6-Chloro-N'-(2-hydr-oxy-1-naphthyl-methyl-ene)nicotinohydrazide.

The title compound, C(17)H(12)ClN(3)O(2), was synthesized by the Schiff base condensation reaction of 2-hydr-oxy-1-naphthaldehyde with 6-chloro-nicotinic acid hydrazide in a methanol solution. The mol-ecule 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 intra-molecular O-H⋯N hydrogen bond. The crystal structure is stabilized by inter-molecular 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 ▶); Chen et al. (1997 ▶); Fan et al. (2007 ▶); Kim et al. (2005 ▶); Nimitsiriwat et al. (2004 ▶); Ren et al. (2002 ▶).

Experimental

Crystal data

C17H12ClN3O2

M = 325.75

Monoclinic,

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 ▶) T min = 0.937, T max = 0.940

5692 measured reflections

2980 independent reflections

1948 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 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 ▶), 1447 Friedel pairs

Flack parameter: 0.11 (10)

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063611/bv2083Isup2.hkl

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

C17H12ClN3O2	F000 = 336
Mr = 325.75	Dx = 1.466 Mg m−3
Monoclinic, Pc	Mo Kα radiation λ = 0.71073 Å
a = 4.7450 (9) Å	Cell parameters from 790 reflections
b = 6.0420 (12) Å	θ = 2.4–24.3º
c = 25.752 (5) Å	µ = 0.27 mm−1
β = 91.93 (3)º	T = 293 (2) K
V = 737.9 (2) Å3	Block, yellow
Z = 2	0.23 × 0.20 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	2980 independent reflections
Radiation source: fine-focus sealed tube	1948 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.043
T = 293(2) K	θmax = 26.5º
ω scan	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.937, Tmax = 0.940	k = −7→7
5692 measured reflections	l = −32→32

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.057	w = 1/[σ2(Fo2) + (0.0375P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.110	(Δ/σ)max < 0.001
S = 0.99	Δρmax = 0.15 e Å−3
2980 reflections	Δρmin = −0.18 e Å−3
212 parameters	Extinction correction: none
3 restraints	Absolute structure: Flack (1983), 1447 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.11 (10)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
Cl1	0.0611 (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	−0.3567	0.2788	0.0929	0.077*
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)
C2	0.1344 (8)	1.2758 (6)	−0.02279 (15)	0.0472 (10)
H2A	0.2741	1.3785	−0.0141	0.057*
C3	0.0704 (8)	1.1058 (6)	0.01076 (16)	0.0390 (9)
H3	0.1677	1.0913	0.0425	0.047*
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	−0.4155	0.8905	−0.0608	0.063*
C6	−0.2328 (8)	0.7734 (6)	0.02998 (14)	0.0367 (9)
C7	0.0501 (10)	0.4617 (6)	0.13256 (18)	0.0401 (9)
H7	0.2148	0.5417	0.1391	0.048*
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	−0.1643	0.1654	0.067*
C11	−0.1272 (9)	−0.1079 (7)	0.22124 (18)	0.0569 (13)
H11	−0.1638	−0.2377	0.2392	0.068*
C12	0.0845 (9)	0.0363 (7)	0.24135 (17)	0.0485 (12)
C13	0.2286 (11)	−0.0050 (10)	0.28798 (17)	0.0631 (15)
H13	0.1877	−0.1323	0.3066	0.076*
C14	0.4314 (10)	0.1389 (9)	0.30741 (18)	0.0651 (14)
H14	0.5319	0.1062	0.3381	0.078*
C15	0.4840 (9)	0.3345 (8)	0.28043 (16)	0.0596 (13)
H15	0.6164	0.4348	0.2938	0.072*
C16	0.3413 (8)	0.3798 (7)	0.23432 (15)	0.0460 (10)
H16	0.3789	0.5106	0.2168	0.055*
C17	0.1391 (8)	0.2315 (7)	0.21308 (15)	0.0384 (10)
H2B	0.142 (3)	0.733 (7)	0.0613 (17)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.1123 (10)	0.0589 (7)	0.0659 (7)	−0.0054 (7)	0.0137 (6)	0.0212 (6)
O1	0.0287 (14)	0.0529 (18)	0.0662 (19)	−0.0089 (14)	−0.0033 (13)	0.0008 (15)
O2	0.0416 (15)	0.057 (2)	0.0557 (18)	−0.0132 (14)	0.0021 (14)	−0.0051 (15)
N1	0.073 (3)	0.055 (3)	0.044 (2)	−0.001 (2)	−0.005 (2)	0.0076 (19)
N2	0.0300 (17)	0.0427 (19)	0.0414 (18)	−0.0028 (15)	0.0004 (16)	0.0072 (16)
N3	0.040 (2)	0.041 (2)	0.0444 (19)	−0.0037 (17)	0.0083 (16)	0.0022 (17)
C1	0.059 (3)	0.043 (3)	0.044 (3)	−0.002 (2)	0.010 (2)	0.005 (2)
C2	0.046 (2)	0.042 (3)	0.053 (3)	−0.006 (2)	0.004 (2)	−0.005 (2)
C3	0.037 (2)	0.040 (2)	0.040 (2)	−0.004 (2)	−0.0024 (18)	0.000 (2)
C4	0.036 (2)	0.041 (3)	0.036 (2)	0.0013 (19)	0.0026 (18)	−0.0020 (19)
C5	0.048 (3)	0.053 (3)	0.056 (3)	−0.007 (2)	−0.001 (2)	−0.011 (2)
C6	0.033 (2)	0.039 (2)	0.038 (2)	−0.0016 (19)	0.0035 (18)	−0.0067 (18)
C7	0.035 (2)	0.041 (2)	0.045 (2)	0.000 (2)	0.0052 (17)	0.003 (2)
C8	0.033 (2)	0.035 (2)	0.045 (2)	−0.0019 (18)	0.0092 (18)	−0.0023 (18)
C9	0.038 (2)	0.045 (3)	0.047 (3)	0.002 (2)	0.006 (2)	−0.002 (2)
C10	0.055 (3)	0.042 (3)	0.071 (3)	−0.014 (2)	0.019 (3)	−0.010 (3)
C11	0.063 (3)	0.041 (3)	0.068 (3)	−0.007 (2)	0.016 (3)	0.007 (2)
C12	0.056 (3)	0.037 (3)	0.053 (3)	0.007 (2)	0.016 (2)	0.006 (2)
C13	0.076 (4)	0.071 (4)	0.043 (3)	0.016 (3)	0.014 (3)	0.022 (3)
C14	0.068 (3)	0.088 (4)	0.040 (3)	0.028 (3)	0.006 (2)	0.010 (3)
C15	0.066 (3)	0.065 (3)	0.047 (3)	0.005 (3)	−0.002 (2)	0.002 (2)
C16	0.043 (3)	0.046 (3)	0.049 (3)	−0.003 (2)	0.002 (2)	0.003 (2)
C17	0.038 (2)	0.039 (3)	0.038 (2)	0.0033 (19)	0.0086 (19)	−0.0006 (19)

Cl1—C1	1.734 (4)	C7—H7	0.9300
O1—C6	1.236 (4)	C8—C9	1.391 (5)
O2—C9	1.357 (4)	C8—C17	1.438 (5)
O2—H2	0.8200	C9—C10	1.395 (6)
N1—C1	1.323 (5)	C10—C11	1.343 (6)
N1—C5	1.339 (5)	C10—H10	0.9300
N2—C6	1.336 (4)	C11—C12	1.415 (6)
N2—N3	1.375 (4)	C11—H11	0.9300
N2—H2B	0.900 (10)	C12—C13	1.385 (6)
N3—C7	1.288 (5)	C12—C17	1.414 (5)
C1—C2	1.373 (5)	C13—C14	1.378 (7)
C2—C3	1.382 (5)	C13—H13	0.9300
C2—H2A	0.9300	C14—C15	1.398 (6)
C3—C4	1.393 (5)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.374 (5)
C4—C5	1.365 (5)	C15—H15	0.9300
C4—C6	1.479 (5)	C16—C17	1.410 (5)
C5—H5	0.9300	C16—H16	0.9300
C7—C8	1.447 (5)
C9—O2—H2	109.5	C17—C8—C7	121.8 (4)
C1—N1—C5	114.8 (4)	O2—C9—C8	123.2 (4)
C6—N2—N3	117.5 (3)	O2—C9—C10	115.7 (4)
C6—N2—H2B	120 (3)	C8—C9—C10	121.1 (4)
N3—N2—H2B	122 (3)	C11—C10—C9	120.1 (4)
C7—N3—N2	118.0 (3)	C11—C10—H10	120.0
N1—C1—C2	125.2 (4)	C9—C10—H10	120.0
N1—C1—Cl1	115.8 (3)	C10—C11—C12	122.7 (4)
C2—C1—Cl1	119.0 (3)	C10—C11—H11	118.7
C1—C2—C3	118.0 (4)	C12—C11—H11	118.7
C1—C2—H2A	121.0	C13—C12—C17	120.2 (4)
C3—C2—H2A	121.0	C13—C12—C11	122.0 (4)
C2—C3—C4	119.0 (4)	C17—C12—C11	117.7 (4)
C2—C3—H3	120.5	C14—C13—C12	121.3 (5)
C4—C3—H3	120.5	C14—C13—H13	119.3
C5—C4—C3	116.7 (4)	C12—C13—H13	119.3
C5—C4—C6	120.0 (4)	C13—C14—C15	119.1 (5)
C3—C4—C6	123.3 (4)	C13—C14—H14	120.4
N1—C5—C4	126.3 (4)	C15—C14—H14	120.4
N1—C5—H5	116.9	C16—C15—C14	120.4 (5)
C4—C5—H5	116.9	C16—C15—H15	119.8
O1—C6—N2	122.6 (3)	C14—C15—H15	119.8
O1—C6—C4	120.7 (4)	C15—C16—C17	121.2 (4)
N2—C6—C4	116.6 (3)	C15—C16—H16	119.4
N3—C7—C8	120.7 (4)	C17—C16—H16	119.4
N3—C7—H7	119.7	C16—C17—C12	117.7 (4)
C8—C7—H7	119.7	C16—C17—C8	122.6 (3)
C9—C8—C17	118.5 (3)	C12—C17—C8	119.8 (4)
C9—C8—C7	119.6 (4)

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

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) ; (ii) .