Bis(1H-benzimidazole-2-carboxyl-ato-κ(2)N(3),O)bis-(ethanol-κO)manganese(II).

In the title compound, [Mn(C(8)H(5)N(2)O(2))(2)(C(2)H(5)OH)(2)], the Mn(II) atom is six-coordinated by two N and two O atoms from two 1H-benzimidazole-2-carboxyl-ate (L) ligands and by two O atoms from two ethanol mol-ecules in a distorted octa-hedral geometry. The mean planes of the two L ligands are inclined to each other at 7.6 (1)°. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the ab plane.

Related literature

For related structures, see: Carballo et al. (1996 ▶); Di et al. (2010 ▶); Fan et al. (2011 ▶); Małecki & Maroń (2012 ▶); Rettig et al. (1999 ▶); Saczewski et al. (2006 ▶); Zheng et al. (2011 ▶).

Experimental

Crystal data

[Mn(C8H5N2O2)2(C2H6O)2]

M = 469.36

Triclinic,

a = 5.4176 (12) Å

b = 10.358 (2) Å

c = 19.853 (5) Å

α = 75.671 (3)°

β = 88.294 (3)°

γ = 78.230 (3)°

V = 1056.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.67 mm−1

T = 298 K

0.32 × 0.25 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.814, T max = 0.867

5431 measured reflections

3751 independent reflections

2664 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.131

S = 1.06

3751 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.37 e Å−3

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: ORTEPIII (Burnett & Johnson, 1996 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812039475/cv5342sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039475/cv5342Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Mn(C8H5N2O2)2(C2H6O)2]	Z = 2
Mr = 469.36	F(000) = 486
Triclinic, P1	Dx = 1.476 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.4176 (12) Å	Cell parameters from 1379 reflections
b = 10.358 (2) Å	θ = 2.6–26.0°
c = 19.853 (5) Å	µ = 0.67 mm−1
α = 75.671 (3)°	T = 298 K
β = 88.294 (3)°	Block, pink
γ = 78.230 (3)°	0.32 × 0.25 × 0.22 mm
V = 1056.4 (4) Å3

Bruker APEXII CCD diffractometer	3751 independent reflections
Radiation source: fine-focus sealed tube	2664 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 25.3°, θmin = 2.1°
Absorption correction: multi-scan (APEX2; Bruker, 2004)	h = −6→6
Tmin = 0.814, Tmax = 0.867	k = −12→12
5431 measured reflections	l = −23→19

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0642P)2 + 0.1644P] where P = (Fo2 + 2Fc2)/3
3751 reflections	(Δ/σ)max < 0.001
282 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

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.

	x	y	z	Uiso*/Ueq
Mn1	0.46488 (9)	0.05915 (4)	0.74701 (2)	0.03348 (18)
O1	0.8162 (4)	−0.08678 (19)	0.78515 (11)	0.0369 (5)
O6	0.2473 (4)	−0.0469 (2)	0.83306 (11)	0.0422 (6)
H6A	0.0932	−0.0433	0.8233	0.051*
O5	0.6780 (4)	0.1657 (2)	0.66112 (11)	0.0461 (6)
H5A	0.8299	0.1625	0.6730	0.055*
O3	0.1113 (4)	0.2050 (2)	0.71013 (11)	0.0368 (5)
O2	1.0056 (4)	−0.3035 (2)	0.79681 (12)	0.0481 (6)
O4	−0.0995 (4)	0.4137 (2)	0.70807 (12)	0.0476 (6)
N4	0.2721 (5)	0.4332 (2)	0.80378 (14)	0.0402 (7)
H4	0.1633	0.5087	0.7945	0.048*
N1	0.4569 (5)	−0.1113 (2)	0.69784 (13)	0.0333 (6)
N3	0.4673 (5)	0.2256 (2)	0.79975 (13)	0.0334 (6)
N2	0.6283 (5)	−0.3281 (2)	0.70541 (13)	0.0376 (7)
H2	0.7302	−0.4056	0.7181	0.045*
C3	0.3176 (6)	−0.1605 (3)	0.65648 (15)	0.0329 (7)
C9	0.0768 (6)	0.3172 (3)	0.72763 (16)	0.0331 (7)
C8	0.4246 (6)	−0.2976 (3)	0.66079 (16)	0.0355 (8)
C16	0.4743 (6)	0.4005 (3)	0.84869 (17)	0.0380 (8)
C2	0.6400 (6)	−0.2151 (3)	0.72576 (16)	0.0322 (7)
C12	0.8195 (7)	0.2074 (3)	0.88379 (17)	0.0438 (8)
H12	0.9051	0.1210	0.8818	0.053*
C7	0.3212 (7)	−0.3756 (3)	0.62573 (18)	0.0473 (9)
H7	0.3924	−0.4668	0.6295	0.057*
C15	0.5634 (8)	0.4703 (4)	0.89100 (19)	0.0552 (10)
H15	0.4793	0.5567	0.8934	0.066*
C10	0.2738 (6)	0.3254 (3)	0.77646 (16)	0.0337 (7)
C11	0.5984 (6)	0.2698 (3)	0.84512 (16)	0.0327 (7)
C4	0.1007 (7)	−0.0984 (3)	0.61532 (18)	0.0456 (9)
H4A	0.0262	−0.0077	0.6119	0.055*
C5	0.0011 (7)	−0.1746 (4)	0.58016 (18)	0.0505 (9)
H5	−0.1421	−0.1344	0.5521	0.061*
C1	0.8394 (6)	−0.2038 (3)	0.77318 (16)	0.0342 (7)
C6	0.1096 (8)	−0.3117 (4)	0.58541 (19)	0.0544 (10)
H6	0.0361	−0.3605	0.5609	0.065*
C13	0.9074 (7)	0.2778 (4)	0.92515 (19)	0.0548 (10)
H13	1.0557	0.2384	0.9511	0.066*
C14	0.7791 (8)	0.4069 (4)	0.9290 (2)	0.0627 (12)
H14	0.8422	0.4509	0.9581	0.075*
C17	0.6190 (9)	0.2498 (4)	0.5940 (2)	0.0713 (12)
H17A	0.5509	0.3418	0.5977	0.086*
H17B	0.7733	0.2512	0.5680	0.086*
C19	0.3144 (9)	−0.1405 (5)	0.8966 (2)	0.0818 (15)
H19A	0.1628	−0.1460	0.9235	0.098*
H19B	0.3765	−0.2291	0.8875	0.098*
C18	0.4453 (11)	0.2095 (7)	0.5564 (2)	0.124 (2)
H18A	0.2976	0.1994	0.5835	0.187*
H18B	0.5205	0.1242	0.5463	0.187*
H18C	0.3990	0.2773	0.5137	0.187*
C20	0.4932 (11)	−0.1153 (7)	0.9374 (2)	0.123 (2)
H20A	0.5437	−0.1930	0.9757	0.185*
H20B	0.4227	−0.0373	0.9547	0.185*
H20C	0.6374	−0.0982	0.9099	0.185*

	U11	U22	U33	U12	U13	U23
Mn1	0.0294 (3)	0.0244 (3)	0.0481 (3)	0.00030 (19)	−0.0057 (2)	−0.0157 (2)
O1	0.0298 (13)	0.0262 (11)	0.0574 (14)	0.0004 (9)	−0.0091 (10)	−0.0188 (10)
O6	0.0336 (13)	0.0479 (13)	0.0476 (14)	−0.0115 (11)	−0.0036 (10)	−0.0131 (11)
O5	0.0371 (14)	0.0578 (15)	0.0456 (14)	−0.0137 (11)	−0.0057 (11)	−0.0127 (12)
O3	0.0317 (13)	0.0281 (11)	0.0536 (14)	−0.0012 (9)	−0.0084 (10)	−0.0181 (10)
O2	0.0421 (15)	0.0307 (12)	0.0695 (16)	0.0061 (11)	−0.0190 (12)	−0.0174 (11)
O4	0.0412 (15)	0.0268 (12)	0.0727 (17)	0.0047 (11)	−0.0160 (12)	−0.0157 (11)
N4	0.0433 (18)	0.0220 (13)	0.0554 (17)	0.0011 (12)	−0.0068 (14)	−0.0150 (12)
N1	0.0303 (16)	0.0270 (13)	0.0434 (15)	0.0008 (11)	−0.0032 (12)	−0.0150 (12)
N3	0.0307 (15)	0.0263 (13)	0.0433 (15)	−0.0005 (11)	−0.0031 (12)	−0.0126 (11)
N2	0.0399 (17)	0.0221 (13)	0.0530 (17)	−0.0018 (12)	−0.0056 (13)	−0.0162 (12)
C3	0.0326 (19)	0.0312 (16)	0.0380 (18)	−0.0054 (14)	−0.0002 (14)	−0.0149 (14)
C9	0.0323 (19)	0.0228 (15)	0.0436 (18)	−0.0016 (14)	0.0002 (14)	−0.0104 (14)
C8	0.0336 (19)	0.0331 (17)	0.0435 (19)	−0.0053 (14)	−0.0004 (15)	−0.0174 (14)
C16	0.040 (2)	0.0300 (17)	0.0450 (19)	−0.0051 (15)	−0.0039 (16)	−0.0119 (15)
C2	0.0335 (19)	0.0209 (15)	0.0425 (18)	−0.0014 (13)	−0.0013 (14)	−0.0110 (13)
C12	0.038 (2)	0.0433 (19)	0.049 (2)	−0.0049 (16)	−0.0007 (16)	−0.0127 (16)
C7	0.055 (3)	0.0373 (19)	0.056 (2)	−0.0115 (17)	0.0024 (19)	−0.0234 (17)
C15	0.064 (3)	0.042 (2)	0.069 (3)	−0.0064 (19)	−0.010 (2)	−0.0322 (19)
C10	0.0329 (19)	0.0226 (15)	0.0449 (19)	−0.0029 (13)	0.0014 (14)	−0.0096 (13)
C11	0.0350 (19)	0.0278 (16)	0.0371 (17)	−0.0052 (14)	−0.0031 (14)	−0.0122 (13)
C4	0.039 (2)	0.0414 (19)	0.057 (2)	0.0008 (16)	−0.0056 (17)	−0.0199 (17)
C5	0.042 (2)	0.059 (2)	0.053 (2)	−0.0095 (18)	−0.0128 (18)	−0.0189 (19)
C1	0.0315 (19)	0.0249 (16)	0.0449 (19)	0.0005 (14)	−0.0025 (15)	−0.0110 (14)
C6	0.060 (3)	0.059 (2)	0.056 (2)	−0.023 (2)	−0.006 (2)	−0.026 (2)
C13	0.046 (2)	0.067 (3)	0.056 (2)	−0.014 (2)	−0.0121 (18)	−0.020 (2)
C14	0.071 (3)	0.062 (3)	0.067 (3)	−0.018 (2)	−0.017 (2)	−0.031 (2)
C17	0.074 (3)	0.069 (3)	0.062 (3)	−0.014 (2)	−0.018 (2)	0.002 (2)
C19	0.079 (3)	0.070 (3)	0.081 (3)	−0.028 (3)	−0.036 (3)	0.022 (2)
C18	0.105 (5)	0.218 (7)	0.059 (3)	−0.087 (5)	−0.022 (3)	−0.004 (4)
C20	0.111 (5)	0.208 (7)	0.058 (3)	−0.090 (5)	−0.027 (3)	0.005 (4)

Mn1—O1	2.197 (2)	C16—C11	1.402 (4)
Mn1—O3	2.201 (2)	C2—C1	1.494 (4)
Mn1—O5	2.220 (2)	C12—C13	1.376 (5)
Mn1—N1	2.227 (2)	C12—C11	1.391 (4)
Mn1—N3	2.230 (2)	C12—H12	0.9300
Mn1—O6	2.235 (2)	C7—C6	1.369 (5)
O1—C1	1.273 (3)	C7—H7	0.9300
O6—C19	1.393 (4)	C15—C14	1.363 (5)
O6—H6A	0.8535	C15—H15	0.9300
O5—C17	1.405 (4)	C4—C5	1.368 (5)
O5—H5A	0.8546	C4—H4A	0.9300
O3—C9	1.271 (3)	C5—C6	1.401 (5)
O2—C1	1.226 (3)	C5—H5	0.9300
O4—C9	1.226 (3)	C6—H6	0.9300
N4—C10	1.355 (4)	C13—C14	1.395 (5)
N4—C16	1.366 (4)	C13—H13	0.9300
N4—H4	0.8600	C14—H14	0.9300
N1—C2	1.323 (4)	C17—C18	1.404 (6)
N1—C3	1.380 (4)	C17—H17A	0.9700
N3—C10	1.316 (4)	C17—H17B	0.9700
N3—C11	1.378 (4)	C19—C20	1.384 (6)
N2—C2	1.343 (4)	C19—H19A	0.9700
N2—C8	1.371 (4)	C19—H19B	0.9700
N2—H2	0.8600	C18—H18A	0.9600
C3—C4	1.397 (4)	C18—H18B	0.9600
C3—C8	1.403 (4)	C18—H18C	0.9600
C9—C10	1.492 (4)	C20—H20A	0.9600
C8—C7	1.392 (5)	C20—H20B	0.9600
C16—C15	1.388 (4)	C20—H20C	0.9600
O1—Mn1—O3	179.29 (8)	C6—C7—H7	121.6
O1—Mn1—O5	89.01 (8)	C8—C7—H7	121.6
O3—Mn1—O5	91.60 (8)	C14—C15—C16	117.3 (3)
O1—Mn1—N1	76.37 (8)	C14—C15—H15	121.3
O3—Mn1—N1	103.94 (8)	C16—C15—H15	121.3
O5—Mn1—N1	93.63 (9)	N3—C10—N4	112.0 (3)
O1—Mn1—N3	103.36 (8)	N3—C10—C9	123.3 (3)
O3—Mn1—N3	76.30 (8)	N4—C10—C9	124.7 (3)
O5—Mn1—N3	88.43 (9)	N3—C11—C12	131.0 (3)
N1—Mn1—N3	177.92 (9)	N3—C11—C16	109.1 (3)
O1—Mn1—O6	91.49 (8)	C12—C11—C16	119.9 (3)
O3—Mn1—O6	87.90 (8)	C5—C4—C3	118.1 (3)
O5—Mn1—O6	179.50 (8)	C5—C4—H4A	120.9
N1—Mn1—O6	86.45 (9)	C3—C4—H4A	120.9
N3—Mn1—O6	91.50 (9)	C4—C5—C6	121.6 (3)
C1—O1—Mn1	116.15 (19)	C4—C5—H5	119.2
C19—O6—Mn1	134.0 (3)	C6—C5—H5	119.2
C19—O6—H6A	109.2	O2—C1—O1	126.1 (3)
Mn1—O6—H6A	115.6	O2—C1—C2	119.4 (3)
C17—O5—Mn1	135.8 (2)	O1—C1—C2	114.5 (2)
C17—O5—H5A	111.0	C7—C6—C5	121.6 (3)
Mn1—O5—H5A	112.8	C7—C6—H6	119.2
C9—O3—Mn1	116.57 (19)	C5—C6—H6	119.2
C10—N4—C16	107.7 (3)	C12—C13—C14	121.5 (4)
C10—N4—H4	126.1	C12—C13—H13	119.3
C16—N4—H4	126.1	C14—C13—H13	119.3
C2—N1—C3	105.3 (2)	C15—C14—C13	121.6 (4)
C2—N1—Mn1	108.91 (19)	C15—C14—H14	119.2
C3—N1—Mn1	144.9 (2)	C13—C14—H14	119.2
C10—N3—C11	105.9 (2)	C18—C17—O5	114.3 (4)
C10—N3—Mn1	109.0 (2)	C18—C17—H17A	108.7
C11—N3—Mn1	145.0 (2)	O5—C17—H17A	108.7
C2—N2—C8	107.6 (2)	C18—C17—H17B	108.7
C2—N2—H2	126.2	O5—C17—H17B	108.7
C8—N2—H2	126.2	H17A—C17—H17B	107.6
N1—C3—C4	131.3 (3)	C20—C19—O6	117.2 (4)
N1—C3—C8	109.2 (3)	C20—C19—H19A	108.0
C4—C3—C8	119.5 (3)	O6—C19—H19A	108.0
O4—C9—O3	125.6 (3)	C20—C19—H19B	108.0
O4—C9—C10	120.1 (3)	O6—C19—H19B	108.0
O3—C9—C10	114.3 (3)	H19A—C19—H19B	107.2
N2—C8—C7	132.4 (3)	C17—C18—H18A	109.5
N2—C8—C3	105.3 (3)	C17—C18—H18B	109.5
C7—C8—C3	122.3 (3)	H18A—C18—H18B	109.5
N4—C16—C15	132.9 (3)	C17—C18—H18C	109.5
N4—C16—C11	105.3 (3)	H18A—C18—H18C	109.5
C15—C16—C11	121.8 (3)	H18B—C18—H18C	109.5
N1—C2—N2	112.6 (3)	C19—C20—H20A	109.5
N1—C2—C1	122.6 (2)	C19—C20—H20B	109.5
N2—C2—C1	124.8 (3)	H20A—C20—H20B	109.5
C13—C12—C11	117.8 (3)	C19—C20—H20C	109.5
C13—C12—H12	121.1	H20A—C20—H20C	109.5
C11—C12—H12	121.1	H20B—C20—H20C	109.5
C6—C7—C8	116.9 (3)
O5—Mn1—O1—C1	−104.5 (2)	C3—N1—C2—N2	−0.1 (4)
N1—Mn1—O1—C1	−10.5 (2)	Mn1—N1—C2—N2	172.0 (2)
N3—Mn1—O1—C1	167.4 (2)	C3—N1—C2—C1	178.4 (3)
O6—Mn1—O1—C1	75.5 (2)	Mn1—N1—C2—C1	−9.5 (4)
O1—Mn1—O6—C19	16.9 (3)	C8—N2—C2—N1	0.2 (4)
O3—Mn1—O6—C19	−162.8 (3)	C8—N2—C2—C1	−178.3 (3)
N1—Mn1—O6—C19	93.1 (3)	N2—C8—C7—C6	178.8 (4)
N3—Mn1—O6—C19	−86.5 (3)	C3—C8—C7—C6	0.9 (5)
O1—Mn1—O5—C17	155.4 (3)	N4—C16—C15—C14	−178.6 (4)
O3—Mn1—O5—C17	−24.9 (3)	C11—C16—C15—C14	0.5 (6)
N1—Mn1—O5—C17	79.1 (3)	C11—N3—C10—N4	0.5 (4)
N3—Mn1—O5—C17	−101.2 (3)	Mn1—N3—C10—N4	−176.7 (2)
O5—Mn1—O3—C9	−81.6 (2)	C11—N3—C10—C9	−177.6 (3)
N1—Mn1—O3—C9	−175.8 (2)	Mn1—N3—C10—C9	5.3 (4)
N3—Mn1—O3—C9	6.4 (2)	C16—N4—C10—N3	−1.2 (4)
O6—Mn1—O3—C9	98.4 (2)	C16—N4—C10—C9	176.8 (3)
O1—Mn1—N1—C2	9.8 (2)	O4—C9—C10—N3	179.7 (3)
O3—Mn1—N1—C2	−169.5 (2)	O3—C9—C10—N3	0.0 (5)
O5—Mn1—N1—C2	97.9 (2)	O4—C9—C10—N4	1.9 (5)
O6—Mn1—N1—C2	−82.6 (2)	O3—C9—C10—N4	−177.9 (3)
O1—Mn1—N1—C3	176.6 (4)	C10—N3—C11—C12	−178.8 (3)
O3—Mn1—N1—C3	−2.8 (4)	Mn1—N3—C11—C12	−3.6 (6)
O5—Mn1—N1—C3	−95.3 (4)	C10—N3—C11—C16	0.5 (4)
O6—Mn1—N1—C3	84.2 (4)	Mn1—N3—C11—C16	175.7 (3)
O1—Mn1—N3—C10	175.0 (2)	C13—C12—C11—N3	179.8 (3)
O3—Mn1—N3—C10	−5.7 (2)	C13—C12—C11—C16	0.5 (5)
O5—Mn1—N3—C10	86.4 (2)	N4—C16—C11—N3	−1.2 (4)
O6—Mn1—N3—C10	−93.2 (2)	C15—C16—C11—N3	179.5 (3)
O1—Mn1—N3—C11	−0.2 (4)	N4—C16—C11—C12	178.2 (3)
O3—Mn1—N3—C11	179.1 (4)	C15—C16—C11—C12	−1.1 (5)
O5—Mn1—N3—C11	−88.8 (4)	N1—C3—C4—C5	−179.1 (3)
O6—Mn1—N3—C11	91.7 (4)	C8—C3—C4—C5	−0.4 (5)
C2—N1—C3—C4	178.9 (3)	C3—C4—C5—C6	0.8 (6)
Mn1—N1—C3—C4	11.9 (6)	Mn1—O1—C1—O2	−171.0 (3)
C2—N1—C3—C8	0.0 (3)	Mn1—O1—C1—C2	8.8 (3)
Mn1—N1—C3—C8	−167.0 (3)	N1—C2—C1—O2	−179.3 (3)
Mn1—O3—C9—O4	174.7 (3)	N2—C2—C1—O2	−0.9 (5)
Mn1—O3—C9—C10	−5.6 (3)	N1—C2—C1—O1	0.9 (4)
C2—N2—C8—C7	−178.4 (4)	N2—C2—C1—O1	179.3 (3)
C2—N2—C8—C3	−0.2 (4)	C8—C7—C6—C5	−0.5 (6)
N1—C3—C8—N2	0.1 (4)	C4—C5—C6—C7	−0.3 (6)
C4—C3—C8—N2	−178.9 (3)	C11—C12—C13—C14	0.5 (6)
N1—C3—C8—C7	178.5 (3)	C16—C15—C14—C13	0.6 (6)
C4—C3—C8—C7	−0.5 (5)	C12—C13—C14—C15	−1.2 (6)
C10—N4—C16—C15	−179.4 (4)	Mn1—O5—C17—C18	−40.2 (6)
C10—N4—C16—C11	1.5 (4)	Mn1—O6—C19—C20	45.1 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4i	0.86	1.96	2.766 (3)	155
N4—H4···O2ii	0.86	1.97	2.786 (3)	158
O5—H5A···O3iii	0.85	1.89	2.710 (3)	161
O6—H6A···O1iv	0.85	1.88	2.692 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4i	0.86	1.96	2.766 (3)	155
N4—H4⋯O2ii	0.86	1.97	2.786 (3)	158
O5—H5A⋯O3iii	0.85	1.89	2.710 (3)	161
O6—H6A⋯O1iv	0.85	1.88	2.692 (3)	158

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .