Crystal structure of 3-[(E)-2-(4-phenyl-1,3-thia­zol-2-yl)hydrazin-1-yl­idene]indolin-2-one

Halasangi, B.M.; Badami, P.S.; Patil, S.A.; Anil Kumar, G.N.

doi:10.1107/S1600536814022715

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1177-o1178

doi:10.1107/S1600536814022715

Open

access

Crystal structure of 3-[(E)-2-(4-phenyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]indolin-2-one

Bhimashankar M. Halasangi,^a Prema S. Badami,^b Sangamesh A. Patil ^a and G. N. Anil Kumar ^c ^*

^aDepartment of Chemistry, Karnatak University, Dharwad, India, ^bDepartment of Chemistry, Shri Sharanabasaveshwar College of Science, Gulbarga 585 102, India, and ^cDepartment of Physics, M S Ramaiah Institute of Technology, Bangalore 560 054, Karnataka, India
^*Correspondence e-mail: anilgn@msrit.edu

Edited by A. J. Lough, University of Toronto, Canada (Received 4 October 2014; accepted 16 October 2014; online 24 October 2014)

In the title molecule, C₁₇H₁₂N₄OS, the thiazole ring forms a dihedral angle of 10.8 (2)° with the phenyl ring and an angle of 3.1 (3)° with the indole ring system [which has a maximum deviation of 0.035 (2) Å]. The dihedral angle between the planes of the phenyl ring and the indole ring system is 11.5 (1)°. An intramolecular N—H⋯O hydrogen bond is observed. In the crystal, pairs of N—H⋯O hydrogen bonds form inversion dimers with an R²₂(8) graph-set motif.

Keywords: crystal structure; indolinone; hydrazine; 1,3-thiazole; hydrogen bonding; biological activity.

CCDC reference: 1029498

1. Related literature

For the biological activities of substituted thiazoles, see: Ali et al. (2011 ); Bharti et al. (2010 ); Kondratieva et al. (2007 ). For a related structure, see: Sadık et al. (2004 ).

2. Experimental

2.1. Crystal data

C₁₇H₁₂N₄OS
M_r = 320.37
Monoclinic, P 2₁ /c
a = 17.7108 (8) Å
b = 5.1411 (2) Å
c = 15.9065 (6) Å
β = 94.706 (3)°
V = 1443.45 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.35 × 0.31 × 0.25 mm

2.2. Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.887, T_max = 0.934
11530 measured reflections
3142 independent reflections
2124 reflections with I > 2σ(I)
R_int = 0.039

2.3. Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.109
S = 1.09
3142 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	2.12	2.771 (2)	133
N4—H4⋯O1ⁱ	0.86	2.11	2.922 (2)	158
Symmetry code: (i) -x, -y, -z+1.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and CAMERON (Watkin et al., 1993 ); software used to prepare material for publication: PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1029498

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814022715/lh5732sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814022715/lh5732Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814022715/lh5732Isup3.cml

checkCIF report

Experimental top

Synthesis and crystallization top

An ethanolic solution of 1.81g (0.01 M) of 2-hydrazino-4-phenylthiazole was added drop wise to an etanolic solution of 1.47g (0.01 M) of isatin with constant stirring. After the complete addition, the reaction mixture was stirred further for 8-9 hrs until the solid separated out from the reaction mixture. The separated solid was filtered and washed with cold alcohol, dried and recrystallized from DMF (Yield: 95 %. MP: 443-446K). Block-shaped colourless crystals were obtained by slow evaporation of a solution of the title compound at room temperature in DMF:water in the ratio 2:1.

Refinement top

H atoms were placed in idealized positions and refined using a riding-model approximation with N—H = 0.86 Å, C—H = 0.93 Å and with U_iso(H) = 1.2U_eq(N,C).

Comment top

Isatin derivatives and compounds containing a thiazole ring are class of organic compounds which have fascinated many synthetic researchers due to their wide range of biological activity ( Ali et al., 2011; Bharti et al., 2010; Kondratieva et al., 2007).

The molecular structure of the title compound is shown in Fig. 1. An intramolecular N—H···O hydrogen bond is observed. The thiazole ring is essentially planar with a maximum deviation of 0.005 (2) Å for atom N1. The thiazole ring (S1/C9/N1/C7/C8) forms dihedral angles of 10.8 (2)° with the phenyl ring (C1–C6) and 3.1 (3)° with the indole ring system (C10—C16/N4/C17, with a maximum deviation of 0.035 (2)Å for atom C17). The dihedral angle between the phenyl ring and the indole ring system is 11.5 (1)Å. In the crystal, pairs of N—H···O hydrogen bonds form inversion dimers (Fig. 2). A closely related structure appears in the literature (Sadik, et al., 2004).

Related literature top

For the biological activities of substituted thiazoles, see: Ali et al. (2011); Bharti et al. (2010); Kondratieva et al. (2007). For a related structure, see: Sadik et al. (2004).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. The dashed line indicates an intramolecular N—H···N bond

Fig. 2. Part of the crystal structure with hydrogen bonds indicated as dotted lines

3-[(E)-2-(4-Phenyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]indolin-2-one top

Crystal data top

C₁₇H₁₂N₄OS	Z = 4
M_r = 320.37	F(000) = 664
Monoclinic, P2₁/c	D_x = 1.474 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 17.7108 (8) Å	µ = 0.23 mm⁻¹
b = 5.1411 (2) Å	T = 296 K
c = 15.9065 (6) Å	Block, colourless
β = 94.706 (3)°	0.35 × 0.31 × 0.25 mm
V = 1443.45 (10) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2124 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 27.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
T_min = 0.887, T_max = 0.934	k = −6→6
11530 measured reflections	l = −20→20
3142 independent 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0451P)² + 0.0098P] where P = (F_o² + 2F_c²)/3
3142 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₇H₁₂N₄OS	V = 1443.45 (10) Å³
M_r = 320.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.7108 (8) Å	µ = 0.23 mm⁻¹
b = 5.1411 (2) Å	T = 296 K
c = 15.9065 (6) Å	0.35 × 0.31 × 0.25 mm
β = 94.706 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3142 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2124 reflections with I > 2σ(I)
T_min = 0.887, T_max = 0.934	R_int = 0.039
11530 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.09	Δρ_max = 0.20 e Å⁻³
3142 reflections	Δρ_min = −0.25 e Å⁻³
208 parameters

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	0.33816 (3)	0.66660 (12)	0.39879 (3)	0.04097 (19)
O1	0.08908 (8)	0.2212 (3)	0.51706 (8)	0.0481 (4)
N1	0.28727 (8)	0.7985 (3)	0.54037 (9)	0.0325 (4)
N2	0.21944 (9)	0.4599 (3)	0.46996 (9)	0.0369 (4)
H2	0.1873	0.4489	0.5075	0.044*
N3	0.21516 (9)	0.3013 (3)	0.40283 (9)	0.0341 (4)
N4	0.05982 (9)	−0.1170 (3)	0.42364 (9)	0.0387 (5)
H4	0.0225	−0.1842	0.4474	0.046*
C1	0.43038 (11)	1.3281 (4)	0.58140 (12)	0.0359 (5)
H1	0.4504	1.335	0.5292	0.043*
C2	0.45583 (11)	1.5006 (4)	0.64372 (12)	0.0419 (5)
H2A	0.4931	1.6214	0.6335	0.05*
C3	0.42631 (12)	1.4945 (4)	0.72089 (12)	0.0410 (5)
H3	0.4433	1.6113	0.7629	0.049*
C4	0.37150 (12)	1.3150 (4)	0.73568 (12)	0.0415 (5)
H4A	0.3512	1.3113	0.7877	0.05*
C5	0.34649 (11)	1.1406 (4)	0.67384 (12)	0.0376 (5)
H5	0.3098	1.0188	0.6849	0.045*
C6	0.37525 (10)	1.1438 (4)	0.59528 (11)	0.0304 (5)
C7	0.34960 (10)	0.9552 (4)	0.52935 (11)	0.0309 (5)
C8	0.38282 (11)	0.9102 (4)	0.45680 (11)	0.0367 (5)
H8	0.4247	1.0007	0.4406	0.044*
C9	0.27677 (11)	0.6406 (4)	0.47676 (11)	0.0314 (5)
C10	0.16106 (11)	0.1315 (4)	0.39588 (11)	0.0319 (5)
C11	0.14763 (10)	−0.0560 (4)	0.32827 (11)	0.0317 (5)
C12	0.18154 (11)	−0.1039 (4)	0.25430 (12)	0.0409 (5)
H12	0.222	−0.003	0.2397	0.049*
C13	0.15406 (12)	−0.3045 (4)	0.20274 (12)	0.0451 (6)
H13	0.1762	−0.3386	0.1528	0.054*
C14	0.09393 (12)	−0.4556 (4)	0.22454 (12)	0.0422 (6)
H14	0.0768	−0.5912	0.1893	0.051*
C15	0.05887 (11)	−0.4091 (4)	0.29754 (12)	0.0392 (5)
H15	0.0183	−0.51	0.312	0.047*
C16	0.08638 (10)	−0.2078 (4)	0.34775 (11)	0.0319 (5)
C17	0.10069 (11)	0.0896 (4)	0.45404 (12)	0.0362 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0424 (3)	0.0466 (4)	0.0351 (3)	−0.0080 (3)	0.0099 (2)	−0.0052 (2)
O1	0.0479 (9)	0.0568 (11)	0.0417 (8)	−0.0142 (8)	0.0156 (7)	−0.0154 (8)
N1	0.0296 (9)	0.0333 (11)	0.0350 (8)	−0.0022 (8)	0.0050 (7)	−0.0018 (8)
N2	0.0329 (10)	0.0424 (12)	0.0363 (9)	−0.0091 (9)	0.0080 (7)	−0.0058 (8)
N3	0.0328 (9)	0.0359 (11)	0.0335 (8)	−0.0026 (9)	0.0026 (7)	−0.0024 (8)
N4	0.0354 (10)	0.0422 (12)	0.0400 (9)	−0.0129 (9)	0.0112 (7)	−0.0035 (8)
C1	0.0343 (11)	0.0375 (14)	0.0362 (10)	−0.0027 (10)	0.0056 (8)	0.0039 (10)
C2	0.0377 (12)	0.0398 (15)	0.0478 (12)	−0.0074 (11)	0.0010 (9)	−0.0001 (11)
C3	0.0436 (13)	0.0342 (14)	0.0442 (12)	−0.0026 (11)	−0.0030 (9)	−0.0071 (10)
C4	0.0454 (13)	0.0432 (15)	0.0366 (11)	−0.0002 (12)	0.0078 (9)	−0.0046 (10)
C5	0.0359 (12)	0.0366 (14)	0.0411 (11)	−0.0069 (11)	0.0085 (9)	−0.0020 (10)
C6	0.0291 (11)	0.0275 (12)	0.0343 (10)	0.0043 (10)	0.0010 (8)	0.0020 (9)
C7	0.0289 (10)	0.0285 (12)	0.0354 (10)	−0.0006 (10)	0.0026 (8)	0.0023 (9)
C8	0.0345 (11)	0.0377 (14)	0.0385 (11)	−0.0086 (10)	0.0071 (9)	−0.0001 (10)
C9	0.0290 (11)	0.0309 (13)	0.0344 (10)	−0.0004 (10)	0.0026 (8)	0.0012 (9)
C10	0.0282 (11)	0.0341 (13)	0.0334 (10)	−0.0010 (10)	0.0025 (8)	0.0010 (9)
C11	0.0275 (10)	0.0331 (13)	0.0342 (10)	0.0012 (10)	0.0016 (8)	−0.0001 (9)
C12	0.0326 (12)	0.0505 (15)	0.0404 (11)	−0.0049 (11)	0.0080 (9)	−0.0022 (11)
C13	0.0370 (12)	0.0588 (17)	0.0398 (11)	0.0042 (12)	0.0047 (9)	−0.0104 (11)
C14	0.0381 (12)	0.0428 (15)	0.0445 (12)	0.0027 (11)	−0.0042 (9)	−0.0094 (11)
C15	0.0343 (12)	0.0387 (14)	0.0442 (11)	−0.0016 (11)	0.0013 (9)	−0.0029 (10)
C16	0.0279 (11)	0.0358 (13)	0.0321 (10)	0.0026 (10)	0.0026 (8)	−0.0003 (9)
C17	0.0322 (11)	0.0398 (14)	0.0368 (11)	−0.0016 (11)	0.0040 (9)	−0.0008 (10)

Geometric parameters (Å, º) top

S1—C8	1.711 (2)	C4—C5	1.377 (3)
S1—C9	1.7203 (19)	C4—H4A	0.93
O1—C17	1.240 (2)	C5—C6	1.388 (2)
N1—C9	1.299 (2)	C5—H5	0.93
N1—C7	1.389 (2)	C6—C7	1.472 (3)
N2—N3	1.341 (2)	C7—C8	1.358 (2)
N2—C9	1.374 (2)	C8—H8	0.93
N2—H2	0.86	C10—C11	1.449 (3)
N3—C10	1.294 (2)	C10—C17	1.486 (3)
N4—C17	1.352 (2)	C11—C12	1.386 (2)
N4—C16	1.411 (2)	C11—C16	1.392 (3)
N4—H4	0.86	C12—C13	1.381 (3)
C1—C2	1.378 (3)	C12—H12	0.93
C1—C6	1.391 (3)	C13—C14	1.385 (3)
C1—H1	0.93	C13—H13	0.93
C2—C3	1.373 (3)	C14—C15	1.382 (3)
C2—H2A	0.93	C14—H14	0.93
C3—C4	1.373 (3)	C15—C16	1.372 (3)
C3—H3	0.93	C15—H15	0.93

C8—S1—C9	87.69 (9)	C7—C8—S1	111.71 (15)
C9—N1—C7	109.19 (15)	C7—C8—H8	124.1
N3—N2—C9	117.83 (15)	S1—C8—H8	124.1
N3—N2—H2	121.1	N1—C9—N2	122.80 (17)
C9—N2—H2	121.1	N1—C9—S1	117.03 (15)
C10—N3—N2	118.11 (16)	N2—C9—S1	120.17 (14)
C17—N4—C16	111.08 (16)	N3—C10—C11	125.96 (17)
C17—N4—H4	124.5	N3—C10—C17	127.60 (18)
C16—N4—H4	124.5	C11—C10—C17	106.44 (17)
C2—C1—C6	121.10 (18)	C12—C11—C16	119.27 (18)
C2—C1—H1	119.5	C12—C11—C10	133.79 (19)
C6—C1—H1	119.5	C16—C11—C10	106.93 (16)
C3—C2—C1	120.2 (2)	C13—C12—C11	118.73 (19)
C3—C2—H2A	119.9	C13—C12—H12	120.6
C1—C2—H2A	119.9	C11—C12—H12	120.6
C2—C3—C4	119.63 (19)	C12—C13—C14	120.71 (19)
C2—C3—H3	120.2	C12—C13—H13	119.6
C4—C3—H3	120.2	C14—C13—H13	119.6
C3—C4—C5	120.37 (19)	C15—C14—C13	121.4 (2)
C3—C4—H4A	119.8	C15—C14—H14	119.3
C5—C4—H4A	119.8	C13—C14—H14	119.3
C4—C5—C6	121.01 (19)	C16—C15—C14	117.20 (19)
C4—C5—H5	119.5	C16—C15—H15	121.4
C6—C5—H5	119.5	C14—C15—H15	121.4
C5—C6—C1	117.73 (18)	C15—C16—C11	122.65 (18)
C5—C6—C7	121.26 (18)	C15—C16—N4	128.34 (18)
C1—C6—C7	121.00 (17)	C11—C16—N4	109.01 (17)
C8—C7—N1	114.38 (17)	O1—C17—N4	126.73 (19)
C8—C7—C6	126.00 (18)	O1—C17—C10	126.84 (19)
N1—C7—C6	119.59 (16)	N4—C17—C10	106.42 (17)

C9—N2—N3—C10	−179.69 (17)	N2—N3—C10—C17	0.7 (3)
C6—C1—C2—C3	−0.6 (3)	N3—C10—C11—C12	−3.6 (4)
C1—C2—C3—C4	0.2 (3)	C17—C10—C11—C12	176.1 (2)
C2—C3—C4—C5	0.4 (3)	N3—C10—C11—C16	177.11 (18)
C3—C4—C5—C6	−0.7 (3)	C17—C10—C11—C16	−3.2 (2)
C4—C5—C6—C1	0.3 (3)	C16—C11—C12—C13	−1.0 (3)
C4—C5—C6—C7	179.04 (18)	C10—C11—C12—C13	179.7 (2)
C2—C1—C6—C5	0.3 (3)	C11—C12—C13—C14	−0.2 (3)
C2—C1—C6—C7	−178.37 (17)	C12—C13—C14—C15	0.9 (3)
C9—N1—C7—C8	0.9 (2)	C13—C14—C15—C16	−0.3 (3)
C9—N1—C7—C6	−177.30 (17)	C14—C15—C16—C11	−0.9 (3)
C5—C6—C7—C8	−167.50 (19)	C14—C15—C16—N4	178.32 (18)
C1—C6—C7—C8	11.2 (3)	C12—C11—C16—C15	1.6 (3)
C5—C6—C7—N1	10.4 (3)	C10—C11—C16—C15	−178.92 (17)
C1—C6—C7—N1	−170.89 (17)	C12—C11—C16—N4	−177.75 (17)
N1—C7—C8—S1	−0.5 (2)	C10—C11—C16—N4	1.7 (2)
C6—C7—C8—S1	177.49 (15)	C17—N4—C16—C15	−178.68 (18)
C9—S1—C8—C7	0.06 (16)	C17—N4—C16—C11	0.7 (2)
C7—N1—C9—N2	179.57 (17)	C16—N4—C17—O1	176.05 (19)
C7—N1—C9—S1	−0.8 (2)	C16—N4—C17—C10	−2.7 (2)
N3—N2—C9—N1	−178.05 (17)	N3—C10—C17—O1	4.6 (3)
N3—N2—C9—S1	2.4 (2)	C11—C10—C17—O1	−175.10 (19)
C8—S1—C9—N1	0.48 (16)	N3—C10—C17—N4	−176.72 (18)
C8—S1—C9—N2	−179.92 (16)	C11—C10—C17—N4	3.6 (2)
N2—N3—C10—C11	−179.72 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	2.12	2.771 (2)	133
N4—H4···O1ⁱ	0.86	2.11	2.922 (2)	158

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	2.12	2.771 (2)	133
N4—H4···O1ⁱ	0.86	2.11	2.922 (2)	158

Symmetry code: (i) −x, −y, −z+1.

Acknowledgements

USIC, Karnatak University, Dharwad, is greatly acknowledged for the single-crystal XRD data collection. BMH is grateful to the UGC for financial support in the form of an RFSMS scholarship.

References

Ali, M. A., Mirza, A. H., Bakar, H. J. H. A. & Bernhardt, P. V. (2011). Polyhedron, 30, 556–564. Web of Science CSD CrossRef CAS Google Scholar
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Bharti, S. K., Nath, G., Tilak, R. & Singh, S. K. (2010). Eur. J. Med. Chem. 45, 651–660. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kondratieva, M. L., Pepeleva, A. V., Belskaia, N. P., Koksharov, A. V., Groundwater, P. V., Robeyns, K., Van Meervelt, L., Dehaen, W., Fan, Z. J. & Bakulev, V. A. (2007). Tetrahedron, 63, 3042–3048. Web of Science CSD CrossRef CAS Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Sadık, G., Necmi, D., Ibrahim, Y., Alaaddin, Ç. & Dinçer, M. (2004). Acta Cryst. E60, o889–o891. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Watkin, D. M., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1177-o1178

doi:10.1107/S1600536814022715

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Crystal structure of 3-[(E)-2-(4-phenyl-1,3-thia­zol-2-yl)hydrazin-1-yl­­idene]indolin-2-one

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 3-[(E)-2-(4-phenyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]indolin-2-one