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ISSN: 2056-9890

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

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[Li, Y.-F. & Jian, F.-F. (2008). Acta Cryst. E64, o2409.]).

[Scheme 1]

Experimental

Crystal data
  • C10H11ClN2O

  • Mr = 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)

  • Rint = 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

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

All H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H and N—H distances in the range 0.93–0.97Å and 0.86 Å, and with Uiso(H) = 1.2Ueq of the parent atoms.

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
[Figure 1] 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
C10H11ClN2OF(000) = 440
Mr = 210.66Dx = 1.333 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2368 reflections
a = 15.944 (3) Åθ = 3.1–27.5°
b = 5.0061 (10) ŵ = 0.33 mm1
c = 13.950 (3) ÅT = 293 K
β = 109.45 (3)°Bar, yellow
V = 1049.9 (4) Å30.25 × 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 tubeRint = 0.028
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
phi and ω scansh = 2020
9225 measured reflectionsk = 66
2368 independent reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H atoms treated by a mixture of independent and constrained refinement
S = 1.22 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
2368 reflections(Δ/σ)max < 0.001
143 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C10H11ClN2OV = 1049.9 (4) Å3
Mr = 210.66Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.944 (3) ŵ = 0.33 mm1
b = 5.0061 (10) ÅT = 293 K
c = 13.950 (3) Å0.25 × 0.20 × 0.20 mm
β = 109.45 (3)°
Data collection top
Bruker SMART CCD
diffractometer
1840 reflections with I > 2σ(I)
9225 measured reflectionsRint = 0.028
2368 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.164H atoms treated by a mixture of independent and constrained refinement
S = 1.22Δρmax = 0.29 e Å3
2368 reflectionsΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
Cl10.05552 (4)0.51605 (12)0.20233 (5)0.0784 (3)
O10.58233 (7)0.3084 (2)0.08042 (9)0.0515 (3)
N20.43948 (8)0.2513 (3)0.06514 (10)0.0437 (3)
N10.37755 (9)0.1121 (3)0.09450 (10)0.0450 (3)
C40.29443 (11)0.1619 (3)0.04835 (12)0.0449 (4)
C50.23285 (11)0.0057 (3)0.08658 (12)0.0449 (4)
C20.52624 (10)0.1844 (3)0.10492 (11)0.0409 (3)
C80.12309 (12)0.3099 (3)0.15743 (15)0.0544 (4)
C70.20770 (13)0.2495 (4)0.22141 (14)0.0598 (5)
H7A0.22800.31420.28770.072*
C60.26121 (11)0.0927 (4)0.18559 (13)0.0544 (4)
H6A0.31810.05070.22870.065*
C100.14651 (12)0.0543 (4)0.02497 (14)0.0572 (5)
H10A0.12510.01320.04080.069*
C10.55118 (11)0.0442 (3)0.17832 (14)0.0517 (4)
H1B0.61440.07000.20040.078*
H1C0.53320.00540.23600.078*
H1D0.52190.20360.14560.078*
C90.09182 (12)0.2137 (4)0.06054 (15)0.0620 (5)
H9A0.03440.25440.01860.074*
C30.25881 (16)0.3524 (5)0.0385 (2)0.0663 (6)
H2A0.4257 (13)0.391 (4)0.0186 (17)0.062 (5)*
H3A0.197 (2)0.372 (5)0.064 (2)0.106 (9)*
H3B0.279 (3)0.503 (7)0.022 (3)0.155 (16)*
H3C0.278 (2)0.321 (6)0.094 (2)0.115 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0715 (4)0.0887 (5)0.0850 (5)0.0221 (3)0.0396 (3)0.0014 (3)
O10.0511 (6)0.0533 (6)0.0489 (7)0.0016 (5)0.0151 (5)0.0108 (5)
N20.0479 (7)0.0422 (7)0.0401 (7)0.0027 (6)0.0134 (5)0.0058 (5)
N10.0475 (7)0.0469 (7)0.0399 (7)0.0038 (6)0.0137 (5)0.0018 (5)
C40.0495 (8)0.0424 (8)0.0417 (8)0.0018 (6)0.0138 (6)0.0016 (6)
C50.0462 (9)0.0451 (8)0.0414 (9)0.0024 (6)0.0119 (7)0.0029 (6)
C20.0510 (8)0.0378 (7)0.0325 (7)0.0033 (6)0.0122 (6)0.0004 (5)
C80.0520 (9)0.0554 (9)0.0615 (11)0.0043 (7)0.0267 (8)0.0037 (8)
C70.0601 (10)0.0706 (11)0.0469 (10)0.0085 (9)0.0154 (8)0.0030 (8)
C60.0501 (9)0.0641 (10)0.0442 (9)0.0074 (8)0.0092 (7)0.0016 (7)
C100.0466 (9)0.0701 (11)0.0496 (10)0.0019 (8)0.0089 (7)0.0065 (8)
C10.0571 (10)0.0488 (9)0.0491 (10)0.0064 (7)0.0175 (7)0.0115 (7)
C90.0429 (8)0.0705 (11)0.0663 (12)0.0032 (8)0.0097 (8)0.0008 (9)
C30.0595 (12)0.0661 (13)0.0687 (14)0.0060 (10)0.0154 (10)0.0225 (10)
Geometric parameters (Å, º) top
Cl1—C81.7512 (17)C7—C61.370 (2)
O1—C21.2269 (18)C7—H7A0.9300
N2—C21.350 (2)C6—H6A0.9300
N2—N11.3773 (17)C10—C91.390 (3)
N2—H2A0.93 (2)C10—H10A0.9300
N1—C41.290 (2)C1—H1B0.9600
C4—C51.486 (2)C1—H1C0.9600
C4—C31.497 (2)C1—H1D0.9600
C5—C101.391 (2)C9—H9A0.9300
C5—C61.392 (2)C3—H3A0.93 (3)
C2—C11.498 (2)C3—H3B0.83 (4)
C8—C91.363 (3)C3—H3C0.94 (3)
C8—C71.381 (3)
C2—N2—N1119.36 (13)C7—C6—H6A119.1
C2—N2—H2A116.5 (12)C5—C6—H6A119.1
N1—N2—H2A124.2 (12)C9—C10—C5120.84 (17)
C4—N1—N2118.22 (13)C9—C10—H10A119.6
N1—C4—C5114.25 (13)C5—C10—H10A119.6
N1—C4—C3125.23 (16)C2—C1—H1B109.5
C5—C4—C3120.50 (15)C2—C1—H1C109.5
C10—C5—C6117.66 (16)H1B—C1—H1C109.5
C10—C5—C4121.86 (15)C2—C1—H1D109.5
C6—C5—C4120.46 (14)H1B—C1—H1D109.5
O1—C2—N2120.14 (14)H1C—C1—H1D109.5
O1—C2—C1121.64 (14)C8—C9—C10119.41 (16)
N2—C2—C1118.22 (14)C8—C9—H9A120.3
C9—C8—C7121.30 (16)C10—C9—H9A120.3
C9—C8—Cl1119.82 (14)C4—C3—H3A116.6 (17)
C7—C8—Cl1118.88 (15)C4—C3—H3B110 (3)
C6—C7—C8118.87 (17)H3A—C3—H3B106 (3)
C6—C7—H7A120.6C4—C3—H3C115.3 (18)
C8—C7—H7A120.6H3A—C3—H3C107 (2)
C7—C6—C5121.89 (16)H3B—C3—H3C101 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.93 (2)2.02 (2)2.9384 (18)170.3 (18)
Symmetry code: (i) x+1, y1, z.

Experimental details

Crystal data
Chemical formulaC10H11ClN2O
Mr210.66
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)15.944 (3), 5.0061 (10), 13.950 (3)
β (°) 109.45 (3)
V3)1049.9 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.33
Crystal size (mm)0.25 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9225, 2368, 1840
Rint0.028
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.164, 1.22
No. of reflections2368
No. of parameters143
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N2—H2A···O1i0.93 (2)2.02 (2)2.9384 (18)170.3 (18)
Symmetry code: (i) x+1, y1, z.
 

Acknowledgements

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

References

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

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
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