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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2679.
Published online 2009 October 10. doi:  10.1107/S1600536809040331
PMCID: PMC2971129

N′-(2-Chloro­benzyl­idene)benzo­hydrazide

Abstract

The asymmetric unit of the title compound, C14H11ClN2O, contains two independent mol­ecules. In one mol­ecule, the two aromatic rings form a dihedral angle of 45.94 (16)°, while in the second mol­ecule this angle is 58.48 (16)°. In the crystal, inter­molecular N—H(...)O hydrogen bonds link the mol­ecules into two crystallographically independent sets of chains propagating along [001].

Related literature

For the biological properties of Schiff base ligands, see: Bedia et al. (2006 [triangle]). For related crystal structures, see: Fun et al. (2008 [triangle]); Alhadi et al. (2008 [triangle]); Nie (2008 [triangle]).

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Object name is e-65-o2679-scheme1.jpg

Experimental

Crystal data

  • C14H11ClN2O
  • M r = 258.70
  • Tetragonal, An external file that holds a picture, illustration, etc.
Object name is e-65-o2679-efi1.jpg
  • a = 13.5588 (17) Å
  • c = 14.3993 (18) Å
  • V = 2647.2 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 298 K
  • 0.45 × 0.42 × 0.38 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.885, T max = 0.902
  • 10838 measured reflections
  • 4614 independent reflections
  • 2766 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.093
  • S = 1.03
  • 4614 reflections
  • 325 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.23 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2105 Friedel pairs
  • Flack parameter: −0.03 (7)

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/S1600536809040331/cv2620sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040331/cv2620Isup2.hkl

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

Acknowledgments

The authors acknowledge the financial support of the Foundation of Binzhou University (grant No. BZXYLG200609).

supplementary crystallographic information

Comment

Schiff base ligands have received considerable attention during the last decades, mainly because of diversity of their structures and biological properties (Bedia et al., 2006). We report here the crystal structure of the title new Schiff base compound (I).

In (I) (Fig. 1), the bond lengths and angles are normal and comparable with those observed in similar compounds (Nie et al., 2008; Fun et al., 2008; Alhadi et al., 2008). The asymmetric unit of (I) contains two independent molecules- A and B, respectively. In molecule A, two aromatic rings form a dihedral angle of 45.94 (16)°, while in molecule B this angle is 58.48 (16) °.

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

Experimental

Benzohydrazide (5.0 mmol), ethanol (20 ml) and 2-chlorobenzaldehyde (5.0 mmol) were mixed in 50 ml flash. After refluxing for 3 h, 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 C14H11ClN2O: C 65.00, H 4.29, N 10.83%; found: C 65.13, H 4.36, N 10.74%.

Refinement

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

Figures

Fig. 1.
The content of asymmetric unit of the title compound showing the atomic numbering scheme and 30% probability displacement ellipsoids.

Crystal data

C14H11ClN2ODx = 1.298 Mg m3
Mr = 258.70Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41Cell parameters from 2946 reflections
a = 13.5588 (17) Åθ = 2.6–25.3°
c = 14.3993 (18) ŵ = 0.28 mm1
V = 2647.2 (6) Å3T = 298 K
Z = 8Needle, colourless
F(000) = 10720.45 × 0.42 × 0.38 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer4614 independent reflections
Radiation source: fine-focus sealed tube2766 reflections with I > 2σ(I)
graphiteRint = 0.043
[var phi] and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→16
Tmin = 0.885, Tmax = 0.902k = −6→16
10838 measured reflectionsl = −16→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.093w = 1/[σ2(Fo2) + (0.0242P)2 + 0.8271P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4614 reflectionsΔρmax = 0.21 e Å3
325 parametersΔρmin = −0.23 e Å3
1 restraintAbsolute structure: Flack (1983), 2105 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.03 (7)

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
Cl10.75607 (8)0.65234 (7)0.24623 (8)0.0633 (3)
Cl20.88744 (9)−0.28276 (9)0.02864 (13)0.1075 (6)
N10.4131 (2)0.5479 (2)0.3296 (2)0.0408 (8)
H10.41390.58290.27980.049*
N20.4972 (2)0.53797 (19)0.3835 (2)0.0405 (8)
N30.9519 (2)0.0803 (2)0.0223 (2)0.0495 (9)
H30.91120.07000.06700.059*
N41.0075 (2)0.0039 (2)−0.0142 (2)0.0494 (8)
O10.32675 (18)0.44465 (18)0.42320 (19)0.0536 (7)
O21.00890 (19)0.18599 (17)−0.0864 (2)0.0543 (7)
C10.3299 (3)0.5015 (3)0.3567 (3)0.0402 (9)
C20.2392 (2)0.5252 (3)0.3029 (3)0.0418 (9)
C30.1631 (3)0.4574 (3)0.3042 (3)0.0642 (13)
H3A0.17080.39790.33540.077*
C40.0752 (3)0.4782 (4)0.2591 (3)0.0827 (15)
H40.02500.43140.25770.099*
C50.0623 (3)0.5671 (4)0.2167 (4)0.0843 (16)
H50.00220.58190.18880.101*
C60.1368 (3)0.6345 (4)0.2148 (3)0.0742 (14)
H60.12780.69440.18450.089*
C70.2262 (3)0.6142 (3)0.2578 (3)0.0542 (10)
H70.27700.66020.25640.065*
C80.5738 (3)0.5796 (3)0.3501 (3)0.0425 (9)
H80.57040.61020.29240.051*
C90.6667 (2)0.5797 (2)0.4014 (3)0.0399 (9)
C100.7535 (3)0.6149 (2)0.3604 (3)0.0411 (9)
C110.8398 (3)0.6218 (3)0.4122 (3)0.0536 (11)
H110.89710.64580.38480.064*
C120.8404 (3)0.5931 (3)0.5037 (4)0.0599 (11)
H120.89800.59860.53830.072*
C130.7562 (3)0.5561 (3)0.5445 (3)0.0551 (11)
H130.75710.53510.60600.066*
C140.6715 (3)0.5508 (3)0.4937 (3)0.0485 (10)
H140.61470.52680.52200.058*
C150.9631 (2)0.1712 (3)−0.0140 (3)0.0429 (9)
C160.9164 (2)0.2533 (2)0.0384 (3)0.0382 (9)
C170.8908 (3)0.2462 (3)0.1306 (3)0.0509 (11)
H170.90090.18730.16230.061*
C180.8502 (3)0.3259 (3)0.1762 (3)0.0638 (13)
H180.83290.32070.23850.077*
C190.8352 (3)0.4131 (3)0.1296 (4)0.0666 (14)
H190.80800.46680.16050.080*
C200.8601 (3)0.4213 (3)0.0382 (4)0.0624 (13)
H200.84990.48050.00700.075*
C210.9006 (2)0.3416 (3)−0.0083 (3)0.0481 (10)
H210.91720.3471−0.07080.058*
C220.9846 (3)−0.0815 (3)0.0139 (3)0.0517 (11)
H220.9300−0.08980.05210.062*
C231.0434 (3)−0.1671 (3)−0.0132 (3)0.0534 (11)
C241.0065 (3)−0.2622 (3)−0.0086 (3)0.0586 (11)
C251.0630 (4)−0.3424 (3)−0.0335 (3)0.0702 (14)
H251.0364−0.4055−0.03000.084*
C261.1573 (4)−0.3296 (3)−0.0630 (3)0.0798 (15)
H261.1956−0.3839−0.07910.096*
C271.1960 (4)−0.2360 (4)−0.0689 (4)0.0951 (19)
H271.2604−0.2270−0.08960.114*
C281.1396 (3)−0.1556 (3)−0.0444 (4)0.0887 (18)
H281.1664−0.0926−0.04870.106*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0684 (7)0.0568 (6)0.0646 (7)−0.0023 (5)0.0190 (6)0.0062 (6)
Cl20.0785 (9)0.0592 (8)0.1849 (18)−0.0126 (7)0.0274 (10)0.0013 (9)
N10.0326 (18)0.049 (2)0.041 (2)−0.0026 (15)−0.0042 (15)0.0040 (15)
N20.0316 (17)0.0436 (18)0.046 (2)−0.0003 (15)−0.0021 (16)−0.0020 (15)
N30.053 (2)0.0354 (18)0.060 (2)0.0021 (15)0.0208 (17)−0.0004 (16)
N40.0535 (19)0.0383 (18)0.057 (2)0.0034 (16)0.0091 (17)−0.0023 (17)
O10.0470 (16)0.0590 (18)0.055 (2)−0.0098 (13)−0.0089 (13)0.0145 (15)
O20.0614 (18)0.0442 (16)0.0573 (19)−0.0025 (14)0.0186 (16)0.0003 (14)
C10.042 (2)0.038 (2)0.040 (2)−0.0029 (18)−0.0036 (19)0.0017 (19)
C20.033 (2)0.052 (2)0.040 (2)−0.0049 (19)−0.0028 (18)−0.0031 (19)
C30.049 (3)0.079 (3)0.065 (3)−0.018 (2)−0.010 (2)0.011 (3)
C40.049 (3)0.125 (4)0.074 (4)−0.029 (3)−0.015 (3)0.012 (3)
C50.039 (3)0.140 (5)0.073 (4)0.008 (3)−0.010 (2)0.011 (4)
C60.062 (3)0.089 (4)0.071 (4)0.017 (3)−0.009 (3)0.013 (3)
C70.042 (2)0.066 (3)0.054 (3)0.003 (2)−0.002 (2)0.003 (2)
C80.043 (2)0.043 (2)0.041 (2)0.0016 (19)0.0004 (19)0.0003 (19)
C90.033 (2)0.034 (2)0.052 (3)−0.0017 (17)0.0039 (19)−0.0032 (19)
C100.047 (2)0.030 (2)0.047 (3)−0.0011 (18)0.010 (2)−0.0036 (18)
C110.040 (2)0.041 (2)0.080 (4)−0.0033 (18)0.006 (2)−0.006 (2)
C120.045 (3)0.059 (3)0.076 (4)−0.002 (2)−0.009 (3)−0.006 (3)
C130.044 (3)0.067 (3)0.054 (3)0.000 (2)−0.004 (2)0.004 (2)
C140.038 (2)0.053 (2)0.054 (3)−0.0016 (18)−0.001 (2)0.005 (2)
C150.035 (2)0.038 (2)0.056 (3)−0.0038 (17)0.002 (2)−0.002 (2)
C160.032 (2)0.033 (2)0.050 (3)−0.0007 (16)0.0021 (17)−0.0049 (19)
C170.047 (2)0.048 (2)0.058 (3)0.003 (2)−0.001 (2)−0.003 (2)
C180.066 (3)0.063 (3)0.062 (3)0.000 (3)0.008 (2)−0.022 (3)
C190.054 (3)0.056 (3)0.090 (4)0.005 (2)−0.002 (3)−0.027 (3)
C200.053 (3)0.036 (2)0.098 (4)0.003 (2)−0.016 (3)−0.001 (3)
C210.043 (2)0.038 (2)0.063 (3)−0.0031 (18)−0.001 (2)−0.001 (2)
C220.054 (2)0.039 (2)0.062 (3)0.001 (2)0.017 (2)−0.001 (2)
C230.057 (3)0.044 (3)0.059 (3)0.010 (2)0.012 (2)0.006 (2)
C240.068 (3)0.041 (2)0.067 (3)0.003 (2)0.005 (3)−0.001 (2)
C250.091 (4)0.048 (3)0.072 (4)0.015 (3)0.003 (3)−0.002 (2)
C260.100 (4)0.059 (3)0.081 (4)0.034 (3)0.017 (3)0.006 (3)
C270.086 (4)0.070 (4)0.130 (5)0.017 (3)0.047 (4)0.015 (3)
C280.076 (3)0.055 (3)0.136 (5)0.006 (3)0.043 (3)0.012 (3)

Geometric parameters (Å, °)

Cl1—C101.721 (4)C11—H110.9300
Cl2—C241.724 (4)C12—C131.379 (5)
N1—C11.350 (4)C12—H120.9300
N1—N21.386 (4)C13—C141.364 (5)
N1—H10.8600C13—H130.9300
N2—C81.277 (4)C14—H140.9300
N3—C151.347 (4)C15—C161.487 (5)
N3—N41.385 (4)C16—C171.375 (5)
N3—H30.8600C16—C211.389 (5)
N4—C221.264 (4)C17—C181.379 (5)
O1—C11.230 (4)C17—H170.9300
O2—C151.230 (4)C18—C191.375 (6)
C1—C21.488 (5)C18—H180.9300
C2—C31.382 (5)C19—C201.364 (6)
C2—C71.381 (5)C19—H190.9300
C3—C41.387 (5)C20—C211.385 (5)
C3—H3A0.9300C20—H200.9300
C4—C51.362 (6)C21—H210.9300
C4—H40.9300C22—C231.461 (5)
C5—C61.362 (6)C22—H220.9300
C5—H50.9300C23—C241.385 (5)
C6—C71.389 (5)C23—C281.388 (5)
C6—H60.9300C24—C251.376 (5)
C7—H70.9300C25—C261.359 (6)
C8—C91.459 (5)C25—H250.9300
C8—H80.9300C26—C271.376 (6)
C9—C141.388 (5)C26—H260.9300
C9—C101.400 (5)C27—C281.378 (6)
C10—C111.390 (5)C27—H270.9300
C11—C121.374 (6)C28—H280.9300
C1—N1—N2118.7 (3)C12—C13—H13120.4
C1—N1—H1120.6C13—C14—C9122.6 (4)
N2—N1—H1120.6C13—C14—H14118.7
C8—N2—N1114.5 (3)C9—C14—H14118.7
C15—N3—N4118.4 (3)O2—C15—N3122.4 (3)
C15—N3—H3120.8O2—C15—C16121.5 (3)
N4—N3—H3120.8N3—C15—C16116.1 (4)
C22—N4—N3115.5 (3)C17—C16—C21119.3 (4)
O1—C1—N1123.1 (3)C17—C16—C15123.0 (3)
O1—C1—C2120.8 (3)C21—C16—C15117.7 (4)
N1—C1—C2116.1 (3)C16—C17—C18120.3 (4)
C3—C2—C7119.4 (3)C16—C17—H17119.8
C3—C2—C1117.8 (3)C18—C17—H17119.8
C7—C2—C1122.6 (3)C19—C18—C17120.0 (5)
C2—C3—C4120.0 (4)C19—C18—H18120.0
C2—C3—H3A120.0C17—C18—H18120.0
C4—C3—H3A120.0C20—C19—C18120.3 (4)
C5—C4—C3120.0 (4)C20—C19—H19119.9
C5—C4—H4120.0C18—C19—H19119.9
C3—C4—H4120.0C19—C20—C21120.1 (4)
C6—C5—C4120.5 (4)C19—C20—H20120.0
C6—C5—H5119.8C21—C20—H20120.0
C4—C5—H5119.8C20—C21—C16120.0 (4)
C5—C6—C7120.3 (5)C20—C21—H21120.0
C5—C6—H6119.8C16—C21—H21120.0
C7—C6—H6119.8N4—C22—C23120.5 (4)
C2—C7—C6119.6 (4)N4—C22—H22119.7
C2—C7—H7120.2C23—C22—H22119.7
C6—C7—H7120.2C24—C23—C28117.4 (4)
N2—C8—C9120.8 (3)C24—C23—C22122.0 (4)
N2—C8—H8119.6C28—C23—C22120.6 (4)
C9—C8—H8119.6C25—C24—C23121.5 (4)
C14—C9—C10117.4 (3)C25—C24—Cl2118.3 (3)
C14—C9—C8121.7 (3)C23—C24—Cl2120.2 (3)
C10—C9—C8120.8 (4)C26—C25—C24120.3 (4)
C11—C10—C9120.3 (4)C26—C25—H25119.9
C11—C10—Cl1118.4 (3)C24—C25—H25119.9
C9—C10—Cl1121.3 (3)C25—C26—C27119.7 (4)
C12—C11—C10120.0 (4)C25—C26—H26120.1
C12—C11—H11120.0C27—C26—H26120.1
C10—C11—H11120.0C26—C27—C28120.2 (5)
C11—C12—C13120.5 (4)C26—C27—H27119.9
C11—C12—H12119.8C28—C27—H27119.9
C13—C12—H12119.8C27—C28—C23121.0 (4)
C14—C13—C12119.2 (4)C27—C28—H28119.5
C14—C13—H13120.4C23—C28—H28119.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.012.854 (4)168
N3—H3···O2ii0.862.092.928 (4)166

Symmetry codes: (i) y, −x+1, z−1/4; (ii) −y+1, x−1, z+1/4.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2620).

References

  • Alhadi, A. A., Ali, H. M., Puvaneswary, S., Robinson, W. T. & Ng, S. W. (2008). Acta Cryst. E64, o1584. [PMC free article] [PubMed]
  • Bedia, K. K., Elcin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem.41, 1253–1261. [PubMed]
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594–o1595. [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 Instruments Inc., Madison, Wisconsin, USA.

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