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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2914
https://doi.org/10.1107/S1600536810041528

N′-[6-(3,5-Di­methylpyrazol-1-yl)-1,2,4,5-tetrazin-3-yl]propanohydrazide

Qi-dong Yan,a Feng Xu,a* Jun Xua and Jian-jun Chena

aDepartment of Biological & Chemical Engineering, Taizhou Vocational & Technical College, Taizhou, 318000, People's Republic of China
*Correspondence e-mail: xufeng901@126.com

(Received 10 October 2010; accepted 14 October 2010; online 23 October 2010)

In the title compound, C10H14N8O, the tetra­zine and pyrazole rings form a dihedral angle of 48.81 (2)°. In the crystal, inter­molecular N—H⋯N and N—H⋯O hydrogen bonds link the mol­ecules into layers parallel to (101).

Related literature

For related structures, see: Hu et al. (2004[Hu, W. X., Rao, G. W. & Sun, Y. Q. (2004). Bioorg. Med. Chem. Lett. 14, 1177-1181.]); Xu et al. (2010[Xu, F., Yang, Z. Z., Hu, W. X. & Xi, L. M. (2010). Chin. J. Org. Chem. 30, 260-265.]). For applications of 1,2,4,5-tetra­zine derivatives, see: Sauer (1996[Sauer, J. (1996). Comprehensive Heterocyclic Chemistry, 2nd ed., edited by A. J. Boulton, Vol. 6, pp. 901-955. Oxford: Elsevier.]).

[Scheme 1]

Experimental

Crystal data

  • C10H14N8O

  • Mr = 262.29

  • Monoclinic, P 21 /n

  • a = 10.896 (3) Å

  • b = 8.0354 (18) Å

  • c = 14.805 (3) Å

  • β = 101.243 (3)°

  • V = 1271.3 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 103 K

  • 0.43 × 0.43 × 0.40 mm
Data collection

  • Rigaku AFC10/Saturn724+ diffractometer

  • 11006 measured reflections

  • 2889 independent reflections

  • 2449 reflections with I > 2σ(I)

  • Rint = 0.026
Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.097

  • S = 1.00

  • 2889 reflections

  • 183 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N14—H14N⋯O17i 0.859 (17) 1.980 (17) 2.821 (2) 166 (2)
N15—H15N⋯N8ii 0.893 (18) 1.996 (18) 2.882 (2) 171 (2)
Symmetry codes: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x+1, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2008[Rigaku/MSC (2008). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810041528/cv2774sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810041528/cv2774Isup2.hkl

checkCIF report


Comment top

1,2,4,5-Tetrazine derivatives have high potential for biological activity, possessing a wide spectrum of antiviral and antitumor properties. They have been widely used in pesticides and herbicides (Sauer,1996). In continuation of our study of the structure-activity relationships of 1,2,4,5-tetrazine derivatives (Hu et al., 2004; Xu et al., 2010), we present here the crystal structure of the title compound (I).

In (I) (Fig. 1), the essentially planar tetrazine ring forms a dihedral angle of 48.81 (2)° with the pyrazole ring. The N14/N15/C16/O17 and C16/C18/C19 planes form dihedral angles of 79.07 (2)° and 53.51 (2)°, respectively, with the tetrazine ring. In the crystal structure, intermolecular N—H···N and N—H···O hydrogen bonds (Table 1) link the molecules into layers parallel to the plane (101) (Fig. 2).

Related literature top

For related structures, see: Hu et al. (2004); Xu et al. (2010). For applications of 1,2,4,5-tetrazine derivatives, see: Sauer (1996).

Experimental top

3,6-Di(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine (3.0 mmol), chloroform (10 ml) and pyridine(0.25 ml,3.1 mmol) were mixed. Propionyl chloride(3.0 mmol) in chloroform (10 ml) was added dropwise with stirring at room temperature. After the starting 1,2,4,5-tetrazine was completely consumed (the reaction courses was monitored by TLC, ethyl acetate system), evaporation of the chloroform, crude product was obtained and purified by preparative thin-layer chromatography over silica gel GF254(2 mm) (dichloromethane: petroleum ether=1:1). The solution of the compound in anhydrous ethanol was concentrated gradually at room temperature to afford single crystals, which was suitable for X-ray diffraction.

Refinement top

C-bound H atoms were placed in calculated positions with C—H = 0.93 (aromatic) and 0.96 Å (methyl), and refined as riding, with Uiso(H) = 1.2Ueq(C). Amino H atoms were located on a difference map and isotropically refined.

Structure description top

1,2,4,5-Tetrazine derivatives have high potential for biological activity, possessing a wide spectrum of antiviral and antitumor properties. They have been widely used in pesticides and herbicides (Sauer,1996). In continuation of our study of the structure-activity relationships of 1,2,4,5-tetrazine derivatives (Hu et al., 2004; Xu et al., 2010), we present here the crystal structure of the title compound (I).

In (I) (Fig. 1), the essentially planar tetrazine ring forms a dihedral angle of 48.81 (2)° with the pyrazole ring. The N14/N15/C16/O17 and C16/C18/C19 planes form dihedral angles of 79.07 (2)° and 53.51 (2)°, respectively, with the tetrazine ring. In the crystal structure, intermolecular N—H···N and N—H···O hydrogen bonds (Table 1) link the molecules into layers parallel to the plane (101) (Fig. 2).

For related structures, see: Hu et al. (2004); Xu et al. (2010). For applications of 1,2,4,5-tetrazine derivatives, see: Sauer (1996).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2008); cell refinement: CrystalClear (Rigaku/MSC, 2008); data reduction: CrystalClear (Rigaku/MSC, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of (I), shown with 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. A portion of the crystal packing of (I), viewed down the b axis (N—H···O and N—H···N hydrogen bonds shown as dashed lines).
N'-[6-(3,5-Dimethylpyrazol-1-yl)-1,2,4,5-tetrazin-3-yl]propanohydrazide top
Crystal data top
C10H14N8OF(000) = 552
Mr = 262.29Dx = 1.370 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3481 reflections
a = 10.896 (3) Åθ = 3.1–27.5°
b = 8.0354 (18) ŵ = 0.10 mm−1
c = 14.805 (3) ÅT = 103 K
β = 101.243 (3)°Block, red
V = 1271.3 (5) Å30.43 × 0.43 × 0.40 mm
Z = 4
Data collection top
Rigaku AFC10/Saturn724+
diffractometer		2449 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.026
Graphite monochromatorθmax = 27.5°, θmin = 3.2°
Detector resolution: 28.5714 pixels mm-1h = −14→14
phi and ω scansk = −10→9
11006 measured reflectionsl = −19→15
2889 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0536P)2 + 0.356P]
where P = (Fo2 + 2Fc2)/3
2889 reflections(Δ/σ)max = 0.001
183 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C10H14N8OV = 1271.3 (5) Å3
Mr = 262.29Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.896 (3) ŵ = 0.10 mm−1
b = 8.0354 (18) ÅT = 103 K
c = 14.805 (3) Å0.43 × 0.43 × 0.40 mm
β = 101.243 (3)°
Data collection top
Rigaku AFC10/Saturn724+
diffractometer		2449 reflections with I > 2σ(I)
11006 measured reflectionsRint = 0.026
2889 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.25 e Å−3
2889 reflectionsΔρmin = −0.21 e Å−3
183 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
xyzUiso*/Ueq
O170.65146 (8)0.86367 (11)0.70314 (6)0.0179 (2)
N10.36485 (9)0.55187 (13)0.58619 (7)0.0181 (2)
N20.48288 (9)0.59455 (13)0.59073 (7)0.0178 (2)
N40.54093 (9)0.41800 (13)0.72319 (7)0.0178 (2)
N50.42231 (9)0.37460 (13)0.71646 (7)0.0180 (2)
N70.21537 (9)0.38630 (13)0.63454 (7)0.0153 (2)
N80.15710 (9)0.34258 (13)0.54720 (7)0.0162 (2)
N140.69045 (9)0.54690 (13)0.65843 (7)0.0150 (2)
N150.72507 (9)0.68179 (12)0.61051 (7)0.0143 (2)
C30.56793 (11)0.51973 (14)0.65674 (8)0.0141 (2)
C60.34064 (11)0.43941 (15)0.64680 (8)0.0144 (2)
C90.04184 (11)0.30101 (15)0.55470 (9)0.0160 (3)
C100.02513 (11)0.31991 (16)0.64640 (9)0.0182 (3)
H10−0.04910.29860.66910.022*
C110.13712 (11)0.37494 (15)0.69613 (8)0.0162 (3)
C120.17476 (12)0.42513 (18)0.79463 (9)0.0225 (3)
H12A0.10100.42540.82340.027*
H12B0.21140.53690.79830.027*
H12C0.23660.34610.82690.027*
C13−0.04989 (11)0.24561 (17)0.47157 (9)0.0202 (3)
H13A−0.01680.27050.41610.024*
H13B−0.12930.30450.46890.024*
H13C−0.06370.12550.47520.024*
C160.70060 (10)0.83713 (14)0.63648 (8)0.0138 (2)
C180.73811 (12)0.97462 (16)0.57793 (9)0.0204 (3)
H18A0.82781.00080.59990.024*
H18B0.72750.93540.51350.024*
C190.66242 (18)1.13003 (19)0.58044 (13)0.0396 (4)
H19A0.57441.10710.55390.048*
H19B0.69361.21750.54470.048*
H19C0.66981.16690.64440.048*
H14N0.7449 (16)0.507 (2)0.7030 (12)0.032 (5)*
H15N0.7596 (16)0.663 (2)0.5615 (12)0.032 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O170.0174 (4)0.0197 (5)0.0189 (4)−0.0030 (3)0.0092 (3)−0.0036 (4)
N10.0153 (5)0.0192 (5)0.0195 (5)−0.0025 (4)0.0025 (4)0.0026 (4)
N20.0153 (5)0.0183 (5)0.0196 (5)−0.0022 (4)0.0025 (4)0.0032 (4)
N40.0142 (5)0.0190 (5)0.0207 (5)−0.0005 (4)0.0045 (4)0.0042 (4)
N50.0161 (5)0.0184 (5)0.0203 (5)−0.0011 (4)0.0057 (4)0.0033 (4)
N70.0141 (5)0.0190 (5)0.0133 (5)−0.0019 (4)0.0040 (4)−0.0007 (4)
N80.0158 (5)0.0187 (5)0.0147 (5)−0.0018 (4)0.0042 (4)−0.0018 (4)
N140.0139 (5)0.0135 (5)0.0177 (5)−0.0003 (4)0.0034 (4)0.0048 (4)
N150.0170 (5)0.0132 (5)0.0146 (5)−0.0019 (4)0.0077 (4)0.0014 (4)
C30.0164 (5)0.0115 (5)0.0151 (6)−0.0001 (4)0.0051 (4)−0.0015 (4)
C60.0138 (5)0.0148 (6)0.0156 (6)−0.0012 (4)0.0050 (4)−0.0013 (4)
C90.0143 (5)0.0151 (6)0.0194 (6)−0.0003 (4)0.0054 (5)0.0012 (5)
C100.0162 (5)0.0200 (6)0.0202 (6)−0.0010 (5)0.0077 (5)0.0011 (5)
C110.0172 (6)0.0158 (6)0.0177 (6)0.0010 (4)0.0084 (5)0.0024 (5)
C120.0227 (6)0.0285 (7)0.0178 (6)−0.0022 (5)0.0075 (5)−0.0005 (5)
C130.0171 (6)0.0221 (6)0.0217 (6)−0.0034 (5)0.0042 (5)−0.0009 (5)
C160.0105 (5)0.0148 (6)0.0160 (6)−0.0013 (4)0.0026 (4)0.0000 (4)
C180.0224 (6)0.0167 (6)0.0241 (7)−0.0016 (5)0.0096 (5)0.0034 (5)
C190.0561 (10)0.0238 (8)0.0457 (10)0.0138 (7)0.0269 (8)0.0154 (7)
Geometric parameters (Å, º) top
O17—C161.2297 (15)C9—C131.4940 (17)
N1—N21.3200 (14)C10—C111.3698 (17)
N1—C61.3355 (16)C10—H100.9500
N2—C31.3499 (16)C11—C121.4914 (18)
N4—N51.3235 (14)C12—H12A0.9800
N4—C31.3547 (16)C12—H12B0.9800
N5—C61.3300 (16)C12—H12C0.9800
N7—C111.3675 (15)C13—H13A0.9800
N7—N81.3705 (14)C13—H13B0.9800
N7—C61.4076 (15)C13—H13C0.9800
N8—C91.3249 (15)C16—C181.5091 (17)
N14—C31.3480 (15)C18—C191.501 (2)
N14—N151.3874 (14)C18—H18A0.9900
N14—H14N0.860 (18)C18—H18B0.9900
N15—C161.3480 (16)C19—H19A0.9800
N15—H15N0.893 (19)C19—H19B0.9800
C9—C101.4128 (17)C19—H19C0.9800
N2—N1—C6117.36 (10)C10—C11—C12131.24 (11)
N1—N2—C3116.47 (10)C11—C12—H12A109.5
N5—N4—C3116.84 (10)C11—C12—H12B109.5
N4—N5—C6116.81 (10)H12A—C12—H12B109.5
C11—N7—N8112.19 (10)C11—C12—H12C109.5
C11—N7—C6130.48 (10)H12A—C12—H12C109.5
N8—N7—C6117.30 (9)H12B—C12—H12C109.5
C9—N8—N7104.95 (10)C9—C13—H13A109.5
C3—N14—N15118.95 (10)C9—C13—H13B109.5
C3—N14—H14N119.1 (12)H13A—C13—H13B109.5
N15—N14—H14N118.1 (12)C9—C13—H13C109.5
C16—N15—N14119.27 (10)H13A—C13—H13C109.5
C16—N15—H15N122.0 (11)H13B—C13—H13C109.5
N14—N15—H15N118.7 (11)O17—C16—N15122.06 (11)
N14—C3—N2118.61 (11)O17—C16—C18122.90 (11)
N14—C3—N4116.02 (10)N15—C16—C18115.04 (11)
N2—C3—N4125.37 (11)C19—C18—C16112.53 (11)
N5—C6—N1126.59 (11)C19—C18—H18A109.1
N5—C6—N7117.82 (11)C16—C18—H18A109.1
N1—C6—N7115.60 (10)C19—C18—H18B109.1
N8—C9—C10110.81 (11)C16—C18—H18B109.1
N8—C9—C13119.93 (11)H18A—C18—H18B107.8
C10—C9—C13129.25 (11)C18—C19—H19A109.5
C11—C10—C9106.44 (11)C18—C19—H19B109.5
C11—C10—H10126.8H19A—C19—H19B109.5
C9—C10—H10126.8C18—C19—H19C109.5
N7—C11—C10105.61 (11)H19A—C19—H19C109.5
N7—C11—C12123.07 (11)H19B—C19—H19C109.5
C6—N1—N2—C3−0.04 (16)C11—N7—C6—N1−130.25 (13)
C3—N4—N5—C6−2.11 (16)N8—N7—C6—N147.37 (15)
C11—N7—N8—C9−0.96 (13)N7—N8—C9—C100.78 (13)
C6—N7—N8—C9−179.01 (10)N7—N8—C9—C13−179.96 (10)
C3—N14—N15—C1664.25 (15)N8—C9—C10—C11−0.34 (14)
N15—N14—C3—N217.35 (16)C13—C9—C10—C11−179.53 (12)
N15—N14—C3—N4−162.40 (10)N8—N7—C11—C100.75 (13)
N1—N2—C3—N14173.64 (10)C6—N7—C11—C10178.47 (12)
N1—N2—C3—N4−6.63 (18)N8—N7—C11—C12−176.21 (11)
N5—N4—C3—N14−172.47 (10)C6—N7—C11—C121.5 (2)
N5—N4—C3—N27.79 (18)C9—C10—C11—N7−0.25 (13)
N4—N5—C6—N1−4.45 (19)C9—C10—C11—C12176.37 (13)
N4—N5—C6—N7175.75 (10)N14—N15—C16—O172.05 (17)
N2—N1—C6—N55.63 (19)N14—N15—C16—C18−178.04 (10)
N2—N1—C6—N7−174.57 (10)O17—C16—C18—C19−25.57 (18)
C11—N7—C6—N549.57 (18)N15—C16—C18—C19154.53 (13)
N8—N7—C6—N5−132.81 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N14—H14N···O17i0.859 (17)1.980 (17)2.821 (2)166 (2)
N15—H15N···N8ii0.893 (18)1.996 (18)2.882 (2)171 (2)
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC10H14N8O
Mr262.29
Crystal system, space groupMonoclinic, P21/n
Temperature (K)103
a, b, c (Å)10.896 (3), 8.0354 (18), 14.805 (3)
β (°) 101.243 (3)
V (Å3)1271.3 (5)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.43 × 0.43 × 0.40
Data collection
DiffractometerRigaku AFC10/Saturn724+
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		11006, 2889, 2449
Rint0.026
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.097, 1.00
No. of reflections2889
No. of parameters183
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.25, −0.21

Computer programs: CrystalClear (Rigaku/MSC, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N14—H14N···O17i0.859 (17)1.980 (17)2.821 (2)166 (2)
N15—H15N···N8ii0.893 (18)1.996 (18)2.882 (2)171 (2)
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1.
 

Acknowledgements

We are very grateful to the Science Foundation for Excellent Youth Scholars of the Department of Education of Zhejiang Province and the Educational Commission of Zhejiang Province of China (grant No. Y201018289).

References

First citationHu, W. X., Rao, G. W. & Sun, Y. Q. (2004). Bioorg. Med. Chem. Lett. 14, 1177–1181.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationRigaku/MSC (2008). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
 First citationSauer, J. (1996). Comprehensive Heterocyclic Chemistry, 2nd ed., edited by A. J. Boulton, Vol. 6, pp. 901–955. Oxford: Elsevier.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationXu, F., Yang, Z. Z., Hu, W. X. & Xi, L. M. (2010). Chin. J. Org. Chem. 30, 260–265.  CAS Google Scholar

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COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2914
https://doi.org/10.1107/S1600536810041528
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