N-{(Z)-3-Oxo-3-[(E)-(pyridin-2-ylmeth­yl)diazen­yl]-1-(thio­phen-2-yl)prop-1-en-2-yl}benzamide

Sharma, D.K.; Subbulakshmi, K.N.; Narayana, B.; Sarojini, B.K.; Anthal, S.; Kant, R.

doi:10.1107/S2414314616012761

organic compounds

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ISSN: 2414-3146

Volume 1| Part 8| August 2016| x161276

doi:10.1107/S2414314616012761

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N-{(Z)-3-Oxo-3-[(E)-(pyridin-2-ylmethyl)diazenyl]-1-(thiophen-2-yl)prop-1-en-2-yl}benzamide

Devinder K. Sharma,^a K. N. Subbulakshmi,^b B. Narayana,^b B. K. Sarojini,^c Sumati Anthal ^a and Rajni Kant ^a ^*

^aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, ^bDepartment of Chemistry, Mangalore University, Mangalagangothri 574 199, Mangalore, India, and ^cDepartment of Studies in Chemistry–Industrial Chemistry, Mangalore University, Mangalagangothri 574 199, India
^*Correspondence e-mail: rkant.ju@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 28 July 2016; accepted 8 August 2016; online 12 August 2016)

In the title compound, C₂₀H₁₆N₄O₂S, the thiophene ring subtends dihedral angles of 58.6 (3) and 9.8 (3)° with the benzamide and pyridine rings, respectively, whereas these two rings are inclined to one another by 59.3 (3)°. There is an intramolecular C—H⋯π interaction present involving the pyridine and benzamide rings. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming chains along the [010] direction. The chains are linked by C—H⋯S hydrogen bonds and C—H⋯π interactions, forming sheets parallel to the ab plane.

Keywords: crystal structure; diazo; benzamide; hydrogen bonding; C—H⋯π interactions.

CCDC reference: 1498199

Structure description

Azo compounds have a (–N=N–) linkage, and are highly coloured compounds. They are used as dyes and pigments for colouring fibers, optical storage devices, photo-electronic applications, printing systems, textile dyes etc (Wang et al., 2000 ). The title compound is initially a hydrazone formed by the reaction of the precursor hydrazide 1 with pyridine 2-aldehyde (see Scheme). However, it rearranges to a diazo derivative by a 1,3 proton shift. Herein, we report on the crystal structure of compound 2, containing a diazo (–N=N–) linkage.

In the title compound, Fig. 1, the thiophene ring forms a dihedral angle 9.8 (3)° with the pyridine ring. The benzamide ring is inclined to the thiophene and pyridine rings by 58.6 (3) and 59.3 (3)°, respectively. The molecule has an E conformation about the N1=N2 bond, and a Z conformation about the C5=C6 bond. There is an intramolecular C—H⋯π interaction present involving the pyridine and benzamide rings (Fig. 1 and Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of rings N3/C9–C13 and C15–C20, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O1ⁱ	0.86	2.18	2.931 (6)	145
C8—H8B⋯S1ⁱⁱ	0.97	2.68	3.492 (5)	141
C10—H10⋯Cg3	0.93	2.89	3.627 (6)	137
C12—H12⋯Cg2ⁱⁱ	0.93	2.92	3.648 (6)	136
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+2]$ ; (ii) x+1, y, z.

Figure 1
A view of the molecular structure of the title compound 2, showing the atom labelling. Displacement ellipsoids are drawn at the 40% probability level. The intramolecular C—H⋯π interaction is shown as a blue dashed arrow (see Table 1

In the crystal, molecules are linked by N—H⋯O hydrogen bonds forming chains along the b-axis direction (Fig. 2 and Table 1). The chains are linked by C—H⋯S hydrogen bonds and C—H⋯π interactions, forming sheets parallel to the ab plane (Fig. 2 and Table 1).

Figure 2
The crystal packing of the title compound 2, viewed along the a axis. The N—H⋯O and C—H⋯S hydrogen bonds are shown as dashed lines (see Table 1

). For clarity, only the H atoms involved in the various intra- and intermolecular interactions have been included.

Synthesis and crystallization

A mixture of [3-hydrazinyl-3-oxo-1-(thiophen-2-yl)prop-1-en-2-yl]benzamide 1 (2.87 g, 0.01 mol), and pyridine-2-carbaldehyde (1.07 g, 0.01 mol) in 20 ml ethanol were stirred for 3–4 h. The solid obtained was filtered, washed with cold water, dried and recrystallized from ethanol. Single crystals of 2 were grown from a methanol–1,4-dioxane (1:1) mixture by slow evaporation (m.p. 507–508 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₁₆N₄O₂S
M_r	376.43
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	9.3289 (10), 9.9031 (10), 9.8984 (12)
β (°)	97.221 (11)
V (Å³)	907.21 (17)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ )
T_min, T_max	0.749, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3602, 2547, 1807
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.137, 0.98
No. of reflections	2547
No. of parameters	244
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.27
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ), SHELXS97 and SHELXL97 (Sheldrick, 2008 ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1498199

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S2414314616012761/su4067sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616012761/su4067Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616012761/su4067Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

N-{(Z)-3-Oxo-3-[(E)-(pyridin-2-ylmethyl)diazenyl]-1-(thiophen-2-yl)prop-1-en-2-yl}benzamide top

Crystal data top

C₂₀H₁₆N₄O₂S	F(000) = 392
M_r = 376.43	D_x = 1.378 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 985 reflections
a = 9.3289 (10) Å	θ = 4.4–26.3°
b = 9.9031 (10) Å	µ = 0.20 mm⁻¹
c = 9.8984 (12) Å	T = 293 K
β = 97.221 (11)°	Rectangular, brown
V = 907.21 (17) Å³	0.30 × 0.20 × 0.20 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2547 independent reflections
Radiation source: fine-focus sealed tube	1807 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.5°
ω scans	h = −9→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −6→12
T_min = 0.749, T_max = 1.000	l = −11→12
3602 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0485P)²] where P = (F_o² + 2F_c²)/3
2547 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.27 e Å⁻³

Special details top

Experimental. CrysAlis Pro (Oxford Diffraction, 2010)

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 > 2sigma(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	0.53359 (14)	0.16714 (15)	1.01498 (14)	0.0554 (4)
N1	1.0902 (4)	0.3655 (4)	1.0744 (4)	0.0444 (10)
N4	0.8437 (4)	0.2341 (4)	1.1093 (4)	0.0397 (9)
H4	0.8568	0.1485	1.1021	0.048*
O2	0.7951 (5)	0.4099 (3)	1.2397 (4)	0.0637 (11)
O1	0.9821 (4)	0.4880 (4)	0.8927 (4)	0.0664 (11)
N2	1.2188 (5)	0.4370 (4)	1.0774 (4)	0.0493 (11)
N3	1.2102 (4)	0.2226 (4)	1.2834 (4)	0.0473 (11)
C9	1.3313 (5)	0.2957 (5)	1.2705 (5)	0.0446 (12)
C8	1.3214 (5)	0.4001 (5)	1.1653 (5)	0.0484 (13)
H8A	1.3509	0.4822	1.2145	0.058*
H8B	1.3993	0.3788	1.1125	0.058*
C4	0.5869 (5)	0.2766 (5)	0.8944 (5)	0.0470 (12)
C15	0.8350 (5)	0.1983 (5)	1.3518 (5)	0.0401 (11)
C14	0.8217 (5)	0.2889 (5)	1.2308 (5)	0.0425 (12)
C7	0.9768 (5)	0.3999 (5)	0.9807 (5)	0.0421 (12)
C16	0.8130 (5)	0.0601 (5)	1.3426 (5)	0.0464 (12)
H16	0.7867	0.0198	1.2583	0.056*
C5	0.7281 (6)	0.3345 (5)	0.8987 (5)	0.0499 (13)
H5	0.7413	0.3901	0.8256	0.060*
C6	0.8447 (5)	0.3205 (5)	0.9930 (5)	0.0408 (11)
C20	0.8724 (5)	0.2558 (6)	1.4772 (5)	0.0500 (13)
H20	0.8837	0.3489	1.4842	0.060*
C11	1.3428 (6)	0.1005 (6)	1.4664 (6)	0.0637 (16)
H11	1.3449	0.0342	1.5332	0.076*
C13	1.4587 (6)	0.2743 (6)	1.3537 (6)	0.0564 (14)
H13	1.5398	0.3260	1.3436	0.068*
C17	0.8305 (6)	−0.0174 (6)	1.4596 (6)	0.0602 (15)
H17	0.8129	−0.1098	1.4541	0.072*
C1	0.3663 (6)	0.1528 (6)	0.9289 (6)	0.0634 (16)
H1	0.2947	0.0985	0.9578	0.076*
C3	0.4727 (6)	0.3004 (6)	0.7921 (6)	0.0612 (15)
H3	0.4781	0.3572	0.7180	0.073*
C10	1.2185 (6)	0.1270 (5)	1.3791 (6)	0.0559 (15)
H10	1.1365	0.0757	1.3875	0.067*
C19	0.8932 (5)	0.1783 (7)	1.5915 (5)	0.0640 (16)
H19	0.9211	0.2184	1.6757	0.077*
C18	0.8731 (6)	0.0402 (6)	1.5827 (6)	0.0633 (16)
H18	0.8887	−0.0130	1.6605	0.076*
C12	1.4648 (6)	0.1767 (8)	1.4506 (6)	0.0671 (16)
H12	1.5508	0.1608	1.5067	0.081*
C2	0.3467 (6)	0.2271 (7)	0.8149 (7)	0.0764 (19)
H2	0.2602	0.2304	0.7570	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0574 (8)	0.0551 (8)	0.0545 (8)	−0.0009 (7)	0.0105 (7)	0.0024 (7)
N1	0.040 (2)	0.045 (2)	0.048 (3)	−0.004 (2)	0.0056 (19)	0.003 (2)
N4	0.049 (2)	0.035 (2)	0.036 (2)	0.0003 (18)	0.0091 (19)	0.0022 (18)
O2	0.102 (3)	0.0386 (19)	0.051 (2)	0.020 (2)	0.012 (2)	0.0004 (19)
O1	0.063 (2)	0.068 (3)	0.066 (3)	−0.020 (2)	0.002 (2)	0.028 (2)
N2	0.048 (3)	0.046 (3)	0.055 (3)	−0.005 (2)	0.012 (2)	0.008 (2)
N3	0.045 (2)	0.046 (2)	0.050 (3)	0.003 (2)	0.004 (2)	0.006 (2)
C9	0.043 (3)	0.049 (3)	0.043 (3)	−0.003 (2)	0.012 (2)	0.000 (3)
C8	0.044 (3)	0.053 (3)	0.050 (3)	0.002 (2)	0.014 (3)	0.005 (3)
C4	0.051 (3)	0.050 (3)	0.040 (3)	−0.004 (3)	0.003 (2)	−0.001 (2)
C15	0.037 (2)	0.046 (3)	0.040 (3)	0.003 (2)	0.011 (2)	0.009 (2)
C14	0.044 (3)	0.039 (3)	0.044 (3)	−0.001 (2)	0.002 (2)	0.004 (2)
C7	0.043 (3)	0.042 (3)	0.042 (3)	−0.007 (2)	0.008 (2)	0.007 (2)
C16	0.047 (3)	0.044 (3)	0.048 (3)	0.001 (2)	0.007 (2)	0.006 (3)
C5	0.060 (3)	0.050 (3)	0.039 (3)	0.000 (3)	0.006 (3)	−0.002 (3)
C6	0.050 (3)	0.041 (3)	0.032 (2)	0.002 (2)	0.007 (2)	0.005 (2)
C20	0.052 (3)	0.056 (3)	0.043 (3)	0.000 (3)	0.006 (2)	0.002 (3)
C11	0.060 (4)	0.068 (4)	0.061 (4)	0.008 (3)	0.002 (3)	0.016 (3)
C13	0.043 (3)	0.073 (4)	0.052 (3)	0.004 (3)	0.000 (3)	0.000 (3)
C17	0.057 (3)	0.062 (4)	0.062 (4)	−0.005 (3)	0.011 (3)	0.026 (3)
C1	0.058 (3)	0.060 (4)	0.072 (4)	−0.009 (3)	0.007 (3)	−0.005 (4)
C3	0.055 (3)	0.066 (4)	0.059 (4)	−0.005 (3)	−0.006 (3)	0.006 (3)
C10	0.057 (3)	0.048 (3)	0.064 (4)	−0.001 (3)	0.011 (3)	0.010 (3)
C19	0.063 (3)	0.094 (5)	0.036 (3)	−0.005 (4)	0.008 (3)	−0.006 (3)
C18	0.063 (4)	0.069 (4)	0.059 (4)	0.001 (3)	0.011 (3)	0.031 (3)
C12	0.047 (3)	0.086 (4)	0.066 (4)	0.014 (4)	−0.006 (3)	0.001 (4)
C2	0.059 (4)	0.090 (5)	0.074 (4)	−0.007 (4)	−0.015 (3)	−0.001 (4)

Geometric parameters (Å, º) top

S1—C1	1.687 (5)	C16—H16	0.9300
S1—C4	1.731 (5)	C5—C6	1.349 (7)
N1—C7	1.359 (7)	C5—H5	0.9300
N1—N2	1.389 (5)	C20—C19	1.361 (7)
N4—C14	1.359 (6)	C20—H20	0.9300
N4—C6	1.436 (6)	C11—C10	1.382 (7)
N4—H4	0.8600	C11—C12	1.390 (8)
O2—C14	1.229 (5)	C11—H11	0.9300
O1—C7	1.238 (6)	C13—C12	1.358 (8)
N2—C8	1.264 (6)	C13—H13	0.9300
N3—C10	1.335 (6)	C17—C18	1.358 (8)
N3—C9	1.362 (6)	C17—H17	0.9300
C9—C13	1.374 (6)	C1—C2	1.341 (8)
C9—C8	1.462 (6)	C1—H1	0.9300
C8—H8A	0.9700	C3—C2	1.423 (8)
C8—H8B	0.9700	C3—H3	0.9300
C4—C3	1.395 (7)	C10—H10	0.9300
C4—C5	1.432 (7)	C19—C18	1.382 (9)
C15—C20	1.370 (6)	C19—H19	0.9300
C15—C16	1.385 (7)	C18—H18	0.9300
C15—C14	1.490 (6)	C12—H12	0.9300
C7—C6	1.479 (7)	C2—H2	0.9300
C16—C17	1.382 (7)

C1—S1—C4	91.9 (3)	C5—C6—C7	119.8 (5)
C7—N1—N2	118.9 (4)	N4—C6—C7	118.2 (4)
C14—N4—C6	119.2 (4)	C19—C20—C15	120.8 (5)
C14—N4—H4	120.4	C19—C20—H20	119.6
C6—N4—H4	120.4	C15—C20—H20	119.6
C8—N2—N1	116.4 (4)	C10—C11—C12	117.4 (5)
C10—N3—C9	118.0 (4)	C10—C11—H11	121.3
N3—C9—C13	121.8 (5)	C12—C11—H11	121.3
N3—C9—C8	117.6 (4)	C12—C13—C9	119.3 (5)
C13—C9—C8	120.6 (5)	C12—C13—H13	120.4
N2—C8—C9	132.0 (5)	C9—C13—H13	120.4
N2—C8—H8A	104.2	C18—C17—C16	120.6 (5)
C9—C8—H8A	104.2	C18—C17—H17	119.7
N2—C8—H8B	104.2	C16—C17—H17	119.7
C9—C8—H8B	104.2	C2—C1—S1	113.5 (5)
H8A—C8—H8B	105.5	C2—C1—H1	123.3
C3—C4—C5	124.7 (5)	S1—C1—H1	123.3
C3—C4—S1	110.3 (4)	C4—C3—C2	111.7 (6)
C5—C4—S1	125.0 (4)	C4—C3—H3	124.2
C20—C15—C16	119.3 (5)	C2—C3—H3	124.2
C20—C15—C14	117.6 (4)	N3—C10—C11	123.2 (5)
C16—C15—C14	123.1 (4)	N3—C10—H10	118.4
O2—C14—N4	120.5 (4)	C11—C10—H10	118.4
O2—C14—C15	121.8 (5)	C20—C19—C18	120.1 (5)
N4—C14—C15	117.7 (4)	C20—C19—H19	120.0
O1—C7—N1	124.0 (4)	C18—C19—H19	120.0
O1—C7—C6	122.6 (5)	C17—C18—C19	119.6 (5)
N1—C7—C6	113.3 (4)	C17—C18—H18	120.2
C17—C16—C15	119.5 (5)	C19—C18—H18	120.2
C17—C16—H16	120.2	C13—C12—C11	120.2 (5)
C15—C16—H16	120.2	C13—C12—H12	119.9
C6—C5—C4	129.7 (5)	C11—C12—H12	119.9
C6—C5—H5	115.2	C1—C2—C3	112.7 (5)
C4—C5—H5	115.2	C1—C2—H2	123.7
C5—C6—N4	122.0 (5)	C3—C2—H2	123.7

C7—N1—N2—C8	−179.2 (5)	C14—N4—C6—C7	78.7 (5)
C10—N3—C9—C13	−0.8 (7)	O1—C7—C6—C5	6.0 (8)
C10—N3—C9—C8	179.9 (4)	N1—C7—C6—C5	−173.6 (4)
N1—N2—C8—C9	−1.9 (8)	O1—C7—C6—N4	−171.7 (5)
N3—C9—C8—N2	−1.5 (8)	N1—C7—C6—N4	8.7 (6)
C13—C9—C8—N2	179.2 (5)	C16—C15—C20—C19	2.4 (8)
C1—S1—C4—C3	0.9 (4)	C14—C15—C20—C19	−176.8 (5)
C1—S1—C4—C5	−179.0 (5)	N3—C9—C13—C12	0.6 (8)
C6—N4—C14—O2	4.0 (7)	C8—C9—C13—C12	179.9 (5)
C6—N4—C14—C15	−174.4 (4)	C15—C16—C17—C18	−2.0 (8)
C20—C15—C14—O2	−24.7 (7)	C4—S1—C1—C2	−0.8 (5)
C16—C15—C14—O2	156.1 (5)	C5—C4—C3—C2	179.1 (5)
C20—C15—C14—N4	153.6 (4)	S1—C4—C3—C2	−0.8 (6)
C16—C15—C14—N4	−25.6 (7)	C9—N3—C10—C11	1.0 (7)
N2—N1—C7—O1	3.3 (8)	C12—C11—C10—N3	−1.1 (9)
N2—N1—C7—C6	−177.1 (4)	C15—C20—C19—C18	−1.7 (9)
C20—C15—C16—C17	−0.6 (7)	C16—C17—C18—C19	2.7 (9)
C14—C15—C16—C17	178.6 (5)	C20—C19—C18—C17	−0.9 (9)
C3—C4—C5—C6	178.8 (5)	C9—C13—C12—C11	−0.7 (9)
S1—C4—C5—C6	−1.3 (8)	C10—C11—C12—C13	0.9 (9)
C4—C5—C6—N4	2.4 (8)	S1—C1—C2—C3	0.5 (7)
C4—C5—C6—C7	−175.1 (5)	C4—C3—C2—C1	0.2 (8)
C14—N4—C6—C5	−98.9 (5)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of rings N3/C9–C13 and C15–C20, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1ⁱ	0.86	2.18	2.931 (6)	145
C8—H8B···S1ⁱⁱ	0.97	2.68	3.492 (5)	141
C10—H10···Cg3	0.93	2.89	3.627 (6)	137
C12—H12···Cg2ⁱⁱ	0.93	2.92	3.648 (6)	136

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

Acknowledgements

RK acknowledges the Indian Council of Medical Research, New Delhi, for financial support [research project No. BIC/12 (14)/2012] and the Department of Science and Technology Research (project No. EMR/2014/000467). KNS gratefully acknowledges the Department of Chemistry, Shri Madhwa Vadiraja Institute of Technology, Bantakal (VTU Belgam), for providing research facilities.

References

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. 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
Wang, S., Shen, S. & Xu, H. (2000). Dyes Pigments, 44, 195–198. Web of Science CrossRef CAS Google Scholar

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Volume 1| Part 8| August 2016| x161276

doi:10.1107/S2414314616012761

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

N-{(Z)-3-Oxo-3-[(E)-(pyridin-2-ylmeth­yl)diazen­yl]-1-(thio­phen-2-yl)prop-1-en-2-yl}benzamide

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

N-{(Z)-3-Oxo-3-[(E)-(pyridin-2-ylmethyl)diazenyl]-1-(thiophen-2-yl)prop-1-en-2-yl}benzamide