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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1759.
Published online 2008 August 16. doi:  10.1107/S1600536808025828
PMCID: PMC2960590

4-Chloro-N′-(2-hydr­oxy-1-naphthyl­idene)benzohydrazide

Abstract

The mol­ecule of the title compound, C18H13ClN2O2, displays a trans configuration with respect to the C=N double bond. The dihedral angle between the benzene and naphthyl ring systems is 6.0 (2)°. An O—H(...)N hydrogen bond is observed in the mol­ecular structure. In the crystal structure, mol­ecules are linked through inter­molecular N—H(...)O hydrogen bonds and π–π stacking inter­actions [centroid–centroid distance = 3.603 (2) Å], forming chains running along the b axis.

Related literature

For related structures, see: Yang (2006a [triangle],b [triangle],c [triangle],d [triangle],e [triangle], 2007a [triangle],b [triangle],c [triangle]); Yang & Guo (2006 [triangle]). For related literature, see: Bernardo et al. (1996 [triangle]); Musie et al. (2001 [triangle]); Paul et al. (2002 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1759-scheme1.jpg

Experimental

Crystal data

  • C18H13ClN2O2
  • M r = 324.75
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1759-efi1.jpg
  • a = 6.200 (3) Å
  • b = 4.788 (2) Å
  • c = 25.320 (11) Å
  • β = 95.844 (7)°
  • V = 747.8 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 298 (2) K
  • 0.23 × 0.21 × 0.20 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.941, T max = 0.949
  • 4001 measured reflections
  • 2197 independent reflections
  • 2039 reflections with I > 2σ(I)
  • R int = 0.017

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.080
  • S = 1.05
  • 2197 reflections
  • 212 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.12 e Å−3
  • Δρmin = −0.19 e Å−3
  • Absolute structure: Flack (1983 [triangle]), with 596 Friedel pairs
  • Flack parameter: 0.03 (7)

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025828/ci2654sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025828/ci2654Isup2.hkl

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

Acknowledgments

The author acknowledges Key Laboratory Construction Support from the Education Office of Shanxi Province (Project No. 05JS43).

supplementary crystallographic information

Comment

Schiff base compounds have been of great interest for a long time. These compounds play an important role in the development of coordination chemistry (Musie et al., 2001; Bernardo et al., 1996; Paul et al., 2002). Recently, we have reported crystal structures of a few Schiff base compounds (Yang, 2006a,b,c,d,e, 2007a,b,c; Yang & Guo, 2006). As a further investigation of this work, the crystal structure of the title compound is reported here.

The molecule of the title compound displays a trans configuration with respect to the C═N double bond (Fig. 1). The dihedral angle between the benzene and naphthyl rings is 6.0 (2)°. All the bond lengths are within normal ranges (Allen et al., 1987). The C11═N1 bond length of 1.275 (3) Å conforms to the value for a double bond. The bond length of 1.353 (3) Å between atoms C12 and N2 is intermediate between an N—N single bond and an N═N double bond, because of conjugation effects in the molecule. An intramolecular O—H···N hydrogen bond is observed.

In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains running along the b axis (Fig. 2). The chain is strengthened by π–π interactions between C1–C5/C10 and C5–C10 benzene rings (centroid–centroid distance is 3.603 (2) Å).

Experimental

2-Hydroxy-1-naphthylaldehyde (0.1 mmol, 17.2 mg) and 4-chlorobenzohydrazide (0.1 mmol, 17.0 mg) were dissolved in methanol (10 ml). The mixture was stirred at room temperature to give a clear colourless solution. Single crystals of the title compound were obtained by gradual evaporation of the solvent over a period of 8 d at room temperature.

Refinement

Atom H2 was located in a difference Fourier map and refined isotropically, with the N—H distance restrained to 0.90 (1) Å. Other H atoms were placed in idealized positions and constrained to ride on their parent atoms, with O—H = 0.82 Å, C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Crystal packing packing of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

Crystal data

C18H13ClN2O2F000 = 336
Mr = 324.75Dx = 1.442 Mg m3
Monoclinic, PcMo Kα radiation λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 2145 reflections
a = 6.200 (3) Åθ = 2.8–29.3º
b = 4.788 (2) ŵ = 0.27 mm1
c = 25.320 (11) ÅT = 298 (2) K
β = 95.844 (7)ºBlock, colourless
V = 747.8 (6) Å30.23 × 0.21 × 0.20 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer2197 independent reflections
Radiation source: fine-focus sealed tube2039 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.017
T = 298(2) Kθmax = 27.0º
ω scansθmin = 3.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −5→7
Tmin = 0.941, Tmax = 0.949k = −6→6
4001 measured reflectionsl = −31→26

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.032  w = 1/[σ2(Fo2) + (0.0403P)2 + 0.1026P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.080(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.12 e Å3
2197 reflectionsΔρmin = −0.19 e Å3
212 parametersExtinction correction: none
3 restraintsAbsolute structure: Flack (1983), with 596 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.03 (7)
Secondary atom site location: difference Fourier map

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
Cl11.44733 (12)0.28331 (19)0.25960 (4)0.0780 (3)
N10.3640 (3)0.4990 (4)0.05683 (7)0.0395 (4)
N20.5480 (3)0.4210 (4)0.08892 (8)0.0390 (4)
O10.0022 (3)0.7705 (3)0.04417 (7)0.0512 (4)
H10.12200.72930.05890.077*
O20.5730 (3)0.8546 (3)0.12464 (7)0.0504 (4)
C10.0931 (3)0.3955 (4)−0.01348 (9)0.0378 (5)
C2−0.0450 (3)0.6040 (4)0.00131 (9)0.0404 (5)
C3−0.2478 (4)0.6510 (5)−0.02775 (11)0.0515 (6)
H3−0.34130.7847−0.01630.062*
C4−0.3071 (4)0.5020 (5)−0.07244 (11)0.0529 (6)
H4−0.44220.5341−0.09090.063*
C5−0.1684 (4)0.2987 (5)−0.09167 (10)0.0458 (5)
C6−0.2251 (4)0.1535 (5)−0.13960 (10)0.0544 (6)
H6−0.35800.1895−0.15890.065*
C7−0.0893 (5)−0.0380 (6)−0.15817 (10)0.0587 (7)
H7−0.1289−0.1318−0.18980.070*
C80.1105 (5)−0.0923 (6)−0.12918 (10)0.0549 (6)
H80.2035−0.2233−0.14180.066*
C90.1709 (4)0.0441 (5)−0.08267 (9)0.0478 (6)
H90.30510.0049−0.06430.057*
C100.0348 (3)0.2428 (5)−0.06184 (9)0.0384 (5)
C110.2922 (3)0.3316 (5)0.01999 (9)0.0393 (5)
H110.36730.16780.01450.047*
C120.6429 (3)0.6152 (4)0.12246 (8)0.0371 (5)
C130.8398 (3)0.5189 (4)0.15662 (8)0.0357 (4)
C140.8939 (4)0.6535 (5)0.20461 (10)0.0468 (6)
H140.80450.79410.21530.056*
C151.0795 (4)0.5809 (6)0.23675 (10)0.0532 (6)
H151.11550.67010.26910.064*
C161.2100 (4)0.3728 (5)0.21960 (9)0.0483 (6)
C171.1626 (4)0.2370 (5)0.17207 (10)0.0449 (5)
H171.25430.09910.16130.054*
C180.9751 (3)0.3101 (4)0.14053 (9)0.0407 (5)
H180.93930.21890.10840.049*
H20.576 (6)0.240 (3)0.0963 (14)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0468 (3)0.1144 (6)0.0692 (4)0.0089 (4)−0.0112 (3)0.0192 (4)
N10.0344 (9)0.0357 (9)0.0476 (10)0.0038 (7)0.0003 (8)0.0045 (7)
N20.0373 (9)0.0305 (8)0.0475 (10)0.0053 (8)−0.0031 (8)0.0022 (7)
O10.0545 (10)0.0446 (9)0.0552 (10)0.0141 (8)0.0086 (8)0.0030 (8)
O20.0490 (9)0.0290 (7)0.0715 (11)0.0077 (7)−0.0016 (8)−0.0015 (7)
C10.0326 (11)0.0347 (10)0.0460 (12)0.0008 (9)0.0040 (9)0.0108 (9)
C20.0382 (12)0.0373 (12)0.0465 (12)0.0038 (9)0.0086 (9)0.0103 (9)
C30.0400 (12)0.0496 (14)0.0662 (16)0.0121 (11)0.0114 (11)0.0140 (12)
C40.0336 (12)0.0531 (14)0.0700 (17)0.0073 (10)−0.0036 (11)0.0165 (12)
C50.0367 (12)0.0431 (12)0.0561 (14)−0.0036 (10)−0.0017 (10)0.0164 (10)
C60.0490 (14)0.0546 (15)0.0558 (15)−0.0049 (12)−0.0129 (11)0.0132 (12)
C70.0672 (17)0.0599 (16)0.0468 (15)−0.0122 (14)−0.0056 (12)0.0016 (12)
C80.0576 (14)0.0563 (15)0.0507 (15)0.0031 (12)0.0050 (11)−0.0020 (12)
C90.0427 (13)0.0486 (13)0.0512 (14)0.0048 (10)0.0008 (10)0.0022 (10)
C100.0330 (10)0.0350 (12)0.0466 (12)−0.0017 (8)0.0014 (8)0.0102 (8)
C110.0345 (11)0.0343 (10)0.0491 (12)0.0053 (8)0.0038 (9)0.0047 (9)
C120.0367 (11)0.0311 (10)0.0439 (12)0.0030 (9)0.0059 (9)0.0046 (8)
C130.0371 (11)0.0283 (10)0.0416 (11)0.0005 (8)0.0030 (8)0.0041 (8)
C140.0503 (14)0.0391 (12)0.0510 (14)0.0056 (10)0.0053 (11)−0.0025 (10)
C150.0540 (15)0.0598 (16)0.0443 (14)−0.0019 (12)−0.0028 (11)−0.0037 (11)
C160.0352 (11)0.0594 (15)0.0489 (14)−0.0019 (11)−0.0020 (10)0.0163 (11)
C170.0371 (12)0.0464 (13)0.0518 (14)0.0093 (10)0.0074 (10)0.0080 (10)
C180.0398 (12)0.0373 (11)0.0453 (12)0.0029 (9)0.0051 (9)0.0022 (9)

Geometric parameters (Å, °)

Cl1—C161.752 (2)C6—H60.93
N1—C111.275 (3)C7—C81.398 (4)
N1—N21.383 (2)C7—H70.93
N2—C121.353 (3)C8—C91.365 (3)
N2—H20.899 (10)C8—H80.93
O1—C21.354 (3)C9—C101.410 (3)
O1—H10.82C9—H90.93
O2—C121.228 (2)C11—H110.93
C1—C21.392 (3)C12—C131.495 (3)
C1—C101.440 (3)C13—C141.386 (3)
C1—C111.457 (3)C13—C181.392 (3)
C2—C31.409 (3)C14—C151.385 (3)
C3—C41.356 (4)C14—H140.93
C3—H30.93C15—C161.381 (4)
C4—C51.418 (4)C15—H150.93
C4—H40.93C16—C171.373 (3)
C5—C61.412 (4)C17—C181.387 (3)
C5—C101.427 (3)C17—H170.93
C6—C71.361 (4)C18—H180.93
C11—N1—N2117.76 (18)C8—C9—H9119.2
C12—N2—N1117.57 (16)C10—C9—H9119.2
C12—N2—H2118 (2)C9—C10—C5117.3 (2)
N1—N2—H2121 (2)C9—C10—C1123.55 (19)
C2—O1—H1109.5C5—C10—C1119.1 (2)
C2—C1—C10119.01 (18)N1—C11—C1120.4 (2)
C2—C1—C11120.14 (19)N1—C11—H11119.8
C10—C1—C11120.85 (19)C1—C11—H11119.8
O1—C2—C1123.34 (19)O2—C12—N2122.48 (19)
O1—C2—C3115.7 (2)O2—C12—C13122.18 (19)
C1—C2—C3121.0 (2)N2—C12—C13115.34 (16)
C4—C3—C2120.2 (2)C14—C13—C18119.4 (2)
C4—C3—H3119.9C14—C13—C12118.30 (19)
C2—C3—H3119.9C18—C13—C12122.20 (19)
C3—C4—C5121.7 (2)C15—C14—C13120.7 (2)
C3—C4—H4119.2C15—C14—H14119.6
C5—C4—H4119.2C13—C14—H14119.6
C6—C5—C4121.8 (2)C16—C15—C14118.3 (2)
C6—C5—C10119.5 (2)C16—C15—H15120.8
C4—C5—C10118.7 (2)C14—C15—H15120.8
C7—C6—C5121.3 (2)C17—C16—C15122.5 (2)
C7—C6—H6119.3C17—C16—Cl1118.9 (2)
C5—C6—H6119.3C15—C16—Cl1118.62 (19)
C6—C7—C8119.4 (2)C16—C17—C18118.5 (2)
C6—C7—H7120.3C16—C17—H17120.7
C8—C7—H7120.3C18—C17—H17120.7
C9—C8—C7121.0 (3)C17—C18—C13120.5 (2)
C9—C8—H8119.5C17—C18—H18119.8
C7—C8—H8119.5C13—C18—H18119.8
C8—C9—C10121.6 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.872.584 (2)145
N2—H2···O2i0.90 (1)1.98 (1)2.858 (3)165 (4)

Symmetry codes: (i) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2654).

References

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