3-(2-Hydroxy­ethyl)-2-(p-tolyl­amino)­quinazolin-4(3H)-one

Zhang, G.-F.; Ma, Z.; Yang, X.-H.

doi:10.1107/S1600536808040440

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Pages o34-o35

doi:10.1107/S1600536808040440

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3-(2-Hydroxyethyl)-2-(p-tolylamino)quinazolin-4(3H)-one

Gui-Fu Zhang,^a Zuan Ma ^b and Xu-Hong Yang ^a ^*

^aDepartment of Chemistry and Life Science, Xianning College, Xianning 4371000, Hubei, People's Republic of China, and ^bDepartment of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, Hubei, People's Republic of China
^*Correspondence e-mail: xhyang8875301@yahoo.com.cn

(Received 30 November 2008; accepted 1 December 2008; online 6 December 2008)

In the title compound, C₁₇H₁₇N₃O₂, the quinazolinone ring system is essentially planar. The benzene ring is twisted with respect to it by a dihedral angle of 32.7 (5)°. The molecular conformation is stabilized by an N—H⋯O hydrogen bond, and the crystal structure is stabilized by intermolecular O—H⋯N interactions.

Related literature

For the biological properties of quinazolinone derivatives, see: Pandeya et al. (1999 ); Shiba et al. (1997 ), Malamas & Millen (1991 ); Mannschreck et al. (1984 ); Kung et al. (1999 ); Bartroli et al. (1998 ); Palmer et al. (1997 ); Tsou et al. (2001 ); Matsuno et al. (2002 ). For the synthesis, see: Yang et al. (2008 ). For related structures, see: Hu et al. (2006 ); Qu et al. (2008 ); Zeng et al. (2008 ); Sun et al. (2008 ).

Experimental

Crystal data

C₁₇H₁₇N₃O₂
M_r = 295.34
Monoclinic, P 2₁ /n
a = 7.8589 (2) Å
b = 19.1706 (5) Å
c = 10.6696 (3) Å
β = 111.082 (3)°
V = 1499.89 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.10 × 0.10 × 0.08 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.981, T_max = 0.993
15404 measured reflections
2938 independent reflections
2074 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.138
S = 1.07
2938 reflections
206 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1D⋯N3ⁱ	0.88 (15)	2.09 (15)	2.882 (12)	149 (13)
N1—H1⋯O1	0.87 (7)	1.98 (8)	2.806 (12)	160 (12)
Symmetry code: (i) -x+2, -y+2, -z+1.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040440/bt2827sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040440/bt2827Isup2.hkl

checkCIF report

Comment top

The synthesis of derivatives of quinazolinone has been the focus of great interest. This is due, in part, to the broad spectrum of biological properties of these compounds. Some of these activities include antimicrobial (Pandeya et al., 1999; Shiba et al., 1997), antidiabetic (Malamas & Millen, 1991), anticonvulsant (Mannschreck et al., 1984), antibacterial (Kung et al., 1999), antifungal (Bartroli et al., 1998), protein tyrosine kinase inhibitors (Palmer et al., 1997), EGFR inhibitors (Tsou et al., 2001) and PDGFR phosphorylation inhibitors (Matsuno et al., 2002). We have recently focused on the synthesis of heterocyclic compounds using an aza-Wittig reaction. The compound (Fig. 1), may be used as a new precursor for obtaining bioactive molecules. The bond lengths and angles are unexceptional. The quinazolinone ring system is almost planar, with a maximum deviation of 0.037Å for N2; the phenyl ring is twisted with respect to it, with a dihedral angle of 32.7 (5)°. Intramolecular N—H···O and intermolecular O—H···N hydrogen bonds (Fig. 2 and Table 2) stabilize the molecular conformation and the crystal structure.

Related literature top

For the biological properties of quinazolinone derivatives, see: Pandeya et al. (1999); Shiba et al. (1997), Malamas et al. (1991); Mannschreck et al. (1984); Kung et al. (1999); Bartroli et al. (1998); Palmer et al. (1997); Tsou et al. (2001); Matsuno et al. (2002). For the synthesis, see: Yang et al. (2008); Hu et al. (2006); Qu et al. (2008); Zeng et al. (2008); Sun et al. (2008).

Experimental top

To a solution of 1-(4-methyl-phenyl)- 3-(2-ethoxycarbonylphenyl) carbodiimide (3 mmol) in THF (15 ml) was added 2-aminoethanol (3 mmol). After the reaction mixture was allowed to stand for 1 h, the solvent was removed and anhydrous ethanol (10 ml) with several drops of EtONa in EtOH was added. The mixture was stirred for 4 h at room temperature. The solution was concentrated under reduced pressure and the residue was recrystallized from ethanol to give the title compound. The product was recrystallized from methanol-dichloromethane (1:1 v/v, 20 ml) at room temperature to give crystals suitable for X-ray diffraction.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top

	Fig. 1. View of the molecular structure of the title compound, showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing of the title compound, showing the hydrogen bonds as dashed lines.

3-(2-Hydroxyethyl)-2-(p-tolylamino)quinazolin-4(3H)-one top

Crystal data top

C₁₇H₁₇N₃O₂	F(000) = 624
M_r = 295.34	D_x = 1.308 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2754 reflections
a = 7.8589 (2) Å	θ = 2.3–23.8°
b = 19.1706 (5) Å	µ = 0.09 mm⁻¹
c = 10.6696 (3) Å	T = 298 K
β = 111.082 (3)°	Block, colorless
V = 1499.89 (8) Å³	0.10 × 0.10 × 0.08 mm
Z = 4

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2938 independent reflections
Radiation source: fine-focus sealed tube	2074 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −9→9
T_min = 0.981, T_max = 0.993	k = −23→23
15404 measured reflections	l = −13→11

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.081P)² + 0.012P] where P = (F_o² + 2F_c²)/3
2938 reflections	(Δ/σ)_max < 0.001
206 parameters	Δρ_max = 0.23 e Å⁻³
2 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₇H₁₇N₃O₂	V = 1499.89 (8) Å³
M_r = 295.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.8589 (2) Å	µ = 0.09 mm⁻¹
b = 19.1706 (5) Å	T = 298 K
c = 10.6696 (3) Å	0.10 × 0.10 × 0.08 mm
β = 111.082 (3)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2938 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	2074 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.993	R_int = 0.037
15404 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	2 restraints
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.23 e Å⁻³
2938 reflections	Δρ_min = −0.17 e Å⁻³
206 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.

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
C1	0.713 (2)	0.6964 (7)	0.4651 (16)	0.077 (5)
H1A	0.5917	0.6810	0.4512	0.116*
H1B	0.7975	0.6738	0.5432	0.116*
H1C	0.7434	0.6846	0.3881	0.116*
C2	0.7255 (16)	0.7741 (6)	0.4853 (13)	0.053 (3)
C3	0.6939 (17)	0.8197 (6)	0.3785 (13)	0.056 (3)
H3	0.6602	0.8019	0.2918	0.068*
C4	0.7113 (16)	0.8908 (6)	0.3978 (11)	0.050 (3)
H4	0.6892	0.9202	0.3243	0.060*
C5	0.7611 (14)	0.9190 (5)	0.5253 (11)	0.042 (3)
C6	0.7883 (15)	0.8745 (6)	0.6330 (12)	0.048 (3)
H6	0.8185	0.8924	0.7193	0.058*
C7	0.7703 (16)	0.8033 (6)	0.6116 (13)	0.053 (3)
H7	0.7891	0.7740	0.6848	0.063*
C8	0.8785 (14)	1.0302 (5)	0.6438 (11)	0.041 (3)
C9	0.9600 (16)	1.1474 (6)	0.7315 (11)	0.047 (3)
C10	1.0902 (15)	1.1136 (6)	0.8487 (11)	0.044 (3)
C11	1.1021 (15)	1.0410 (6)	0.8529 (11)	0.044 (3)
C12	1.2277 (17)	1.0094 (7)	0.9662 (12)	0.059 (3)
H12	1.2365	0.9610	0.9711	0.070*
C13	1.3379 (19)	1.0490 (8)	1.0699 (13)	0.066 (4)
H13	1.4213	1.0272	1.1448	0.080*
C14	1.3277 (19)	1.1213 (7)	1.0656 (12)	0.064 (4)
H14	1.4040	1.1478	1.1366	0.077*
C15	1.2045 (18)	1.1529 (7)	0.9560 (12)	0.057 (3)
H15	1.1965	1.2013	0.9528	0.068*
C16	0.7068 (16)	1.1345 (6)	0.5175 (11)	0.049 (3)
H16A	0.6734	1.1787	0.5463	0.058*
H16B	0.5999	1.1047	0.4912	0.058*
C17	0.7589 (16)	1.1470 (6)	0.3967 (11)	0.051 (3)
H17A	0.6786	1.1817	0.3390	0.061*
H17B	0.8828	1.1645	0.4253	0.061*
N1	0.7697 (13)	0.9925 (5)	0.5361 (9)	0.048 (3)
H1	0.737 (16)	1.015 (6)	0.461 (9)	0.057*
N2	0.8506 (12)	1.1022 (4)	0.6320 (9)	0.042 (2)
N3	0.9966 (12)	0.9998 (5)	0.7464 (9)	0.046 (2)
O1	0.7451 (12)	1.0832 (4)	0.3238 (8)	0.055 (2)
H1D	0.84 (2)	1.074 (7)	0.306 (15)	0.083*
O2	0.9394 (12)	1.2106 (4)	0.7163 (9)	0.064 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.090 (11)	0.048 (8)	0.099 (12)	−0.014 (7)	0.040 (10)	−0.019 (7)
C2	0.049 (7)	0.045 (7)	0.068 (8)	−0.010 (5)	0.025 (6)	−0.011 (6)
C3	0.064 (8)	0.056 (7)	0.054 (8)	−0.018 (6)	0.028 (7)	−0.018 (6)
C4	0.052 (7)	0.051 (7)	0.046 (7)	−0.011 (5)	0.018 (6)	−0.003 (5)
C5	0.037 (6)	0.040 (6)	0.046 (6)	−0.009 (4)	0.013 (5)	−0.003 (5)
C6	0.051 (7)	0.047 (7)	0.046 (6)	−0.010 (5)	0.016 (6)	−0.006 (5)
C7	0.052 (8)	0.045 (7)	0.059 (8)	−0.008 (5)	0.018 (6)	0.004 (5)
C8	0.041 (6)	0.037 (6)	0.044 (6)	−0.003 (5)	0.015 (5)	−0.004 (5)
C9	0.056 (7)	0.038 (6)	0.051 (7)	−0.001 (5)	0.025 (6)	−0.008 (5)
C10	0.049 (7)	0.041 (6)	0.043 (6)	−0.004 (5)	0.020 (5)	−0.007 (5)
C11	0.045 (7)	0.045 (6)	0.040 (6)	−0.003 (5)	0.013 (5)	−0.006 (5)
C12	0.066 (8)	0.052 (7)	0.047 (7)	0.001 (6)	0.007 (6)	0.000 (5)
C13	0.065 (9)	0.075 (9)	0.045 (7)	−0.002 (7)	0.002 (7)	−0.005 (6)
C14	0.070 (9)	0.070 (9)	0.044 (7)	−0.016 (7)	0.010 (7)	−0.015 (6)
C15	0.069 (9)	0.049 (7)	0.052 (7)	−0.011 (6)	0.022 (7)	−0.014 (6)
C16	0.043 (7)	0.044 (6)	0.055 (7)	0.009 (5)	0.013 (6)	0.001 (5)
C17	0.052 (7)	0.043 (6)	0.047 (7)	0.005 (5)	0.007 (6)	0.003 (5)
N1	0.052 (6)	0.040 (5)	0.041 (5)	−0.005 (4)	0.006 (5)	0.000 (4)
N2	0.043 (5)	0.037 (5)	0.044 (5)	0.003 (4)	0.014 (4)	−0.001 (4)
N3	0.050 (6)	0.037 (5)	0.043 (5)	−0.001 (4)	0.007 (5)	−0.003 (4)
O1	0.060 (6)	0.053 (5)	0.049 (5)	0.005 (4)	0.015 (4)	−0.003 (4)
O2	0.083 (7)	0.035 (5)	0.069 (6)	0.005 (4)	0.020 (5)	−0.006 (4)

Geometric parameters (Å, º) top

C1—C2	1.505 (17)	C10—C11	1.394 (15)
C1—H1A	0.9600	C10—C15	1.394 (15)
C1—H1B	0.9600	C11—N3	1.388 (14)
C1—H1C	0.9600	C11—C12	1.395 (16)
C2—C7	1.382 (17)	C12—C13	1.365 (17)
C2—C3	1.385 (18)	C12—H12	0.9300
C3—C4	1.380 (16)	C13—C14	1.387 (19)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.383 (15)	C14—C15	1.363 (18)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.384 (15)	C15—H15	0.9300
C5—N1	1.414 (13)	C16—N2	1.470 (14)
C6—C7	1.383 (15)	C16—C17	1.506 (16)
C6—H6	0.9300	C16—H16A	0.9700
C7—H7	0.9300	C16—H16B	0.9700
C8—N3	1.292 (14)	C17—O1	1.432 (13)
C8—N1	1.366 (14)	C17—H17A	0.9700
C8—N2	1.395 (13)	C17—H17B	0.9700
C9—O2	1.225 (13)	N1—H1	0.87 (7)
C9—N2	1.401 (14)	O1—H1D	0.88 (15)
C9—C10	1.452 (16)

C2—C1—H1A	109.5	N3—C11—C12	119.3 (10)
C2—C1—H1B	109.5	C10—C11—C12	118.7 (10)
H1A—C1—H1B	109.5	C13—C12—C11	120.4 (12)
C2—C1—H1C	109.5	C13—C12—H12	119.8
H1A—C1—H1C	109.5	C11—C12—H12	119.8
H1B—C1—H1C	109.5	C12—C13—C14	121.1 (12)
C7—C2—C3	117.0 (11)	C12—C13—H13	119.5
C7—C2—C1	121.4 (12)	C14—C13—H13	119.5
C3—C2—C1	121.5 (12)	C15—C14—C13	119.2 (11)
C4—C3—C2	121.4 (11)	C15—C14—H14	120.4
C4—C3—H3	119.3	C13—C14—H14	120.4
C2—C3—H3	119.3	C14—C15—C10	120.8 (12)
C3—C4—C5	120.7 (11)	C14—C15—H15	119.6
C3—C4—H4	119.6	C10—C15—H15	119.6
C5—C4—H4	119.6	N2—C16—C17	114.5 (9)
C4—C5—C6	118.7 (10)	N2—C16—H16A	108.6
C4—C5—N1	117.2 (10)	C17—C16—H16A	108.6
C6—C5—N1	123.9 (10)	N2—C16—H16B	108.6
C7—C6—C5	119.6 (11)	C17—C16—H16B	108.6
C7—C6—H6	120.2	H16A—C16—H16B	107.6
C5—C6—H6	120.2	O1—C17—C16	109.8 (9)
C2—C7—C6	122.4 (11)	O1—C17—H17A	109.7
C2—C7—H7	118.8	C16—C17—H17A	109.7
C6—C7—H7	118.8	O1—C17—H17B	109.7
N3—C8—N1	121.1 (10)	C16—C17—H17B	109.7
N3—C8—N2	124.4 (9)	H17A—C17—H17B	108.2
N1—C8—N2	114.6 (9)	C8—N1—C5	126.3 (9)
O2—C9—N2	119.7 (11)	C8—N1—H1	113 (9)
O2—C9—C10	125.0 (10)	C5—N1—H1	116 (8)
N2—C9—C10	115.3 (10)	C8—N2—C9	120.6 (9)
C11—C10—C15	119.8 (11)	C8—N2—C16	122.7 (9)
C11—C10—C9	119.4 (9)	C9—N2—C16	116.6 (9)
C15—C10—C9	120.8 (11)	C8—N3—C11	118.2 (9)
N3—C11—C10	121.9 (10)	C17—O1—H1D	113 (10)

C7—C2—C3—C4	1.7 (18)	C13—C14—C15—C10	0 (2)
C1—C2—C3—C4	−177.7 (11)	C11—C10—C15—C14	−0.2 (18)
C2—C3—C4—C5	0.0 (18)	C9—C10—C15—C14	−179.5 (11)
C3—C4—C5—C6	−1.8 (17)	N2—C16—C17—O1	79.0 (12)
C3—C4—C5—N1	−177.9 (10)	N3—C8—N1—C5	4.7 (17)
C4—C5—C6—C7	1.8 (16)	N2—C8—N1—C5	−175.6 (9)
N1—C5—C6—C7	177.6 (10)	C4—C5—N1—C8	−152.1 (11)
C3—C2—C7—C6	−1.7 (18)	C6—C5—N1—C8	32.0 (17)
C1—C2—C7—C6	177.7 (11)	N3—C8—N2—C9	3.5 (15)
C5—C6—C7—C2	−0.1 (17)	N1—C8—N2—C9	−176.3 (9)
O2—C9—C10—C11	−179.1 (10)	N3—C8—N2—C16	−175.9 (10)
N2—C9—C10—C11	2.0 (14)	N1—C8—N2—C16	4.3 (14)
O2—C9—C10—C15	0.2 (17)	O2—C9—N2—C8	176.4 (10)
N2—C9—C10—C15	−178.7 (10)	C10—C9—N2—C8	−4.6 (14)
C15—C10—C11—N3	−177.3 (10)	O2—C9—N2—C16	−4.1 (15)
C9—C10—C11—N3	2.0 (15)	C10—C9—N2—C16	174.9 (9)
C15—C10—C11—C12	0.8 (16)	C17—C16—N2—C8	−84.7 (12)
C9—C10—C11—C12	−179.9 (10)	C17—C16—N2—C9	95.9 (11)
N3—C11—C12—C13	177.4 (12)	N1—C8—N3—C11	−179.6 (9)
C10—C11—C12—C13	−0.7 (18)	N2—C8—N3—C11	0.7 (16)
C11—C12—C13—C14	0 (2)	C10—C11—N3—C8	−3.4 (16)
C12—C13—C14—C15	0 (2)	C12—C11—N3—C8	178.5 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···N3ⁱ	0.88 (15)	2.09 (15)	2.882 (12)	149 (13)
N1—H1···O1	0.87 (7)	1.98 (8)	2.806 (12)	160 (12)

Symmetry code: (i) −x+2, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇N₃O₂
M_r	295.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.8589 (2), 19.1706 (5), 10.6696 (3)
β (°)	111.082 (3)
V (Å³)	1499.89 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.10 × 0.10 × 0.08

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.981, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	15404, 2938, 2074
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.138, 1.07
No. of reflections	2938
No. of parameters	206
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.17

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···N3ⁱ	0.88 (15)	2.09 (15)	2.882 (12)	149 (13)
N1—H1···O1	0.87 (7)	1.98 (8)	2.806 (12)	160 (12)

Symmetry code: (i) −x+2, −y+2, −z+1.

Acknowledgements

The authors are grateful to Xianning College for financial support of this work and for providing laboratory and analytical facilities. The authors also acknowledge Dr Xiang-Gao Meng, Central China Normal University Whuhan, for the data collection.

References

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