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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o94.
Published online 2009 December 9. doi:  10.1107/S1600536809052143
PMCID: PMC2980044

N′-Cyclo­hexyl­idenebenzohydrazide

Abstract

In the title compound, C13H16N2O, the cyclo­hexane ring adopts a chair conformation. In the crystal structure, inter­molecular N—H(...)O and C—H(...)O hydrogen bonds link the mol­ecules into chains propagating in [001].

Related literature

For related structures, see: Fun et al. (2008 [triangle]); Nie (2008 [triangle]); Kong et al. (2009 [triangle]); Fan & Song (2009 [triangle]).

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Object name is e-66-00o94-scheme1.jpg

Experimental

Crystal data

  • C13H16N2O
  • M r = 216.28
  • Tetragonal, An external file that holds a picture, illustration, etc.
Object name is e-66-00o94-efi1.jpg
  • a = 9.4691 (11) Å
  • c = 13.8514 (15) Å
  • V = 1242.0 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 298 K
  • 0.44 × 0.41 × 0.28 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.968, T max = 0.980
  • 6248 measured reflections
  • 1145 independent reflections
  • 860 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.114
  • S = 1.08
  • 1145 reflections
  • 145 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.12 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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/S1600536809052143/cv2665sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052143/cv2665Isup2.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

In continuation of our structural study of benzohydrazide derivatives (Kong et al., 2009; Fan & Song, 2009), we present here the title compound, (I).

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in the analogue compounds (Nie, 2008; Fun et al., 2008). The C8=N2 bond length is 1.283 (4) ° showing the double-bond character. The dihedral angle between the benzene ring C2—C7 and the plane C1/N1/N2 is 19.0 (3) °

In the crystal structure, intermolecular N—H···O and C—H..O hydrogen bonds (Table 1) link the molecules into chains propagated in direction [001].

Experimental

Cyclohexanone (5 mmol), benzohydrazide (5 mmol) and 10 ml of methanol were mixed in 50 ml flask. After stirring for 30 min at 373 K, the resulting mixture was recrystallized from methanol, affording the title compound as colourless crystalline solid. Elemental analysis: calculated for C13H16N2O: C 72.19, H 7.46, N 12.95%; found: C 72.18, H 7.25, N 12.78%.

Refinement

All H atoms were placed in geometrically idealized positions (N—H 0.86 Å, C—H 0.93–0.97 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.2 Ueq(C, N). In the absence of any significant anomalous scatterers in the molecule, the 1021 Friedel pairs were merged before the final refinement.

Figures

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

Crystal data

C13H16N2ODx = 1.157 Mg m3
Mr = 216.28Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43Cell parameters from 1861 reflections
a = 9.4691 (11) Åθ = 2.6–21.7°
c = 13.8514 (15) ŵ = 0.07 mm1
V = 1242.0 (2) Å3T = 298 K
Z = 4Block, colourless
F(000) = 4640.44 × 0.41 × 0.28 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer1145 independent reflections
Radiation source: fine-focus sealed tube860 reflections with I > 2σ(I)
graphiteRint = 0.039
phi and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→11
Tmin = 0.968, Tmax = 0.980k = −9→11
6248 measured reflectionsl = −16→15

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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0557P)2 + 0.1344P] where P = (Fo2 + 2Fc2)/3
1145 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.12 e Å3
1 restraintΔρmin = −0.13 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
N10.1658 (3)0.0240 (3)0.0959 (2)0.0539 (7)
H10.1939−0.02920.14230.065*
N20.0942 (3)−0.0310 (3)0.0148 (2)0.0591 (8)
O10.1613 (3)0.2405 (2)0.02619 (18)0.0664 (7)
C10.1877 (3)0.1650 (3)0.0965 (2)0.0469 (7)
C20.2512 (3)0.2288 (3)0.1861 (2)0.0476 (8)
C30.2322 (4)0.3730 (4)0.1997 (3)0.0691 (10)
H30.17850.42440.15580.083*
C40.2925 (5)0.4407 (5)0.2780 (4)0.0879 (14)
H40.28000.53740.28600.106*
C50.3704 (5)0.3662 (5)0.3435 (3)0.0850 (13)
H50.40900.41200.39670.102*
C60.3921 (5)0.2236 (5)0.3311 (3)0.0837 (13)
H60.44680.17330.37510.100*
C70.3317 (4)0.1553 (4)0.2525 (3)0.0660 (10)
H70.34560.05880.24440.079*
C80.0953 (3)−0.1653 (4)0.0023 (3)0.0571 (9)
C90.0175 (4)−0.2201 (4)−0.0853 (3)0.0760 (12)
H9A−0.0581−0.2823−0.06480.091*
H9B−0.0242−0.1415−0.12000.091*
C100.1162 (5)−0.2993 (5)−0.1514 (4)0.0919 (14)
H10A0.1828−0.2336−0.18000.110*
H10B0.0622−0.3421−0.20320.110*
C110.1973 (5)−0.4143 (5)−0.0971 (4)0.0898 (14)
H11A0.1320−0.4873−0.07670.108*
H11B0.2659−0.4570−0.14010.108*
C120.2727 (5)−0.3556 (4)−0.0097 (3)0.0824 (13)
H12A0.3473−0.2927−0.03100.099*
H12B0.3162−0.43270.02550.099*
C130.1736 (5)−0.2748 (4)0.0584 (3)0.0719 (11)
H13A0.1073−0.33970.08800.086*
H13B0.2280−0.23010.10930.086*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0677 (17)0.0506 (16)0.0435 (16)−0.0033 (12)−0.0078 (14)0.0016 (13)
N20.0676 (18)0.0586 (17)0.0510 (18)−0.0012 (14)−0.0130 (14)−0.0043 (15)
O10.0879 (17)0.0622 (14)0.0491 (16)−0.0017 (12)−0.0084 (13)0.0105 (13)
C10.0479 (17)0.0524 (19)0.040 (2)0.0022 (14)0.0066 (15)0.0005 (16)
C20.0538 (18)0.0502 (18)0.0389 (19)−0.0028 (15)0.0075 (15)−0.0034 (15)
C30.084 (3)0.059 (2)0.065 (3)0.0076 (18)0.001 (2)−0.0094 (19)
C40.106 (3)0.066 (3)0.092 (4)0.001 (2)0.005 (3)−0.029 (3)
C50.102 (3)0.097 (3)0.056 (3)−0.016 (3)−0.003 (3)−0.024 (3)
C60.102 (3)0.087 (3)0.061 (3)−0.008 (2)−0.023 (2)−0.006 (2)
C70.077 (2)0.063 (2)0.058 (2)−0.0037 (19)−0.011 (2)−0.0024 (19)
C80.063 (2)0.055 (2)0.053 (2)−0.0060 (16)0.0021 (17)−0.0048 (17)
C90.083 (3)0.069 (2)0.076 (3)−0.009 (2)−0.020 (2)−0.013 (2)
C100.123 (4)0.090 (3)0.062 (3)−0.016 (3)−0.009 (3)−0.022 (3)
C110.103 (3)0.079 (3)0.088 (4)−0.005 (2)0.020 (3)−0.024 (3)
C120.089 (3)0.072 (2)0.086 (3)0.009 (2)0.005 (3)−0.006 (2)
C130.097 (3)0.064 (2)0.055 (2)0.006 (2)0.000 (2)0.0009 (19)

Geometric parameters (Å, °)

N1—C11.350 (4)C8—C131.493 (5)
N1—N21.412 (4)C8—C91.511 (5)
N1—H10.8600C9—C101.508 (6)
N2—C81.283 (4)C9—H9A0.9700
O1—C11.234 (4)C9—H9B0.9700
C1—C21.506 (4)C10—C111.530 (7)
C2—C71.382 (5)C10—H10A0.9700
C2—C31.390 (4)C10—H10B0.9700
C3—C41.383 (6)C11—C121.511 (6)
C3—H30.9300C11—H11A0.9700
C4—C51.366 (7)C11—H11B0.9700
C4—H40.9300C12—C131.535 (5)
C5—C61.377 (6)C12—H12A0.9700
C5—H50.9300C12—H12B0.9700
C6—C71.390 (5)C13—H13A0.9700
C6—H60.9300C13—H13B0.9700
C7—H70.9300
C1—N1—N2116.3 (3)C10—C9—H9A109.5
C1—N1—H1121.8C8—C9—H9A109.5
N2—N1—H1121.8C10—C9—H9B109.5
C8—N2—N1118.0 (3)C8—C9—H9B109.5
O1—C1—N1122.5 (3)H9A—C9—H9B108.0
O1—C1—C2119.9 (3)C9—C10—C11111.5 (4)
N1—C1—C2117.6 (3)C9—C10—H10A109.3
C7—C2—C3118.4 (3)C11—C10—H10A109.3
C7—C2—C1124.5 (3)C9—C10—H10B109.3
C3—C2—C1117.0 (3)C11—C10—H10B109.3
C4—C3—C2120.5 (4)H10A—C10—H10B108.0
C4—C3—H3119.7C12—C11—C10111.7 (4)
C2—C3—H3119.7C12—C11—H11A109.3
C5—C4—C3120.3 (4)C10—C11—H11A109.3
C5—C4—H4119.9C12—C11—H11B109.3
C3—C4—H4119.9C10—C11—H11B109.3
C4—C5—C6120.3 (4)H11A—C11—H11B107.9
C4—C5—H5119.8C11—C12—C13112.8 (3)
C6—C5—H5119.8C11—C12—H12A109.0
C5—C6—C7119.5 (4)C13—C12—H12A109.0
C5—C6—H6120.3C11—C12—H12B109.0
C7—C6—H6120.3C13—C12—H12B109.0
C2—C7—C6120.9 (4)H12A—C12—H12B107.8
C2—C7—H7119.5C8—C13—C12109.2 (3)
C6—C7—H7119.5C8—C13—H13A109.8
N2—C8—C13128.4 (3)C12—C13—H13A109.8
N2—C8—C9116.4 (3)C8—C13—H13B109.8
C13—C8—C9114.9 (3)C12—C13—H13B109.8
C10—C9—C8110.9 (3)H13A—C13—H13B108.3

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.283.133 (4)172
C13—H13B···O1i0.972.413.264 (5)147
C7—H7···O1i0.932.353.137 (5)142

Symmetry codes: (i) y, −x, z+1/4.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2665).

References

  • Fan, C.-G. & Song, M.-Z. (2009). Acta Cryst. E65, o2679. [PMC free article] [PubMed]
  • Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594–o1595. [PMC free article] [PubMed]
  • Kong, L.-Q., Ju, X.-P. & Li, D.-C. (2009). Acta Cryst. E65, m1251. [PMC free article] [PubMed]
  • Nie, Y. (2008). Acta Cryst. E64, o471. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Systems, Inc., Madison, Wisconsin, USA.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography