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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2691.
Published online 2010 September 30. doi:  10.1107/S1600536810038353
PMCID: PMC2983336

1-(1-Phenyl­ethyl­idene)carbonohydrazide

Abstract

The title compound, C9H12N4O, crystallizes with two independent mol­ecules in the asymmetric unit. In the crystal, inter­molecular N—H(...)O and N—H(...)N hydrogen bonds link the mol­ecules into paired ribbons propagated in [100]. The crystal studied was a twin (twin law An external file that holds a picture, illustration, etc.
Object name is e-66-o2691-efi1.jpg00/0An external file that holds a picture, illustration, etc.
Object name is e-66-o2691-efi1.jpg0/001) with a minor component of 25%.

Related literature

For applications of carbonohydrazide derivatives, see: Esmail & Kurzer (1977 [triangle]); Loncle et al. (2004 [triangle]). For a related structure, see: Meyers et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2691-scheme1.jpg

Experimental

Crystal data

  • C9H12N4O
  • M r = 192.23
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2691-efi3.jpg
  • a = 9.7744 (8) Å
  • b = 7.3163 (7) Å
  • c = 28.2761 (3) Å
  • β = 90.796 (1)°
  • V = 2021.9 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.43 × 0.17 × 0.15 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007 [triangle]) T min = 0.963, T max = 0.987
  • 9568 measured reflections
  • 3568 independent reflections
  • 1412 reflections with I > 2σ(I)
  • R int = 0.111

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.186
  • S = 0.84
  • 3568 reflections
  • 256 parameters
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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 I, global. DOI: 10.1107/S1600536810038353/cv2761sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038353/cv2761Isup2.hkl

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

Acknowledgments

This project was supported by the Foundation of Dongchang College, Liaocheng University (grant No. LG0801).

supplementary crystallographic information

Comment

Carbonohydrazide derivatives are popular ligands in coordination chemistry due to the strong coordinative ability (Esmail et al., 1977). Meanwhile, they have also attracted much attention due to interesting bioactivity such as antibacteriale antifungal, anticonvulsant, anticancer activities (Loncle et al., 2004). Herewith we present the crystal structure of the title compound, (I), which is a carbonohydrazide derivative.

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in the reported compound (Meyers et al., 1995). The C=N bond lengths in the molecule are 1.282 (5) °, 1.272 (5)° (C2=N5, C1=N11), respectively, showing the double-bond character. The dihedral angle between the benzene ring (C12—C17) and the plane of C11/N1/N2 is 19.17 (27) °, while the dihedral angle between the benzene ring (C3—C8) and the plane of C2/N5/N6 is 14.87 (31) °.

Intermolecular N—H···O and N—H···N hydrogen bonds (Table 1) link the molecules into paired ribbons propagated in direction [100].

Experimental

Acetophenone (10.0 mmol) and carbohydrazide (10.0 mmol) were mixed in 50 ml flash under sovlent-free condtions. After stirring 2 h at 373 K, the resulting mixture was cooled to room temperature, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C9H12N4O: C 56.24, H 6.29, N 29.15%; found: C 56.13, H 6.24, N 29.31%.

Refinement

All H atoms were placed in geometrically idealized positions (N—H = 0.86–0.90 Å and C—H = 0.93 - 0.96 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.2–1.5 Ueq(C, N).

Figures

Fig. 1.
A view of (I) showing the atomic numbering scheme and 30% probability displacement ellipsoids.

Crystal data

C9H12N4OF(000) = 816
Mr = 192.23Dx = 1.263 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.7744 (8) ÅCell parameters from 839 reflections
b = 7.3163 (7) Åθ = 2.5–26.2°
c = 28.2761 (3) ŵ = 0.09 mm1
β = 90.796 (1)°T = 293 K
V = 2021.9 (3) Å3Block, colourless
Z = 80.43 × 0.17 × 0.15 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer3568 independent reflections
Radiation source: fine-focus sealed tube1412 reflections with I > 2σ(I)
graphiteRint = 0.111
phi and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)h = −10→11
Tmin = 0.963, Tmax = 0.987k = −8→8
9568 measured reflectionsl = −33→23

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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186H-atom parameters constrained
S = 0.84w = 1/[σ2(Fo2) + (0.0777P)2] where P = (Fo2 + 2Fc2)/3
3568 reflections(Δ/σ)max < 0.001
256 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = −0.24 e Å3

Special details

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)

xyzUiso*/Ueq
O10.8472 (3)0.1813 (5)0.45497 (9)0.0877 (10)
O20.3489 (2)0.2384 (4)0.50884 (9)0.0731 (9)
N10.6814 (3)0.3386 (5)0.55616 (12)0.0627 (9)
N20.7850 (3)0.3042 (5)0.52501 (12)0.0655 (10)
H20.86810.33300.53200.079*
N30.6226 (3)0.1926 (5)0.47282 (11)0.0746 (11)
H30.56070.23050.49180.089*
N40.5831 (3)0.0984 (6)0.43144 (11)0.0793 (11)
H4A0.63470.13500.40750.119*
H4C0.5948−0.02100.43600.119*
N50.1757 (3)0.0963 (5)0.40633 (11)0.0578 (9)
N60.2815 (3)0.1455 (5)0.43539 (11)0.0610 (9)
H6A0.36420.14130.42540.073*
N70.1225 (3)0.2228 (5)0.49114 (11)0.0762 (11)
H7A0.08020.11600.48490.091*
N80.0871 (3)0.2698 (6)0.53820 (12)0.0931 (13)
H8A0.11970.18690.55840.140*
H8C0.12390.37820.54480.140*
C10.2557 (4)0.2014 (6)0.48027 (15)0.0612 (11)
C20.2023 (4)0.0482 (5)0.36361 (14)0.0559 (10)
C30.0833 (4)−0.0052 (6)0.33345 (14)0.0583 (11)
C40.0951 (5)−0.0984 (6)0.29212 (15)0.0735 (12)
H40.1824−0.12640.28170.088*
C5−0.0154 (6)−0.1537 (7)0.26486 (17)0.0882 (15)
H5−0.0020−0.21530.23650.106*
C6−0.1446 (6)−0.1168 (8)0.27995 (18)0.0965 (17)
H6−0.2203−0.15740.26260.116*
C7−0.1616 (5)−0.0192 (8)0.32097 (18)0.1011 (17)
H7−0.24940.01100.33060.121*
C8−0.0505 (5)0.0345 (7)0.34802 (15)0.0789 (14)
H8−0.06390.09760.37610.095*
C90.3434 (4)0.0465 (6)0.34318 (14)0.0776 (13)
H9A0.39350.15130.35430.116*
H9B0.33680.04980.30930.116*
H9C0.3903−0.06290.35290.116*
C100.7539 (4)0.2242 (6)0.48324 (16)0.0670 (12)
C110.7111 (4)0.4054 (6)0.59662 (15)0.0609 (11)
C120.5943 (5)0.4406 (6)0.62839 (16)0.0696 (12)
C130.4626 (5)0.4533 (7)0.60913 (17)0.0916 (16)
H130.44960.43930.57670.110*
C140.3502 (6)0.4868 (8)0.6376 (2)0.119 (2)
H140.26310.49440.62410.143*
C150.3676 (7)0.5084 (9)0.6855 (2)0.126 (2)
H150.29260.53260.70450.151*
C160.4968 (8)0.4940 (8)0.7055 (2)0.116 (2)
H160.50930.50490.73810.139*
C170.6091 (6)0.4628 (6)0.67616 (17)0.0891 (15)
H170.69630.45710.68970.107*
C180.8554 (4)0.4505 (6)0.61330 (15)0.0754 (13)
H18A0.90430.33930.61980.113*
H18B0.85170.52300.64160.113*
H18C0.90150.51780.58910.113*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0453 (16)0.145 (3)0.073 (2)0.0036 (17)0.0070 (15)−0.0160 (19)
O20.0450 (15)0.106 (2)0.0682 (19)0.0043 (15)−0.0040 (14)−0.0133 (17)
N10.062 (2)0.070 (3)0.057 (2)0.0059 (18)0.0080 (18)−0.0016 (19)
N20.0499 (19)0.088 (3)0.058 (2)−0.0044 (18)0.0016 (17)−0.012 (2)
N30.044 (2)0.114 (3)0.066 (2)0.0049 (19)0.0020 (16)−0.025 (2)
N40.055 (2)0.115 (3)0.068 (2)0.002 (2)−0.0024 (17)−0.015 (2)
N50.055 (2)0.062 (2)0.056 (2)0.0020 (17)−0.0064 (17)−0.0019 (18)
N60.0501 (19)0.080 (3)0.054 (2)−0.0011 (17)0.0018 (16)−0.0103 (19)
N70.054 (2)0.111 (3)0.064 (2)−0.011 (2)0.0074 (17)−0.020 (2)
N80.056 (2)0.152 (4)0.072 (3)0.002 (2)0.0065 (18)−0.015 (3)
C10.041 (2)0.079 (3)0.064 (3)−0.003 (2)−0.003 (2)−0.002 (2)
C20.061 (3)0.049 (3)0.057 (3)0.000 (2)−0.004 (2)0.001 (2)
C30.071 (3)0.054 (3)0.050 (2)0.002 (2)−0.003 (2)0.006 (2)
C40.087 (3)0.066 (3)0.068 (3)0.004 (3)−0.005 (3)−0.006 (3)
C50.116 (4)0.078 (4)0.069 (3)−0.006 (3)−0.016 (3)−0.010 (3)
C60.105 (4)0.104 (5)0.079 (4)−0.031 (4)−0.027 (3)0.003 (3)
C70.078 (4)0.146 (5)0.079 (4)−0.013 (3)−0.011 (3)−0.004 (4)
C80.071 (3)0.104 (4)0.062 (3)−0.011 (3)−0.009 (2)−0.009 (3)
C90.074 (3)0.092 (4)0.067 (3)−0.001 (3)0.011 (2)−0.009 (3)
C100.050 (3)0.089 (3)0.062 (3)0.009 (2)−0.001 (2)−0.006 (3)
C110.071 (3)0.055 (3)0.057 (3)0.005 (2)0.000 (2)−0.001 (2)
C120.079 (3)0.063 (3)0.067 (3)0.002 (2)0.006 (2)−0.002 (2)
C130.086 (4)0.102 (4)0.088 (4)0.006 (3)0.029 (3)−0.021 (3)
C140.098 (4)0.153 (6)0.106 (4)0.001 (4)0.031 (4)−0.032 (4)
C150.114 (5)0.156 (6)0.109 (5)−0.011 (4)0.052 (4)−0.028 (4)
C160.153 (6)0.122 (5)0.074 (4)−0.010 (5)0.034 (4)−0.016 (3)
C170.119 (4)0.083 (4)0.067 (3)0.009 (3)0.012 (3)−0.005 (3)
C180.078 (3)0.067 (3)0.080 (3)0.007 (2)−0.009 (2)−0.005 (2)

Geometric parameters (Å, °)

O1—C101.260 (4)C5—C61.365 (6)
O2—C11.239 (4)C5—H50.9300
N1—C111.274 (4)C6—C71.374 (7)
N1—N21.374 (4)C6—H60.9300
N2—C101.349 (5)C7—C81.377 (6)
N2—H20.8600C7—H70.9300
N3—C101.333 (5)C8—H80.9300
N3—N41.407 (4)C9—H9A0.9600
N3—H30.8600C9—H9B0.9600
N4—H4A0.8900C9—H9C0.9600
N4—H4C0.8900C11—C121.485 (5)
N5—C21.288 (4)C11—C181.518 (5)
N5—N61.361 (4)C12—C171.366 (5)
N6—C11.360 (5)C12—C131.393 (6)
N6—H6A0.8600C13—C141.393 (6)
N7—C11.351 (4)C13—H130.9300
N7—N81.422 (4)C14—C151.373 (7)
N7—H7A0.9000C14—H140.9300
N8—H8A0.8900C15—C161.380 (8)
N8—H8C0.8900C15—H150.9300
C2—C31.485 (5)C16—C171.404 (7)
C2—C91.503 (5)C16—H160.9300
C3—C41.359 (5)C17—H170.9300
C3—C81.407 (5)C18—H18A0.9600
C4—C51.378 (6)C18—H18B0.9600
C4—H40.9300C18—H18C0.9600
C11—N1—N2119.1 (3)C8—C7—H7119.6
C10—N2—N1118.8 (3)C7—C8—C3120.5 (4)
C10—N2—H2120.6C7—C8—H8119.8
N1—N2—H2120.6C3—C8—H8119.8
C10—N3—N4121.4 (3)C2—C9—H9A109.5
C10—N3—H3119.3C2—C9—H9B109.5
N4—N3—H3119.3H9A—C9—H9B109.5
N3—N4—H4A109.4C2—C9—H9C109.5
N3—N4—H4C109.1H9A—C9—H9C109.5
H4A—N4—H4C109.5H9B—C9—H9C109.5
C2—N5—N6118.5 (3)O1—C10—N3121.3 (4)
C1—N6—N5119.6 (3)O1—C10—N2120.5 (4)
C1—N6—H6A120.2N3—C10—N2118.2 (4)
N5—N6—H6A120.2N1—C11—C12116.3 (4)
C1—N7—N8119.3 (3)N1—C11—C18124.2 (4)
C1—N7—H7A107.2C12—C11—C18119.6 (4)
N8—N7—H7A106.0C17—C12—C13117.6 (4)
N7—N8—H8A110.3C17—C12—C11123.1 (4)
N7—N8—H8C107.9C13—C12—C11119.3 (4)
H8A—N8—H8C109.5C14—C13—C12121.2 (5)
O2—C1—N7121.9 (4)C14—C13—H13119.4
O2—C1—N6122.0 (3)C12—C13—H13119.4
N7—C1—N6116.0 (3)C15—C14—C13120.2 (6)
N5—C2—C3116.4 (4)C15—C14—H14119.9
N5—C2—C9124.1 (3)C13—C14—H14119.9
C3—C2—C9119.5 (4)C14—C15—C16119.7 (5)
C4—C3—C8116.5 (4)C14—C15—H15120.2
C4—C3—C2123.4 (4)C16—C15—H15120.2
C8—C3—C2120.1 (4)C15—C16—C17119.3 (5)
C3—C4—C5123.6 (5)C15—C16—H16120.4
C3—C4—H4118.2C17—C16—H16120.4
C5—C4—H4118.2C12—C17—C16122.0 (5)
C6—C5—C4119.2 (5)C12—C17—H17119.0
C6—C5—H5120.4C16—C17—H17119.0
C4—C5—H5120.4C11—C18—H18A109.5
C5—C6—C7119.3 (5)C11—C18—H18B109.5
C5—C6—H6120.3H18A—C18—H18B109.5
C7—C6—H6120.3C11—C18—H18C109.5
C6—C7—C8120.9 (5)H18A—C18—H18C109.5
C6—C7—H7119.6H18B—C18—H18C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···N8i0.862.192.982 (4)152
N4—H4C···O2ii0.892.293.055 (5)144
N3—H3···O20.862.132.895 (4)148
N6—H6A···N40.862.172.972 (4)156

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2761).

References

  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Esmail, R. & Kurzer, F. (1977). Tetrahedron, 33, 2007–2012.
  • Loncle, C., Brunel, J. M., Vidal, N., Dherbomez, M. & Letourneux, Y. (2004). Eur. J. Med. Chem.39, 1067–1071. [PubMed]
  • Meyers, C. Y., Kolb, V. M. & Robinson, P. D. (1995). Acta Cryst. C51, 775–777.
  • Sheldrick, G. M. (2007). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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