N-(5-Nitro-1,3-thia-zol-2-yl)-4-(tri-fluoro-meth-yl)benzamide.

There are two independent and conformationally dissimilar mol-ecules (A and B) in the asymmetric unit of the title compound, C11H6F3N3O3S; the dihedral angles between the benzene and thia-zole rings are 33.8 (2)° in A and 59.7 (2)° in B. The similarity of the C-N bond lengths in the amide group [1.379 (5) and 1.358 (5) Å for A, and 1.365 (5) and 1.363 (5) Å for B] indicates the presence of conjugation between the two rings. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds, forming chains extending along [010]; weak N-H⋯Oamide inter-actions are also present in the structure.

Related literature

For the anti­parasitic activity of nitazoxanide, see: Fox & Saravolatz (2005 ▶) and for the anti­bacterial activity of thia­zolides, see: Gargala et al. (2010 ▶); Stachulski et al. (2011 ▶). For the synthesis and anti­bacterial activity of the title compound, see: Ballard et al. (2011 ▶).

Experimental

Crystal data

C11H6F3N3O3S

M = 317.26

Monoclinic,

a = 12.362 (4) Å

b = 8.946 (3) Å

c = 23.261 (8) Å

β = 100.762 (4)°

V = 2527.2 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.34 × 0.32 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.903, T max = 0.927

11671 measured reflections

4588 independent reflections

3183 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.175

S = 1.06

4588 reflections

379 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813011264/zs2257sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011264/zs2257Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011264/zs2257Isup3.cml

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

C11H6F3N3O3S	F(000) = 1280
Mr = 317.26	Dx = 1.668 Mg m−3
Monoclinic, P21/c	Melting point = 487–489 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.362 (4) Å	Cell parameters from 2723 reflections
b = 8.946 (3) Å	θ = 2.4–24.6°
c = 23.261 (8) Å	µ = 0.31 mm−1
β = 100.762 (4)°	T = 296 K
V = 2527.2 (15) Å3	Block, colourless
Z = 8	0.34 × 0.32 × 0.25 mm

Bruker APEXII CCD diffractometer	4588 independent reflections
Radiation source: fine-focus sealed tube	3183 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.903, Tmax = 0.927	k = −9→10
11671 measured reflections	l = −28→26

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0692P)2 + 3.2322P] where P = (Fo2 + 2Fc2)/3
4588 reflections	(Δ/σ)max = 0.001
379 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

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
C1	0.2871 (3)	0.2306 (5)	0.10652 (16)	0.0387 (10)
C2	0.2390 (3)	0.1247 (5)	0.06679 (17)	0.0448 (11)
H2	0.1799	0.0687	0.0743	0.054*
C3	0.2787 (4)	0.1018 (5)	0.01590 (18)	0.0483 (11)
H3	0.2467	0.0296	−0.0107	0.058*
C4	0.3654 (3)	0.1855 (5)	0.00447 (18)	0.0471 (11)
C5	0.4138 (4)	0.2911 (6)	0.0439 (2)	0.0549 (13)
H5	0.4721	0.3481	0.0360	0.066*
C6	0.3758 (3)	0.3125 (5)	0.09514 (19)	0.0498 (12)
H6	0.4098	0.3821	0.1223	0.060*
C7	0.4053 (5)	0.1639 (8)	−0.0515 (2)	0.0687 (16)
C8	0.2493 (3)	0.2599 (5)	0.16232 (17)	0.0391 (10)
C9	0.0895 (3)	0.2764 (5)	0.20673 (16)	0.0357 (9)
C10	−0.0463 (4)	0.3137 (5)	0.25281 (17)	0.0459 (11)
H10	−0.1190	0.3152	0.2583	0.055*
C11	0.0372 (3)	0.3595 (5)	0.29379 (16)	0.0388 (10)
C12	0.3086 (3)	0.8380 (5)	0.34839 (17)	0.0401 (10)
C13	0.3064 (4)	0.7008 (5)	0.32116 (18)	0.0461 (11)
H13	0.2820	0.6166	0.3384	0.055*
C14	0.3405 (4)	0.6892 (5)	0.26822 (19)	0.0490 (11)
H14	0.3404	0.5965	0.2502	0.059*
C15	0.3746 (3)	0.8129 (5)	0.24206 (18)	0.0436 (10)
C16	0.3762 (4)	0.9502 (6)	0.2691 (2)	0.0554 (12)
H16	0.3984	1.0348	0.2512	0.066*
C17	0.3448 (4)	0.9620 (6)	0.32261 (19)	0.0545 (12)
H17	0.3481	1.0541	0.3414	0.065*
C18	0.4075 (4)	0.8034 (7)	0.1841 (2)	0.0587 (13)
C19	0.2738 (3)	0.8557 (5)	0.40602 (17)	0.0426 (10)
C20	0.1252 (3)	0.8112 (5)	0.45709 (16)	0.0377 (9)
C21	0.0747 (4)	0.8551 (5)	0.54822 (17)	0.0417 (10)
C22	−0.0063 (4)	0.7988 (5)	0.50768 (17)	0.0454 (11)
H22	−0.0763	0.7793	0.5151	0.054*
F1	0.4126 (4)	0.0182 (5)	−0.06394 (15)	0.1155 (15)
F2	0.3376 (3)	0.2148 (5)	−0.09695 (13)	0.0960 (12)
F3	0.5002 (3)	0.2196 (7)	−0.05158 (16)	0.158 (2)
F4	0.4257 (4)	0.6685 (5)	0.16786 (16)	0.1311 (18)
F5	0.3324 (4)	0.8501 (5)	0.14227 (14)	0.1252 (17)
F6	0.4934 (4)	0.8772 (8)	0.18052 (17)	0.184 (3)
N1	0.1382 (3)	0.2403 (4)	0.16086 (13)	0.0382 (8)
H1	0.0982	0.2039	0.1298	0.046*
N2	−0.0176 (3)	0.2646 (4)	0.20246 (14)	0.0445 (9)
N3	0.0305 (3)	0.4175 (4)	0.34971 (15)	0.0446 (9)
N4	0.1728 (3)	0.7979 (4)	0.40900 (13)	0.0416 (9)
H4	0.1375	0.7507	0.3791	0.050*
N5	0.0219 (3)	0.7725 (4)	0.45493 (14)	0.0437 (9)
N6	0.0665 (4)	0.8983 (4)	0.60621 (15)	0.0503 (10)
O1	0.3090 (2)	0.3016 (4)	0.20642 (12)	0.0560 (9)
O2	0.1160 (3)	0.4596 (4)	0.38111 (13)	0.0638 (9)
O3	−0.0597 (3)	0.4226 (4)	0.36369 (13)	0.0587 (9)
O4	0.3288 (2)	0.9184 (4)	0.44772 (13)	0.0632 (10)
O5	0.1513 (3)	0.9334 (4)	0.63961 (14)	0.0713 (11)
O6	−0.0250 (3)	0.8991 (4)	0.61955 (13)	0.0647 (10)
S1	0.16224 (9)	0.34362 (13)	0.27209 (4)	0.0429 (3)
S2	0.19504 (9)	0.88052 (14)	0.52279 (4)	0.0469 (3)

	U11	U22	U33	U12	U13	U23
C1	0.037 (2)	0.045 (3)	0.035 (2)	0.0080 (19)	0.0076 (17)	0.0032 (19)
C2	0.046 (3)	0.046 (3)	0.045 (2)	−0.001 (2)	0.014 (2)	−0.002 (2)
C3	0.051 (3)	0.051 (3)	0.044 (2)	0.002 (2)	0.012 (2)	−0.006 (2)
C4	0.041 (2)	0.062 (3)	0.039 (2)	0.012 (2)	0.0087 (19)	0.004 (2)
C5	0.041 (3)	0.072 (4)	0.056 (3)	−0.003 (2)	0.020 (2)	0.000 (3)
C6	0.041 (2)	0.061 (3)	0.048 (3)	−0.008 (2)	0.010 (2)	−0.011 (2)
C7	0.063 (3)	0.103 (5)	0.046 (3)	0.000 (3)	0.024 (3)	−0.009 (3)
C8	0.041 (2)	0.041 (3)	0.036 (2)	0.0028 (19)	0.0087 (18)	0.0055 (19)
C9	0.043 (2)	0.034 (2)	0.0299 (19)	−0.0021 (18)	0.0073 (17)	0.0037 (17)
C10	0.044 (2)	0.058 (3)	0.037 (2)	0.001 (2)	0.0133 (19)	0.001 (2)
C11	0.048 (2)	0.040 (3)	0.030 (2)	0.0028 (19)	0.0099 (18)	0.0008 (17)
C12	0.030 (2)	0.049 (3)	0.041 (2)	−0.0009 (19)	0.0060 (17)	−0.004 (2)
C13	0.051 (3)	0.044 (3)	0.045 (2)	0.000 (2)	0.016 (2)	0.002 (2)
C14	0.051 (3)	0.048 (3)	0.050 (3)	0.004 (2)	0.016 (2)	−0.006 (2)
C15	0.038 (2)	0.053 (3)	0.040 (2)	0.004 (2)	0.0078 (18)	0.003 (2)
C16	0.064 (3)	0.049 (3)	0.056 (3)	−0.007 (2)	0.018 (2)	0.005 (2)
C17	0.068 (3)	0.047 (3)	0.053 (3)	−0.005 (2)	0.023 (2)	−0.008 (2)
C18	0.059 (3)	0.074 (4)	0.045 (3)	0.003 (3)	0.016 (2)	0.005 (3)
C19	0.039 (2)	0.050 (3)	0.037 (2)	0.002 (2)	0.0039 (18)	−0.003 (2)
C20	0.039 (2)	0.042 (3)	0.031 (2)	0.0013 (19)	0.0056 (17)	−0.0026 (18)
C21	0.056 (3)	0.037 (3)	0.033 (2)	0.001 (2)	0.0115 (19)	0.0004 (18)
C22	0.050 (3)	0.051 (3)	0.039 (2)	0.000 (2)	0.0152 (19)	0.003 (2)
F1	0.169 (4)	0.117 (3)	0.075 (2)	0.048 (3)	0.059 (2)	−0.008 (2)
F2	0.112 (3)	0.133 (3)	0.0448 (17)	0.011 (2)	0.0194 (17)	0.0211 (19)
F3	0.090 (3)	0.313 (7)	0.089 (3)	−0.080 (4)	0.064 (2)	−0.076 (3)
F4	0.226 (5)	0.101 (3)	0.092 (3)	0.061 (3)	0.098 (3)	0.013 (2)
F5	0.147 (4)	0.181 (4)	0.0498 (19)	0.073 (3)	0.024 (2)	0.027 (2)
F6	0.158 (4)	0.329 (8)	0.090 (3)	−0.157 (5)	0.085 (3)	−0.081 (4)
N1	0.0384 (19)	0.046 (2)	0.0310 (17)	−0.0039 (16)	0.0083 (14)	−0.0060 (15)
N2	0.038 (2)	0.062 (3)	0.0349 (18)	−0.0076 (18)	0.0106 (15)	−0.0049 (17)
N3	0.065 (3)	0.036 (2)	0.0355 (19)	0.0040 (18)	0.0157 (19)	0.0006 (16)
N4	0.0377 (19)	0.055 (2)	0.0325 (17)	−0.0058 (16)	0.0077 (14)	−0.0091 (16)
N5	0.044 (2)	0.053 (2)	0.0353 (18)	−0.0043 (18)	0.0119 (15)	−0.0030 (16)
N6	0.081 (3)	0.034 (2)	0.037 (2)	0.002 (2)	0.014 (2)	−0.0004 (17)
O1	0.0428 (17)	0.088 (3)	0.0343 (16)	0.0002 (17)	0.0013 (13)	−0.0087 (16)
O2	0.078 (2)	0.073 (3)	0.0379 (17)	−0.006 (2)	0.0045 (17)	−0.0150 (17)
O3	0.073 (2)	0.056 (2)	0.0556 (19)	0.0123 (17)	0.0336 (17)	−0.0024 (16)
O4	0.0457 (18)	0.097 (3)	0.0468 (18)	−0.0171 (18)	0.0080 (15)	−0.0243 (18)
O5	0.101 (3)	0.070 (3)	0.0410 (18)	−0.009 (2)	0.0067 (19)	−0.0184 (17)
O6	0.092 (3)	0.058 (2)	0.054 (2)	0.0106 (19)	0.0380 (19)	0.0038 (16)
S1	0.0430 (6)	0.0545 (8)	0.0309 (5)	−0.0044 (5)	0.0063 (4)	−0.0053 (5)
S2	0.0490 (7)	0.0570 (8)	0.0335 (5)	−0.0026 (6)	0.0046 (5)	−0.0070 (5)

C1—C2	1.379 (6)	C13—C14	1.378 (6)
C1—C6	1.385 (6)	C13—H13	0.9300
C1—C8	1.483 (5)	C14—C15	1.367 (6)
C2—C3	1.378 (6)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.379 (6)
C3—C4	1.374 (6)	C15—C18	1.482 (6)
C3—H3	0.9300	C16—C17	1.374 (6)
C4—C5	1.375 (6)	C16—H16	0.9300
C4—C7	1.488 (6)	C17—H17	0.9300
C5—C6	1.372 (6)	C18—F6	1.266 (6)
C5—H5	0.9300	C18—F5	1.283 (6)
C6—H6	0.9300	C18—F4	1.297 (6)
C7—F3	1.275 (6)	C19—O4	1.213 (5)
C7—F2	1.303 (6)	C19—N4	1.365 (5)
C7—F1	1.342 (7)	C20—N5	1.314 (5)
C8—O1	1.205 (5)	C20—N4	1.363 (5)
C8—N1	1.379 (5)	C20—S2	1.724 (4)
C9—N2	1.314 (5)	C21—C22	1.339 (6)
C9—N1	1.358 (5)	C21—N6	1.425 (5)
C9—S1	1.723 (4)	C21—S2	1.716 (4)
C10—C11	1.333 (6)	C22—N5	1.358 (5)
C10—N2	1.359 (5)	C22—H22	0.9300
C10—H10	0.9300	N1—H1	0.8600
C11—N3	1.417 (5)	N3—O3	1.220 (4)
C11—S1	1.719 (4)	N3—O2	1.227 (5)
C12—C17	1.375 (6)	N4—H4	0.8600
C12—C13	1.379 (6)	N6—O5	1.224 (5)
C12—C19	1.491 (5)	N6—O6	1.227 (5)
C2—C1—C6	119.5 (4)	C13—C14—H14	119.7
C2—C1—C8	122.8 (4)	C14—C15—C16	119.8 (4)
C6—C1—C8	117.7 (4)	C14—C15—C18	121.3 (4)
C3—C2—C1	120.0 (4)	C16—C15—C18	118.9 (4)
C3—C2—H2	120.0	C17—C16—C15	120.0 (4)
C1—C2—H2	120.0	C17—C16—H16	120.0
C2—C3—C4	120.1 (4)	C15—C16—H16	120.0
C2—C3—H3	120.0	C16—C17—C12	120.2 (4)
C4—C3—H3	120.0	C16—C17—H17	119.9
C5—C4—C3	120.2 (4)	C12—C17—H17	119.9
C5—C4—C7	120.0 (4)	F6—C18—F5	106.1 (5)
C3—C4—C7	119.8 (4)	F6—C18—F4	105.9 (5)
C6—C5—C4	119.9 (4)	F5—C18—F4	102.8 (5)
C6—C5—H5	120.0	F6—C18—C15	114.0 (4)
C4—C5—H5	120.0	F5—C18—C15	112.9 (4)
C5—C6—C1	120.2 (4)	F4—C18—C15	114.2 (4)
C5—C6—H6	119.9	O4—C19—N4	121.1 (4)
C1—C6—H6	119.9	O4—C19—C12	123.8 (4)
F3—C7—F2	108.3 (5)	N4—C19—C12	115.2 (3)
F3—C7—F1	106.3 (5)	N5—C20—N4	120.7 (3)
F2—C7—F1	102.9 (5)	N5—C20—S2	116.8 (3)
F3—C7—C4	114.0 (5)	N4—C20—S2	122.5 (3)
F2—C7—C4	113.4 (4)	C22—C21—N6	126.4 (4)
F1—C7—C4	111.2 (5)	C22—C21—S2	112.9 (3)
O1—C8—N1	120.6 (4)	N6—C21—S2	120.6 (3)
O1—C8—C1	123.9 (4)	C21—C22—N5	114.7 (4)
N1—C8—C1	115.6 (3)	C21—C22—H22	122.7
N2—C9—N1	120.6 (3)	N5—C22—H22	122.7
N2—C9—S1	116.6 (3)	C9—N1—C8	122.4 (3)
N1—C9—S1	122.8 (3)	C9—N1—H1	118.8
C11—C10—N2	115.0 (4)	C8—N1—H1	118.8
C11—C10—H10	122.5	C9—N2—C10	109.3 (3)
N2—C10—H10	122.5	O3—N3—O2	124.0 (4)
C10—C11—N3	126.8 (4)	O3—N3—C11	118.1 (4)
C10—C11—S1	112.6 (3)	O2—N3—C11	117.9 (4)
N3—C11—S1	120.6 (3)	C19—N4—C20	123.2 (3)
C17—C12—C13	119.9 (4)	C19—N4—H4	118.4
C17—C12—C19	118.6 (4)	C20—N4—H4	118.4
C13—C12—C19	121.6 (4)	C20—N5—C22	109.4 (3)
C14—C13—C12	119.6 (4)	O5—N6—O6	124.0 (4)
C14—C13—H13	120.2	O5—N6—C21	117.8 (4)
C12—C13—H13	120.2	O6—N6—C21	118.2 (4)
C15—C14—C13	120.6 (4)	C11—S1—C9	86.47 (19)
C15—C14—H14	119.7	C21—S2—C20	86.26 (19)
C6—C1—C2—C3	−0.6 (6)	C16—C15—C18—F4	166.3 (5)
C8—C1—C2—C3	−179.4 (4)	C17—C12—C19—O4	−50.0 (6)
C1—C2—C3—C4	−0.6 (7)	C13—C12—C19—O4	129.2 (5)
C2—C3—C4—C5	0.7 (7)	C17—C12—C19—N4	129.0 (4)
C2—C3—C4—C7	−177.9 (4)	C13—C12—C19—N4	−51.8 (6)
C3—C4—C5—C6	0.4 (7)	N6—C21—C22—N5	177.4 (4)
C7—C4—C5—C6	179.1 (5)	S2—C21—C22—N5	0.2 (5)
C4—C5—C6—C1	−1.7 (7)	N2—C9—N1—C8	175.9 (4)
C2—C1—C6—C5	1.8 (7)	S1—C9—N1—C8	−2.5 (6)
C8—C1—C6—C5	−179.4 (4)	O1—C8—N1—C9	4.8 (6)
C5—C4—C7—F3	17.1 (8)	C1—C8—N1—C9	−173.6 (4)
C3—C4—C7—F3	−164.2 (5)	N1—C9—N2—C10	−177.1 (4)
C5—C4—C7—F2	−107.4 (6)	S1—C9—N2—C10	1.3 (5)
C3—C4—C7—F2	71.3 (7)	C11—C10—N2—C9	−0.6 (6)
C5—C4—C7—F1	137.3 (5)	C10—C11—N3—O3	2.6 (7)
C3—C4—C7—F1	−44.1 (7)	S1—C11—N3—O3	−178.0 (3)
C2—C1—C8—O1	149.3 (4)	C10—C11—N3—O2	−177.3 (4)
C6—C1—C8—O1	−29.5 (6)	S1—C11—N3—O2	2.1 (5)
C2—C1—C8—N1	−32.4 (6)	O4—C19—N4—C20	2.8 (7)
C6—C1—C8—N1	148.8 (4)	C12—C19—N4—C20	−176.2 (4)
N2—C10—C11—N3	179.1 (4)	N5—C20—N4—C19	170.2 (4)
N2—C10—C11—S1	−0.3 (5)	S2—C20—N4—C19	−9.0 (6)
C17—C12—C13—C14	0.0 (7)	N4—C20—N5—C22	−178.9 (4)
C19—C12—C13—C14	−179.2 (4)	S2—C20—N5—C22	0.4 (5)
C12—C13—C14—C15	−1.2 (7)	C21—C22—N5—C20	−0.3 (6)
C13—C14—C15—C16	0.8 (7)	C22—C21—N6—O5	172.6 (4)
C13—C14—C15—C18	−177.6 (4)	S2—C21—N6—O5	−10.3 (6)
C14—C15—C16—C17	0.8 (7)	C22—C21—N6—O6	−7.9 (7)
C18—C15—C16—C17	179.2 (4)	S2—C21—N6—O6	169.2 (3)
C15—C16—C17—C12	−2.0 (7)	C10—C11—S1—C9	0.8 (4)
C13—C12—C17—C16	1.6 (7)	N3—C11—S1—C9	−178.7 (4)
C19—C12—C17—C16	−179.2 (4)	N2—C9—S1—C11	−1.2 (3)
C14—C15—C18—F6	−137.1 (6)	N1—C9—S1—C11	177.2 (4)
C16—C15—C18—F6	44.5 (7)	C22—C21—S2—C20	0.0 (4)
C14—C15—C18—F5	101.7 (6)	N6—C21—S2—C20	−177.4 (4)
C16—C15—C18—F5	−76.7 (6)	N5—C20—S2—C21	−0.3 (4)
C14—C15—C18—F4	−15.3 (7)	N4—C20—S2—C21	179.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N5i	0.86	2.32	3.044 (5)	142
N1—H1···O3i	0.86	2.57	3.023 (5)	115
N4—H4···N2ii	0.86	2.18	2.939 (5)	147
N4—H4···O2	0.86	2.62	3.146 (5)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N5i	0.86	2.32	3.044 (5)	142
N1—H1⋯O3i	0.86	2.57	3.023 (5)	115
N4—H4⋯N2ii	0.86	2.18	2.939 (5)	147
N4—H4⋯O2	0.86	2.62	3.146 (5)	121

Symmetry codes: (i) ; (ii) .