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

Yunus, U.; Tahir, M.K.; Bhatti, M.H.; Yousaf, N.; Helliwell, M.

doi:10.1107/S1600536808001189

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Pages o476-o477

doi:10.1107/S1600536808001189

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

Uzma Yunus,^a Mohammad Kalim Tahir,^a Moazzam Hussain Bhatti,^a ^* Naveeda Yousaf ^a and Madeleine Helliwell ^b

^aDepartment of Chemistry, Allama Iqbal Open University, Islamabad, Pakistan, and ^bSchool of Chemistry, University of Manchester, Manchester M30 9PL, England
^*Correspondence e-mail: moazzamhussain_b@yahoo.com

(Received 21 November 2007; accepted 11 January 2008; online 23 January 2008)

The title compound, C₁₁H₉N₅O₂S, was synthesized from N-phthaloylglycine and thiocarbohydrazide 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 molecule 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 intermolecular hydrogen bonding linking the molecules 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_r = 275.29
Orthorhombic, P n a 2₁
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[F² > 2σ(F²)] = 0.028
wR(F²) = 0.069
S = 1.04
2361 reflections
184 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ), with 1091 Friedel pairs
Flack parameter: −0.04 (6)

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) x-1, y, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (iii) $[-x, -y+1, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

Phthalimide and its derivatives such as N-phthaloylamino acids are used for the synthesis of peptide bonds in solid phase synthesis (Eugenio et al., 2004; Chandrasekhar et al., 1999). Such phthalimide derivatives undergo photochemical reactions such as photochemical decomposition and decarboxylation (Görner et al., 2002). Moreover N-phthaloylamino acids and their derivatives possess a wide range of biological activities such as hypolipidemic (Neto et al., 1993) analgesic (Antunes et al., 1998) antimicrobial (Matijević-Sosa & Cvetnić, 2005) and DNA cleaving abilities (Brana & Ramos, 2001). Among the N-phthaloylamino acids, N-phthaloylglycine has been the most widely studied. Such studies include cleavage of N-phthaloylglycine with various amines (Khan & Ismail, 2002), metal complexes with interesting supramolecular structures (Barooah et al., 2006b) and adduct formation of N-phthaloylglycine with various aromatic amines and hydroxyl-aromatics (Barooah et al., 2006a). The heterocyclic derivatives of N-phthaloylglycine are also reported in literature such as oxadiazole (Antunes et al., 1998) and benzoxazinone (Shariat & Abdollahi, 2004). Keeping in view the importance of structural and biological aspects of N-phthaloylamino acids, the present work is aiming to incorporate 1,2,4-triazole ring with N-phthaloylglycine moiety. To the best of our knowledge this is the first crystal structure report on the 1,2,4-triazole derivative of N-phthaloylglycine.

The crystallographic analysis demonstrates that the title compound (I) exists as the thione form rather than the thiol as shown in scheme 1 and Fig. 1. The triazole ring is essentially planar. The C?S bond length [1.6758 (19) Å] is slightly longer than a pure double bond [1.61 Å] (Allen et al., 1987) and is comparable with analogous compounds (Zhang et al., 2004; Xu et al.,2005). The CN bond distances of the triazole ring are in the range 1.297 (2)–1.374 (2) Å in which the N4—C10 bond shows double bond character. The other CN bonds have values intermediate between those expected for single and double C—N bonds [1.47 and 1.27 Å respectively (Allen et al., 1987)] among which the N2—C11 bond length is slightly longer than that of N3—C11 (Wang et al., 1998). The NN bond lengths and all bond angles in triazole ring show no significant difference when compared to analogous compounds.

The phthalimide is also planar and all bond lengths and angles in the phthalimide ring are within normal ranges (Ng, 1992). The dihedral angle between the isoindoline and triazole ring systems is 82.24 (5)°, indicating the nonplanarity of the molecule as a whole.

The molecules are linked into pairs by the intermolecular hydrogen bond N5—H5N···S1 (symmetry equivalent x + 1/2, -y + 3/2, z) and then into sheets by the N3—H3N···O1 (-x, -y + 1, z - 1/2) contact, and finally into a three-dimensional network by the hydrogen bonds N5—H5M···O2 (symmetry equivalent x - 1, y, z) linking the sheets in the a direction.

Related literature top

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 top

The title compound (I) was synthesized by the reaction of N-phthaloylglycine and thiocarbohydrazide by the fusion method. A mixture of N-phthaloylglycine (0.01 mol) and thiocarbohydrazide (0.01 mol) contained in a round bottom flask was heated until the contents melted. The mixture was kept at this temperature for 25–30 min. after cooling to room temperature the mixture was triturated with methanol and the solid obtained was filtered, washed with methanol and recrystallized from a mixture (1:1) of ethanol and acetonitrile to obtain suitable crystals for x-ray analysis.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); 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 (Version 6.12; Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Version 6.12; Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. Plot of the title compound with ellipsoids drawn at the 50% probability level.
	Fig. 2. Packing of the title compound viewed down a, showing hydrogen bonding contacts with dashed lines.

2-(4-Amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3- ylmethyl)isoindoline-1,3-dione top

Crystal data top

C₁₁H₉N₅O₂S	F(000) = 568
M_r = 275.29	D_x = 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 = 3.6–26.4°
b = 19.952 (4) Å	µ = 0.28 mm⁻¹
c = 11.336 (3) Å	T = 100 K
V = 1175.2 (4) Å³	Plate, colourless
Z = 4	0.60 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2361 independent reflections
Radiation source: fine-focus sealed tube	2281 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 26.4°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker 2001)	h = −6→6
T_min = 0.849, T_max = 0.946	k = −24→17
6288 measured reflections	l = −14→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.069	w = 1/[σ²(F_o²) + (0.0413P)² + 0.1704P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2361 reflections	Δρ_max = 0.30 e Å⁻³
184 parameters	Δρ_min = −0.16 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1091 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (6)

Crystal data top

C₁₁H₉N₅O₂S	V = 1175.2 (4) Å³
M_r = 275.29	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 5.1961 (11) Å	µ = 0.28 mm⁻¹
b = 19.952 (4) Å	T = 100 K
c = 11.336 (3) Å	0.60 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2361 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2001)	2281 reflections with I > 2σ(I)
T_min = 0.849, T_max = 0.946	R_int = 0.023
6288 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.069	Δρ_max = 0.30 e Å⁻³
S = 1.04	Δρ_min = −0.16 e Å⁻³
2361 reflections	Absolute structure: Flack (1983), 1091 Friedel pairs
184 parameters	Absolute structure parameter: −0.04 (6)
1 restraint

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z; (ii) x+1/2, −y+3/2, z; (iii) −x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₉N₅O₂S
M_r	275.29
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	5.1961 (11), 19.952 (4), 11.336 (3)
V (Å³)	1175.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.60 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker 2001)
T_min, T_max	0.849, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	6288, 2361, 2281
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.069, 1.04
No. of reflections	2361
No. of parameters	184
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.16
Absolute structure	Flack (1983), 1091 Friedel pairs
Absolute structure parameter	−0.04 (6)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Version 6.12; Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z; (ii) x+1/2, −y+3/2, z; (iii) −x, −y+1, z−1/2.

Acknowledgements

The authors gratefully acknowledge Allama Iqbal Open University, Islamabad, Pakistan, for providing research facilities.

References

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Volume 64| Part 2| February 2008| Pages o476-o477

doi:10.1107/S1600536808001189

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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