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

Pervez, H.; Iqbal, M.S.; Saira, N.; Yaqub, M.; Tahir, M.N.

doi:10.1107/S1600536810018052

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1404

https://doi.org/10.1107/S1600536810018052

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

Humayun Pervez,^a Mohammad S. Iqbal,^b Naveeda Saira,^a Muhammad Yaqub ^a and M. Nawaz Tahir ^c ^*

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

(Received 6 May 2010; accepted 15 May 2010; online 22 May 2010)

In the title compound, C₁₆H₁₄N₄O₂S, intramolecular N—H⋯N hydrogen bonding forms an S(5) ring, whereas N—H⋯O and C—H⋯S interactions complete S(6) ring motifs. In the crystal, molecules form inversion dimers due to N—H⋯O interactions. The dimers are interlinked through N—H⋯S hydrogen bonds and π–π interactions occur with a centroid–centroid distance of 3.8422 (11) Å between the methoxy-containing benzene ring and the five-membered heterocyclic ring.

Related literature

For the preparation and structures of biologically important N⁴-aryl-substituted isatin-3-thiosemicarbazones, see: Pervez et al. (2007 , 2008 , 2009 , 2010a ). For a related structure, see: Pervez et al. (2010b ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₄N₄O₂S
M_r = 326.37
Monoclinic, P 2₁ /n
a = 15.1793 (5) Å
b = 7.2473 (2) Å
c = 15.4764 (5) Å
β = 111.179 (2)°
V = 1587.55 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.34 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.946, T_max = 0.960
13861 measured reflections
3925 independent reflections
2898 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.125
S = 1.04
3925 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.35 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	2.04	2.875 (2)	164
N3—H3A⋯O1	0.86	2.06	2.7441 (19)	136
N4—H4A⋯N2	0.86	2.19	2.620 (2)	110
N4—H4A⋯S1ⁱⁱ	0.86	2.87	3.5806 (16)	141
C11—H11⋯S1	0.93	2.74	3.212 (2)	112
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S1600536810018052/si2262sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810018052/si2262Isup2.hkl

checkCIF report

Comment top

In continuation of our work on the synthesis of medicinally important organic molecules (Pervez et al., 2007, 2008, 2009, 2010a), we report herein the structure and synthesis of the title compound (I, Fig. 1).

The crystal structure of (II) i.e. 4-(2-fluorophenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazide has been published (Pervez et al., 2010b). The title compound (I) differs from (II) due to the attachment of methoxy group at position-3 instead of fluoro at position-2 of the phenyl ring substituted at N^4^ of the thiosemicarbazone moiety.

In (I) the 2-oxoindolin A (C1–C8/N1/O1), thiosemicarbazide B (N2/N3/C9/S1/N4) and the 3-methoxyphenyl C (C10—C16/O2) are planar with r. m. s. deviations of 0.0178, 0.0244 and 0.0149 Å, respectively. The dihedral angle between A/B, A/C and B/C is 8.71 (5)°, 33.59 (3)° and 39.32 (3)°, 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 dimerised (Fig. 2) due to intermolecular H-bonding of N—H···O type with R₂²(8) ring motifs. The dimers are interlinked through N—H···S type of H-bonding. There exist π···π interaction at a distance of 3.8422 (11) Å between the benzene ring (C10—C15) and the heterocyclic ring (N1/C7/C2/C1/C8).

Related literature top

For the preparation and structures of biologically important N⁴-aryl-substituted isatin-3-thiosemicarbazones, see: Pervez et al. (2007, 2008, 2009, 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-methoxyphenyl)thiosemicarbazide (0.99 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 refluxing was collected by suction filtration. Thorough washing with hot ethanol followed by ether afforded the target compound (I) in pure form (1.25 g, 77%), m. p. 477 K (d). The single crystals of (I) were grown in acetone by slow evaporation at room temperature.

Structure description top

For the preparation and structures of biologically important N⁴-aryl-substituted isatin-3-thiosemicarbazones, see: Pervez et al. (2007, 2008, 2009, 2010a). For a related structure, see: Pervez et al. (2010b). For graph-set notation, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii. The dotted lines indicate the intra-molecular H-bondings.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form dimers which are interlinked.

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

Crystal data top

C₁₆H₁₄N₄O₂S	F(000) = 680
M_r = 326.37	D_x = 1.366 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2898 reflections
a = 15.1793 (5) Å	θ = 3.2–28.3°
b = 7.2473 (2) Å	µ = 0.22 mm⁻¹
c = 15.4764 (5) Å	T = 296 K
β = 111.179 (2)°	Prism, yellow
V = 1587.55 (9) Å³	0.34 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3925 independent reflections
Radiation source: fine-focus sealed tube	2898 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.3°, θ_min = 3.2°
ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
T_min = 0.946, T_max = 0.960	l = −20→19
13861 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0539P)² + 0.6227P] where P = (F_o² + 2F_c²)/3
3925 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₆H₁₄N₄O₂S	V = 1587.55 (9) Å³
M_r = 326.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.1793 (5) Å	µ = 0.22 mm⁻¹
b = 7.2473 (2) Å	T = 296 K
c = 15.4764 (5) Å	0.34 × 0.22 × 0.20 mm
β = 111.179 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3925 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2898 reflections with I > 2σ(I)
T_min = 0.946, T_max = 0.960	R_int = 0.028
13861 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.04	Δρ_max = 0.36 e Å⁻³
3925 reflections	Δρ_min = −0.35 e Å⁻³
209 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.19826 (11)	0.3610 (2)	0.45348 (11)	0.0329 (3)
C2	0.26044 (11)	0.3126 (2)	0.54720 (11)	0.0345 (3)
C3	0.35347 (12)	0.2547 (3)	0.58412 (12)	0.0434 (4)
H3	0.3882	0.2332	0.5464	0.052*
C4	0.39313 (14)	0.2298 (3)	0.67919 (13)	0.0515 (5)
H4	0.4555	0.1908	0.7057	0.062*
C5	0.34181 (15)	0.2617 (3)	0.73516 (13)	0.0529 (5)
H5	0.3705	0.2446	0.7988	0.063*
C6	0.24859 (14)	0.3187 (3)	0.69884 (12)	0.0491 (5)
H6	0.2140	0.3403	0.7367	0.059*
C7	0.20928 (11)	0.3419 (2)	0.60448 (11)	0.0382 (4)
C8	0.10524 (11)	0.4125 (2)	0.46058 (11)	0.0359 (4)
C9	0.17432 (11)	0.4498 (2)	0.22293 (11)	0.0360 (4)
C10	0.30202 (12)	0.3962 (2)	0.16100 (12)	0.0388 (4)
C11	0.24941 (12)	0.3445 (2)	0.07119 (12)	0.0407 (4)
H11	0.1865	0.3103	0.0552	0.049*
C12	0.29128 (13)	0.3440 (3)	0.00497 (13)	0.0446 (4)
C13	0.38568 (14)	0.3931 (3)	0.02993 (15)	0.0539 (5)
H13	0.4139	0.3948	−0.0143	0.065*
C14	0.43705 (14)	0.4392 (3)	0.11998 (16)	0.0554 (5)
H14	0.5006	0.4689	0.1366	0.066*
C15	0.39605 (13)	0.4423 (3)	0.18678 (14)	0.0477 (4)
H15	0.4313	0.4748	0.2476	0.057*
C16	0.14733 (15)	0.2526 (3)	−0.11290 (15)	0.0613 (6)
H16A	0.1142	0.3578	−0.1023	0.092*
H16B	0.1387	0.1496	−0.0777	0.092*
H16C	0.1230	0.2222	−0.1776	0.092*
N1	0.11680 (10)	0.3984 (2)	0.55058 (10)	0.0429 (4)
H1	0.0733	0.4210	0.5725	0.051*
N2	0.22156 (9)	0.36975 (19)	0.38155 (9)	0.0351 (3)
N3	0.15482 (9)	0.4293 (2)	0.30214 (9)	0.0374 (3)
H3A	0.0992	0.4548	0.3013	0.045*
N4	0.26118 (10)	0.3955 (2)	0.23067 (10)	0.0416 (4)
H4A	0.2966	0.3552	0.2842	0.050*
O1	0.03312 (8)	0.45962 (19)	0.39631 (8)	0.0452 (3)
O2	0.24526 (10)	0.2944 (2)	−0.08484 (9)	0.0610 (4)
S1	0.09025 (3)	0.53985 (8)	0.13109 (3)	0.04856 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0311 (7)	0.0360 (8)	0.0318 (8)	0.0010 (6)	0.0115 (6)	−0.0041 (6)
C2	0.0357 (8)	0.0370 (9)	0.0304 (8)	0.0024 (6)	0.0115 (6)	−0.0028 (6)
C3	0.0409 (9)	0.0480 (10)	0.0403 (9)	0.0111 (7)	0.0136 (7)	−0.0015 (8)
C4	0.0456 (10)	0.0572 (12)	0.0423 (10)	0.0146 (9)	0.0045 (8)	0.0006 (9)
C5	0.0585 (12)	0.0603 (12)	0.0312 (9)	0.0100 (9)	0.0060 (8)	0.0039 (8)
C6	0.0547 (11)	0.0628 (12)	0.0320 (9)	0.0061 (9)	0.0182 (8)	−0.0004 (8)
C7	0.0370 (8)	0.0444 (9)	0.0329 (8)	0.0019 (7)	0.0123 (7)	−0.0013 (7)
C8	0.0306 (7)	0.0442 (9)	0.0335 (8)	−0.0012 (6)	0.0121 (6)	−0.0050 (7)
C9	0.0361 (8)	0.0396 (9)	0.0331 (8)	−0.0034 (7)	0.0136 (7)	−0.0010 (7)
C10	0.0408 (9)	0.0398 (9)	0.0411 (9)	0.0054 (7)	0.0211 (7)	0.0075 (7)
C11	0.0412 (9)	0.0431 (10)	0.0421 (9)	0.0028 (7)	0.0200 (7)	0.0032 (7)
C12	0.0518 (10)	0.0442 (10)	0.0445 (10)	0.0062 (8)	0.0253 (8)	0.0032 (8)
C13	0.0548 (11)	0.0636 (13)	0.0570 (12)	0.0033 (10)	0.0367 (10)	0.0059 (10)
C14	0.0414 (10)	0.0658 (13)	0.0656 (13)	−0.0035 (9)	0.0272 (10)	0.0046 (10)
C15	0.0415 (9)	0.0565 (12)	0.0465 (10)	0.0005 (8)	0.0174 (8)	0.0036 (9)
C16	0.0634 (13)	0.0705 (15)	0.0487 (12)	−0.0020 (11)	0.0187 (10)	−0.0053 (10)
N1	0.0337 (7)	0.0646 (10)	0.0332 (7)	0.0050 (7)	0.0154 (6)	−0.0018 (7)
N2	0.0345 (7)	0.0396 (8)	0.0317 (7)	0.0018 (6)	0.0124 (6)	−0.0014 (6)
N3	0.0303 (6)	0.0520 (9)	0.0304 (7)	0.0027 (6)	0.0114 (5)	0.0015 (6)
N4	0.0355 (7)	0.0579 (10)	0.0330 (7)	0.0072 (6)	0.0143 (6)	0.0079 (6)
O1	0.0303 (6)	0.0680 (9)	0.0342 (6)	0.0061 (5)	0.0081 (5)	−0.0031 (6)
O2	0.0614 (9)	0.0838 (11)	0.0445 (8)	0.0019 (8)	0.0272 (7)	−0.0089 (7)
S1	0.0377 (2)	0.0708 (4)	0.0363 (2)	0.0074 (2)	0.01228 (18)	0.0104 (2)

Geometric parameters (Å, º) top

C1—N2	1.286 (2)	C10—C11	1.381 (2)
C1—C2	1.459 (2)	C10—N4	1.425 (2)
C1—C8	1.503 (2)	C11—C12	1.387 (2)
C2—C3	1.383 (2)	C11—H11	0.9300
C2—C7	1.390 (2)	C12—O2	1.359 (2)
C3—C4	1.386 (3)	C12—C13	1.389 (3)
C3—H3	0.9300	C13—C14	1.370 (3)
C4—C5	1.378 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.386 (3)
C5—C6	1.384 (3)	C14—H14	0.9300
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.374 (2)	C16—O2	1.422 (3)
C6—H6	0.9300	C16—H16A	0.9600
C7—N1	1.410 (2)	C16—H16B	0.9600
C8—O1	1.2319 (19)	C16—H16C	0.9600
C8—N1	1.343 (2)	N1—H1	0.8600
C9—N4	1.339 (2)	N2—N3	1.3504 (18)
C9—N3	1.369 (2)	N3—H3A	0.8600
C9—S1	1.6624 (17)	N4—H4A	0.8600
C10—C15	1.377 (2)

N2—C1—C2	126.25 (14)	C10—C11—H11	120.3
N2—C1—C8	127.64 (14)	C12—C11—H11	120.3
C2—C1—C8	105.94 (13)	O2—C12—C11	123.55 (17)
C3—C2—C7	120.33 (15)	O2—C12—C13	116.72 (17)
C3—C2—C1	132.91 (15)	C11—C12—C13	119.72 (18)
C7—C2—C1	106.72 (13)	C14—C13—C12	119.75 (18)
C2—C3—C4	117.73 (17)	C14—C13—H13	120.1
C2—C3—H3	121.1	C12—C13—H13	120.1
C4—C3—H3	121.1	C13—C14—C15	121.26 (18)
C5—C4—C3	121.22 (17)	C13—C14—H14	119.4
C5—C4—H4	119.4	C15—C14—H14	119.4
C3—C4—H4	119.4	C10—C15—C14	118.52 (18)
C4—C5—C6	121.48 (17)	C10—C15—H15	120.7
C4—C5—H5	119.3	C14—C15—H15	120.7
C6—C5—H5	119.3	O2—C16—H16A	109.5
C7—C6—C5	117.13 (17)	O2—C16—H16B	109.5
C7—C6—H6	121.4	H16A—C16—H16B	109.5
C5—C6—H6	121.4	O2—C16—H16C	109.5
C6—C7—C2	122.09 (16)	H16A—C16—H16C	109.5
C6—C7—N1	128.44 (16)	H16B—C16—H16C	109.5
C2—C7—N1	109.47 (14)	C8—N1—C7	111.39 (14)
O1—C8—N1	127.11 (15)	C8—N1—H1	124.3
O1—C8—C1	126.47 (15)	C7—N1—H1	124.3
N1—C8—C1	106.42 (13)	C1—N2—N3	116.95 (13)
N4—C9—N3	114.35 (14)	N2—N3—C9	121.05 (13)
N4—C9—S1	128.21 (13)	N2—N3—H3A	119.5
N3—C9—S1	117.43 (12)	C9—N3—H3A	119.5
C15—C10—C11	121.28 (16)	C9—N4—C10	127.93 (14)
C15—C10—N4	118.06 (16)	C9—N4—H4A	116.0
C11—C10—N4	120.61 (15)	C10—N4—H4A	116.0
C10—C11—C12	119.44 (16)	C12—O2—C16	117.57 (15)

N2—C1—C2—C3	−4.6 (3)	C10—C11—C12—C13	0.8 (3)
C8—C1—C2—C3	179.95 (19)	O2—C12—C13—C14	−178.02 (19)
N2—C1—C2—C7	172.98 (16)	C11—C12—C13—C14	0.9 (3)
C8—C1—C2—C7	−2.51 (18)	C12—C13—C14—C15	−1.6 (3)
C7—C2—C3—C4	−0.8 (3)	C11—C10—C15—C14	1.2 (3)
C1—C2—C3—C4	176.49 (19)	N4—C10—C15—C14	178.50 (17)
C2—C3—C4—C5	0.0 (3)	C13—C14—C15—C10	0.6 (3)
C3—C4—C5—C6	0.4 (3)	O1—C8—N1—C7	−179.55 (17)
C4—C5—C6—C7	0.1 (3)	C1—C8—N1—C7	0.0 (2)
C5—C6—C7—C2	−0.9 (3)	C6—C7—N1—C8	177.47 (19)
C5—C6—C7—N1	−179.92 (19)	C2—C7—N1—C8	−1.6 (2)
C3—C2—C7—C6	1.3 (3)	C2—C1—N2—N3	−175.68 (15)
C1—C2—C7—C6	−176.60 (17)	C8—C1—N2—N3	−1.2 (2)
C3—C2—C7—N1	−179.52 (16)	C1—N2—N3—C9	177.49 (15)
C1—C2—C7—N1	2.6 (2)	N4—C9—N3—N2	3.9 (2)
N2—C1—C8—O1	5.7 (3)	S1—C9—N3—N2	−175.20 (12)
C2—C1—C8—O1	−178.91 (17)	N3—C9—N4—C10	178.85 (16)
N2—C1—C8—N1	−173.84 (17)	S1—C9—N4—C10	−2.1 (3)
C2—C1—C8—N1	1.57 (19)	C15—C10—N4—C9	142.08 (19)
C15—C10—C11—C12	−1.8 (3)	C11—C10—N4—C9	−40.6 (3)
N4—C10—C11—C12	−179.12 (16)	C11—C12—O2—C16	4.2 (3)
C10—C11—C12—O2	179.65 (17)	C13—C12—O2—C16	−176.89 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.04	2.875 (2)	164
N3—H3A···O1	0.86	2.06	2.7441 (19)	136
N4—H4A···N2	0.86	2.19	2.620 (2)	110
N4—H4A···S1ⁱⁱ	0.86	2.87	3.5806 (16)	141
C11—H11···S1	0.93	2.74	3.212 (2)	112
C8—O1···Cg3ⁱⁱⁱ	1.23 (1)	3.64 (1)	3.7399 (17)	85 (1)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₄O₂S
M_r	326.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	15.1793 (5), 7.2473 (2), 15.4764 (5)
β (°)	111.179 (2)
V (Å³)	1587.55 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.34 × 0.22 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.946, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	13861, 3925, 2898
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.125, 1.04
No. of reflections	3925
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.35

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), 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	0.8600	2.0400	2.875 (2)	164.00
N3—H3A···O1	0.8600	2.0600	2.7441 (19)	136.00
N4—H4A···N2	0.8600	2.1900	2.620 (2)	110.00
N4—H4A···S1ⁱⁱ	0.8600	2.8700	3.5806 (16)	141.00
C11—H11···S1	0.9300	2.7400	3.212 (2)	112.00

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

HP, MSI and NS thank the Higher Education Commission (HEC), Pakistan, for financial assistance under the National Research Program for Universities (project No. 20–873/R&D/07/452).

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