N′-[1-(4-Chloro­phen­yl)ethyl­idene]acetohydrazide

Guo, H.; Wu, Q.; Yang, J.; Liu, Y.

doi:10.1107/S1600536810042546

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2941

https://doi.org/10.1107/S1600536810042546

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N′-[1-(4-Chlorophenyl)ethylidene]acetohydrazide

Huan-mei Guo,^a ^* Qian Wu,^a Jie Yang ^a and Yang-chun Liu ^b

^aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China, and ^bDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 15 October 2010; accepted 20 October 2010; online 23 October 2010)

In the title compound, C₁₀H₁₁ClN₂O, the dihedral angle between the acetohydrazide group and the aromatic ring is 33.76 (9)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R₂²(8) loops.

Related literature

For a related structure, see: Li & Jian (2008 ).

Experimental

Crystal data

C₁₀H₁₁ClN₂O
M_r = 210.66
Monoclinic, P 2₁ /c
a = 15.944 (3) Å
b = 5.0061 (10) Å
c = 13.950 (3) Å
β = 109.45 (3)°
V = 1049.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
9225 measured reflections
2368 independent reflections
1840 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.164
S = 1.22
2368 reflections
143 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.93 (2)	2.02 (2)	2.9384 (18)	170.3 (18)
Symmetry code: (i) -x+1, -y-1, -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/S1600536810042546/hb5687sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042546/hb5687Isup2.hkl

checkCIF report

Related literature top

For a related structure, see: Li & Jian (2008).

Experimental top

A mixture of 4-fluorobenzophenone (0.02 mol) and acethydrazide (0.02 mol) was stirred in refluxing ethanol(30 ml) for 2 h to afford the title compound (yield 82%). Yellow bars of (I) were obtained by recrystallization from acetic ether at room temperature.

Structure description top

For a related structure, see: Li & Jian (2008).

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 the title compound with displacement ellipsoids drawn at the 30% probability level.

N'-[1-(4-Chlorophenyl)ethylidene]acetohydrazide top

Crystal data top

C₁₀H₁₁ClN₂O	F(000) = 440
M_r = 210.66	D_x = 1.333 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2368 reflections
a = 15.944 (3) Å	θ = 3.1–27.5°
b = 5.0061 (10) Å	µ = 0.33 mm⁻¹
c = 13.950 (3) Å	T = 293 K
β = 109.45 (3)°	Bar, yellow
V = 1049.9 (4) Å³	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	1840 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
phi and ω scans	h = −20→20
9225 measured reflections	k = −6→6
2368 independent reflections	l = −18→18

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.22	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
2368 reflections	(Δ/σ)_max < 0.001
143 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₀H₁₁ClN₂O	V = 1049.9 (4) Å³
M_r = 210.66	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.944 (3) Å	µ = 0.33 mm⁻¹
b = 5.0061 (10) Å	T = 293 K
c = 13.950 (3) Å	0.25 × 0.20 × 0.20 mm
β = 109.45 (3)°

Data collection top

Bruker SMART CCD diffractometer	1840 reflections with I > 2σ(I)
9225 measured reflections	R_int = 0.028
2368 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.22	Δρ_max = 0.29 e Å⁻³
2368 reflections	Δρ_min = −0.22 e Å⁻³
143 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	0.05552 (4)	0.51605 (12)	0.20233 (5)	0.0784 (3)
O1	0.58233 (7)	−0.3084 (2)	0.08042 (9)	0.0515 (3)
N2	0.43948 (8)	−0.2513 (3)	0.06514 (10)	0.0437 (3)
N1	0.37755 (9)	−0.1121 (3)	0.09450 (10)	0.0450 (3)
C4	0.29443 (11)	−0.1619 (3)	0.04835 (12)	0.0449 (4)
C5	0.23285 (11)	−0.0057 (3)	0.08658 (12)	0.0449 (4)
C2	0.52624 (10)	−0.1844 (3)	0.10492 (11)	0.0409 (3)
C8	0.12309 (12)	0.3099 (3)	0.15743 (15)	0.0544 (4)
C7	0.20770 (13)	0.2495 (4)	0.22141 (14)	0.0598 (5)
H7A	0.2280	0.3142	0.2877	0.072*
C6	0.26121 (11)	0.0927 (4)	0.18559 (13)	0.0544 (4)
H6A	0.3181	0.0507	0.2287	0.065*
C10	0.14651 (12)	0.0543 (4)	0.02497 (14)	0.0572 (5)
H10A	0.1251	−0.0132	−0.0408	0.069*
C1	0.55118 (11)	0.0442 (3)	0.17832 (14)	0.0517 (4)
H1B	0.6144	0.0700	0.2004	0.078*
H1C	0.5332	0.0054	0.2360	0.078*
H1D	0.5219	0.2036	0.1456	0.078*
C9	0.09182 (12)	0.2137 (4)	0.06054 (15)	0.0620 (5)
H9A	0.0344	0.2544	0.0186	0.074*
C3	0.25881 (16)	−0.3524 (5)	−0.0385 (2)	0.0663 (6)
H2A	0.4257 (13)	−0.391 (4)	0.0186 (17)	0.062 (5)*
H3A	0.197 (2)	−0.372 (5)	−0.064 (2)	0.106 (9)*
H3B	0.279 (3)	−0.503 (7)	−0.022 (3)	0.155 (16)*
H3C	0.278 (2)	−0.321 (6)	−0.094 (2)	0.115 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0715 (4)	0.0887 (5)	0.0850 (5)	0.0221 (3)	0.0396 (3)	0.0014 (3)
O1	0.0511 (6)	0.0533 (6)	0.0489 (7)	0.0016 (5)	0.0151 (5)	−0.0108 (5)
N2	0.0479 (7)	0.0422 (7)	0.0401 (7)	0.0027 (6)	0.0134 (5)	−0.0058 (5)
N1	0.0475 (7)	0.0469 (7)	0.0399 (7)	0.0038 (6)	0.0137 (5)	−0.0018 (5)
C4	0.0495 (8)	0.0424 (8)	0.0417 (8)	−0.0018 (6)	0.0138 (6)	0.0016 (6)
C5	0.0462 (9)	0.0451 (8)	0.0414 (9)	−0.0024 (6)	0.0119 (7)	0.0029 (6)
C2	0.0510 (8)	0.0378 (7)	0.0325 (7)	0.0033 (6)	0.0122 (6)	0.0004 (5)
C8	0.0520 (9)	0.0554 (9)	0.0615 (11)	0.0043 (7)	0.0267 (8)	0.0037 (8)
C7	0.0601 (10)	0.0706 (11)	0.0469 (10)	0.0085 (9)	0.0154 (8)	−0.0030 (8)
C6	0.0501 (9)	0.0641 (10)	0.0442 (9)	0.0074 (8)	0.0092 (7)	−0.0016 (7)
C10	0.0466 (9)	0.0701 (11)	0.0496 (10)	−0.0019 (8)	0.0089 (7)	−0.0065 (8)
C1	0.0571 (10)	0.0488 (9)	0.0491 (10)	−0.0064 (7)	0.0175 (7)	−0.0115 (7)
C9	0.0429 (8)	0.0705 (11)	0.0663 (12)	0.0032 (8)	0.0097 (8)	0.0008 (9)
C3	0.0595 (12)	0.0661 (13)	0.0687 (14)	−0.0060 (10)	0.0154 (10)	−0.0225 (10)

Geometric parameters (Å, º) top

Cl1—C8	1.7512 (17)	C7—C6	1.370 (2)
O1—C2	1.2269 (18)	C7—H7A	0.9300
N2—C2	1.350 (2)	C6—H6A	0.9300
N2—N1	1.3773 (17)	C10—C9	1.390 (3)
N2—H2A	0.93 (2)	C10—H10A	0.9300
N1—C4	1.290 (2)	C1—H1B	0.9600
C4—C5	1.486 (2)	C1—H1C	0.9600
C4—C3	1.497 (2)	C1—H1D	0.9600
C5—C10	1.391 (2)	C9—H9A	0.9300
C5—C6	1.392 (2)	C3—H3A	0.93 (3)
C2—C1	1.498 (2)	C3—H3B	0.83 (4)
C8—C9	1.363 (3)	C3—H3C	0.94 (3)
C8—C7	1.381 (3)

C2—N2—N1	119.36 (13)	C7—C6—H6A	119.1
C2—N2—H2A	116.5 (12)	C5—C6—H6A	119.1
N1—N2—H2A	124.2 (12)	C9—C10—C5	120.84 (17)
C4—N1—N2	118.22 (13)	C9—C10—H10A	119.6
N1—C4—C5	114.25 (13)	C5—C10—H10A	119.6
N1—C4—C3	125.23 (16)	C2—C1—H1B	109.5
C5—C4—C3	120.50 (15)	C2—C1—H1C	109.5
C10—C5—C6	117.66 (16)	H1B—C1—H1C	109.5
C10—C5—C4	121.86 (15)	C2—C1—H1D	109.5
C6—C5—C4	120.46 (14)	H1B—C1—H1D	109.5
O1—C2—N2	120.14 (14)	H1C—C1—H1D	109.5
O1—C2—C1	121.64 (14)	C8—C9—C10	119.41 (16)
N2—C2—C1	118.22 (14)	C8—C9—H9A	120.3
C9—C8—C7	121.30 (16)	C10—C9—H9A	120.3
C9—C8—Cl1	119.82 (14)	C4—C3—H3A	116.6 (17)
C7—C8—Cl1	118.88 (15)	C4—C3—H3B	110 (3)
C6—C7—C8	118.87 (17)	H3A—C3—H3B	106 (3)
C6—C7—H7A	120.6	C4—C3—H3C	115.3 (18)
C8—C7—H7A	120.6	H3A—C3—H3C	107 (2)
C7—C6—C5	121.89 (16)	H3B—C3—H3C	101 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.93 (2)	2.02 (2)	2.9384 (18)	170.3 (18)

Symmetry code: (i) −x+1, −y−1, −z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁ClN₂O
M_r	210.66
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.944 (3), 5.0061 (10), 13.950 (3)
β (°)	109.45 (3)
V (Å³)	1049.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9225, 2368, 1840
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.164, 1.22
No. of reflections	2368
No. of parameters	143
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.22

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···O1ⁱ	0.93 (2)	2.02 (2)	2.9384 (18)	170.3 (18)

Symmetry code: (i) −x+1, −y−1, −z.

Acknowledgements

The authors would like to thank the National Natural Science Foundation of Shandong Province (Y2008B29) and Yuandu Scholar of Weifang City.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, Y.-F. & Jian, F.-F. (2008). Acta Cryst. E64, o2409. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar