4-(3-Fluoro-4-methyl-anilino)-2-methyl-idene-4-oxo-butanoic acid.

The title compound, C12H12FNO3, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. The dihedral angle between the mean planes of the 3-fluoro-4-methyl-phenyl ring and the oxo-amine group is 25.7 (7)° in mol-ecule A and 71.3 (7)° in mol-ecule B, while the mean plane of the 2-methyl-idene-4-oxo-butanoic acid group is twisted by 76.2 (1)° from that of the oxo-amine group in mol-ecule A and by 76.2 (4)° in mol-ecule B. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds [the latter forming an R 2 (2)(8) graph-set motif] link the mol-ecules into a two-dimensional network parallel to the ac plane.

Related literature

For properties of itaconic anhydride polymers, see: Oishi (1980 ▶); Urzua et al. (1998 ▶). For derivatives of itaconic anhydride, see: Katla et al. (2011 ▶); Shetgiri & Nayak (2005 ▶); Hanoon (2011 ▶); Nayak et al. (2013 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H12FNO3

M = 237.23

Triclinic,

a = 6.3368 (3) Å

b = 8.2642 (4) Å

c = 21.0277 (11) Å

α = 84.057 (4)°

β = 89.798 (4)°

γ = 86.062 (4)°

V = 1092.69 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 173 K

0.38 × 0.32 × 0.16 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.673, T max = 1.000

13094 measured reflections

7221 independent reflections

4872 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.221

S = 1.06

7221 reflections

327 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.68 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S160053681302998X/bv2227sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302998X/bv2227Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681302998X/bv2227Isup3.cml

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

C12H12FNO3	Z = 4
Mr = 237.23	F(000) = 496
Triclinic, P1	Dx = 1.442 Mg m−3
a = 6.3368 (3) Å	Mo Kα radiation, λ = 0.7107 Å
b = 8.2642 (4) Å	Cell parameters from 3167 reflections
c = 21.0277 (11) Å	θ = 3.3–32.7°
α = 84.057 (4)°	µ = 0.12 mm−1
β = 89.798 (4)°	T = 173 K
γ = 86.062 (4)°	Irregular, colourless
V = 1092.69 (9) Å3	0.38 × 0.32 × 0.16 mm

Agilent Xcalibur (Eos, Gemini) diffractometer	7221 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4872 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 16.0416 pixels mm-1	θmax = 32.8°, θmin = 3.3°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −11→12
Tmin = 0.673, Tmax = 1.000	l = −30→31
13094 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.081	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.221	w = 1/[σ2(Fo2) + (0.0895P)2 + 0.6971P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
7221 reflections	Δρmax = 0.68 e Å−3
327 parameters	Δρmin = −0.28 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
F1A	0.2264 (3)	0.7138 (2)	0.08603 (8)	0.0598 (5)
O1A	−0.0578 (3)	0.49102 (19)	0.28774 (8)	0.0317 (4)
O2A	−0.2598 (3)	0.4663 (2)	0.46934 (8)	0.0326 (4)
H2A	−0.1978	0.5069	0.4973	0.049*
O3A	0.0704 (2)	0.3813 (2)	0.44375 (8)	0.0301 (3)
N1A	0.1954 (3)	0.3003 (2)	0.26309 (9)	0.0267 (4)
H1A	0.2466	0.2026	0.2745	0.032*
C1A	0.0240 (3)	0.3514 (2)	0.29537 (9)	0.0223 (4)
C2A	−0.0635 (3)	0.2194 (2)	0.34215 (10)	0.0253 (4)
H2AA	−0.1345	0.1443	0.3184	0.030*
H2AB	0.0528	0.1584	0.3656	0.030*
C3A	−0.2160 (3)	0.2886 (2)	0.38861 (10)	0.0239 (4)
C4A	−0.1221 (3)	0.3827 (2)	0.43641 (10)	0.0236 (4)
C5A	−0.4195 (4)	0.2636 (3)	0.38952 (12)	0.0324 (5)
H5AA	−0.518 (5)	0.312 (4)	0.4188 (14)	0.038 (8)*
H5AB	−0.483 (5)	0.204 (4)	0.3585 (15)	0.049 (9)*
C6A	0.3022 (4)	0.3877 (3)	0.21259 (10)	0.0266 (4)
C7A	0.2073 (4)	0.5190 (3)	0.17415 (11)	0.0310 (5)
H7A	0.0701	0.5593	0.1820	0.037*
C8A	0.3231 (4)	0.5879 (3)	0.12384 (11)	0.0349 (5)
C9A	0.5269 (4)	0.5377 (3)	0.10906 (12)	0.0351 (5)
C10A	0.6179 (4)	0.4087 (3)	0.14927 (13)	0.0388 (6)
H10A	0.7570	0.3716	0.1421	0.047*
C11A	0.5091 (4)	0.3328 (3)	0.19983 (12)	0.0337 (5)
H11A	0.5743	0.2450	0.2253	0.040*
C12A	0.6457 (5)	0.6181 (4)	0.05352 (13)	0.0477 (7)
H12D	0.5574	0.7058	0.0320	0.072*
H12E	0.6843	0.5394	0.0242	0.072*
H12F	0.7712	0.6602	0.0689	0.072*
F1B	0.6414 (3)	1.0662 (3)	0.05324 (7)	0.0555 (5)
O1B	0.4220 (3)	0.97672 (18)	0.28923 (8)	0.0288 (3)
O2B	0.2374 (3)	0.9727 (2)	0.47086 (8)	0.0350 (4)
H2B	0.3050	1.0169	0.4965	0.053*
O3B	0.5598 (2)	0.8739 (2)	0.44475 (8)	0.0318 (4)
N1B	0.6529 (3)	0.7751 (2)	0.26178 (9)	0.0278 (4)
H1B	0.6969	0.6743	0.2696	0.033*
C1B	0.4934 (3)	0.8347 (2)	0.29677 (9)	0.0214 (4)
C2B	0.4038 (3)	0.7091 (2)	0.34588 (10)	0.0248 (4)
H2BA	0.3250	0.6348	0.3240	0.030*
H2BB	0.5194	0.6460	0.3689	0.030*
C3B	0.2614 (3)	0.7880 (2)	0.39254 (9)	0.0234 (4)
C4B	0.3671 (3)	0.8823 (2)	0.43834 (9)	0.0233 (4)
C5B	0.0546 (4)	0.7733 (3)	0.39513 (12)	0.0321 (5)
H5BA	−0.030 (4)	0.831 (3)	0.4239 (12)	0.029 (7)*
H5BB	−0.013 (5)	0.715 (4)	0.3643 (14)	0.040 (8)*
C6B	0.7520 (3)	0.8736 (3)	0.21197 (10)	0.0260 (4)
C7B	0.6465 (4)	0.9236 (3)	0.15526 (11)	0.0304 (5)
H7B	0.5093	0.8950	0.1489	0.036*
C8B	0.7488 (4)	1.0169 (3)	0.10828 (11)	0.0334 (5)
C9B	0.9529 (4)	1.0626 (3)	0.11392 (11)	0.0324 (5)
C10B	1.0547 (4)	1.0105 (3)	0.17149 (11)	0.0340 (5)
H10B	1.1919	1.0394	0.1776	0.041*
C11B	0.9578 (4)	0.9164 (3)	0.22030 (11)	0.0308 (5)
H11B	1.0301	0.8823	0.2583	0.037*
C12B	1.0594 (5)	1.1636 (4)	0.06094 (13)	0.0466 (7)
H12A	1.1739	1.2156	0.0783	0.070*
H12B	0.9588	1.2452	0.0410	0.070*
H12C	1.1134	1.0945	0.0298	0.070*

	U11	U22	U33	U12	U13	U23
F1A	0.0641 (12)	0.0530 (11)	0.0554 (10)	0.0053 (9)	0.0081 (9)	0.0204 (8)
O1A	0.0349 (9)	0.0197 (7)	0.0393 (9)	0.0029 (6)	0.0068 (7)	−0.0007 (6)
O2A	0.0261 (8)	0.0356 (9)	0.0384 (9)	−0.0011 (7)	0.0009 (6)	−0.0149 (7)
O3A	0.0242 (7)	0.0300 (8)	0.0383 (8)	−0.0041 (6)	0.0013 (6)	−0.0117 (6)
N1A	0.0288 (9)	0.0183 (8)	0.0324 (9)	−0.0005 (7)	0.0039 (7)	−0.0003 (6)
C1A	0.0234 (9)	0.0184 (8)	0.0256 (9)	−0.0015 (7)	−0.0016 (7)	−0.0034 (7)
C2A	0.0303 (10)	0.0161 (8)	0.0302 (10)	−0.0043 (8)	0.0005 (8)	−0.0038 (7)
C3A	0.0266 (10)	0.0186 (9)	0.0265 (9)	−0.0041 (8)	0.0001 (7)	−0.0007 (7)
C4A	0.0237 (9)	0.0189 (9)	0.0283 (9)	−0.0047 (7)	0.0022 (7)	−0.0013 (7)
C5A	0.0280 (11)	0.0319 (12)	0.0382 (12)	−0.0088 (9)	−0.0004 (9)	−0.0038 (9)
C6A	0.0293 (10)	0.0216 (9)	0.0297 (10)	−0.0051 (8)	0.0033 (8)	−0.0043 (7)
C7A	0.0321 (11)	0.0267 (10)	0.0339 (11)	−0.0020 (9)	0.0025 (9)	−0.0014 (8)
C8A	0.0440 (13)	0.0257 (11)	0.0343 (11)	−0.0052 (10)	0.0028 (10)	0.0013 (8)
C9A	0.0435 (13)	0.0271 (11)	0.0371 (12)	−0.0141 (10)	0.0096 (10)	−0.0065 (9)
C10A	0.0326 (12)	0.0346 (13)	0.0500 (14)	−0.0060 (10)	0.0117 (10)	−0.0057 (10)
C11A	0.0297 (11)	0.0284 (11)	0.0419 (12)	0.0001 (9)	0.0045 (9)	−0.0008 (9)
C12A	0.0585 (18)	0.0435 (15)	0.0430 (14)	−0.0181 (14)	0.0184 (12)	−0.0042 (11)
F1B	0.0517 (10)	0.0758 (13)	0.0364 (8)	−0.0110 (9)	−0.0070 (7)	0.0112 (8)
O1B	0.0296 (8)	0.0180 (7)	0.0375 (8)	0.0016 (6)	0.0067 (6)	0.0003 (6)
O2B	0.0248 (8)	0.0406 (10)	0.0422 (9)	−0.0002 (7)	0.0010 (6)	−0.0179 (7)
O3B	0.0226 (7)	0.0340 (9)	0.0409 (9)	−0.0035 (7)	0.0012 (6)	−0.0128 (7)
N1B	0.0279 (9)	0.0180 (8)	0.0365 (9)	0.0020 (7)	0.0068 (7)	−0.0007 (7)
C1B	0.0204 (9)	0.0186 (8)	0.0257 (9)	−0.0022 (7)	−0.0005 (7)	−0.0030 (7)
C2B	0.0285 (10)	0.0147 (8)	0.0315 (10)	−0.0045 (7)	0.0014 (8)	−0.0022 (7)
C3B	0.0253 (9)	0.0186 (9)	0.0261 (9)	−0.0044 (7)	0.0011 (7)	0.0009 (7)
C4B	0.0225 (9)	0.0205 (9)	0.0266 (9)	−0.0030 (7)	0.0024 (7)	−0.0009 (7)
C5B	0.0267 (11)	0.0346 (12)	0.0347 (11)	−0.0075 (9)	0.0008 (9)	0.0011 (9)
C6B	0.0254 (10)	0.0198 (9)	0.0330 (10)	−0.0007 (8)	0.0066 (8)	−0.0039 (7)
C7B	0.0242 (10)	0.0325 (11)	0.0355 (11)	−0.0059 (9)	0.0028 (8)	−0.0062 (9)
C8B	0.0347 (12)	0.0347 (12)	0.0304 (11)	−0.0019 (10)	0.0005 (9)	−0.0022 (9)
C9B	0.0342 (12)	0.0278 (11)	0.0362 (11)	−0.0049 (9)	0.0100 (9)	−0.0066 (9)
C10B	0.0282 (11)	0.0374 (13)	0.0384 (12)	−0.0102 (10)	0.0048 (9)	−0.0085 (9)
C11B	0.0263 (10)	0.0321 (11)	0.0345 (11)	−0.0037 (9)	0.0001 (8)	−0.0041 (9)
C12B	0.0529 (16)	0.0426 (15)	0.0451 (14)	−0.0156 (13)	0.0182 (12)	−0.0012 (11)

F1A—C8A	1.355 (3)	F1B—C8B	1.356 (3)
O1A—C1A	1.228 (2)	O1B—C1B	1.223 (2)
O2A—H2A	0.8200	O2B—H2B	0.8200
O2A—C4A	1.315 (2)	O2B—C4B	1.311 (2)
O3A—C4A	1.229 (3)	O3B—C4B	1.225 (2)
N1A—H1A	0.8600	N1B—H1B	0.8600
N1A—C1A	1.345 (3)	N1B—C1B	1.344 (2)
N1A—C6A	1.418 (3)	N1B—C6B	1.429 (3)
C1A—C2A	1.524 (3)	C1B—C2B	1.523 (3)
C2A—H2AA	0.9700	C2B—H2BA	0.9700
C2A—H2AB	0.9700	C2B—H2BB	0.9700
C2A—C3A	1.500 (3)	C2B—C3B	1.499 (3)
C3A—C4A	1.483 (3)	C3B—C4B	1.488 (3)
C3A—C5A	1.320 (3)	C3B—C5B	1.325 (3)
C5A—H5AA	0.97 (3)	C5B—H5BA	0.95 (3)
C5A—H5AB	0.97 (3)	C5B—H5BB	0.96 (3)
C6A—C7A	1.387 (3)	C6B—C7B	1.380 (3)
C6A—C11A	1.392 (3)	C6B—C11B	1.391 (3)
C7A—H7A	0.9300	C7B—H7B	0.9300
C7A—C8A	1.382 (3)	C7B—C8B	1.377 (3)
C8A—C9A	1.373 (4)	C8B—C9B	1.381 (3)
C9A—C10A	1.385 (4)	C9B—C10B	1.388 (3)
C9A—C12A	1.508 (3)	C9B—C12B	1.508 (3)
C10A—H10A	0.9300	C10B—H10B	0.9300
C10A—C11A	1.384 (3)	C10B—C11B	1.389 (3)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—H12D	0.9600	C12B—H12A	0.9600
C12A—H12E	0.9600	C12B—H12B	0.9600
C12A—H12F	0.9600	C12B—H12C	0.9600
C4A—O2A—H2A	109.5	C4B—O2B—H2B	109.5
C1A—N1A—H1A	116.0	C1B—N1B—H1B	118.9
C1A—N1A—C6A	128.04 (17)	C1B—N1B—C6B	122.27 (17)
C6A—N1A—H1A	116.0	C6B—N1B—H1B	118.9
O1A—C1A—N1A	123.59 (19)	O1B—C1B—N1B	123.28 (18)
O1A—C1A—C2A	122.32 (18)	O1B—C1B—C2B	122.36 (17)
N1A—C1A—C2A	114.09 (17)	N1B—C1B—C2B	114.34 (17)
C1A—C2A—H2AA	109.1	C1B—C2B—H2BA	109.3
C1A—C2A—H2AB	109.1	C1B—C2B—H2BB	109.3
H2AA—C2A—H2AB	107.9	H2BA—C2B—H2BB	107.9
C3A—C2A—C1A	112.28 (16)	C3B—C2B—C1B	111.76 (16)
C3A—C2A—H2AA	109.1	C3B—C2B—H2BA	109.3
C3A—C2A—H2AB	109.1	C3B—C2B—H2BB	109.3
C4A—C3A—C2A	115.60 (18)	C4B—C3B—C2B	115.88 (18)
C5A—C3A—C2A	123.3 (2)	C5B—C3B—C2B	123.4 (2)
C5A—C3A—C4A	121.1 (2)	C5B—C3B—C4B	120.7 (2)
O2A—C4A—C3A	114.93 (18)	O2B—C4B—C3B	114.48 (18)
O3A—C4A—O2A	123.6 (2)	O3B—C4B—O2B	123.6 (2)
O3A—C4A—C3A	121.48 (19)	O3B—C4B—C3B	121.93 (18)
C3A—C5A—H5AA	122.7 (18)	C3B—C5B—H5BA	119.9 (17)
C3A—C5A—H5AB	122.1 (19)	C3B—C5B—H5BB	120.1 (18)
H5AA—C5A—H5AB	115 (3)	H5BA—C5B—H5BB	120 (2)
C7A—C6A—N1A	123.2 (2)	C7B—C6B—N1B	120.5 (2)
C7A—C6A—C11A	119.2 (2)	C7B—C6B—C11B	119.9 (2)
C11A—C6A—N1A	117.53 (19)	C11B—C6B—N1B	119.6 (2)
C6A—C7A—H7A	121.1	C6B—C7B—H7B	120.7
C8A—C7A—C6A	117.9 (2)	C8B—C7B—C6B	118.5 (2)
C8A—C7A—H7A	121.1	C8B—C7B—H7B	120.7
F1A—C8A—C7A	117.0 (2)	F1B—C8B—C7B	117.6 (2)
F1A—C8A—C9A	117.8 (2)	F1B—C8B—C9B	118.4 (2)
C9A—C8A—C7A	125.1 (2)	C7B—C8B—C9B	124.0 (2)
C8A—C9A—C10A	115.3 (2)	C8B—C9B—C10B	116.0 (2)
C8A—C9A—C12A	122.7 (2)	C8B—C9B—C12B	122.2 (2)
C10A—C9A—C12A	121.9 (2)	C10B—C9B—C12B	121.8 (2)
C9A—C10A—H10A	118.9	C9B—C10B—H10B	119.0
C11A—C10A—C9A	122.3 (2)	C9B—C10B—C11B	122.0 (2)
C11A—C10A—H10A	118.9	C11B—C10B—H10B	119.0
C6A—C11A—H11A	119.9	C6B—C11B—H11B	120.2
C10A—C11A—C6A	120.1 (2)	C10B—C11B—C6B	119.5 (2)
C10A—C11A—H11A	119.9	C10B—C11B—H11B	120.2
C9A—C12A—H12D	109.5	C9B—C12B—H12A	109.5
C9A—C12A—H12E	109.5	C9B—C12B—H12B	109.5
C9A—C12A—H12F	109.5	C9B—C12B—H12C	109.5
H12D—C12A—H12E	109.5	H12A—C12B—H12B	109.5
H12D—C12A—H12F	109.5	H12A—C12B—H12C	109.5
H12E—C12A—H12F	109.5	H12B—C12B—H12C	109.5
F1A—C8A—C9A—C10A	−180.0 (2)	F1B—C8B—C9B—C10B	179.3 (2)
F1A—C8A—C9A—C12A	0.7 (4)	F1B—C8B—C9B—C12B	−0.5 (4)
O1A—C1A—C2A—C3A	−15.6 (3)	O1B—C1B—C2B—C3B	−13.9 (3)
N1A—C1A—C2A—C3A	165.26 (18)	N1B—C1B—C2B—C3B	167.55 (19)
N1A—C6A—C7A—C8A	−175.9 (2)	N1B—C6B—C7B—C8B	−179.3 (2)
N1A—C6A—C11A—C10A	177.1 (2)	N1B—C6B—C11B—C10B	179.2 (2)
C1A—N1A—C6A—C7A	−22.6 (4)	C1B—N1B—C6B—C7B	−71.6 (3)
C1A—N1A—C6A—C11A	160.4 (2)	C1B—N1B—C6B—C11B	109.7 (2)
C1A—C2A—C3A—C4A	−69.2 (2)	C1B—C2B—C3B—C4B	−69.6 (2)
C1A—C2A—C3A—C5A	113.4 (2)	C1B—C2B—C3B—C5B	112.1 (2)
C2A—C3A—C4A—O2A	168.57 (17)	C2B—C3B—C4B—O2B	168.70 (17)
C2A—C3A—C4A—O3A	−11.3 (3)	C2B—C3B—C4B—O3B	−11.7 (3)
C5A—C3A—C4A—O2A	−14.0 (3)	C5B—C3B—C4B—O2B	−13.0 (3)
C5A—C3A—C4A—O3A	166.2 (2)	C5B—C3B—C4B—O3B	166.6 (2)
C6A—N1A—C1A—O1A	−5.3 (4)	C6B—N1B—C1B—O1B	−0.6 (3)
C6A—N1A—C1A—C2A	173.9 (2)	C6B—N1B—C1B—C2B	177.90 (19)
C6A—C7A—C8A—F1A	178.7 (2)	C6B—C7B—C8B—F1B	−179.3 (2)
C6A—C7A—C8A—C9A	−0.7 (4)	C6B—C7B—C8B—C9B	0.8 (4)
C7A—C6A—C11A—C10A	−0.1 (4)	C7B—C6B—C11B—C10B	0.5 (3)
C7A—C8A—C9A—C10A	−0.6 (4)	C7B—C8B—C9B—C10B	−0.7 (4)
C7A—C8A—C9A—C12A	−179.9 (3)	C7B—C8B—C9B—C12B	179.4 (2)
C8A—C9A—C10A—C11A	1.6 (4)	C8B—C9B—C10B—C11B	0.6 (4)
C9A—C10A—C11A—C6A	−1.3 (4)	C9B—C10B—C11B—C6B	−0.6 (4)
C11A—C6A—C7A—C8A	1.0 (4)	C11B—C6B—C7B—C8B	−0.6 (3)
C12A—C9A—C10A—C11A	−179.1 (3)	C12B—C9B—C10B—C11B	−179.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2A···O3Ai	0.82	1.84	2.658 (2)	174
O2B—H2B···O3Bii	0.82	1.85	2.667 (2)	176
N1A—H1A···O1Biii	0.86	2.10	2.948 (2)	168
N1B—H1B···O1Aiv	0.86	2.10	2.884 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2A—H2A⋯O3A i	0.82	1.84	2.658 (2)	174
O2B—H2B⋯O3B ii	0.82	1.85	2.667 (2)	176
N1A—H1A⋯O1B iii	0.86	2.10	2.948 (2)	168
N1B—H1B⋯O1A iv	0.86	2.10	2.884 (2)	151

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