2-Amino-5-nitro-pyridinium tri-fluoro-acetate.

The title salt, C5H6N3O2 (+)·C2F3O2 (-), crystallizes with two cations and two anions in the asymmetric unit. In the crystal, the acetate and pyridine groups are linked by a pair of N-H⋯O hydrogen bonds, forming loops described by the graph-set motif R 2 (2)(8). These loops are linked via N-H⋯O hydrogen bonds, forming chains along [001]. The chains are in turn linked by C-H⋯O and C-H⋯F hydrogen bonds, generating a three-dimensional supra-molecular network. In both anions, the O and F atoms are disordered over two sites, with occupancy ratios of 0.852 (3):0.148 (3) and 0.851 (3):0.149 (3).

Related literature

For the biological properties of pyridine derivatives and compounds containing the imidazo[1,2-a]pyridine ring system, see: Trapani et al. (2003 ▶); Gueiffier et al. (1998 ▶); Rival et al. (1992 ▶); Rupert et al. (2003 ▶). For the crystal structure of a related compound, see: Hemamalini & Fun (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C5H6N3O2 +·C2F3O2 −

M = 506.30

Monoclinic,

a = 19.1388 (7) Å

b = 10.7716 (4) Å

c = 10.0707 (3) Å

β = 104.668 (2)°

V = 2008.47 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 293 K

0.30 × 0.30 × 0.25 mm

Data collection

Bruker APEXII Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.950, T max = 0.958

18608 measured reflections

4064 independent reflections

3006 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.118

S = 1.06

4064 reflections

367 parameters

25 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813011896/su2582sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011896/su2582Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011896/su2582Isup3.cml

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

C5H6N3O2+·C2F3O2−	F(000) = 1024
Mr = 506.30	Dx = 1.674 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6393 reflections
a = 19.1388 (7) Å	θ = 2.2–25.4°
b = 10.7716 (4) Å	µ = 0.17 mm−1
c = 10.0707 (3) Å	T = 293 K
β = 104.668 (2)°	Block, colourless
V = 2008.47 (12) Å3	0.30 × 0.30 × 0.25 mm
Z = 4

Bruker APEXII Kappa CCD diffractometer	4064 independent reflections
Radiation source: fine-focus sealed tube	3006 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scans	θmax = 26.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −23→23
Tmin = 0.950, Tmax = 0.958	k = −13→13
18608 measured reflections	l = −12→8

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0512P)2 + 0.6997P] where P = (Fo2 + 2Fc2)/3
4064 reflections	(Δ/σ)max = 0.001
367 parameters	Δρmax = 0.28 e Å−3
25 restraints	Δρmin = −0.30 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles.

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 > 2sigma(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)
F1'	0.6216 (3)	0.0649 (2)	0.6851 (3)	0.0814 (9)	0.852 (3)
F2'	0.56447 (14)	0.2115 (4)	0.5636 (3)	0.1083 (15)	0.852 (3)
F3'	0.63061 (13)	0.2483 (2)	0.7641 (2)	0.0768 (9)	0.852 (3)
O3'	0.70962 (17)	0.31733 (18)	0.5942 (3)	0.0575 (10)	0.852 (3)
O4'	0.7170 (6)	0.1168 (5)	0.5457 (14)	0.0457 (12)	0.852 (3)
C6	0.69027 (10)	0.20703 (17)	0.58967 (18)	0.0399 (6)
C7	0.62582 (11)	0.1822 (2)	0.6500 (2)	0.0512 (7)
F1	0.624 (2)	0.0769 (12)	0.717 (2)	0.0814 (9)	0.148 (3)
F2	0.5709 (9)	0.171 (3)	0.5411 (17)	0.1083 (15)	0.148 (3)
F3	0.6058 (9)	0.2704 (12)	0.7193 (13)	0.0768 (9)	0.148 (3)
O3	0.6905 (13)	0.3188 (9)	0.558 (2)	0.0575 (10)	0.148 (3)
O4	0.725 (4)	0.122 (3)	0.555 (9)	0.0457 (12)	0.148 (3)
F4	1.09841 (15)	0.2673 (2)	0.9010 (3)	0.1233 (10)	0.851 (3)
F5	1.15881 (12)	0.1049 (2)	0.8967 (2)	0.1058 (9)	0.851 (3)
F6	1.08797 (13)	0.1125 (3)	1.0222 (3)	0.1281 (12)	0.851 (3)
O7	1.2114 (4)	0.3372 (2)	1.0927 (10)	0.0567 (16)	0.851 (3)
O8	1.2245 (3)	0.1454 (6)	1.1793 (7)	0.0529 (13)	0.851 (3)
C13	1.19568 (11)	0.22682 (19)	1.0956 (2)	0.0450 (7)
C14	1.13362 (13)	0.1801 (2)	0.9792 (2)	0.0613 (8)
F4'	1.1391 (8)	0.2274 (13)	0.8650 (10)	0.1233 (10)	0.149 (3)
F5'	1.1264 (8)	0.0609 (8)	0.9603 (13)	0.1058 (9)	0.149 (3)
F6'	1.0714 (5)	0.2141 (16)	0.9973 (18)	0.1281 (12)	0.149 (3)
O7'	1.195 (2)	0.3400 (9)	1.109 (6)	0.054 (9)	0.149 (3)
O8'	1.2391 (18)	0.150 (3)	1.163 (4)	0.045 (6)	0.149 (3)
O1	0.96571 (10)	0.58183 (17)	0.87250 (19)	0.0753 (7)
O2	1.00888 (11)	0.4598 (2)	0.7436 (3)	0.0991 (9)
N1	0.82378 (8)	0.31869 (13)	0.91912 (15)	0.0381 (5)
N2	0.78170 (10)	0.11850 (16)	0.8954 (2)	0.0517 (6)
N3	0.96796 (10)	0.4827 (2)	0.8153 (2)	0.0606 (7)
C1	0.86882 (10)	0.40934 (17)	0.90128 (18)	0.0408 (6)
C2	0.91883 (10)	0.38461 (18)	0.83148 (19)	0.0437 (6)
C3	0.92425 (11)	0.2660 (2)	0.7785 (2)	0.0500 (7)
C4	0.87916 (10)	0.1762 (2)	0.7980 (2)	0.0490 (7)
C5	0.82704 (9)	0.20153 (17)	0.87184 (18)	0.0385 (5)
O5	1.44036 (10)	0.50593 (17)	1.1714 (2)	0.0860 (7)
O6	1.48351 (9)	0.36088 (19)	1.31572 (16)	0.0756 (6)
N4	1.32454 (8)	0.25957 (13)	0.90524 (15)	0.0403 (5)
N5	1.30568 (10)	0.06118 (17)	0.82079 (19)	0.0533 (6)
N6	1.44654 (9)	0.3977 (2)	1.20577 (19)	0.0564 (7)
C8	1.35833 (10)	0.34404 (17)	0.99745 (19)	0.0417 (6)
C9	1.40837 (10)	0.30535 (18)	1.10970 (19)	0.0425 (6)
C10	1.42431 (10)	0.17906 (19)	1.1319 (2)	0.0477 (6)
C11	1.39007 (11)	0.09627 (18)	1.0385 (2)	0.0459 (6)
C12	1.33876 (10)	0.13646 (16)	0.91913 (19)	0.0394 (6)
H1	0.86560	0.48830	0.93670	0.0490*
H1A	0.79150	0.33570	0.96230	0.0460*
H2A	0.7521 (11)	0.135 (2)	0.953 (2)	0.065 (7)*
H2B	0.7837 (13)	0.0419 (17)	0.862 (2)	0.068 (7)*
H3	0.95870	0.24950	0.73020	0.0600*
H4	0.88220	0.09710	0.76280	0.0590*
H4A	1.29250	0.28480	0.83420	0.0480*
H5A	1.2713 (10)	0.092 (2)	0.7491 (18)	0.065 (7)*
H5B	1.3104 (13)	−0.018 (2)	0.840 (2)	0.066 (7)*
H8	1.34740	0.42800	0.98410	0.0500*
H10	1.45820	0.15290	1.21030	0.0570*
H11	1.40010	0.01210	1.05240	0.0550*

	U11	U22	U33	U12	U13	U23
F1'	0.1041 (13)	0.0575 (10)	0.108 (2)	−0.0127 (10)	0.074 (2)	0.0002 (11)
F2'	0.0443 (10)	0.182 (4)	0.0999 (15)	0.0261 (13)	0.0206 (10)	0.0242 (15)
F3'	0.0902 (18)	0.0800 (13)	0.0738 (14)	0.0095 (10)	0.0457 (12)	−0.0166 (11)
O3'	0.076 (2)	0.0308 (8)	0.076 (2)	−0.0038 (9)	0.0383 (15)	−0.0069 (8)
O4'	0.048 (3)	0.0320 (9)	0.064 (2)	0.0004 (12)	0.027 (3)	−0.0028 (9)
C6	0.0466 (10)	0.0315 (10)	0.0434 (10)	0.0018 (8)	0.0145 (8)	0.0004 (8)
C7	0.0504 (12)	0.0497 (12)	0.0588 (12)	0.0055 (10)	0.0237 (10)	0.0010 (10)
F1	0.1041 (13)	0.0575 (10)	0.108 (2)	−0.0127 (10)	0.074 (2)	0.0002 (11)
F2	0.0443 (10)	0.182 (4)	0.0999 (15)	0.0261 (13)	0.0206 (10)	0.0242 (15)
F3	0.0902 (18)	0.0800 (13)	0.0738 (14)	0.0095 (10)	0.0457 (12)	−0.0166 (11)
O3	0.076 (2)	0.0308 (8)	0.076 (2)	−0.0038 (9)	0.0383 (15)	−0.0069 (8)
O4	0.048 (3)	0.0320 (9)	0.064 (2)	0.0004 (12)	0.027 (3)	−0.0028 (9)
F4	0.109 (2)	0.0852 (15)	0.1244 (18)	0.0264 (13)	−0.0654 (16)	0.0034 (13)
F5	0.0952 (16)	0.1350 (19)	0.0739 (13)	0.0144 (14)	−0.0033 (10)	−0.0568 (13)
F6	0.0820 (14)	0.178 (3)	0.1117 (17)	−0.0743 (18)	0.0010 (13)	−0.0013 (19)
O7	0.056 (4)	0.0419 (17)	0.0666 (17)	0.0009 (13)	0.005 (2)	0.0002 (15)
O8	0.056 (3)	0.0368 (15)	0.055 (2)	0.0024 (17)	−0.006 (2)	−0.0057 (13)
C13	0.0423 (11)	0.0408 (12)	0.0486 (11)	0.0064 (9)	0.0052 (8)	−0.0068 (9)
C14	0.0556 (13)	0.0542 (14)	0.0627 (14)	0.0072 (11)	−0.0061 (11)	−0.0064 (11)
F4'	0.109 (2)	0.0852 (15)	0.1244 (18)	0.0264 (13)	−0.0654 (16)	0.0034 (13)
F5'	0.0952 (16)	0.1350 (19)	0.0739 (13)	0.0144 (14)	−0.0033 (10)	−0.0568 (13)
F6'	0.0820 (14)	0.178 (3)	0.1117 (17)	−0.0743 (18)	0.0010 (13)	−0.0013 (19)
O7'	0.043 (14)	0.026 (8)	0.08 (2)	0.013 (6)	−0.006 (12)	−0.014 (8)
O8'	0.034 (9)	0.044 (10)	0.059 (10)	0.005 (7)	0.015 (7)	−0.007 (6)
O1	0.0771 (12)	0.0604 (11)	0.0829 (12)	−0.0246 (9)	0.0099 (9)	0.0145 (9)
O2	0.0768 (13)	0.0950 (15)	0.1466 (19)	0.0023 (11)	0.0674 (14)	0.0403 (13)
N1	0.0381 (8)	0.0327 (8)	0.0460 (8)	0.0026 (6)	0.0153 (6)	−0.0017 (6)
N2	0.0548 (11)	0.0353 (10)	0.0711 (12)	−0.0039 (8)	0.0271 (9)	−0.0098 (8)
N3	0.0436 (10)	0.0655 (14)	0.0702 (12)	−0.0022 (9)	0.0098 (9)	0.0302 (11)
C1	0.0414 (10)	0.0332 (9)	0.0453 (10)	0.0011 (8)	0.0062 (8)	0.0046 (8)
C2	0.0334 (9)	0.0471 (11)	0.0488 (10)	0.0008 (8)	0.0069 (8)	0.0134 (9)
C3	0.0377 (10)	0.0625 (14)	0.0528 (11)	0.0094 (9)	0.0169 (9)	0.0043 (10)
C4	0.0451 (11)	0.0465 (12)	0.0564 (11)	0.0077 (9)	0.0147 (9)	−0.0095 (9)
C5	0.0369 (9)	0.0337 (9)	0.0440 (9)	0.0035 (8)	0.0085 (8)	−0.0022 (8)
O5	0.0863 (13)	0.0543 (11)	0.1018 (14)	−0.0114 (10)	−0.0050 (11)	−0.0169 (10)
O6	0.0656 (10)	0.1026 (14)	0.0505 (9)	0.0010 (10)	−0.0002 (8)	−0.0128 (9)
N4	0.0404 (8)	0.0309 (8)	0.0449 (8)	0.0026 (6)	0.0024 (7)	0.0069 (7)
N5	0.0614 (11)	0.0309 (9)	0.0612 (11)	−0.0006 (8)	0.0036 (9)	0.0047 (8)
N6	0.0433 (10)	0.0675 (13)	0.0565 (11)	−0.0012 (9)	0.0093 (8)	−0.0115 (9)
C8	0.0407 (10)	0.0317 (9)	0.0524 (10)	0.0002 (8)	0.0115 (8)	0.0022 (8)
C9	0.0368 (10)	0.0452 (11)	0.0456 (10)	0.0002 (8)	0.0107 (8)	−0.0004 (8)
C10	0.0424 (10)	0.0550 (13)	0.0444 (10)	0.0077 (9)	0.0087 (8)	0.0127 (9)
C11	0.0501 (11)	0.0354 (10)	0.0522 (11)	0.0088 (9)	0.0129 (9)	0.0142 (9)
C12	0.0398 (10)	0.0305 (9)	0.0489 (10)	0.0007 (8)	0.0131 (8)	0.0075 (8)

F1—C7	1.325 (16)	N3—C2	1.451 (3)
F1'—C7	1.320 (3)	N1—H1A	0.8600
F2—C7	1.319 (17)	N2—H2B	0.896 (19)
F2'—C7	1.311 (4)	N2—H2A	0.93 (2)
F3—C7	1.293 (14)	N4—C12	1.354 (2)
F3'—C7	1.335 (3)	N4—C8	1.343 (2)
F4—C14	1.299 (3)	N5—C12	1.312 (3)
F4'—C14	1.286 (11)	N6—C9	1.450 (3)
F5—C14	1.335 (3)	N4—H4A	0.8600
F5'—C14	1.300 (9)	N5—H5A	0.908 (19)
F6—C14	1.293 (4)	N5—H5B	0.87 (2)
F6'—C14	1.302 (12)	C6—C7	1.530 (3)
O3—C6	1.246 (11)	C13—C14	1.527 (3)
O3'—C6	1.242 (3)	C1—C2	1.350 (3)
O4—C6	1.23 (6)	C2—C3	1.399 (3)
O4'—C6	1.232 (9)	C3—C4	1.343 (3)
O7—C13	1.229 (4)	C4—C5	1.414 (3)
O7'—C13	1.227 (12)	C1—H1	0.9300
O8—C13	1.244 (7)	C3—H3	0.9300
O8'—C13	1.25 (4)	C4—H4	0.9300
O1—N3	1.219 (3)	C8—C9	1.349 (3)
O2—N3	1.217 (3)	C9—C10	1.400 (3)
O5—N6	1.213 (3)	C10—C11	1.341 (3)
O6—N6	1.220 (2)	C11—C12	1.414 (3)
N1—C1	1.344 (2)	C8—H8	0.9300
N1—C5	1.356 (2)	C10—H10	0.9300
N2—C5	1.309 (3)	C11—H11	0.9300
C1—N1—C5	122.76 (16)	F4—C14—C13	114.2 (2)
O1—N3—C2	118.91 (19)	F5'—C14—C13	118.1 (6)
O2—N3—C2	116.9 (2)	F6'—C14—C13	111.2 (8)
O1—N3—O2	124.2 (2)	F4'—C14—F5'	106.9 (8)
C5—N1—H1A	119.00	F5—C14—C13	110.2 (2)
C1—N1—H1A	119.00	F4'—C14—C13	109.4 (6)
H2A—N2—H2B	120 (2)	F5—C14—F6	104.4 (2)
C5—N2—H2B	117.9 (16)	F4—C14—F6	108.6 (3)
C5—N2—H2A	121.5 (13)	F5'—C14—F6'	103.4 (10)
C8—N4—C12	122.89 (16)	F6—C14—C13	112.9 (2)
O5—N6—C9	118.21 (18)	F4'—C14—F6'	107.4 (10)
O6—N6—C9	117.5 (2)	F4—C14—F5	106.0 (2)
O5—N6—O6	124.3 (2)	N1—C1—C2	119.31 (17)
C12—N4—H4A	119.00	N3—C2—C3	120.64 (18)
C8—N4—H4A	119.00	C1—C2—C3	120.66 (18)
C12—N5—H5B	115.7 (14)	N3—C2—C1	118.69 (18)
C12—N5—H5A	119.2 (13)	C2—C3—C4	119.31 (19)
H5A—N5—H5B	123 (2)	C3—C4—C5	120.19 (19)
O3'—C6—C7	114.6 (2)	N2—C5—C4	123.50 (18)
O4—C6—C7	122 (3)	N1—C5—N2	118.73 (17)
O4'—C6—C7	117.1 (5)	N1—C5—C4	117.76 (17)
O3—C6—C7	109.0 (11)	C2—C1—H1	120.00
O3'—C6—O4'	128.4 (5)	N1—C1—H1	120.00
O3—C6—O4	128 (3)	C2—C3—H3	120.00
F2'—C7—F3'	107.3 (2)	C4—C3—H3	120.00
F2—C7—F3	103.5 (14)	C5—C4—H4	120.00
F1'—C7—F3'	106.0 (2)	C3—C4—H4	120.00
F1'—C7—C6	112.6 (3)	N4—C8—C9	119.03 (17)
F3'—C7—C6	111.22 (19)	N6—C9—C8	118.56 (18)
F3—C7—C6	117.7 (7)	C8—C9—C10	120.92 (18)
F2'—C7—C6	111.8 (2)	N6—C9—C10	120.51 (17)
F1—C7—F3	107.7 (12)	C9—C10—C11	119.10 (18)
F2—C7—C6	103.8 (8)	C10—C11—C12	120.25 (18)
F1—C7—F2	103.1 (18)	N4—C12—C11	117.77 (16)
F1'—C7—F2'	107.6 (3)	N5—C12—C11	123.44 (17)
F1—C7—C6	118.7 (16)	N4—C12—N5	118.78 (17)
O8'—C13—C14	118.8 (16)	N4—C8—H8	120.00
O7—C13—O8	129.0 (5)	C9—C8—H8	120.00
O7—C13—C14	116.6 (5)	C9—C10—H10	120.00
O7'—C13—O8'	129 (3)	C11—C10—H10	120.00
O7'—C13—C14	113 (2)	C10—C11—H11	120.00
O8—C13—C14	114.4 (3)	C12—C11—H11	120.00
C1—N1—C5—C4	−1.6 (3)	O8—C13—C14—F6	47.9 (4)
C1—N1—C5—N2	179.07 (18)	O7—C13—C14—F4	−9.0 (5)
C5—N1—C1—C2	1.2 (3)	O8—C13—C14—F4	172.6 (4)
O2—N3—C2—C1	−174.9 (2)	O8—C13—C14—F5	−68.3 (4)
O1—N3—C2—C1	4.7 (3)	O7—C13—C14—F5	110.1 (5)
O2—N3—C2—C3	6.5 (3)	O7—C13—C14—F6	−133.7 (5)
O1—N3—C2—C3	−173.9 (2)	N1—C1—C2—N3	−178.84 (17)
C12—N4—C8—C9	−0.5 (3)	N1—C1—C2—C3	−0.3 (3)
C8—N4—C12—C11	1.9 (3)	C1—C2—C3—C4	−0.2 (3)
C8—N4—C12—N5	−176.76 (19)	N3—C2—C3—C4	178.37 (19)
O5—N6—C9—C10	167.4 (2)	C2—C3—C4—C5	−0.3 (3)
O5—N6—C9—C8	−11.3 (3)	C3—C4—C5—N1	1.1 (3)
O6—N6—C9—C10	−11.8 (3)	C3—C4—C5—N2	−179.6 (2)
O6—N6—C9—C8	169.47 (19)	N4—C8—C9—C10	−1.1 (3)
O4'—C6—C7—F3'	138.5 (7)	N4—C8—C9—N6	177.59 (17)
O4'—C6—C7—F1'	19.7 (7)	C8—C9—C10—C11	1.2 (3)
O3'—C6—C7—F2'	79.7 (3)	N6—C9—C10—C11	−177.44 (19)
O4'—C6—C7—F2'	−101.6 (7)	C9—C10—C11—C12	0.2 (3)
O3'—C6—C7—F1'	−159.0 (3)	C10—C11—C12—N5	176.9 (2)
O3'—C6—C7—F3'	−40.3 (3)	C10—C11—C12—N4	−1.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4′i	0.86	1.90	2.758 (12)	175
N2—H2A···O3′i	0.93 (2)	1.88 (2)	2.791 (4)	168 (2)
N2—H2B···O8ii	0.90 (2)	2.06 (2)	2.935 (7)	166 (2)
N4—H4A···O8iii	0.86	1.91	2.772 (7)	175
N5—H5A···O7iii	0.91 (2)	1.86 (2)	2.763 (9)	172 (2)
N5—H5B···O3′iv	0.87 (2)	1.97 (2)	2.801 (3)	160 (2)
C1—H1···O7v	0.93	2.36	3.140 (5)	141
C4—H4···O2iv	0.93	2.57	3.264 (3)	132
C8—H8···F1′vi	0.93	2.44	3.089 (3)	127
C8—H8···O4′vi	0.93	2.36	3.253 (7)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4′i	0.86	1.90	2.758 (12)	175
N2—H2A⋯O3′i	0.93 (2)	1.88 (2)	2.791 (4)	168 (2)
N2—H2B⋯O8ii	0.90 (2)	2.06 (2)	2.935 (7)	166 (2)
N4—H4A⋯O8iii	0.86	1.91	2.772 (7)	175
N5—H5A⋯O7iii	0.91 (2)	1.86 (2)	2.763 (9)	172 (2)
N5—H5B⋯O3′iv	0.87 (2)	1.97 (2)	2.801 (3)	160 (2)
C1—H1⋯O7v	0.93	2.36	3.140 (5)	141
C4—H4⋯O2iv	0.93	2.57	3.264 (3)	132
C8—H8⋯F1′vi	0.93	2.44	3.089 (3)	127
C8—H8⋯O4′vi	0.93	2.36	3.253 (7)	161

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