4-(3-Iodo­phen­yl)-1-(2-oxoindolin-3-yl­idene)thio­semicarbazide

Pervez, H.; Yaqub, M.; Ramzan, M.; Tahir, M.N.

doi:10.1107/S1600536810021938

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1629

doi:10.1107/S1600536810021938

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4-(3-Iodophenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazide

Humayun Pervez,^a Muhammad Yaqub,^a Muhammad Ramzan ^a and M. Nawaz Tahir ^b ^*

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 2 June 2010; accepted 8 June 2010; online 16 June 2010)

In the title compound, C₁₅H₁₁IN₄OS, intramolecular N—H⋯N, N—H⋯O and C—H⋯S interactions generate one S(5) and two S(6) ring motifs. In the crystal, molecules form centrosymmetric dimers via pairs of N—H⋯O interactions, generating R₂²(8) ring motifs. In addition a short intermolecular I⋯S contact of 3.352 (3) Å is observed.

Related literature

For the preparation of biologically important N⁴-aryl-substituted isatin-3-thiosemicarbazones, see: Pervez et al. (2007 , 2008 , 2010a ). For a related structure, see: Pervez et al. (2010b ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₁IN₄OS
M_r = 422.24
Monoclinic, P 2₁ /c
a = 5.7620 (3) Å
b = 16.7989 (11) Å
c = 16.152 (1) Å
β = 100.153 (4)°
V = 1538.96 (16) Å³
Z = 4
Mo Kα radiation
μ = 2.22 mm⁻¹
T = 296 K
0.32 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.742, T_max = 0.752
11310 measured reflections
2778 independent reflections
1677 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.157
S = 1.01
2778 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 2.76 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.09	2.939 (9)	169
N3—H3A⋯O1	0.86	2.07	2.761 (9)	137
N4—H4A⋯N2	0.86	2.18	2.618 (9)	111
C15—H15⋯S1	0.93	2.51	3.183 (10)	129
Symmetry code: (i) -x-1, -y, -z+1.

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, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021938/gk2281sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021938/gk2281Isup2.hkl

checkCIF report

Comment top

As a part of our drug discovery program, we very recently reported the synthesis and biological evaluation of a number of N⁴-aryl substituted isatins-thiosemicarbazones (Pervez et al., 2007, 2008, 2010a). In continuation of the same, we report herein the structure and synthesis of the title compound (I, Fig. 1).

The crystal structure of (II) i.e. 4-(3-methoxyphenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazides has been published (Pervez et al., 2010b). The title compound differs from (II) due to the presence of iodo instead of methoxy function at position-3 of the phenyl ring substituted at N⁴ of the thiosemicarbazone moiety.

In (I) the 2-oxoindolin A (C1–C8/N1/O1), thiosemicarbazide B (N2/N3/C9/S1/N4) and phenyl ring of 2-ethylphenyl C (C10—C16) are planar with r. m. s. deviations of 0.0086, 0.0029 and 0.0414 Å, respectively. The dihedral angle between A/B, A/C and B/C is 4.65 (41)°, 11.89 (41)° and 13.37 (37)°, respectively. Due to intramolecular H-bondings (Table 1, Fig. 1), one S(5) and two S(6) (Bernstein et al., 1995) ring motifs are formed. The molecules are dimerized (Fig. 2) due to intermolecular H-bonding of N—H···O type with R₂²(8) ring motifs.

Related literature top

For the preparation of biologically important N⁴-aryl-substituted isatin-3-thiosemicarbazones, see: Pervez et al. (2007, 2008, 2010a). For a related structure, see: Pervez et al. (2010b). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

To a hot solution of isatin (0.74 g, 5.0 mmol) in ethanol (10 ml) containing a few drops of glacial acetic acid was added 4-(3-iodophenyl)thiosemicarbazide (1.47 g, 5.0 mmol) dissolved in ethanol (10 ml) under stirring. The reaction mixture was then heated under reflux for 2 h. The yellow crystalline solid formed during heating was collected by suction filtration. Thorough washing with hot ethanol followed by ether afforded the target compound (I) in pure form (1.77 g, 84%), m. p. 503 K (d). The single crystals of (I) were grown in acetone-ethanol (1:4) by diffusion method at room temperature.

Computing details top

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, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title molecule with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii. The dotted lines indicate intramolecular hydrogen bonds.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form dimers.

4-(3-Iodophenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazide top

Crystal data top

C₁₅H₁₁IN₄OS	F(000) = 824
M_r = 422.24	D_x = 1.822 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1677 reflections
a = 5.7620 (3) Å	θ = 2.7–25.3°
b = 16.7989 (11) Å	µ = 2.22 mm⁻¹
c = 16.152 (1) Å	T = 296 K
β = 100.153 (4)°	Needle, yellow
V = 1538.96 (16) Å³	0.32 × 0.14 × 0.12 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2778 independent reflections
Radiation source: fine-focus sealed tube	1677 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 8.10 pixels mm^-1	θ_max = 25.3°, θ_min = 2.7°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −20→20
T_min = 0.742, T_max = 0.752	l = −16→19
11310 measured reflections

Refinement top

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0776P)² + 1.1429P] where P = (F_o² + 2F_c²)/3
2778 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 2.76 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

C₁₅H₁₁IN₄OS	V = 1538.96 (16) Å³
M_r = 422.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.7620 (3) Å	µ = 2.22 mm⁻¹
b = 16.7989 (11) Å	T = 296 K
c = 16.152 (1) Å	0.32 × 0.14 × 0.12 mm
β = 100.153 (4)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2778 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1677 reflections with I > 2σ(I)
T_min = 0.742, T_max = 0.752	R_int = 0.022
11310 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 1.01	Δρ_max = 2.76 e Å⁻³
2778 reflections	Δρ_min = −0.48 e Å⁻³
199 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	1.07185 (10)	0.31162 (4)	0.23986 (4)	0.0483 (3)
S1	0.4332 (4)	0.20616 (18)	0.59942 (16)	0.0586 (10)
O1	−0.2092 (9)	0.0552 (4)	0.5161 (4)	0.045 (2)
N1	−0.4370 (12)	0.0106 (4)	0.3922 (4)	0.040 (3)
N2	0.0812 (11)	0.1226 (4)	0.3935 (4)	0.034 (2)
N3	0.1620 (11)	0.1406 (4)	0.4736 (4)	0.037 (3)
N4	0.4525 (10)	0.2139 (4)	0.4329 (4)	0.034 (2)
C1	−0.2557 (14)	0.0481 (5)	0.4378 (6)	0.039 (3)
C2	−0.4343 (14)	0.0140 (5)	0.3070 (6)	0.038 (3)
C3	−0.5883 (15)	−0.0147 (6)	0.2406 (6)	0.050 (3)
C4	−0.5463 (17)	−0.0022 (6)	0.1609 (7)	0.058 (4)
C5	−0.3504 (17)	0.0387 (6)	0.1472 (6)	0.055 (4)
C6	−0.1928 (16)	0.0702 (6)	0.2141 (6)	0.049 (3)
C7	−0.2329 (13)	0.0575 (5)	0.2942 (5)	0.035 (3)
C8	−0.1107 (13)	0.0803 (5)	0.3755 (5)	0.036 (3)
C9	0.3534 (13)	0.1884 (5)	0.4975 (5)	0.036 (3)
C10	0.6498 (14)	0.2638 (5)	0.4318 (5)	0.035 (3)
C11	0.7303 (13)	0.2695 (5)	0.3565 (6)	0.038 (3)
C12	0.9304 (14)	0.3131 (5)	0.3511 (5)	0.038 (3)
C13	1.0440 (15)	0.3535 (5)	0.4199 (6)	0.044 (3)
C14	0.9691 (16)	0.3505 (6)	0.4947 (6)	0.050 (3)
C15	0.7723 (16)	0.3050 (6)	0.5021 (6)	0.048 (3)
H1	−0.54474	−0.01324	0.41344	0.0478*
H3	−0.72140	−0.04269	0.24913	0.0602*
H3A	0.09085	0.12147	0.51176	0.0443*
H4	−0.65213	−0.02171	0.11525	0.0694*
H4A	0.38484	0.19719	0.38428	0.0404*
H5	−0.32307	0.04539	0.09258	0.0658*
H6	−0.06263	0.09934	0.20473	0.0588*
H11	0.64938	0.24387	0.30899	0.0460*
H13	1.17608	0.38384	0.41514	0.0529*
H14	1.04853	0.37862	0.54072	0.0598*
H15	0.72130	0.30179	0.55351	0.0580*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0373 (4)	0.0617 (5)	0.0487 (4)	0.0009 (3)	0.0153 (3)	0.0093 (3)
S1	0.0525 (15)	0.083 (2)	0.0409 (14)	−0.0148 (14)	0.0096 (11)	0.0018 (14)
O1	0.038 (3)	0.052 (4)	0.050 (4)	−0.003 (3)	0.021 (3)	−0.001 (3)
N1	0.034 (4)	0.039 (4)	0.052 (5)	−0.007 (3)	0.020 (3)	0.000 (4)
N2	0.026 (4)	0.041 (4)	0.038 (4)	−0.002 (3)	0.011 (3)	0.002 (3)
N3	0.032 (4)	0.048 (5)	0.034 (4)	−0.006 (3)	0.012 (3)	0.005 (4)
N4	0.026 (4)	0.037 (4)	0.040 (4)	−0.005 (3)	0.009 (3)	0.001 (3)
C1	0.030 (5)	0.033 (5)	0.058 (7)	0.004 (4)	0.023 (4)	0.005 (5)
C2	0.027 (4)	0.036 (5)	0.054 (6)	−0.002 (4)	0.013 (4)	0.008 (5)
C3	0.039 (5)	0.048 (6)	0.063 (7)	−0.014 (4)	0.010 (5)	0.002 (5)
C4	0.051 (6)	0.063 (7)	0.058 (7)	−0.013 (5)	0.006 (5)	−0.001 (6)
C5	0.063 (6)	0.063 (7)	0.039 (6)	−0.016 (5)	0.011 (5)	0.001 (5)
C6	0.049 (5)	0.049 (6)	0.051 (6)	−0.015 (5)	0.016 (5)	0.000 (5)
C7	0.036 (4)	0.032 (5)	0.040 (5)	−0.005 (4)	0.016 (4)	0.002 (4)
C8	0.027 (4)	0.044 (6)	0.039 (5)	0.006 (4)	0.010 (4)	0.007 (4)
C9	0.026 (4)	0.037 (5)	0.045 (5)	0.001 (4)	0.007 (4)	0.006 (4)
C10	0.035 (5)	0.036 (5)	0.036 (5)	0.005 (4)	0.010 (4)	0.003 (4)
C11	0.027 (4)	0.036 (5)	0.051 (6)	0.005 (4)	0.004 (4)	0.005 (5)
C12	0.029 (4)	0.035 (5)	0.049 (6)	0.009 (4)	0.008 (4)	0.010 (5)
C13	0.032 (5)	0.039 (6)	0.061 (7)	−0.004 (4)	0.005 (4)	0.003 (5)
C14	0.047 (6)	0.048 (6)	0.057 (6)	−0.012 (5)	0.014 (5)	−0.012 (5)
C15	0.040 (5)	0.055 (6)	0.052 (6)	−0.008 (5)	0.014 (4)	−0.005 (5)

Geometric parameters (Å, º) top

I1—C12	2.100 (8)	C5—C6	1.388 (14)
S1—C9	1.656 (8)	C6—C7	1.371 (12)
O1—C1	1.251 (11)	C7—C8	1.429 (11)
N1—C1	1.326 (11)	C10—C15	1.409 (13)
N1—C2	1.380 (11)	C10—C11	1.379 (12)
N2—N3	1.330 (9)	C11—C12	1.382 (11)
N2—C8	1.303 (10)	C12—C13	1.367 (12)
N3—C9	1.364 (10)	C13—C14	1.354 (13)
N4—C9	1.345 (10)	C14—C15	1.390 (14)
N4—C10	1.415 (10)	C3—H3	0.9300
N1—H1	0.8600	C4—H4	0.9300
N3—H3A	0.8600	C5—H5	0.9300
N4—H4A	0.8600	C6—H6	0.9300
C1—C8	1.517 (12)	C11—H11	0.9300
C2—C3	1.355 (13)	C13—H13	0.9300
C2—C7	1.417 (11)	C14—H14	0.9300
C3—C4	1.367 (14)	C15—H15	0.9300
C4—C5	1.372 (14)

I1···S1ⁱ	3.352 (3)	C9···O1^iv	3.344 (10)
I1···S1ⁱⁱ	3.979 (3)	C10···C8^iv	3.560 (12)
I1···H3ⁱⁱⁱ	3.2000	C11···C8^iv	3.307 (12)
I1···H4A^iv	3.3000	C11···N2^iv	3.180 (11)
S1···C15	3.183 (10)	C12···N2^iv	3.355 (11)
S1···I1^v	3.352 (3)	C13···N4^iv	3.303 (11)
S1···I1^vi	3.979 (3)	C13···C9^iv	3.414 (12)
S1···H15	2.5100	C14···C9^iv	3.505 (13)
O1···N2	3.028 (9)	C15···S1	3.183 (10)
O1···N3	2.761 (9)	C1···H3A	2.4700
O1···C9^vii	3.344 (10)	C1···H1^ix	2.9000
O1···C1^viii	3.168 (10)	C1···H3A^viii	3.0700
O1···O1^viii	3.157 (8)	C5···H13^x	3.0200
O1···N1^ix	2.939 (9)	C9···H15	2.8700
O1···C8^viii	3.241 (10)	C12···H3ⁱⁱⁱ	3.0400
O1···H3A	2.0700	C13···H4ⁱⁱⁱ	3.0600
O1···H1^ix	2.0900	C14···H5^xi	3.0500
N1···O1^ix	2.939 (9)	C15···H5^xi	3.0100
N2···O1	3.028 (9)	H1···O1^ix	2.0900
N2···N4	2.618 (9)	H1···C1^ix	2.9000
N2···C11^vii	3.180 (11)	H3···I1^xii	3.2000
N2···C12^vii	3.355 (11)	H3···C12^xii	3.0400
N3···O1	2.761 (9)	H3A···O1	2.0700
N4···C1^iv	3.247 (11)	H3A···C1	2.4700
N4···N2	2.618 (9)	H3A···C1^viii	3.0700
N4···C13^vii	3.303 (11)	H4···C13^xii	3.0600
N2···H4A	2.1800	H4A···I1^vii	3.3000
C1···N4^vii	3.247 (11)	H4A···N2	2.1800
C1···C9^vii	3.511 (12)	H4A···H11	2.2500
C1···O1^viii	3.168 (10)	H5···C14^xiii	3.0500
C8···O1^viii	3.241 (10)	H5···C15^xiii	3.0100
C8···C10^vii	3.560 (12)	H11···H4A	2.2500
C8···C11^vii	3.307 (12)	H13···C5^xiv	3.0200
C9···C14^vii	3.505 (13)	H15···S1	2.5100
C9···C1^iv	3.511 (12)	H15···C9	2.8700
C9···C13^vii	3.414 (12)

C1—N1—C2	112.8 (7)	S1—C9—N4	129.2 (6)
N3—N2—C8	118.6 (7)	C11—C10—C15	118.6 (8)
N2—N3—C9	122.4 (6)	N4—C10—C15	124.8 (7)
C9—N4—C10	130.6 (7)	N4—C10—C11	116.6 (7)
C2—N1—H1	124.00	C10—C11—C12	120.4 (8)
C1—N1—H1	124.00	I1—C12—C13	119.9 (6)
N2—N3—H3A	119.00	I1—C12—C11	120.1 (6)
C9—N3—H3A	119.00	C11—C12—C13	119.8 (8)
C10—N4—H4A	115.00	C12—C13—C14	121.7 (8)
C9—N4—H4A	115.00	C13—C14—C15	119.4 (9)
O1—C1—N1	127.9 (8)	C10—C15—C14	120.1 (8)
N1—C1—C8	105.9 (7)	C2—C3—H3	120.00
O1—C1—C8	126.3 (7)	C4—C3—H3	120.00
C3—C2—C7	120.5 (8)	C3—C4—H4	119.00
N1—C2—C3	130.8 (8)	C5—C4—H4	119.00
N1—C2—C7	108.7 (7)	C4—C5—H5	120.00
C2—C3—C4	119.4 (9)	C6—C5—H5	120.00
C3—C4—C5	121.1 (10)	C5—C6—H6	121.00
C4—C5—C6	120.6 (9)	C7—C6—H6	121.00
C5—C6—C7	118.7 (9)	C10—C11—H11	120.00
C6—C7—C8	133.5 (8)	C12—C11—H11	120.00
C2—C7—C6	119.8 (8)	C12—C13—H13	119.00
C2—C7—C8	106.7 (7)	C14—C13—H13	119.00
N2—C8—C1	126.3 (7)	C13—C14—H14	120.00
C1—C8—C7	105.9 (7)	C15—C14—H14	120.00
N2—C8—C7	127.8 (7)	C10—C15—H15	120.00
S1—C9—N3	117.2 (6)	C14—C15—H15	120.00
N3—C9—N4	113.6 (7)

C1—N1—C2—C3	−178.2 (9)	C3—C2—C7—C6	−0.4 (13)
C2—N1—C1—O1	−179.7 (8)	C3—C2—C7—C8	179.0 (8)
C2—N1—C1—C8	−0.6 (9)	C2—C3—C4—C5	0.2 (15)
C1—N1—C2—C7	0.2 (10)	C3—C4—C5—C6	−1.7 (16)
N3—N2—C8—C7	176.9 (8)	C4—C5—C6—C7	2.0 (15)
C8—N2—N3—C9	−176.1 (7)	C5—C6—C7—C8	179.8 (9)
N3—N2—C8—C1	−0.3 (12)	C5—C6—C7—C2	−1.0 (13)
N2—N3—C9—S1	179.6 (6)	C2—C7—C8—N2	−178.4 (8)
N2—N3—C9—N4	−1.0 (11)	C6—C7—C8—N2	0.9 (16)
C10—N4—C9—S1	−1.0 (13)	C6—C7—C8—C1	178.6 (10)
C9—N4—C10—C15	−7.2 (14)	C2—C7—C8—C1	−0.7 (9)
C10—N4—C9—N3	179.7 (7)	N4—C10—C11—C12	−176.1 (7)
C9—N4—C10—C11	170.5 (8)	C15—C10—C11—C12	1.6 (13)
O1—C1—C8—N2	−2.3 (14)	N4—C10—C15—C14	177.9 (8)
O1—C1—C8—C7	180.0 (8)	C11—C10—C15—C14	0.3 (14)
N1—C1—C8—N2	178.5 (8)	C10—C11—C12—I1	173.5 (6)
N1—C1—C8—C7	0.8 (9)	C10—C11—C12—C13	−2.7 (13)
N1—C2—C3—C4	179.0 (9)	I1—C12—C13—C14	−174.5 (7)
C7—C2—C3—C4	0.8 (14)	C11—C12—C13—C14	1.7 (13)
N1—C2—C7—C6	−179.0 (8)	C12—C13—C14—C15	0.3 (14)
N1—C2—C7—C8	0.4 (9)	C13—C14—C15—C10	−1.3 (14)

Symmetry codes: (i) x+1, −y+1/2, z−1/2; (ii) x, −y+1/2, z−1/2; (iii) −x, y+1/2, −z+1/2; (iv) x+1, y, z; (v) x−1, −y+1/2, z+1/2; (vi) x, −y+1/2, z+1/2; (vii) x−1, y, z; (viii) −x, −y, −z+1; (ix) −x−1, −y, −z+1; (x) −x+1, y−1/2, −z+1/2; (xi) x+1, −y+1/2, z+1/2; (xii) −x, y−1/2, −z+1/2; (xiii) x−1, −y+1/2, z−1/2; (xiv) −x+1, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^ix	0.86	2.09	2.939 (9)	169
N3—H3A···O1	0.86	2.07	2.761 (9)	137
N4—H4A···N2	0.86	2.18	2.618 (9)	111
C15—H15···S1	0.93	2.51	3.183 (10)	129

Symmetry code: (ix) −x−1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁IN₄OS
M_r	422.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	5.7620 (3), 16.7989 (11), 16.152 (1)
β (°)	100.153 (4)
V (Å³)	1538.96 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.22
Crystal size (mm)	0.32 × 0.14 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.742, 0.752
No. of measured, independent and observed [I > 2σ(I)] reflections	11310, 2778, 1677
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.157, 1.01
No. of reflections	2778
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.76, −0.48

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SAINT, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.09	2.939 (9)	169
N3—H3A···O1	0.86	2.07	2.761 (9)	137
N4—H4A···N2	0.86	2.18	2.618 (9)	111
C15—H15···S1	0.93	2.51	3.183 (10)	129

Symmetry code: (i) −x−1, −y, −z+1.

Acknowledgements

HP, MY and MR thank the Ministry of Science & Technology (MoST), Government of Pakistan, for partial financial assistance under the Projects for the Strengthening of S & T Education in Universities (project No. P&D/S&T/2001/231).

References

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