(E)-N′-[(2-Hy­droxy­naphthalen-1-yl)methyl­idene]-4-methyl­benzene­sulfono­hydrazide

Shahverdizadeh, G.H.; Bikas, R.; Eivazi, M.; Mahboubi Anarjan, P.; Notash, B.

doi:10.1107/S1600536811006088

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o713

doi:10.1107/S1600536811006088

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(E)-N′-[(2-Hydroxynaphthalen-1-yl)methylidene]-4-methylbenzenesulfonohydrazide

Gholam Hossein Shahverdizadeh,^a ^* Rahman Bikas,^a Maryam Eivazi,^a Parisa Mahboubi Anarjan ^a and Behrouz Notash ^b

^aDepartment of Applied Chemistry, Research Laboratory, Islamic Azad University, Tabriz Branch, Tabriz, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: shahverdizadeh@iaut.ac.ir

(Received 26 January 2011; accepted 17 February 2011; online 26 February 2011)

In the title compound, C₁₈H₁₆N₂O₃S, the dihedral angle between the planes of the benzene ring and the naphthyl ring system is 83.37 (10)°. An intramolecular O—H⋯N hydrogen bond occurs. Intermolecular N—H⋯O hydrogen bonds stabilize the crystal structure. There is a π–π interaction between the naphthyl ring systems [centroid–centroid distance = 3.7556 (15) Å]. In addition, naphthyl–tolyl and naphthyl–naphthyl C—H⋯π interactions 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_r = 340.40
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.143
S = 0.92
4474 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Sulfonyl hydrazones are found to exhibit large medicinal applications. Similar to sulfonamides, sulfonyl hydrazones also have various biological activities. For example, imidosulfonylhydrazones have antibacterial and antineociceptive properties (Silva et al., 2006). Acidic sulfonyl hydrazone derivatives have analgesic and anti-inflammatory activities. 4-Substituted benzenesulfonylhydrazone has been found to have antibacterial activity (Zimmer et al., 1959).

As part of our studies on the synthesis and characterization of hydrazone derivatives (Bikas et al., 2010), we report here the crystal structure of (E)-N'-((2-hydroxynaphthalen-1-yl)methylene)-4-methylbenzenesulfonohydrazide. The asymmetric unit of the title compound contains one molecule, which is shown in Fig. 1. The packing diagram of the title compound is shown in Fig. 2. The structure is stabilized by an intramolecular O—H···N hydrogen bond, with the nitrogen of the azomethine group (–C=N–) acting as hydrogen bond acceptor and intermolecular N—H···O hydrogen bonds with the S=O group as hydrogen bond acceptor (Table 1 and Fig. 2). The packing is characterized by a π-π interaction between the naphthyl rings (Fig. 3) with Cg2···Cg3ⁱⁱ distance = 3.7556 (15) Å where Cg2 and Cg3 are the centroids of C9-C13/C18 and C13-C18, respectively (symmetry code ii: -x,1 - y,-z). Furthermore, C—H_naphthyl···π_tolyl and C—H_naphthyl···π_naphthyl interactions are observed with distances equal to 2.72 and 2.75 Å, respectively (Table 1 & Fig. 3).

Related literature top

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

Experimental top

All reagents were commercially available and used as received. A methanol (10 ml) solution of 2-hydroxy-1-naphtaldehyde (1.63 mmol) was dropwise added to a methanol solution (10 ml) of 4-methyl-benzenesulfonic acid hydrazide (1.63 mmol), and the mixture was refluxed for 3 hrs. Then the solution was evaporated on a steam bath to 5 ml and cooled to room temperature. A yellow precipitate of the title compound was separated and filtered off, washed with 5 ml of cooled methanol and then dried in air. X-ray quality crystals of the title compound were obtained from methanol by slow solvent evaporation. Yield: 81%, mp: 167.8–168.2 °C.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); 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).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 30% probability level) for non-H atoms.
	Fig. 2. The packing diagram of the title compound. Hydrogen bonds are shown as blue dashed line.
	Fig. 3. The packing diagram of the title compound showing π-π and C—H···π interactions as blue and orange dashed lines, respectively. Cg1, Cg2 and Cg3 are the centroids of rings C1-C3/C5-C7, C9-C13/C18 and C13-C18, respectively; symmetry codes: (i) x, -y + 1/2, z - 1/2; (ii) -x, -y + 1, -z.).

(E)-N'-[(2-Hydroxynaphthalen-1-yl)methylidene]-4- methylbenzenesulfonohydrazide top

Crystal data top

C₁₈H₁₆N₂O₃S	F(000) = 712
M_r = 340.40	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0771P)²] where P = (F_o² + 2F_c²)/3
4474 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₈H₁₆N₂O₃S	V = 1667.8 (6) Å³
M_r = 340.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.740 (3) Å	µ = 0.21 mm⁻¹
b = 10.573 (2) Å	T = 298 K
c = 10.322 (2) Å	0.35 × 0.25 × 0.2 mm
β = 103.86 (3)°

Data collection top

Stoe IPDS 2T diffractometer	4474 independent reflections
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005)	2439 reflections with I > 2σ(I)
T_min = 0.935, T_max = 0.957	R_int = 0.080
13245 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 0.92	Δρ_max = 0.35 e Å⁻³
4474 reflections	Δρ_min = −0.28 e Å⁻³
219 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z−1/2; (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₂O₃S
M_r	340.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	15.740 (3), 10.573 (2), 10.322 (2)
β (°)	103.86 (3)
V (Å³)	1667.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.35 × 0.25 × 0.2

Data collection
Diffractometer	Stoe IPDS 2T diffractometer
Absorption correction	Numerical (X-SHAPE; Stoe & Cie, 2005)
T_min, T_max	0.935, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	13245, 4474, 2439
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.143, 0.92
No. of reflections	4474
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.28

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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)	144.7
N1—H1A···O2ⁱ	0.86	2.36	2.998 (2)	131.6
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) x, −y+1/2, z−1/2; (ii) −x, −y+1, −z.

Acknowledgements

The authors are grateful to the Islamic Azad University, Tabriz Branch, and Shahid Beheshti University for financial support.

References

Bikas, R., Hosseini Monfared, H., Bijanzad, K., Koroglu, A. & Kazak, C. (2010). Acta Cryst. E66, o2073. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Silva, L. L., Oliveira, K. N. & Nunes, R. J. (2006). ARKIVOC, 13, 124–129. CrossRef Google Scholar
Stoe & Cie (2005). X-AREA and X-SHAPE. Stoe & Cie, Darmstadt, Germany. Google Scholar
Zimmer, H., Benjamin, B. H., Gerlach, E. H., Fry, K., Pronay, A. C. & Schmank, H. (1959). J. Org. Chem. 24, 1667–1669. CrossRef CAS Google Scholar

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Volume 67| Part 3| March 2011| Page o713

doi:10.1107/S1600536811006088

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

(E)-N′-[(2-Hy­dr­oxy­naphthalen-1-yl)methyl­­idene]-4-methyl­benzene­sulfono­hydrazide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

(E)-N′-[(2-Hydroxynaphthalen-1-yl)methylidene]-4-methylbenzenesulfonohydrazide