2-Amino-4-methyl-pyridinium trifluoro-acetate.

The asymmetric unit of the title compound, C(6)H(9)N(2) (+)·C(2)F(3)O(2) (-), contains two independent 2-amino-4-methyl-pyridinium cations and two independent trifluoro-acetate anions. The F atoms of both anions are disordered over two sets of sites, with site occupancies of 0.50 (3) and 0.50 (3) in one of the anions, and 0.756 (9) and 0.244 (9) in the other. In the crystal, the cations and anions are linked into chains along the b axis by N-H⋯O hydrogen bonds and these chains are cross-linked by C-H⋯O hydrogen bonds, forming a two-dimensional network lying parallel to (101). The crystal structure is further stabilized by π-π inter-actions between the pyridinium rings [centroid-centroid distances = 3.5842 (13) and 3.5665 (16) Å].

Related literature

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997 ▶); Katritzky et al. (1996 ▶). For related structures, see: Kvick & Noordik (1977 ▶); Shen et al. (2008 ▶); Hemamalini & Fun (2010 ▶). For trifluoro­acetic acid, see: Rodrigues et al. (2001 ▶). For details of hydrogen bonding, see: Jeffrey & Saenger (1991 ▶); Jeffrey (1997 ▶); Scheiner (1997 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C6H9N2 +·C2F3O2 −

M = 222.17

Triclinic,

a = 8.5229 (2) Å

b = 11.0649 (3) Å

c = 11.6573 (3) Å

α = 81.208 (1)°

β = 72.199 (2)°

γ = 74.647 (1)°

V = 1006.26 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 296 K

0.56 × 0.19 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.925, T max = 0.989

21533 measured reflections

5803 independent reflections

3405 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.187

S = 1.06

5803 reflections

357 parameters

114 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.26 e Å−3

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/S1600536810008202/ci5038sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008202/ci5038Isup2.hkl

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

C6H9N2+·C2F3O2−	Z = 4
Mr = 222.17	F(000) = 456
Triclinic, P1	Dx = 1.467 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5229 (2) Å	Cell parameters from 4908 reflections
b = 11.0649 (3) Å	θ = 2.6–30.0°
c = 11.6573 (3) Å	µ = 0.14 mm−1
α = 81.208 (1)°	T = 296 K
β = 72.199 (2)°	Plate, colourless
γ = 74.647 (1)°	0.56 × 0.19 × 0.08 mm
V = 1006.26 (4) Å3

Bruker SMART APEXII CCD area-detector diffractometer	5803 independent reflections
Radiation source: fine-focus sealed tube	3405 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 30.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.925, Tmax = 0.989	k = −15→15
21533 measured reflections	l = −16→16

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0642P)2 + 0.3844P] where P = (Fo2 + 2Fc2)/3
5803 reflections	(Δ/σ)max = 0.001
357 parameters	Δρmax = 0.25 e Å−3
114 restraints	Δρmin = −0.26 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
N1A	0.3581 (3)	0.99313 (18)	0.21338 (18)	0.0510 (5)
N2A	0.2610 (3)	0.8369 (2)	0.1674 (2)	0.0672 (6)
C1A	0.4811 (3)	1.0518 (2)	0.2081 (2)	0.0589 (6)
H1AA	0.4538	1.1237	0.2490	0.071*
C2A	0.6422 (3)	1.0074 (3)	0.1447 (2)	0.0605 (6)
H2AA	0.7258	1.0485	0.1412	0.073*
C3A	0.6831 (3)	0.8980 (2)	0.0835 (2)	0.0553 (6)
C4A	0.5572 (3)	0.8401 (2)	0.0901 (2)	0.0548 (6)
H4AA	0.5829	0.7678	0.0500	0.066*
C5A	0.3900 (3)	0.8882 (2)	0.1564 (2)	0.0500 (6)
C6A	0.8627 (4)	0.8466 (3)	0.0138 (3)	0.0779 (8)
H6AA	0.8721	0.7662	−0.0125	0.117*
H6AB	0.9358	0.8373	0.0645	0.117*
H6AC	0.8951	0.9033	−0.0554	0.117*
N1B	0.2268 (3)	0.49192 (19)	0.32553 (19)	0.0529 (5)
N2B	0.1215 (4)	0.3395 (2)	0.2805 (2)	0.0708 (7)
C1B	0.2776 (3)	0.5451 (3)	0.4013 (2)	0.0600 (7)
H1BB	0.309 (4)	0.622 (3)	0.367 (3)	0.072 (8)*
C2B	0.2732 (3)	0.4938 (3)	0.5135 (3)	0.0634 (7)
H2BA	0.3074	0.5315	0.5648	0.076*
C3B	0.2162 (3)	0.3817 (3)	0.5533 (2)	0.0612 (6)
C4B	0.1643 (3)	0.3302 (2)	0.4769 (2)	0.0581 (6)
H4BA	0.1248	0.2572	0.5027	0.070*
C5B	0.1695 (3)	0.3855 (2)	0.3598 (2)	0.0508 (6)
C6B	0.2136 (6)	0.3216 (4)	0.6779 (3)	0.0997 (12)
H6BA	0.1825	0.2426	0.6877	0.149*
H6BB	0.1326	0.3759	0.7365	0.149*
H6BC	0.3240	0.3079	0.6894	0.149*
F1A	0.7612 (16)	0.1532 (10)	0.5327 (7)	0.084 (2)	0.50 (3)
F2A	0.6477 (14)	0.1650 (13)	0.3757 (10)	0.102 (3)	0.50 (3)
F3A	0.6788 (15)	0.0165 (9)	0.5069 (8)	0.093 (3)	0.50 (3)
F1C	0.7539 (17)	0.1841 (16)	0.5129 (13)	0.110 (4)	0.50 (3)
F2C	0.6745 (18)	0.2046 (15)	0.3790 (11)	0.122 (4)	0.50 (3)
F3C	0.6439 (18)	0.0349 (13)	0.4851 (15)	0.117 (4)	0.50 (3)
O1A	0.9324 (3)	−0.0511 (2)	0.3165 (2)	0.0937 (7)
O2A	1.0382 (2)	0.10073 (17)	0.34606 (19)	0.0712 (6)
C7A	0.9242 (3)	0.0450 (2)	0.3593 (2)	0.0562 (6)
C8A	0.7515 (3)	0.1063 (3)	0.4389 (2)	0.0636 (7)
F1B	0.4287 (6)	0.6567 (4)	0.8679 (3)	0.0917 (13)	0.756 (9)
F2B	0.1802 (5)	0.6740 (7)	0.8575 (4)	0.136 (2)	0.756 (9)
F3B	0.3737 (6)	0.5082 (4)	0.8111 (4)	0.1062 (14)	0.756 (9)
F1D	0.310 (2)	0.7120 (8)	0.8858 (9)	0.101 (4)	0.244 (9)
F2D	0.1842 (14)	0.6008 (13)	0.8405 (11)	0.094 (4)	0.244 (9)
F3D	0.4324 (15)	0.5237 (15)	0.8247 (14)	0.122 (5)	0.244 (9)
O1B	0.2191 (3)	0.4371 (2)	1.03426 (19)	0.0899 (7)
O2B	0.2503 (3)	0.60549 (17)	1.09745 (16)	0.0786 (6)
C7B	0.2531 (3)	0.5397 (2)	1.0201 (2)	0.0566 (6)
C8B	0.3048 (3)	0.5954 (3)	0.8898 (2)	0.0649 (7)
H1NA	0.252 (4)	1.022 (2)	0.257 (2)	0.057 (7)*
H2NA	0.161 (3)	0.869 (2)	0.209 (2)	0.062 (8)*
H3NA	0.276 (4)	0.775 (2)	0.127 (2)	0.077 (9)*
H1NB	0.238 (3)	0.524 (2)	0.251 (3)	0.058 (7)*
H2NB	0.146 (4)	0.368 (3)	0.2065 (19)	0.079 (10)*
H3NB	0.078 (3)	0.278 (2)	0.301 (3)	0.070 (9)*

	U11	U22	U33	U12	U13	U23
N1A	0.0562 (13)	0.0494 (11)	0.0466 (11)	−0.0169 (9)	−0.0063 (10)	−0.0099 (8)
N2A	0.0761 (17)	0.0585 (14)	0.0704 (15)	−0.0299 (13)	−0.0057 (13)	−0.0204 (12)
C1A	0.0699 (17)	0.0555 (14)	0.0587 (15)	−0.0232 (13)	−0.0167 (13)	−0.0136 (11)
C2A	0.0599 (16)	0.0667 (16)	0.0606 (15)	−0.0210 (13)	−0.0189 (13)	−0.0064 (12)
C3A	0.0599 (15)	0.0566 (14)	0.0451 (13)	−0.0056 (12)	−0.0168 (11)	−0.0005 (10)
C4A	0.0710 (16)	0.0439 (12)	0.0463 (13)	−0.0077 (11)	−0.0160 (12)	−0.0049 (10)
C5A	0.0684 (16)	0.0418 (11)	0.0407 (11)	−0.0174 (11)	−0.0143 (11)	0.0007 (9)
C6A	0.0636 (18)	0.084 (2)	0.076 (2)	−0.0031 (15)	−0.0145 (15)	−0.0103 (16)
N1B	0.0631 (13)	0.0487 (11)	0.0455 (11)	−0.0230 (10)	−0.0047 (10)	−0.0029 (9)
N2B	0.0989 (19)	0.0645 (15)	0.0620 (15)	−0.0456 (14)	−0.0189 (14)	−0.0039 (12)
C1B	0.0676 (17)	0.0579 (15)	0.0575 (15)	−0.0305 (13)	−0.0076 (12)	−0.0056 (12)
C2B	0.0653 (16)	0.0714 (17)	0.0621 (16)	−0.0281 (14)	−0.0186 (13)	−0.0066 (13)
C3B	0.0603 (15)	0.0629 (15)	0.0607 (15)	−0.0179 (12)	−0.0191 (12)	0.0055 (12)
C4B	0.0627 (15)	0.0490 (13)	0.0619 (15)	−0.0228 (12)	−0.0122 (12)	0.0048 (11)
C5B	0.0505 (13)	0.0451 (12)	0.0545 (14)	−0.0159 (10)	−0.0054 (10)	−0.0068 (10)
C6B	0.140 (3)	0.101 (3)	0.079 (2)	−0.054 (2)	−0.058 (2)	0.0303 (19)
F1A	0.096 (4)	0.091 (4)	0.054 (3)	−0.014 (3)	−0.010 (2)	−0.012 (3)
F2A	0.083 (4)	0.122 (5)	0.092 (4)	0.007 (4)	−0.037 (3)	−0.012 (4)
F3A	0.076 (4)	0.117 (4)	0.073 (4)	−0.038 (3)	0.000 (3)	0.015 (3)
F1C	0.101 (5)	0.114 (6)	0.127 (6)	−0.038 (4)	−0.010 (4)	−0.068 (5)
F2C	0.100 (5)	0.125 (6)	0.103 (5)	0.013 (4)	−0.025 (3)	0.023 (4)
F3C	0.080 (4)	0.131 (6)	0.146 (7)	−0.068 (4)	0.001 (4)	−0.024 (4)
O1A	0.0789 (14)	0.0947 (16)	0.1201 (19)	−0.0387 (12)	−0.0099 (13)	−0.0498 (14)
O2A	0.0621 (11)	0.0612 (11)	0.0907 (14)	−0.0314 (9)	−0.0031 (10)	−0.0147 (10)
C7A	0.0600 (15)	0.0598 (14)	0.0554 (14)	−0.0271 (12)	−0.0143 (12)	−0.0044 (11)
C8A	0.0613 (16)	0.0771 (19)	0.0573 (16)	−0.0277 (14)	−0.0137 (13)	−0.0049 (13)
F1B	0.098 (3)	0.100 (2)	0.0800 (17)	−0.053 (2)	−0.0076 (16)	0.0035 (15)
F2B	0.086 (2)	0.174 (4)	0.093 (2)	0.023 (3)	−0.0136 (18)	0.040 (3)
F3B	0.119 (3)	0.130 (3)	0.0665 (18)	−0.051 (2)	0.0142 (19)	−0.0440 (16)
F1D	0.146 (8)	0.084 (5)	0.079 (5)	−0.052 (5)	−0.025 (5)	0.008 (4)
F2D	0.105 (6)	0.113 (7)	0.084 (5)	−0.030 (5)	−0.062 (5)	0.012 (5)
F3D	0.078 (6)	0.148 (8)	0.112 (7)	−0.006 (5)	−0.002 (5)	−0.010 (6)
O1B	0.140 (2)	0.0703 (13)	0.0708 (13)	−0.0528 (14)	−0.0189 (13)	−0.0111 (10)
O2B	0.1372 (19)	0.0565 (11)	0.0532 (11)	−0.0412 (12)	−0.0259 (11)	−0.0054 (8)
C7B	0.0670 (16)	0.0506 (13)	0.0537 (14)	−0.0165 (12)	−0.0137 (12)	−0.0094 (11)
C8B	0.0657 (18)	0.0713 (18)	0.0547 (15)	−0.0147 (15)	−0.0106 (13)	−0.0108 (13)

N1A—C5A	1.350 (3)	C2B—H2BA	0.93
N1A—C1A	1.354 (3)	C3B—C4B	1.356 (4)
N1A—H1NA	0.89 (3)	C3B—C6B	1.499 (4)
N2A—C5A	1.330 (3)	C4B—C5B	1.401 (3)
N2A—H2NA	0.855 (18)	C4B—H4BA	0.93
N2A—H3NA	0.850 (19)	C6B—H6BA	0.96
C1A—C2A	1.344 (4)	C6B—H6BB	0.96
C1A—H1AA	0.93	C6B—H6BC	0.96
C2A—C3A	1.408 (4)	F1A—C8A	1.314 (6)
C2A—H2AA	0.93	F2A—C8A	1.301 (6)
C3A—C4A	1.366 (3)	F3A—C8A	1.336 (6)
C3A—C6A	1.499 (4)	F1C—C8A	1.316 (6)
C4A—C5A	1.401 (3)	F2C—C8A	1.331 (6)
C4A—H4AA	0.93	F3C—C8A	1.306 (6)
C6A—H6AA	0.96	O1A—C7A	1.219 (3)
C6A—H6AB	0.96	O2A—C7A	1.243 (3)
C6A—H6AC	0.96	C7A—C8A	1.522 (4)
N1B—C5B	1.351 (3)	F1B—C8B	1.343 (4)
N1B—C1B	1.356 (3)	F2B—C8B	1.296 (4)
N1B—H1NB	0.88 (3)	F3B—C8B	1.326 (4)
N2B—C5B	1.329 (3)	F1D—C8B	1.297 (6)
N2B—H2NB	0.854 (19)	F2D—C8B	1.307 (7)
N2B—H3NB	0.830 (19)	F3D—C8B	1.269 (8)
C1B—C2B	1.338 (4)	O1B—C7B	1.220 (3)
C1B—H1BB	0.95 (3)	O2B—C7B	1.233 (3)
C2B—C3B	1.412 (4)	C7B—C8B	1.526 (4)
C5A—N1A—C1A	122.3 (2)	C4B—C3B—C2B	118.8 (2)
C5A—N1A—H1NA	116.6 (16)	C4B—C3B—C6B	121.1 (3)
C1A—N1A—H1NA	121.0 (16)	C2B—C3B—C6B	120.0 (3)
C5A—N2A—H2NA	121.2 (18)	C3B—C4B—C5B	120.9 (2)
C5A—N2A—H3NA	119 (2)	C3B—C4B—H4BA	119.5
H2NA—N2A—H3NA	119 (3)	C5B—C4B—H4BA	119.5
C2A—C1A—N1A	120.9 (2)	N2B—C5B—N1B	118.1 (2)
C2A—C1A—H1AA	119.5	N2B—C5B—C4B	123.9 (2)
N1A—C1A—H1AA	119.5	N1B—C5B—C4B	118.0 (2)
C1A—C2A—C3A	119.3 (2)	C3B—C6B—H6BA	109.5
C1A—C2A—H2AA	120.3	C3B—C6B—H6BB	109.5
C3A—C2A—H2AA	120.3	H6BA—C6B—H6BB	109.5
C4A—C3A—C2A	118.9 (2)	C3B—C6B—H6BC	109.5
C4A—C3A—C6A	121.2 (2)	H6BA—C6B—H6BC	109.5
C2A—C3A—C6A	119.9 (3)	H6BB—C6B—H6BC	109.5
C3A—C4A—C5A	120.8 (2)	O1A—C7A—O2A	128.6 (3)
C3A—C4A—H4AA	119.6	O1A—C7A—C8A	116.2 (2)
C5A—C4A—H4AA	119.6	O2A—C7A—C8A	115.2 (2)
N2A—C5A—N1A	117.9 (2)	F2A—C8A—F1A	122.3 (9)
N2A—C5A—C4A	124.3 (2)	F3C—C8A—F1C	114.7 (11)
N1A—C5A—C4A	117.7 (2)	F3C—C8A—F2C	106.7 (7)
C3A—C6A—H6AA	109.5	F1C—C8A—F2C	88.3 (16)
C3A—C6A—H6AB	109.5	F2A—C8A—F3A	104.7 (7)
H6AA—C6A—H6AB	109.5	F1A—C8A—F3A	93.2 (7)
C3A—C6A—H6AC	109.5	F2A—C8A—C7A	112.1 (6)
H6AA—C6A—H6AC	109.5	F1A—C8A—C7A	112.8 (6)
H6AB—C6A—H6AC	109.5	F3A—C8A—C7A	108.9 (5)
C5B—N1B—C1B	121.7 (2)	O1B—C7B—O2B	128.6 (3)
C5B—N1B—H1NB	118.8 (17)	O1B—C7B—C8B	116.2 (2)
C1B—N1B—H1NB	119.3 (16)	O2B—C7B—C8B	115.2 (2)
C5B—N2B—H2NB	120 (2)	F3D—C8B—F1D	116.9 (9)
C5B—N2B—H3NB	120 (2)	F3D—C8B—F2D	103.4 (9)
H2NB—N2B—H3NB	120 (3)	F1D—C8B—F2D	103.7 (7)
C2B—C1B—N1B	121.1 (2)	F2B—C8B—F3B	108.5 (4)
C2B—C1B—H1BB	125.9 (17)	F2B—C8B—F1B	106.5 (4)
N1B—C1B—H1BB	112.9 (17)	F3B—C8B—F1B	101.8 (3)
C1B—C2B—C3B	119.4 (2)	F2B—C8B—C7B	113.0 (3)
C1B—C2B—H2BA	120.3	F3B—C8B—C7B	112.8 (3)
C3B—C2B—H2BA	120.3	F1B—C8B—C7B	113.5 (2)
C5A—N1A—C1A—C2A	0.2 (4)	O1A—C7A—C8A—F3C	20.8 (11)
N1A—C1A—C2A—C3A	−0.3 (4)	O2A—C7A—C8A—F3C	−159.7 (11)
C1A—C2A—C3A—C4A	0.2 (4)	O1A—C7A—C8A—F1A	141.7 (6)
C1A—C2A—C3A—C6A	−179.2 (3)	O2A—C7A—C8A—F1A	−38.8 (6)
C2A—C3A—C4A—C5A	0.0 (4)	O1A—C7A—C8A—F1C	159.8 (10)
C6A—C3A—C4A—C5A	179.4 (2)	O2A—C7A—C8A—F1C	−20.6 (10)
C1A—N1A—C5A—N2A	179.6 (2)	O1A—C7A—C8A—F2C	−101.8 (11)
C1A—N1A—C5A—C4A	0.0 (3)	O2A—C7A—C8A—F2C	77.7 (11)
C3A—C4A—C5A—N2A	−179.7 (2)	O1A—C7A—C8A—F3A	39.7 (6)
C3A—C4A—C5A—N1A	−0.1 (3)	O2A—C7A—C8A—F3A	−140.8 (6)
C5B—N1B—C1B—C2B	0.1 (4)	O1B—C7B—C8B—F3D	−57.7 (10)
N1B—C1B—C2B—C3B	0.6 (4)	O2B—C7B—C8B—F3D	122.7 (10)
C1B—C2B—C3B—C4B	−1.2 (4)	O1B—C7B—C8B—F2B	96.6 (5)
C1B—C2B—C3B—C6B	178.8 (3)	O2B—C7B—C8B—F2B	−83.0 (5)
C2B—C3B—C4B—C5B	1.1 (4)	O1B—C7B—C8B—F1D	169.3 (10)
C6B—C3B—C4B—C5B	−179.0 (3)	O2B—C7B—C8B—F1D	−10.3 (10)
C1B—N1B—C5B—N2B	179.7 (3)	O1B—C7B—C8B—F2D	55.9 (8)
C1B—N1B—C5B—C4B	−0.3 (4)	O2B—C7B—C8B—F2D	−123.7 (7)
C3B—C4B—C5B—N2B	179.6 (3)	O1B—C7B—C8B—F3B	−26.9 (4)
C3B—C4B—C5B—N1B	−0.3 (4)	O2B—C7B—C8B—F3B	153.5 (3)
O1A—C7A—C8A—F2A	−75.6 (8)	O1B—C7B—C8B—F1B	−142.0 (3)
O2A—C7A—C8A—F2A	103.9 (8)	O2B—C7B—C8B—F1B	38.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O2Ai	0.89 (3)	1.85 (3)	2.740 (3)	173 (2)
N2A—H2NA···O1Ai	0.85 (2)	2.02 (2)	2.871 (3)	176 (2)
N2A—H3NA···O2Bii	0.85 (2)	2.04 (2)	2.835 (3)	156 (2)
N1B—H1NB···O2Bii	0.87 (3)	1.86 (3)	2.734 (3)	175 (2)
N2B—H2NB···O1Bii	0.85 (2)	2.01 (2)	2.858 (3)	176 (3)
N2B—H3NB···O2Aiii	0.83 (3)	2.04 (2)	2.848 (3)	164 (3)
C4A—H4AA···O1Biv	0.93	2.57	3.423 (3)	153
C6B—H6BA···O1Av	0.96	2.57	3.518 (5)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O2Ai	0.89 (3)	1.85 (3)	2.740 (3)	173 (2)
N2A—H2NA⋯O1Ai	0.85 (2)	2.02 (2)	2.871 (3)	176 (2)
N2A—H3NA⋯O2Bii	0.85 (2)	2.04 (2)	2.835 (3)	156 (2)
N1B—H1NB⋯O2Bii	0.87 (3)	1.86 (3)	2.734 (3)	175 (2)
N2B—H2NB⋯O1Bii	0.85 (2)	2.01 (2)	2.858 (3)	176 (3)
N2B—H3NB⋯O2Aiii	0.83 (3)	2.04 (2)	2.848 (3)	164 (3)
C4A—H4AA⋯O1Biv	0.93	2.57	3.423 (3)	153
C6B—H6BA⋯O1Av	0.96	2.57	3.518 (5)	169

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