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

In the title compound, C(10)H(14)N(8)O, the tetra-zine and pyrazole rings form a dihedral angle of 48.81 (2)°. In the crystal, inter-molecular N-H⋯N and N-H⋯O hydrogen bonds link the mol-ecules into layers parallel to (101).

Related literature

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

Crystal data

C10H14N8O

M = 262.29

Monoclinic,

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)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 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

Data collection: CrystalClear (Rigaku/MSC, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041528/cv2774Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H14N8O	F(000) = 552
Mr = 262.29	Dx = 1.370 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3481 reflections
a = 10.896 (3) Å	θ = 3.1–27.5°
b = 8.0354 (18) Å	µ = 0.10 mm−1
c = 14.805 (3) Å	T = 103 K
β = 101.243 (3)°	Block, red
V = 1271.3 (5) Å3	0.43 × 0.43 × 0.40 mm
Z = 4

Rigaku AFC10/Saturn724+ diffractometer	2449 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.026
graphite	θmax = 27.5°, θmin = 3.2°
Detector resolution: 28.5714 pixels mm-1	h = −14→14
phi and ω scans	k = −10→9
11006 measured reflections	l = −19→15
2889 independent reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H 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 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
O17	0.65146 (8)	0.86367 (11)	0.70314 (6)	0.0179 (2)
N1	0.36485 (9)	0.55187 (13)	0.58619 (7)	0.0181 (2)
N2	0.48288 (9)	0.59455 (13)	0.59073 (7)	0.0178 (2)
N4	0.54093 (9)	0.41800 (13)	0.72319 (7)	0.0178 (2)
N5	0.42231 (9)	0.37460 (13)	0.71646 (7)	0.0180 (2)
N7	0.21537 (9)	0.38630 (13)	0.63454 (7)	0.0153 (2)
N8	0.15710 (9)	0.34258 (13)	0.54720 (7)	0.0162 (2)
N14	0.69045 (9)	0.54690 (13)	0.65843 (7)	0.0150 (2)
N15	0.72507 (9)	0.68179 (12)	0.61051 (7)	0.0143 (2)
C3	0.56793 (11)	0.51973 (14)	0.65674 (8)	0.0141 (2)
C6	0.34064 (11)	0.43941 (15)	0.64680 (8)	0.0144 (2)
C9	0.04184 (11)	0.30101 (15)	0.55470 (9)	0.0160 (3)
C10	0.02513 (11)	0.31991 (16)	0.64640 (9)	0.0182 (3)
H10	−0.0491	0.2986	0.6691	0.022*
C11	0.13712 (11)	0.37494 (15)	0.69613 (8)	0.0162 (3)
C12	0.17476 (12)	0.42513 (18)	0.79463 (9)	0.0225 (3)
H12A	0.1010	0.4254	0.8234	0.027*
H12B	0.2114	0.5369	0.7983	0.027*
H12C	0.2366	0.3461	0.8269	0.027*
C13	−0.04989 (11)	0.24561 (17)	0.47157 (9)	0.0202 (3)
H13A	−0.0168	0.2705	0.4161	0.024*
H13B	−0.1293	0.3045	0.4689	0.024*
H13C	−0.0637	0.1255	0.4752	0.024*
C16	0.70060 (10)	0.83713 (14)	0.63648 (8)	0.0138 (2)
C18	0.73811 (12)	0.97462 (16)	0.57793 (9)	0.0204 (3)
H18A	0.8278	1.0008	0.5999	0.024*
H18B	0.7275	0.9354	0.5135	0.024*
C19	0.66242 (18)	1.13003 (19)	0.58044 (13)	0.0396 (4)
H19A	0.5744	1.1071	0.5539	0.048*
H19B	0.6936	1.2175	0.5447	0.048*
H19C	0.6698	1.1669	0.6444	0.048*
H14N	0.7449 (16)	0.507 (2)	0.7030 (12)	0.032 (5)*
H15N	0.7596 (16)	0.663 (2)	0.5615 (12)	0.032 (4)*

	U11	U22	U33	U12	U13	U23
O17	0.0174 (4)	0.0197 (5)	0.0189 (4)	−0.0030 (3)	0.0092 (3)	−0.0036 (4)
N1	0.0153 (5)	0.0192 (5)	0.0195 (5)	−0.0025 (4)	0.0025 (4)	0.0026 (4)
N2	0.0153 (5)	0.0183 (5)	0.0196 (5)	−0.0022 (4)	0.0025 (4)	0.0032 (4)
N4	0.0142 (5)	0.0190 (5)	0.0207 (5)	−0.0005 (4)	0.0045 (4)	0.0042 (4)
N5	0.0161 (5)	0.0184 (5)	0.0203 (5)	−0.0011 (4)	0.0057 (4)	0.0033 (4)
N7	0.0141 (5)	0.0190 (5)	0.0133 (5)	−0.0019 (4)	0.0040 (4)	−0.0007 (4)
N8	0.0158 (5)	0.0187 (5)	0.0147 (5)	−0.0018 (4)	0.0042 (4)	−0.0018 (4)
N14	0.0139 (5)	0.0135 (5)	0.0177 (5)	−0.0003 (4)	0.0034 (4)	0.0048 (4)
N15	0.0170 (5)	0.0132 (5)	0.0146 (5)	−0.0019 (4)	0.0077 (4)	0.0014 (4)
C3	0.0164 (5)	0.0115 (5)	0.0151 (6)	−0.0001 (4)	0.0051 (4)	−0.0015 (4)
C6	0.0138 (5)	0.0148 (6)	0.0156 (6)	−0.0012 (4)	0.0050 (4)	−0.0013 (4)
C9	0.0143 (5)	0.0151 (6)	0.0194 (6)	−0.0003 (4)	0.0054 (5)	0.0012 (5)
C10	0.0162 (5)	0.0200 (6)	0.0202 (6)	−0.0010 (5)	0.0077 (5)	0.0011 (5)
C11	0.0172 (6)	0.0158 (6)	0.0177 (6)	0.0010 (4)	0.0084 (5)	0.0024 (5)
C12	0.0227 (6)	0.0285 (7)	0.0178 (6)	−0.0022 (5)	0.0075 (5)	−0.0005 (5)
C13	0.0171 (6)	0.0221 (6)	0.0217 (6)	−0.0034 (5)	0.0042 (5)	−0.0009 (5)
C16	0.0105 (5)	0.0148 (6)	0.0160 (6)	−0.0013 (4)	0.0026 (4)	0.0000 (4)
C18	0.0224 (6)	0.0167 (6)	0.0241 (7)	−0.0016 (5)	0.0096 (5)	0.0034 (5)
C19	0.0561 (10)	0.0238 (8)	0.0457 (10)	0.0138 (7)	0.0269 (8)	0.0154 (7)

O17—C16	1.2297 (15)	C9—C13	1.4940 (17)
N1—N2	1.3200 (14)	C10—C11	1.3698 (17)
N1—C6	1.3355 (16)	C10—H10	0.9500
N2—C3	1.3499 (16)	C11—C12	1.4914 (18)
N4—N5	1.3235 (14)	C12—H12A	0.9800
N4—C3	1.3547 (16)	C12—H12B	0.9800
N5—C6	1.3300 (16)	C12—H12C	0.9800
N7—C11	1.3675 (15)	C13—H13A	0.9800
N7—N8	1.3705 (14)	C13—H13B	0.9800
N7—C6	1.4076 (15)	C13—H13C	0.9800
N8—C9	1.3249 (15)	C16—C18	1.5091 (17)
N14—C3	1.3480 (15)	C18—C19	1.501 (2)
N14—N15	1.3874 (14)	C18—H18A	0.9900
N14—H14N	0.860 (18)	C18—H18B	0.9900
N15—C16	1.3480 (16)	C19—H19A	0.9800
N15—H15N	0.893 (19)	C19—H19B	0.9800
C9—C10	1.4128 (17)	C19—H19C	0.9800
N2—N1—C6	117.36 (10)	C10—C11—C12	131.24 (11)
N1—N2—C3	116.47 (10)	C11—C12—H12A	109.5
N5—N4—C3	116.84 (10)	C11—C12—H12B	109.5
N4—N5—C6	116.81 (10)	H12A—C12—H12B	109.5
C11—N7—N8	112.19 (10)	C11—C12—H12C	109.5
C11—N7—C6	130.48 (10)	H12A—C12—H12C	109.5
N8—N7—C6	117.30 (9)	H12B—C12—H12C	109.5
C9—N8—N7	104.95 (10)	C9—C13—H13A	109.5
C3—N14—N15	118.95 (10)	C9—C13—H13B	109.5
C3—N14—H14N	119.1 (12)	H13A—C13—H13B	109.5
N15—N14—H14N	118.1 (12)	C9—C13—H13C	109.5
C16—N15—N14	119.27 (10)	H13A—C13—H13C	109.5
C16—N15—H15N	122.0 (11)	H13B—C13—H13C	109.5
N14—N15—H15N	118.7 (11)	O17—C16—N15	122.06 (11)
N14—C3—N2	118.61 (11)	O17—C16—C18	122.90 (11)
N14—C3—N4	116.02 (10)	N15—C16—C18	115.04 (11)
N2—C3—N4	125.37 (11)	C19—C18—C16	112.53 (11)
N5—C6—N1	126.59 (11)	C19—C18—H18A	109.1
N5—C6—N7	117.82 (11)	C16—C18—H18A	109.1
N1—C6—N7	115.60 (10)	C19—C18—H18B	109.1
N8—C9—C10	110.81 (11)	C16—C18—H18B	109.1
N8—C9—C13	119.93 (11)	H18A—C18—H18B	107.8
C10—C9—C13	129.25 (11)	C18—C19—H19A	109.5
C11—C10—C9	106.44 (11)	C18—C19—H19B	109.5
C11—C10—H10	126.8	H19A—C19—H19B	109.5
C9—C10—H10	126.8	C18—C19—H19C	109.5
N7—C11—C10	105.61 (11)	H19A—C19—H19C	109.5
N7—C11—C12	123.07 (11)	H19B—C19—H19C	109.5
C6—N1—N2—C3	−0.04 (16)	C11—N7—C6—N1	−130.25 (13)
C3—N4—N5—C6	−2.11 (16)	N8—N7—C6—N1	47.37 (15)
C11—N7—N8—C9	−0.96 (13)	N7—N8—C9—C10	0.78 (13)
C6—N7—N8—C9	−179.01 (10)	N7—N8—C9—C13	−179.96 (10)
C3—N14—N15—C16	64.25 (15)	N8—C9—C10—C11	−0.34 (14)
N15—N14—C3—N2	17.35 (16)	C13—C9—C10—C11	−179.53 (12)
N15—N14—C3—N4	−162.40 (10)	N8—N7—C11—C10	0.75 (13)
N1—N2—C3—N14	173.64 (10)	C6—N7—C11—C10	178.47 (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—C12	1.5 (2)
N5—N4—C3—N2	7.79 (18)	C9—C10—C11—N7	−0.25 (13)
N4—N5—C6—N1	−4.45 (19)	C9—C10—C11—C12	176.37 (13)
N4—N5—C6—N7	175.75 (10)	N14—N15—C16—O17	2.05 (17)
N2—N1—C6—N5	5.63 (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—N5	49.57 (18)	N15—C16—C18—C19	154.53 (13)
N8—N7—C6—N5	−132.81 (12)

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)

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) ; (ii) .