; Sang et al., 2002; Atencio et al., 2004; Wang et al., 2007).

The structure of the title complex consists of [Mn(H₂biim)₂(H₂O)₂]²⁺ cations and terephthalate dianions (Fig. 1). The coordination geometry of the manganese(II) centre can be described as a distorted octahedron including four nitrogen atoms from two chelating H₂biim ligands and two oxygen atoms from aqua ligands. The crystal packing is stabilized by the hydrogen bonds N—H···O and O—H···O (Table 1).

Related literature top

For related structures, see: Fortin & Beauchamp (2001); Sang et al. (2002); Atencio et al. (2004); Wang et al. (2007). For background to supramolecular assemblies, see: Ramirez et al. (2002); Baca et al. (2003).

Experimental top

All reagents were of AR grade from commercial sources and used without further purification. Biimidazole was prepared following the known procedure (Ramirez et al., 2002). Mn(CH₃COO)₂ (0.3 mmol), H₂biim (0.3 mmol) and terephthalic acid (0.3 mmol) in the molar ratio of 1:1:1 were added directly as a solid in 10 ml deionized water respectively, after the mixture was stirred at room temperature for 30 min, the pH value was adjusted to 7.0 by aqueous KOH solution. Then the mixture was placed in a 25 ml Teflon-lined stainless steel vessel and heated at 160°C for 6 days under autogenous pressure. Afterwards, the vessel was cooled to room temperature at a rate of 10°C per hour. Light yellow sheet-like crystals of title complex were obtained and collected by filtration and washed with water (yield 40%).

Computing details top

Data collection: SMART (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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. View of the title complex with the atom-numbering scheme [symmetry codes: (A) -x, -y + 1, -z + 1; (B) -x + 2, -y + 1, -z + 2]. Displacement ellipsoids are drawn at the 30% probability level.

Diaquabis(2,2'-bi-1H-imidazole)manganese(II) benzene-1,4-dicarboxylate top

Crystal data top

[Mn(C₆H₆N₄)₂(H₂O)₂](C₈H₄O₄)	F(000) = 538
M_r = 523.38	D_x = 1.525 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.2666 (10) Å	Cell parameters from 2178 reflections
b = 10.9027 (13) Å	θ = 3.0–26.9°
c = 12.6734 (16) Å	µ = 0.63 mm⁻¹
β = 93.986 (2)°	T = 293 K
V = 1139.5 (2) Å³	Block, yellow
Z = 2	0.46 × 0.19 × 0.07 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2024 independent reflections
Radiation source: fine-focus sealed tube	1712 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −6→9
T_min = 0.761, T_max = 0.960	k = −13→12
5689 measured reflections	l = −14→15

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)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.075	w = 1/[σ²(F_o²) + (0.0403P)² + 0.2933P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2024 reflections	Δρ_max = 0.20 e Å⁻³
167 parameters	Δρ_min = −0.17 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: 0.0048 (12)

Crystal data top

[Mn(C₆H₆N₄)₂(H₂O)₂](C₈H₄O₄)	V = 1139.5 (2) Å³
M_r = 523.38	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.2666 (10) Å	µ = 0.63 mm⁻¹
b = 10.9027 (13) Å	T = 293 K
c = 12.6734 (16) Å	0.46 × 0.19 × 0.07 mm
β = 93.986 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2024 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1712 reflections with I > 2σ(I)
T_min = 0.761, T_max = 0.960	R_int = 0.022
5689 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.20 e Å⁻³
2024 reflections	Δρ_min = −0.17 e Å⁻³
167 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
Mn1	0.0000	0.5000	0.5000	0.02879 (15)
N1	0.24692 (16)	0.58566 (12)	0.51483 (10)	0.0273 (3)
N2	0.48208 (17)	0.58683 (13)	0.60838 (11)	0.0289 (3)
H2A	0.5580	0.5673	0.6552	0.035*
N3	0.12437 (17)	0.39115 (14)	0.62924 (11)	0.0316 (4)
N4	0.34624 (18)	0.37195 (14)	0.73441 (11)	0.0354 (4)
H4	0.4422	0.3851	0.7628	0.042*
O1	0.62726 (17)	0.39434 (14)	0.85633 (11)	0.0517 (4)
O2	0.72528 (16)	0.54524 (15)	0.76328 (11)	0.0501 (4)
O3	0.08176 (19)	0.36279 (14)	0.38200 (11)	0.0431 (4)
C1	0.3431 (2)	0.67589 (16)	0.47712 (14)	0.0322 (4)
H1	0.3136	0.7280	0.4210	0.039*
C2	0.4879 (2)	0.67729 (16)	0.53438 (14)	0.0335 (4)
H2	0.5744	0.7298	0.5250	0.040*
C3	0.3359 (2)	0.53425 (15)	0.59437 (13)	0.0248 (4)
C4	0.2721 (2)	0.43418 (15)	0.65354 (12)	0.0272 (4)
C5	0.2410 (2)	0.28425 (19)	0.76286 (16)	0.0432 (5)
H5	0.2592	0.2268	0.8166	0.052*
C6	0.1051 (2)	0.29636 (18)	0.69827 (15)	0.0403 (5)
H6	0.0128	0.2479	0.7003	0.048*
C7	0.7311 (2)	0.47488 (17)	0.84132 (14)	0.0342 (4)
C8	0.8711 (2)	0.48881 (15)	0.92349 (14)	0.0297 (4)
C9	0.8507 (2)	0.45947 (17)	1.02814 (14)	0.0337 (4)
H9	0.7504	0.4323	1.0476	0.040*
C10	0.9791 (2)	0.47042 (17)	1.10393 (14)	0.0345 (4)
H10	0.9643	0.4502	1.1739	0.041*
H3A	0.135 (3)	0.390 (3)	0.330 (2)	0.080*
H3B	0.104 (3)	0.292 (3)	0.391 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0234 (2)	0.0332 (2)	0.0286 (2)	−0.00110 (16)	−0.00624 (14)	0.00314 (16)
N1	0.0261 (8)	0.0281 (8)	0.0272 (7)	0.0002 (6)	−0.0017 (6)	0.0020 (6)
N2	0.0229 (8)	0.0310 (8)	0.0321 (8)	−0.0009 (6)	−0.0041 (6)	−0.0006 (6)
N3	0.0259 (8)	0.0362 (9)	0.0316 (8)	−0.0039 (7)	−0.0047 (6)	0.0066 (6)
N4	0.0290 (8)	0.0414 (9)	0.0342 (8)	−0.0042 (7)	−0.0085 (6)	0.0097 (7)
O1	0.0465 (9)	0.0514 (9)	0.0536 (9)	−0.0173 (7)	−0.0224 (7)	0.0128 (7)
O2	0.0357 (8)	0.0730 (10)	0.0397 (8)	−0.0108 (7)	−0.0124 (6)	0.0198 (7)
O3	0.0497 (9)	0.0394 (8)	0.0410 (8)	−0.0008 (7)	0.0093 (6)	−0.0038 (7)
C1	0.0342 (10)	0.0297 (10)	0.0327 (9)	0.0005 (8)	0.0015 (8)	0.0055 (8)
C2	0.0306 (10)	0.0300 (10)	0.0404 (10)	−0.0061 (8)	0.0045 (8)	0.0008 (8)
C3	0.0229 (9)	0.0249 (9)	0.0261 (8)	0.0011 (7)	−0.0007 (7)	−0.0022 (7)
C4	0.0260 (9)	0.0291 (9)	0.0261 (9)	0.0005 (7)	−0.0026 (7)	0.0014 (7)
C5	0.0409 (11)	0.0451 (12)	0.0426 (11)	−0.0073 (9)	−0.0056 (9)	0.0216 (9)
C6	0.0327 (10)	0.0434 (12)	0.0439 (11)	−0.0111 (9)	−0.0035 (8)	0.0144 (9)
C7	0.0289 (10)	0.0397 (11)	0.0331 (10)	−0.0006 (8)	−0.0055 (8)	−0.0006 (8)
C8	0.0299 (10)	0.0273 (9)	0.0308 (9)	0.0027 (7)	−0.0066 (7)	−0.0007 (7)
C9	0.0268 (10)	0.0384 (10)	0.0354 (10)	−0.0015 (8)	−0.0021 (7)	0.0008 (8)
C10	0.0354 (11)	0.0398 (11)	0.0274 (9)	−0.0008 (8)	−0.0026 (8)	0.0010 (8)

Geometric parameters (Å, º) top

Mn1—N3	2.2168 (14)	O2—C7	1.250 (2)
Mn1—N3ⁱ	2.2168 (14)	O3—H3A	0.87 (3)
Mn1—N1	2.2407 (14)	O3—H3B	0.80 (3)
Mn1—N1ⁱ	2.2407 (14)	C1—C2	1.356 (2)
Mn1—O3	2.2521 (14)	C1—H1	0.9300
Mn1—O3ⁱ	2.2521 (14)	C2—H2	0.9300
N1—C3	1.330 (2)	C3—C4	1.444 (2)
N1—C1	1.372 (2)	C5—C6	1.350 (3)
N2—C3	1.338 (2)	C5—H5	0.9300
N2—C2	1.364 (2)	C6—H6	0.9300
N2—H2A	0.8600	C7—C8	1.510 (2)
N3—C4	1.324 (2)	C8—C10ⁱⁱ	1.383 (3)
N3—C6	1.370 (2)	C8—C9	1.386 (3)
N4—C4	1.341 (2)	C9—C10	1.386 (2)
N4—C5	1.358 (2)	C9—H9	0.9300
N4—H4	0.8600	C10—C8ⁱⁱ	1.383 (3)
O1—C7	1.252 (2)	C10—H10	0.9300

N3—Mn1—N3ⁱ	180.0	C2—C1—N1	109.46 (15)
N3—Mn1—N1	77.77 (5)	C2—C1—H1	125.3
N3ⁱ—Mn1—N1	102.23 (5)	N1—C1—H1	125.3
N3—Mn1—N1ⁱ	102.23 (5)	C1—C2—N2	106.73 (15)
N3ⁱ—Mn1—N1ⁱ	77.77 (5)	C1—C2—H2	126.6
N1—Mn1—N1ⁱ	180.00 (6)	N2—C2—H2	126.6
N3—Mn1—O3	89.42 (6)	N1—C3—N2	111.53 (15)
N3ⁱ—Mn1—O3	90.58 (6)	N1—C3—C4	120.62 (15)
N1—Mn1—O3	91.08 (5)	N2—C3—C4	127.86 (15)
N1ⁱ—Mn1—O3	88.92 (5)	N3—C4—N4	111.31 (15)
N3—Mn1—O3ⁱ	90.58 (6)	N3—C4—C3	120.73 (15)
N3ⁱ—Mn1—O3ⁱ	89.42 (6)	N4—C4—C3	127.95 (15)
N1—Mn1—O3ⁱ	88.92 (5)	C6—C5—N4	106.95 (16)
N1ⁱ—Mn1—O3ⁱ	91.08 (5)	C6—C5—H5	126.5
O3—Mn1—O3ⁱ	180.00 (5)	N4—C5—H5	126.5
C3—N1—C1	105.24 (14)	C5—C6—N3	109.40 (16)
C3—N1—Mn1	109.91 (11)	C5—C6—H6	125.3
C1—N1—Mn1	144.74 (11)	N3—C6—H6	125.3
C3—N2—C2	107.05 (14)	O2—C7—O1	124.18 (17)
C3—N2—H2A	126.5	O2—C7—C8	118.01 (17)
C2—N2—H2A	126.5	O1—C7—C8	117.81 (16)
C4—N3—C6	105.36 (14)	C10ⁱⁱ—C8—C9	119.03 (16)
C4—N3—Mn1	110.79 (11)	C10ⁱⁱ—C8—C7	121.06 (16)
C6—N3—Mn1	143.79 (12)	C9—C8—C7	119.91 (16)
C4—N4—C5	106.97 (15)	C8—C9—C10	120.33 (17)
C4—N4—H4	126.5	C8—C9—H9	119.8
C5—N4—H4	126.5	C10—C9—H9	119.8
Mn1—O3—H3A	117.7 (18)	C8ⁱⁱ—C10—C9	120.64 (17)
Mn1—O3—H3B	129 (2)	C8ⁱⁱ—C10—H10	119.7
H3A—O3—H3B	108 (3)	C9—C10—H10	119.7

N3—Mn1—N1—C3	−3.35 (11)	C1—N1—C3—C4	179.99 (15)
N3ⁱ—Mn1—N1—C3	176.65 (11)	Mn1—N1—C3—C4	2.77 (19)
N1ⁱ—Mn1—N1—C3	118.74 (12)	C2—N2—C3—N1	0.25 (19)
O3—Mn1—N1—C3	−92.52 (11)	C2—N2—C3—C4	−179.90 (17)
O3ⁱ—Mn1—N1—C3	87.48 (11)	C6—N3—C4—N4	−0.3 (2)
N3—Mn1—N1—C1	−178.7 (2)	Mn1—N3—C4—N4	177.63 (11)
N3ⁱ—Mn1—N1—C1	1.3 (2)	C6—N3—C4—C3	178.54 (16)
N1ⁱ—Mn1—N1—C1	−56.59 (18)	Mn1—N3—C4—C3	−3.5 (2)
O3—Mn1—N1—C1	92.1 (2)	C5—N4—C4—N3	0.4 (2)
O3ⁱ—Mn1—N1—C1	−87.9 (2)	C5—N4—C4—C3	−178.38 (18)
N3ⁱ—Mn1—N3—C4	−180 (81)	N1—C3—C4—N3	0.5 (3)
N1—Mn1—N3—C4	3.61 (11)	N2—C3—C4—N3	−179.33 (16)
N1ⁱ—Mn1—N3—C4	−176.39 (11)	N1—C3—C4—N4	179.15 (16)
O3—Mn1—N3—C4	94.84 (12)	N2—C3—C4—N4	−0.7 (3)
O3ⁱ—Mn1—N3—C4	−85.16 (12)	C4—N4—C5—C6	−0.3 (2)
N3ⁱ—Mn1—N3—C6	−3 (81)	N4—C5—C6—N3	0.1 (2)
N1—Mn1—N3—C6	−179.8 (2)	C4—N3—C6—C5	0.1 (2)
N1ⁱ—Mn1—N3—C6	0.2 (2)	Mn1—N3—C6—C5	−176.60 (16)
O3—Mn1—N3—C6	−88.5 (2)	O2—C7—C8—C10ⁱⁱ	−30.4 (3)
O3ⁱ—Mn1—N3—C6	91.5 (2)	O1—C7—C8—C10ⁱⁱ	150.38 (18)
C3—N1—C1—C2	0.00 (19)	O2—C7—C8—C9	150.21 (18)
Mn1—N1—C1—C2	175.45 (14)	O1—C7—C8—C9	−29.0 (3)
N1—C1—C2—N2	0.1 (2)	C10ⁱⁱ—C8—C9—C10	−0.3 (3)
C3—N2—C2—C1	−0.24 (19)	C7—C8—C9—C10	179.15 (17)
C1—N1—C3—N2	−0.15 (18)	C8—C9—C10—C8ⁱⁱ	0.3 (3)
Mn1—N1—C3—N2	−177.37 (11)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O1ⁱⁱⁱ	0.80 (3)	2.09 (3)	2.850 (2)	159 (3)
O3—H3A···O2^iv	0.87 (3)	1.85 (3)	2.711 (2)	170 (3)
N4—H4···O1	0.86	1.87	2.7101 (19)	165
N2—H2A···O2	0.86	1.89	2.7482 (19)	173

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

Experimental details

Crystal data
Chemical formula	[Mn(C₆H₆N₄)₂(H₂O)₂](C₈H₄O₄)
M_r	523.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.2666 (10), 10.9027 (13), 12.6734 (16)
β (°)	93.986 (2)
V (Å³)	1139.5 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.46 × 0.19 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.761, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	5689, 2024, 1712
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.075, 1.04
No. of reflections	2024
No. of parameters	167
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.17

Computer programs: SMART (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
O3—H3B···O1ⁱ	0.80 (3)	2.09 (3)	2.850 (2)	159 (3)
O3—H3A···O2ⁱⁱ	0.87 (3)	1.85 (3)	2.711 (2)	170 (3)
N4—H4···O1	0.86	1.87	2.7101 (19)	164.5
N2—H2A···O2	0.86	1.89	2.7482 (19)	172.8

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

References

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Volume 68| Part 6| June 2012| Page m829

doi:10.1107/S160053681202199X

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