(E)-N′-(4-Methoxy­benzyl­idene)thio­phene-2-carbohydrazide

Abstract

In the title compound, C₁₃H₁₂N₂O₂S, the dihedral angle between the aromatic rings is 15.20 (11)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R ₂ ²(8) loops.

Related literature

For a related structure, see: Li & Jian (2010 ▶).

Experimental

Crystal data

• C₁₃H₁₂N₂O₂S

• M _r = 260.31

• Monoclinic,

• a = 16.106 (3) Å

• b = 5.3292 (11) Å

• c = 14.812 (3) Å

• β = 104.91 (3)°

• V = 1228.5 (4) ų

• Z = 4

• Mo Kα radiation

• μ = 0.26 mm⁻¹

• T = 293 K

• 0.25 × 0.22 × 0.18 mm

Data collection

• Bruker SMART CCD diffractometer

• 11253 measured reflections

• 2807 independent reflections

• 2454 reflections with I > 2σ(I)

• R _int = 0.027

Refinement

• R[F ² > 2σ(F ²)] = 0.056

• wR(F ²) = 0.177

• S = 1.00

• 2807 reflections

• 163 parameters

• H-atom parameters constrained

• Δρ_max = 0.74 e Å⁻³

• Δρ_min = −0.53 e Å⁻³

Data collection: SMART (Bruker 1997 ▶); cell refinement: SAINT (Bruker 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.12	2.963 (2)	167

Symmetry code: (i) .

supplementary crystallographic information

Experimental

A mixture of thiophene-2-carbohydrazide (0.10 mol), and 4-methoxybenzaldehyde (0.10 mol) was stirred in refluxing ethanol (10 ml) for 4 h to afford the title compound (0.079 mol, yield 79%). Colourless blocks of (I) were obtained by recrystallization from ethanol at room temperature.

Refinement

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances = 0.93-0.97 Å; N—H = 0.86Å and with U_iso(H) = 1.2U_eq(C,N) or 1.5U_eq(C_methyl).

Figures

Fig. 1.

The structure of (I) showing 30% probability displacement ellipsoids.

Crystal data

C13H12N2O2S	F(000) = 544
Mr = 260.31	Dx = 1.407 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2454 reflections
a = 16.106 (3) Å	θ = 2.7–25.3°
b = 5.3292 (11) Å	µ = 0.26 mm−1
c = 14.812 (3) Å	T = 293 K
β = 104.91 (3)°	Block, colorless
V = 1228.5 (4) Å3	0.25 × 0.22 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	2454 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
graphite	θmax = 27.5°, θmin = 3.3°
phi and ω scans	h = −20→20
11253 measured reflections	k = −6→6
2807 independent reflections	l = −19→18

Refinement

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1142P)2 + 0.7797P] where P = (Fo2 + 2Fc2)/3
2807 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.53 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.19516 (4)	0.31168 (11)	0.98996 (4)	0.0456 (2)
N2	0.17079 (11)	0.7123 (3)	1.09840 (12)	0.0364 (4)
N1	0.09320 (10)	0.7857 (3)	1.04270 (12)	0.0372 (4)
H1A	0.0643	0.9002	1.0620	0.045*
O2	−0.00677 (9)	0.7645 (3)	0.90675 (11)	0.0437 (4)
C9	0.06111 (12)	0.6815 (4)	0.95773 (14)	0.0347 (4)
C8	0.19896 (13)	0.8393 (4)	1.17289 (15)	0.0381 (4)
H8A	0.1659	0.9700	1.1865	0.046*
C5	0.28237 (13)	0.7838 (4)	1.23759 (14)	0.0366 (4)
O1	0.52295 (11)	0.6947 (4)	1.42184 (13)	0.0608 (5)
C11	0.07350 (14)	0.3690 (4)	0.83349 (18)	0.0449 (5)
H11A	0.0269	0.4297	0.7878	0.054*
C10	0.10555 (11)	0.4692 (4)	0.92598 (13)	0.0344 (4)
C2	0.44404 (14)	0.7112 (4)	1.35954 (15)	0.0428 (5)
C3	0.41450 (15)	0.5483 (5)	1.28526 (16)	0.0480 (5)
H3A	0.4485	0.4149	1.2758	0.058*
C6	0.31271 (15)	0.9418 (5)	1.31370 (16)	0.0473 (5)
H6A	0.2785	1.0739	1.3239	0.057*
C7	0.39260 (16)	0.9065 (5)	1.37430 (17)	0.0520 (6)
H7A	0.4118	1.0136	1.4249	0.062*
C4	0.33415 (15)	0.5854 (4)	1.22531 (16)	0.0454 (5)
H4A	0.3144	0.4752	1.1757	0.054*
C13	0.19081 (14)	0.1074 (4)	0.90128 (16)	0.0447 (5)
H13A	0.2289	−0.0259	0.9053	0.054*
C12	0.12683 (14)	0.1562 (5)	0.82410 (17)	0.0457 (5)
H12A	0.1178	0.0615	0.7697	0.055*
C1	0.57849 (17)	0.5001 (7)	1.4092 (2)	0.0675 (8)
H1B	0.6315	0.5105	1.4569	0.101*
H1C	0.5898	0.5168	1.3489	0.101*
H1D	0.5518	0.3407	1.4131	0.101*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
S1	0.0484 (4)	0.0437 (4)	0.0437 (3)	0.0088 (2)	0.0098 (2)	0.0038 (2)
N2	0.0340 (8)	0.0363 (9)	0.0375 (9)	0.0022 (6)	0.0069 (7)	0.0034 (7)
N1	0.0319 (8)	0.0382 (9)	0.0407 (9)	0.0047 (6)	0.0079 (7)	0.0012 (7)
O2	0.0310 (7)	0.0480 (9)	0.0477 (9)	0.0055 (6)	0.0019 (6)	0.0001 (7)
C9	0.0301 (9)	0.0343 (10)	0.0404 (10)	−0.0017 (7)	0.0103 (7)	0.0048 (7)
C8	0.0390 (10)	0.0389 (10)	0.0375 (10)	0.0040 (8)	0.0122 (8)	0.0011 (8)
C5	0.0389 (10)	0.0369 (10)	0.0343 (10)	0.0005 (8)	0.0099 (8)	0.0016 (7)
O1	0.0453 (9)	0.0744 (13)	0.0518 (10)	0.0062 (8)	−0.0072 (7)	−0.0129 (9)
C11	0.0408 (11)	0.0411 (11)	0.0596 (13)	−0.0091 (9)	0.0253 (10)	−0.0152 (10)
C10	0.0287 (8)	0.0361 (10)	0.0380 (9)	−0.0016 (7)	0.0079 (7)	0.0030 (8)
C2	0.0385 (10)	0.0487 (12)	0.0376 (10)	−0.0005 (9)	0.0033 (8)	−0.0016 (9)
C3	0.0462 (12)	0.0447 (12)	0.0479 (12)	0.0092 (9)	0.0030 (9)	−0.0065 (10)
C6	0.0508 (12)	0.0478 (12)	0.0417 (11)	0.0087 (10)	0.0091 (9)	−0.0097 (9)
C7	0.0542 (13)	0.0543 (14)	0.0423 (11)	0.0024 (11)	0.0029 (10)	−0.0153 (10)
C4	0.0477 (11)	0.0401 (11)	0.0422 (11)	0.0043 (9)	0.0005 (9)	−0.0084 (9)
C13	0.0442 (11)	0.0382 (11)	0.0525 (12)	0.0007 (9)	0.0142 (9)	−0.0021 (9)
C12	0.0386 (11)	0.0480 (12)	0.0505 (12)	−0.0069 (9)	0.0116 (9)	−0.0118 (10)
C1	0.0423 (13)	0.086 (2)	0.0669 (17)	0.0125 (13)	0.0002 (11)	−0.0018 (15)

Geometric parameters (Å, °)

S1—C13	1.694 (2)	C11—H11A	0.9300
S1—C10	1.727 (2)	C2—C7	1.382 (3)
N2—C8	1.274 (3)	C2—C3	1.386 (3)
N2—N1	1.366 (2)	C3—C4	1.382 (3)
N1—C9	1.351 (3)	C3—H3A	0.9300
N1—H1A	0.8600	C6—C7	1.379 (3)
O2—C9	1.239 (2)	C6—H6A	0.9300
C9—C10	1.479 (3)	C7—H7A	0.9300
C8—C5	1.466 (3)	C4—H4A	0.9300
C8—H8A	0.9300	C13—C12	1.353 (3)
C5—C4	1.387 (3)	C13—H13A	0.9300
C5—C6	1.391 (3)	C12—H12A	0.9300
O1—C2	1.368 (3)	C1—H1B	0.9600
O1—C1	1.413 (3)	C1—H1C	0.9600
C11—C10	1.437 (3)	C1—H1D	0.9600
C11—C12	1.451 (3)
C13—S1—C10	91.43 (11)	C4—C3—C2	119.6 (2)
C8—N2—N1	115.96 (18)	C4—C3—H3A	120.2
C9—N1—N2	121.10 (17)	C2—C3—H3A	120.2
C9—N1—H1A	119.4	C7—C6—C5	121.3 (2)
N2—N1—H1A	119.4	C7—C6—H6A	119.4
O2—C9—N1	119.15 (19)	C5—C6—H6A	119.4
O2—C9—C10	120.17 (19)	C6—C7—C2	119.8 (2)
N1—C9—C10	120.68 (17)	C6—C7—H7A	120.1
N2—C8—C5	121.42 (19)	C2—C7—H7A	120.1
N2—C8—H8A	119.3	C3—C4—C5	121.3 (2)
C5—C8—H8A	119.3	C3—C4—H4A	119.3
C4—C5—C6	118.0 (2)	C5—C4—H4A	119.3
C4—C5—C8	123.29 (19)	C12—C13—S1	113.72 (18)
C6—C5—C8	118.65 (19)	C12—C13—H13A	123.1
C2—O1—C1	117.9 (2)	S1—C13—H13A	123.1
C10—C11—C12	107.8 (2)	C13—C12—C11	114.2 (2)
C10—C11—H11A	126.1	C13—C12—H12A	122.9
C12—C11—H11A	126.1	C11—C12—H12A	122.9
C11—C10—C9	120.20 (18)	O1—C1—H1B	109.5
C11—C10—S1	112.76 (16)	O1—C1—H1C	109.5
C9—C10—S1	127.02 (15)	H1B—C1—H1C	109.5
O1—C2—C7	115.6 (2)	O1—C1—H1D	109.5
O1—C2—C3	124.4 (2)	H1B—C1—H1D	109.5
C7—C2—C3	120.0 (2)	H1C—C1—H1D	109.5

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.12	2.963 (2)	167

Symmetry codes: (i) −x, −y+2, −z+2.