Oxygen versus nitro­gen inter­actions in lithium dinitramidate dihydrate and pyridinium dinitramidate

The title compounds, diaqua­dinitramidatolithium(I), [Li(N₃O₄)(H₂O)₂], (I), and pyridinium dinitramidate, C₅H₆N⁺·­N₃O₄^-, (II), differ significantly in their cation-anion contacts. The Li⁺ atom of (I) is coordinated by two O atoms of the dinitramide anion in a chelate and by four additional water mol­ecules, with the Li and central N atom of the anion on a twofold rotation axis. The pyridinium cation of (II) exhibits a contact with the dinitramide anion via an inter­molecular N-H...N hydrogen bridge. These inter­actions are compared with those found in reported anhydrous lithium dinitramide and ammonium dinitramide salts.

S1. Comment

The potential coordination modes (Trammell et al., 1996) of dinitramide include monodentate coordination to the central N atom of the dinitramide skeleton, monodentate coordination to one O atom of the nitro groups, and bidentate coordination to two O atoms of the terminal nitro groups. We report here the molecular structures of the dinitramide salts (I) and (II), and compare (I) with its anhydrous homologue and (II) with ammonium dinitramide in terms of cation–anion contacts.

Compound (I) exhibits a distorted octahedral Li⁺ cation with a chelate-type coordination by two O atoms of the dinitramide anion and four additional water molecules (Fig. 1). Analogous to what was observed in the anhydrous compound, Li(N₃O₄) (Gilardi et al., 1997), the Li⁺ atom is located on a twofold rotation axis which also bisects the dinitramide anion. To the best of our knowledge, these two cases present the only examples of imposed C₂ symmetry in a dinitramide. In all other cases, the dinitramide anion has C₁ symmetry, except for 3,3-dinitroazetidinium, where a crystallographically imposed mirror plane passes through the dinitramide anion (Gilardi & Butcher, 1998).

The Li—O distances to the water molecules are 1.960 (4) (Li1–O3) and 2.490 (3) Å [Li1–O3ⁱⁱ; symmetry code: (ii) -x, 1 - y, 1 - z], whereas the distance between the Li⁺ atom and the O atom of the dinitramide moiety is 2.054 (4) Å. In Li(N₃O₄) (Gilardi et al., 1997) the five Li—O distances range from 2.028 (5) to 2.200 (2) Å and are exclusively contacts to O atoms of the dinitramide moiety. Thus, the entire packing in Li(N₃O₄) is based on Li—O(dinitramide) bonding. By contrast, the presence of the coordinated water in (I) allows for the formation of an approximately linear O_water—H···O_dinitramide hydrogen bond which generates by translation a C(5) chain (Etter et al., 1990; Bernstein et al., 1995) running along the [100] direction (Fig. 1).

The dinitramide moiety in (I) is nearly planar, with a twist angle of 2.0°. This is a measure of the degree by which the nitro group has rotated out of the NNN plane (Pinkerton & Ritchie, 2003; Gilardi, et al. 1997) and is significantly smaller than the twist angle of 15.8° in Li(N₃O₄) (Gilardi et al., 1997). The dinitramide moiety has a bend angle of 1.3°, representing the pyramidalization of the nitro N atoms (expected values are 0° for ideal sp² and 54.8° for ideal sp³ conformations), and this value is slightly smaller than the bend angle of 4.6° found in Li(N₃O₄).

The O···O chelate distance in (I) [2.576 (2) Å] is comparable with that reported for Li(N₃O₄) [2.593 Å], while the pseudotorsion angle between the two closest N—O bonds in different nitro groups in the molecule is smaller in (I) [4.4°, versus 29.6° in Li(N₃O₄)].

In contrast with the dinitramide coordination in (I), compound (II) exhibits an intermolecular secondary contact to the central N atom of the dinitramide moiety via an N—H···N hydrogen bond (Fig. 2). The dinitramide anion has C₁ symmetry, with N—N and N—O distances comparable with those in compound (I) and other dinitramide anions (Gilardi et al., 1997; Christe et al., 1996).

The twist and bend angles of the dinitramide moiety tend, as also observed in (I), to a relatively planar conformation (twist angles 4.8 and 5.9°; bend angles 1.5 and 0.4°) and are significantly different from those in ammonium dinitramide (twist angles 25.6 and 20.8°; bend angles 5.1 and 5.3°; Gilardi et al., 1997).

The O···O distance in (II) is slightly smaller than that in the ammonium salt [2.532 (4) versus 2.591 Å, respectively] and the pseudotorsion angle is considerably smaller [9.6 versus 37.9°, respectively].

Atom N4 in the cation of (II) acts as hydrogen-bond donor to atom N1 in the anion, giving rise to an approximately linear N—H···N interaction. Since no further hydrogen bonds are present, the structure of (II) consists of isolated cation–anion pairs with no significant interactions between them. This is in contrast with ammonium dinitramide, where extensive hydrogen bonding involving all four ammonium H atoms furnishes a multi-dimensional hydrogen-bond architecture (Gilardi et al., 1997). The hydrogen bonds are directed tetrahedrally involving exclusively the O atoms of the dinitramide moiety as hydrogen-bond acceptors, with H···O distances in the range 2.153–2.230 Å.

The packing motif in (II) consists of layers lying parallel to the bc plane with different orientations of the cation–anion pairs and a distance of 3.7 Å between those layers along the a axis (Fig. 3).

Related literature

For related literature, see: Ang et al. (2002); Bernstein et al. (1995); Christe et al. (1996); Etter et al. (1990); Gilardi & Butcher (1998); Gilardi et al. (1997); Pinkerton & Ritchie (2003); Trammell et al. (1996).

S2. Experimental

Compound (I) was obtained as a by-product in the preparation of a certain dinitramide salt. A mixture of trimethyltelluronium chloride (1.11 mmol) and [Ag(py)₂][N₃O₄] (1.22 mmol) was dissolved in water (15 ml) and stirred at ambient temperature for 1 h. The resulting precipitate (AgCl) was removed by filtration and all volatile materials of the remaining solution removed in vacuo. Colourless crystals suitable for single-crystal X-ray diffraction were obtained by slow evaporation of a solution in acetone. The presence of lithium in the structure arises from impurities in the starting material [Me₃Te]Cl that result from its preparation via the reaction of TeCl₄ with MeLi, and was proved by ⁷Li NMR spectroscopy (δ -0.99 p.p.m.).

Compound (II) was obtained as a by-product in the attempted preparation of an organodinitramide with the help of [Ag(py)₂][N₃O₄] as a dinitramide transfer reagent (Ang et al., 2002). Single crystals were grown by slow evaporation of a dichloromethane solution.

S3. Refinement

Water H atoms of (I) were located in a difference Fourier map and refined freely with isotropic displacement parameters. The highest peak and deepest hole in the final difference map are located 0.57 Å from N1 and 0.73 Å from N2, respectively. H atoms in (II) were placed in idealized positions and allowed to ride on their respective parent atoms, with C_arom—H = 0.95 and N_arom—H = 0.88 Å, and with U_iso(H) = 1.2U_eq(carrier atom). The highest peak and deepest hole in the final difference map are located 0.72 Å from H2 and 1.24 Å from C1, respectively.

Computing details

For both compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

Fig. 1. A view of the C(5) motif chain in compound (I), running along the a axis. Hydrogen bonds and intermolecular Li···O contacts are shown as dashed lines. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. [Symmetry codes: (i) -x, y, 3/2 - z; (ii) -x, 1 - y, 1 - z; (iii) x, 1 - y, 1/2 + z; (iv) 1/2 - x, 1/2 - y, 2 - z; (v) -1/2 + x, 1/2 - y, -1/2 + z; (vi) -1/2 - x, 1/2 - y, 1 - z.] Fig. 2. A view of the molecular structure of (II), showing the atom labelling scheme and the hydrogen bond (dashed line) between cation and anion. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Fig. 3. A packing diagram for (II), viewed along the a axis, with hydrogen bonds illustrated as dashed lines. Only H atoms involved in hydrogen bonds are shown. [All H atoms appear to be shown - please clarify]

(I) diaquadinitramidatolithium(I)

Crystal data

[Li(N3O4)(H2O)2]	F(000) = 304
Mr = 148.99	Dx = 1.780 (1) Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 448 reflections
a = 12.574 (5) Å	θ = 3.8–30.0°
b = 7.679 (5) Å	µ = 0.19 mm^−1
c = 6.321 (5) Å	T = 200 K
β = 114.351 (5)°	Platelet, colourless
V = 556.0 (6) Å^3	0.13 × 0.10 × 0.02 mm
Z = 4

Data collection

Oxford Xcalibur3 CCD area-detector diffractometer	575 independent reflections
Radiation source: fine-focus sealed tube	312 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 15.9809 pixels mm^-1	θmax = 26.5°, θmin = 4.2°
ω scans	h = −12→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) (empirical (using intensity measurements) absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm)	k = −8→9
Tmin = 0.977, Tmax = 0.999	l = −7→6
1464 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.069	All H-atom parameters refined
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0332P)^2] where P = (Fo^2 + 2Fc^2)/3
575 reflections	(Δ/σ)max < 0.001
55 parameters	Δρmax = 0.20 e Å^−3
2 restraints	Δρmin = −0.23 e Å^−3

Special details

Refinement. Details of H atom refinement: The water H atoms were located in a difference Fourier map, and freely refined with isotropic displacement parameters The highest peak and deepest hole in the final difference map were located 0.57 Å from N1 and 0.73 Å from N2, respectively.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Li1	0.0000	0.4303 (7)	0.7500	0.0582 (17)
N1	0.0000	−0.0305 (3)	0.7500	0.0248 (6)
N2	0.09544 (13)	0.0627 (2)	0.7629 (3)	0.0257 (4)
O1	0.17636 (10)	−0.03601 (16)	0.7782 (2)	0.0345 (4)
O2	0.10364 (10)	0.22187 (16)	0.7560 (2)	0.0344 (4)
O3	0.10269 (15)	0.5906 (2)	0.6806 (3)	0.0417 (5)
H1	0.175 (2)	0.557 (3)	0.703 (4)	0.059 (8)*
H2	0.1093 (19)	0.686 (4)	0.730 (4)	0.066 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Li1	0.050 (3)	0.025 (3)	0.110 (5)	0.000	0.043 (3)	0.000
N1	0.0250 (12)	0.0167 (12)	0.0344 (16)	0.000	0.0138 (12)	0.000
N2	0.0288 (9)	0.0245 (9)	0.0238 (11)	0.0020 (8)	0.0107 (7)	−0.0005 (8)
O1	0.0311 (8)	0.0295 (8)	0.0443 (11)	0.0098 (6)	0.0169 (7)	0.0013 (6)
O2	0.0365 (9)	0.0187 (7)	0.0504 (10)	−0.0028 (6)	0.0202 (7)	−0.0012 (7)
O3	0.0374 (10)	0.0220 (9)	0.0663 (13)	−0.0009 (7)	0.0220 (9)	−0.0002 (9)

Geometric parameters (Å, º)

Li1—O3^i	1.960 (4)	N1—N2	1.3707 (18)
Li1—O3	1.960 (4)	N1—N2^i	1.3707 (18)
Li1—O2^i	2.054 (4)	N2—O2	1.229 (2)
Li1—O2	2.054 (4)	N2—O1	1.2403 (18)
Li1—O3^ii	2.490 (3)	O3—Li1^iii	2.490 (3)
Li1—O3^iii	2.490 (3)	O3—H1	0.89 (3)
Li1—Li1^iv	3.337 (4)	O3—H2	0.79 (3)
Li1—Li1^iii	3.337 (4)
O3^i—Li1—O3	102.2 (3)	O3^iii—Li1—Li1^iv	148.57 (14)
O3^i—Li1—O2^i	91.26 (8)	O3^i—Li1—Li1^iii	105.5 (2)
O3—Li1—O2^i	163.03 (17)	O3—Li1—Li1^iii	47.87 (10)
O3^i—Li1—O2	163.03 (17)	O2^i—Li1—Li1^iii	118.69 (14)
O3—Li1—O2	91.26 (8)	O2—Li1—Li1^iii	91.13 (10)
O2^i—Li1—O2	77.6 (2)	O3^ii—Li1—Li1^iii	148.57 (15)
O3^i—Li1—O3^ii	83.59 (10)	O3^iii—Li1—Li1^iii	35.72 (5)
O3—Li1—O3^ii	101.10 (11)	Li1^iv—Li1—Li1^iii	142.6 (3)
O2^i—Li1—O3^ii	90.52 (12)	N2—N1—N2^i	117.0 (2)
O2—Li1—O3^ii	83.71 (11)	O2—N2—O1	122.19 (16)
O3^i—Li1—O3^iii	101.10 (11)	O2—N2—N1	126.98 (16)
O3—Li1—O3^iii	83.59 (10)	O1—N2—N1	110.81 (15)
O2^i—Li1—O3^iii	83.71 (11)	N2—O2—Li1	135.54 (16)
O2—Li1—O3^iii	90.52 (12)	Li1—O3—Li1^iii	96.41 (10)
O3^ii—Li1—O3^iii	172.6 (3)	Li1—O3—H1	120.0 (14)
O3^i—Li1—Li1^iv	47.87 (10)	Li1^iii—O3—H1	101.0 (16)
O3—Li1—Li1^iv	105.5 (2)	Li1—O3—H2	117.7 (18)
O2^i—Li1—Li1^iv	91.13 (10)	Li1^iii—O3—H2	114.7 (19)
O2—Li1—Li1^iv	118.69 (14)	H1—O3—H2	106 (2)
O3^ii—Li1—Li1^iv	35.72 (5)
N2^i—N1—N2—O2	−2.74 (14)	Li1^iv—Li1—O2—N2	81.6 (3)
N2^i—N1—N2—O1	178.70 (16)	Li1^iii—Li1—O2—N2	−122.0 (2)
O1—N2—O2—Li1	−175.83 (13)	O3^i—Li1—O3—Li1^iii	−100.02 (11)
N1—N2—O2—Li1	5.8 (3)	O2^i—Li1—O3—Li1^iii	41.8 (5)
O3^i—Li1—O2—N2	47.3 (6)	O2—Li1—O3—Li1^iii	90.39 (12)
O3—Li1—O2—N2	−169.88 (19)	O3^ii—Li1—O3—Li1^iii	174.2 (2)
O2^i—Li1—O2—N2	−2.84 (15)	O3^iii—Li1—O3—Li1^iii	0.0
O3^ii—Li1—O2—N2	89.1 (2)	Li1^iv—Li1—O3—Li1^iii	−149.3 (2)
O3^iii—Li1—O2—N2	−86.3 (2)

Symmetry codes: (i) −x, y, −z+3/2; (ii) x, −y+1, z+1/2; (iii) −x, −y+1, −z+1; (iv) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O1^v	0.89 (3)	1.96 (3)	2.852 (2)	173 (2)

Symmetry code: (v) −x+1/2, y+1/2, −z+3/2.

(II) pyridinium dinitramidate

Crystal data

C5H6N^+·N3O4^−	F(000) = 384
Mr = 186.13	Dx = 1.585 (1) Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 868 reflections
a = 3.7009 (2) Å	θ = 4.0–30.0°
b = 14.4548 (7) Å	µ = 0.14 mm^−1
c = 14.6214 (8) Å	T = 200 K
β = 94.281 (6)°	Needle, colourless
V = 780.00 (7) Å^3	0.21 × 0.10 × 0.06 mm
Z = 4

Data collection

Oxford Xcalibur3 CCD area-detector diffractometer	1537 independent reflections
Radiation source: fine-focus sealed tube	881 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 15.9809 pixels mm^-1	θmax = 26.0°, θmin = 4.0°
ω scans	h = −4→2
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) (empirical (using intensity measurements) absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm)	k = −17→17
Tmin = 0.982, Tmax = 0.995	l = −17→17
3991 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.077	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.032P)^2] where P = (Fo^2 + 2Fc^2)/3
1537 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.12 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

Refinement. Details of H atom refinement: H atoms were placed in idealized positions and allowed to ride on their respective parent atoms, with C_arom–H = 0.95 and N_arom–H = 0.88 Å, and with U_iso(H) = kU_eq(carrier atom), where k = 1.2 for CH. The highest peak and deepest hole in the final difference map were located 0.72 Å from H2 and 1.24 Å from C1, respectively.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.6253 (5)	0.43555 (11)	0.69643 (10)	0.0399 (5)
N2	0.5614 (5)	0.52747 (14)	0.67356 (12)	0.0447 (5)
O1	0.3597 (5)	0.53381 (10)	0.60286 (10)	0.0626 (5)
O2	0.6900 (5)	0.59413 (10)	0.71511 (10)	0.0680 (6)
N3	0.8279 (5)	0.41827 (13)	0.77710 (11)	0.0421 (5)
O3	0.8931 (4)	0.33517 (10)	0.78669 (9)	0.0567 (5)
O4	0.9302 (5)	0.47668 (11)	0.83292 (11)	0.0703 (5)
N4	0.2594 (4)	0.29446 (13)	0.59717 (12)	0.0409 (5)
H4A	0.3636	0.3364	0.6340	0.049*
C1	0.1227 (6)	0.32031 (14)	0.51406 (15)	0.0415 (6)
H1	0.1375	0.3830	0.4952	0.050*
C2	−0.0385 (5)	0.25588 (15)	0.45651 (14)	0.0424 (6)
H2	−0.1353	0.2731	0.3969	0.051*
C3	−0.0594 (6)	0.16640 (15)	0.48540 (16)	0.0433 (6)
H3	−0.1722	0.1211	0.4458	0.052*
C4	0.0824 (6)	0.14153 (14)	0.57159 (15)	0.0456 (6)
H4	0.0676	0.0795	0.5923	0.055*
C5	0.2437 (5)	0.20785 (16)	0.62622 (14)	0.0436 (6)
H5	0.3460	0.1920	0.6857	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0486 (12)	0.0329 (10)	0.0366 (11)	−0.0033 (8)	−0.0085 (10)	0.0032 (8)
N2	0.0478 (13)	0.0416 (12)	0.0445 (12)	−0.0026 (11)	0.0028 (10)	0.0038 (11)
O1	0.0666 (12)	0.0607 (11)	0.0572 (11)	0.0037 (9)	−0.0175 (10)	0.0120 (9)
O2	0.0967 (15)	0.0389 (10)	0.0672 (12)	−0.0138 (9)	−0.0022 (11)	−0.0084 (9)
N3	0.0381 (12)	0.0477 (13)	0.0403 (12)	0.0005 (10)	0.0009 (10)	−0.0016 (10)
O3	0.0748 (13)	0.0407 (10)	0.0531 (10)	0.0115 (9)	−0.0045 (9)	0.0075 (8)
O4	0.0804 (13)	0.0605 (10)	0.0642 (11)	0.0054 (10)	−0.0339 (10)	−0.0222 (9)
N4	0.0385 (12)	0.0418 (12)	0.0418 (12)	−0.0017 (9)	−0.0001 (10)	−0.0111 (9)
C1	0.0425 (14)	0.0379 (13)	0.0444 (14)	−0.0018 (11)	0.0055 (12)	0.0066 (12)
C2	0.0409 (15)	0.0528 (15)	0.0326 (13)	0.0039 (12)	−0.0037 (11)	−0.0003 (12)
C3	0.0350 (14)	0.0457 (15)	0.0490 (15)	−0.0030 (11)	0.0015 (12)	−0.0116 (12)
C4	0.0447 (14)	0.0354 (14)	0.0564 (16)	0.0002 (11)	0.0033 (13)	0.0040 (12)
C5	0.0383 (15)	0.0533 (15)	0.0386 (13)	0.0070 (12)	−0.0012 (12)	0.0028 (13)

Geometric parameters (Å, º)

N1—N3	1.372 (2)	N4—H4A	0.8800
N1—N2	1.386 (2)	C1—C2	1.363 (3)
N2—O2	1.2169 (19)	C1—H1	0.9500
N2—O1	1.2326 (19)	C2—C3	1.365 (3)
N2—N1	1.386 (2)	C2—H2	0.9500
N3—O4	1.2150 (19)	C3—C4	1.376 (3)
N3—O3	1.2312 (18)	C3—H3	0.9500
N3—N1	1.372 (2)	C4—C5	1.357 (3)
N4—C5	1.325 (2)	C4—H4	0.9500
N4—C1	1.334 (2)	C5—H5	0.9500
N3—N1—N2	117.01 (16)	N4—C1—H1	120.3
O2—N2—O1	123.34 (19)	C2—C1—H1	120.3
O2—N2—N1	125.82 (17)	C1—C2—C3	119.3 (2)
O1—N2—N1	110.82 (18)	C1—C2—H2	120.4
O2—N2—N1	125.82 (17)	C3—C2—H2	120.4
O1—N2—N1	110.82 (18)	C2—C3—C4	120.31 (19)
O4—N3—O3	123.56 (18)	C2—C3—H3	119.8
O4—N3—N1	125.01 (18)	C4—C3—H3	119.8
O3—N3—N1	111.43 (16)	C5—C4—C3	118.4 (2)
O4—N3—N1	125.01 (18)	C5—C4—H4	120.8
O3—N3—N1	111.43 (16)	C3—C4—H4	120.8
C5—N4—C1	122.27 (17)	N4—C5—C4	120.4 (2)
C5—N4—H4A	118.9	N4—C5—H5	119.8
C1—N4—H4A	118.9	C4—C5—H5	119.8
N4—C1—C2	119.32 (19)
N3—N1—N2—O2	5.6 (3)	N4—C1—C2—C3	0.5 (3)
N3—N1—N2—O1	−175.99 (17)	C1—C2—C3—C4	−0.3 (3)
N2—N1—N3—O4	6.1 (3)	C2—C3—C4—C5	−0.4 (3)
N2—N1—N3—O3	−174.32 (17)	C1—N4—C5—C4	−0.5 (3)
C5—N4—C1—C2	−0.1 (3)	C3—C4—C5—N4	0.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N1	0.88	1.92	2.794 (2)	171