Crystal structure of 4-amino-1-benzyl-1,2,4-triazolin-5-one.

The title compound, C9H10N4O, was obtained unintentionally by hydrolysis of 4-amino-1-benzyl-5-methyl-sulfanyl-1,2,4-triazolium tetra-fluoro-borate in the presence of sodium azide. In the crystal, alternating layers of polar amino-triazolinone and apolar benzene moieties are observed. N-H⋯O hydrogen bonds between the amino and carbonyl groups form infinite chains along [010]. These infinite chains are linked by additional C-H⋯O contacts.

Related literature

For the pharmacological activity of 1,2,4-triazoles, see: Sheng et al. (2011 ▶); Singla & Bhat (2010 ▶); Dayan et al. (2009 ▶); Li et al. (2003 ▶); Todoulou et al. (1994 ▶). For related structures, see: Thamotharan et al. (2003 ▶); Kaur et al. (2013 ▶); Sahin et al. (2014 ▶). For details of the synthesis, see: Becker et al. (1973a ▶,b ▶). For a description of the Cambridge Structural Database, see: Groom & Allen (2014 ▶).

Experimental

Crystal data

C9H10N4O

M = 190.21

Monoclinic,

a = 18.0861 (8) Å

b = 4.1690 (2) Å

c = 12.3694 (6) Å

β = 104.003 (5)°

V = 904.95 (7) Å3

Z = 4

Cu Kα radiation

μ = 0.80 mm−1

T = 173 K

0.2 × 0.2 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur (Ruby, Gemini ultra) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.867, T max = 1

7377 measured reflections

1613 independent reflections

1448 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.092

S = 1.03

1613 reflections

133 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2002 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681401931X/fj2680sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401931X/fj2680Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681401931X/fj2680Isup3.mol

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Supporting information file. DOI: 10.1107/S160053681401931X/fj2680Isup4.cml

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. DOI: 10.1107/S160053681401931X/fj2680fig1.tif

The mol­ecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.

Click here for additional data file.

. DOI: 10.1107/S160053681401931X/fj2680fig2.tif

Alternating layers of polar amino­triazolinone and apolar benzene moieties.

Click here for additional data file.

. DOI: 10.1107/S160053681401931X/fj2680fig3.tif

Arrangement of the triazole rings parallel to (13 4 ) and ( 4 3) planes.

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x y z x y z . DOI: 10.1107/S160053681401931X/fj2680fig4.tif

Hydrogen bonds between the amino and carbonyl groups form infinite chains. Symmetry operators (i): 1 − x, −1 − y, 2 − z; (ii): 1 − x, −y, 2 − z.

CCDC reference: 1021229

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H10N4O	F(000) = 400
Mr = 190.21	Dx = 1.396 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 4064 reflections
a = 18.0861 (8) Å	θ = 3.7–67.9°
b = 4.1690 (2) Å	µ = 0.80 mm−1
c = 12.3694 (6) Å	T = 173 K
β = 104.003 (5)°	Plate, colourless
V = 904.95 (7) Å3	0.2 × 0.2 × 0.08 mm
Z = 4

Oxford Diffraction Xcalibur (Ruby, Gemini ultra) diffractometer	1613 independent reflections
Graphite monochromator	1448 reflections with I > 2σ(I)
Detector resolution: 10.3575 pixels mm-1	Rint = 0.030
ω scans	θmax = 68.0°, θmin = 5.0°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −21→21
Tmin = 0.867, Tmax = 1	k = −4→4
7377 measured reflections	l = −14→14

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0489P)2 + 0.2066P] where P = (Fo2 + 2Fc2)/3
1613 reflections	(Δ/σ)max = 0.001
133 parameters	Δρmax = 0.17 e Å−3
2 restraints	Δρmin = −0.14 e Å−3

Experimental. Absorption correction: CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.41353 (5)	−0.0910 (2)	1.01696 (7)	0.0378 (3)
N3	0.47943 (7)	−0.4111 (3)	0.84565 (10)	0.0398 (3)
H31	0.5197 (9)	−0.283 (4)	0.8730 (13)	0.048*
H32	0.4789 (10)	−0.550 (4)	0.9007 (12)	0.048*
N1	0.32531 (6)	0.0899 (3)	0.85723 (8)	0.0315 (3)
N4	0.41310 (6)	−0.2253 (2)	0.83245 (8)	0.0301 (3)
N2	0.31212 (6)	0.0442 (3)	0.74333 (9)	0.0376 (3)
C1	0.38691 (7)	−0.0749 (3)	0.91540 (10)	0.0290 (3)
C5	0.14844 (8)	0.0222 (3)	0.81353 (11)	0.0368 (3)
H5	0.1579	0.0711	0.743	0.044*
C4	0.20132 (7)	0.1088 (3)	0.91021 (11)	0.0322 (3)
C6	0.08204 (8)	−0.1351 (4)	0.81894 (12)	0.0404 (3)
H6	0.0465	−0.1967	0.7523	0.049*
C7	0.06730 (8)	−0.2024 (4)	0.92066 (13)	0.0448 (4)
H7	0.0215	−0.3082	0.9243	0.054*
C9	0.18659 (8)	0.0385 (4)	1.01228 (12)	0.0417 (3)
H9	0.2225	0.0957	1.0791	0.05*
C2	0.36666 (7)	−0.1467 (3)	0.73250 (10)	0.0349 (3)
H2	0.3732	−0.2221	0.6629	0.042*
C3	0.27350 (7)	0.2839 (3)	0.90400 (12)	0.0384 (3)
H3A	0.2596	0.4788	0.8578	0.046*
H3B	0.3003	0.3534	0.9799	0.046*
C8	0.11940 (9)	−0.1154 (4)	1.01708 (13)	0.0492 (4)
H8	0.1093	−0.161	1.0874	0.059*

	U11	U22	U33	U12	U13	U23
O1	0.0376 (5)	0.0452 (6)	0.0301 (5)	−0.0017 (4)	0.0073 (4)	0.0004 (4)
N3	0.0338 (6)	0.0376 (7)	0.0490 (7)	0.0064 (5)	0.0116 (5)	0.0002 (5)
N1	0.0302 (5)	0.0293 (6)	0.0356 (6)	−0.0001 (4)	0.0094 (4)	0.0003 (4)
N4	0.0291 (5)	0.0287 (6)	0.0338 (5)	−0.0001 (4)	0.0102 (4)	−0.0002 (4)
N2	0.0363 (6)	0.0427 (7)	0.0332 (6)	0.0007 (5)	0.0070 (5)	0.0045 (5)
C1	0.0293 (6)	0.0255 (6)	0.0336 (6)	−0.0050 (5)	0.0101 (5)	0.0009 (5)
C5	0.0363 (7)	0.0378 (7)	0.0369 (7)	0.0016 (6)	0.0101 (5)	0.0006 (6)
C4	0.0308 (6)	0.0256 (7)	0.0406 (7)	0.0052 (5)	0.0093 (5)	−0.0033 (5)
C6	0.0330 (7)	0.0420 (8)	0.0446 (8)	−0.0002 (6)	0.0060 (6)	−0.0033 (6)
C7	0.0363 (7)	0.0423 (8)	0.0592 (9)	−0.0018 (6)	0.0181 (6)	0.0035 (7)
C9	0.0394 (7)	0.0463 (8)	0.0379 (7)	0.0050 (6)	0.0065 (6)	−0.0040 (6)
C2	0.0345 (7)	0.0402 (8)	0.0310 (6)	−0.0022 (6)	0.0097 (5)	−0.0003 (5)
C3	0.0345 (7)	0.0289 (7)	0.0533 (8)	0.0005 (5)	0.0136 (6)	−0.0073 (6)
C8	0.0507 (9)	0.0584 (10)	0.0428 (8)	0.0025 (7)	0.0197 (7)	0.0076 (7)

O1—C1	1.2335 (15)	C4—C9	1.383 (2)
N3—N4	1.4040 (15)	C4—C3	1.5138 (18)
N3—H31	0.900 (14)	C6—C7	1.377 (2)
N3—H32	0.895 (14)	C6—H6	0.95
N1—C1	1.3577 (17)	C7—C8	1.378 (2)
N1—N2	1.3840 (15)	C7—H7	0.95
N1—C3	1.4592 (16)	C9—C8	1.388 (2)
N4—C2	1.3561 (17)	C9—H9	0.95
N4—C1	1.3803 (16)	C2—H2	0.95
N2—C2	1.2993 (18)	C3—H3A	0.99
C5—C6	1.384 (2)	C3—H3B	0.99
C5—C4	1.3861 (19)	C8—H8	0.95
C5—H5	0.95
N4—N3—H31	107.9 (11)	C7—C6—H6	119.9
N4—N3—H32	106.2 (11)	C5—C6—H6	119.9
H31—N3—H32	104.7 (15)	C6—C7—C8	119.63 (13)
C1—N1—N2	112.77 (10)	C6—C7—H7	120.2
C1—N1—C3	126.43 (11)	C8—C7—H7	120.2
N2—N1—C3	120.72 (10)	C4—C9—C8	120.05 (13)
C2—N4—C1	108.65 (10)	C4—C9—H9	120
C2—N4—N3	124.24 (11)	C8—C9—H9	120
C1—N4—N3	126.97 (11)	N2—C2—N4	111.85 (11)
C2—N2—N1	103.95 (10)	N2—C2—H2	124.1
O1—C1—N1	129.42 (12)	N4—C2—H2	124.1
O1—C1—N4	127.80 (12)	N1—C3—C4	113.40 (11)
N1—C1—N4	102.77 (10)	N1—C3—H3A	108.9
C6—C5—C4	120.48 (12)	C4—C3—H3A	108.9
C6—C5—H5	119.8	N1—C3—H3B	108.9
C4—C5—H5	119.8	C4—C3—H3B	108.9
C9—C4—C5	119.16 (13)	H3A—C3—H3B	107.7
C9—C4—C3	120.48 (12)	C7—C8—C9	120.47 (13)
C5—C4—C3	120.35 (12)	C7—C8—H8	119.8
C7—C6—C5	120.20 (13)	C9—C8—H8	119.8
C1—N1—N2—C2	−0.71 (14)	C5—C6—C7—C8	−0.7 (2)
C3—N1—N2—C2	−177.58 (11)	C5—C4—C9—C8	−0.3 (2)
N2—N1—C1—O1	−178.86 (12)	C3—C4—C9—C8	178.48 (13)
C3—N1—C1—O1	−2.2 (2)	N1—N2—C2—N4	0.32 (14)
N2—N1—C1—N4	0.78 (13)	C1—N4—C2—N2	0.15 (15)
C3—N1—C1—N4	177.44 (11)	N3—N4—C2—N2	−175.76 (12)
C2—N4—C1—O1	179.10 (12)	C1—N1—C3—C4	−97.82 (15)
N3—N4—C1—O1	−5.1 (2)	N2—N1—C3—C4	78.60 (15)
C2—N4—C1—N1	−0.55 (13)	C9—C4—C3—N1	114.42 (14)
N3—N4—C1—N1	175.21 (11)	C5—C4—C3—N1	−66.81 (16)
C6—C5—C4—C9	−0.6 (2)	C6—C7—C8—C9	−0.2 (2)
C6—C5—C4—C3	−179.35 (12)	C4—C9—C8—C7	0.7 (2)
C4—C5—C6—C7	1.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H32···O1i	0.90 (1)	2.47 (2)	3.0583 (15)	124 (1)
N3—H31···O1ii	0.90 (1)	2.22 (2)	3.0701 (16)	156 (2)
C2—H2···O1iii	0.95	2.24	3.181 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H32⋯O1i	0.90 (1)	2.47 (2)	3.0583 (15)	124 (1)
N3—H31⋯O1ii	0.90 (1)	2.22 (2)	3.0701 (16)	156 (2)
C2—H2⋯O1iii	0.95	2.24	3.181 (2)	168

Symmetry codes: (i) ; (ii) ; (iii) .