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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1400.
Published online 2010 May 22. doi:  10.1107/S1600536810017836
PMCID: PMC2979446

(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 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1400-scheme1.jpg

Experimental

Crystal data

  • C13H12N2O2S
  • M r = 260.31
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1400-efi1.jpg
  • a = 16.106 (3) Å
  • b = 5.3292 (11) Å
  • c = 14.812 (3) Å
  • β = 104.91 (3)°
  • V = 1228.5 (4) Å3
  • 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
  • Δρmax = 0.74 e Å−3
  • Δρmin = −0.53 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017836/hb5449sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017836/hb5449Isup2.hkl

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

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 Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(Cmethyl).

Figures

Fig. 1.
The structure of (I) showing 30% probability displacement ellipsoids.

Crystal data

C13H12N2O2SF(000) = 544
Mr = 260.31Dx = 1.407 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2454 reflections
a = 16.106 (3) Åθ = 2.7–25.3°
b = 5.3292 (11) ŵ = 0.26 mm1
c = 14.812 (3) ÅT = 293 K
β = 104.91 (3)°Block, colorless
V = 1228.5 (4) Å30.25 × 0.22 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer2454 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
graphiteθmax = 27.5°, θmin = 3.3°
phi and ω scansh = −20→20
11253 measured reflectionsk = −6→6
2807 independent reflectionsl = −19→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.1142P)2 + 0.7797P] where P = (Fo2 + 2Fc2)/3
2807 reflections(Δ/σ)max = 0.001
163 parametersΔρmax = 0.74 e Å3
0 restraintsΔρmin = −0.53 e Å3

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 (Å2)

xyzUiso*/Ueq
S10.19516 (4)0.31168 (11)0.98996 (4)0.0456 (2)
N20.17079 (11)0.7123 (3)1.09840 (12)0.0364 (4)
N10.09320 (10)0.7857 (3)1.04270 (12)0.0372 (4)
H1A0.06430.90021.06200.045*
O2−0.00677 (9)0.7645 (3)0.90675 (11)0.0437 (4)
C90.06111 (12)0.6815 (4)0.95773 (14)0.0347 (4)
C80.19896 (13)0.8393 (4)1.17289 (15)0.0381 (4)
H8A0.16590.97001.18650.046*
C50.28237 (13)0.7838 (4)1.23759 (14)0.0366 (4)
O10.52295 (11)0.6947 (4)1.42184 (13)0.0608 (5)
C110.07350 (14)0.3690 (4)0.83349 (18)0.0449 (5)
H11A0.02690.42970.78780.054*
C100.10555 (11)0.4692 (4)0.92598 (13)0.0344 (4)
C20.44404 (14)0.7112 (4)1.35954 (15)0.0428 (5)
C30.41450 (15)0.5483 (5)1.28526 (16)0.0480 (5)
H3A0.44850.41491.27580.058*
C60.31271 (15)0.9418 (5)1.31370 (16)0.0473 (5)
H6A0.27851.07391.32390.057*
C70.39260 (16)0.9065 (5)1.37430 (17)0.0520 (6)
H7A0.41181.01361.42490.062*
C40.33415 (15)0.5854 (4)1.22531 (16)0.0454 (5)
H4A0.31440.47521.17570.054*
C130.19081 (14)0.1074 (4)0.90128 (16)0.0447 (5)
H13A0.2289−0.02590.90530.054*
C120.12683 (14)0.1562 (5)0.82410 (17)0.0457 (5)
H12A0.11780.06150.76970.055*
C10.57849 (17)0.5001 (7)1.4092 (2)0.0675 (8)
H1B0.63150.51051.45690.101*
H1C0.58980.51681.34890.101*
H1D0.55180.34071.41310.101*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0484 (4)0.0437 (4)0.0437 (3)0.0088 (2)0.0098 (2)0.0038 (2)
N20.0340 (8)0.0363 (9)0.0375 (9)0.0022 (6)0.0069 (7)0.0034 (7)
N10.0319 (8)0.0382 (9)0.0407 (9)0.0047 (6)0.0079 (7)0.0012 (7)
O20.0310 (7)0.0480 (9)0.0477 (9)0.0055 (6)0.0019 (6)0.0001 (7)
C90.0301 (9)0.0343 (10)0.0404 (10)−0.0017 (7)0.0103 (7)0.0048 (7)
C80.0390 (10)0.0389 (10)0.0375 (10)0.0040 (8)0.0122 (8)0.0011 (8)
C50.0389 (10)0.0369 (10)0.0343 (10)0.0005 (8)0.0099 (8)0.0016 (7)
O10.0453 (9)0.0744 (13)0.0518 (10)0.0062 (8)−0.0072 (7)−0.0129 (9)
C110.0408 (11)0.0411 (11)0.0596 (13)−0.0091 (9)0.0253 (10)−0.0152 (10)
C100.0287 (8)0.0361 (10)0.0380 (9)−0.0016 (7)0.0079 (7)0.0030 (8)
C20.0385 (10)0.0487 (12)0.0376 (10)−0.0005 (9)0.0033 (8)−0.0016 (9)
C30.0462 (12)0.0447 (12)0.0479 (12)0.0092 (9)0.0030 (9)−0.0065 (10)
C60.0508 (12)0.0478 (12)0.0417 (11)0.0087 (10)0.0091 (9)−0.0097 (9)
C70.0542 (13)0.0543 (14)0.0423 (11)0.0024 (11)0.0029 (10)−0.0153 (10)
C40.0477 (11)0.0401 (11)0.0422 (11)0.0043 (9)0.0005 (9)−0.0084 (9)
C130.0442 (11)0.0382 (11)0.0525 (12)0.0007 (9)0.0142 (9)−0.0021 (9)
C120.0386 (11)0.0480 (12)0.0505 (12)−0.0069 (9)0.0116 (9)−0.0118 (10)
C10.0423 (13)0.086 (2)0.0669 (17)0.0125 (13)0.0002 (11)−0.0018 (15)

Geometric parameters (Å, °)

S1—C131.694 (2)C11—H11A0.9300
S1—C101.727 (2)C2—C71.382 (3)
N2—C81.274 (3)C2—C31.386 (3)
N2—N11.366 (2)C3—C41.382 (3)
N1—C91.351 (3)C3—H3A0.9300
N1—H1A0.8600C6—C71.379 (3)
O2—C91.239 (2)C6—H6A0.9300
C9—C101.479 (3)C7—H7A0.9300
C8—C51.466 (3)C4—H4A0.9300
C8—H8A0.9300C13—C121.353 (3)
C5—C41.387 (3)C13—H13A0.9300
C5—C61.391 (3)C12—H12A0.9300
O1—C21.368 (3)C1—H1B0.9600
O1—C11.413 (3)C1—H1C0.9600
C11—C101.437 (3)C1—H1D0.9600
C11—C121.451 (3)
C13—S1—C1091.43 (11)C4—C3—C2119.6 (2)
C8—N2—N1115.96 (18)C4—C3—H3A120.2
C9—N1—N2121.10 (17)C2—C3—H3A120.2
C9—N1—H1A119.4C7—C6—C5121.3 (2)
N2—N1—H1A119.4C7—C6—H6A119.4
O2—C9—N1119.15 (19)C5—C6—H6A119.4
O2—C9—C10120.17 (19)C6—C7—C2119.8 (2)
N1—C9—C10120.68 (17)C6—C7—H7A120.1
N2—C8—C5121.42 (19)C2—C7—H7A120.1
N2—C8—H8A119.3C3—C4—C5121.3 (2)
C5—C8—H8A119.3C3—C4—H4A119.3
C4—C5—C6118.0 (2)C5—C4—H4A119.3
C4—C5—C8123.29 (19)C12—C13—S1113.72 (18)
C6—C5—C8118.65 (19)C12—C13—H13A123.1
C2—O1—C1117.9 (2)S1—C13—H13A123.1
C10—C11—C12107.8 (2)C13—C12—C11114.2 (2)
C10—C11—H11A126.1C13—C12—H12A122.9
C12—C11—H11A126.1C11—C12—H12A122.9
C11—C10—C9120.20 (18)O1—C1—H1B109.5
C11—C10—S1112.76 (16)O1—C1—H1C109.5
C9—C10—S1127.02 (15)H1B—C1—H1C109.5
O1—C2—C7115.6 (2)O1—C1—H1D109.5
O1—C2—C3124.4 (2)H1B—C1—H1D109.5
C7—C2—C3120.0 (2)H1C—C1—H1D109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.122.963 (2)167

Symmetry codes: (i) −x, −y+2, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5449).

References

  • Bruker (1997). SMART and SAINT Bruker AXS, Inc., Madison, Wisconsin, USA.
  • Li, Y.-F. & Jian, F.-F. (2010). Acta Cryst. E66, o1398. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography