2-Amino-5-bromo-pyridine-4-hy-droxy-benzoic acid (1/1).

The title 1:1 adduct, C(5)H(5)BrN(2)·C(7)H(6)O(3), contains two mol-ecules of each species in the asymmetric unit, with similar geometries. In the crystal, mol-ecules are linked to form extended chains along [100] by N-H⋯O, O-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds. Adjacent chains are crosslinked via further N-H⋯O inter-actions into sheets lying parallel to (001). The crystal studied was an inversion twin with a 0.54 (2):0.46 (2) domain ratio.

Related literature

For substituted pyridines, see: Pozharski et al. (1997 ▶); Katritzky et al. (1996 ▶). For details of hydrogen bonding, see: Scheiner (1997 ▶); Jeffrey & Saenger (1991 ▶); Jeffrey (1997 ▶). For 4-hy­droxy­benzoic acid, see: Vishweshwar et al. (2003 ▶). For related structures, see: Hemamalini & Fun (2010a ▶,b ▶,c ▶); Quah et al. (2008a ▶,b ▶, 2010 ▶). For reference bond lengths, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C5H5BrN2·C7H6O3

M = 311.14

Orthorhombic,

a = 21.370 (12) Å

b = 3.990 (2) Å

c = 28.939 (15) Å

V = 2467 (2) Å3

Z = 8

Mo Kα radiation

μ = 3.33 mm−1

T = 100 K

0.29 × 0.12 × 0.09 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.449, T max = 0.763

6994 measured reflections

3770 independent reflections

2994 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.148

S = 1.10

3770 reflections

296 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.99 e Å−3

Absolute structure: Flack (1983 ▶), 1554 Friedel pairs

Flack parameter: 0.54 (2)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT ; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025924/hb5539sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025924/hb5539Isup2.hkl

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

C5H5BrN2·C7H6O3	F(000) = 1248
Mr = 311.14	Dx = 1.675 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1665 reflections
a = 21.370 (12) Å	θ = 2.4–25.0°
b = 3.990 (2) Å	µ = 3.33 mm−1
c = 28.939 (15) Å	T = 100 K
V = 2467 (2) Å3	Needle, brown
Z = 8	0.29 × 0.12 × 0.09 mm

Bruker SMART APEXII DUO CCD diffractometer	3770 independent reflections
Radiation source: fine-focus sealed tube	2994 reflections with I > 2σ(I)
graphite	Rint = 0.051
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −25→19
Tmin = 0.449, Tmax = 0.763	k = −4→4
6994 measured reflections	l = −30→34

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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.148	w = 1/[σ2(Fo2) + (0.0538P)2 + 9.0399P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
3770 reflections	Δρmax = 0.72 e Å−3
296 parameters	Δρmin = −0.99 e Å−3
1 restraint	Absolute structure: Flack (1983), 1554 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.54 (2)

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
Br1A	0.00906 (6)	0.7888 (2)	0.30916 (3)	0.0442 (3)
N1A	−0.0212 (3)	0.348 (2)	0.4357 (3)	0.0213 (18)
N2A	0.0361 (4)	0.2594 (19)	0.5015 (3)	0.0281 (18)
H2AA	0.0040	0.1584	0.5127	0.034*
H2AB	0.0697	0.2776	0.5177	0.034*
C1A	−0.0273 (5)	0.469 (2)	0.3934 (3)	0.0262 (14)
H1AA	−0.0657	0.4460	0.3787	0.031*
C2A	0.0212 (5)	0.628 (2)	0.3699 (3)	0.0265 (15)
C3A	0.0794 (5)	0.672 (2)	0.3928 (3)	0.0265 (15)
H3AA	0.1132	0.7740	0.3782	0.032*
C4A	0.0836 (4)	0.556 (2)	0.4369 (3)	0.021 (2)
H4AA	0.1206	0.5890	0.4532	0.026*
C5A	0.0338 (4)	0.389 (2)	0.4585 (3)	0.020 (2)
Br1B	0.25717 (6)	0.3515 (2)	0.37657 (4)	0.0456 (3)
N1B	0.2861 (4)	−0.067 (2)	0.2491 (3)	0.0265 (19)
N2B	0.2263 (4)	−0.178 (2)	0.1857 (3)	0.030 (2)
H2BA	0.2591	−0.2604	0.1728	0.036*
H2BB	0.1912	−0.1760	0.1711	0.036*
C1B	0.2925 (5)	0.049 (2)	0.2930 (3)	0.0262 (14)
H1BA	0.3312	0.0346	0.3075	0.031*
C2B	0.2442 (5)	0.183 (2)	0.3155 (4)	0.0276 (16)
C3B	0.1851 (5)	0.196 (2)	0.2964 (3)	0.0276 (16)
H3BA	0.1514	0.2832	0.3129	0.033*
C4B	0.1773 (4)	0.076 (2)	0.2513 (3)	0.022 (2)
H4BA	0.1383	0.0822	0.2370	0.027*
C5B	0.2297 (4)	−0.056 (2)	0.2280 (3)	0.021 (2)
O1A	0.6515 (3)	0.3077 (15)	0.5579 (2)	0.0242 (15)
H1AB	0.6471	0.3109	0.5860	0.036*
O2A	0.8817 (3)	1.0048 (16)	0.4626 (2)	0.0225 (14)
H2AC	0.9144	1.1065	0.4579	0.034*
O3A	0.9066 (3)	1.1204 (15)	0.5362 (2)	0.0234 (14)
C6A	0.7754 (4)	0.662 (2)	0.4870 (3)	0.018 (2)
H6A	0.7868	0.6712	0.4561	0.022*
C7A	0.7202 (4)	0.498 (2)	0.5000 (3)	0.023 (2)
H7A	0.6947	0.3996	0.4777	0.027*
C8A	0.7043 (4)	0.483 (2)	0.5461 (3)	0.0195 (13)
C9A	0.7426 (4)	0.634 (2)	0.5785 (3)	0.0179 (14)
H9A	0.7311	0.6283	0.6094	0.022*
C10A	0.7957 (4)	0.789 (2)	0.5664 (3)	0.017 (2)
H10A	0.8212	0.8811	0.5892	0.020*
C11A	0.8133 (4)	0.813 (2)	0.5202 (3)	0.0180 (19)
C12A	0.8711 (4)	0.990 (2)	0.5070 (3)	0.020 (2)
O1B	0.6068 (3)	−0.1993 (15)	0.1278 (2)	0.0235 (14)
H1BB	0.6039	−0.2558	0.1006	0.035*
O2B	0.3859 (3)	0.5786 (15)	0.2236 (2)	0.0235 (14)
H2BC	0.3541	0.6888	0.2282	0.035*
O3B	0.3558 (3)	0.6584 (16)	0.1505 (2)	0.0215 (14)
C6B	0.4619 (4)	0.286 (2)	0.1194 (3)	0.023 (2)
H6B	0.4350	0.3680	0.0968	0.027*
C7B	0.5150 (4)	0.105 (2)	0.1061 (4)	0.023 (2)
H7B	0.5234	0.0653	0.0750	0.028*
C8B	0.5547 (4)	−0.0131 (19)	0.1401 (3)	0.0195 (13)
C9B	0.5417 (4)	0.031 (2)	0.1864 (3)	0.0179 (14)
H8B	0.5680	−0.0607	0.2086	0.022*
C10B	0.4906 (4)	0.210 (2)	0.1995 (3)	0.022 (2)
H10B	0.4828	0.2442	0.2307	0.026*
C11B	0.4487 (4)	0.345 (2)	0.1661 (3)	0.0134 (18)
C12B	0.3937 (4)	0.539 (2)	0.1789 (3)	0.017 (2)

	U11	U22	U33	U12	U13	U23
Br1A	0.0924 (9)	0.0243 (4)	0.0159 (5)	−0.0036 (5)	0.0007 (7)	0.0058 (6)
N1A	0.023 (4)	0.025 (4)	0.016 (4)	−0.004 (3)	−0.001 (3)	0.001 (4)
N2A	0.040 (5)	0.029 (4)	0.016 (4)	−0.003 (4)	−0.001 (4)	−0.003 (3)
C1A	0.037 (4)	0.029 (3)	0.013 (3)	0.003 (3)	−0.002 (3)	0.002 (3)
C2A	0.051 (4)	0.014 (3)	0.014 (4)	0.002 (3)	0.008 (3)	0.007 (3)
C3A	0.051 (4)	0.014 (3)	0.014 (4)	0.002 (3)	0.008 (3)	0.007 (3)
C4A	0.030 (5)	0.013 (4)	0.021 (5)	0.000 (4)	0.009 (4)	0.003 (4)
C5A	0.027 (6)	0.012 (4)	0.020 (5)	−0.003 (4)	−0.002 (4)	0.000 (4)
Br1B	0.0919 (10)	0.0266 (5)	0.0183 (5)	0.0062 (5)	0.0027 (6)	−0.0037 (5)
N1B	0.022 (5)	0.028 (4)	0.030 (5)	−0.003 (4)	−0.006 (4)	0.000 (4)
N2B	0.010 (4)	0.040 (5)	0.041 (6)	0.001 (4)	0.005 (3)	0.003 (4)
C1B	0.037 (4)	0.029 (3)	0.013 (3)	0.003 (3)	−0.002 (3)	0.002 (3)
C2B	0.052 (4)	0.012 (3)	0.018 (4)	−0.005 (3)	0.008 (3)	0.000 (3)
C3B	0.052 (4)	0.012 (3)	0.018 (4)	−0.005 (3)	0.008 (3)	0.000 (3)
C4B	0.032 (6)	0.013 (4)	0.023 (5)	0.005 (4)	0.007 (4)	−0.004 (4)
C5B	0.029 (5)	0.013 (4)	0.020 (5)	0.002 (4)	0.001 (4)	0.013 (4)
O1A	0.026 (3)	0.029 (3)	0.018 (4)	−0.003 (3)	0.001 (3)	0.001 (3)
O2A	0.018 (3)	0.036 (4)	0.014 (4)	−0.005 (3)	0.002 (3)	0.003 (3)
O3A	0.031 (4)	0.025 (3)	0.014 (3)	−0.006 (3)	−0.003 (3)	−0.001 (3)
C6A	0.029 (5)	0.012 (4)	0.014 (5)	0.004 (4)	−0.007 (4)	0.003 (4)
C7A	0.020 (5)	0.020 (5)	0.029 (6)	0.000 (4)	−0.008 (4)	−0.006 (4)
C8A	0.024 (3)	0.007 (3)	0.027 (3)	−0.005 (3)	−0.002 (3)	0.000 (3)
C9A	0.021 (4)	0.020 (3)	0.013 (3)	0.000 (3)	−0.003 (3)	0.007 (3)
C10A	0.027 (5)	0.007 (4)	0.017 (5)	−0.001 (4)	−0.003 (4)	0.001 (3)
C11A	0.024 (5)	0.017 (4)	0.013 (5)	−0.004 (4)	0.000 (4)	−0.003 (4)
C12A	0.024 (5)	0.023 (4)	0.013 (5)	0.010 (4)	−0.001 (4)	−0.004 (4)
O1B	0.028 (4)	0.025 (3)	0.018 (4)	0.000 (3)	−0.001 (3)	−0.006 (3)
O2B	0.024 (3)	0.033 (3)	0.014 (4)	0.005 (3)	0.003 (3)	0.003 (3)
O3B	0.021 (3)	0.027 (3)	0.017 (3)	−0.002 (3)	−0.003 (3)	0.005 (3)
C6B	0.029 (5)	0.019 (5)	0.020 (5)	−0.008 (4)	0.002 (4)	0.004 (4)
C7B	0.028 (5)	0.020 (5)	0.021 (5)	0.001 (4)	−0.001 (4)	−0.012 (4)
C8B	0.024 (3)	0.007 (3)	0.027 (3)	−0.005 (3)	−0.002 (3)	0.000 (3)
C9B	0.021 (4)	0.020 (3)	0.013 (3)	0.000 (3)	−0.003 (3)	0.007 (3)
C10B	0.027 (5)	0.029 (5)	0.009 (5)	−0.007 (4)	0.002 (4)	−0.004 (4)
C11B	0.020 (5)	0.011 (4)	0.009 (4)	−0.004 (4)	−0.002 (3)	−0.001 (3)
C12B	0.019 (5)	0.019 (4)	0.014 (5)	−0.011 (4)	0.001 (4)	−0.004 (4)

Br1A—C2A	1.889 (10)	O2A—H2AC	0.8200
N1A—C1A	1.322 (11)	O3A—C12A	1.249 (10)
N1A—C5A	1.359 (11)	C6A—C11A	1.391 (12)
N2A—C5A	1.349 (12)	C6A—C7A	1.400 (13)
N2A—H2AA	0.8600	C6A—H6A	0.9300
N2A—H2AB	0.8600	C7A—C8A	1.378 (14)
C1A—C2A	1.394 (13)	C7A—H7A	0.9300
C1A—H1AA	0.9300	C8A—C9A	1.383 (13)
C2A—C3A	1.418 (14)	C9A—C10A	1.338 (13)
C3A—C4A	1.360 (12)	C9A—H9A	0.9300
C3A—H3AA	0.9300	C10A—C11A	1.393 (12)
C4A—C5A	1.402 (12)	C10A—H10A	0.9300
C4A—H4AA	0.9300	C11A—C12A	1.474 (13)
Br1B—C2B	1.912 (10)	O1B—C8B	1.384 (11)
N1B—C5B	1.351 (11)	O1B—H1BB	0.8200
N1B—C1B	1.359 (12)	O2B—C12B	1.312 (10)
N2B—C5B	1.318 (13)	O2B—H2BC	0.8200
N2B—H2BA	0.8600	O3B—C12B	1.250 (11)
N2B—H2BB	0.8600	C6B—C7B	1.396 (13)
C1B—C2B	1.332 (13)	C6B—C11B	1.401 (12)
C1B—H1BA	0.9300	C6B—H6B	0.9300
C2B—C3B	1.381 (14)	C7B—C8B	1.383 (14)
C3B—C4B	1.400 (12)	C7B—H7B	0.9300
C3B—H3BA	0.9300	C8B—C9B	1.379 (13)
C4B—C5B	1.410 (12)	C9B—C10B	1.358 (13)
C4B—H4BA	0.9300	C9B—H8B	0.9300
O1A—C8A	1.370 (10)	C10B—C11B	1.423 (13)
O1A—H1AB	0.8200	C10B—H10B	0.9300
O2A—C12A	1.307 (11)	C11B—C12B	1.456 (12)
C1A—N1A—C5A	119.3 (8)	C7A—C6A—H6A	119.7
C5A—N2A—H2AA	120.0	C8A—C7A—C6A	119.1 (8)
C5A—N2A—H2AB	120.0	C8A—C7A—H7A	120.4
H2AA—N2A—H2AB	120.0	C6A—C7A—H7A	120.4
N1A—C1A—C2A	123.1 (9)	O1A—C8A—C7A	117.9 (8)
N1A—C1A—H1AA	118.5	O1A—C8A—C9A	122.7 (9)
C2A—C1A—H1AA	118.5	C7A—C8A—C9A	119.4 (8)
C1A—C2A—C3A	118.7 (9)	C10A—C9A—C8A	121.8 (9)
C1A—C2A—Br1A	120.5 (8)	C10A—C9A—H9A	119.1
C3A—C2A—Br1A	120.8 (7)	C8A—C9A—H9A	119.1
C4A—C3A—C2A	117.0 (9)	C9A—C10A—C11A	120.7 (8)
C4A—C3A—H3AA	121.5	C9A—C10A—H10A	119.7
C2A—C3A—H3AA	121.5	C11A—C10A—H10A	119.7
C3A—C4A—C5A	122.0 (9)	C6A—C11A—C10A	118.4 (8)
C3A—C4A—H4AA	119.0	C6A—C11A—C12A	121.1 (8)
C5A—C4A—H4AA	119.0	C10A—C11A—C12A	120.5 (8)
N2A—C5A—N1A	115.5 (8)	O3A—C12A—O2A	122.8 (8)
N2A—C5A—C4A	124.6 (8)	O3A—C12A—C11A	122.3 (8)
N1A—C5A—C4A	119.9 (8)	O2A—C12A—C11A	114.9 (7)
C5B—N1B—C1B	120.1 (9)	C8B—O1B—H1BB	109.5
C5B—N2B—H2BA	120.0	C12B—O2B—H2BC	109.5
C5B—N2B—H2BB	120.0	C7B—C6B—C11B	121.1 (9)
H2BA—N2B—H2BB	120.0	C7B—C6B—H6B	119.5
C2B—C1B—N1B	121.0 (9)	C11B—C6B—H6B	119.5
C2B—C1B—H1BA	119.5	C8B—C7B—C6B	118.6 (9)
N1B—C1B—H1BA	119.5	C8B—C7B—H7B	120.7
C1B—C2B—C3B	121.9 (10)	C6B—C7B—H7B	120.7
C1B—C2B—Br1B	118.8 (8)	C9B—C8B—C7B	121.6 (8)
C3B—C2B—Br1B	119.3 (7)	C9B—C8B—O1B	118.7 (8)
C2B—C3B—C4B	117.9 (9)	C7B—C8B—O1B	119.6 (9)
C2B—C3B—H3BA	121.0	C10B—C9B—C8B	120.0 (8)
C4B—C3B—H3BA	121.0	C10B—C9B—H8B	120.0
C3B—C4B—C5B	118.7 (9)	C8B—C9B—H8B	120.0
C3B—C4B—H4BA	120.7	C9B—C10B—C11B	121.0 (9)
C5B—C4B—H4BA	120.7	C9B—C10B—H10B	119.5
N2B—C5B—N1B	117.2 (8)	C11B—C10B—H10B	119.5
N2B—C5B—C4B	122.5 (9)	C6B—C11B—C10B	117.7 (8)
N1B—C5B—C4B	120.3 (9)	C6B—C11B—C12B	119.9 (8)
C8A—O1A—H1AB	109.5	C10B—C11B—C12B	122.4 (8)
C12A—O2A—H2AC	109.5	O3B—C12B—O2B	121.2 (8)
C11A—C6A—C7A	120.6 (9)	O3B—C12B—C11B	124.0 (8)
C11A—C6A—H6A	119.7	O2B—C12B—C11B	114.8 (8)
C5A—N1A—C1A—C2A	2.4 (14)	C7A—C8A—C9A—C10A	−1.6 (13)
N1A—C1A—C2A—C3A	−1.6 (14)	C8A—C9A—C10A—C11A	2.3 (13)
N1A—C1A—C2A—Br1A	179.1 (7)	C7A—C6A—C11A—C10A	1.4 (13)
C1A—C2A—C3A—C4A	−0.9 (13)	C7A—C6A—C11A—C12A	−179.2 (8)
Br1A—C2A—C3A—C4A	178.4 (6)	C9A—C10A—C11A—C6A	−2.1 (13)
C2A—C3A—C4A—C5A	2.6 (13)	C9A—C10A—C11A—C12A	178.5 (8)
C1A—N1A—C5A—N2A	179.8 (8)	C6A—C11A—C12A—O3A	−178.3 (8)
C1A—N1A—C5A—C4A	−0.6 (13)	C10A—C11A—C12A—O3A	1.1 (13)
C3A—C4A—C5A—N2A	177.5 (9)	C6A—C11A—C12A—O2A	2.6 (12)
C3A—C4A—C5A—N1A	−1.9 (13)	C10A—C11A—C12A—O2A	−178.1 (8)
C5B—N1B—C1B—C2B	−1.8 (14)	C11B—C6B—C7B—C8B	−0.5 (13)
N1B—C1B—C2B—C3B	3.1 (14)	C6B—C7B—C8B—C9B	2.7 (13)
N1B—C1B—C2B—Br1B	−178.4 (7)	C6B—C7B—C8B—O1B	178.5 (7)
C1B—C2B—C3B—C4B	−2.4 (13)	C7B—C8B—C9B—C10B	−3.4 (13)
Br1B—C2B—C3B—C4B	179.1 (6)	O1B—C8B—C9B—C10B	−179.3 (8)
C2B—C3B—C4B—C5B	0.6 (12)	C8B—C9B—C10B—C11B	1.9 (13)
C1B—N1B—C5B—N2B	−178.7 (8)	C7B—C6B—C11B—C10B	−1.0 (12)
C1B—N1B—C5B—C4B	0.1 (13)	C7B—C6B—C11B—C12B	178.9 (8)
C3B—C4B—C5B—N2B	179.2 (8)	C9B—C10B—C11B—C6B	0.3 (12)
C3B—C4B—C5B—N1B	0.5 (12)	C9B—C10B—C11B—C12B	−179.5 (8)
C11A—C6A—C7A—C8A	−0.8 (13)	C6B—C11B—C12B—O3B	0.8 (12)
C6A—C7A—C8A—O1A	−177.2 (7)	C10B—C11B—C12B—O3B	−179.4 (8)
C6A—C7A—C8A—C9A	0.8 (13)	C6B—C11B—C12B—O2B	−180.0 (7)
O1A—C8A—C9A—C10A	176.3 (8)	C10B—C11B—C12B—O2B	−0.2 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2AA···O3Ai	0.86	2.19	2.996 (11)	155
N2A—H2AB···O1Aii	0.86	2.13	2.969 (11)	166
N2B—H2BA···O3Biii	0.86	2.19	3.020 (11)	163
O1A—H1AB···O3Biv	0.82	1.87	2.688 (8)	175
O2A—H2AC···N1Av	0.82	1.80	2.605 (10)	168
O1B—H1BB···O3Avi	0.82	1.94	2.762 (8)	177
O2B—H2BC···N1Bvii	0.82	1.85	2.663 (11)	170
C6B—H6B···O1Aviii	0.93	2.52	3.416 (11)	161
C7B—H7B···O3Avi	0.93	2.58	3.262 (12)	131
C9A—H9A···O3Biv	0.93	2.48	3.182 (11)	132
C10A—H10A···O1Bix	0.93	2.53	3.416 (11)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2AA⋯O3Ai	0.86	2.19	2.996 (11)	155
N2A—H2AB⋯O1Aii	0.86	2.13	2.969 (11)	166
N2B—H2BA⋯O3Biii	0.86	2.19	3.020 (11)	163
O1A—H1AB⋯O3Biv	0.82	1.87	2.688 (8)	175
O2A—H2AC⋯N1Av	0.82	1.80	2.605 (10)	168
O1B—H1BB⋯O3Avi	0.82	1.94	2.762 (8)	177
O2B—H2BC⋯N1Bvii	0.82	1.85	2.663 (11)	170
C6B—H6B⋯O1Aviii	0.93	2.52	3.416 (11)	161
C7B—H7B⋯O3Avi	0.93	2.58	3.262 (12)	131
C9A—H9A⋯O3Biv	0.93	2.48	3.182 (11)	132
C10A—H10A⋯O1Bix	0.93	2.53	3.416 (11)	158

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) .