3-Amino-phenyl naphthalene-1-sulfonate.

In the title compound, C(16)H(13)NO(3)S, the plane of the naphthalene ring system forms a dihedral angle of 64.66 (10)° with the benzene ring. The mol-ecular structure is stabilized by weak intra-molecular C-H⋯O inter-actions and the crystal packing is stabilized by weak inter-molecular N-H⋯O and C-H⋯O inter-actions and by π-π stacking inter-actions of the inversion-related naphthalene units [centroid-centroid distance of 3.7373 (14) Å].

Related literature

For the structures of closely related compounds, see: Manivannan et al. (2005a ▶,b ▶); Ramachandran et al.(2007 ▶); Vennila et al. (2008 ▶). For applications, see: Spungin et al. (1984 ▶); Yachi et al. (1989 ▶).

Experimental

Crystal data

C16H13NO3S

M = 299.33

Monoclinic,

a = 8.4558 (2) Å

b = 8.6712 (3) Å

c = 19.5915 (6) Å

β = 100.321 (2)°

V = 1413.24 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 295 (2) K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.932, T max = 0.954

19808 measured reflections

4981 independent reflections

3126 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.174

S = 1.05

4981 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808041032/gk2179sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041032/gk2179Isup2.hkl

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

C16H13NO3S	F(000) = 624
Mr = 299.33	Dx = 1.407 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4818 reflections
a = 8.4558 (2) Å	θ = 2.2–25.4°
b = 8.6712 (3) Å	µ = 0.24 mm−1
c = 19.5915 (6) Å	T = 295 K
β = 100.321 (2)°	Block, brown
V = 1413.24 (7) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEX2 diffractometer	4981 independent reflections
Radiation source: fine-focus sealed tube	3126 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω and φ scans	θmax = 32.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→10
Tmin = 0.932, Tmax = 0.954	k = −12→11
19808 measured reflections	l = −21→29

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0763P)2 + 0.3485P] where P = (Fo2 + 2Fc2)/3
4981 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.44 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
C1	0.34222 (19)	0.8581 (2)	0.10826 (8)	0.0475 (4)
C2	0.2573 (3)	0.9698 (3)	0.13547 (12)	0.0688 (6)
H2	0.2543	0.9701	0.1827	0.083*
C3	0.1749 (3)	1.0837 (3)	0.09239 (19)	0.0876 (8)
H3	0.1173	1.1596	0.1109	0.105*
C4	0.1793 (3)	1.0828 (3)	0.02504 (18)	0.0858 (8)
H4	0.1241	1.1593	−0.0029	0.103*
C5	0.2639 (2)	0.9713 (2)	−0.00569 (11)	0.0634 (5)
C6	0.2687 (4)	0.9715 (4)	−0.07762 (13)	0.0910 (9)
H6	0.2122	1.0468	−0.1058	0.109*
C7	0.3515 (4)	0.8673 (4)	−0.10559 (13)	0.1015 (12)
H7	0.3537	0.8711	−0.1529	0.122*
C8	0.4342 (4)	0.7536 (3)	−0.06564 (14)	0.0872 (9)
H8	0.4913	0.6808	−0.0863	0.105*
C9	0.4342 (2)	0.7451 (2)	0.00414 (11)	0.0619 (5)
H9	0.4904	0.6666	0.0303	0.074*
C10	0.34948 (19)	0.85482 (19)	0.03643 (8)	0.0458 (4)
C11	0.21070 (19)	0.52112 (19)	0.14424 (9)	0.0466 (4)
C12	0.0822 (2)	0.5617 (2)	0.09445 (10)	0.0595 (5)
H12	0.0949	0.6176	0.0553	0.071*
C13	−0.0674 (2)	0.5150 (3)	0.10555 (12)	0.0696 (6)
H13	−0.1582	0.5414	0.0734	0.084*
C14	−0.0850 (2)	0.4309 (2)	0.16279 (11)	0.0637 (5)
H14	−0.1874	0.4025	0.1692	0.076*
C15	0.0471 (2)	0.3876 (2)	0.21112 (10)	0.0561 (4)
C16	0.1979 (2)	0.4357 (2)	0.20153 (9)	0.0511 (4)
H16	0.2890	0.4101	0.2336	0.061*
O1	0.36734 (15)	0.56180 (15)	0.13433 (7)	0.0580 (3)
O2	0.3993 (2)	0.7447 (2)	0.23185 (7)	0.0915 (6)
O3	0.60456 (18)	0.7106 (2)	0.15880 (10)	0.0903 (6)
N1	0.0316 (3)	0.3014 (3)	0.26868 (11)	0.0868 (6)
H1A	−0.0621	0.2733	0.2752	0.104*
H1B	0.1156	0.2758	0.2981	0.104*
S1	0.44040 (6)	0.72128 (7)	0.16539 (2)	0.06166 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0464 (8)	0.0490 (9)	0.0497 (8)	−0.0131 (7)	0.0153 (6)	−0.0086 (7)
C2	0.0679 (12)	0.0677 (13)	0.0789 (13)	−0.0188 (10)	0.0346 (10)	−0.0268 (11)
C3	0.0697 (14)	0.0536 (13)	0.144 (3)	0.0011 (10)	0.0312 (15)	−0.0233 (15)
C4	0.0699 (14)	0.0511 (12)	0.130 (2)	−0.0040 (10)	0.0007 (14)	0.0086 (14)
C5	0.0621 (11)	0.0556 (11)	0.0683 (12)	−0.0236 (9)	0.0003 (9)	0.0073 (9)
C6	0.1060 (19)	0.0930 (19)	0.0634 (13)	−0.0531 (16)	−0.0135 (13)	0.0241 (13)
C7	0.136 (3)	0.118 (2)	0.0525 (13)	−0.082 (2)	0.0230 (15)	−0.0135 (15)
C8	0.1037 (19)	0.0958 (19)	0.0737 (14)	−0.0525 (16)	0.0469 (14)	−0.0426 (14)
C9	0.0619 (11)	0.0660 (12)	0.0638 (11)	−0.0206 (9)	0.0276 (9)	−0.0226 (9)
C10	0.0451 (8)	0.0451 (8)	0.0482 (8)	−0.0160 (6)	0.0112 (6)	−0.0062 (6)
C11	0.0461 (8)	0.0416 (8)	0.0523 (9)	−0.0039 (6)	0.0095 (6)	−0.0014 (7)
C12	0.0603 (10)	0.0606 (11)	0.0536 (10)	−0.0068 (9)	−0.0006 (8)	0.0050 (8)
C13	0.0519 (10)	0.0769 (14)	0.0725 (13)	−0.0074 (9)	−0.0091 (9)	−0.0047 (11)
C14	0.0522 (10)	0.0598 (11)	0.0798 (13)	−0.0175 (8)	0.0139 (9)	−0.0150 (10)
C15	0.0643 (10)	0.0438 (9)	0.0640 (11)	−0.0099 (8)	0.0214 (9)	−0.0058 (8)
C16	0.0524 (9)	0.0452 (9)	0.0546 (9)	−0.0002 (7)	0.0068 (7)	0.0035 (7)
O1	0.0501 (6)	0.0556 (7)	0.0704 (8)	−0.0023 (5)	0.0165 (6)	0.0074 (6)
O2	0.1164 (14)	0.1138 (14)	0.0419 (7)	−0.0494 (11)	0.0078 (8)	−0.0014 (8)
O3	0.0456 (8)	0.1086 (14)	0.1099 (14)	−0.0144 (8)	−0.0046 (8)	0.0307 (11)
N1	0.0905 (14)	0.0891 (15)	0.0865 (14)	−0.0159 (11)	0.0316 (11)	0.0238 (11)
S1	0.0536 (3)	0.0762 (4)	0.0524 (3)	−0.0199 (2)	0.00177 (19)	0.0072 (2)

C1—C2	1.370 (3)	C9—H9	0.9300
C1—C10	1.420 (2)	C11—C16	1.365 (2)
C1—S1	1.7368 (19)	C11—C12	1.370 (2)
C2—C3	1.401 (4)	C11—O1	1.4173 (19)
C2—H2	0.9300	C12—C13	1.382 (3)
C3—C4	1.327 (4)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.368 (3)
C4—C5	1.401 (4)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.381 (3)
C5—C6	1.417 (3)	C14—H14	0.9300
C5—C10	1.418 (3)	C15—N1	1.378 (3)
C6—C7	1.321 (5)	C15—C16	1.386 (2)
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.370 (5)	O1—S1	1.5905 (14)
C7—H7	0.9300	O2—S1	1.4212 (16)
C8—C9	1.369 (3)	O3—S1	1.4199 (16)
C8—H8	0.9300	N1—H1A	0.8600
C9—C10	1.408 (3)	N1—H1B	0.8600
C2—C1—C10	121.24 (18)	C5—C10—C1	117.02 (17)
C2—C1—S1	117.12 (15)	C16—C11—C12	123.72 (16)
C10—C1—S1	121.63 (13)	C16—C11—O1	117.47 (15)
C1—C2—C3	120.2 (2)	C12—C11—O1	118.71 (16)
C1—C2—H2	119.9	C11—C12—C13	116.40 (18)
C3—C2—H2	119.9	C11—C12—H12	121.8
C4—C3—C2	119.7 (2)	C13—C12—H12	121.8
C4—C3—H3	120.2	C14—C13—C12	121.48 (18)
C2—C3—H3	120.2	C14—C13—H13	119.3
C3—C4—C5	122.6 (2)	C12—C13—H13	119.3
C3—C4—H4	118.7	C13—C14—C15	120.92 (18)
C5—C4—H4	118.7	C13—C14—H14	119.5
C4—C5—C6	122.3 (3)	C15—C14—H14	119.5
C4—C5—C10	119.2 (2)	N1—C15—C14	121.64 (19)
C6—C5—C10	118.5 (2)	N1—C15—C16	119.91 (19)
C7—C6—C5	121.6 (3)	C14—C15—C16	118.43 (17)
C7—C6—H6	119.2	C11—C16—C15	119.01 (16)
C5—C6—H6	119.2	C11—C16—H16	120.5
C6—C7—C8	120.6 (2)	C15—C16—H16	120.5
C6—C7—H7	119.7	C11—O1—S1	118.20 (11)
C8—C7—H7	119.7	C15—N1—H1A	120.0
C9—C8—C7	121.2 (3)	C15—N1—H1B	120.0
C9—C8—H8	119.4	H1A—N1—H1B	120.0
C7—C8—H8	119.4	O3—S1—O2	119.75 (11)
C8—C9—C10	120.2 (2)	O3—S1—O1	103.16 (10)
C8—C9—H9	119.9	O2—S1—O1	109.45 (9)
C10—C9—H9	119.9	O3—S1—C1	110.36 (9)
C9—C10—C5	117.90 (18)	O2—S1—C1	108.99 (11)
C9—C10—C1	125.09 (18)	O1—S1—C1	103.85 (7)
C10—C1—C2—C3	0.2 (3)	C16—C11—C12—C13	1.8 (3)
S1—C1—C2—C3	−179.87 (16)	O1—C11—C12—C13	178.00 (17)
C1—C2—C3—C4	0.1 (3)	C11—C12—C13—C14	−0.9 (3)
C2—C3—C4—C5	0.1 (4)	C12—C13—C14—C15	−1.0 (3)
C3—C4—C5—C6	−179.7 (2)	C13—C14—C15—N1	−179.3 (2)
C3—C4—C5—C10	−0.5 (3)	C13—C14—C15—C16	2.1 (3)
C4—C5—C6—C7	178.7 (2)	C12—C11—C16—C15	−0.7 (3)
C10—C5—C6—C7	−0.6 (3)	O1—C11—C16—C15	−176.96 (15)
C5—C6—C7—C8	0.9 (4)	N1—C15—C16—C11	−179.90 (18)
C6—C7—C8—C9	−0.4 (4)	C14—C15—C16—C11	−1.3 (3)
C7—C8—C9—C10	−0.5 (3)	C16—C11—O1—S1	−91.61 (17)
C8—C9—C10—C5	0.8 (3)	C12—C11—O1—S1	91.97 (18)
C8—C9—C10—C1	−179.44 (16)	C11—O1—S1—O3	168.69 (12)
C4—C5—C10—C9	−179.52 (17)	C11—O1—S1—O2	40.15 (16)
C6—C5—C10—C9	−0.3 (2)	C11—O1—S1—C1	−76.12 (13)
C4—C5—C10—C1	0.7 (2)	C2—C1—S1—O3	−127.86 (16)
C6—C5—C10—C1	179.93 (16)	C10—C1—S1—O3	52.09 (16)
C2—C1—C10—C9	179.68 (17)	C2—C1—S1—O2	5.58 (17)
S1—C1—C10—C9	−0.3 (2)	C10—C1—S1—O2	−174.48 (13)
C2—C1—C10—C5	−0.6 (2)	C2—C1—S1—O1	122.16 (14)
S1—C1—C10—C5	179.50 (12)	C10—C1—S1—O1	−57.89 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.41	2.829 (3)	107
C9—H9···O3	0.93	2.56	3.127 (3)	120
N1—H1B···O3i	0.86	2.43	3.246 (3)	158
C7—H7···O2ii	0.93	2.56	3.422 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2	0.93	2.41	2.829 (3)	107
C9—H9⋯O3	0.93	2.56	3.127 (3)	120
N1—H1B⋯O3i	0.86	2.43	3.246 (3)	158
C7—H7⋯O2ii	0.93	2.56	3.422 (3)	154

Symmetry codes: (i) ; (ii) .