(E)-Methyl N′-(2-furylmethyl­ene)­hydrazinecarboxyl­ate

Lv, L.-P.; Zhang, Y.-Z.; Ding, X.-M.; Yu, W.-B.; Hu, X.-C.

doi:10.1107/S1600536808033825

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2146

doi:10.1107/S1600536808033825

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(E)-Methyl N′-(2-furylmethylene)hydrazinecarboxylate

Lu-Ping Lv,^a Yong-Zhao Zhang,^a Xiao-Min Ding,^a Wen-Bo Yu ^b and Xian-Chao Hu ^c ^*

^aDepartment of Chemical Engineering, Hangzhou Vocational and Technical College, Hangzhou 310018, People's Republic of China, ^bZhejiang Xinan Chemical Industrial Group Co. Ltd., Jiande 311604, People's Republic of China, and ^cResearch Center of Analysis and Measurement, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: zgdhxc@126.com

(Received 15 October 2008; accepted 16 October 2008; online 22 October 2008)

The title compound, C₇H₈N₂O₃, crystallizes with two independent but essentially identical molecules in the asymmetric unit. Each molecule adopts a trans configuration with respect to the C=N bond. The hydrazinecarboxylate group is twisted from the furan ring by 7.78 (13)° in one molecule and by 7.01 (17)° in the other. In the crystal structure, molecules are linked into chains running along [010] by bifurcated N—H⋯(N,O) and N—H⋯O hydrogen bonds. In addition, weak C—H⋯O interactions and an O⋯C short contact [2.896 (3) Å] are observed.

Related literature

For general background, see: Parashar et al. (1988 ); Hadjoudis et al. (1987 ); Borg et al. (1999 ); Kahwa et al. (1986 ); Santos et al. (2001 ). For a related structure, see: Shang et al. (2007 ).

Experimental

Crystal data

C₇H₈N₂O₃
M_r = 168.15
Monoclinic, C 2
a = 14.9185 (17) Å
b = 7.8124 (9) Å
c = 15.1299 (19) Å
β = 105.251 (7)°
V = 1701.3 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 193 (2) K
0.19 × 0.17 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.978, T_max = 0.982
4679 measured reflections
1601 independent reflections
1399 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.085
S = 1.07
1601 reflections
218 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.09 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O5	0.86	2.36	3.138 (3)	151
N2—H2A⋯N3	0.86	2.52	3.242 (3)	141
N4—H4⋯O2ⁱ	0.86	2.11	2.913 (3)	156
C2—H2⋯O5ⁱⁱ	0.93	2.60	3.521 (4)	172
C10—H10⋯O5ⁱⁱⁱ	0.93	2.59	3.508 (4)	171
Symmetry codes: (i) x, y-1, z; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z]$ ; (iii) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033825/ci2688sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033825/ci2688Isup2.hkl

checkCIF report

Comment top

Benzaldehydehydrazone derivatives have attracted much attention due to their pharmacological activity (Parashar et al., 1988) and their photochromic properties (Hadjoudis et al., 1987). They are important intermidiates of 1,3,4-oxadiazoles, which have been reported to be versatile compounds with many interesting properties (Borg et al., 1999). Metal complexes based on Schiff bases have received considerable attention because they can be utilized as model compounds of active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). We report here the crystal structure of the title compound (Fig. 1).

The title compound contains two independent, but essentially identical molecules in the asymmetric unit. Each independent molecule adopts a trans configuration with respect to the C═N bond. The N1/N2/O2/O3/C6/C7 and N3/N4/O5/O6/C13/C14 planes form dihedral angles of 7.78 (13) and 7.01 (17)°, respectively, with the O1/C1–C4 and O4/C8–C11 planes. The dihedral angle between the two independent furan rings is 85.17 (11)°. The bond lengths and angles are comparable to those observed for methyl N'-[(E)-4-methoxybenzylidene]hydrazinecarboxylate (Shang et al., 2007).

In the crystal structure, the molecules are linked into chains running along the [010] by N—H···O and N—H···N hydrogen bonds (Table 1 and Fig.2). In addition, weak C—H···O interactions and an O4···C5 short contact [2.896 (3) Å] are also observed.

Related literature top

For general background, see: Parashar et al. (1988); Hadjoudis et al. (1987); Borg et al. (1999); Kahwa et al. (1986); Santos et al. (2001). For a related structure, see: Shang et al. (2007).

Experimental top

Furfuraldehyde (0.96 g, 0.01 mol) and methyl hydrazinecarboxylate (0.90 g, 0.01 mol) were dissolved in stirred methanol (20 ml) and left for 3 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 85% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature (m.p. 408–413 K).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.
	Fig. 2. Crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

(E)-Methyl N'-(2-furylmethylene)hydrazinecarboxylate top

Crystal data top

C₇H₈N₂O₃	F(000) = 704
M_r = 168.15	D_x = 1.313 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 1601 reflections
a = 14.9185 (17) Å	θ = 1.4–25.0°
b = 7.8124 (9) Å	µ = 0.10 mm⁻¹
c = 15.1299 (19) Å	T = 193 K
β = 105.251 (7)°	Block, colourless
V = 1701.3 (4) Å³	0.19 × 0.17 × 0.16 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	1601 independent reflections
Radiation source: fine-focus sealed tube	1399 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −17→17
T_min = 0.978, T_max = 0.982	k = −9→8
4679 measured reflections	l = −17→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0464P)² + 0.2178P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
1601 reflections	Δρ_max = 0.10 e Å⁻³
218 parameters	Δρ_min = −0.09 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0051 (9)

Crystal data top

C₇H₈N₂O₃	V = 1701.3 (4) Å³
M_r = 168.15	Z = 8
Monoclinic, C2	Mo Kα radiation
a = 14.9185 (17) Å	µ = 0.10 mm⁻¹
b = 7.8124 (9) Å	T = 193 K
c = 15.1299 (19) Å	0.19 × 0.17 × 0.16 mm
β = 105.251 (7)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1601 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1399 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.982	R_int = 0.020
4679 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	1 restraint
wR(F²) = 0.085	H-atom parameters constrained
S = 1.07	Δρ_max = 0.10 e Å⁻³
1601 reflections	Δρ_min = −0.09 e Å⁻³
218 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	0.6802 (2)	0.5242 (5)	−0.0094 (2)	0.0834 (9)
H1	0.6985	0.4241	−0.0330	0.100*
C2	0.6239 (2)	0.6570 (6)	−0.0595 (2)	0.0971 (12)
H2	0.5969	0.6590	−0.1223	0.117*
C3	0.6170 (2)	0.7771 (6)	0.0000 (2)	0.1020 (12)
H3	0.5850	0.8797	−0.0152	0.122*
C4	0.70165 (17)	0.5730 (4)	0.07936 (17)	0.0617 (7)
C5	0.75360 (16)	0.4883 (3)	0.16066 (17)	0.0583 (6)
H5	0.7769	0.3792	0.1561	0.070*
C6	0.83278 (17)	0.5270 (4)	0.39638 (18)	0.0600 (6)
C7	0.8972 (3)	0.4683 (6)	0.5526 (2)	0.1191 (15)
H7A	0.9269	0.3773	0.5922	0.179*
H7B	0.8411	0.5010	0.5681	0.179*
H7C	0.9383	0.5648	0.5600	0.179*
C8	0.5302 (2)	0.2842 (6)	0.1389 (3)	0.1233 (17)
H8	0.5139	0.3884	0.1093	0.148*
C9	0.4711 (2)	0.1714 (5)	0.1540 (3)	0.0977 (11)
H9	0.4067	0.1801	0.1368	0.117*
C10	0.52379 (19)	0.0344 (5)	0.2012 (2)	0.0786 (8)
H10	0.5006	−0.0642	0.2216	0.094*
C11	0.61376 (17)	0.0724 (3)	0.21148 (18)	0.0615 (7)
C12	0.69799 (17)	−0.0134 (3)	0.25482 (16)	0.0586 (6)
H12	0.6952	−0.1248	0.2756	0.070*
C13	0.93793 (17)	0.0282 (4)	0.32608 (17)	0.0609 (6)
C14	1.0967 (2)	−0.0296 (6)	0.3959 (3)	0.1240 (16)
H14A	1.1351	−0.1178	0.4307	0.186*
H14B	1.1047	0.0743	0.4311	0.186*
H14C	1.1143	−0.0105	0.3400	0.186*
N1	0.76861 (13)	0.5587 (3)	0.23906 (14)	0.0552 (5)
N2	0.81642 (15)	0.4606 (3)	0.31122 (14)	0.0652 (6)
H2A	0.8355	0.3597	0.3025	0.078*
N3	0.77726 (14)	0.0577 (3)	0.26606 (14)	0.0596 (5)
N4	0.85235 (15)	−0.0392 (3)	0.31071 (16)	0.0692 (6)
H4	0.8447	−0.1414	0.3286	0.083*
O1	0.66343 (14)	0.7290 (3)	0.08659 (13)	0.0860 (7)
O2	0.81342 (12)	0.6698 (2)	0.41521 (12)	0.0673 (5)
O3	0.87484 (17)	0.4105 (3)	0.45826 (13)	0.0932 (7)
O4	0.61942 (13)	0.2275 (3)	0.17282 (18)	0.1027 (8)
O5	0.95630 (12)	0.1665 (2)	0.30007 (12)	0.0699 (5)
O6	0.99994 (13)	−0.0822 (3)	0.37459 (16)	0.0895 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0933 (19)	0.090 (2)	0.0653 (18)	−0.024 (2)	0.0181 (15)	−0.0164 (18)
C2	0.090 (2)	0.131 (3)	0.0597 (19)	−0.034 (2)	0.0009 (16)	0.004 (2)
C3	0.097 (2)	0.118 (3)	0.080 (2)	0.012 (2)	0.0033 (18)	0.024 (2)
C4	0.0599 (13)	0.0630 (19)	0.0627 (17)	−0.0120 (13)	0.0170 (11)	−0.0070 (14)
C5	0.0606 (12)	0.0503 (16)	0.0669 (16)	−0.0080 (11)	0.0217 (11)	−0.0033 (13)
C6	0.0688 (14)	0.0525 (16)	0.0598 (16)	0.0034 (12)	0.0191 (11)	0.0131 (13)
C7	0.186 (4)	0.101 (3)	0.063 (2)	0.045 (3)	0.021 (2)	0.022 (2)
C8	0.0559 (16)	0.103 (3)	0.200 (4)	0.0057 (19)	0.014 (2)	0.072 (3)
C9	0.0562 (15)	0.102 (3)	0.129 (3)	−0.0063 (18)	0.0139 (16)	0.034 (3)
C10	0.0716 (16)	0.0723 (18)	0.088 (2)	−0.0234 (16)	0.0139 (14)	0.0125 (16)
C11	0.0673 (15)	0.0484 (16)	0.0684 (16)	−0.0082 (12)	0.0168 (12)	0.0072 (13)
C12	0.0711 (15)	0.0428 (14)	0.0618 (15)	−0.0042 (12)	0.0172 (11)	0.0016 (11)
C13	0.0668 (15)	0.0493 (15)	0.0629 (15)	0.0061 (13)	0.0108 (11)	0.0055 (13)
C14	0.0683 (19)	0.096 (3)	0.185 (4)	0.0045 (19)	−0.007 (2)	0.036 (3)
N1	0.0628 (11)	0.0452 (12)	0.0577 (13)	−0.0017 (9)	0.0159 (9)	0.0039 (10)
N2	0.0882 (15)	0.0433 (11)	0.0659 (14)	0.0111 (11)	0.0237 (11)	0.0071 (11)
N3	0.0637 (12)	0.0448 (12)	0.0693 (13)	0.0024 (10)	0.0158 (10)	0.0078 (10)
N4	0.0663 (12)	0.0437 (11)	0.0940 (16)	0.0038 (10)	0.0148 (11)	0.0182 (12)
O1	0.0971 (14)	0.0878 (16)	0.0700 (13)	0.0182 (12)	0.0162 (10)	0.0062 (11)
O2	0.0868 (12)	0.0485 (11)	0.0639 (11)	0.0061 (10)	0.0154 (9)	0.0031 (9)
O3	0.1460 (19)	0.0685 (15)	0.0641 (12)	0.0357 (14)	0.0256 (12)	0.0230 (11)
O4	0.0575 (10)	0.0748 (14)	0.171 (2)	−0.0016 (10)	0.0218 (12)	0.0520 (15)
O5	0.0733 (10)	0.0521 (11)	0.0783 (12)	−0.0049 (10)	0.0092 (9)	0.0131 (10)
O6	0.0698 (11)	0.0645 (14)	0.1240 (17)	0.0081 (10)	0.0075 (11)	0.0283 (13)

Geometric parameters (Å, º) top

C1—C4	1.351 (4)	C8—H8	0.93
C1—C2	1.421 (6)	C9—C10	1.406 (5)
C1—H1	0.93	C9—H9	0.93
C2—C3	1.322 (6)	C10—C11	1.343 (4)
C2—H2	0.93	C10—H10	0.93
C3—O1	1.364 (4)	C11—O4	1.357 (3)
C3—H3	0.93	C11—C12	1.423 (3)
C4—O1	1.362 (4)	C12—N3	1.277 (3)
C4—C5	1.432 (4)	C12—H12	0.93
C5—N1	1.273 (3)	C13—O5	1.206 (3)
C5—H5	0.93	C13—O6	1.334 (3)
C6—O2	1.206 (4)	C13—N4	1.344 (3)
C6—O3	1.337 (3)	C14—O6	1.454 (4)
C6—N2	1.350 (3)	C14—H14A	0.96
C7—O3	1.450 (4)	C14—H14B	0.96
C7—H7A	0.96	C14—H14C	0.96
C7—H7B	0.96	N1—N2	1.370 (3)
C7—H7C	0.96	N2—H2A	0.86
C8—C9	1.309 (5)	N3—N4	1.373 (3)
C8—O4	1.368 (4)	N4—H4	0.86

C4—C1—C2	106.0 (3)	C11—C10—C9	107.4 (3)
C4—C1—H1	127.0	C11—C10—H10	126.3
C2—C1—H1	127.0	C9—C10—H10	126.3
C3—C2—C1	107.2 (3)	C10—C11—O4	108.7 (3)
C3—C2—H2	126.4	C10—C11—C12	133.1 (3)
C1—C2—H2	126.4	O4—C11—C12	118.1 (2)
C2—C3—O1	110.3 (4)	N3—C12—C11	122.1 (2)
C2—C3—H3	124.8	N3—C12—H12	119.0
O1—C3—H3	124.8	C11—C12—H12	119.0
C1—C4—O1	109.7 (3)	O5—C13—O6	125.1 (2)
C1—C4—C5	131.0 (3)	O5—C13—N4	125.6 (2)
O1—C4—C5	119.2 (2)	O6—C13—N4	109.4 (2)
N1—C5—C4	121.6 (2)	O6—C14—H14A	109.5
N1—C5—H5	119.2	O6—C14—H14B	109.5
C4—C5—H5	119.2	H14A—C14—H14B	109.5
O2—C6—O3	124.2 (3)	O6—C14—H14C	109.5
O2—C6—N2	125.9 (2)	H14A—C14—H14C	109.5
O3—C6—N2	109.9 (3)	H14B—C14—H14C	109.5
O3—C7—H7A	109.5	C5—N1—N2	115.3 (2)
O3—C7—H7B	109.5	C6—N2—N1	118.1 (2)
H7A—C7—H7B	109.5	C6—N2—H2A	120.9
O3—C7—H7C	109.5	N1—N2—H2A	120.9
H7A—C7—H7C	109.5	C12—N3—N4	115.6 (2)
H7B—C7—H7C	109.5	C13—N4—N3	118.9 (2)
C9—C8—O4	110.5 (3)	C13—N4—H4	120.5
C9—C8—H8	124.8	N3—N4—H4	120.5
O4—C8—H8	124.8	C4—O1—C3	106.7 (3)
C8—C9—C10	106.8 (3)	C6—O3—C7	114.9 (3)
C8—C9—H9	126.6	C11—O4—C8	106.6 (2)
C10—C9—H9	126.6	C13—O6—C14	116.3 (2)

C4—C1—C2—C3	1.7 (4)	C5—N1—N2—C6	−178.6 (2)
C1—C2—C3—O1	−1.6 (4)	C11—C12—N3—N4	178.7 (2)
C2—C1—C4—O1	−1.1 (3)	O5—C13—N4—N3	−3.8 (4)
C2—C1—C4—C5	177.6 (3)	O6—C13—N4—N3	176.4 (2)
C1—C4—C5—N1	178.0 (3)	C12—N3—N4—C13	−179.1 (2)
O1—C4—C5—N1	−3.3 (3)	C1—C4—O1—C3	0.2 (3)
O4—C8—C9—C10	0.8 (6)	C5—C4—O1—C3	−178.8 (2)
C8—C9—C10—C11	−0.6 (5)	C2—C3—O1—C4	0.9 (4)
C9—C10—C11—O4	0.1 (4)	O2—C6—O3—C7	−0.4 (4)
C9—C10—C11—C12	178.3 (3)	N2—C6—O3—C7	179.2 (3)
C10—C11—C12—N3	−171.0 (3)	C10—C11—O4—C8	0.3 (4)
O4—C11—C12—N3	7.0 (4)	C12—C11—O4—C8	−178.1 (3)
C4—C5—N1—N2	177.8 (2)	C9—C8—O4—C11	−0.7 (5)
O2—C6—N2—N1	−4.2 (4)	O5—C13—O6—C14	−0.8 (5)
O3—C6—N2—N1	176.2 (2)	N4—C13—O6—C14	179.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5	0.86	2.36	3.138 (3)	151
N2—H2A···N3	0.86	2.52	3.242 (3)	141
N4—H4···O2ⁱ	0.86	2.11	2.913 (3)	156
C2—H2···O5ⁱⁱ	0.93	2.60	3.521 (4)	172
C10—H10···O5ⁱⁱⁱ	0.93	2.59	3.508 (4)	171

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

Experimental details

Crystal data
Chemical formula	C₇H₈N₂O₃
M_r	168.15
Crystal system, space group	Monoclinic, C2
Temperature (K)	193
a, b, c (Å)	14.9185 (17), 7.8124 (9), 15.1299 (19)
β (°)	105.251 (7)
V (Å³)	1701.3 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.19 × 0.17 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.978, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	4679, 1601, 1399
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.085, 1.07
No. of reflections	1601
No. of parameters	218
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.09

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5	0.86	2.36	3.138 (3)	151
N2—H2A···N3	0.86	2.52	3.242 (3)	141
N4—H4···O2ⁱ	0.86	2.11	2.913 (3)	156
C2—H2···O5ⁱⁱ	0.93	2.60	3.521 (4)	172
C10—H10···O5ⁱⁱⁱ	0.93	2.59	3.508 (4)	171

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

Acknowledgements

The authors thank Hangzhou Vocational and Technical College, China, for financial support.

References

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