N′-(2,6-Dichloro­benzyl­idene)furan-2-carbohydrazide

Xu, J.

doi:10.1107/S160053681201639X

organic compounds

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doi:10.1107/S160053681201639X

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N′-(2,6-Dichlorobenzylidene)furan-2-carbohydrazide

Jun Xu ^a ^*

^aDepartment of Quality Detection and Management, Zhengzhou College of Animal Husbandry Engineering, Zhengzhou 450011, People's Republic of China
^*Correspondence e-mail: xujun20101996@yahoo.com.cn

(Received 14 April 2012; accepted 16 April 2012; online 21 April 2012)

In the title compound, C₁₂H₈Cl₂N₂O₂, the dihedral angle between the furan and benzene rings is 72.90 (16)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, generating C(4) chains propagating in [100].

Related literature

For related structures, see: Okabe et al. (1993 ); Ohba (1996 ); Bakir & Gyles (2003 ).

Experimental

Crystal data

C₁₂H₈Cl₂N₂O₂
M_r = 283.10
Monoclinic, P 2₁ /c
a = 4.9046 (3) Å
b = 19.1113 (12) Å
c = 12.9469 (9) Å
β = 91.565 (5)°
V = 1213.10 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.53 mm⁻¹
T = 293 K
0.21 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.814, T_max = 0.847
4654 measured reflections
2464 independent reflections
1679 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.126
S = 1.01
2464 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.07	2.890 (2)	159
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681201639X/hb6741sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201639X/hb6741Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201639X/hb6741Isup3.cml

checkCIF report

Comment top

Several phenylhydrazone derivatives have been shown to be potentially DNA-damaging and are mutagenic agents (Okabe et al., 1993). As part of our ongoing studies of these materials, we synthesized the title compound, (I), and the crystal structure is presented herein. In the molecular structure of the compound, the molecular is not planar, the furyl ring makes a dihedral angle of 72.90 (16)° with the benzene ring. Bond lengths and angles are in agreement with other hydrazone derivatives (Ohba, 1996; Bakir & Gyles, 2003).

In the crystal, molecules are linked by N—H···O hydrogen bonds, generating one-dimensional chains.

Related literature top

For related structures, see: Okabe et al. (1993); Ohba (1996); Bakir & Gyles (2003).

Experimental top

Furan-2-carbohydrazine (1 mmol, 0.126 g) was dissolved in anhydrous ethanol (10 ml), The mixture was stirred for several minitutes at 351k, 2,6-Dichlorobenzaldehyde (1 mmol, 0.175 g) in ethanol (20 mm l) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized from DMF. Colorless blocks were obtained by slow evaporation of the compound dissoived in a mixture of ethanol and DMF.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Voew of (I). Displacement ellipsoids are drawn at the 30% probability level. showing the intramolecular hydrogen bonds as dashed lines.
	Fig. 2. The molecular packing of the title compound,

N'-(2,6-Dichlorobenzylidene)furan-2-carbohydrazide top

Crystal data top

C₁₂H₈Cl₂N₂O₂	F(000) = 576
M_r = 283.10	D_x = 1.550 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2790 reflections
a = 4.9046 (3) Å	θ = 3.2–26.3°
b = 19.1113 (12) Å	µ = 0.53 mm⁻¹
c = 12.9469 (9) Å	T = 293 K
β = 91.565 (5)°	Block, colorless
V = 1213.10 (14) Å³	0.21 × 0.18 × 0.17 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2464 independent reflections
Radiation source: fine-focus sealed tube	1679 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 26.4°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −5→6
T_min = 0.814, T_max = 0.847	k = −22→23
4654 measured reflections	l = −16→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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0537P)² + 0.2769P] where P = (F_o² + 2F_c²)/3
2464 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₂H₈Cl₂N₂O₂	V = 1213.10 (14) Å³
M_r = 283.10	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.9046 (3) Å	µ = 0.53 mm⁻¹
b = 19.1113 (12) Å	T = 293 K
c = 12.9469 (9) Å	0.21 × 0.18 × 0.17 mm
β = 91.565 (5)°

Data collection top

Bruker SMART CCD diffractometer	2464 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1679 reflections with I > 2σ(I)
T_min = 0.814, T_max = 0.847	R_int = 0.028
4654 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.01	Δρ_max = 0.23 e Å⁻³
2464 reflections	Δρ_min = −0.30 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
Cl1	0.43228 (17)	0.43978 (4)	0.09622 (7)	0.0649 (3)
Cl2	−0.28672 (16)	0.52357 (5)	0.38143 (7)	0.0679 (3)
O1	0.5843 (3)	0.68141 (9)	0.10167 (15)	0.0429 (5)
N1	0.1507 (4)	0.63974 (10)	0.09980 (16)	0.0345 (5)
H1A	−0.0175	0.6482	0.0838	0.041*
C5	0.3496 (5)	0.68267 (12)	0.06671 (19)	0.0322 (6)
N2	0.2201 (4)	0.58266 (10)	0.15913 (16)	0.0342 (5)
O	0.4344 (4)	0.78012 (11)	−0.04747 (17)	0.0591 (6)
C7	0.0788 (5)	0.47943 (13)	0.2441 (2)	0.0367 (6)
C4	0.2594 (5)	0.72916 (12)	−0.0172 (2)	0.0341 (6)
C12	−0.0570 (5)	0.46354 (15)	0.3342 (2)	0.0452 (7)
C6	0.0226 (5)	0.54460 (13)	0.1877 (2)	0.0357 (6)
H6A	−0.1564	0.5581	0.1729	0.043*
C3	0.0404 (5)	0.72915 (15)	−0.0800 (2)	0.0464 (7)
H3A	−0.1086	0.6993	−0.0761	0.056*
C11	−0.0117 (7)	0.40168 (19)	0.3879 (3)	0.0630 (9)
H11A	−0.1082	0.3920	0.4471	0.076*
C8	0.2643 (5)	0.42899 (14)	0.2112 (2)	0.0440 (7)
C9	0.3144 (6)	0.36796 (16)	0.2651 (3)	0.0596 (9)
H9A	0.4412	0.3358	0.2418	0.071*
C1	0.3139 (6)	0.81122 (17)	−0.1316 (3)	0.0603 (9)
H1B	0.3901	0.8477	−0.1686	0.072*
C10	0.1756 (7)	0.35512 (19)	0.3533 (3)	0.0698 (10)
H10A	0.2094	0.3141	0.3901	0.084*
C2	0.0749 (6)	0.78259 (17)	−0.1535 (2)	0.0578 (8)
H2B	−0.0466	0.7951	−0.2068	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0791 (6)	0.0484 (5)	0.0682 (6)	0.0052 (4)	0.0217 (4)	−0.0113 (4)
Cl2	0.0658 (5)	0.0828 (7)	0.0559 (5)	−0.0035 (4)	0.0182 (4)	−0.0036 (5)
O1	0.0292 (9)	0.0457 (11)	0.0537 (12)	−0.0007 (7)	−0.0008 (8)	0.0043 (10)
N1	0.0292 (10)	0.0329 (11)	0.0413 (13)	0.0004 (8)	0.0004 (9)	0.0082 (11)
C5	0.0318 (12)	0.0296 (12)	0.0355 (14)	0.0012 (9)	0.0062 (10)	−0.0048 (12)
N2	0.0384 (11)	0.0289 (10)	0.0352 (12)	−0.0006 (9)	−0.0006 (9)	0.0026 (10)
O	0.0528 (11)	0.0557 (13)	0.0682 (15)	−0.0172 (9)	−0.0062 (10)	0.0223 (12)
C7	0.0410 (13)	0.0336 (13)	0.0352 (14)	−0.0083 (10)	−0.0076 (11)	0.0036 (12)
C4	0.0382 (12)	0.0274 (12)	0.0371 (14)	−0.0015 (10)	0.0076 (11)	0.0011 (12)
C12	0.0477 (15)	0.0479 (17)	0.0399 (16)	−0.0100 (12)	−0.0039 (12)	0.0042 (14)
C6	0.0349 (13)	0.0362 (13)	0.0359 (15)	−0.0011 (10)	−0.0002 (11)	0.0022 (12)
C3	0.0424 (14)	0.0544 (17)	0.0424 (16)	−0.0126 (12)	−0.0027 (12)	0.0150 (15)
C11	0.074 (2)	0.067 (2)	0.0473 (19)	−0.0242 (18)	−0.0090 (16)	0.0222 (18)
C8	0.0497 (15)	0.0348 (14)	0.0470 (17)	−0.0055 (12)	−0.0073 (13)	0.0009 (14)
C9	0.0660 (19)	0.0359 (16)	0.076 (2)	0.0018 (13)	−0.0177 (17)	0.0025 (17)
C1	0.070 (2)	0.0499 (18)	0.061 (2)	−0.0085 (15)	0.0033 (17)	0.0271 (18)
C10	0.085 (2)	0.051 (2)	0.072 (3)	−0.0080 (17)	−0.025 (2)	0.025 (2)
C2	0.0581 (18)	0.064 (2)	0.0505 (19)	0.0017 (15)	−0.0056 (14)	0.0179 (18)

Geometric parameters (Å, º) top

Cl1—C8	1.733 (3)	C12—C11	1.387 (4)
Cl2—C12	1.731 (3)	C6—H6A	0.9300
O1—C5	1.226 (3)	C3—C2	1.410 (4)
N1—C5	1.353 (3)	C3—H3A	0.9300
N1—N2	1.372 (3)	C11—C10	1.363 (5)
N1—H1A	0.8600	C11—H11A	0.9300
C5—C4	1.463 (3)	C8—C9	1.378 (4)
N2—C6	1.275 (3)	C9—C10	1.367 (4)
O—C1	1.362 (4)	C9—H9A	0.9300
O—C4	1.363 (3)	C1—C2	1.318 (4)
C7—C12	1.392 (4)	C1—H1B	0.9300
C7—C8	1.400 (4)	C10—H10A	0.9300
C7—C6	1.466 (3)	C2—H2B	0.9300
C4—C3	1.329 (4)

C5—N1—N2	119.29 (19)	C4—C3—H3A	126.2
C5—N1—H1A	120.4	C2—C3—H3A	126.2
N2—N1—H1A	120.4	C10—C11—C12	119.4 (3)
O1—C5—N1	123.3 (2)	C10—C11—H11A	120.3
O1—C5—C4	123.3 (2)	C12—C11—H11A	120.3
N1—C5—C4	113.4 (2)	C9—C8—C7	122.5 (3)
C6—N2—N1	115.94 (19)	C9—C8—Cl1	117.0 (2)
C1—O—C4	106.2 (2)	C7—C8—Cl1	120.5 (2)
C12—C7—C8	115.8 (2)	C10—C9—C8	119.3 (3)
C12—C7—C6	121.0 (2)	C10—C9—H9A	120.4
C8—C7—C6	123.3 (2)	C8—C9—H9A	120.4
C3—C4—O	109.2 (2)	C2—C1—O	110.8 (3)
C3—C4—C5	132.6 (2)	C2—C1—H1B	124.6
O—C4—C5	117.9 (2)	O—C1—H1B	124.6
C11—C12—C7	122.2 (3)	C11—C10—C9	120.8 (3)
C11—C12—Cl2	119.0 (2)	C11—C10—H10A	119.6
C7—C12—Cl2	118.8 (2)	C9—C10—H10A	119.6
N2—C6—C7	119.7 (2)	C1—C2—C3	106.1 (3)
N2—C6—H6A	120.2	C1—C2—H2B	126.9
C7—C6—H6A	120.2	C3—C2—H2B	126.9
C4—C3—C2	107.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.07	2.890 (2)	159

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₈Cl₂N₂O₂
M_r	283.10
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	4.9046 (3), 19.1113 (12), 12.9469 (9)
β (°)	91.565 (5)
V (Å³)	1213.10 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.53
Crystal size (mm)	0.21 × 0.18 × 0.17

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.814, 0.847
No. of measured, independent and observed [I > 2σ(I)] reflections	4654, 2464, 1679
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.126, 1.01
No. of reflections	2464
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.30

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.07	2.890 (2)	159

Symmetry code: (i) x−1, y, z.

References

Bakir, M. & Gyles, C. (2003). J. Mol. Struct. 649, 133–135. Web of Science CSD CrossRef CAS Google Scholar
Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ohba, S. (1996). Acta Cryst. C52, 2118–2119. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678–1680. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1455

doi:10.1107/S160053681201639X

Open

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