4-Chloro-N'-(2-hydr-oxy-1-naphthyl-idene)benzohydrazide.

The mol-ecule of the title compound, C(18)H(13)ClN(2)O(2), 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 mol-ecular structure. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds and π-π stacking inter-actions [centroid-centroid distance = 3.603 (2) Å], forming chains running along the b axis.

Related literature

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

Experimental

Crystal data

C18H13ClN2O2

M = 324.75

Monoclinic,

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 ▶) 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 ▶), with 596 Friedel pairs

Flack parameter: 0.03 (7)

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAIn class="Chemical">NT ; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

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

C18H13ClN2O2	F000 = 336
Mr = 324.75	Dx = 1.442 Mg m−3
Monoclinic, Pc	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 2145 reflections
a = 6.200 (3) Å	θ = 2.8–29.3º
b = 4.788 (2) Å	µ = 0.27 mm−1
c = 25.320 (11) Å	T = 298 (2) K
β = 95.844 (7)º	Block, colourless
V = 747.8 (6) Å3	0.23 × 0.21 × 0.20 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	2197 independent reflections
Radiation source: fine-focus sealed tube	2039 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.017
T = 298(2) K	θmax = 27.0º
ω scans	θmin = 3.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −5→7
Tmin = 0.941, Tmax = 0.949	k = −6→6
4001 measured reflections	l = −31→26

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)] = 0.032	w = 1/[σ2(Fo2) + (0.0403P)2 + 0.1026P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.080	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.12 e Å−3
2197 reflections	Δρmin = −0.19 e Å−3
212 parameters	Extinction correction: none
3 restraints	Absolute structure: Flack (1983), with 596 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (7)
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	1.44733 (12)	0.28331 (19)	0.25960 (4)	0.0780 (3)
N1	0.3640 (3)	0.4990 (4)	0.05683 (7)	0.0395 (4)
N2	0.5480 (3)	0.4210 (4)	0.08892 (8)	0.0390 (4)
O1	0.0022 (3)	0.7705 (3)	0.04417 (7)	0.0512 (4)
H1	0.1220	0.7293	0.0589	0.077*
O2	0.5730 (3)	0.8546 (3)	0.12464 (7)	0.0504 (4)
C1	0.0931 (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	−0.3413	0.7847	−0.0163	0.062*
C4	−0.3071 (4)	0.5020 (5)	−0.07244 (11)	0.0529 (6)
H4	−0.4422	0.5341	−0.0909	0.063*
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	−0.3580	0.1895	−0.1589	0.065*
C7	−0.0893 (5)	−0.0380 (6)	−0.15817 (10)	0.0587 (7)
H7	−0.1289	−0.1318	−0.1898	0.070*
C8	0.1105 (5)	−0.0923 (6)	−0.12918 (10)	0.0549 (6)
H8	0.2035	−0.2233	−0.1418	0.066*
C9	0.1709 (4)	0.0441 (5)	−0.08267 (9)	0.0478 (6)
H9	0.3051	0.0049	−0.0643	0.057*
C10	0.0348 (3)	0.2428 (5)	−0.06184 (9)	0.0384 (5)
C11	0.2922 (3)	0.3316 (5)	0.01999 (9)	0.0393 (5)
H11	0.3673	0.1678	0.0145	0.047*
C12	0.6429 (3)	0.6152 (4)	0.12246 (8)	0.0371 (5)
C13	0.8398 (3)	0.5189 (4)	0.15662 (8)	0.0357 (4)
C14	0.8939 (4)	0.6535 (5)	0.20461 (10)	0.0468 (6)
H14	0.8045	0.7941	0.2153	0.056*
C15	1.0795 (4)	0.5809 (6)	0.23675 (10)	0.0532 (6)
H15	1.1155	0.6701	0.2691	0.064*
C16	1.2100 (4)	0.3728 (5)	0.21960 (9)	0.0483 (6)
C17	1.1626 (4)	0.2370 (5)	0.17207 (10)	0.0449 (5)
H17	1.2543	0.0991	0.1613	0.054*
C18	0.9751 (3)	0.3101 (4)	0.14053 (9)	0.0407 (5)
H18	0.9393	0.2189	0.1084	0.049*
H2	0.576 (6)	0.240 (3)	0.0963 (14)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0468 (3)	0.1144 (6)	0.0692 (4)	0.0089 (4)	−0.0112 (3)	0.0192 (4)
N1	0.0344 (9)	0.0357 (9)	0.0476 (10)	0.0038 (7)	0.0003 (8)	0.0045 (7)
N2	0.0373 (9)	0.0305 (8)	0.0475 (10)	0.0053 (8)	−0.0031 (8)	0.0022 (7)
O1	0.0545 (10)	0.0446 (9)	0.0552 (10)	0.0141 (8)	0.0086 (8)	0.0030 (8)
O2	0.0490 (9)	0.0290 (7)	0.0715 (11)	0.0077 (7)	−0.0016 (8)	−0.0015 (7)
C1	0.0326 (11)	0.0347 (10)	0.0460 (12)	0.0008 (9)	0.0040 (9)	0.0108 (9)
C2	0.0382 (12)	0.0373 (12)	0.0465 (12)	0.0038 (9)	0.0086 (9)	0.0103 (9)
C3	0.0400 (12)	0.0496 (14)	0.0662 (16)	0.0121 (11)	0.0114 (11)	0.0140 (12)
C4	0.0336 (12)	0.0531 (14)	0.0700 (17)	0.0073 (10)	−0.0036 (11)	0.0165 (12)
C5	0.0367 (12)	0.0431 (12)	0.0561 (14)	−0.0036 (10)	−0.0017 (10)	0.0164 (10)
C6	0.0490 (14)	0.0546 (15)	0.0558 (15)	−0.0049 (12)	−0.0129 (11)	0.0132 (12)
C7	0.0672 (17)	0.0599 (16)	0.0468 (15)	−0.0122 (14)	−0.0056 (12)	0.0016 (12)
C8	0.0576 (14)	0.0563 (15)	0.0507 (15)	0.0031 (12)	0.0050 (11)	−0.0020 (12)
C9	0.0427 (13)	0.0486 (13)	0.0512 (14)	0.0048 (10)	0.0008 (10)	0.0022 (10)
C10	0.0330 (10)	0.0350 (12)	0.0466 (12)	−0.0017 (8)	0.0014 (8)	0.0102 (8)
C11	0.0345 (11)	0.0343 (10)	0.0491 (12)	0.0053 (8)	0.0038 (9)	0.0047 (9)
C12	0.0367 (11)	0.0311 (10)	0.0439 (12)	0.0030 (9)	0.0059 (9)	0.0046 (8)
C13	0.0371 (11)	0.0283 (10)	0.0416 (11)	0.0005 (8)	0.0030 (8)	0.0041 (8)
C14	0.0503 (14)	0.0391 (12)	0.0510 (14)	0.0056 (10)	0.0053 (11)	−0.0025 (10)
C15	0.0540 (15)	0.0598 (16)	0.0443 (14)	−0.0019 (12)	−0.0028 (11)	−0.0037 (11)
C16	0.0352 (11)	0.0594 (15)	0.0489 (14)	−0.0019 (11)	−0.0020 (10)	0.0163 (11)
C17	0.0371 (12)	0.0464 (13)	0.0518 (14)	0.0093 (10)	0.0074 (10)	0.0080 (10)
C18	0.0398 (12)	0.0373 (11)	0.0453 (12)	0.0029 (9)	0.0051 (9)	0.0022 (9)

Cl1—C16	1.752 (2)	C6—H6	0.93
N1—C11	1.275 (3)	C7—C8	1.398 (4)
N1—N2	1.383 (2)	C7—H7	0.93
N2—C12	1.353 (3)	C8—C9	1.365 (3)
N2—H2	0.899 (10)	C8—H8	0.93
O1—C2	1.354 (3)	C9—C10	1.410 (3)
O1—H1	0.82	C9—H9	0.93
O2—C12	1.228 (2)	C11—H11	0.93
C1—C2	1.392 (3)	C12—C13	1.495 (3)
C1—C10	1.440 (3)	C13—C14	1.386 (3)
C1—C11	1.457 (3)	C13—C18	1.392 (3)
C2—C3	1.409 (3)	C14—C15	1.385 (3)
C3—C4	1.356 (4)	C14—H14	0.93
C3—H3	0.93	C15—C16	1.381 (4)
C4—C5	1.418 (4)	C15—H15	0.93
C4—H4	0.93	C16—C17	1.373 (3)
C5—C6	1.412 (4)	C17—C18	1.387 (3)
C5—C10	1.427 (3)	C17—H17	0.93
C6—C7	1.361 (4)	C18—H18	0.93
C11—N1—N2	117.76 (18)	C8—C9—H9	119.2
C12—N2—N1	117.57 (16)	C10—C9—H9	119.2
C12—N2—H2	118 (2)	C9—C10—C5	117.3 (2)
N1—N2—H2	121 (2)	C9—C10—C1	123.55 (19)
C2—O1—H1	109.5	C5—C10—C1	119.1 (2)
C2—C1—C10	119.01 (18)	N1—C11—C1	120.4 (2)
C2—C1—C11	120.14 (19)	N1—C11—H11	119.8
C10—C1—C11	120.85 (19)	C1—C11—H11	119.8
O1—C2—C1	123.34 (19)	O2—C12—N2	122.48 (19)
O1—C2—C3	115.7 (2)	O2—C12—C13	122.18 (19)
C1—C2—C3	121.0 (2)	N2—C12—C13	115.34 (16)
C4—C3—C2	120.2 (2)	C14—C13—C18	119.4 (2)
C4—C3—H3	119.9	C14—C13—C12	118.30 (19)
C2—C3—H3	119.9	C18—C13—C12	122.20 (19)
C3—C4—C5	121.7 (2)	C15—C14—C13	120.7 (2)
C3—C4—H4	119.2	C15—C14—H14	119.6
C5—C4—H4	119.2	C13—C14—H14	119.6
C6—C5—C4	121.8 (2)	C16—C15—C14	118.3 (2)
C6—C5—C10	119.5 (2)	C16—C15—H15	120.8
C4—C5—C10	118.7 (2)	C14—C15—H15	120.8
C7—C6—C5	121.3 (2)	C17—C16—C15	122.5 (2)
C7—C6—H6	119.3	C17—C16—Cl1	118.9 (2)
C5—C6—H6	119.3	C15—C16—Cl1	118.62 (19)
C6—C7—C8	119.4 (2)	C16—C17—C18	118.5 (2)
C6—C7—H7	120.3	C16—C17—H17	120.7
C8—C7—H7	120.3	C18—C17—H17	120.7
C9—C8—C7	121.0 (3)	C17—C18—C13	120.5 (2)
C9—C8—H8	119.5	C17—C18—H18	119.8
C7—C8—H8	119.5	C13—C18—H18	119.8
C8—C9—C10	121.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.584 (2)	145
N2—H2···O2i	0.90 (1)	1.98 (1)	2.858 (3)	165 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.87	2.584 (2)	145
N2—H2⋯O2i	0.90 (1)	1.98 (1)	2.858 (3)	165 (4)

Symmetry code: (i) .