Bis(2-amino-4-methyl­pyrimidin-1-ium) hexa­aqua­cobalt(II) disulfate dihydrate

Mirzaei, M.; Eshtiagh-Hosseini, H.; Zarghami, S.; Karrabi, Z.; Saeedi, M.; Mague, J.T.

doi:10.1107/S1600536813002146

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page m128

doi:10.1107/S1600536813002146

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Bis(2-amino-4-methylpyrimidin-1-ium) hexaaquacobalt(II) disulfate dihydrate

M. Mirzaei,^a ^* H. Eshtiagh-Hosseini,^a S. Zarghami,^a Z. Karrabi,^a M. Saeedi ^a and J. T. Mague ^b ^*

^aDepartment of Chemistry, Ferdowsi University of Mashhad, 917751436 Mashhad, Iran, and ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: , joelt@tulane.edu

(Received 20 January 2013; accepted 22 January 2013; online 31 January 2013)

In the title hydrated mixed-cation salt, (C₅H₈N₃)₂[Co(H₂O)₆](SO₄)₂·2H₂O, the complete octahedral hexaaqua complex cation is generated by crystallographic inversion symmetry. In the crystal, the components are linked by O—H⋯O and N—H⋯O hydrogen bonds, the latter, involving pyrimidinium cations and sulfate anions, generating R₂²(8) loops. These, together with π–π interactions between centrosymmetrically related pyrimidinium cations [centroid–centroid separation = 3.5460 (8) Å], lead to the formation of a three-dimensional network.

Related literature

For a report of the structure of the [Co(H₂O)₆]²⁺ ion, see: Shiu et al. (2004 ).

Experimental

Crystal data

(C₅H₈N₃)₂[Co(H₂O)₆](SO₄)₂·2H₂O
M_r = 615.49
Triclinic, $[P \overline 1]$
a = 6.4116 (6) Å
b = 7.7751 (7) Å
c = 13.0423 (12) Å
α = 80.136 (1)°
β = 80.413 (1)°
γ = 73.231 (1)°
V = 608.57 (10) Å³
Z = 1
Mo Kα radiation
μ = 0.96 mm⁻¹
T = 100 K
0.19 × 0.19 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2009 ) T_min = 0.780, T_max = 0.893
10780 measured reflections
3085 independent reflections
2944 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.073
S = 1.09
3085 reflections
161 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—O1	2.0838 (9)
Co1—O2	2.0643 (9)
Co1—O3	2.1140 (10)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O8	0.84	1.92	2.7562 (14)	171
O1—H1B⋯O4	0.84	1.97	2.8050 (13)	178
O2—H2A⋯O4ⁱ	0.84	1.92	2.7533 (14)	173
O2—H2B⋯O5	0.84	1.87	2.7077 (13)	174
O3—H3C⋯O8ⁱ	0.84	1.92	2.7508 (13)	170
O3—H3D⋯O7ⁱⁱ	0.84	1.95	2.7865 (14)	177
N2—H2N⋯O6ⁱⁱⁱ	0.91	1.81	2.7155 (15)	172
N3—H3A⋯O5ⁱⁱⁱ	0.91	1.87	2.7776 (15)	175
N3—H3B⋯O6^iv	0.91	1.98	2.8775 (15)	168
O8—H8A⋯O7ⁱⁱ	0.84	1.98	2.7684 (14)	156
O8—H8B⋯O7^v	0.84	2.02	2.8582 (14)	172
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) -x+2, -y, -z+1; (iv) -x+1, -y, -z+1; (v) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2009 ); data reduction: SAINT; program(s) used to solve structure: SHELXM (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813002146/hb7029sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813002146/hb7029Isup2.hkl

checkCIF report

Comment top

In an attempt to synthesize a cobalt complex of quinoxaline-2,3-dicarboxylic acid by conventional proton transfer processes, cobalt(II) sulfate hexahydrate and the acid were reacted with 2-amino-4-methylpyrimidine. The crystalline product obtained proved to be [Co(H₂O)₆][2a-4m-pym]₂(SO₄)₂.2H₂O (2a-4m-pym = 2-amino-4-methylpyrimidinium) with the cobalt cation having crystallographiclly imposed centrosymmetry (Fig. 1). The Co—O distances range from 2.0643 (9) to 2.1140 (10) A° while the O—Co—O angles range from 90.69 (4) to 93.59 (4)° leading to a somewhat distorted octahedral coordination geometry. The [Co(H₂O)₆]²⁺ cations and uncoordinated water molecules form sheets parallel to [110] which are capped on both sides by sulfate ions and held together by O—H···O hydrogen bonds (Fig. 2). N—H···O interactions bind the pyrimidinium cations to the sulfate ions (Fig. 3) with the cations from adjacent sheets intercalating one another (Fig. 2) and stabilized by pairwise π···π (3.546 A°) interactions between them (center pair of cations in Fig. 2). The N2—H2n···O6 and N3—H3a···O5 hydrogen bonding interactions generate R₂²(8) synthons.

Related literature top

For a report of the structure of the [Co(H₂O)₆]²⁺ ion, see: Shiu et al. (2004).

Experimental top

An aqueous solution of cobalt(II) sulfate hexahydrate (0.4 mmol, 0.8 mg) in distilled water (5 ml) was added to an aqueous solution of quinoxaline-2,3-dicarboxylic acid (0.11 mmol, 25 mg) and 2-amino-4-methyl pyrimidine (0.24 mmol, 26 mg). The mixture refluxed for 5 hrs at 75°C. Orange blocks were obtained by slow evaporation of the reaction mixture at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXM (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Perspective view of the title compound with 50% probability ellipsoids.
	Fig. 2. Packing of the title compound viewed down a. Hydrogen bonds are indicated by dotted lines.
	Fig. 3. N—H···O hydrogen bonds and the R₂²(8) synthons (N2, N3, O5 O6).

Bis(2-amino-4-methylpyrimidin-1-ium) hexaaquacobalt(II) disulfate dihydrate top

Crystal data top

(C₅H₈N₃)₂[Co(H₂O)₆](SO₄)₂·2H₂O	Z = 1
M_r = 615.49	F(000) = 321
Triclinic, P1	D_x = 1.679 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4116 (6) Å	Cell parameters from 8977 reflections
b = 7.7751 (7) Å	θ = 2.8–29.2°
c = 13.0423 (12) Å	µ = 0.96 mm⁻¹
α = 80.136 (1)°	T = 100 K
β = 80.413 (1)°	Block, orange
γ = 73.231 (1)°	0.19 × 0.19 × 0.12 mm
V = 608.57 (10) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	3085 independent reflections
Radiation source: fine-focus sealed tube	2944 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 29.2°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2009)	h = −8→8
T_min = 0.780, T_max = 0.893	k = −10→10
10780 measured reflections	l = −17→17

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0386P)² + 0.2936P] where P = (F_o² + 2F_c²)/3
3085 reflections	(Δ/σ)_max = 0.001
161 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

(C₅H₈N₃)₂[Co(H₂O)₆](SO₄)₂·2H₂O	γ = 73.231 (1)°
M_r = 615.49	V = 608.57 (10) Å³
Triclinic, P1	Z = 1
a = 6.4116 (6) Å	Mo Kα radiation
b = 7.7751 (7) Å	µ = 0.96 mm⁻¹
c = 13.0423 (12) Å	T = 100 K
α = 80.136 (1)°	0.19 × 0.19 × 0.12 mm
β = 80.413 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	3085 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2009)	2944 reflections with I > 2σ(I)
T_min = 0.780, T_max = 0.893	R_int = 0.025
10780 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 1.09	Δρ_max = 0.59 e Å⁻³
3085 reflections	Δρ_min = −0.40 e Å⁻³
161 parameters

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5 °. in omega, collected at phi = 0.00, 90.00 and 180.00 °. and 2 sets of 800 frames, each of width 0.45 ° in phi, collected at omega = -30.00 and 210.00 °. The scan time was 10 sec/frame.

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å) while those attached to nitrogen and oxygen were placed in locations derived from a difference map. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Co1	1.0000	0.5000	0.0000	0.00955 (8)
O1	0.68016 (15)	0.50215 (13)	0.06589 (8)	0.01452 (19)
H1A	0.5761	0.5965	0.0592	0.017*
H1B	0.6253	0.4255	0.1061	0.017*
O2	1.13866 (16)	0.27066 (13)	0.09714 (8)	0.0152 (2)
H2A	1.2384	0.2644	0.1331	0.018*
H2B	1.0513	0.2134	0.1317	0.018*
O3	1.01700 (15)	0.67088 (13)	0.10641 (8)	0.01429 (19)
H3C	1.1304	0.7080	0.0967	0.017*
H3D	0.9025	0.7538	0.1193	0.017*
N1	0.77618 (19)	0.29129 (15)	0.48276 (9)	0.0141 (2)
N2	1.13318 (19)	0.19273 (15)	0.53464 (9)	0.0136 (2)
H2N	1.2214	0.1283	0.5837	0.016*
N3	0.8459 (2)	0.09569 (16)	0.63508 (9)	0.0169 (2)
H3A	0.9370	0.0291	0.6825	0.020*
H3B	0.7047	0.0884	0.6443	0.020*
C1	0.9176 (2)	0.19330 (17)	0.55062 (10)	0.0126 (2)
C2	1.2141 (2)	0.28771 (18)	0.44771 (11)	0.0159 (3)
H2	1.3655	0.2840	0.4361	0.019*
C3	1.0775 (2)	0.38846 (18)	0.37710 (11)	0.0164 (3)
H3	1.1307	0.4555	0.3155	0.020*
C4	0.8539 (2)	0.38965 (18)	0.39882 (10)	0.0143 (2)
C5	0.6904 (2)	0.50542 (19)	0.32901 (11)	0.0184 (3)
H5A	0.6319	0.4281	0.2960	0.028*
H5B	0.7619	0.5807	0.2746	0.028*
H5C	0.5701	0.5834	0.3706	0.028*
S1	0.64309 (5)	0.07057 (4)	0.22320 (2)	0.00995 (8)
O4	0.48922 (15)	0.25043 (12)	0.19945 (8)	0.01356 (19)
O5	0.86583 (15)	0.09036 (13)	0.22097 (8)	0.0153 (2)
O6	0.57348 (16)	−0.01584 (13)	0.32903 (8)	0.0148 (2)
O7	0.64425 (16)	−0.04477 (13)	0.14342 (8)	0.0164 (2)
O8	0.36083 (16)	0.82758 (13)	0.05699 (8)	0.01547 (19)
H8A	0.4119	0.8803	0.0939	0.019*
H8B	0.3513	0.8994	0.0009	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.00874 (12)	0.00915 (12)	0.01048 (13)	−0.00265 (8)	−0.00139 (9)	0.00014 (8)
O1	0.0100 (4)	0.0120 (4)	0.0190 (5)	−0.0025 (3)	−0.0001 (4)	0.0023 (3)
O2	0.0128 (4)	0.0151 (4)	0.0179 (5)	−0.0061 (4)	−0.0050 (4)	0.0048 (4)
O3	0.0107 (4)	0.0149 (4)	0.0178 (5)	−0.0036 (3)	−0.0001 (4)	−0.0047 (4)
N1	0.0149 (5)	0.0136 (5)	0.0133 (5)	−0.0032 (4)	−0.0032 (4)	−0.0005 (4)
N2	0.0125 (5)	0.0137 (5)	0.0144 (5)	−0.0030 (4)	−0.0024 (4)	−0.0013 (4)
N3	0.0140 (5)	0.0206 (6)	0.0157 (6)	−0.0065 (4)	−0.0047 (4)	0.0053 (4)
C1	0.0136 (6)	0.0114 (6)	0.0130 (6)	−0.0029 (4)	−0.0018 (5)	−0.0025 (4)
C2	0.0150 (6)	0.0150 (6)	0.0176 (6)	−0.0052 (5)	0.0031 (5)	−0.0045 (5)
C3	0.0195 (7)	0.0142 (6)	0.0141 (6)	−0.0053 (5)	0.0031 (5)	−0.0022 (5)
C4	0.0187 (6)	0.0119 (6)	0.0119 (6)	−0.0028 (5)	−0.0015 (5)	−0.0033 (4)
C5	0.0222 (7)	0.0171 (6)	0.0155 (6)	−0.0049 (5)	−0.0061 (5)	0.0017 (5)
S1	0.00895 (15)	0.01018 (15)	0.01081 (15)	−0.00313 (11)	−0.00176 (11)	−0.00010 (11)
O4	0.0121 (4)	0.0105 (4)	0.0172 (5)	−0.0015 (3)	−0.0033 (4)	−0.0003 (3)
O5	0.0103 (4)	0.0192 (5)	0.0165 (5)	−0.0067 (4)	−0.0035 (4)	0.0039 (4)
O6	0.0126 (4)	0.0167 (5)	0.0139 (5)	−0.0054 (4)	−0.0010 (4)	0.0033 (4)
O7	0.0178 (5)	0.0149 (5)	0.0171 (5)	−0.0022 (4)	−0.0044 (4)	−0.0054 (4)
O8	0.0165 (5)	0.0142 (4)	0.0172 (5)	−0.0062 (4)	−0.0021 (4)	−0.0024 (4)

Geometric parameters (Å, º) top

Co1—O1	2.0838 (9)	N3—H3A	0.9099
Co1—O1ⁱ	2.0838 (9)	N3—H3B	0.9100
Co1—O2	2.0643 (9)	N3—C1	1.3216 (17)
Co1—O2ⁱ	2.0643 (9)	C2—H2	0.9500
Co1—O3ⁱ	2.1140 (10)	C2—C3	1.362 (2)
Co1—O3	2.1140 (10)	C3—H3	0.9500
O1—H1A	0.8400	C3—C4	1.412 (2)
O1—H1B	0.8400	C4—C5	1.4935 (19)
O2—H2A	0.8400	C5—H5A	0.9800
O2—H2B	0.8400	C5—H5B	0.9800
O3—H3C	0.8400	C5—H5C	0.9800
O3—H3D	0.8400	S1—O4	1.4772 (10)
N1—C1	1.3503 (17)	S1—O5	1.4749 (9)
N1—C4	1.3352 (17)	S1—O6	1.4851 (10)
N2—H2N	0.9101	S1—O7	1.4834 (10)
N2—C1	1.3621 (17)	O8—H8A	0.8400
N2—C2	1.3558 (17)	O8—H8B	0.8400

O1ⁱ—Co1—O1	180.0	H3A—N3—H3B	118.7
O1ⁱ—Co1—O3	89.31 (4)	C1—N3—H3A	121.5
O1—Co1—O3	90.69 (4)	C1—N3—H3B	119.7
O1ⁱ—Co1—O3ⁱ	90.69 (4)	N1—C1—N2	121.68 (12)
O1—Co1—O3ⁱ	89.31 (4)	N3—C1—N1	119.51 (12)
O2ⁱ—Co1—O1ⁱ	93.59 (4)	N3—C1—N2	118.82 (12)
O2—Co1—O1	93.59 (4)	N2—C2—H2	120.1
O2ⁱ—Co1—O1	86.41 (4)	N2—C2—C3	119.73 (13)
O2—Co1—O1ⁱ	86.41 (4)	C3—C2—H2	120.1
O2—Co1—O2ⁱ	180.0	C2—C3—H3	121.2
O2ⁱ—Co1—O3	88.21 (4)	C2—C3—C4	117.61 (12)
O2ⁱ—Co1—O3ⁱ	91.79 (4)	C4—C3—H3	121.2
O2—Co1—O3ⁱ	88.21 (4)	N1—C4—C3	122.45 (12)
O2—Co1—O3	91.79 (4)	N1—C4—C5	116.47 (12)
O3—Co1—O3ⁱ	180.0	C3—C4—C5	121.07 (12)
Co1—O1—H1A	121.3	C4—C5—H5A	109.5
Co1—O1—H1B	133.1	C4—C5—H5B	109.5
H1A—O1—H1B	105.3	C4—C5—H5C	109.5
Co1—O2—H2A	123.6	H5A—C5—H5B	109.5
Co1—O2—H2B	115.8	H5A—C5—H5C	109.5
H2A—O2—H2B	109.5	H5B—C5—H5C	109.5
Co1—O3—H3C	116.1	O4—S1—O6	110.08 (6)
Co1—O3—H3D	115.8	O4—S1—O7	108.96 (6)
H3C—O3—H3D	112.0	O5—S1—O4	109.75 (6)
C4—N1—C1	117.86 (12)	O5—S1—O6	108.84 (6)
C1—N2—H2N	118.7	O5—S1—O7	109.68 (6)
C2—N2—H2N	120.7	O7—S1—O6	109.52 (6)
C2—N2—C1	120.59 (12)	H8A—O8—H8B	102.1

N2—C2—C3—C4	0.4 (2)	C2—N2—C1—N3	178.45 (12)
C1—N1—C4—C3	2.59 (19)	C2—C3—C4—N1	−2.6 (2)
C1—N1—C4—C5	−176.26 (12)	C2—C3—C4—C5	176.18 (12)
C1—N2—C2—C3	1.75 (19)	C4—N1—C1—N2	−0.37 (19)
C2—N2—C1—N1	−1.82 (19)	C4—N1—C1—N3	179.37 (12)

Symmetry code: (i) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O8	0.84	1.92	2.7562 (14)	171
O1—H1B···O4	0.84	1.97	2.8050 (13)	178
O2—H2A···O4ⁱⁱ	0.84	1.92	2.7533 (14)	173
O2—H2B···O5	0.84	1.87	2.7077 (13)	174
O3—H3C···O8ⁱⁱ	0.84	1.92	2.7508 (13)	170
O3—H3D···O7ⁱⁱⁱ	0.84	1.95	2.7865 (14)	177
N2—H2N···O6^iv	0.91	1.81	2.7155 (15)	172
N3—H3A···O5^iv	0.91	1.87	2.7776 (15)	175
N3—H3B···O6^v	0.91	1.98	2.8775 (15)	168
O8—H8A···O7ⁱⁱⁱ	0.84	1.98	2.7684 (14)	156
O8—H8B···O7^vi	0.84	2.02	2.8582 (14)	172

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

Experimental details

Crystal data
Chemical formula	(C₅H₈N₃)₂[Co(H₂O)₆](SO₄)₂·2H₂O
M_r	615.49
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.4116 (6), 7.7751 (7), 13.0423 (12)
α, β, γ (°)	80.136 (1), 80.413 (1), 73.231 (1)
V (Å³)	608.57 (10)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.96
Crystal size (mm)	0.19 × 0.19 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2009)
T_min, T_max	0.780, 0.893
No. of measured, independent and observed [I > 2σ(I)] reflections	10780, 3085, 2944
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.073, 1.09
No. of reflections	3085
No. of parameters	161
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.40

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2009), SHELXM (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Selected bond lengths (Å) top

Co1—O1	2.0838 (9)	Co1—O3	2.1140 (10)
Co1—O2	2.0643 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O8	0.84	1.92	2.7562 (14)	171
O1—H1B···O4	0.84	1.97	2.8050 (13)	178
O2—H2A···O4ⁱ	0.84	1.92	2.7533 (14)	173
O2—H2B···O5	0.84	1.87	2.7077 (13)	174
O3—H3C···O8ⁱ	0.84	1.92	2.7508 (13)	170
O3—H3D···O7ⁱⁱ	0.84	1.95	2.7865 (14)	177
N2—H2N···O6ⁱⁱⁱ	0.91	1.81	2.7155 (15)	172
N3—H3A···O5ⁱⁱⁱ	0.91	1.87	2.7776 (15)	175
N3—H3B···O6^iv	0.91	1.98	2.8775 (15)	168
O8—H8A···O7ⁱⁱ	0.84	1.98	2.7684 (14)	156
O8—H8B···O7^v	0.84	2.02	2.8582 (14)	172

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

Acknowledgements

We thank the Chemistry Department of Tulane University for support of the X-ray crystallographic facility.

References

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2009). SADABS. University of Göttingen, Germany. Google Scholar
Shiu, K.-B., Yen, C.-H., Liao, F.-L. & Wang, S.-L. (2004). Acta Cryst. E60, m35–m37. Web of Science CSD CrossRef IUCr Journals Google Scholar