1-Methyl-1H-indazole-3-carboxylic acid

Kang, S.; Wang, H.; Zhang, M.; Lu, R.; Wang, H.

doi:10.1107/S160053680803554X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2257

doi:10.1107/S160053680803554X

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1-Methyl-1H-indazole-3-carboxylic acid

Si-shun Kang,^a Hong-wei Wang,^b Min Zhang,^a Ran-zhe Lu ^a and Hai-bo Wang ^a ^*

^aCollege of Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and ^bNantong Entry–Exit Inspection and Quarantine Bureau, Nantong 226005, People's Republic of China
^*Correspondence e-mail: wanghaibo@njut.edu.cn

(Received 27 October 2008; accepted 30 October 2008; online 8 November 2008)

The asymmetric unit of the title compound, C₉H₈N₂O₂, contains two molecules. In the crystal structure, both molecules form inversion dimers via pairs of O—H⋯O hydrogen bonds, and a C—H⋯O interation is also seen.

Related literature

For the synthesis, see: Rousseau & Lindwall (1950 ).

Experimental

Crystal data

C₉H₈N₂O₂
M_r = 176.17
Monoclinic, P 2₁ /n
a = 7.5470 (15) Å
b = 14.873 (3) Å
c = 14.924 (3) Å
β = 93.10 (3)°
V = 1672.7 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.970, T_max = 0.990
3273 measured reflections
3032 independent reflections
1955 reflections with I > 2σ(I)
R_int = 0.0225
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.143
S = 1.00
3032 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.18 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
O2—H2A⋯O1ⁱ	0.82	1.82	2.632 (3)	173
O3—H3A⋯O4ⁱⁱ	0.82	1.82	2.619 (3)	164
C8—H8A⋯O1ⁱⁱⁱ	0.93	2.52	3.293 (4)	140
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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 global, I. DOI: 10.1107/S160053680803554X/hb2830sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803554X/hb2830Isup2.hkl

checkCIF report

Comment top

Methyl indazole carboxylic acid is an important pharmaceutical intermediate: many of its derivatives have biological activity and be used as a variety of drugs. We report here the crystal structure of the title compound, (I). There are O—H···O intermolecular H bonds in the structure between the hydrogencarboxylates forming the paired molecules that are situated on the crystallographic inversion centres (Table 1). The molecular structure of (I) is shown in Fig. 1.

Related literature top

For the synthesis, see: Rousseau & Lindwall (1950).

Experimental top

We prepared the title compound according to the literature method (Rousseau & Lindwall, 1950). Colourless blocks of (I) were obtained by slow evaporation of an petroleum/metanhol solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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. A view of the molecular structure of (I), showing displacement ellipsoids at the 30% probability level (arbitrary spheres for the H atoms).

1-Methyl-1H-indazole-3-carboxylic acid top

Crystal data top

C₉H₈N₂O₂	F(000) = 736
M_r = 176.17	D_x = 1.399 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 7.5470 (15) Å	θ = 9–13°
b = 14.873 (3) Å	µ = 0.10 mm⁻¹
c = 14.924 (3) Å	T = 293 K
β = 93.10 (3)°	Block, colorless
V = 1672.7 (6) Å³	0.30 × 0.20 × 0.10 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	1955 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 25.3°, θ_min = 1.9°
ω/2θ scans	h = −9→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→17
T_min = 0.970, T_max = 0.990	l = 0→17
3273 measured reflections	3 standard reflections every 200 reflections
3032 independent reflections	intensity decay: 1%

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.05P)² + 1.2P] where P = (F_o² + 2F_c²)/3
3032 reflections	(Δ/σ)_max = 0.007
237 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₉H₈N₂O₂	V = 1672.7 (6) Å³
M_r = 176.17	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.5470 (15) Å	µ = 0.10 mm⁻¹
b = 14.873 (3) Å	T = 293 K
c = 14.924 (3) Å	0.30 × 0.20 × 0.10 mm
β = 93.10 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1955 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.023
T_min = 0.970, T_max = 0.990	3 standard reflections every 200 reflections
3273 measured reflections	intensity decay: 1%
3032 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.00	Δρ_max = 0.18 e Å⁻³
3032 reflections	Δρ_min = −0.21 e Å⁻³
237 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
O1	−0.0113 (3)	0.38836 (12)	0.50834 (13)	0.0608 (6)
O2	0.0844 (3)	0.46943 (12)	0.39536 (13)	0.0627 (6)
H2A	0.0587	0.5109	0.4284	0.094*
N1	0.0777 (3)	0.17493 (14)	0.34517 (17)	0.0511 (6)
N2	0.0425 (3)	0.23313 (15)	0.41044 (16)	0.0491 (6)
C1	0.0605 (5)	0.07913 (19)	0.3588 (3)	0.0738 (10)
H1A	0.0634	0.0488	0.3021	0.111*
H1B	−0.0500	0.0667	0.3852	0.111*
H1C	0.1569	0.0583	0.3980	0.111*
C2	0.0474 (4)	0.39448 (17)	0.43217 (19)	0.0451 (7)
C3	0.0726 (3)	0.31492 (17)	0.37687 (17)	0.0402 (6)
C4	0.1346 (3)	0.31004 (17)	0.28951 (17)	0.0398 (6)
C5	0.1353 (3)	0.21700 (18)	0.27100 (19)	0.0444 (7)
C6	0.1899 (3)	0.37047 (19)	0.22478 (18)	0.0478 (7)
H6A	0.1896	0.4321	0.2355	0.057*
C7	0.2442 (4)	0.3372 (2)	0.1459 (2)	0.0593 (8)
H7A	0.2834	0.3769	0.1030	0.071*
C8	0.2429 (4)	0.2443 (2)	0.1273 (2)	0.0620 (9)
H8A	0.2790	0.2240	0.0722	0.074*
C9	0.1899 (4)	0.1841 (2)	0.1883 (2)	0.0604 (9)
H9A	0.1896	0.1228	0.1761	0.073*
O3	0.4920 (3)	0.38818 (12)	0.47829 (12)	0.0587 (6)
H3A	0.4752	0.4303	0.5122	0.088*
O4	0.5840 (3)	0.50052 (13)	0.39334 (14)	0.0655 (6)
N3	0.6825 (3)	0.30394 (16)	0.21444 (15)	0.0519 (6)
N4	0.6574 (3)	0.37909 (15)	0.26119 (15)	0.0474 (6)
C10	0.7390 (4)	0.3098 (2)	0.12273 (19)	0.0672 (9)
H10A	0.7340	0.2512	0.0957	0.101*
H10B	0.8584	0.3321	0.1234	0.101*
H10C	0.6618	0.3499	0.0887	0.101*
C11	0.5579 (3)	0.41736 (17)	0.40759 (18)	0.0433 (7)
C12	0.5990 (3)	0.35246 (17)	0.33950 (17)	0.0380 (6)
C13	0.5881 (3)	0.25681 (17)	0.34408 (18)	0.0406 (6)
C14	0.6464 (4)	0.22852 (19)	0.26155 (19)	0.0465 (7)
C15	0.6532 (4)	0.1370 (2)	0.2374 (2)	0.0616 (9)
H15A	0.6879	0.1192	0.1813	0.074*
C16	0.6078 (4)	0.0772 (2)	0.2984 (3)	0.0677 (10)
H16A	0.6139	0.0163	0.2849	0.081*
C17	0.5502 (4)	0.1039 (2)	0.3838 (2)	0.0669 (9)
H17A	0.5181	0.0600	0.4243	0.080*
C18	0.5410 (4)	0.19292 (18)	0.4077 (2)	0.0531 (7)
H18A	0.5050	0.2101	0.4638	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1022 (16)	0.0363 (11)	0.0479 (12)	−0.0076 (11)	0.0402 (11)	−0.0043 (9)
O2	0.1051 (18)	0.0305 (11)	0.0568 (12)	0.0012 (11)	0.0438 (12)	−0.0025 (9)
N1	0.0550 (15)	0.0271 (12)	0.0718 (17)	0.0010 (10)	0.0096 (12)	−0.0088 (11)
N2	0.0551 (15)	0.0355 (13)	0.0581 (15)	0.0028 (11)	0.0157 (12)	−0.0012 (11)
C1	0.081 (2)	0.0279 (16)	0.114 (3)	0.0007 (16)	0.016 (2)	0.0012 (17)
C2	0.0571 (18)	0.0305 (15)	0.0490 (16)	0.0005 (13)	0.0142 (13)	0.0002 (12)
C3	0.0432 (15)	0.0302 (14)	0.0486 (15)	−0.0013 (12)	0.0164 (12)	−0.0019 (12)
C4	0.0373 (14)	0.0384 (15)	0.0442 (15)	0.0003 (12)	0.0076 (11)	−0.0119 (12)
C5	0.0376 (14)	0.0370 (15)	0.0588 (17)	0.0082 (12)	0.0053 (13)	−0.0111 (13)
C6	0.0505 (17)	0.0407 (16)	0.0540 (17)	0.0059 (13)	0.0190 (13)	−0.0018 (13)
C7	0.063 (2)	0.067 (2)	0.0506 (18)	0.0077 (16)	0.0274 (15)	−0.0083 (15)
C8	0.0560 (19)	0.072 (2)	0.060 (2)	0.0090 (17)	0.0216 (16)	−0.0223 (18)
C9	0.0556 (19)	0.0517 (19)	0.074 (2)	0.0187 (15)	0.0041 (16)	−0.0255 (17)
O3	0.0938 (16)	0.0357 (11)	0.0498 (12)	0.0046 (10)	0.0348 (11)	−0.0029 (9)
O4	0.1026 (17)	0.0302 (11)	0.0684 (14)	−0.0035 (11)	0.0474 (12)	−0.0045 (10)
N3	0.0545 (15)	0.0510 (15)	0.0530 (14)	−0.0023 (12)	0.0282 (11)	−0.0153 (12)
N4	0.0506 (14)	0.0439 (14)	0.0497 (14)	0.0008 (11)	0.0214 (11)	−0.0049 (11)
C10	0.070 (2)	0.085 (3)	0.0489 (18)	−0.0068 (19)	0.0272 (16)	−0.0100 (17)
C11	0.0487 (16)	0.0323 (15)	0.0505 (16)	−0.0016 (12)	0.0189 (13)	−0.0036 (12)
C12	0.0395 (15)	0.0341 (14)	0.0414 (14)	0.0003 (12)	0.0104 (11)	−0.0038 (12)
C13	0.0370 (14)	0.0360 (15)	0.0497 (16)	0.0003 (12)	0.0120 (12)	−0.0085 (12)
C14	0.0406 (15)	0.0433 (16)	0.0567 (18)	0.0041 (13)	0.0130 (13)	−0.0134 (14)
C15	0.0557 (19)	0.050 (2)	0.080 (2)	0.0011 (15)	0.0145 (16)	−0.0312 (18)
C16	0.065 (2)	0.0334 (17)	0.104 (3)	0.0039 (15)	0.000 (2)	−0.0169 (18)
C17	0.071 (2)	0.0361 (18)	0.094 (3)	0.0008 (16)	0.0151 (19)	0.0054 (17)
C18	0.0606 (19)	0.0383 (16)	0.0621 (18)	0.0027 (14)	0.0183 (15)	0.0017 (14)

Geometric parameters (Å, º) top

O1—C2	1.246 (3)	O3—C11	1.267 (3)
O2—C2	1.280 (3)	O3—H3A	0.8200
O2—H2A	0.8200	O4—C11	1.272 (3)
N1—N2	1.340 (3)	N3—N4	1.337 (3)
N1—C5	1.363 (4)	N3—C14	1.359 (4)
N1—C1	1.446 (3)	N3—C10	1.458 (3)
N2—C3	1.340 (3)	N4—C12	1.331 (3)
C1—H1A	0.9600	C10—H10A	0.9600
C1—H1B	0.9600	C10—H10B	0.9600
C1—H1C	0.9600	C10—H10C	0.9600
C2—C3	1.461 (4)	C11—C12	1.447 (3)
C3—C4	1.411 (3)	C12—C13	1.427 (4)
C4—C6	1.400 (4)	C13—C14	1.395 (4)
C4—C5	1.411 (3)	C13—C18	1.402 (4)
C5—C9	1.410 (4)	C14—C15	1.409 (4)
C6—C7	1.361 (4)	C15—C16	1.331 (5)
C6—H6A	0.9300	C15—H15A	0.9300
C7—C8	1.409 (4)	C16—C17	1.425 (5)
C7—H7A	0.9300	C16—H16A	0.9300
C8—C9	1.353 (4)	C17—C18	1.374 (4)
C8—H8A	0.9300	C17—H17A	0.9300
C9—H9A	0.9300	C18—H18A	0.9300

C2—O2—H2A	109.5	C11—O3—H3A	109.5
N2—N1—C5	112.2 (2)	N4—N3—C14	112.5 (2)
N2—N1—C1	120.8 (3)	N4—N3—C10	119.8 (2)
C5—N1—C1	127.0 (3)	C14—N3—C10	127.7 (2)
C3—N2—N1	105.7 (2)	C12—N4—N3	105.8 (2)
N1—C1—H1A	109.5	N3—C10—H10A	109.5
N1—C1—H1B	109.5	N3—C10—H10B	109.5
H1A—C1—H1B	109.5	H10A—C10—H10B	109.5
N1—C1—H1C	109.5	N3—C10—H10C	109.5
H1A—C1—H1C	109.5	H10A—C10—H10C	109.5
H1B—C1—H1C	109.5	H10B—C10—H10C	109.5
O1—C2—O2	123.5 (2)	O3—C11—O4	122.9 (2)
O1—C2—C3	121.3 (2)	O3—C11—C12	117.7 (2)
O2—C2—C3	115.1 (2)	O4—C11—C12	119.3 (2)
N2—C3—C4	111.7 (2)	N4—C12—C13	111.2 (2)
N2—C3—C2	119.6 (2)	N4—C12—C11	120.8 (2)
C4—C3—C2	128.6 (2)	C13—C12—C11	128.0 (2)
C6—C4—C3	137.0 (2)	C14—C13—C18	119.8 (2)
C6—C4—C5	119.3 (2)	C14—C13—C12	103.7 (2)
C3—C4—C5	103.7 (2)	C18—C13—C12	136.5 (3)
N1—C5—C9	132.3 (3)	N3—C14—C13	106.8 (2)
N1—C5—C4	106.6 (2)	N3—C14—C15	130.8 (3)
C9—C5—C4	121.1 (3)	C13—C14—C15	122.3 (3)
C7—C6—C4	118.6 (3)	C16—C15—C14	117.2 (3)
C7—C6—H6A	120.7	C16—C15—H15A	121.4
C4—C6—H6A	120.7	C14—C15—H15A	121.4
C6—C7—C8	121.9 (3)	C15—C16—C17	121.8 (3)
C6—C7—H7A	119.1	C15—C16—H16A	119.1
C8—C7—H7A	119.1	C17—C16—H16A	119.1
C9—C8—C7	121.0 (3)	C18—C17—C16	121.5 (3)
C9—C8—H8A	119.5	C18—C17—H17A	119.2
C7—C8—H8A	119.5	C16—C17—H17A	119.2
C8—C9—C5	118.1 (3)	C17—C18—C13	117.3 (3)
C8—C9—H9A	121.0	C17—C18—H18A	121.3
C5—C9—H9A	121.0	C13—C18—H18A	121.3

C5—N1—N2—C3	1.9 (3)	C14—N3—N4—C12	−1.7 (3)
C1—N1—N2—C3	179.4 (3)	C10—N3—N4—C12	177.1 (2)
N1—N2—C3—C4	−2.2 (3)	N3—N4—C12—C13	0.8 (3)
N1—N2—C3—C2	−179.6 (2)	N3—N4—C12—C11	179.9 (2)
O1—C2—C3—N2	−4.2 (4)	O3—C11—C12—N4	175.5 (2)
O2—C2—C3—N2	178.0 (2)	O4—C11—C12—N4	−2.5 (4)
O1—C2—C3—C4	179.0 (3)	O3—C11—C12—C13	−5.5 (4)
O2—C2—C3—C4	1.1 (4)	O4—C11—C12—C13	176.5 (3)
N2—C3—C4—C6	−178.1 (3)	N4—C12—C13—C14	0.4 (3)
C2—C3—C4—C6	−1.0 (5)	C11—C12—C13—C14	−178.7 (3)
N2—C3—C4—C5	1.6 (3)	N4—C12—C13—C18	178.5 (3)
C2—C3—C4—C5	178.7 (3)	C11—C12—C13—C18	−0.6 (5)
N2—N1—C5—C9	178.6 (3)	N4—N3—C14—C13	2.0 (3)
C1—N1—C5—C9	1.4 (5)	C10—N3—C14—C13	−176.7 (3)
N2—N1—C5—C4	−1.0 (3)	N4—N3—C14—C15	179.1 (3)
C1—N1—C5—C4	−178.2 (3)	C10—N3—C14—C15	0.4 (5)
C6—C4—C5—N1	179.4 (2)	C18—C13—C14—N3	−179.9 (2)
C3—C4—C5—N1	−0.4 (3)	C12—C13—C14—N3	−1.4 (3)
C6—C4—C5—C9	−0.3 (4)	C18—C13—C14—C15	2.7 (4)
C3—C4—C5—C9	179.9 (2)	C12—C13—C14—C15	−178.8 (3)
C3—C4—C6—C7	179.1 (3)	N3—C14—C15—C16	−179.3 (3)
C5—C4—C6—C7	−0.5 (4)	C13—C14—C15—C16	−2.6 (4)
C4—C6—C7—C8	1.2 (4)	C14—C15—C16—C17	1.6 (5)
C6—C7—C8—C9	−1.1 (5)	C15—C16—C17—C18	−0.9 (5)
C7—C8—C9—C5	0.3 (5)	C16—C17—C18—C13	0.9 (5)
N1—C5—C9—C8	−179.2 (3)	C14—C13—C18—C17	−1.8 (4)
C4—C5—C9—C8	0.4 (4)	C12—C13—C18—C17	−179.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1ⁱ	0.82	1.82	2.632 (3)	173
O3—H3A···O4ⁱⁱ	0.82	1.82	2.619 (3)	164
C8—H8A···O1ⁱⁱⁱ	0.93	2.52	3.293 (4)	140

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

Experimental details

Crystal data
Chemical formula	C₉H₈N₂O₂
M_r	176.17
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.5470 (15), 14.873 (3), 14.924 (3)
β (°)	93.10 (3)
V (Å³)	1672.7 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.970, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	3273, 3032, 1955
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.143, 1.00
No. of reflections	3032
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.21

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), 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
O2—H2A···O1ⁱ	0.82	1.82	2.632 (3)	173
O3—H3A···O4ⁱⁱ	0.82	1.82	2.619 (3)	164
C8—H8A···O1ⁱⁱⁱ	0.93	2.52	3.293 (4)	140

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

References

Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Rousseau, V. & Lindwall, H. G. (1950). J. Am. Chem. Soc. 72, 3047–3051. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2257

doi:10.1107/S160053680803554X

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