4-[3,5-Bis(ethoxy­carbon­yl)-2,6-dimethyl-4-pyrid­yl]pyridinium nitrate

Li, Y.

doi:10.1107/S1600536810015035

organic compounds

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Volume 66| Part 5| May 2010| Page o1224

https://doi.org/10.1107/S1600536810015035

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4-[3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-4-pyridyl]pyridinium nitrate

Yumei Li ^a ^*

^aDepartment of Chemistry, Dezhou University, Shandong 253023, People's Republic of China
^*Correspondence e-mail: liyumei_dzc@yahoo.com.cn

(Received 22 April 2010; accepted 24 April 2010; online 30 April 2010)

In the title molecular salt, C₁₈H₂₁N₂O₄⁺·NO₃⁻, the dihedral angle between the two pyridine rings is 61.24 (8)°. In the crystal, the cation and anion are linked by intermolecular N—H⋯O hydrogen bonds.

Related literature

For general background to metal-organic frameworks, see: Zhang et al. (2003 ).

Experimental

Crystal data

C₁₈H₂₁N₂O₄⁺·NO₃⁻
M_r = 391.38
Orthorhombic, P n a 2₁
a = 9.075 (9) Å
b = 15.496 (15) Å
c = 14.125 (13) Å
V = 1987 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.37 × 0.33 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.963, T_max = 0.975
9196 measured reflections
3395 independent reflections
2877 reflections with I > 2σ(I)
R_int = 0.156

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.115
S = 1.00
3395 reflections
258 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O5ⁱ	0.86	1.90	2.752 (3)	171
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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 global, I. DOI: https://doi.org/10.1107/S1600536810015035/hb5413sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015035/hb5413Isup2.hkl

checkCIF report

Comment top

In recent years, the design and construction of metal-organic frameworks through the coordination of metal ions with multifunctional organic ligands have received extensive attention due to their impressive structural diversities in architectures and their potential applications as functional materials (Zhang et al., 2003). Whereas, it is more important to design the novel organic ligand. Here, we describe the recystallization and structural characterization of the title compound.

The molecular structure is shown in Fig 1. The dihedral angle between the two pyridine rings is 61.24 (8) °. N—H···O and N—H···N hydrogen bonding between the cations and anions leads to a consolidation of the structure (Fig. 2; Table 1).

Related literature top

For general background to metal-organic frameworks, see: Zhang et al. (2003).

Experimental top

A mixture of 2,6-dimethyl-4-(4-pyridyl)pyridine-3,5-dicarboxylate (1 mmol, 0.39 g) and ammonium nitrate (2 mmol, 0.16 g) in 20 ml ethanol was refluxed for half an hour. The obtained filtrate was evaporated in one open flask at room temperature. One week later, yellow blocks of (I) were obained. Anal. C₂₀H₂₂NO₇: C, 55.61; H, 5.41; N, 7.21 %. Found: C, 55.56; H, 5.33; N, 7.10 %.

Structure description top

For general background to metal-organic frameworks, see: Zhang et al. (2003).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 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. The moleular structure of (I) with displacement ellipsoids drawn at the 30% probability level; H atoms are given as spheres of arbitrary radius.

4-[3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-4-pyridyl]pyridinium nitrate top

Crystal data top

C₁₈H₂₁N₂O₄⁺·NO₃⁻	F(000) = 824
M_r = 391.38	D_x = 1.309 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3948 reflections
a = 9.075 (9) Å	θ = 2.2–25.9°
b = 15.496 (15) Å	µ = 0.10 mm⁻¹
c = 14.125 (13) Å	T = 296 K
V = 1987 (3) Å³	Block, yellow
Z = 4	0.37 × 0.33 × 0.24 mm

Data collection top

Bruker APEXII CCD diffractometer	3395 independent reflections
Radiation source: fine-focus sealed tube	2877 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.156
phi and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
T_min = 0.963, T_max = 0.975	k = −18→10
9196 measured reflections	l = −15→16

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)] = 0.043	H-atom parameters constrained
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.069P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
3395 reflections	Δρ_max = 0.17 e Å⁻³
258 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0134 (12)

Crystal data top

C₁₈H₂₁N₂O₄⁺·NO₃⁻	V = 1987 (3) Å³
M_r = 391.38	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 9.075 (9) Å	µ = 0.10 mm⁻¹
b = 15.496 (15) Å	T = 296 K
c = 14.125 (13) Å	0.37 × 0.33 × 0.24 mm

Data collection top

Bruker APEXII CCD diffractometer	3395 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2877 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.975	R_int = 0.156
9196 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	1 restraint
wR(F²) = 0.115	H-atom parameters constrained
S = 1.00	Δρ_max = 0.17 e Å⁻³
3395 reflections	Δρ_min = −0.21 e Å⁻³
258 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	−0.10369 (19)	1.05766 (11)	0.20140 (17)	0.0498 (5)
H1	−0.2022	1.0738	0.1979	0.060*
C2	−0.06618 (18)	0.97534 (10)	0.22947 (15)	0.0460 (5)
H2	−0.1393	0.9361	0.2460	0.055*
C3	0.08043 (17)	0.95128 (10)	0.23295 (14)	0.0372 (4)
C4	0.18687 (19)	1.01225 (10)	0.20996 (15)	0.0476 (5)
H4	0.2863	0.9980	0.2128	0.057*
C5	0.14389 (18)	1.09410 (11)	0.18284 (16)	0.0496 (5)
H5	0.2145	1.1352	0.1671	0.060*
C6	0.12219 (17)	0.86086 (9)	0.26006 (13)	0.0352 (4)
C7	0.20576 (18)	0.84398 (10)	0.34073 (13)	0.0389 (4)
C8	0.24140 (19)	0.75802 (10)	0.36386 (14)	0.0420 (4)
C9	0.10982 (18)	0.70663 (10)	0.23457 (14)	0.0404 (4)
C10	0.07328 (16)	0.79095 (9)	0.20499 (13)	0.0365 (4)
C11	0.0619 (2)	0.62888 (10)	0.1782 (2)	0.0585 (6)
H11A	0.0733	0.5778	0.2161	0.088*
H11B	0.1214	0.6241	0.1223	0.088*
H11C	−0.0397	0.6352	0.1605	0.088*
C12	0.3328 (3)	0.73555 (13)	0.44732 (18)	0.0596 (6)
H12A	0.3463	0.6742	0.4498	0.089*
H12B	0.2842	0.7546	0.5039	0.089*
H12C	0.4270	0.7633	0.4422	0.089*
C13	−0.00568 (19)	0.80402 (10)	0.11383 (15)	0.0428 (5)
C14	0.0243 (3)	0.85562 (17)	−0.0438 (2)	0.0784 (7)
H14A	0.0605	0.9081	−0.0731	0.094*
H14B	−0.0825	0.8571	−0.0447	0.094*
C15	0.0777 (6)	0.77990 (19)	−0.0969 (3)	0.1235 (14)
H15A	0.1834	0.7783	−0.0949	0.185*
H15B	0.0455	0.7838	−0.1615	0.185*
H15C	0.0388	0.7282	−0.0689	0.185*
C16	0.2496 (2)	0.91621 (11)	0.40602 (15)	0.0482 (5)
C17	0.4449 (3)	1.00763 (16)	0.4561 (2)	0.0846 (8)
H17A	0.3935	1.0611	0.4428	0.102*
H17B	0.4291	0.9931	0.5221	0.102*
C18	0.5981 (3)	1.0179 (2)	0.4383 (3)	0.1241 (13)
H18A	0.6478	0.9642	0.4494	0.186*
H18B	0.6373	1.0613	0.4798	0.186*
H18C	0.6126	1.0352	0.3737	0.186*
N3	0.53347 (15)	0.16998 (8)	0.17481 (14)	0.0488 (4)
N1	0.19326 (16)	0.69168 (8)	0.31060 (12)	0.0440 (4)
N2	0.00187 (16)	1.11408 (8)	0.17919 (14)	0.0484 (4)
H2A	−0.0231	1.1652	0.1619	0.058*
O1	−0.12303 (17)	0.77548 (12)	0.09504 (13)	0.0770 (5)
O2	0.07701 (15)	0.85022 (8)	0.05417 (12)	0.0595 (4)
O3	0.38730 (15)	0.93821 (9)	0.39511 (13)	0.0643 (4)
O4	0.16624 (19)	0.94931 (12)	0.46120 (15)	0.0888 (6)
O5	0.43298 (14)	0.21643 (8)	0.14155 (13)	0.0615 (4)
O6	0.64708 (15)	0.20368 (9)	0.20110 (18)	0.0856 (6)
O7	0.51772 (17)	0.09067 (8)	0.17934 (19)	0.0873 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0446 (8)	0.0371 (9)	0.0676 (15)	0.0042 (7)	−0.0064 (9)	−0.0048 (9)
C2	0.0444 (8)	0.0322 (8)	0.0613 (13)	−0.0021 (7)	0.0003 (9)	−0.0025 (9)
C3	0.0448 (8)	0.0281 (7)	0.0388 (10)	−0.0001 (6)	−0.0026 (7)	−0.0020 (7)
C4	0.0435 (8)	0.0332 (8)	0.0660 (14)	−0.0010 (6)	0.0001 (9)	0.0057 (8)
C5	0.0494 (8)	0.0338 (8)	0.0657 (14)	−0.0061 (7)	0.0023 (10)	0.0049 (9)
C6	0.0384 (7)	0.0260 (7)	0.0411 (11)	0.0003 (6)	0.0040 (7)	−0.0009 (7)
C7	0.0420 (8)	0.0316 (7)	0.0429 (11)	0.0000 (6)	0.0031 (8)	−0.0030 (7)
C8	0.0477 (8)	0.0370 (8)	0.0414 (11)	0.0053 (7)	0.0047 (8)	0.0016 (8)
C9	0.0439 (8)	0.0279 (7)	0.0495 (12)	−0.0014 (6)	0.0080 (8)	−0.0044 (7)
C10	0.0386 (7)	0.0275 (7)	0.0434 (11)	−0.0017 (6)	0.0034 (7)	−0.0042 (7)
C11	0.0677 (11)	0.0310 (8)	0.0768 (16)	−0.0052 (7)	−0.0037 (12)	−0.0144 (9)
C12	0.0761 (13)	0.0506 (11)	0.0519 (14)	0.0082 (9)	−0.0100 (11)	0.0058 (10)
C13	0.0418 (8)	0.0355 (8)	0.0513 (12)	0.0007 (7)	−0.0003 (8)	−0.0081 (8)
C14	0.0979 (16)	0.0791 (14)	0.0582 (17)	−0.0109 (13)	−0.0182 (13)	0.0275 (13)
C15	0.211 (4)	0.095 (2)	0.064 (2)	0.013 (2)	−0.011 (3)	0.0004 (19)
C16	0.0559 (10)	0.0384 (8)	0.0502 (12)	0.0046 (7)	−0.0052 (9)	−0.0088 (9)
C17	0.0961 (17)	0.0685 (13)	0.089 (2)	−0.0206 (13)	−0.0115 (15)	−0.0356 (13)
C18	0.0940 (18)	0.126 (2)	0.153 (3)	−0.0447 (18)	0.001 (2)	−0.069 (2)
N3	0.0451 (7)	0.0320 (6)	0.0694 (12)	−0.0002 (6)	0.0099 (8)	−0.0050 (8)
N1	0.0547 (8)	0.0281 (6)	0.0493 (10)	0.0016 (6)	0.0050 (7)	0.0034 (7)
N2	0.0615 (9)	0.0258 (6)	0.0578 (11)	0.0058 (6)	−0.0071 (8)	0.0018 (7)
O1	0.0578 (8)	0.1056 (12)	0.0677 (12)	−0.0226 (8)	−0.0104 (8)	−0.0015 (9)
O2	0.0662 (8)	0.0590 (7)	0.0533 (10)	−0.0079 (7)	−0.0060 (7)	0.0137 (7)
O3	0.0663 (8)	0.0602 (7)	0.0664 (11)	−0.0137 (6)	−0.0004 (8)	−0.0270 (8)
O4	0.0803 (10)	0.0871 (10)	0.0990 (14)	0.0011 (8)	0.0135 (10)	−0.0543 (10)
O5	0.0521 (7)	0.0398 (6)	0.0925 (13)	0.0035 (5)	−0.0088 (7)	−0.0036 (7)
O6	0.0535 (7)	0.0432 (7)	0.1601 (19)	−0.0011 (6)	−0.0234 (10)	0.0018 (10)
O7	0.0748 (8)	0.0284 (6)	0.159 (2)	−0.0030 (6)	0.0012 (12)	0.0025 (9)

Geometric parameters (Å, º) top

C1—N2	1.334 (2)	C12—H12B	0.9600
C1—C2	1.379 (3)	C12—H12C	0.9600
C1—H1	0.9300	C13—O1	1.183 (2)
C2—C3	1.383 (3)	C13—O2	1.336 (2)
C2—H2	0.9300	C14—O2	1.466 (3)
C3—C4	1.390 (2)	C14—C15	1.474 (5)
C3—C6	1.501 (2)	C14—H14A	0.9700
C4—C5	1.381 (3)	C14—H14B	0.9700
C4—H4	0.9300	C15—H15A	0.9600
C5—N2	1.327 (3)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—C7	1.394 (3)	C16—O4	1.201 (3)
C6—C10	1.406 (2)	C16—O3	1.304 (3)
C7—C8	1.409 (3)	C17—C18	1.422 (4)
C7—C16	1.504 (3)	C17—O3	1.474 (3)
C8—N1	1.347 (2)	C17—H17A	0.9700
C8—C12	1.483 (3)	C17—H17B	0.9700
C9—N1	1.334 (3)	C18—H18A	0.9600
C9—C10	1.411 (2)	C18—H18B	0.9600
C9—C11	1.508 (3)	C18—H18C	0.9600
C10—C13	1.488 (3)	N3—O6	1.214 (2)
C11—H11A	0.9600	N3—O7	1.239 (2)
C11—H11B	0.9600	N3—O5	1.253 (2)
C11—H11C	0.9600	N2—H2A	0.8600
C12—H12A	0.9600

N2—C1—C2	119.78 (16)	H12B—C12—H12C	109.5
N2—C1—H1	120.1	O1—C13—O2	124.4 (2)
C2—C1—H1	120.1	O1—C13—C10	125.22 (19)
C1—C2—C3	119.82 (16)	O2—C13—C10	110.38 (15)
C1—C2—H2	120.1	O2—C14—C15	109.1 (2)
C3—C2—H2	120.1	O2—C14—H14A	109.9
C2—C3—C4	118.51 (16)	C15—C14—H14A	109.9
C2—C3—C6	120.24 (14)	O2—C14—H14B	109.9
C4—C3—C6	121.24 (15)	C15—C14—H14B	109.9
C5—C4—C3	119.53 (16)	H14A—C14—H14B	108.3
C5—C4—H4	120.2	C14—C15—H15A	109.5
C3—C4—H4	120.2	C14—C15—H15B	109.5
N2—C5—C4	119.97 (15)	H15A—C15—H15B	109.5
N2—C5—H5	120.0	C14—C15—H15C	109.5
C4—C5—H5	120.0	H15A—C15—H15C	109.5
C7—C6—C10	118.67 (14)	H15B—C15—H15C	109.5
C7—C6—C3	121.41 (14)	O4—C16—O3	124.64 (19)
C10—C6—C3	119.90 (16)	O4—C16—C7	123.29 (18)
C6—C7—C8	119.46 (15)	O3—C16—C7	112.07 (16)
C6—C7—C16	120.38 (15)	C18—C17—O3	109.0 (2)
C8—C7—C16	120.04 (17)	C18—C17—H17A	109.9
N1—C8—C7	121.18 (18)	O3—C17—H17A	109.9
N1—C8—C12	116.50 (16)	C18—C17—H17B	109.9
C7—C8—C12	122.32 (17)	O3—C17—H17B	109.9
N1—C9—C10	122.17 (15)	H17A—C17—H17B	108.3
N1—C9—C11	116.72 (16)	C17—C18—H18A	109.5
C10—C9—C11	121.04 (18)	C17—C18—H18B	109.5
C6—C10—C9	118.39 (17)	H18A—C18—H18B	109.5
C6—C10—C13	121.75 (15)	C17—C18—H18C	109.5
C9—C10—C13	119.71 (15)	H18A—C18—H18C	109.5
C9—C11—H11A	109.5	H18B—C18—H18C	109.5
C9—C11—H11B	109.5	O6—N3—O7	120.59 (16)
H11A—C11—H11B	109.5	O6—N3—O5	119.06 (15)
C9—C11—H11C	109.5	O7—N3—O5	120.34 (16)
H11A—C11—H11C	109.5	C9—N1—C8	120.07 (14)
H11B—C11—H11C	109.5	C5—N2—C1	122.38 (15)
C8—C12—H12A	109.5	C5—N2—H2A	118.8
C8—C12—H12B	109.5	C1—N2—H2A	118.8
H12A—C12—H12B	109.5	C13—O2—C14	116.27 (18)
C8—C12—H12C	109.5	C16—O3—C17	117.49 (18)
H12A—C12—H12C	109.5

N2—C1—C2—C3	−1.1 (3)	C11—C9—C10—C6	−179.48 (17)
C1—C2—C3—C4	1.6 (3)	N1—C9—C10—C13	173.11 (15)
C1—C2—C3—C6	−177.80 (19)	C11—C9—C10—C13	−3.8 (2)
C2—C3—C4—C5	−1.1 (3)	C6—C10—C13—O1	−124.4 (2)
C6—C3—C4—C5	178.22 (19)	C9—C10—C13—O1	60.1 (3)
C3—C4—C5—N2	0.2 (3)	C6—C10—C13—O2	57.8 (2)
C2—C3—C6—C7	−117.5 (2)	C9—C10—C13—O2	−117.67 (17)
C4—C3—C6—C7	63.1 (3)	C6—C7—C16—O4	76.4 (3)
C2—C3—C6—C10	60.7 (3)	C8—C7—C16—O4	−99.8 (2)
C4—C3—C6—C10	−118.7 (2)	C6—C7—C16—O3	−103.4 (2)
C10—C6—C7—C8	1.3 (2)	C8—C7—C16—O3	80.4 (2)
C3—C6—C7—C8	179.50 (16)	C10—C9—N1—C8	2.3 (3)
C10—C6—C7—C16	−174.90 (16)	C11—C9—N1—C8	179.39 (17)
C3—C6—C7—C16	3.3 (2)	C7—C8—N1—C9	−0.2 (3)
C6—C7—C8—N1	−1.6 (3)	C12—C8—N1—C9	179.67 (17)
C16—C7—C8—N1	174.62 (16)	C4—C5—N2—C1	0.3 (3)
C6—C7—C8—C12	178.55 (17)	C2—C1—N2—C5	0.1 (3)
C16—C7—C8—C12	−5.3 (3)	O1—C13—O2—C14	−7.9 (3)
C7—C6—C10—C9	0.7 (2)	C10—C13—O2—C14	169.90 (17)
C3—C6—C10—C9	−177.59 (15)	C15—C14—O2—C13	−85.5 (3)
C7—C6—C10—C13	−174.87 (15)	O4—C16—O3—C17	1.1 (3)
C3—C6—C10—C13	6.9 (2)	C7—C16—O3—C17	−179.12 (19)
N1—C9—C10—C6	−2.5 (2)	C18—C17—O3—C16	176.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5ⁱ	0.86	1.90	2.752 (3)	171

Symmetry code: (i) x−1/2, −y+3/2, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁N₂O₄⁺·NO₃⁻
M_r	391.38
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	296
a, b, c (Å)	9.075 (9), 15.496 (15), 14.125 (13)
V (Å³)	1987 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.37 × 0.33 × 0.24

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.963, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	9196, 3395, 2877
R_int	0.156
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.115, 1.00
No. of reflections	3395
No. of parameters	258
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.21

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), 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
N2—H2A···O5ⁱ	0.86	1.90	2.752 (3)	171

Symmetry code: (i) x−1/2, −y+3/2, z.

References

Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, X. T., Lu, C. Z., Zhang, Q. Z., Lu, S. F., Yang, W. B., Liu, J. C. & Zhuang, H. H. (2003). Eur. J. Inorg. Chem. pp. 1181–1185. CSD CrossRef Google Scholar

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Volume 66| Part 5| May 2010| Page o1224

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