(E)-3-Amino-4-(2-phenyl­hydrazinyl­idene)-1H-pyrazol-5(4H)-one

Elgemeie, G.H.; Sayed, S.H.; Jones, P.G.

doi:10.1107/S1600536812050854

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o187

doi:10.1107/S1600536812050854

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ADDENDA AND ERRATA

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(E)-3-Amino-4-(2-phenylhydrazinylidene)-1H-pyrazol-5(4H)-one

Galal H. Elgemeie,^a ^* Shahinaz H. Sayed ^a and Peter G. Jones ^b

^aChemistry Department, Faculty of Science, Helwan University, Cairo, Egypt, and ^bInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Postfach 3329, D-38023 Braunschweig, Germany
^*Correspondence e-mail: elgemeie@yahoo.com

(Received 7 December 2012; accepted 14 December 2012; online 4 January 2013)

The molecule of the title compound, C₉H₉N₅O, is essentially planar (r.m.s. deviation of all atoms = 0.02 Å) except for the NH₂ H atoms. An intramolecular hydrazinylidene–carbonyl N—H⋯O=C hydrogen bond is present. In the crystal, molecules are connected via N—H⋯N/O hydrogen bonds, forming thick layers parallel to (100).

Related literature

The synthesis, chemistry and biological/medical activity of related compounds is described in: Elgemeie (2003 ); Elgemeie & El-Aziz (2002 ); Elgemeie & Sood (2003 , 2006 ); Elgemeie et al. (2001 , 2007 , 2008 , 2009 ).

Experimental

Crystal data

C₉H₉N₅O
M_r = 203.21
Monoclinic, P 2₁ /c
a = 6.7380 (2) Å
b = 13.4310 (4) Å
c = 10.4563 (3) Å
β = 103.094 (3)°
V = 921.67 (5) Å³
Z = 4
Cu Kα radiation
μ = 0.86 mm⁻¹
T = 100 K
0.15 × 0.10 × 0.03 mm

Data collection

Oxford Diffraction Xcalibur (Atlas, Nova) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.668, T_max = 1.000
26682 measured reflections
1914 independent reflections
1807 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.087
S = 1.05
1914 reflections
152 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H01⋯O1ⁱ	0.909 (16)	1.949 (16)	2.8521 (11)	172.0 (14)
N3—H03B⋯N2ⁱⁱ	0.934 (17)	2.424 (16)	3.2711 (12)	150.8 (13)
N3—H03A⋯O1ⁱⁱⁱ	0.908 (16)	2.141 (15)	2.9635 (11)	150.2 (13)
N5—H05⋯O1	0.897 (16)	2.174 (16)	2.8575 (11)	132.5 (13)
Symmetry codes: (i) -x, -y+1, -z; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812050854/gg2105sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812050854/gg2105Isup3.hkl

Supporting information file. DOI: 10.1107/S1600536812050854/gg2105Isup3.cml

checkCIF report

Comment top

Chemically synthesized purine analogues find numerous applications in clinical medicine and medical research (Elgemeie, 2003; Elgemeie et al., 2008). The pharmacological approach involves analogues in which the heterocyclic ring system has been modified so as to induce toxic effects when the analogue is incorporated into specific cell constituents (Elgemeie & El-Aziz, 2002). As part of our program directed towards the synthesis of purines and other antimetabolites (Elgemeie et al., 2001, 2009), we have recently reported various successful approaches to the syntheses of purine analogues. Derivatives of these ring systems are of interest as antimetabolites in biochemical reactions (Elgemeie & Sood, 2003). We have described several novel syntheses of functionalized pyrazoles (Elgemeie et al., 2007). These compounds are considered important intermediates for the synthesis of various purine ring systems (Elgemeie & Sood, 2006). As a continuation of this work, the title pyrazole compound (2), was prepared as a precursor for the synthesis of other purines. 2-Hydrazinyl-2-oxo-N-phenylacetohydrazonoyl cyanide (1) undergoes intramolecular cyclization by refluxing in ethanol containing catalytic amounts of piperidine to give the novel pyrazole derivative (2). The title compound can potentially exist in two other tautomeric forms with hydroxyl groups, (3) and (4). Spectral studies, however, indicated the presence of the ketonic tautomer (2) in solution (e.g. the ¹³C NMR signal at δ = 174.00, indicating a carbonyl carbon rather than C—OH.

The X-ray analysis of (2) (Fig. 1) establishes the exclusive presence of the keto tautomer in the solid state; all H atoms could be located unambiguously and bond lengths are also consistent with the keto form. The entire molecule is planar (r.m.s. deviation of all non-C atoms: 0.02 Å), except for the H atoms of the NH₂ group; H03A lies 0.36 (2) and H03B 0.27 (2) Å outside the plane. Consistent with the E configuration, an intramolecular hydrogen bond N5—H05···O1 is observed.

The molecules are connected by hydrogen bonds #1–#3 to form thick hydrogen-bonded layers parallel to (100); the individual molecules are to a good approximation oriented in the planes (042) (Figs. 2, 3). Hydrogen bond #4 is the second and appreciably less linear branch of a three-centre interaction.

Related literature top

The synthesis, chemistry and biological/medical activity of related compounds is described in: Elgemeie (2003); Elgemeie & El-Aziz (2002); Elgemeie & Sood (2003, 2006); Elgemeie et al. (2001, 2007, 2008, 2009).

Experimental top

The title compound was obtained by refluxing an ethanolic solution of 2-hydrazinyl-2-oxo-N-phenylacetohydrazonoyl cyanide containing a few drops of piperidine for 1 h. After cooling, the precipitate was filtered off and recrystallized from ethanol. Yield (85%); m.p. 245 °C; IR (KBr) ν = 3450, 3350, 3300 (NH₂, NH), 1660 (C═O, s) cm^-1; ¹H NMR (DMSO) δ = 6.88 (s, br, 2H, NH₂), 7.23 (s, br, 1H, NH), 7.41–7.92 (m, 5H, C₆H₅); MS, m/z = 203; Calc. for C₉H₉N₅O: C, 53.19; H, 4.46; N, 34.46; O, 7.87. Found: C, 53.56; H, 4.57; N, 34.62; O, 7.61%.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Ellipsoids represent 50% probability levels.
	Fig. 2. Packing diagram of the title compound projected along the b axis, showing the layer structure side-on.
	Fig. 3. Packing diagram of the title compound, viewed perpendicular to (100). Thick dashed bonds represent classical H bonds. Atom names correspond to the asymmetric unit; hydrogen bonds are numbered according to the Table on page Sup-7 (#4, the weaker part of a three-centre interaction, is omitted, as is the intramolecular interaction #5).
	Fig. 4. The formation of the title compound

(E)-3-Amino-4-(2-phenylhydrazinylidene)-1H- pyrazol-5(4H)-one top

Crystal data top

C₉H₉N₅O	F(000) = 424
M_r = 203.21	D_x = 1.464 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 518 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 6.7380 (2) Å	Cell parameters from 18413 reflections
b = 13.4310 (4) Å	θ = 3.3–75.6°
c = 10.4563 (3) Å	µ = 0.86 mm⁻¹
β = 103.094 (3)°	T = 100 K
V = 921.67 (5) Å³	Tablet, orange-brown
Z = 4	0.15 × 0.10 × 0.03 mm

Data collection top

Oxford Diffraction Xcalibur (Atlas, Nova) diffractometer	1914 independent reflections
Radiation source: Nova (Cu) X-ray Source	1807 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 10.3543 pixels mm^-1	θ_max = 75.8°, θ_min = 5.5°
ω–scan	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −16→16
T_min = 0.668, T_max = 1.000	l = −13→13
26682 measured reflections

Refinement top

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0473P)² + 0.2869P] where P = (F_o² + 2F_c²)/3
1914 reflections	(Δ/σ)_max < 0.001
152 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₉H₉N₅O	V = 921.67 (5) Å³
M_r = 203.21	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 6.7380 (2) Å	µ = 0.86 mm⁻¹
b = 13.4310 (4) Å	T = 100 K
c = 10.4563 (3) Å	0.15 × 0.10 × 0.03 mm
β = 103.094 (3)°

Data collection top

Oxford Diffraction Xcalibur (Atlas, Nova) diffractometer	1914 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1807 reflections with I > 2σ(I)
T_min = 0.668, T_max = 1.000	R_int = 0.029
26682 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.17 e Å⁻³
1914 reflections	Δρ_min = −0.26 e Å⁻³
152 parameters

Special details top

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 6.7047 (0.0004) x + 0.5009 (0.0024) y + 3.2946 (0.0013) z = 0.2057 (0.0017)

* -0.0265 (0.0007) O1 * -0.0015 (0.0008) N1 * 0.0248 (0.0008) N2 * 0.0064 (0.0007) N3 * -0.0035 (0.0008) N4 * 0.0047 (0.0008) N5 * 0.0127 (0.0009) C3 * -0.0173 (0.0009) C4 * -0.0155 (0.0009) C5 * 0.0096 (0.0009) C11 * 0.0334 (0.0009) C12 * 0.0207 (0.0009) C13 * -0.0104 (0.0009) C14 * -0.0239 (0.0009) C15 * -0.0136 (0.0009) C16 0.3618 (0.0145) H03A 0.2676 (0.0152) H03B

Rms deviation of fitted atoms = 0.0175

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.09284 (11)	0.44649 (5)	0.17545 (7)	0.02234 (19)
N1	0.06030 (14)	0.60858 (6)	0.09217 (8)	0.0210 (2)
H01	0.008 (2)	0.5972 (11)	0.0053 (16)	0.036 (4)*
N2	0.08679 (13)	0.70841 (6)	0.13887 (8)	0.0210 (2)
C3	0.15061 (15)	0.70044 (7)	0.26628 (10)	0.0188 (2)
C4	0.16773 (15)	0.59729 (7)	0.30772 (10)	0.0182 (2)
C5	0.10365 (15)	0.53946 (8)	0.18664 (9)	0.0190 (2)
N3	0.19896 (14)	0.77858 (7)	0.35089 (9)	0.0230 (2)
H03B	0.202 (2)	0.7633 (12)	0.4385 (16)	0.041 (4)*
H03A	0.135 (2)	0.8364 (12)	0.3206 (15)	0.036 (4)*
N4	0.22316 (12)	0.56774 (6)	0.42917 (8)	0.0180 (2)
N5	0.22648 (13)	0.47167 (6)	0.45303 (8)	0.0193 (2)
H05	0.189 (2)	0.4280 (12)	0.3870 (15)	0.034 (4)*
C11	0.28700 (14)	0.43692 (8)	0.58298 (10)	0.0190 (2)
C12	0.28637 (16)	0.33470 (8)	0.60446 (11)	0.0229 (2)
H12	0.2442	0.2901	0.5329	0.028*
C13	0.34813 (16)	0.29858 (8)	0.73178 (11)	0.0268 (3)
H13	0.3487	0.2289	0.7473	0.032*
C14	0.40897 (16)	0.36360 (9)	0.83626 (11)	0.0283 (3)
H14	0.4516	0.3386	0.9232	0.034*
C15	0.40732 (17)	0.46548 (9)	0.81331 (10)	0.0271 (3)
H15	0.4484	0.5099	0.8851	0.033*
C16	0.34645 (16)	0.50330 (8)	0.68682 (10)	0.0223 (2)
H16	0.3454	0.5730	0.6715	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0293 (4)	0.0182 (4)	0.0181 (4)	−0.0032 (3)	0.0024 (3)	−0.0003 (3)
N1	0.0273 (5)	0.0194 (4)	0.0149 (4)	−0.0021 (3)	0.0018 (3)	0.0002 (3)
N2	0.0249 (4)	0.0182 (4)	0.0193 (4)	−0.0005 (3)	0.0038 (3)	0.0006 (3)
C3	0.0188 (5)	0.0190 (5)	0.0189 (5)	0.0015 (4)	0.0045 (4)	0.0008 (4)
C4	0.0188 (5)	0.0189 (5)	0.0166 (5)	0.0006 (4)	0.0036 (4)	−0.0002 (4)
C5	0.0199 (5)	0.0205 (5)	0.0164 (5)	−0.0012 (4)	0.0038 (4)	0.0008 (4)
N3	0.0310 (5)	0.0173 (4)	0.0199 (4)	0.0032 (4)	0.0042 (4)	−0.0004 (3)
N4	0.0190 (4)	0.0179 (4)	0.0172 (4)	0.0019 (3)	0.0042 (3)	0.0012 (3)
N5	0.0237 (4)	0.0178 (4)	0.0155 (4)	0.0001 (3)	0.0028 (3)	−0.0002 (3)
C11	0.0170 (4)	0.0228 (5)	0.0170 (5)	0.0015 (4)	0.0039 (4)	0.0034 (4)
C12	0.0216 (5)	0.0225 (5)	0.0246 (5)	0.0002 (4)	0.0049 (4)	0.0016 (4)
C13	0.0229 (5)	0.0262 (6)	0.0316 (6)	0.0021 (4)	0.0071 (4)	0.0107 (4)
C14	0.0239 (5)	0.0384 (7)	0.0220 (5)	0.0025 (5)	0.0040 (4)	0.0111 (5)
C15	0.0272 (5)	0.0360 (6)	0.0175 (5)	−0.0002 (5)	0.0034 (4)	0.0008 (4)
C16	0.0238 (5)	0.0242 (5)	0.0188 (5)	0.0006 (4)	0.0045 (4)	0.0010 (4)

Geometric parameters (Å, º) top

O1—C5	1.2548 (13)	C13—C14	1.3861 (17)
N1—C5	1.3387 (13)	C14—C15	1.3890 (17)
N1—N2	1.4242 (12)	C15—C16	1.3891 (15)
N2—C3	1.3083 (13)	N1—H01	0.909 (16)
C3—N3	1.3637 (13)	N3—H03B	0.934 (17)
C3—C4	1.4484 (13)	N3—H03A	0.908 (16)
C4—N4	1.3019 (13)	N5—H05	0.897 (16)
C4—C5	1.4645 (13)	C12—H12	0.9500
N4—N5	1.3134 (12)	C13—H13	0.9500
N5—C11	1.4069 (13)	C14—H14	0.9500
C11—C12	1.3914 (15)	C15—H15	0.9500
C11—C16	1.3918 (15)	C16—H16	0.9500
C12—C13	1.3892 (15)

C5—N1—N2	114.23 (8)	C14—C15—C16	120.92 (10)
C3—N2—N1	105.00 (8)	C15—C16—C11	118.64 (10)
N2—C3—N3	124.94 (9)	C5—N1—H01	126.2 (10)
N2—C3—C4	111.62 (9)	N2—N1—H01	119.4 (10)
N3—C3—C4	123.43 (9)	C3—N3—H03B	114.5 (10)
N4—C4—C3	124.69 (9)	C3—N3—H03A	114.0 (9)
N4—C4—C5	130.16 (9)	H03B—N3—H03A	115.7 (14)
C3—C4—C5	105.11 (8)	N4—N5—H05	120.4 (10)
O1—C5—N1	128.54 (9)	C11—N5—H05	119.7 (10)
O1—C5—C4	127.43 (9)	C13—C12—H12	120.4
N1—C5—C4	104.03 (9)	C11—C12—H12	120.4
C4—N4—N5	118.26 (9)	C14—C13—H13	119.8
N4—N5—C11	119.87 (8)	C12—C13—H13	119.8
C12—C11—C16	121.13 (9)	C13—C14—H14	120.2
C12—C11—N5	118.19 (9)	C15—C14—H14	120.2
C16—C11—N5	120.67 (9)	C14—C15—H15	119.5
C13—C12—C11	119.21 (10)	C16—C15—H15	119.5
C14—C13—C12	120.42 (10)	C15—C16—H16	120.7
C13—C14—C15	119.68 (10)	C11—C16—H16	120.7

C5—N1—N2—C3	0.65 (12)	C3—C4—N4—N5	178.06 (9)
N1—N2—C3—N3	178.81 (9)	C5—C4—N4—N5	0.52 (16)
N1—N2—C3—C4	−0.17 (11)	C4—N4—N5—C11	179.53 (9)
N2—C3—C4—N4	−178.34 (9)	N4—N5—C11—C12	179.30 (8)
N3—C3—C4—N4	2.66 (16)	N4—N5—C11—C16	−0.93 (14)
N2—C3—C4—C5	−0.29 (12)	C16—C11—C12—C13	−0.62 (15)
N3—C3—C4—C5	−179.29 (9)	N5—C11—C12—C13	179.15 (9)
N2—N1—C5—O1	179.27 (9)	C11—C12—C13—C14	0.23 (16)
N2—N1—C5—C4	−0.81 (11)	C12—C13—C14—C15	0.24 (16)
N4—C4—C5—O1	−1.54 (18)	C13—C14—C15—C16	−0.33 (17)
C3—C4—C5—O1	−179.44 (10)	C14—C15—C16—C11	−0.05 (16)
N4—C4—C5—N1	178.55 (10)	C12—C11—C16—C15	0.53 (15)
C3—C4—C5—N1	0.65 (10)	N5—C11—C16—C15	−179.24 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···O1ⁱ	0.909 (16)	1.949 (16)	2.8521 (11)	172.0 (14)
N3—H03B···N2ⁱⁱ	0.934 (17)	2.424 (16)	3.2711 (12)	150.8 (13)
N3—H03A···O1ⁱⁱⁱ	0.908 (16)	2.141 (15)	2.9635 (11)	150.2 (13)
N3—H03B···N1ⁱⁱ	0.934 (17)	2.674 (16)	3.2562 (13)	121.1 (12)
N5—H05···O1	0.897 (16)	2.174 (16)	2.8575 (11)	132.5 (13)

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

Experimental details

Crystal data
Chemical formula	C₉H₉N₅O
M_r	203.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	6.7380 (2), 13.4310 (4), 10.4563 (3)
β (°)	103.094 (3)
V (Å³)	921.67 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.86
Crystal size (mm)	0.15 × 0.10 × 0.03

Data collection
Diffractometer	Oxford Diffraction Xcalibur (Atlas, Nova) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.668, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	26682, 1914, 1807
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.087, 1.05
No. of reflections	1914
No. of parameters	152
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.26

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···O1ⁱ	0.909 (16)	1.949 (16)	2.8521 (11)	172.0 (14)
N3—H03B···N2ⁱⁱ	0.934 (17)	2.424 (16)	3.2711 (12)	150.8 (13)
N3—H03A···O1ⁱⁱⁱ	0.908 (16)	2.141 (15)	2.9635 (11)	150.2 (13)
N3—H03B···N1ⁱⁱ	0.934 (17)	2.674 (16)	3.2562 (13)	121.1 (12)
N5—H05···O1	0.897 (16)	2.174 (16)	2.8575 (11)	132.5 (13)

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

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