N-(1-Naphth-yl)benzene-sulfonamide.

In the title compound, C(16)H(13)NO(2)S, the C-SO(2)-NH-C torsion angle is -70.1 (2)°. The dihedral angle between the planes of the naphthyl ring system and the phenyl ring is 34.67 (4)°. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds into chains along [100]. There are also π-π inter-actions between adjacent naphthyl groups [inter-planar spacing = 3.541 (3) Å] for mol-ecules stacked along [100].

Related literature

For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001 ▶). For related structures, see: Shakuntala et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H13NO2S

M = 283.33

Orthorhombic,

a = 4.9232 (5) Å

b = 15.4162 (15) Å

c = 18.2102 (17) Å

V = 1382.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 298 K

0.43 × 0.33 × 0.32 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.906, T max = 0.929

6917 measured reflections

2438 independent reflections

2178 reflections with I > σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.084

S = 1.09

2438 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 983 Friedel pairs

Flack parameter: 0.06 (9)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039201/pk2348sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039201/pk2348Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039201/pk2348Isup3.cml

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

C16H13NO2S	F(000) = 592
Mr = 283.33	Dx = 1.362 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3370 reflections
a = 4.9232 (5) Å	θ = 2.6–26.0°
b = 15.4162 (15) Å	µ = 0.23 mm−1
c = 18.2102 (17) Å	T = 298 K
V = 1382.1 (2) Å3	Block-like, colorless
Z = 4	0.43 × 0.33 × 0.32 mm

Bruker SMART CCD area-detector diffractometer	2438 independent reflections
Radiation source: fine-focus sealed tube	2178 reflections with I > σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −5→5
Tmin = 0.906, Tmax = 0.929	k = −17→18
6917 measured reflections	l = −14→21

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.037P)2 + 0.2812P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.084	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.18 e Å−3
2438 reflections	Δρmin = −0.20 e Å−3
182 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.038 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 983 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.06 (9)

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
S1	0.63000 (11)	0.47539 (3)	0.28894 (3)	0.03525 (17)
N1	0.7982 (4)	0.50023 (12)	0.36336 (10)	0.0388 (5)
H1	0.9726	0.4850	0.3559	0.047*
O1	0.3486 (3)	0.48108 (11)	0.30720 (9)	0.0496 (4)
O2	0.7374 (3)	0.52862 (11)	0.23221 (9)	0.0486 (4)
C1	0.7144 (5)	0.46260 (17)	0.43237 (13)	0.0430 (6)
C2	0.8252 (6)	0.38695 (18)	0.45628 (15)	0.0574 (7)
H2	0.9547	0.3589	0.4277	0.069*
C3	0.7467 (9)	0.3508 (2)	0.52341 (18)	0.0800 (11)
H3	0.8277	0.2999	0.5400	0.096*
C4	0.5555 (9)	0.3894 (3)	0.56351 (18)	0.0824 (12)
H4	0.4994	0.3634	0.6070	0.099*
C5	0.4352 (6)	0.4686 (3)	0.54214 (14)	0.0673 (9)
C6	0.5182 (5)	0.50785 (18)	0.47415 (13)	0.0503 (7)
C7	0.4088 (6)	0.5887 (2)	0.45330 (16)	0.0617 (8)
H7	0.4671	0.6155	0.4103	0.074*
C8	0.2160 (7)	0.6281 (3)	0.4966 (2)	0.0894 (12)
H8	0.1439	0.6815	0.4831	0.107*
C9	0.1278 (8)	0.5871 (4)	0.5617 (2)	0.1007 (15)
H9	−0.0060	0.6132	0.5902	0.121*
C10	0.2347 (8)	0.5107 (4)	0.5831 (2)	0.0960 (14)
H10	0.1733	0.4853	0.6264	0.115*
C11	0.6966 (5)	0.36643 (14)	0.26609 (12)	0.0375 (6)
C12	0.8977 (6)	0.34830 (16)	0.21627 (15)	0.0541 (6)
H12	0.9960	0.3927	0.1942	0.065*
C13	0.9509 (7)	0.2619 (2)	0.19960 (19)	0.0767 (10)
H13	1.0869	0.2477	0.1663	0.092*
C14	0.7995 (8)	0.1971 (2)	0.2331 (2)	0.0815 (12)
H14	0.8348	0.1393	0.2220	0.098*
C15	0.6022 (8)	0.21681 (18)	0.28156 (19)	0.0747 (9)
H15	0.5027	0.1725	0.3034	0.090*
C16	0.5467 (6)	0.30098 (16)	0.29891 (15)	0.0553 (7)
H16	0.4100	0.3143	0.3323	0.066*

	U11	U22	U33	U12	U13	U23
S1	0.0321 (3)	0.0373 (3)	0.0364 (3)	0.0023 (3)	0.0012 (2)	0.0003 (3)
N1	0.0274 (10)	0.0482 (11)	0.0407 (10)	−0.0036 (7)	0.0033 (8)	−0.0040 (8)
O1	0.0304 (8)	0.0613 (10)	0.0570 (10)	0.0060 (9)	−0.0004 (8)	−0.0087 (9)
O2	0.0576 (10)	0.0435 (8)	0.0448 (9)	0.0013 (9)	0.0034 (8)	0.0097 (8)
C1	0.0377 (13)	0.0569 (15)	0.0344 (12)	−0.0124 (12)	−0.0021 (10)	−0.0027 (11)
C2	0.0598 (18)	0.0633 (17)	0.0491 (15)	−0.0032 (14)	−0.0107 (14)	0.0038 (13)
C3	0.105 (3)	0.079 (2)	0.055 (2)	−0.016 (2)	−0.009 (2)	0.0166 (17)
C4	0.101 (3)	0.104 (3)	0.0423 (18)	−0.044 (2)	−0.0106 (19)	0.0179 (18)
C5	0.0537 (18)	0.114 (3)	0.0340 (13)	−0.0348 (19)	0.0049 (13)	−0.0198 (17)
C6	0.0384 (13)	0.0705 (18)	0.0420 (13)	−0.0158 (13)	0.0000 (11)	−0.0140 (12)
C7	0.0512 (18)	0.083 (2)	0.0513 (16)	−0.0034 (15)	0.0029 (14)	−0.0252 (15)
C8	0.067 (2)	0.119 (3)	0.082 (2)	0.020 (2)	−0.0036 (19)	−0.046 (2)
C9	0.058 (2)	0.178 (4)	0.066 (2)	−0.009 (3)	0.020 (2)	−0.067 (3)
C10	0.070 (2)	0.161 (4)	0.057 (2)	−0.042 (3)	0.0155 (18)	−0.034 (3)
C11	0.0370 (13)	0.0366 (11)	0.0389 (12)	0.0012 (10)	−0.0069 (10)	−0.0002 (9)
C12	0.0507 (15)	0.0522 (13)	0.0594 (15)	0.0053 (13)	0.0022 (15)	−0.0121 (13)
C13	0.064 (2)	0.075 (2)	0.091 (2)	0.0250 (17)	−0.0058 (19)	−0.0371 (19)
C14	0.089 (3)	0.0419 (15)	0.113 (3)	0.0147 (17)	−0.046 (2)	−0.0218 (18)
C15	0.092 (2)	0.0398 (14)	0.092 (2)	−0.0081 (16)	−0.021 (2)	0.0030 (16)
C16	0.0582 (17)	0.0461 (14)	0.0615 (17)	−0.0063 (12)	−0.0032 (15)	0.0029 (13)

S1—O2	1.4214 (16)	C7—H7	0.9300
S1—O1	1.4273 (17)	C8—C9	1.411 (6)
S1—N1	1.6337 (19)	C8—H8	0.9300
S1—C11	1.761 (2)	C9—C10	1.348 (6)
N1—C1	1.444 (3)	C9—H9	0.9300
N1—H1	0.9000	C10—H10	0.9300
C1—C2	1.359 (4)	C11—C12	1.372 (3)
C1—C6	1.414 (4)	C11—C16	1.386 (3)
C2—C3	1.398 (4)	C12—C13	1.391 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.332 (5)	C13—C14	1.388 (5)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.411 (5)	C14—C15	1.347 (5)
C4—H4	0.9300	C14—H14	0.9300
C5—C10	1.397 (5)	C15—C16	1.363 (4)
C5—C6	1.437 (4)	C15—H15	0.9300
C6—C7	1.410 (4)	C16—H16	0.9300
C7—C8	1.376 (4)
O2—S1—O1	119.67 (11)	C6—C7—H7	120.0
O2—S1—N1	106.20 (10)	C7—C8—C9	119.8 (4)
O1—S1—N1	106.52 (10)	C7—C8—H8	120.1
O2—S1—C11	108.04 (11)	C9—C8—H8	120.1
O1—S1—C11	107.11 (11)	C10—C9—C8	121.0 (3)
N1—S1—C11	108.98 (10)	C10—C9—H9	119.5
C1—N1—S1	118.87 (14)	C8—C9—H9	119.5
C1—N1—H1	107.4	C9—C10—C5	121.8 (4)
S1—N1—H1	107.3	C9—C10—H10	119.1
C2—C1—C6	121.7 (2)	C5—C10—H10	119.1
C2—C1—N1	120.6 (2)	C12—C11—C16	121.4 (2)
C6—C1—N1	117.7 (2)	C12—C11—S1	119.00 (18)
C1—C2—C3	120.8 (3)	C16—C11—S1	119.57 (19)
C1—C2—H2	119.6	C11—C12—C13	118.4 (3)
C3—C2—H2	119.6	C11—C12—H12	120.8
C4—C3—C2	119.7 (3)	C13—C12—H12	120.8
C4—C3—H3	120.1	C14—C13—C12	119.5 (3)
C2—C3—H3	120.1	C14—C13—H13	120.3
C3—C4—C5	122.2 (3)	C12—C13—H13	120.3
C3—C4—H4	118.9	C15—C14—C13	120.9 (3)
C5—C4—H4	118.9	C15—C14—H14	119.6
C10—C5—C4	123.4 (4)	C13—C14—H14	119.6
C10—C5—C6	117.7 (4)	C14—C15—C16	120.7 (3)
C4—C5—C6	118.8 (3)	C14—C15—H15	119.6
C7—C6—C1	123.5 (2)	C16—C15—H15	119.6
C7—C6—C5	119.7 (3)	C15—C16—C11	119.1 (3)
C1—C6—C5	116.8 (3)	C15—C16—H16	120.4
C8—C7—C6	119.9 (3)	C11—C16—H16	120.4
C8—C7—H7	120.0
O2—S1—N1—C1	173.69 (18)	C5—C6—C7—C8	−2.5 (4)
O1—S1—N1—C1	45.1 (2)	C6—C7—C8—C9	−0.2 (5)
C11—S1—N1—C1	−70.1 (2)	C7—C8—C9—C10	1.6 (6)
S1—N1—C1—C2	91.7 (2)	C8—C9—C10—C5	−0.3 (6)
S1—N1—C1—C6	−89.3 (2)	C4—C5—C10—C9	178.8 (3)
C6—C1—C2—C3	0.4 (4)	C6—C5—C10—C9	−2.4 (5)
N1—C1—C2—C3	179.3 (3)	O2—S1—C11—C12	19.9 (2)
C1—C2—C3—C4	2.0 (5)	O1—S1—C11—C12	150.09 (19)
C2—C3—C4—C5	−2.8 (5)	N1—S1—C11—C12	−95.1 (2)
C3—C4—C5—C10	−179.9 (3)	O2—S1—C11—C16	−160.45 (19)
C3—C4—C5—C6	1.2 (4)	O1—S1—C11—C16	−30.3 (2)
C2—C1—C6—C7	176.5 (2)	N1—S1—C11—C16	84.6 (2)
N1—C1—C6—C7	−2.4 (3)	C16—C11—C12—C13	−0.6 (4)
C2—C1—C6—C5	−1.9 (3)	S1—C11—C12—C13	179.0 (2)
N1—C1—C6—C5	179.2 (2)	C11—C12—C13—C14	0.4 (4)
C10—C5—C6—C7	3.7 (4)	C12—C13—C14—C15	−0.1 (5)
C4—C5—C6—C7	−177.4 (3)	C13—C14—C15—C16	−0.1 (5)
C10—C5—C6—C1	−177.9 (2)	C14—C15—C16—C11	−0.1 (5)
C4—C5—C6—C1	1.1 (4)	C12—C11—C16—C15	0.5 (4)
C1—C6—C7—C8	179.2 (3)	S1—C11—C16—C15	−179.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.90	2.05	2.911 (3)	159.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.90	2.05	2.911 (3)	159

Symmetry code: (i) .