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

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

doi:10.1107/S1600536810021264

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1609

doi:10.1107/S1600536810021264

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

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

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

(Received 2 June 2010; accepted 3 June 2010; online 9 June 2010)

The title compound, C₁₇H₁₆N₄OS, is stabilized in the form of a two-dimensional polymeric network due to intermolecular N—H⋯S and N—H⋯O hydrogen bonds. An intramolecular N—H⋯N hydrogen bond forms an S(5) ring, whereas interactions of the N—H⋯O and C—H⋯S types complete S(6) ring motifs. π–π interactions with a centroid–centroid distance of 3.6514 (10) Å are found between the ethyl-substituted benzene ring and the heterocyclic ring of the isatin derivative.

Related literature

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

Experimental

Crystal data

C₁₇H₁₆N₄OS
M_r = 324.40
Monoclinic, C 2/c
a = 25.6769 (7) Å
b = 7.4340 (2) Å
c = 16.6548 (5) Å
β = 96.248 (1)°
V = 3160.22 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.32 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.942, T_max = 0.952
11310 measured reflections
2823 independent reflections
2400 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.092
S = 1.04
2823 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.18 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	2.07	2.88 (17)	157
N3—H3A⋯O1	0.86	2.10	2.7711 (17)	134
N4—H4A⋯N2	0.86	2.13	2.5745 (18)	111
N4—H4A⋯S1ⁱⁱ	0.86	2.87	3.5220 (15)	133
C15—H15⋯S1	0.93	2.85	3.283 (2)	110
Symmetry codes: (i) $[-x, y, -z+{\script{1\over 2}}]$ ; (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: 10.1107/S1600536810021264/bq2219sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021264/bq2219Isup2.hkl

checkCIF report

Comment top

The title compound (I), (Fig 1) is being reported in continuation of synthesizing biologically important isatin derivatives (Pervez et al., 2007).

The crystal structure of (II) i.e. 4-(2-fluorophenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazide (Pervez et al., 2010) has been published. The title compound (I) differs from (II) due to the attachment of ethyl instead of fluoro group at position-2 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 0.0178, 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 interlinked through N—H···O and N–H···S intermolecular H-bondings. Due to these interactions infinite two-dimensional polymeric network exists. There exist π···π interaction at a distance of 3.6514 (10) Å between the benzene ring (C10—C15) and the heterocyclic ring (N1/C7/C2/C1/C8).

Related literature top

For the preparation of biologically important N⁴-arylsubstituted isatins-3-thiosemicarbazones, see: Pervez et al. (2007). For a related structure, see: Pervez et al. (2010): 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-(2-ethylphenyl)thiosemicarbazide (0.98 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 (1.42 g, 88%), m. p. 485 K (d). The single crystals of (I) were grown in ethyl acetate by slow evaporation at room temperature.

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. The dotted lines indicate the intra-molecular H-bondings.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form two-dimensional polymeric network.

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

Crystal data top

C₁₇H₁₆N₄OS	F(000) = 1360
M_r = 324.40	D_x = 1.364 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2400 reflections
a = 25.6769 (7) Å	θ = 2.9–25.3°
b = 7.4340 (2) Å	µ = 0.22 mm⁻¹
c = 16.6548 (5) Å	T = 296 K
β = 96.248 (1)°	Prism, yellow
V = 3160.22 (15) Å³	0.32 × 0.24 × 0.22 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	2823 independent reflections
Radiation source: fine-focus sealed tube	2400 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 8.10 pixels mm^-1	θ_max = 25.3°, θ_min = 2.9°
ω scans	h = −30→30
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −7→8
T_min = 0.942, T_max = 0.952	l = −19→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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0406P)² + 2.640P] where P = (F_o² + 2F_c²)/3
2823 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₇H₁₆N₄OS	V = 3160.22 (15) Å³
M_r = 324.40	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 25.6769 (7) Å	µ = 0.22 mm⁻¹
b = 7.4340 (2) Å	T = 296 K
c = 16.6548 (5) Å	0.32 × 0.24 × 0.22 mm
β = 96.248 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2823 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2400 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.952	R_int = 0.022
11310 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.04	Δρ_max = 0.16 e Å⁻³
2823 reflections	Δρ_min = −0.18 e Å⁻³
209 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
S1	0.23890 (2)	−0.14366 (7)	0.38931 (2)	0.0442 (2)
O1	0.06872 (4)	−0.02675 (19)	0.27866 (7)	0.0479 (4)
N1	0.02670 (5)	0.0792 (2)	0.15804 (8)	0.0442 (5)
N2	0.16415 (5)	0.02887 (19)	0.19012 (8)	0.0349 (4)
N3	0.17539 (5)	−0.03419 (19)	0.26578 (8)	0.0372 (4)
N4	0.26102 (5)	−0.0071 (2)	0.24633 (8)	0.0393 (4)
C1	0.06870 (6)	0.0291 (2)	0.20906 (10)	0.0381 (5)
C2	0.04184 (6)	0.1426 (2)	0.08419 (10)	0.0391 (5)
C3	0.01121 (7)	0.2144 (3)	0.01920 (11)	0.0516 (6)
C4	0.03640 (8)	0.2668 (3)	−0.04645 (11)	0.0547 (7)
C5	0.09005 (8)	0.2485 (3)	−0.04709 (11)	0.0495 (6)
C6	0.12070 (7)	0.1798 (2)	0.01934 (9)	0.0409 (5)
C7	0.09608 (6)	0.1274 (2)	0.08544 (9)	0.0341 (5)
C8	0.11566 (6)	0.0567 (2)	0.16408 (9)	0.0333 (5)
C9	0.22671 (6)	−0.0580 (2)	0.29697 (9)	0.0342 (5)
C10	0.31682 (6)	−0.0090 (2)	0.25921 (10)	0.0365 (5)
C11	0.34405 (6)	−0.0684 (2)	0.19598 (10)	0.0392 (5)
C12	0.39859 (7)	−0.0623 (3)	0.20944 (12)	0.0511 (7)
C13	0.42445 (7)	0.0001 (3)	0.28101 (13)	0.0585 (7)
C14	0.39670 (7)	0.0588 (3)	0.34154 (12)	0.0546 (7)
C15	0.34255 (7)	0.0550 (3)	0.33083 (11)	0.0452 (6)
C16	0.31486 (8)	−0.1327 (3)	0.11775 (11)	0.0495 (6)
C17	0.34737 (10)	−0.2230 (3)	0.05832 (13)	0.0717 (9)
H1	−0.00519	0.07323	0.16915	0.0531*
H3	−0.02481	0.22716	0.01929	0.0619*
H3A	0.15051	−0.05950	0.29454	0.0446*
H4	0.01673	0.31566	−0.09139	0.0656*
H4A	0.24765	0.03177	0.19999	0.0471*
H5	0.10561	0.28267	−0.09261	0.0594*
H6	0.15681	0.16924	0.01957	0.0490*
H12	0.41813	−0.10153	0.16896	0.0613*
H13	0.46088	0.00228	0.28809	0.0702*
H14	0.41418	0.10101	0.38969	0.0655*
H15	0.32347	0.09524	0.37168	0.0543*
H16A	0.29714	−0.03025	0.09104	0.0595*
H16B	0.28807	−0.21671	0.13056	0.0595*
H17A	0.37156	−0.13760	0.04015	0.1076*
H17B	0.32467	−0.26665	0.01289	0.1076*
H17C	0.36643	−0.32188	0.08436	0.1076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0421 (3)	0.0538 (3)	0.0371 (2)	0.0059 (2)	0.0058 (2)	0.0088 (2)
O1	0.0369 (6)	0.0701 (9)	0.0379 (7)	0.0024 (6)	0.0097 (5)	0.0099 (6)
N1	0.0265 (7)	0.0667 (10)	0.0396 (8)	−0.0015 (7)	0.0045 (6)	0.0036 (7)
N2	0.0306 (7)	0.0406 (8)	0.0334 (7)	0.0011 (6)	0.0036 (5)	0.0002 (6)
N3	0.0290 (7)	0.0488 (9)	0.0345 (7)	0.0018 (6)	0.0061 (5)	0.0052 (6)
N4	0.0294 (7)	0.0548 (9)	0.0339 (7)	0.0038 (6)	0.0043 (5)	0.0074 (6)
C1	0.0321 (8)	0.0449 (10)	0.0379 (9)	−0.0012 (7)	0.0060 (7)	−0.0007 (7)
C2	0.0345 (8)	0.0455 (10)	0.0368 (8)	−0.0021 (7)	0.0013 (7)	−0.0010 (7)
C3	0.0384 (9)	0.0649 (13)	0.0495 (10)	0.0047 (9)	−0.0042 (8)	0.0045 (9)
C4	0.0584 (12)	0.0610 (13)	0.0418 (10)	0.0041 (10)	−0.0071 (9)	0.0092 (9)
C5	0.0600 (12)	0.0511 (12)	0.0378 (9)	−0.0038 (9)	0.0069 (8)	0.0048 (8)
C6	0.0425 (9)	0.0449 (10)	0.0356 (9)	−0.0032 (8)	0.0063 (7)	−0.0013 (7)
C7	0.0331 (8)	0.0358 (9)	0.0329 (8)	−0.0007 (7)	0.0020 (6)	−0.0035 (7)
C8	0.0304 (8)	0.0374 (9)	0.0325 (8)	−0.0002 (7)	0.0049 (6)	−0.0018 (7)
C9	0.0314 (8)	0.0344 (9)	0.0372 (9)	0.0042 (6)	0.0053 (6)	−0.0032 (7)
C10	0.0317 (8)	0.0386 (9)	0.0394 (9)	0.0028 (7)	0.0054 (7)	0.0084 (7)
C11	0.0408 (9)	0.0359 (9)	0.0424 (9)	0.0052 (7)	0.0118 (7)	0.0102 (7)
C12	0.0419 (10)	0.0567 (12)	0.0583 (12)	0.0099 (9)	0.0214 (9)	0.0154 (9)
C13	0.0308 (9)	0.0763 (15)	0.0682 (13)	−0.0005 (9)	0.0051 (9)	0.0178 (11)
C14	0.0410 (10)	0.0684 (14)	0.0523 (11)	−0.0099 (9)	−0.0040 (8)	0.0095 (10)
C15	0.0391 (9)	0.0541 (11)	0.0426 (10)	−0.0009 (8)	0.0048 (7)	0.0029 (8)
C16	0.0587 (11)	0.0465 (11)	0.0448 (10)	0.0051 (9)	0.0119 (8)	0.0032 (8)
C17	0.0976 (17)	0.0655 (15)	0.0572 (13)	−0.0001 (13)	0.0317 (12)	−0.0070 (11)

Geometric parameters (Å, º) top

S1—C9	1.6625 (15)	C10—C15	1.384 (2)
O1—C1	1.231 (2)	C11—C16	1.508 (3)
N1—C1	1.351 (2)	C11—C12	1.395 (2)
N1—C2	1.411 (2)	C12—C13	1.380 (3)
N2—N3	1.3460 (19)	C13—C14	1.368 (3)
N2—C8	1.290 (2)	C14—C15	1.383 (3)
N3—C9	1.374 (2)	C16—C17	1.519 (3)
N4—C9	1.339 (2)	C3—H3	0.9300
N4—C10	1.426 (2)	C4—H4	0.9300
N1—H1	0.8600	C5—H5	0.9300
N3—H3A	0.8600	C6—H6	0.9300
N4—H4A	0.8600	C12—H12	0.9300
C1—C8	1.501 (2)	C13—H13	0.9300
C2—C7	1.395 (2)	C14—H14	0.9300
C2—C3	1.375 (2)	C15—H15	0.9300
C3—C4	1.386 (3)	C16—H16A	0.9700
C4—C5	1.386 (3)	C16—H16B	0.9700
C5—C6	1.384 (2)	C17—H17A	0.9600
C6—C7	1.384 (2)	C17—H17B	0.9600
C7—C8	1.450 (2)	C17—H17C	0.9600
C10—C11	1.398 (2)

S1···C15	3.283 (2)	C1···H1ⁱⁱⁱ	2.7600
S1···N4ⁱ	3.5220 (15)	C1···H3A	2.4900
S1···H15	2.8500	C5···H17A^vii	3.0500
S1···H6ⁱⁱ	3.1900	C9···H15	2.8900
S1···H4Aⁱ	2.8700	C9···H16B^iv	2.8500
S1···H16Aⁱ	3.0500	C12···H5^vii	2.8400
O1···N2	3.0226 (17)	C12···H17A	2.8800
O1···N3	2.7711 (17)	C12···H17C	2.8900
O1···C5ⁱⁱ	3.331 (2)	C16···H4A	2.6200
O1···N1ⁱⁱⁱ	2.8805 (17)	C17···H12	2.6000
O1···H1ⁱⁱⁱ	2.0700	H1···O1ⁱⁱⁱ	2.0700
O1···H3A	2.1000	H1···C1ⁱⁱⁱ	2.7600
N1···O1ⁱⁱⁱ	2.8805 (17)	H3A···O1	2.1000
N2···O1	3.0226 (17)	H3A···C1	2.4900
N2···N4	2.5745 (18)	H4A···N2	2.1300
N3···O1	2.7711 (17)	H4A···C16	2.6200
N4···C9^iv	3.437 (2)	H4A···H16A	2.3700
N4···N2	2.5745 (18)	H4A···H16B	2.4700
N4···S1^iv	3.5220 (15)	H4A···S1^iv	2.8700
N2···H4A	2.1300	H5···C12^vii	2.8400
N4···H16B	2.6300	H6···S1^vi	3.1900
N4···H16A	2.8500	H12···C17	2.6000
C1···C13^iv	3.509 (3)	H12···H17A	2.3500
C1···C12^iv	3.395 (3)	H12···H17C	2.4500
C2···C3^v	3.370 (3)	H13···H13^viii	2.4900
C2···C13^iv	3.526 (3)	H15···S1	2.8500
C3···C3^v	3.290 (3)	H15···C9	2.8900
C3···C2^v	3.370 (3)	H16A···N4	2.8500
C5···O1^vi	3.331 (2)	H16A···H4A	2.3700
C7···C14^iv	3.428 (3)	H16A···S1^iv	3.0500
C8···C12^iv	3.572 (3)	H16B···N4	2.6300
C9···N4ⁱ	3.437 (2)	H16B···H4A	2.4700
C12···C8ⁱ	3.572 (3)	H16B···C9ⁱ	2.8500
C12···C1ⁱ	3.395 (3)	H17A···C12	2.8800
C13···C2ⁱ	3.526 (3)	H17A···H12	2.3500
C13···C1ⁱ	3.509 (3)	H17A···C5^vii	3.0500
C14···C7ⁱ	3.428 (3)	H17C···C12	2.8900
C15···S1	3.283 (2)	H17C···H12	2.4500

C1—N1—C2	111.33 (13)	C12—C11—C16	123.02 (16)
N3—N2—C8	118.13 (13)	C11—C12—C13	122.01 (17)
N2—N3—C9	119.86 (13)	C12—C13—C14	120.24 (17)
C9—N4—C10	128.46 (14)	C13—C14—C15	119.71 (18)
C2—N1—H1	124.00	C10—C15—C14	119.83 (17)
C1—N1—H1	124.00	C11—C16—C17	116.51 (17)
C9—N3—H3A	120.00	C2—C3—H3	121.00
N2—N3—H3A	120.00	C4—C3—H3	121.00
C9—N4—H4A	116.00	C3—C4—H4	119.00
C10—N4—H4A	116.00	C5—C4—H4	119.00
O1—C1—N1	127.14 (14)	C4—C5—H5	120.00
O1—C1—C8	126.71 (14)	C6—C5—H5	120.00
N1—C1—C8	106.14 (13)	C5—C6—H6	121.00
N1—C2—C7	109.23 (13)	C7—C6—H6	121.00
C3—C2—C7	121.86 (15)	C11—C12—H12	119.00
N1—C2—C3	128.89 (15)	C13—C12—H12	119.00
C2—C3—C4	117.02 (17)	C12—C13—H13	120.00
C3—C4—C5	121.90 (18)	C14—C13—H13	120.00
C4—C5—C6	120.63 (17)	C13—C14—H14	120.00
C5—C6—C7	118.08 (17)	C15—C14—H14	120.00
C2—C7—C6	120.47 (15)	C10—C15—H15	120.00
C2—C7—C8	106.88 (13)	C14—C15—H15	120.00
C6—C7—C8	132.64 (15)	C11—C16—H16A	108.00
N2—C8—C7	126.10 (14)	C11—C16—H16B	108.00
N2—C8—C1	127.49 (14)	C17—C16—H16A	108.00
C1—C8—C7	106.38 (13)	C17—C16—H16B	108.00
S1—C9—N3	118.38 (12)	H16A—C16—H16B	107.00
S1—C9—N4	128.35 (12)	C16—C17—H17A	109.00
N3—C9—N4	113.27 (13)	C16—C17—H17B	109.00
C11—C10—C15	121.82 (15)	C16—C17—H17C	109.00
N4—C10—C15	120.28 (15)	H17A—C17—H17B	109.00
N4—C10—C11	117.83 (14)	H17A—C17—H17C	109.00
C10—C11—C12	116.40 (15)	H17B—C17—H17C	109.00
C10—C11—C16	120.58 (15)

C1—N1—C2—C3	−176.03 (18)	C2—C3—C4—C5	−0.1 (3)
C2—N1—C1—O1	177.74 (16)	C3—C4—C5—C6	−1.3 (3)
C2—N1—C1—C8	−1.78 (17)	C4—C5—C6—C7	1.1 (3)
C1—N1—C2—C7	2.28 (18)	C5—C6—C7—C8	−177.87 (17)
N3—N2—C8—C7	178.61 (14)	C5—C6—C7—C2	0.5 (2)
C8—N2—N3—C9	−177.12 (14)	C2—C7—C8—N2	−177.51 (15)
N3—N2—C8—C1	0.9 (2)	C6—C7—C8—N2	1.1 (3)
N2—N3—C9—S1	−177.65 (12)	C6—C7—C8—C1	179.21 (16)
N2—N3—C9—N4	2.2 (2)	C2—C7—C8—C1	0.65 (16)
C10—N4—C9—S1	−1.7 (3)	N4—C10—C11—C12	177.69 (16)
C9—N4—C10—C15	−45.5 (2)	N4—C10—C11—C16	−1.6 (2)
C10—N4—C9—N3	178.48 (15)	C15—C10—C11—C12	1.0 (2)
C9—N4—C10—C11	137.74 (17)	C15—C10—C11—C16	−178.32 (17)
O1—C1—C8—N2	−0.7 (3)	N4—C10—C15—C14	−177.59 (18)
O1—C1—C8—C7	−178.83 (16)	C11—C10—C15—C14	−0.9 (3)
N1—C1—C8—N2	178.80 (16)	C10—C11—C12—C13	−0.4 (3)
N1—C1—C8—C7	0.68 (16)	C16—C11—C12—C13	178.81 (19)
N1—C2—C3—C4	179.90 (17)	C10—C11—C16—C17	−170.19 (16)
C7—C2—C3—C4	1.8 (3)	C12—C11—C16—C17	10.6 (3)
N1—C2—C7—C6	179.51 (14)	C11—C12—C13—C14	−0.1 (3)
N1—C2—C7—C8	−1.72 (17)	C12—C13—C14—C15	0.2 (3)
C3—C2—C7—C6	−2.0 (2)	C13—C14—C15—C10	0.4 (3)
C3—C2—C7—C8	176.74 (16)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱⁱⁱ	0.8600	2.0700	2.8805 (17)	157.00
N3—H3A···O1	0.8600	2.1000	2.7711 (17)	134.00
N4—H4A···N2	0.8600	2.1300	2.5745 (18)	111.00
N4—H4A···S1^iv	0.8600	2.8700	3.5220 (15)	133.00
C15—H15···S1	0.9300	2.8500	3.283 (2)	110.00

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₄OS
M_r	324.40
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	25.6769 (7), 7.4340 (2), 16.6548 (5)
β (°)	96.248 (1)
V (Å³)	3160.22 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.32 × 0.24 × 0.22

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.942, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	11310, 2823, 2400
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.04
No. of reflections	2823
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.18

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	2.0700	2.8805 (17)	157.00
N3—H3A···O1	0.8600	2.1000	2.7711 (17)	134.00
N4—H4A···N2	0.8600	2.1300	2.5745 (18)	111.00
N4—H4A···S1ⁱⁱ	0.8600	2.8700	3.5220 (15)	133.00
C15—H15···S1	0.9300	2.8500	3.283 (2)	110.00

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

Acknowledgements

HP, MY and MR thank the Ministry of Science & Technology (MoST), Government of Pakistan, for partial financial assistance under `Projects for the Strengthening of S & T Education in Universities' (project No. P&D/S&T/2001/231).

References

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