N-[(Z)-(1-Methyl-1H-pyrrol-2-yl)methyl-idene]-1H-1,2,4-triazol-5-amine.

In the title compound, C(8)H(9)N(5), a Schiff base derived from N-methyl-pyrrole-2-carbaldehyde and 3-amino-1,2,4-triazole, the C=N double bond linking the two aromatic rings has a Z conformation. The two rings are twisted by 24.20 (5)°. A chain motif results from N-H⋯N hydrogen bonding.

Related literature

For a related structure, see: Arfan et al. (2008 ▶).

Experimental

Crystal data

C8H9N5

M = 175.20

Monoclinic,

a = 7.2519 (3) Å

b = 12.8616 (6) Å

c = 9.7445 (4) Å

β = 101.917 (2)°

V = 889.29 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 (2) K

0.26 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.976, T max = 0.988

10203 measured reflections

2212 independent reflections

1651 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.107

S = 1.03

2212 reflections

136 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680804097X/ng2523sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680804097X/ng2523Isup2.hkl

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

C8H9N5	F(000) = 368
Mr = 175.20	Dx = 1.309 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1859 reflections
a = 7.2519 (3) Å	θ = 2.7–28.3°
b = 12.8616 (6) Å	µ = 0.09 mm−1
c = 9.7445 (4) Å	T = 296 K
β = 101.917 (2)°	Prismatic, orange
V = 889.29 (7) Å3	0.26 × 0.20 × 0.16 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2212 independent reflections
Radiation source: fine-focus sealed tube	1651 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 7.4 pixels mm-1	θmax = 28.3°, θmin = 2.7°
ω scans	h = −5→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −16→17
Tmin = 0.976, Tmax = 0.988	l = −12→12
10203 measured 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0556P)2 + 0.079P] where P = (Fo2 + 2Fc2)/3
2212 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
N1	0.11672 (13)	0.58683 (8)	0.33358 (11)	0.0543 (3)
N2	0.27287 (13)	0.37308 (7)	0.38528 (9)	0.0459 (3)
N3	0.38353 (14)	0.21080 (7)	0.32861 (9)	0.0475 (3)
N4	0.44733 (16)	0.11865 (8)	0.38789 (10)	0.0552 (3)
N5	0.37569 (15)	0.22874 (7)	0.54902 (9)	0.0494 (3)
C1	0.0572 (2)	0.53330 (12)	0.20067 (14)	0.0754 (5)
C2	0.0834 (2)	0.68853 (11)	0.35562 (19)	0.0691 (5)
C3	0.1530 (2)	0.71296 (12)	0.49152 (19)	0.0719 (6)
C4	0.23118 (19)	0.62366 (11)	0.55771 (16)	0.0609 (5)
C5	0.20967 (15)	0.54493 (9)	0.45902 (12)	0.0471 (3)
C6	0.27772 (15)	0.44120 (9)	0.48170 (12)	0.0451 (3)
C7	0.34307 (15)	0.27546 (8)	0.42465 (10)	0.0415 (3)
C8	0.43865 (19)	0.13408 (10)	0.51969 (12)	0.0545 (4)
H1A	−0.03220	0.57556	0.13837	0.1132*
H1B	−0.00032	0.46826	0.21599	0.1132*
H1C	0.16470	0.52068	0.15976	0.1132*
H2	0.025 (2)	0.7315 (13)	0.2805 (17)	0.0829*
H3	0.149 (2)	0.7801 (13)	0.5321 (17)	0.0862*
H3N	0.3769 (18)	0.2235 (10)	0.2359 (14)	0.0571*
H4	0.294 (2)	0.6150 (11)	0.6550 (17)	0.0730*
H6	0.3326 (17)	0.4259 (9)	0.5798 (14)	0.0541*
H8	0.4755 (19)	0.0815 (11)	0.5904 (15)	0.0655*

	U11	U22	U33	U12	U13	U23
N1	0.0532 (5)	0.0502 (6)	0.0587 (6)	0.0034 (4)	0.0099 (4)	0.0071 (5)
N2	0.0558 (5)	0.0467 (5)	0.0355 (5)	0.0026 (4)	0.0102 (4)	0.0039 (4)
N3	0.0696 (6)	0.0446 (5)	0.0290 (4)	−0.0016 (4)	0.0116 (4)	−0.0003 (4)
N4	0.0813 (7)	0.0435 (6)	0.0415 (5)	0.0025 (5)	0.0143 (5)	−0.0004 (4)
N5	0.0708 (6)	0.0486 (5)	0.0302 (4)	0.0041 (4)	0.0137 (4)	0.0046 (4)
C1	0.0920 (10)	0.0713 (10)	0.0546 (8)	0.0084 (8)	−0.0044 (7)	0.0100 (7)
C2	0.0635 (8)	0.0525 (8)	0.0924 (11)	0.0090 (6)	0.0187 (7)	0.0113 (7)
C3	0.0720 (9)	0.0503 (8)	0.0983 (12)	0.0023 (7)	0.0292 (8)	−0.0106 (8)
C4	0.0618 (8)	0.0581 (8)	0.0653 (8)	−0.0038 (6)	0.0189 (6)	−0.0101 (6)
C5	0.0455 (5)	0.0481 (6)	0.0494 (6)	−0.0023 (5)	0.0135 (4)	0.0009 (5)
C6	0.0499 (6)	0.0485 (6)	0.0373 (5)	−0.0020 (5)	0.0102 (4)	0.0035 (5)
C7	0.0515 (6)	0.0444 (6)	0.0288 (5)	−0.0021 (4)	0.0090 (4)	0.0009 (4)
C8	0.0782 (8)	0.0466 (7)	0.0388 (6)	0.0043 (6)	0.0120 (5)	0.0068 (5)

N1—C1	1.4515 (17)	C3—C4	1.380 (2)
N1—C2	1.3553 (18)	C4—C5	1.3830 (19)
N1—C5	1.3779 (15)	C5—C6	1.4238 (16)
N2—C6	1.2798 (14)	C1—H1A	0.9600
N2—C7	1.3792 (14)	C1—H1B	0.9600
N3—N4	1.3572 (14)	C1—H1C	0.9600
N3—C7	1.3293 (14)	C2—H2	0.945 (16)
N4—C8	1.3139 (15)	C3—H3	0.953 (17)
N5—C7	1.3294 (13)	C4—H4	0.970 (16)
N5—C8	1.3514 (16)	C6—H6	0.977 (13)
N3—H3N	0.910 (13)	C8—H8	0.963 (14)
C2—C3	1.353 (3)
N1···N2	2.9763 (14)	C1···H3vii	3.058 (16)
N2···N1	2.9763 (14)	C6···H1B	2.9600
N2···C1	2.9609 (17)	C7···H2iv	3.039 (16)
N3···N5i	2.8225 (12)	C7···H3Niii	2.992 (13)
N3···N5	2.1725 (12)	C8···H8ii	3.083 (14)
N4···C8ii	3.4283 (17)	C8···H3Niii	2.896 (13)
N4···N5	2.2532 (14)	H1A···H2	2.4200
N5···N3iii	2.8225 (12)	H1B···N2	2.6100
N5···N4	2.2532 (14)	H1B···C6	2.9600
N2···H1B	2.6100	H1C···N2	2.8900
N2···H1C	2.8900	H2···H1A	2.4200
N3···H2iv	2.946 (15)	H2···N3viii	2.946 (15)
N4···H8ii	2.634 (14)	H2···C7viii	3.039 (16)
N5···H6	2.580 (12)	H3···C1ix	3.058 (16)
N5···H3Niii	1.920 (13)	H3N···N5i	1.920 (13)
C1···N2	2.9609 (17)	H3N···C7i	2.992 (13)
C3···C7v	3.5793 (19)	H3N···C8i	2.896 (13)
C3···C8v	3.576 (2)	H3N···H6i	2.431 (18)
C4···C7v	3.3206 (18)	H4···H6	2.572 (19)
C5···C5vi	3.4963 (16)	H6···N5	2.580 (12)
C6···C6v	3.5119 (16)	H6···H4	2.572 (19)
C7···C3v	3.5793 (19)	H6···H3Niii	2.431 (18)
C7···C4v	3.3206 (18)	H8···N4ii	2.634 (14)
C8···C3v	3.576 (2)	H8···C8ii	3.083 (14)
C8···N4ii	3.4283 (17)
C1—N1—C2	124.70 (12)	N3—C7—N5	109.60 (9)
C1—N1—C5	127.37 (11)	N4—C8—N5	115.42 (11)
C2—N1—C5	107.91 (11)	N1—C1—H1A	109.00
C6—N2—C7	117.80 (9)	N1—C1—H1B	109.00
N4—N3—C7	110.62 (8)	N1—C1—H1C	109.00
N3—N4—C8	101.73 (10)	H1A—C1—H1B	109.00
C7—N5—C8	102.63 (9)	H1A—C1—H1C	109.00
N4—N3—H3N	121.5 (8)	H1B—C1—H1C	109.00
C7—N3—H3N	127.8 (8)	N1—C2—H2	120.5 (10)
N1—C2—C3	109.66 (14)	C3—C2—H2	129.7 (10)
C2—C3—C4	107.35 (14)	C2—C3—H3	125.4 (10)
C3—C4—C5	107.93 (13)	C4—C3—H3	127.2 (10)
N1—C5—C4	107.15 (11)	C3—C4—H4	128.1 (9)
C4—C5—C6	126.33 (11)	C5—C4—H4	124.0 (9)
N1—C5—C6	126.48 (10)	N2—C6—H6	121.6 (7)
N2—C6—C5	124.85 (11)	C5—C6—H6	113.5 (7)
N2—C7—N3	119.75 (9)	N4—C8—H8	122.1 (9)
N2—C7—N5	130.62 (9)	N5—C8—H8	122.5 (9)
C1—N1—C5—C4	−177.86 (12)	C7—N3—N4—C8	0.72 (13)
C1—N1—C2—C3	178.37 (12)	N3—N4—C8—N5	−0.41 (15)
C5—N1—C2—C3	0.21 (16)	C8—N5—C7—N3	0.52 (13)
C2—N1—C5—C6	−177.44 (12)	C8—N5—C7—N2	178.36 (12)
C2—N1—C5—C4	0.23 (14)	C7—N5—C8—N4	−0.06 (15)
C1—N1—C5—C6	4.47 (19)	N1—C2—C3—C4	−0.57 (17)
C6—N2—C7—N5	18.65 (18)	C2—C3—C4—C5	0.70 (17)
C6—N2—C7—N3	−163.70 (11)	C3—C4—C5—C6	177.10 (12)
C7—N2—C6—C5	−179.40 (11)	C3—C4—C5—N1	−0.57 (15)
N4—N3—C7—N5	−0.82 (14)	C4—C5—C6—N2	−172.36 (12)
N4—N3—C7—N2	−178.93 (10)	N1—C5—C6—N2	4.88 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3n···N5i	0.910 (13)	1.920 (13)	2.8225 (12)	171.3 (12)
C1—H1B···N2	0.9600	2.6100	2.9609 (17)	102.00

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3n⋯N5i	0.91 (1)	1.92 (1)	2.8225 (12)	171 (1)

Symmetry code: (i) .