N′-[1-(2,4-Dioxo-3,4-dihydro-2H-1-benzopyran-3-yl­idene)eth­yl]thiophene-2-carbo­hydrazide

Helliwell, M.; Nasiopoulou, D.A.; Harris, P.A.; Kotali, A.; Joule, J.A.

doi:10.1107/S1600536811010907

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o1014

doi:10.1107/S1600536811010907

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N′-[1-(2,4-Dioxo-3,4-dihydro-2H-1-benzopyran-3-ylidene)ethyl]thiophene-2-carbohydrazide

Madeleine Helliwell,^a Despina A. Nasiopoulou,^b Philip A. Harris,^c Antigoni Kotali ^b ^* and John A. Joule ^a

^aThe School of Chemistry, The University of Manchester, Manchester M13 9PL, England, ^bLaboratory of Organic Chemistry, Department of Chemical Engineering, University of Thessaloniki, Thessaloniki 54124, Greece, and ^cGlaxoSmithKline, 1250 South Collegeville Road, P.O.Box 5089, Collegeville, PA 19426-0989, USA
^*Correspondence e-mail: kotali@eng.auth.gr

(Received 7 March 2011; accepted 23 March 2011; online 31 March 2011)

The title compound, C₁₆H₁₂N₂O₄S, was obtained by the condensation of 3-acetyl-4-hydroxycoumarin with thien-2-ylcarbonyl hydrazide. The pyran ring adopts a 2,4-dione tautomeric form. The benzopyran ring system is almost coplanar with the thiophene ring [dihedral angle 0.9 (2)°]. The exocyclic C=C double bond has an E geometry. The molecular conformation is stabilized by an intramolecular N—H⋯O hydrogen bond. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains along the a axis.

Related literature

For the synthesis, characterization and reactions of N-acyl hydrazones, see: Kotali (2009 ); Kotali et al., (2010 ).

Experimental

Crystal data

C₁₆H₁₂N₂O₄S
M_r = 328.34
Triclinic, $[P \overline 1]$
a = 4.8631 (11) Å
b = 11.833 (3) Å
c = 13.296 (3) Å
α = 107.106 (5)°
β = 100.376 (4)°
γ = 97.553 (4)°
V = 705.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 K
0.55 × 0.15 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer
3526 measured reflections
2441 independent reflections
1403 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.116
S = 0.87
2441 reflections
217 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O4	1.00 (4)	1.64 (5)	2.481 (4)	140 (4)
N1—H1N⋯O1ⁱ	0.92 (4)	1.93 (4)	2.841 (4)	177 (4)
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2002 ); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010907/rz2570sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811010907/rz2570Isup2.hkl

checkCIF report

Comment top

In the context of our ongoing studies on the synthesis, characterization and reactions of N-acyl hydrazones (Kotali, 2009, Kotali et al., 2010), we reacted 3-acetyl-4-hydroxycoumarin (1) with thien-2-ylcarboxylic acid hydrazide (2) anticipating the formation of the hydrazone (3) (Fig. 1). Spectroscopic measurements strongly suggested that the product adopts the tautomeric form (4). The X-ray determination here described confirmed this hypothesis (Figure 2).

The amide nitrogen, surprisingly, is substantially pyramidal with the sum of the angles of the three substituents amounting to 351.1°. The sum of the angles at the other nitrogen atom, which can be viewed as an enamine nitrogen, is 360.0°. This result illustrates the extensive conjugation between this nitrogen and the two carbonyl groups in the pyran ring via the exocyclic double bond. The benzopyran group is essentially coplanar with the thiophene ring, with a dihedral angle of 0.9 (2)°. The exocyclic C═C double bond has E geometry. An intramolecular H bond links N2 and O4 (Table 1), and intermolecular H bonds between N1 and O1 link the molecules into one-dimensional chains along the a axis (Figure 3).

Related literature top

For the synthesis, characterization and reactions of N-acyl hydrazones, see: Kotali (2009); Kotali et al., (2010).

Experimental top

Thien-2-ylcarboxylic acid hydrazide (1 mmol) was added to a solution of 3-acetyl-4-hydroxycoumarin (1 mmol) in propan-1-ol (20 ml). The mixture was heated at reflux for 24 h and then cooled to room temperature. The resulting precipitate was collected by filtration and dried to give N'-[1-(2,4-dioxo-2H-1-benzopyran-3(4H)- ylidene)ethyl]-thien-2-ylcarboxylic acid hydrazide as a solid (yield 94%). The compound was recrystallizated from propan-1-ol.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Reaction scheme.
	Fig. 2. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 3. Partial crystal packing of the title compound showing the intra- and intermolecular hydrogen bonds, the latter linking the molecules into one-dimensional chains along the a. H atoms not involved in hydrogen bonding are omitted.

N'-[1-(2,4-Dioxo-3,4-dihydro-2H-1-benzopyran-3- ylidene)ethyl]thiophene-2-carbohydrazide top

Crystal data top

C₁₆H₁₂N₂O₄S	Z = 2
M_r = 328.34	F(000) = 340
Triclinic, P1	D_x = 1.546 Mg m⁻³
Hall symbol: -P 1	Melting point = 501–501.5 K
a = 4.8631 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.833 (3) Å	Cell parameters from 557 reflections
c = 13.296 (3) Å	θ = 3.3–24.1°
α = 107.106 (5)°	µ = 0.25 mm⁻¹
β = 100.376 (4)°	T = 100 K
γ = 97.553 (4)°	Plate, colourless
V = 705.3 (3) Å³	0.55 × 0.15 × 0.08 mm

Data collection top

Bruker SMART APEX CCD diffractometer	1403 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.072
Graphite monochromator	θ_max = 25.0°, θ_min = 1.8°
phi and ω scans	h = −5→5
3526 measured reflections	k = −9→14
2441 independent reflections	l = −14→15

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	w = 1/[σ²(F_o²) + (0.0273P)²] where P = (F_o² + 2F_c²)/3
2441 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.33 e Å⁻³
6 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₆H₁₂N₂O₄S	γ = 97.553 (4)°
M_r = 328.34	V = 705.3 (3) Å³
Triclinic, P1	Z = 2
a = 4.8631 (11) Å	Mo Kα radiation
b = 11.833 (3) Å	µ = 0.25 mm⁻¹
c = 13.296 (3) Å	T = 100 K
α = 107.106 (5)°	0.55 × 0.15 × 0.08 mm
β = 100.376 (4)°

Data collection top

Bruker SMART APEX CCD diffractometer	1403 reflections with I > 2σ(I)
3526 measured reflections	R_int = 0.072
2441 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	6 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	Δρ_max = 0.33 e Å⁻³
2441 reflections	Δρ_min = −0.36 e Å⁻³
217 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	0.0444 (2)	0.21501 (11)	0.90847 (9)	0.0263 (3)
O1	−0.1997 (5)	0.2309 (2)	0.68338 (19)	0.0196 (7)
O2	−0.0262 (5)	0.2667 (2)	0.1854 (2)	0.0191 (7)
O3	0.2600 (5)	0.1509 (2)	0.2281 (2)	0.0199 (7)
O4	−0.2081 (5)	0.3697 (2)	0.4843 (2)	0.0189 (7)
N1	0.1959 (7)	0.1917 (3)	0.6226 (3)	0.0173 (8)
H1N	0.391 (9)	0.201 (4)	0.640 (3)	0.047 (15)*
N2	0.0996 (7)	0.2368 (3)	0.5397 (3)	0.0150 (8)
H2N	−0.014 (9)	0.302 (4)	0.552 (3)	0.048 (15)*
C1	0.2359 (8)	0.1294 (4)	0.9644 (3)	0.0252 (11)
H1	0.2486	0.1294	1.0365	0.030*
C2	0.3682 (8)	0.0614 (4)	0.8950 (3)	0.0262 (11)
H2	0.4810	0.0070	0.9124	0.031*
C3	0.3201 (8)	0.0801 (4)	0.7933 (3)	0.0208 (10)
H3	0.3987	0.0407	0.7351	0.025*
C4	0.1463 (8)	0.1620 (4)	0.7887 (3)	0.0147 (10)
C5	0.0318 (8)	0.1993 (3)	0.6974 (3)	0.0125 (9)
C6	0.1535 (8)	0.1983 (4)	0.4433 (3)	0.0133 (9)
C7	0.3201 (8)	0.1004 (4)	0.4210 (3)	0.0193 (10)
H7A	0.5221	0.1358	0.4335	0.029*
H7B	0.2502	0.0480	0.3456	0.029*
H7C	0.2976	0.0528	0.4692	0.029*
C8	0.0388 (8)	0.2517 (4)	0.3664 (3)	0.0141 (9)
C9	0.1028 (8)	0.2193 (4)	0.2600 (3)	0.0155 (10)
C10	−0.1924 (8)	0.3525 (4)	0.2107 (3)	0.0176 (10)
C11	−0.2969 (8)	0.3977 (4)	0.1301 (3)	0.0221 (11)
H11	−0.2520	0.3710	0.0614	0.027*
C12	−0.4677 (8)	0.4821 (4)	0.1510 (3)	0.0249 (11)
H12	−0.5401	0.5138	0.0960	0.030*
C13	−0.5364 (8)	0.5220 (4)	0.2519 (3)	0.0211 (10)
H13	−0.6553	0.5797	0.2656	0.025*
C14	−0.4275 (8)	0.4756 (4)	0.3307 (3)	0.0172 (10)
H14	−0.4735	0.5015	0.3993	0.021*
C15	−0.2522 (8)	0.3918 (4)	0.3123 (3)	0.0162 (10)
C16	−0.1403 (8)	0.3385 (4)	0.3938 (3)	0.0153 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0278 (7)	0.0360 (8)	0.0186 (6)	0.0138 (6)	0.0112 (5)	0.0073 (6)
O1	0.0102 (15)	0.0294 (18)	0.0222 (16)	0.0067 (14)	0.0062 (12)	0.0104 (14)
O2	0.0190 (16)	0.0247 (18)	0.0170 (15)	0.0095 (14)	0.0074 (13)	0.0077 (14)
O3	0.0189 (16)	0.0226 (18)	0.0207 (16)	0.0073 (14)	0.0109 (13)	0.0057 (14)
O4	0.0166 (16)	0.0256 (18)	0.0149 (15)	0.0064 (14)	0.0076 (13)	0.0041 (14)
N1	0.010 (2)	0.029 (2)	0.0117 (18)	0.0057 (17)	0.0024 (15)	0.0042 (17)
N2	0.0129 (19)	0.019 (2)	0.0143 (19)	0.0045 (17)	0.0017 (15)	0.0067 (17)
C1	0.021 (2)	0.040 (3)	0.014 (2)	0.005 (2)	0.0002 (19)	0.009 (2)
C2	0.020 (2)	0.036 (3)	0.026 (3)	0.010 (2)	0.004 (2)	0.013 (2)
C3	0.019 (2)	0.031 (3)	0.017 (2)	0.010 (2)	0.0077 (19)	0.010 (2)
C4	0.009 (2)	0.016 (2)	0.013 (2)	−0.0028 (19)	0.0017 (17)	−0.0012 (19)
C5	0.011 (2)	0.011 (2)	0.015 (2)	0.0039 (18)	0.0056 (17)	0.0016 (18)
C6	0.0084 (16)	0.0156 (17)	0.0147 (16)	−0.0025 (13)	0.0041 (13)	0.0043 (14)
C7	0.017 (2)	0.019 (3)	0.021 (2)	0.001 (2)	0.0044 (19)	0.006 (2)
C8	0.010 (2)	0.014 (2)	0.015 (2)	−0.0001 (18)	0.0035 (17)	0.0013 (19)
C9	0.011 (2)	0.014 (2)	0.018 (2)	−0.0019 (19)	0.0017 (18)	0.003 (2)
C10	0.009 (2)	0.023 (3)	0.017 (2)	0.0013 (19)	0.0024 (18)	0.002 (2)
C11	0.026 (3)	0.027 (3)	0.013 (2)	0.005 (2)	0.0081 (19)	0.003 (2)
C12	0.021 (3)	0.026 (3)	0.024 (3)	0.004 (2)	−0.002 (2)	0.008 (2)
C13	0.017 (2)	0.021 (3)	0.022 (2)	0.005 (2)	0.0017 (19)	0.003 (2)
C14	0.013 (2)	0.019 (3)	0.016 (2)	−0.0003 (19)	0.0025 (18)	0.003 (2)
C15	0.010 (2)	0.016 (2)	0.018 (2)	−0.0030 (19)	0.0030 (18)	0.0004 (19)
C16	0.011 (2)	0.017 (3)	0.016 (2)	−0.0026 (19)	0.0025 (18)	0.006 (2)

Geometric parameters (Å, º) top

S1—C1	1.699 (4)	C6—C8	1.423 (5)
S1—C4	1.718 (4)	C6—C7	1.489 (5)
O1—C5	1.232 (4)	C7—H7A	0.9800
O2—C9	1.374 (4)	C7—H7B	0.9800
O2—C10	1.382 (5)	C7—H7C	0.9800
O3—C9	1.223 (4)	C8—C16	1.441 (5)
O4—C16	1.268 (4)	C8—C9	1.454 (5)
N1—C5	1.373 (5)	C10—C11	1.380 (5)
N1—N2	1.395 (4)	C10—C15	1.390 (5)
N1—H1N	0.92 (4)	C11—C12	1.380 (6)
N2—C6	1.315 (5)	C11—H11	0.9500
N2—H2N	1.00 (4)	C12—C13	1.402 (5)
C1—C2	1.352 (5)	C12—H12	0.9500
C1—H1	0.9500	C13—C14	1.376 (5)
C2—C3	1.417 (5)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.387 (5)
C3—C4	1.374 (5)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.465 (5)
C4—C5	1.455 (5)

C1—S1—C4	91.6 (2)	H7A—C7—H7C	109.5
C9—O2—C10	122.5 (3)	H7B—C7—H7C	109.5
C5—N1—N2	115.1 (3)	C6—C8—C16	120.1 (3)
C5—N1—H1N	123 (3)	C6—C8—C9	120.1 (4)
N2—N1—H1N	113 (3)	C16—C8—C9	119.8 (4)
C6—N2—N1	123.0 (4)	O3—C9—O2	115.1 (3)
C6—N2—H2N	117 (2)	O3—C9—C8	126.4 (4)
N1—N2—H2N	120 (2)	O2—C9—C8	118.5 (4)
C2—C1—S1	112.6 (3)	C11—C10—O2	116.8 (4)
C2—C1—H1	123.7	C11—C10—C15	121.3 (4)
S1—C1—H1	123.7	O2—C10—C15	121.9 (4)
C1—C2—C3	112.5 (4)	C12—C11—C10	118.9 (4)
C1—C2—H2	123.7	C12—C11—H11	120.5
C3—C2—H2	123.7	C10—C11—H11	120.5
C4—C3—C2	112.0 (4)	C11—C12—C13	121.2 (4)
C4—C3—H3	124.0	C11—C12—H12	119.4
C2—C3—H3	124.0	C13—C12—H12	119.4
C3—C4—C5	128.9 (4)	C14—C13—C12	118.4 (4)
C3—C4—S1	111.3 (3)	C14—C13—H13	120.8
C5—C4—S1	119.6 (3)	C12—C13—H13	120.8
O1—C5—N1	121.0 (3)	C13—C14—C15	121.5 (4)
O1—C5—C4	124.1 (3)	C13—C14—H14	119.2
N1—C5—C4	114.9 (3)	C15—C14—H14	119.2
N2—C6—C8	116.7 (4)	C14—C15—C10	118.6 (4)
N2—C6—C7	118.5 (4)	C14—C15—C16	122.5 (4)
C8—C6—C7	124.7 (4)	C10—C15—C16	118.8 (4)
C6—C7—H7A	109.5	O4—C16—C8	123.1 (4)
C6—C7—H7B	109.5	O4—C16—C15	118.6 (4)
H7A—C7—H7B	109.5	C8—C16—C15	118.2 (4)
C6—C7—H7C	109.5

C5—N1—N2—C6	−153.1 (4)	C6—C8—C9—O2	175.9 (3)
C4—S1—C1—C2	−1.1 (3)	C16—C8—C9—O2	−4.3 (5)
S1—C1—C2—C3	1.3 (5)	C9—O2—C10—C11	176.6 (4)
C1—C2—C3—C4	−0.9 (5)	C9—O2—C10—C15	−3.5 (5)
C2—C3—C4—C5	−175.5 (4)	O2—C10—C11—C12	179.0 (3)
C2—C3—C4—S1	0.0 (5)	C15—C10—C11—C12	−1.0 (6)
C1—S1—C4—C3	0.6 (3)	C10—C11—C12—C13	−0.2 (6)
C1—S1—C4—C5	176.6 (3)	C11—C12—C13—C14	0.5 (6)
N2—N1—C5—O1	8.1 (5)	C12—C13—C14—C15	0.4 (6)
N2—N1—C5—C4	−174.8 (3)	C13—C14—C15—C10	−1.5 (6)
C3—C4—C5—O1	148.8 (4)	C13—C14—C15—C16	−178.2 (4)
S1—C4—C5—O1	−26.4 (6)	C11—C10—C15—C14	1.8 (6)
C3—C4—C5—N1	−28.2 (6)	O2—C10—C15—C14	−178.1 (3)
S1—C4—C5—N1	156.6 (3)	C11—C10—C15—C16	178.7 (4)
N1—N2—C6—C8	179.3 (3)	O2—C10—C15—C16	−1.3 (6)
N1—N2—C6—C7	1.2 (6)	C6—C8—C16—O4	−1.3 (6)
N2—C6—C8—C16	−3.4 (5)	C9—C8—C16—O4	178.9 (4)
C7—C6—C8—C16	174.5 (4)	C6—C8—C16—C15	179.6 (3)
N2—C6—C8—C9	176.4 (3)	C9—C8—C16—C15	−0.2 (5)
C7—C6—C8—C9	−5.7 (6)	C14—C15—C16—O4	0.5 (6)
C10—O2—C9—O3	−174.9 (3)	C10—C15—C16—O4	−176.2 (3)
C10—O2—C9—C8	6.2 (5)	C14—C15—C16—C8	179.7 (4)
C6—C8—C9—O3	−2.9 (6)	C10—C15—C16—C8	3.0 (5)
C16—C8—C9—O3	176.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O4	1.00 (4)	1.64 (5)	2.481 (4)	140 (4)
N1—H1N···O1ⁱ	0.92 (4)	1.93 (4)	2.841 (4)	177 (4)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₂O₄S
M_r	328.34
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	4.8631 (11), 11.833 (3), 13.296 (3)
α, β, γ (°)	107.106 (5), 100.376 (4), 97.553 (4)
V (Å³)	705.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.55 × 0.15 × 0.08

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3526, 2441, 1403
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.116, 0.87
No. of reflections	2441
No. of parameters	217
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.36

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2002), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O4	1.00 (4)	1.64 (5)	2.481 (4)	140 (4)
N1—H1N···O1ⁱ	0.92 (4)	1.93 (4)	2.841 (4)	177 (4)

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors thank Royal Society of Chemistry for financial support of this work.

References

Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2002). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kotali, A. (2009). Arkivoc, i, 81–96. CrossRef Google Scholar
Kotali, A., Kotali, E., Lafazanis, I. S. & Harris, P. A. (2010). Curr. Org. Synth. 7, 62–77. CrossRef CAS 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

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Volume 67| Part 4| April 2011| Page o1014

doi:10.1107/S1600536811010907

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

N′-[1-(2,4-Dioxo-3,4-di­hydro-2H-1-benzo­pyran-3-yl­­idene)eth­yl]thiophene-2-carbo­hydrazide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-[1-(2,4-Dioxo-3,4-dihydro-2H-1-benzopyran-3-ylidene)ethyl]thiophene-2-carbohydrazide