N′-(3,4-Dimethyl­benzyl­idene)furan-2-carbohydrazide

Li, Y.-F.; Jian, F.-F.

doi:10.1107/S1600536810027959

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2061

https://doi.org/10.1107/S1600536810027959

Open

access

N′-(3,4-Dimethylbenzylidene)furan-2-carbohydrazide

Yu-Feng Li ^a and Fang-Fang Jian ^b ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^bMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: liyufeng8111@163.com

(Received 12 July 2010; accepted 14 July 2010; online 17 July 2010)

The title compound, C₁₄H₁₄N₂O₂, was prepared by the reaction of 3,4-dimethylbenzaldehyde and furan-2-carbohydrazide. The dihedral angle between the aromatic rings is 35.48 (14)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, generating C(4) chains propagating in [010].

Related literature

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

Experimental

Crystal data

C₁₄H₁₄N₂O₂
M_r = 242.27
Orthorhombic, P b c a
a = 17.655 (3) Å
b = 7.6304 (15) Å
c = 19.020 (4) Å
V = 2562.3 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.22 × 0.21 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
21744 measured reflections
2921 independent reflections
1563 reflections with I > 2σ(I)
R_int = 0.127

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.177
S = 0.90
2921 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.86	2.06	2.921 (3)	174
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810027959/hb5553sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027959/hb5553Isup2.hkl

checkCIF report

Related literature top

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

Experimental top

A mixture of 3,4-dimethylbenzaldehyde (0.1 mol), and furan-2-carbohydrazide (0.1 mol) was stirred in refluxing ethanol (20 mL) for 2 h to afford the title compound (0.090 mol, yield 90%). olourless blocks of (I) were obtained by recrystallization from ethanol at room temperature.

Structure description top

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

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

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

N'-(3,4-Dimethylbenzylidene)furan-2-carbohydrazide top

Crystal data top

C₁₄H₁₄N₂O₂	F(000) = 1024
M_r = 242.27	D_x = 1.256 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1563 reflections
a = 17.655 (3) Å	θ = 3.1–27.5°
b = 7.6304 (15) Å	µ = 0.09 mm⁻¹
c = 19.020 (4) Å	T = 293 K
V = 2562.3 (9) Å³	Block, colorless
Z = 8	0.22 × 0.21 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	1563 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.127
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
phi and ω scans	h = −22→22
21744 measured reflections	k = −9→9
2921 independent reflections	l = −24→23

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.177	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
2921 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₄H₁₄N₂O₂	V = 2562.3 (9) Å³
M_r = 242.27	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 17.655 (3) Å	µ = 0.09 mm⁻¹
b = 7.6304 (15) Å	T = 293 K
c = 19.020 (4) Å	0.22 × 0.21 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	1563 reflections with I > 2σ(I)
21744 measured reflections	R_int = 0.127
2921 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.177	H-atom parameters constrained
S = 0.90	Δρ_max = 0.15 e Å⁻³
2921 reflections	Δρ_min = −0.21 e Å⁻³
163 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
O2	0.34251 (10)	0.2908 (2)	0.40087 (10)	0.0493 (5)
N2	0.23842 (12)	0.1209 (2)	0.38067 (10)	0.0404 (5)
H2A	0.2147	0.0251	0.3897	0.048*
N1	0.20989 (11)	0.2401 (3)	0.33290 (10)	0.0391 (5)
C1	0.32632 (14)	0.0301 (3)	0.46664 (13)	0.0393 (6)
C6	0.15127 (14)	0.1915 (3)	0.29934 (12)	0.0412 (6)
H6A	0.1308	0.0813	0.3079	0.049*
C5	0.30454 (14)	0.1586 (3)	0.41282 (12)	0.0384 (6)
C7	0.11563 (14)	0.3062 (3)	0.24746 (12)	0.0397 (6)
C9	0.11430 (15)	0.5784 (3)	0.18082 (13)	0.0456 (7)
C4	0.40945 (19)	−0.1050 (4)	0.53228 (14)	0.0580 (8)
H4A	0.4554	−0.1425	0.5508	0.070*
C8	0.14661 (15)	0.4693 (3)	0.23064 (13)	0.0439 (7)
H8A	0.1903	0.5058	0.2536	0.053*
C2	0.28720 (16)	−0.0713 (3)	0.51175 (13)	0.0469 (7)
H2B	0.2348	−0.0819	0.5147	0.056*
C12	0.04994 (14)	0.2541 (3)	0.21381 (12)	0.0441 (7)
H12A	0.0277	0.1472	0.2249	0.053*
C11	0.01738 (15)	0.3619 (4)	0.16343 (13)	0.0475 (7)
H11A	−0.0265	0.3252	0.1407	0.057*
C3	0.34193 (18)	−0.1595 (4)	0.55411 (14)	0.0532 (7)
H3A	0.3323	−0.2394	0.5899	0.064*
C14	0.1495 (2)	0.7546 (4)	0.16590 (19)	0.0728 (10)
H14A	0.1940	0.7691	0.1944	0.109*
H14B	0.1138	0.8455	0.1767	0.109*
H14C	0.1632	0.7614	0.1171	0.109*
C13	0.01177 (19)	0.6353 (4)	0.09024 (15)	0.0709 (9)
H13A	−0.0325	0.5771	0.0724	0.106*
H13B	0.0470	0.6543	0.0525	0.106*
H13C	−0.0025	0.7459	0.1103	0.106*
O1	0.40208 (10)	0.0140 (3)	0.47873 (9)	0.0542 (6)
C10	0.04847 (15)	0.5226 (4)	0.14611 (12)	0.0459 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0437 (11)	0.0356 (10)	0.0687 (12)	−0.0029 (9)	0.0024 (8)	0.0115 (9)
N2	0.0499 (14)	0.0268 (11)	0.0444 (12)	−0.0013 (10)	−0.0043 (10)	0.0097 (9)
N1	0.0449 (13)	0.0310 (12)	0.0414 (12)	0.0036 (10)	−0.0041 (10)	0.0055 (9)
C1	0.0420 (15)	0.0323 (14)	0.0437 (14)	0.0024 (12)	−0.0047 (11)	−0.0028 (10)
C6	0.0483 (16)	0.0307 (14)	0.0446 (15)	−0.0021 (12)	0.0013 (12)	0.0039 (11)
C5	0.0420 (15)	0.0307 (14)	0.0424 (14)	0.0062 (12)	0.0032 (11)	−0.0005 (11)
C7	0.0424 (15)	0.0371 (15)	0.0395 (13)	0.0048 (11)	0.0014 (11)	0.0012 (11)
C9	0.0524 (17)	0.0404 (16)	0.0439 (14)	0.0035 (13)	0.0026 (12)	0.0060 (11)
C4	0.064 (2)	0.059 (2)	0.0503 (16)	0.0179 (17)	−0.0090 (14)	0.0095 (14)
C8	0.0466 (16)	0.0403 (16)	0.0448 (15)	0.0000 (13)	−0.0052 (12)	0.0042 (11)
C2	0.0533 (17)	0.0425 (16)	0.0450 (15)	−0.0056 (13)	−0.0088 (12)	0.0069 (12)
C12	0.0444 (16)	0.0435 (16)	0.0444 (15)	−0.0036 (13)	0.0012 (12)	−0.0010 (11)
C11	0.0379 (15)	0.0606 (19)	0.0440 (14)	0.0055 (14)	−0.0016 (11)	−0.0060 (13)
C3	0.068 (2)	0.0452 (17)	0.0461 (16)	0.0005 (15)	−0.0108 (14)	0.0060 (13)
C14	0.084 (2)	0.050 (2)	0.085 (2)	−0.0049 (18)	−0.0098 (18)	0.0256 (16)
C13	0.071 (2)	0.085 (2)	0.0564 (17)	0.0207 (19)	−0.0098 (16)	0.0175 (16)
O1	0.0446 (11)	0.0575 (13)	0.0604 (12)	0.0110 (10)	−0.0020 (9)	0.0143 (9)
C10	0.0486 (16)	0.0547 (18)	0.0345 (13)	0.0138 (14)	0.0026 (11)	0.0035 (12)

Geometric parameters (Å, º) top

O2—C5	1.232 (3)	C4—H4A	0.9300
N2—C5	1.349 (3)	C8—H8A	0.9300
N2—N1	1.381 (3)	C2—C3	1.427 (4)
N2—H2A	0.8600	C2—H2B	0.9300
N1—C6	1.271 (3)	C12—C11	1.388 (4)
C1—C2	1.346 (4)	C12—H12A	0.9300
C1—O1	1.363 (3)	C11—C10	1.383 (4)
C1—C5	1.469 (3)	C11—H11A	0.9300
C6—C7	1.462 (3)	C3—H3A	0.9300
C6—H6A	0.9300	C14—H14A	0.9600
C7—C12	1.383 (3)	C14—H14B	0.9600
C7—C8	1.396 (4)	C14—H14C	0.9600
C9—C8	1.384 (3)	C13—C10	1.513 (4)
C9—C10	1.403 (4)	C13—H13A	0.9600
C9—C14	1.508 (4)	C13—H13B	0.9600
C4—C3	1.329 (4)	C13—H13C	0.9600
C4—O1	1.371 (3)

C5—N2—N1	118.3 (2)	C3—C2—H2B	126.8
C5—N2—H2A	120.9	C7—C12—C11	119.8 (2)
N1—N2—H2A	120.9	C7—C12—H12A	120.1
C6—N1—N2	115.8 (2)	C11—C12—H12A	120.1
C2—C1—O1	110.1 (2)	C10—C11—C12	121.7 (3)
C2—C1—C5	133.9 (2)	C10—C11—H11A	119.1
O1—C1—C5	115.8 (2)	C12—C11—H11A	119.1
N1—C6—C7	121.0 (2)	C4—C3—C2	106.5 (3)
N1—C6—H6A	119.5	C4—C3—H3A	126.8
C7—C6—H6A	119.5	C2—C3—H3A	126.8
O2—C5—N2	124.2 (2)	C9—C14—H14A	109.5
O2—C5—C1	122.2 (2)	C9—C14—H14B	109.5
N2—C5—C1	113.6 (2)	H14A—C14—H14B	109.5
C12—C7—C8	118.6 (2)	C9—C14—H14C	109.5
C12—C7—C6	120.1 (2)	H14A—C14—H14C	109.5
C8—C7—C6	121.3 (2)	H14B—C14—H14C	109.5
C8—C9—C10	118.7 (2)	C10—C13—H13A	109.5
C8—C9—C14	119.7 (3)	C10—C13—H13B	109.5
C10—C9—C14	121.6 (2)	H13A—C13—H13B	109.5
C3—C4—O1	110.8 (3)	C10—C13—H13C	109.5
C3—C4—H4A	124.6	H13A—C13—H13C	109.5
O1—C4—H4A	124.6	H13B—C13—H13C	109.5
C9—C8—C7	122.1 (2)	C1—O1—C4	106.2 (2)
C9—C8—H8A	118.9	C11—C10—C9	119.1 (2)
C7—C8—H8A	118.9	C11—C10—C13	120.1 (3)
C1—C2—C3	106.5 (3)	C9—C10—C13	120.9 (3)
C1—C2—H2B	126.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.06	2.921 (3)	174

Symmetry code: (i) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₂O₂
M_r	242.27
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	17.655 (3), 7.6304 (15), 19.020 (4)
V (Å³)	2562.3 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.22 × 0.21 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21744, 2921, 1563
R_int	0.127
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.177, 0.90
No. of reflections	2921
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.21

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.06	2.921 (3)	174

Symmetry code: (i) −x+1/2, y−1/2, z.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, Y.-F. & Jian, F.-F. (2010). Acta Cryst. E66, o1720. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals 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 66| Part 8| August 2010| Page o2061

https://doi.org/10.1107/S1600536810027959

Open

access