2-(4-Amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-ylmeth-yl)isoindoline-1,3-dione.

The title compound, C(11)H(9)N(5)O(2)S, was synthesized from N-phthaloylglycine and thio-carbohydrazide by the fusion method. This is the first report of a triazole derivative of N-phthaloylglycine. The title compound exists in the thione form. The mol-ecule is non-planar, with a dihedral angle between the isoindoline ring system and the triazole ring system of 82.24 (5)°. The crystal structure is stabilized by inter-molecular hydrogen bonding linking the mol-ecules into a three-dimensional network.

Related literature

For related literature, see: Allen et al. (1987 ▶); Antunes et al. (1998 ▶); Barooah et al. (2006a ▶,b ▶); Brana & Ramos (2001 ▶); Chandrasekhar et al. (1999 ▶); Eugenio, et al. (2004 ▶); Görner et al. (2002 ▶); Khan & Ismail (2002 ▶); Matijević-Sosa & Cvetnić (2005 ▶); Neto et al. (1993 ▶); Ng (1992 ▶); Shariat & Abdollahi (2004 ▶); Wang et al. (1998 ▶); Xu et al. (2005 ▶), Zhang et al. (2004 ▶).

Experimental

Crystal data

C11H9N5O2S

M = 275.29

Orthorhombic,

a = 5.1961 (11) Å

b = 19.952 (4) Å

c = 11.336 (3) Å

V = 1175.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 100 (2) K

0.60 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2001 ▶) T min = 0.849, T max = 0.946

6288 measured reflections

2361 independent reflections

2281 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.069

S = 1.04

2361 reflections

184 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), with 1091 Friedel pairs

Flack parameter: −0.04 (6)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SMART; 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 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808001189/rn2038sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001189/rn2038Isup2.hkl

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

C11H9N5O2S	F000 = 568
Mr = 275.29	Dx = 1.556 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P2c-2n	Cell parameters from 934 reflections
a = 5.1961 (11) Å	θ = 3.6–26.4º
b = 19.952 (4) Å	µ = 0.28 mm−1
c = 11.336 (3) Å	T = 100 (2) K
V = 1175.2 (4) Å3	Plate, colourless
Z = 4	0.60 × 0.20 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	2361 independent reflections
Radiation source: fine-focus sealed tube	2281 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
T = 100(2) K	θmax = 26.4º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker 2001)	h = −6→6
Tmin = 0.849, Tmax = 0.946	k = −24→17
6288 measured reflections	l = −14→13

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.028	w = 1/[σ2(Fo2) + (0.0413P)2 + 0.1704P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.069	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.30 e Å−3
2361 reflections	Δρmin = −0.16 e Å−3
184 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 1091 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.04 (6)
Secondary atom site location: difference Fourier map

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
S1	−0.14861 (8)	0.68164 (2)	0.30015 (4)	0.01625 (11)
O1	0.1683 (2)	0.52047 (6)	0.66973 (11)	0.0180 (3)
O2	0.8375 (3)	0.66831 (7)	0.68855 (12)	0.0214 (3)
N1	0.5265 (3)	0.58747 (7)	0.65527 (13)	0.0147 (3)
N2	0.2503 (3)	0.63673 (7)	0.43781 (13)	0.0130 (3)
N3	0.1312 (3)	0.56622 (7)	0.30883 (15)	0.0158 (3)
H3N	0.051 (5)	0.5428 (11)	0.259 (2)	0.025 (6)*
N4	0.3250 (3)	0.53474 (8)	0.37168 (15)	0.0166 (3)
N5	0.2864 (3)	0.69419 (8)	0.50736 (16)	0.0154 (3)
H5M	0.141 (4)	0.6996 (11)	0.553 (2)	0.018 (6)*
H5N	0.297 (4)	0.7244 (11)	0.4569 (19)	0.012 (5)*
C1	0.3120 (3)	0.56238 (9)	0.71243 (16)	0.0150 (4)
C2	0.3011 (4)	0.59671 (9)	0.82861 (14)	0.0152 (4)
C3	0.1294 (4)	0.59041 (10)	0.92077 (16)	0.0182 (4)
H3	−0.0128	0.5606	0.9163	0.022*
C4	0.1732 (4)	0.62951 (10)	1.02058 (17)	0.0214 (4)
H4	0.0574	0.6265	1.0852	0.026*
C5	0.3824 (4)	0.67281 (10)	1.02788 (19)	0.0230 (5)
H5	0.4097	0.6980	1.0979	0.028*
C6	0.5528 (4)	0.67960 (9)	0.93312 (18)	0.0211 (4)
H6	0.6953	0.7093	0.9370	0.025*
C7	0.5063 (4)	0.64151 (9)	0.83394 (16)	0.0165 (4)
C8	0.6511 (3)	0.63748 (9)	0.72124 (18)	0.0176 (4)
C9	0.6033 (3)	0.56940 (10)	0.53675 (16)	0.0154 (4)
H9A	0.6560	0.5217	0.5358	0.018*
H9B	0.7544	0.5967	0.5138	0.018*
C10	0.3944 (3)	0.57960 (9)	0.44821 (17)	0.0147 (4)
C11	0.0778 (4)	0.62815 (9)	0.34723 (15)	0.0138 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0147 (2)	0.0187 (2)	0.0154 (2)	0.00169 (17)	−0.0019 (2)	−0.0004 (2)
O1	0.0184 (7)	0.0189 (6)	0.0168 (7)	−0.0046 (5)	0.0012 (5)	0.0002 (5)
O2	0.0170 (7)	0.0237 (7)	0.0234 (8)	−0.0047 (6)	−0.0012 (6)	0.0008 (6)
N1	0.0137 (8)	0.0169 (7)	0.0135 (8)	−0.0017 (6)	−0.0014 (6)	0.0016 (6)
N2	0.0128 (7)	0.0125 (7)	0.0136 (7)	−0.0016 (6)	0.0011 (6)	−0.0007 (6)
N3	0.0188 (7)	0.0143 (7)	0.0142 (8)	−0.0003 (6)	−0.0030 (7)	−0.0020 (7)
N4	0.0180 (8)	0.0166 (7)	0.0153 (8)	−0.0001 (6)	−0.0003 (6)	0.0009 (6)
N5	0.0194 (8)	0.0115 (7)	0.0153 (8)	−0.0002 (6)	0.0011 (7)	−0.0010 (6)
C1	0.0143 (9)	0.0160 (9)	0.0147 (9)	0.0023 (7)	−0.0003 (7)	0.0046 (7)
C2	0.0174 (9)	0.0145 (8)	0.0137 (9)	0.0034 (7)	−0.0024 (7)	0.0011 (7)
C3	0.0185 (9)	0.0198 (10)	0.0162 (10)	0.0043 (8)	0.0013 (7)	0.0038 (8)
C4	0.0258 (10)	0.0256 (11)	0.0130 (10)	0.0101 (8)	0.0028 (8)	0.0034 (8)
C5	0.0283 (12)	0.0221 (11)	0.0187 (11)	0.0083 (8)	−0.0055 (8)	−0.0035 (8)
C6	0.0217 (10)	0.0178 (10)	0.0238 (11)	0.0035 (8)	−0.0058 (9)	−0.0047 (8)
C7	0.0146 (9)	0.0158 (9)	0.0192 (9)	0.0025 (7)	−0.0044 (7)	0.0024 (7)
C8	0.0156 (9)	0.0163 (9)	0.0209 (10)	0.0009 (7)	−0.0049 (8)	0.0007 (7)
C9	0.0137 (9)	0.0179 (10)	0.0147 (9)	0.0006 (7)	0.0030 (7)	0.0015 (7)
C10	0.0158 (9)	0.0136 (9)	0.0148 (9)	−0.0017 (7)	0.0042 (7)	0.0015 (7)
C11	0.0141 (8)	0.0149 (9)	0.0123 (8)	−0.0039 (7)	0.0026 (7)	0.0009 (7)

S1—C11	1.6758 (19)	C1—C2	1.486 (2)
O1—C1	1.221 (2)	C2—C3	1.379 (3)
O2—C8	1.206 (2)	C2—C7	1.393 (3)
N1—C1	1.383 (2)	C3—C4	1.393 (3)
N1—C8	1.405 (2)	C3—H3	0.9500
N1—C9	1.447 (2)	C4—C5	1.391 (3)
N2—C10	1.369 (2)	C4—H4	0.9500
N2—C11	1.374 (2)	C5—C6	1.399 (3)
N2—N5	1.404 (2)	C5—H5	0.9500
N3—C11	1.339 (2)	C6—C7	1.378 (3)
N3—N4	1.384 (2)	C6—H6	0.9500
N3—H3N	0.84 (2)	C7—C8	1.485 (3)
N4—C10	1.297 (2)	C9—C10	1.492 (3)
N5—H5M	0.92 (2)	C9—H9A	0.9900
N5—H5N	0.83 (2)	C9—H9B	0.9900
C1—N1—C8	112.26 (15)	C4—C5—C6	120.62 (18)
C1—N1—C9	124.53 (16)	C4—C5—H5	119.7
C8—N1—C9	122.97 (16)	C6—C5—H5	119.7
C10—N2—C11	108.51 (15)	C7—C6—C5	117.51 (19)
C10—N2—N5	123.96 (16)	C7—C6—H6	121.2
C11—N2—N5	127.49 (15)	C5—C6—H6	121.2
C11—N3—N4	113.71 (16)	C6—C7—C2	121.57 (18)
C11—N3—H3N	128.9 (17)	C6—C7—C8	130.00 (18)
N4—N3—H3N	116.8 (16)	C2—C7—C8	108.41 (15)
C10—N4—N3	103.49 (15)	O2—C8—N1	124.66 (19)
N2—N5—H5M	107.6 (14)	O2—C8—C7	130.08 (18)
N2—N5—H5N	102.3 (14)	N1—C8—C7	105.26 (15)
H5M—N5—H5N	111 (2)	N1—C9—C10	112.97 (14)
O1—C1—N1	123.71 (17)	N1—C9—H9A	109.0
O1—C1—C2	130.07 (17)	C10—C9—H9A	109.0
N1—C1—C2	106.21 (15)	N1—C9—H9B	109.0
C3—C2—C7	121.38 (17)	C10—C9—H9B	109.0
C3—C2—C1	130.85 (18)	H9A—C9—H9B	107.8
C7—C2—C1	107.77 (15)	N4—C10—N2	111.40 (16)
C2—C3—C4	117.30 (18)	N4—C10—C9	123.90 (16)
C2—C3—H3	121.4	N2—C10—C9	124.69 (16)
C4—C3—H3	121.4	N3—C11—N2	102.87 (15)
C5—C4—C3	121.58 (18)	N3—C11—S1	129.02 (15)
C5—C4—H4	119.2	N2—C11—S1	128.09 (14)
C3—C4—H4	119.2
C11—N3—N4—C10	−1.5 (2)	C1—N1—C8—C7	3.1 (2)
C8—N1—C1—O1	176.97 (17)	C9—N1—C8—C7	177.81 (15)
C9—N1—C1—O1	2.3 (3)	C6—C7—C8—O2	−3.0 (3)
C8—N1—C1—C2	−2.7 (2)	C2—C7—C8—O2	178.56 (19)
C9—N1—C1—C2	−177.36 (16)	C6—C7—C8—N1	176.21 (18)
O1—C1—C2—C3	1.0 (3)	C2—C7—C8—N1	−2.19 (19)
N1—C1—C2—C3	−179.35 (18)	C1—N1—C9—C10	54.3 (2)
O1—C1—C2—C7	−178.46 (18)	C8—N1—C9—C10	−119.80 (18)
N1—C1—C2—C7	1.21 (19)	N3—N4—C10—N2	1.3 (2)
C7—C2—C3—C4	−1.5 (3)	N3—N4—C10—C9	−179.32 (16)
C1—C2—C3—C4	179.12 (19)	C11—N2—C10—N4	−0.7 (2)
C2—C3—C4—C5	−0.5 (3)	N5—N2—C10—N4	−178.54 (16)
C3—C4—C5—C6	1.6 (3)	C11—N2—C10—C9	179.92 (16)
C4—C5—C6—C7	−0.6 (3)	N5—N2—C10—C9	2.0 (3)
C5—C6—C7—C2	−1.4 (3)	N1—C9—C10—N4	−130.71 (18)
C5—C6—C7—C8	−179.66 (18)	N1—C9—C10—N2	48.6 (2)
C3—C2—C7—C6	2.6 (3)	N4—N3—C11—N2	1.11 (19)
C1—C2—C7—C6	−177.94 (17)	N4—N3—C11—S1	−177.21 (14)
C3—C2—C7—C8	−178.88 (17)	C10—N2—C11—N3	−0.28 (19)
C1—C2—C7—C8	0.62 (19)	N5—N2—C11—N3	177.50 (17)
C1—N1—C8—O2	−177.62 (17)	C10—N2—C11—S1	178.06 (14)
C9—N1—C8—O2	−2.9 (3)	N5—N2—C11—S1	−4.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5M···O2i	0.92 (2)	2.29 (2)	3.151 (2)	155.6 (19)
N5—H5N···S1ii	0.83 (2)	2.60 (2)	3.430 (2)	177.4 (18)
N3—H3N···O1iii	0.84 (2)	1.98 (2)	2.811 (2)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5M⋯O2i	0.92 (2)	2.29 (2)	3.151 (2)	155.6 (19)
N5—H5N⋯S1ii	0.83 (2)	2.60 (2)	3.430 (2)	177.4 (18)
N3—H3N⋯O1iii	0.84 (2)	1.98 (2)	2.811 (2)	169 (2)

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