(E)-N'-[(2-Hy-droxy-naphthalen-1-yl)methyl-idene]-4-methyl-benzene-sulfono-hydrazide.

In the title compound, C(18)H(16)N(2)O(3)S, the dihedral angle between the planes of the benzene ring and the naphthyl ring system is 83.37 (10)°. An intra-molecular O-H⋯N hydrogen bond occurs. Inter-molecular N-H⋯O hydrogen bonds stabilize the crystal structure. There is a π-π inter-action between the naphthyl ring systems [centroid-centroid distance = 3.7556 (15) Å]. In addition, naphth-yl-tolyl and naphth-yl-naphthyl C-H⋯π inter-actions are observed.

Related literature

For related structures, see: Bikas et al. (2010 ▶); Silva et al. (2006 ▶); Zimmer et al. (1959 ▶).

Experimental

Crystal data

C18H16N2O3S

M = 340.40

Monoclinic,

a = 15.740 (3) Å

b = 10.573 (2) Å

c = 10.322 (2) Å

β = 103.86 (3)°

V = 1667.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 298 K

0.35 × 0.25 × 0.2 mm

Data collection

Stoe IPDS 2T diffractometer

Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005 ▶) T min = 0.935, T max = 0.957

13245 measured reflections

4474 independent reflections

2439 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.143

S = 0.92

4474 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.28 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811006088/vm2077sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006088/vm2077Isup2.hkl

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

C18H16N2O3S	F(000) = 712
Mr = 340.40	Dx = 1.356 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4474 reflections
a = 15.740 (3) Å	θ = 2.3–29.2°
b = 10.573 (2) Å	µ = 0.21 mm−1
c = 10.322 (2) Å	T = 298 K
β = 103.86 (3)°	Plate, yellow
V = 1667.8 (6) Å3	0.35 × 0.25 × 0.2 mm
Z = 4

Stoe IPDS 2T diffractometer	4474 independent reflections
Radiation source: fine-focus sealed tube	2439 reflections with I > 2σ(I)
graphite	Rint = 0.080
Detector resolution: 0.15 mm pixels mm-1	θmax = 29.2°, θmin = 2.3°
rotation method scans	h = −21→21
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005)	k = −14→13
Tmin = 0.935, Tmax = 0.957	l = −13→14
13245 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 0.92	w = 1/[σ2(Fo2) + (0.0771P)2] where P = (Fo2 + 2Fc2)/3
4474 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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
C6	0.41858 (14)	0.4904 (3)	0.3196 (2)	0.0705 (8)
H6	0.4426	0.4414	0.2626	0.085*
S1	0.34568 (3)	0.27206 (7)	0.38051 (5)	0.0577 (2)
O2	0.31790 (11)	0.23002 (19)	0.49498 (15)	0.0713 (5)
N1	0.26101 (10)	0.25594 (19)	0.25177 (17)	0.0534 (5)
H1A	0.2632	0.2147	0.1808	0.064*
O1	0.41463 (10)	0.2084 (2)	0.34045 (19)	0.0783 (6)
N2	0.18558 (10)	0.31574 (17)	0.26935 (16)	0.0474 (4)
C8	0.11925 (12)	0.3191 (2)	0.16968 (19)	0.0436 (5)
H8	0.1228	0.2816	0.0896	0.052*
C9	0.03862 (12)	0.38038 (19)	0.17943 (18)	0.0414 (4)
O3	0.10297 (10)	0.45363 (19)	0.40269 (14)	0.0656 (5)
H3	0.1464	0.4217	0.3853	0.098*
C18	−0.03826 (12)	0.37537 (19)	0.07041 (19)	0.0429 (4)
C7	0.36860 (12)	0.4348 (3)	0.39778 (19)	0.0553 (6)
C17	−0.04179 (15)	0.3112 (2)	−0.0504 (2)	0.0539 (6)
H17	0.0077	0.2688	−0.0618	0.065*
C10	0.03447 (13)	0.4460 (2)	0.29415 (19)	0.0489 (5)
C1	0.33366 (15)	0.5089 (3)	0.4823 (2)	0.0660 (7)
H1	0.3007	0.4723	0.5361	0.079*
C11	−0.04155 (15)	0.5093 (2)	0.3048 (2)	0.0610 (6)
H11	−0.0425	0.5538	0.3821	0.073*
C15	−0.19112 (16)	0.3721 (3)	−0.1373 (3)	0.0675 (7)
H15	−0.2415	0.3704	−0.2062	0.081*
C13	−0.11516 (13)	0.4395 (2)	0.0837 (2)	0.0500 (5)
C14	−0.19068 (14)	0.4359 (3)	−0.0229 (3)	0.0637 (7)
H14	−0.2410	0.4779	−0.0145	0.076*
C12	−0.11397 (15)	0.5057 (2)	0.2025 (2)	0.0598 (6)
H12	−0.1641	0.5481	0.2110	0.072*
C16	−0.11621 (17)	0.3097 (3)	−0.1513 (2)	0.0653 (7)
H16	−0.1166	0.2664	−0.2299	0.078*
C3	0.39614 (15)	0.6954 (3)	0.4084 (3)	0.0700 (8)
C5	0.43222 (16)	0.6196 (3)	0.3274 (3)	0.0787 (9)
H5	0.4668	0.6565	0.2762	0.094*
C2	0.34799 (17)	0.6369 (3)	0.4863 (3)	0.0738 (8)
H2	0.3243	0.6860	0.5437	0.089*
C4	0.4090 (2)	0.8355 (4)	0.4087 (4)	0.0969 (10)
H4A	0.3725	0.8711	0.3290	0.145*
H4B	0.4692	0.8539	0.4117	0.145*
H4C	0.3937	0.8715	0.4854	0.145*

	U11	U22	U33	U12	U13	U23
C6	0.0495 (12)	0.105 (3)	0.0628 (15)	0.0036 (13)	0.0256 (11)	0.0034 (14)
S1	0.0488 (3)	0.0843 (5)	0.0418 (3)	0.0121 (3)	0.0145 (2)	0.0078 (3)
O2	0.0796 (10)	0.0930 (15)	0.0447 (9)	0.0094 (9)	0.0215 (8)	0.0149 (8)
N1	0.0489 (9)	0.0698 (14)	0.0440 (9)	0.0081 (8)	0.0159 (7)	−0.0049 (9)
O1	0.0576 (9)	0.1076 (16)	0.0717 (11)	0.0291 (9)	0.0196 (8)	0.0054 (10)
N2	0.0468 (8)	0.0557 (12)	0.0426 (9)	0.0048 (7)	0.0168 (7)	0.0009 (8)
C8	0.0503 (10)	0.0455 (13)	0.0370 (10)	0.0002 (9)	0.0145 (8)	0.0005 (8)
C9	0.0483 (10)	0.0396 (12)	0.0377 (9)	0.0012 (8)	0.0133 (8)	0.0014 (8)
O3	0.0641 (9)	0.0914 (14)	0.0413 (8)	0.0074 (9)	0.0124 (7)	−0.0137 (8)
C18	0.0508 (10)	0.0363 (12)	0.0429 (10)	0.0012 (8)	0.0138 (8)	0.0052 (8)
C7	0.0388 (9)	0.0851 (19)	0.0410 (10)	0.0006 (10)	0.0075 (8)	0.0010 (11)
C17	0.0605 (12)	0.0487 (14)	0.0489 (12)	0.0027 (10)	0.0059 (9)	−0.0041 (10)
C10	0.0554 (11)	0.0537 (14)	0.0398 (10)	0.0019 (9)	0.0157 (9)	0.0001 (9)
C1	0.0621 (13)	0.092 (2)	0.0478 (12)	−0.0105 (13)	0.0207 (10)	−0.0082 (12)
C11	0.0748 (15)	0.0609 (17)	0.0533 (13)	0.0125 (12)	0.0269 (11)	−0.0063 (11)
C15	0.0601 (13)	0.0675 (19)	0.0645 (15)	−0.0075 (12)	−0.0053 (11)	0.0088 (13)
C13	0.0517 (11)	0.0447 (14)	0.0549 (12)	0.0014 (9)	0.0151 (9)	0.0091 (10)
C14	0.0495 (11)	0.0630 (18)	0.0763 (16)	0.0046 (11)	0.0106 (11)	0.0169 (13)
C12	0.0584 (12)	0.0594 (16)	0.0669 (15)	0.0153 (11)	0.0255 (11)	0.0050 (12)
C16	0.0759 (15)	0.0604 (17)	0.0513 (13)	−0.0027 (12)	−0.0011 (11)	−0.0032 (11)
C3	0.0472 (12)	0.096 (2)	0.0622 (15)	−0.0087 (12)	0.0032 (11)	0.0008 (14)
C5	0.0523 (13)	0.105 (3)	0.0819 (19)	−0.0119 (14)	0.0222 (13)	0.0181 (17)
C2	0.0712 (15)	0.094 (2)	0.0565 (14)	−0.0097 (15)	0.0160 (12)	−0.0129 (14)
C4	0.0861 (19)	0.099 (3)	0.098 (2)	−0.0163 (18)	0.0068 (17)	0.0056 (19)

C6—C5	1.383 (4)	C10—C11	1.398 (3)
C6—C7	1.386 (3)	C1—C2	1.370 (4)
C6—H6	0.9300	C1—H1	0.9300
S1—O1	1.4204 (17)	C11—C12	1.356 (3)
S1—O2	1.4257 (17)	C11—H11	0.9300
S1—N1	1.6499 (18)	C15—C14	1.359 (4)
S1—C7	1.758 (3)	C15—C16	1.389 (4)
N1—N2	1.395 (2)	C15—H15	0.9300
N1—H1A	0.8600	C13—C12	1.408 (3)
N2—C8	1.279 (2)	C13—C14	1.413 (3)
C8—C9	1.450 (3)	C14—H14	0.9300
C8—H8	0.9300	C12—H12	0.9300
C9—C10	1.387 (3)	C16—H16	0.9300
C9—C18	1.443 (3)	C3—C5	1.375 (4)
O3—C10	1.358 (2)	C3—C2	1.376 (4)
O3—H3	0.8200	C3—C4	1.496 (5)
C18—C17	1.409 (3)	C5—H5	0.9300
C18—C13	1.422 (3)	C2—H2	0.9300
C7—C1	1.382 (3)	C4—H4A	0.9600
C17—C16	1.368 (3)	C4—H4B	0.9600
C17—H17	0.9300	C4—H4C	0.9600
C5—C6—C7	119.2 (3)	C7—C1—H1	120.3
C5—C6—H6	120.4	C12—C11—C10	120.1 (2)
C7—C6—H6	120.4	C12—C11—H11	120.0
O1—S1—O2	120.06 (12)	C10—C11—H11	120.0
O1—S1—N1	104.04 (10)	C14—C15—C16	119.9 (2)
O2—S1—N1	106.64 (10)	C14—C15—H15	120.1
O1—S1—C7	109.94 (12)	C16—C15—H15	120.1
O2—S1—C7	108.50 (11)	C12—C13—C14	121.6 (2)
N1—S1—C7	106.82 (10)	C12—C13—C18	119.13 (18)
N2—N1—S1	113.38 (13)	C14—C13—C18	119.3 (2)
N2—N1—H1A	123.3	C15—C14—C13	121.2 (2)
S1—N1—H1A	123.3	C15—C14—H14	119.4
C8—N2—N1	117.67 (17)	C13—C14—H14	119.4
N2—C8—C9	121.08 (18)	C11—C12—C13	121.7 (2)
N2—C8—H8	119.5	C11—C12—H12	119.2
C9—C8—H8	119.5	C13—C12—H12	119.2
C10—C9—C18	118.81 (18)	C17—C16—C15	120.6 (2)
C10—C9—C8	120.25 (17)	C17—C16—H16	119.7
C18—C9—C8	120.94 (17)	C15—C16—H16	119.7
C10—O3—H3	109.5	C5—C3—C2	117.3 (3)
C17—C18—C13	117.44 (18)	C5—C3—C4	120.1 (3)
C17—C18—C9	123.77 (18)	C2—C3—C4	122.5 (3)
C13—C18—C9	118.79 (18)	C3—C5—C6	122.0 (3)
C1—C7—C6	119.7 (3)	C3—C5—H5	119.0
C1—C7—S1	121.08 (19)	C6—C5—H5	119.0
C6—C7—S1	119.2 (2)	C1—C2—C3	122.4 (3)
C16—C17—C18	121.6 (2)	C1—C2—H2	118.8
C16—C17—H17	119.2	C3—C2—H2	118.8
C18—C17—H17	119.2	C3—C4—H4A	109.5
O3—C10—C9	122.90 (18)	C3—C4—H4B	109.5
O3—C10—C11	115.60 (19)	H4A—C4—H4B	109.5
C9—C10—C11	121.50 (19)	C3—C4—H4C	109.5
C2—C1—C7	119.4 (2)	H4A—C4—H4C	109.5
C2—C1—H1	120.3	H4B—C4—H4C	109.5
O1—S1—N1—N2	−178.38 (16)	C8—C9—C10—C11	178.0 (2)
O2—S1—N1—N2	53.77 (18)	C6—C7—C1—C2	0.9 (3)
C7—S1—N1—N2	−62.10 (17)	S1—C7—C1—C2	−175.48 (18)
S1—N1—N2—C8	173.14 (15)	O3—C10—C11—C12	−179.0 (2)
N1—N2—C8—C9	−179.48 (18)	C9—C10—C11—C12	1.1 (4)
N2—C8—C9—C10	5.5 (3)	C17—C18—C13—C12	−179.4 (2)
N2—C8—C9—C18	−175.04 (19)	C9—C18—C13—C12	0.0 (3)
C10—C9—C18—C17	−179.7 (2)	C17—C18—C13—C14	0.2 (3)
C8—C9—C18—C17	0.8 (3)	C9—C18—C13—C14	179.6 (2)
C10—C9—C18—C13	0.9 (3)	C16—C15—C14—C13	−0.4 (4)
C8—C9—C18—C13	−178.56 (19)	C12—C13—C14—C15	179.7 (2)
C5—C6—C7—C1	−0.3 (3)	C18—C13—C14—C15	0.1 (4)
C5—C6—C7—S1	176.16 (18)	C10—C11—C12—C13	−0.1 (4)
O1—S1—C7—C1	−154.14 (17)	C14—C13—C12—C11	180.0 (2)
O2—S1—C7—C1	−21.0 (2)	C18—C13—C12—C11	−0.4 (4)
N1—S1—C7—C1	93.57 (18)	C18—C17—C16—C15	0.1 (4)
O1—S1—C7—C6	29.5 (2)	C14—C15—C16—C17	0.3 (4)
O2—S1—C7—C6	162.58 (17)	C2—C3—C5—C6	2.3 (4)
N1—S1—C7—C6	−82.81 (18)	C4—C3—C5—C6	−177.0 (2)
C13—C18—C17—C16	−0.3 (3)	C7—C6—C5—C3	−1.4 (4)
C9—C18—C17—C16	−179.7 (2)	C7—C1—C2—C3	0.1 (4)
C18—C9—C10—O3	178.6 (2)	C5—C3—C2—C1	−1.7 (4)
C8—C9—C10—O3	−1.9 (3)	C4—C3—C2—C1	177.6 (2)
C18—C9—C10—C11	−1.5 (3)

Cg1 and Cg2 are the centroids of the C1–C3/C5–C7 and C9–C13/C18 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.82	1.85	2.563 (2)	145.
N1—H1A···O2i	0.86	2.36	2.998 (2)	132.
C15—H15···Cg1ii	0.92	2.72	3.625 (3)	164
C16—H16···Cg2i	0.92	2.75	3.501 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C3/C5–C7 and C9–C13/C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2	0.82	1.85	2.563 (2)	145
N1—H1A⋯O2i	0.86	2.36	2.998 (2)	132
C15—H15⋯Cg1ii	0.92	2.72	3.625 (3)	164
C16—H16⋯Cg2i	0.92	2.75	3.501 (3)	139

Symmetry codes: (i) ; (ii) .