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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o150
https://doi.org/10.1107/S1600536807063611

6-Chloro-N′-(2-hydr­­oxy-1-naphthyl­methyl­ene)nicotinohydrazide

Feng Zhia*

aDepartment of Neurosurgery, Third Affiliated Hospital of Suzhou University, Changzhou 213000, People's Republic of China
*Correspondence e-mail: changzhou_zhi@yahoo.com.cn

(Received 30 October 2007; accepted 26 November 2007; online 6 December 2007)

The title compound, C17H12ClN3O2, was synthesized by the Schiff base condensation reaction of 2-hydr­oxy-1-naphthaldehyde with 6-chloro­nicotinic acid hydrazide in a methanol solution. The mol­ecule displays a trans configuration with respect to the C=N and C—N bonds. The dihedral angle between the naphthyl ring system and the pyridine ring is 7.6 (4)°. There is an intra­molecular O—H⋯N hydrogen bond. The crystal structure is stabilized by inter­molecular N—H⋯O and C—H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For related literature, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]); Chen et al. (1997[Chen, H. Q., Hall, S., Zheng, B. & Rhodes, J. (1997). Biodrugs, 7, 217-231.]); Fan et al. (2007[Fan, Y. H., He, X. T., Bi, C. F., Guo, F., Bao, Y. & Chen, R. (2007). Russ. J. Coord. Chem. 33, 535-538.]); Kim et al. (2005[Kim, H.-J., Kim, W., Lough, A. J., Kim, B. M. & Chin, J. (2005). J. Am. Chem. Soc. 127, 16776-16777.]); Nimitsiriwat et al. (2004[Nimitsiriwat, N., Marshall, E. L., Gibson, V. C., Elsegood, M. R. J. & Dale, S. H. (2004). J. Am. Chem. Soc. 126, 13598-13599.]); Ren et al. (2002[Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., McKenna, C. E., Csipke, C., Tokes, Z. A. & Lien, E. J. (2002). J. Med. Chem. 45, 410-419.]).

[Scheme 1]

Experimental

Crystal data

  • C17H12ClN3O2

  • Mr = 325.75

  • Monoclinic, P c

  • a = 4.7450 (9) Å

  • b = 6.0420 (12) Å

  • c = 25.752 (5) Å

  • β = 91.93 (3)°

  • V = 737.9 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 293 (2) K

  • 0.23 × 0.20 × 0.20 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.937, Tmax = 0.940

  • 5692 measured reflections

  • 2980 independent reflections

  • 1948 reflections with I > 2σ(I)

  • Rint = 0.043
Refinement

  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.110

  • S = 0.99

  • 2980 reflections

  • 212 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.18 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1447 Friedel pairs

  • Flack parameter: 0.11 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2⋯N3 0.82 1.84 2.559 (4) 146
N2—H2B⋯O1i 0.900 (10) 2.05 (2) 2.862 (4) 150 (4)
C2—H2A⋯O1ii 0.93 2.50 3.396 (4) 161
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z.

Data collection: SMART (Bruker, 2002[Bruker (2002). SAINT (Version 5.62) and SMART (Version 6.02). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SAINT (Version 5.62) and SMART (Version 6.02). Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a[Sheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a[Sheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Sheldrick, 1997b[Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807063611/bv2083sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063611/bv2083Isup2.hkl

checkCIF report


Comment top

Schiff base compounds have been widely investigated over a century (Fan et al., 2007; Kim et al., 2005; Nimitsiriwat et al., 2004). Some of the compounds have been found to have pharmacological and antibacterial activity (Chen et al., 1997; Ren et al., 2002). In this paper, the crystal structure of a new Schiff base compound derived from the condensation reaction of 2-hydroxy-1-naphthaldehyde with 6-chloronicotinic acid hydrazide is reported.

The Schiff base molecule of the compound displays a trans configuration with respect to the C?N and C—N bonds (Fig. 1). The dihedral angle between the C8—C17 naphthyl ring and the C1—C5/N1 pyridine ring is 7.6 (4)°. All the bond lengths are within normal ranges (Allen et al., 1987). There is an intramolecular O–H···N hydrogen bond in the molecule (Table 1). The crystal structure is stabilized by intermolecular N–H···O and C–H···O hydrogen bonds (Table 1), forming chains running along the b axis (Fig. 2).

Related literature top

For related literature, see: Allen et al. (1987); Chen et al. (1997); Fan et al. (2007); Kim et al. (2005); Nimitsiriwat et al. (2004); Ren et al. (2002).

Experimental top

2-Hydroxy-1-naphthaldehyde (0.1 mmol, 17.2 mg) and 6-chloronicotinic acid hydrazide (0.1 mmol, 17.1 mg) were dissolved in a methanol solution (10 ml). The mixture was stirred at room temperature to give a clear yellow solution. Crystals of the title compound were formed by gradual evaporation of the solvent for two days at room temperature.

Refinement top

Atom H2B was located from a difference Fourier map and refined isotropically, with N–H distance restrained to 0.90 (1) Å. Other H atoms were constrained to ideal geometries, with C–H = 0.93 Å, O–H = 0.82 Å, and with Uiso(H) set to 1.2Ueq(C) and 1.5Ueq(O).

Structure description top

Schiff base compounds have been widely investigated over a century (Fan et al., 2007; Kim et al., 2005; Nimitsiriwat et al., 2004). Some of the compounds have been found to have pharmacological and antibacterial activity (Chen et al., 1997; Ren et al., 2002). In this paper, the crystal structure of a new Schiff base compound derived from the condensation reaction of 2-hydroxy-1-naphthaldehyde with 6-chloronicotinic acid hydrazide is reported.

The Schiff base molecule of the compound displays a trans configuration with respect to the C?N and C—N bonds (Fig. 1). The dihedral angle between the C8—C17 naphthyl ring and the C1—C5/N1 pyridine ring is 7.6 (4)°. All the bond lengths are within normal ranges (Allen et al., 1987). There is an intramolecular O–H···N hydrogen bond in the molecule (Table 1). The crystal structure is stabilized by intermolecular N–H···O and C–H···O hydrogen bonds (Table 1), forming chains running along the b axis (Fig. 2).

For related literature, see: Allen et al. (1987); Chen et al. (1997); Fan et al. (2007); Kim et al. (2005); Nimitsiriwat et al. (2004); Ren et al. (2002).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. The structure of (I) at the 30% probability level.
[Figure 2] Fig. 2. Molecular packing of (I), viewed along the a axis. Intermolecular hydrogen bonds are shown as dashed lines.
6-Chloro-N'-(2-hydroxy-1-naphthylmethylene)nicotinohydrazide top
Crystal data top
C17H12ClN3O2F(000) = 336
Mr = 325.75Dx = 1.466 Mg m−3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
a = 4.7450 (9) ÅCell parameters from 790 reflections
b = 6.0420 (12) Åθ = 2.4–24.3°
c = 25.752 (5) ŵ = 0.27 mm−1
β = 91.93 (3)°T = 293 K
V = 737.9 (2) Å3Block, yellow
Z = 20.23 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		2980 independent reflections
Radiation source: fine-focus sealed tube1948 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ω scanθmax = 26.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −5→5
Tmin = 0.937, Tmax = 0.940k = −7→7
5692 measured reflectionsl = −32→32
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0375P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
2980 reflectionsΔρmax = 0.15 e Å−3
212 parametersΔρmin = −0.18 e Å−3
3 restraintsAbsolute structure: Flack (1983), 1447 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.11 (10)
Crystal data top
C17H12ClN3O2V = 737.9 (2) Å3
Mr = 325.75Z = 2
Monoclinic, PcMo Kα radiation
a = 4.7450 (9) ŵ = 0.27 mm−1
b = 6.0420 (12) ÅT = 293 K
c = 25.752 (5) Å0.23 × 0.20 × 0.20 mm
β = 91.93 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2980 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1948 reflections with I > 2σ(I)
Tmin = 0.937, Tmax = 0.940Rint = 0.043
5692 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.057H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110Δρmax = 0.15 e Å−3
S = 0.99Δρmin = −0.18 e Å−3
2980 reflectionsAbsolute structure: Flack (1983), 1447 Friedel pairs
212 parametersAbsolute structure parameter: 0.11 (10)
3 restraints
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
Cl10.0611 (3)1.5001 (2)−0.11216 (6)0.0788 (4)
O1−0.4774 (5)0.7030 (4)0.02688 (11)0.0494 (7)
O2−0.3951 (6)0.1598 (5)0.10628 (11)0.0515 (7)
H2−0.35670.27880.09290.077*
N1−0.2165 (8)1.1504 (6)−0.08492 (13)0.0577 (10)
N2−0.0394 (6)0.6927 (6)0.06381 (12)0.0380 (8)
N3−0.1179 (6)0.5186 (5)0.09455 (13)0.0416 (8)
C1−0.0145 (9)1.2884 (7)−0.06934 (16)0.0484 (11)
C20.1344 (8)1.2758 (6)−0.02279 (15)0.0472 (10)
H2A0.27411.3785−0.01410.057*
C30.0704 (8)1.1058 (6)0.01076 (16)0.0390 (9)
H30.16771.09130.04250.047*
C4−0.1420 (8)0.9566 (6)−0.00370 (16)0.0375 (10)
C5−0.2731 (9)0.9895 (7)−0.05108 (17)0.0525 (12)
H5−0.41550.8905−0.06080.063*
C6−0.2328 (8)0.7734 (6)0.02998 (14)0.0367 (9)
C70.0501 (10)0.4617 (6)0.13256 (18)0.0401 (9)
H70.21480.54170.13910.048*
C8−0.0149 (7)0.2745 (6)0.16510 (15)0.0376 (9)
C9−0.2276 (8)0.1283 (7)0.14941 (16)0.0432 (10)
C10−0.2774 (9)−0.0650 (7)0.17726 (19)0.0555 (13)
H10−0.4147−0.16430.16540.067*
C11−0.1272 (9)−0.1079 (7)0.22124 (18)0.0569 (13)
H11−0.1638−0.23770.23920.068*
C120.0845 (9)0.0363 (7)0.24135 (17)0.0485 (12)
C130.2286 (11)−0.0050 (10)0.28798 (17)0.0631 (15)
H130.1877−0.13230.30660.076*
C140.4314 (10)0.1389 (9)0.30741 (18)0.0651 (14)
H140.53190.10620.33810.078*
C150.4840 (9)0.3345 (8)0.28043 (16)0.0596 (13)
H150.61640.43480.29380.072*
C160.3413 (8)0.3798 (7)0.23432 (15)0.0460 (10)
H160.37890.51060.21680.055*
C170.1391 (8)0.2315 (7)0.21308 (15)0.0384 (10)
H2B0.142 (3)0.733 (7)0.0613 (17)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1123 (10)0.0589 (7)0.0659 (7)−0.0054 (7)0.0137 (6)0.0212 (6)
O10.0287 (14)0.0529 (18)0.0662 (19)−0.0089 (14)−0.0033 (13)0.0008 (15)
O20.0416 (15)0.057 (2)0.0557 (18)−0.0132 (14)0.0021 (14)−0.0051 (15)
N10.073 (3)0.055 (3)0.044 (2)−0.001 (2)−0.005 (2)0.0076 (19)
N20.0300 (17)0.0427 (19)0.0414 (18)−0.0028 (15)0.0004 (16)0.0072 (16)
N30.040 (2)0.041 (2)0.0444 (19)−0.0037 (17)0.0083 (16)0.0022 (17)
C10.059 (3)0.043 (3)0.044 (3)−0.002 (2)0.010 (2)0.005 (2)
C20.046 (2)0.042 (3)0.053 (3)−0.006 (2)0.004 (2)−0.005 (2)
C30.037 (2)0.040 (2)0.040 (2)−0.004 (2)−0.0024 (18)0.000 (2)
C40.036 (2)0.041 (3)0.036 (2)0.0013 (19)0.0026 (18)−0.0020 (19)
C50.048 (3)0.053 (3)0.056 (3)−0.007 (2)−0.001 (2)−0.011 (2)
C60.033 (2)0.039 (2)0.038 (2)−0.0016 (19)0.0035 (18)−0.0067 (18)
C70.035 (2)0.041 (2)0.045 (2)0.000 (2)0.0052 (17)0.003 (2)
C80.033 (2)0.035 (2)0.045 (2)−0.0019 (18)0.0092 (18)−0.0023 (18)
C90.038 (2)0.045 (3)0.047 (3)0.002 (2)0.006 (2)−0.002 (2)
C100.055 (3)0.042 (3)0.071 (3)−0.014 (2)0.019 (3)−0.010 (3)
C110.063 (3)0.041 (3)0.068 (3)−0.007 (2)0.016 (3)0.007 (2)
C120.056 (3)0.037 (3)0.053 (3)0.007 (2)0.016 (2)0.006 (2)
C130.076 (4)0.071 (4)0.043 (3)0.016 (3)0.014 (3)0.022 (3)
C140.068 (3)0.088 (4)0.040 (3)0.028 (3)0.006 (2)0.010 (3)
C150.066 (3)0.065 (3)0.047 (3)0.005 (3)−0.002 (2)0.002 (2)
C160.043 (3)0.046 (3)0.049 (3)−0.003 (2)0.002 (2)0.003 (2)
C170.038 (2)0.039 (3)0.038 (2)0.0033 (19)0.0086 (19)−0.0006 (19)
Geometric parameters (Å, º) top
Cl1—C11.734 (4)C7—H70.9300
O1—C61.236 (4)C8—C91.391 (5)
O2—C91.357 (4)C8—C171.438 (5)
O2—H20.8200C9—C101.395 (6)
N1—C11.323 (5)C10—C111.343 (6)
N1—C51.339 (5)C10—H100.9300
N2—C61.336 (4)C11—C121.415 (6)
N2—N31.375 (4)C11—H110.9300
N2—H2B0.900 (10)C12—C131.385 (6)
N3—C71.288 (5)C12—C171.414 (5)
C1—C21.373 (5)C13—C141.378 (7)
C2—C31.382 (5)C13—H130.9300
C2—H2A0.9300C14—C151.398 (6)
C3—C41.393 (5)C14—H140.9300
C3—H30.9300C15—C161.374 (5)
C4—C51.365 (5)C15—H150.9300
C4—C61.479 (5)C16—C171.410 (5)
C5—H50.9300C16—H160.9300
C7—C81.447 (5)
C9—O2—H2109.5C17—C8—C7121.8 (4)
C1—N1—C5114.8 (4)O2—C9—C8123.2 (4)
C6—N2—N3117.5 (3)O2—C9—C10115.7 (4)
C6—N2—H2B120 (3)C8—C9—C10121.1 (4)
N3—N2—H2B122 (3)C11—C10—C9120.1 (4)
C7—N3—N2118.0 (3)C11—C10—H10120.0
N1—C1—C2125.2 (4)C9—C10—H10120.0
N1—C1—Cl1115.8 (3)C10—C11—C12122.7 (4)
C2—C1—Cl1119.0 (3)C10—C11—H11118.7
C1—C2—C3118.0 (4)C12—C11—H11118.7
C1—C2—H2A121.0C13—C12—C17120.2 (4)
C3—C2—H2A121.0C13—C12—C11122.0 (4)
C2—C3—C4119.0 (4)C17—C12—C11117.7 (4)
C2—C3—H3120.5C14—C13—C12121.3 (5)
C4—C3—H3120.5C14—C13—H13119.3
C5—C4—C3116.7 (4)C12—C13—H13119.3
C5—C4—C6120.0 (4)C13—C14—C15119.1 (5)
C3—C4—C6123.3 (4)C13—C14—H14120.4
N1—C5—C4126.3 (4)C15—C14—H14120.4
N1—C5—H5116.9C16—C15—C14120.4 (5)
C4—C5—H5116.9C16—C15—H15119.8
O1—C6—N2122.6 (3)C14—C15—H15119.8
O1—C6—C4120.7 (4)C15—C16—C17121.2 (4)
N2—C6—C4116.6 (3)C15—C16—H16119.4
N3—C7—C8120.7 (4)C17—C16—H16119.4
N3—C7—H7119.7C16—C17—C12117.7 (4)
C8—C7—H7119.7C16—C17—C8122.6 (3)
C9—C8—C17118.5 (3)C12—C17—C8119.8 (4)
C9—C8—C7119.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N30.821.842.559 (4)146
N2—H2B···O1i0.90 (1)2.05 (2)2.862 (4)150 (4)
C2—H2A···O1ii0.932.503.396 (4)161
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC17H12ClN3O2
Mr325.75
Crystal system, space groupMonoclinic, Pc
Temperature (K)293
a, b, c (Å)4.7450 (9), 6.0420 (12), 25.752 (5)
β (°) 91.93 (3)
V (Å3)737.9 (2)
Z2
Radiation typeMo Kα
µ (mm−1)0.27
Crystal size (mm)0.23 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.937, 0.940
No. of measured, independent and
observed [I > 2σ(I)] reflections		5692, 2980, 1948
Rint0.043
(sin θ/λ)max (Å−1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.110, 0.99
No. of reflections2980
No. of parameters212
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.15, −0.18
Absolute structureFlack (1983), 1447 Friedel pairs
Absolute structure parameter0.11 (10)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N30.821.842.559 (4)146
N2—H2B···O1i0.900 (10)2.05 (2)2.862 (4)150 (4)
C2—H2A···O1ii0.932.503.396 (4)161
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z.
 

Acknowledgements

Financial support from the Third Affiliated Hospital of Suzhou University is acknowledged.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
 First citationBruker (2002). SAINT (Version 5.62) and SMART (Version 6.02). Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChen, H. Q., Hall, S., Zheng, B. & Rhodes, J. (1997). Biodrugs, 7, 217–231.  CrossRef PubMed CAS Web of Science Google Scholar
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ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o150
https://doi.org/10.1107/S1600536807063611
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