N'-Benzoyl-3-hydr-oxy-2-naphthohydrazide.

In the title compound, C(18)H(14)N(2)O(3), the dihedral angle between the planes of the naphthalene and phenyl ring systems is 2.64 (2)°. Mol-ecules are engaged in π-π stacking (mean interplanar distance = 3.339 between naphthalene rings and 3.357 Å between benzene rings )and hydrogen-bonding inter-actions.

Related literature

For related literature, see: Alexiou et al. (2002 ▶); Gaynor et al. (2002 ▶); Lah & Pecoraro (1989 ▶); Lehaire et al. (2002 ▶); Liu et al. (2001 ▶); Saalfrank et al. (2001 ▶).

Experimental

Crystal data

C18H14N2O3

M = 306.31

Monoclinic,

a = 4.8049 (10) Å

b = 5.0231 (10) Å

c = 29.398 (6) Å

β = 91.59 (3)°

V = 709.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 273 (2) K

0.35 × 0.24 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.927, T max = 0.984

6959 measured reflections

1798 independent reflections

1397 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.112

S = 1.05

1798 reflections

208 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure; software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012919/hg2387sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012919/hg2387Isup2.hkl

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

C18H14N2O3	F000 = 320
Mr = 306.31	Dx = 1.434 Mg m−3
Monoclinic, P21	Melting point = 219–223 K
Hall symbol: P 2yb	Mo Kα radiation λ = 0.71073 Å
a = 4.8049 (10) Å	Cell parameters from 4889 reflections
b = 5.0231 (10) Å	θ = 3.5–27.5º
c = 29.398 (6) Å	µ = 0.10 mm−1
β = 91.59 (3)º	T = 273 (2) K
V = 709.3 (2) Å3	Platelet, colorless
Z = 2	0.35 × 0.24 × 0.14 mm

Rigaku R-AXIS RAPID diffractometer	1798 independent reflections
Radiation source: fine-focus sealed tube	1397 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.044
T = 273(2) K	θmax = 27.5º
ω scans	θmin = 3.5º
Absorption correction: multi-scan(ABSCOR; Higashi,1995)	h = −6→6
Tmin = 0.927, Tmax = 0.984	k = −6→5
6959 measured reflections	l = −38→38

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0467P)2 + 0.1714P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1798 reflections	Δρmax = 0.18 e Å−3
208 parameters	Δρmin = −0.18 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
C1	0.8504 (7)	−0.1340 (8)	0.04316 (11)	0.0580 (10)
H1A	0.9337	−0.1095	0.0153	0.070*
C2	0.9282 (8)	0.0197 (9)	0.07930 (11)	0.0644 (11)
H2A	1.0645	0.1491	0.0759	0.077*
C3	0.5261 (8)	−0.3656 (8)	0.08826 (12)	0.0646 (11)
H3A	0.3923	−0.4981	0.0909	0.078*
C4	0.6474 (8)	−0.3272 (9)	0.04768 (12)	0.0607 (10)
H4A	0.5941	−0.4312	0.0228	0.073*
C5	0.5989 (6)	−0.2081 (7)	0.12670 (10)	0.0426 (7)
C6	0.8049 (6)	−0.0137 (7)	0.12216 (10)	0.0438 (7)
C7	0.8769 (7)	0.1425 (7)	0.16055 (10)	0.0491 (8)
H7A	1.0142	0.2715	0.1578	0.059*
C8	0.4731 (7)	−0.2387 (8)	0.16918 (11)	0.0512 (8)
H8A	0.3369	−0.3684	0.1724	0.061*
C9	0.5449 (5)	−0.0842 (6)	0.20558 (9)	0.0362 (6)
C10	0.7539 (6)	0.1128 (6)	0.20171 (10)	0.0368 (7)
C11	0.8542 (5)	0.2972 (6)	0.23870 (9)	0.0371 (6)
C12	0.6027 (5)	0.5289 (6)	0.34255 (9)	0.0366 (7)
C13	0.6956 (6)	0.7103 (6)	0.38002 (9)	0.0355 (7)
C14	0.5666 (7)	0.6932 (7)	0.42123 (10)	0.0474 (8)
H14A	0.4253	0.5694	0.4251	0.057*
C15	0.9033 (6)	0.8972 (7)	0.37430 (10)	0.0432 (7)
H15A	0.9915	0.9099	0.3466	0.052*
C16	0.9798 (7)	1.0656 (7)	0.40988 (12)	0.0536 (9)
H16A	1.1171	1.1933	0.4058	0.064*
C17	0.8531 (7)	1.0442 (7)	0.45115 (11)	0.0530 (9)
H17A	0.9074	1.1549	0.4752	0.064*
C18	0.6461 (7)	0.8593 (8)	0.45684 (11)	0.0526 (9)
H18A	0.5595	0.8457	0.4846	0.063*
N1	0.7200 (5)	0.2895 (6)	0.27768 (8)	0.0417 (6)
H1B	0.5876	0.1768	0.2812	0.050*
N2	0.7938 (4)	0.4635 (6)	0.31267 (7)	0.0410 (6)
H2B	0.9596	0.5276	0.3150	0.049*
O1	0.4183 (4)	−0.1167 (5)	0.24650 (6)	0.0469 (6)
H1C	0.3089	−0.2417	0.2447	0.070*
O2	1.0522 (4)	0.4497 (5)	0.23390 (7)	0.0525 (6)
O3	0.3630 (4)	0.4405 (6)	0.33929 (7)	0.0533 (6)

	U11	U22	U33	U12	U13	U23
C1	0.071 (2)	0.064 (2)	0.0394 (16)	−0.001 (2)	0.0079 (16)	−0.0050 (18)
C2	0.084 (3)	0.065 (2)	0.0450 (18)	−0.024 (2)	0.0158 (17)	−0.0074 (19)
C3	0.071 (2)	0.065 (2)	0.058 (2)	−0.027 (2)	0.0076 (18)	−0.018 (2)
C4	0.067 (2)	0.069 (3)	0.0462 (19)	−0.005 (2)	−0.0014 (17)	−0.0179 (19)
C5	0.0429 (15)	0.0430 (18)	0.0419 (15)	−0.0036 (15)	−0.0031 (12)	−0.0026 (16)
C6	0.0459 (15)	0.0458 (19)	0.0399 (15)	−0.0031 (16)	0.0028 (13)	−0.0007 (16)
C7	0.0528 (18)	0.049 (2)	0.0455 (17)	−0.0197 (17)	0.0061 (14)	−0.0033 (17)
C8	0.0546 (19)	0.0474 (19)	0.0517 (19)	−0.0214 (17)	0.0055 (15)	−0.0060 (17)
C9	0.0339 (13)	0.0352 (16)	0.0394 (14)	−0.0045 (13)	0.0016 (11)	0.0005 (14)
C10	0.0342 (14)	0.0363 (15)	0.0400 (15)	−0.0056 (13)	−0.0002 (12)	−0.0017 (14)
C11	0.0318 (13)	0.0403 (16)	0.0394 (14)	−0.0060 (13)	0.0015 (11)	−0.0003 (14)
C12	0.0287 (13)	0.0412 (16)	0.0400 (15)	−0.0019 (12)	0.0010 (11)	−0.0013 (14)
C13	0.0306 (13)	0.0372 (17)	0.0386 (15)	0.0016 (12)	−0.0010 (11)	−0.0003 (14)
C14	0.0453 (18)	0.051 (2)	0.0463 (18)	−0.0070 (16)	0.0065 (14)	−0.0036 (17)
C15	0.0416 (15)	0.0419 (18)	0.0465 (16)	−0.0018 (15)	0.0074 (12)	0.0006 (16)
C16	0.0467 (18)	0.045 (2)	0.069 (2)	−0.0092 (16)	0.0009 (16)	−0.0090 (19)
C17	0.059 (2)	0.0464 (19)	0.0534 (19)	0.0016 (17)	−0.0068 (16)	−0.0136 (18)
C18	0.0584 (19)	0.057 (2)	0.0426 (16)	−0.0035 (18)	0.0054 (15)	−0.0079 (17)
N1	0.0357 (12)	0.0460 (15)	0.0437 (14)	−0.0133 (12)	0.0058 (10)	−0.0105 (14)
N2	0.0301 (10)	0.0526 (16)	0.0405 (12)	−0.0084 (12)	0.0027 (9)	−0.0116 (13)
O1	0.0505 (12)	0.0464 (13)	0.0443 (11)	−0.0205 (11)	0.0082 (9)	−0.0030 (11)
O2	0.0529 (12)	0.0588 (15)	0.0463 (11)	−0.0268 (12)	0.0101 (9)	−0.0080 (12)
O3	0.0277 (9)	0.0729 (16)	0.0592 (12)	−0.0083 (11)	0.0034 (9)	−0.0176 (14)

C1—C2	1.357 (5)	C11—N1	1.331 (4)
C1—C4	1.385 (5)	C12—O3	1.235 (3)
C1—H1A	0.9300	C12—N2	1.330 (3)
C2—C6	1.417 (4)	C12—C13	1.489 (4)
C2—H2A	0.9300	C13—C14	1.379 (4)
C3—C4	1.356 (5)	C13—C15	1.384 (4)
C3—C5	1.415 (5)	C14—C18	1.384 (4)
C3—H3A	0.9300	C14—H14A	0.9300
C4—H4A	0.9300	C15—C16	1.387 (4)
C5—C6	1.399 (5)	C15—H15A	0.9300
C5—C8	1.411 (4)	C16—C17	1.377 (5)
C6—C7	1.410 (4)	C16—H16A	0.9300
C7—C10	1.369 (4)	C17—C18	1.374 (5)
C7—H7A	0.9300	C17—H17A	0.9300
C8—C9	1.359 (4)	C18—H18A	0.9300
C8—H8A	0.9300	N1—N2	1.388 (3)
C9—O1	1.373 (3)	N1—H1B	0.8600
C9—C10	1.417 (4)	N2—H2B	0.8600
C10—C11	1.497 (4)	O1—H1C	0.8200
C11—O2	1.233 (3)
C2—C1—C4	120.2 (3)	O2—C11—C10	122.4 (3)
C2—C1—H1A	119.9	N1—C11—C10	117.0 (2)
C4—C1—H1A	119.9	O3—C12—N2	121.3 (3)
C1—C2—C6	121.1 (3)	O3—C12—C13	122.5 (3)
C1—C2—H2A	119.5	N2—C12—C13	116.2 (2)
C6—C2—H2A	119.5	C14—C13—C15	119.5 (3)
C4—C3—C5	121.3 (4)	C14—C13—C12	118.6 (3)
C4—C3—H3A	119.3	C15—C13—C12	121.9 (3)
C5—C3—H3A	119.3	C13—C14—C18	120.4 (3)
C3—C4—C1	120.3 (3)	C13—C14—H14A	119.8
C3—C4—H4A	119.8	C18—C14—H14A	119.8
C1—C4—H4A	119.8	C13—C15—C16	119.9 (3)
C6—C5—C8	118.8 (3)	C13—C15—H15A	120.0
C6—C5—C3	118.3 (3)	C16—C15—H15A	120.0
C8—C5—C3	122.9 (3)	C17—C16—C15	120.2 (3)
C5—C6—C7	118.1 (3)	C17—C16—H16A	119.9
C5—C6—C2	118.8 (3)	C15—C16—H16A	119.9
C7—C6—C2	123.1 (3)	C18—C17—C16	119.9 (3)
C10—C7—C6	123.0 (3)	C18—C17—H17A	120.0
C10—C7—H7A	118.5	C16—C17—H17A	120.0
C6—C7—H7A	118.5	C17—C18—C14	120.1 (3)
C9—C8—C5	122.0 (3)	C17—C18—H18A	120.0
C9—C8—H8A	119.0	C14—C18—H18A	120.0
C5—C8—H8A	119.0	C11—N1—N2	120.0 (2)
C8—C9—O1	120.9 (3)	C11—N1—H1B	120.0
C8—C9—C10	120.0 (3)	N2—N1—H1B	120.0
O1—C9—C10	119.1 (2)	C12—N2—N1	118.5 (2)
C7—C10—C9	118.1 (3)	C12—N2—H2B	120.7
C7—C10—C11	115.9 (3)	N1—N2—H2B	120.7
C9—C10—C11	126.0 (2)	C9—O1—H1C	109.5
O2—C11—N1	120.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···O2i	0.82	2.00	2.818 (3)	174
N1—H1B···O1	0.86	1.96	2.652 (4)	137
N2—H2B···O3ii	0.86	2.09	2.826 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1C⋯O2i	0.82	2.00	2.818 (3)	174
N1—H1B⋯O1	0.86	1.96	2.652 (4)	137
N2—H2B⋯O3ii	0.86	2.09	2.826 (3)	143

Symmetry codes: (i) ; (ii) .