6-Nicotinamido-2-naphthoic acid

Song, Y.-S.; Lee, S.W.

doi:10.1107/S1600536812024051

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o1978

https://doi.org/10.1107/S1600536812024051

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6-Nicotinamido-2-naphthoic acid

Yun-Sung Song ^a and Soon W. Lee ^a ^*

^aDepartment of Chemistry (BK21), Sungkyunkwan University, Natural Science Campus, Suwon 440-746, Republic of Korea
^*Correspondence e-mail: soonwlee@skku.edu

(Received 17 May 2012; accepted 26 May 2012; online 2 June 2012)

In the title molecule, C₁₇H₁₂N₂O₃, the naphthalene ring system and the pyridin-3-yl rings are nearly coplanar with a dihedral angle between them of 2.28 (8)°. In the crystal, the hydroxy and amide N atoms participate in hydrogen bonds, which connect the molecules into a two-dimensional network parallel to (101).

Related literature

For coordination polymers based on linking ligands with O- and N-donors see: Robin & Fromm, 2006 . For d–f coordination polymers based on linking ligands with pyridyl–carboxylate terminals see: Hu et al. (2012 ); Chen et al. (2010 ); Tang et al. (2010 ); Yue et al. (2011 ); Zhu et al. (2010 ). For related potential linking ligands see: Han & Lee, 2012 ; Zheng & Lee, 2012 .

Experimental

Crystal data

C₁₇H₁₂N₂O₃
M_r = 292.29
Monoclinic, C c
a = 25.901 (3) Å
b = 6.2097 (7) Å
c = 8.6080 (9) Å
β = 103.258 (9)°
V = 1347.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.40 × 0.20 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.961, T_max = 0.992
11725 measured reflections
1693 independent reflections
2845 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.092
S = 1.05
1693 reflections
207 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1ⁱ	0.92 (3)	2.01 (3)	2.926 (2)	170 (2)
O2—H2O⋯N1ⁱⁱ	0.84 (3)	1.88 (4)	2.708 (2)	170 (3)
Symmetry codes: (i) $[x, -y, z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker (2008 ); cell refinement: SAINT (Bruker (2008); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812024051/mw2071sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812024051/mw2071Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812024051/mw2071Isup3.cml

checkCIF report

Comment top

Bis(pyridyl)- and dicarboxylate-type linking ligands have been typically employed for the preparation of coordination polymers (Robin & Fromm, 2006). The vast majority of known coordination polymers contain either a d- or an f-block metal. However, several research groups recently prepared polymers containing both d- and f-block metals within their frameworks by utilizing linking ligands possessing pyridyl–carboxylate terminal groups (Hu et al., 2012; Chen et al., 2010; Tang et al., 2010; Yue et al., 2011; Zhu et al., 2010). Consistent with the hard–soft acid–base concept, the harder oxygen atoms are bonded to the f-block metals and the softer nitrogen atoms are bonded to the d-block metals in these polymers. Our research group recently reported the structures of two potential linking ligands with pyridyl–carboxylate terminal groups (Han & Lee, 2012; Zheng & Lee, 2012) and here we report the structure of third.

The molecular structure of the title molecule with the atom-labeling scheme is given in Figure 1. The naphthalene and 3-pyridyl rings are nearly coplanar with a dihedral angle between them of 2.28 (8)°. The N2–C6 bond length (1.343 (2) Å) indicates a C–N single bond. The intermolecular O–H···N and N–H···O (carbonyl) hydrogen bonds (Table 1) connect the molecules along the a- and c-axes, respectively, leading to a 2-D network in the [101] direction (Figure 2).

Related literature top

For coordination polymers based on linking ligands with O- and N-donors see: Robin & Fromm, 2006. For d–f coordination polymers based on linking ligands with pyridyl–carboxylate terminals see: Hu et al. (2012); Chen et al. (2010); Tang et al. (2010); Yue et al. (2011); Zhu et al. (2010). For related potential linking ligands see: Han & Lee, 2012; Zheng & Lee, 2012.

Experimental top

A stirred mixture of 6-amino-2-naphthoic acid (0.94 g, 5 mmol) and N,N-dimethyl-4-aminopyridine (0.02 g, 0.17 mmol) in dimethylacetamide (15 mL) was heated at 80 °C for 30 min under argon. The solution was cooled to 10 °C, and nicotinoyl chloride hydrochloride (0.89 g, 5 mmol) was added. The temperature was then raised slowly to 50 °C and was maintained there for 8 h. On addition of dichloromethane to the resulting mixture, a precipitate was formed, which was filtered off and dried under vacuum at 100°C. The product was recrystallized from methanol to give crystals of the title compound (1.22 g, 4.2 mmol, 83.9% yield). mp: 593–595 K (decomp). ¹H NMR (500 MHz, DMSO-d₆, d) 11.06 (s, 1H, carboxylic acid OH), 9.35 (s, 1H, amide NH), 8.93 (d, 1H, pyridine proton), 8.71 (d, 1H, pyridine proton), 8.56 (s, 2H, naphthalene proton), 8.14 (d, 1H, pyridine proton), 7.96–7.94 (m, 4H, naphthalene proton), 7.88 (t, 1H, pyridine proton). ¹³C{¹H} NMR (125 MHz, DMSO-d₆, d) 167.3, 163.1, 148.7, 145.7, 139.5, 138.4, 135.4, 131.6, 130.2, 129.9, 129.1, 127.8, 127.0, 125.75, 125.0, 121.3, 116.2. IR (KBr, cm^-1): 3623 (w), 3328 (w), 2925 (s), 2640 (s), 2372 (s), 2075 (s), 1800 (m), 1621 (m), 1551 (m), 1291 (m), 1195 (m), 1018 (m), 773 (m), 724 (m), 678 (m), 633 (m), 494 (s).

Structure description top

For coordination polymers based on linking ligands with O- and N-donors see: Robin & Fromm, 2006. For d–f coordination polymers based on linking ligands with pyridyl–carboxylate terminals see: Hu et al. (2012); Chen et al. (2010); Tang et al. (2010); Yue et al. (2011); Zhu et al. (2010). For related potential linking ligands see: Han & Lee, 2012; Zheng & Lee, 2012.

Computing details top

Data collection: APEX2 (Bruker (2008); cell refinement: SAINT (Bruker (2008); data reduction: SAINT (Bruker (2008); 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 molecular structure of the title compound showing the atomic numbering and 50% probability displacement ellipsoids.
	Fig. 2. A portion of the crystal packing showing a 2-D H-bonded (dashed lines) network.

6-Nicotinamido-2-naphthoic acid top

Crystal data top

C₁₇H₁₂N₂O₃	F(000) = 608
M_r = 292.29	D_x = 1.441 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 6523 reflections
a = 25.901 (3) Å	θ = 3.2–28.5°
b = 6.2097 (7) Å	µ = 0.10 mm⁻¹
c = 8.6080 (9) Å	T = 296 K
β = 103.258 (9)°	Plate, yellow
V = 1347.6 (3) Å³	0.40 × 0.20 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	1693 independent reflections
Radiation source: sealed tube	2845 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
φ and ω scans	θ_max = 28.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −34→34
T_min = 0.961, T_max = 0.992	k = −8→8
11725 measured reflections	l = −11→11

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0641P)² + 0.0998P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
1693 reflections	Δρ_max = 0.24 e Å⁻³
207 parameters	Δρ_min = −0.18 e Å⁻³
2 restraints	Absolute structure: The absolute structure could not be determined with certainty
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₇H₁₂N₂O₃	V = 1347.6 (3) Å³
M_r = 292.29	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 25.901 (3) Å	µ = 0.10 mm⁻¹
b = 6.2097 (7) Å	T = 296 K
c = 8.6080 (9) Å	0.40 × 0.20 × 0.08 mm
β = 103.258 (9)°

Data collection top

Bruker APEXII CCD diffractometer	1693 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2845 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.992	R_int = 0.035
11725 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	2 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.24 e Å⁻³
1693 reflections	Δρ_min = −0.18 e Å⁻³
207 parameters	Absolute structure: The absolute structure could not be determined with certainty

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
O1	0.31793 (6)	−0.2140 (2)	0.26571 (17)	0.0391 (3)
O2	0.62483 (6)	0.3924 (3)	0.1855 (2)	0.0454 (4)
H2O	0.6456 (12)	0.485 (6)	0.163 (4)	0.059 (8)*
O3	0.59863 (7)	0.6936 (3)	0.2841 (3)	0.0583 (5)
N1	0.19038 (7)	−0.1634 (3)	0.5762 (2)	0.0406 (4)
N2	0.33612 (6)	0.0227 (3)	0.47225 (19)	0.0354 (4)
H2N	0.3278 (9)	0.070 (4)	0.565 (3)	0.037 (6)*
C1	0.23346 (8)	−0.0931 (3)	0.5307 (2)	0.0359 (4)
H1	0.2453	0.0463	0.5580	0.043*
C2	0.17334 (8)	−0.3618 (4)	0.5349 (3)	0.0432 (5)
H2	0.1435	−0.4116	0.5666	0.052*
C3	0.19787 (9)	−0.4971 (4)	0.4473 (3)	0.0430 (5)
H3	0.1846	−0.6346	0.4200	0.052*
C4	0.24257 (8)	−0.4253 (4)	0.4005 (2)	0.0386 (4)
H4	0.2598	−0.5133	0.3409	0.046*
C5	0.26131 (7)	−0.2192 (3)	0.4442 (2)	0.0301 (4)
C6	0.30789 (7)	−0.1368 (3)	0.3864 (2)	0.0301 (4)
C7	0.38118 (7)	0.1288 (3)	0.4401 (2)	0.0307 (4)
C8	0.39174 (8)	0.3389 (3)	0.5049 (2)	0.0340 (4)
H8	0.3691	0.4013	0.5616	0.041*
C9	0.43521 (7)	0.4492 (3)	0.4839 (2)	0.0320 (4)
H9	0.4420	0.5865	0.5270	0.038*
C10	0.47019 (7)	0.3577 (3)	0.3975 (2)	0.0283 (4)
C11	0.51502 (7)	0.4691 (3)	0.3710 (2)	0.0308 (4)
H11	0.5221	0.6080	0.4106	0.037*
C12	0.54815 (7)	0.3749 (3)	0.2878 (2)	0.0311 (4)
C13	0.53849 (8)	0.1624 (3)	0.2294 (2)	0.0350 (4)
H13	0.5618	0.0978	0.1757	0.042*
C14	0.49520 (7)	0.0515 (3)	0.2513 (2)	0.0338 (4)
H14	0.4890	−0.0876	0.2113	0.041*
C15	0.45962 (7)	0.1469 (3)	0.3345 (2)	0.0285 (4)
C16	0.41444 (7)	0.0333 (3)	0.3574 (2)	0.0317 (4)
H16	0.4074	−0.1050	0.3166	0.038*
C17	0.59290 (7)	0.5052 (4)	0.2540 (2)	0.0356 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0371 (7)	0.0478 (8)	0.0382 (6)	−0.0070 (6)	0.0207 (5)	−0.0074 (6)
O2	0.0352 (8)	0.0457 (9)	0.0632 (9)	−0.0036 (7)	0.0274 (7)	0.0042 (7)
O3	0.0498 (10)	0.0452 (10)	0.0917 (13)	−0.0172 (8)	0.0405 (9)	−0.0099 (8)
N1	0.0283 (8)	0.0505 (10)	0.0483 (9)	−0.0018 (7)	0.0197 (7)	−0.0032 (8)
N2	0.0312 (8)	0.0458 (10)	0.0353 (8)	−0.0097 (7)	0.0200 (6)	−0.0055 (7)
C1	0.0283 (9)	0.0382 (10)	0.0452 (10)	−0.0026 (8)	0.0166 (8)	−0.0032 (8)
C2	0.0282 (9)	0.0566 (14)	0.0485 (11)	−0.0062 (9)	0.0166 (8)	0.0062 (10)
C3	0.0375 (11)	0.0382 (11)	0.0551 (12)	−0.0114 (8)	0.0142 (9)	−0.0017 (9)
C4	0.0340 (10)	0.0398 (11)	0.0450 (10)	−0.0033 (7)	0.0156 (8)	−0.0053 (8)
C5	0.0232 (8)	0.0363 (10)	0.0334 (8)	−0.0031 (7)	0.0120 (6)	0.0016 (7)
C6	0.0252 (8)	0.0366 (9)	0.0318 (8)	−0.0011 (7)	0.0132 (6)	0.0023 (7)
C7	0.0255 (9)	0.0385 (11)	0.0308 (8)	−0.0060 (7)	0.0123 (6)	0.0013 (7)
C8	0.0332 (9)	0.0383 (10)	0.0348 (9)	−0.0001 (8)	0.0169 (7)	−0.0021 (7)
C9	0.0334 (10)	0.0317 (9)	0.0343 (8)	−0.0025 (7)	0.0149 (7)	−0.0030 (7)
C10	0.0267 (8)	0.0318 (9)	0.0285 (7)	−0.0003 (7)	0.0109 (6)	0.0021 (6)
C11	0.0281 (9)	0.0324 (9)	0.0337 (8)	−0.0057 (7)	0.0109 (7)	0.0004 (7)
C12	0.0244 (8)	0.0351 (10)	0.0357 (9)	−0.0022 (7)	0.0110 (7)	0.0052 (7)
C13	0.0295 (9)	0.0368 (10)	0.0429 (10)	0.0014 (7)	0.0171 (8)	0.0008 (8)
C14	0.0318 (10)	0.0324 (9)	0.0414 (10)	0.0003 (7)	0.0171 (8)	−0.0022 (7)
C15	0.0266 (9)	0.0331 (9)	0.0289 (7)	−0.0031 (7)	0.0124 (6)	0.0009 (6)
C16	0.0296 (9)	0.0336 (9)	0.0346 (9)	−0.0057 (7)	0.0130 (7)	−0.0013 (7)
C17	0.0256 (9)	0.0445 (12)	0.0392 (9)	−0.0064 (8)	0.0126 (7)	0.0031 (8)

Geometric parameters (Å, º) top

O1—C6	1.225 (2)	C7—C16	1.372 (3)
O2—C17	1.321 (2)	C7—C8	1.421 (3)
O2—H2O	0.84 (3)	C8—C9	1.365 (3)
O3—C17	1.200 (3)	C8—H8	0.9300
N1—C2	1.330 (3)	C9—C10	1.416 (2)
N1—C1	1.338 (2)	C9—H9	0.9300
N2—C6	1.347 (3)	C10—C11	1.414 (2)
N2—C7	1.422 (2)	C10—C15	1.420 (2)
N2—H2N	0.92 (3)	C11—C12	1.369 (3)
C1—C5	1.391 (2)	C11—H11	0.9300
C1—H1	0.9300	C12—C13	1.413 (3)
C2—C3	1.378 (3)	C12—C17	1.496 (2)
C2—H2	0.9300	C13—C14	1.365 (3)
C3—C4	1.384 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.420 (2)
C4—C5	1.389 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.418 (2)
C5—C6	1.497 (2)	C16—H16	0.9300

C17—O2—H2O	104 (2)	C7—C8—H8	120.0
C2—N1—C1	118.18 (17)	C8—C9—C10	120.97 (17)
C6—N2—C7	126.92 (15)	C8—C9—H9	119.5
C6—N2—H2N	120.2 (15)	C10—C9—H9	119.5
C7—N2—H2N	112.9 (15)	C11—C10—C9	122.43 (17)
N1—C1—C5	122.86 (18)	C11—C10—C15	118.87 (15)
N1—C1—H1	118.6	C9—C10—C15	118.69 (15)
C5—C1—H1	118.6	C12—C11—C10	120.79 (18)
N1—C2—C3	123.04 (18)	C12—C11—H11	119.6
N1—C2—H2	118.5	C10—C11—H11	119.6
C3—C2—H2	118.5	C11—C12—C13	120.25 (17)
C2—C3—C4	119.0 (2)	C11—C12—C17	118.50 (18)
C2—C3—H3	120.5	C13—C12—C17	121.19 (17)
C4—C3—H3	120.5	C14—C13—C12	120.39 (17)
C3—C4—C5	118.79 (18)	C14—C13—H13	119.8
C3—C4—H4	120.6	C12—C13—H13	119.8
C5—C4—H4	120.6	C13—C14—C15	120.52 (17)
C4—C5—C1	118.16 (16)	C13—C14—H14	119.7
C4—C5—C6	118.87 (16)	C15—C14—H14	119.7
C1—C5—C6	122.81 (16)	C16—C15—C10	119.90 (15)
O1—C6—N2	123.99 (16)	C16—C15—C14	120.97 (17)
O1—C6—C5	119.50 (17)	C10—C15—C14	119.13 (15)
N2—C6—C5	116.51 (15)	C7—C16—C15	119.58 (18)
C16—C7—C8	120.89 (16)	C7—C16—H16	120.2
C16—C7—N2	122.82 (17)	C15—C16—H16	120.2
C8—C7—N2	116.24 (16)	O3—C17—O2	123.64 (17)
C9—C8—C7	119.96 (16)	O3—C17—C12	123.26 (18)
C9—C8—H8	120.0	O2—C17—C12	113.08 (18)

C2—N1—C1—C5	−0.8 (3)	C9—C10—C11—C12	179.58 (16)
C1—N1—C2—C3	−0.2 (3)	C15—C10—C11—C12	−0.8 (3)
N1—C2—C3—C4	0.5 (3)	C10—C11—C12—C13	−1.2 (3)
C2—C3—C4—C5	0.3 (3)	C10—C11—C12—C17	176.03 (16)
C3—C4—C5—C1	−1.2 (3)	C11—C12—C13—C14	2.0 (3)
C3—C4—C5—C6	−176.77 (19)	C17—C12—C13—C14	−175.16 (19)
N1—C1—C5—C4	1.6 (3)	C12—C13—C14—C15	−0.7 (3)
N1—C1—C5—C6	176.89 (18)	C11—C10—C15—C16	−179.01 (19)
C7—N2—C6—O1	0.2 (3)	C9—C10—C15—C16	0.6 (2)
C7—N2—C6—C5	−178.98 (17)	C11—C10—C15—C14	2.0 (2)
C4—C5—C6—O1	23.5 (3)	C9—C10—C15—C14	−178.39 (19)
C1—C5—C6—O1	−151.76 (19)	C13—C14—C15—C16	179.77 (17)
C4—C5—C6—N2	−157.19 (18)	C13—C14—C15—C10	−1.2 (3)
C1—C5—C6—N2	27.5 (3)	C8—C7—C16—C15	−0.8 (3)
C6—N2—C7—C16	−26.4 (3)	N2—C7—C16—C15	−177.94 (16)
C6—N2—C7—C8	156.33 (19)	C10—C15—C16—C7	0.2 (3)
C16—C7—C8—C9	0.6 (3)	C14—C15—C16—C7	179.18 (17)
N2—C7—C8—C9	177.93 (17)	C11—C12—C17—O3	−6.6 (3)
C7—C8—C9—C10	0.2 (3)	C13—C12—C17—O3	170.6 (2)
C8—C9—C10—C11	178.80 (17)	C11—C12—C17—O2	174.43 (16)
C8—C9—C10—C15	−0.8 (3)	C13—C12—C17—O2	−8.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1ⁱ	0.92 (3)	2.01 (3)	2.926 (2)	170 (2)
O2—H2O···N1ⁱⁱ	0.84 (3)	1.88 (4)	2.708 (2)	170 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₂N₂O₃
M_r	292.29
Crystal system, space group	Monoclinic, Cc
Temperature (K)	296
a, b, c (Å)	25.901 (3), 6.2097 (7), 8.6080 (9)
β (°)	103.258 (9)
V (Å³)	1347.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.20 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.961, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	11725, 1693, 2845
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.671

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.05
No. of reflections	1693
No. of parameters	207
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.18
Absolute structure	The absolute structure could not be determined with certainty

Computer programs: APEX2 (Bruker (2008), SAINT (Bruker (2008), 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—H2N···O1ⁱ	0.92 (3)	2.01 (3)	2.926 (2)	170 (2)
O2—H2O···N1ⁱⁱ	0.84 (3)	1.88 (4)	2.708 (2)	170 (3)

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

Acknowledgements

This work was supported by the Mid-career Researcher Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science, and Technology (No. 2009–0079916).

References

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