4-Amino-phenyl naphthalene-1-sulfonate.

In the title compound, C(16)H(13)NO(3)S, the plane of the amino-benzene ring makes a dihedral angle of 61.04 (6)° with the naphthalene ring system. Both ring systems form weak intra-molecular C-H⋯O hydrogen bonds with the sulfonate group. In the crystal structure, weak inter-molecular N-H⋯O hydrogen bonds and a C-H⋯π inter-action are observed.

Related literature

For biological activity, see: Yachi et al. (1989 ▶). For the structures of closely related compounds, see: Manivannan et al. (2005a ▶,b ▶).

Experimental

Crystal data

C16H13NO3S

M = 299.33

Orthorhombic,

a = 7.0456 (3) Å

b = 12.4789 (6) Å

c = 15.8064 (8) Å

V = 1389.72 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 295 (2) K

0.36 × 0.16 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.918, T max = 0.962

19808 measured reflections

4629 independent reflections

3267 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.164

S = 1.03

4629 reflections

190 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.37 e Å−3

Absolute structure: Flack (1983 ▶), 1972 Friedel pairs

Flack parameter: −0.01 (10)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: APEX2; 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/S1600536808014438/is2293sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014438/is2293Isup2.hkl

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

C16H13NO3S	F000 = 624
Mr = 299.33	Dx = 1.431 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4586 reflections
a = 7.0456 (3) Å	θ = 2.8–25.7º
b = 12.4789 (6) Å	µ = 0.24 mm−1
c = 15.8064 (8) Å	T = 295 (2) K
V = 1389.72 (11) Å3	Block, brown
Z = 4	0.36 × 0.16 × 0.16 mm

Bruker Kappa APEXII diffractometer	4629 independent reflections
Radiation source: fine-focus sealed tube	3267 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
T = 295(2) K	θmax = 31.9º
ω and φ scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.918, Tmax = 0.962	k = −18→18
19808 measured reflections	l = −23→19

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051	w = 1/[σ2(Fo2) + (0.0956P)2 + 0.1498P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.164	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.44 e Å−3
4629 reflections	Δρmin = −0.37 e Å−3
190 parameters	Extinction correction: none
2 restraints	Absolute structure: Flack (1983), 1972 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (10)
Secondary atom site location: difference Fourier map

	x	y	z	Uiso*/Ueq
C1	0.2028 (3)	−0.04132 (18)	0.71108 (14)	0.0415 (4)
C2	0.0284 (3)	−0.0930 (2)	0.71475 (17)	0.0508 (6)
H2	−0.0763	−0.0641	0.6871	0.061*
C3	0.0110 (3)	−0.1874 (2)	0.7597 (2)	0.0545 (6)
H3	−0.1064	−0.2211	0.7637	0.065*
C4	0.1674 (3)	−0.23186 (18)	0.79873 (15)	0.0443 (5)
C5	0.3412 (3)	−0.18155 (19)	0.79520 (16)	0.0488 (5)
H5	0.4463	−0.2117	0.8217	0.059*
C6	0.3577 (3)	−0.08513 (19)	0.75158 (17)	0.0503 (5)
H6	0.4740	−0.0500	0.7497	0.060*
C7	0.2918 (4)	−0.0253 (2)	0.51224 (15)	0.0462 (5)
C8	0.4146 (4)	−0.1082 (2)	0.5015 (2)	0.0569 (6)
H8	0.5286	−0.1097	0.5311	0.068*
C9	0.3689 (6)	−0.1918 (2)	0.4455 (2)	0.0699 (8)
H9	0.4551	−0.2472	0.4370	0.084*
C10	0.2039 (6)	−0.1927 (2)	0.40449 (19)	0.0634 (7)
H10	0.1759	−0.2496	0.3685	0.076*
C11	0.0689 (4)	−0.1083 (2)	0.41450 (18)	0.0539 (6)
C12	−0.1042 (5)	−0.1111 (3)	0.3724 (2)	0.0664 (8)
H12	−0.1329	−0.1691	0.3377	0.080*
C13	−0.2326 (5)	−0.0302 (3)	0.38116 (19)	0.0685 (8)
H13	−0.3481	−0.0328	0.3527	0.082*
C14	−0.1884 (4)	0.0572 (3)	0.43368 (18)	0.0621 (7)
H14	−0.2748	0.1131	0.4393	0.074*
C15	−0.0212 (4)	0.0612 (2)	0.47630 (17)	0.0515 (6)
H15	0.0046	0.1198	0.5108	0.062*
C16	0.1133 (3)	−0.02101 (18)	0.46937 (15)	0.0451 (5)
N1	0.1446 (3)	−0.32773 (15)	0.83938 (13)	0.0487 (5)
H1A	0.2400	−0.3580	0.8635	0.058*
H1B	0.0348	−0.3578	0.8408	0.058*
O1	0.2166 (3)	0.05975 (15)	0.66776 (12)	0.0592 (5)
O2	0.3197 (4)	0.17748 (15)	0.55522 (14)	0.0706 (6)
O3	0.5453 (3)	0.04850 (19)	0.61441 (14)	0.0659 (6)
S1	0.35628 (9)	0.07323 (5)	0.58673 (4)	0.04995 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0433 (10)	0.0422 (9)	0.0391 (11)	−0.0016 (8)	−0.0002 (9)	−0.0121 (8)
C2	0.0377 (10)	0.0564 (14)	0.0584 (15)	−0.0005 (9)	−0.0021 (10)	0.0099 (12)
C3	0.0381 (10)	0.0611 (15)	0.0644 (16)	−0.0067 (10)	−0.0023 (10)	0.0090 (14)
C4	0.0447 (11)	0.0441 (11)	0.0440 (12)	−0.0009 (9)	0.0012 (9)	0.0003 (9)
C5	0.0444 (11)	0.0485 (12)	0.0535 (14)	−0.0027 (10)	−0.0119 (10)	−0.0009 (11)
C6	0.0442 (10)	0.0461 (12)	0.0607 (15)	−0.0082 (10)	−0.0094 (11)	−0.0036 (11)
C7	0.0534 (12)	0.0399 (11)	0.0452 (12)	−0.0093 (9)	0.0063 (10)	−0.0008 (10)
C8	0.0586 (14)	0.0531 (14)	0.0591 (17)	0.0050 (11)	0.0030 (13)	0.0016 (12)
C9	0.093 (2)	0.0475 (14)	0.0694 (19)	0.0115 (15)	0.0126 (18)	−0.0080 (14)
C10	0.088 (2)	0.0484 (14)	0.0536 (15)	−0.0082 (13)	0.0071 (15)	−0.0097 (13)
C11	0.0719 (15)	0.0475 (13)	0.0423 (13)	−0.0153 (11)	0.0063 (12)	−0.0005 (11)
C12	0.083 (2)	0.0687 (18)	0.0474 (15)	−0.0234 (16)	−0.0050 (14)	−0.0016 (14)
C13	0.0637 (17)	0.092 (2)	0.0500 (15)	−0.0171 (16)	−0.0091 (13)	0.0141 (17)
C14	0.0585 (14)	0.0730 (19)	0.0547 (15)	0.0032 (13)	0.0028 (12)	0.0103 (14)
C15	0.0569 (13)	0.0520 (14)	0.0456 (13)	−0.0040 (10)	0.0064 (10)	0.0026 (11)
C16	0.0550 (12)	0.0409 (11)	0.0395 (11)	−0.0095 (9)	0.0054 (10)	0.0018 (9)
N1	0.0379 (8)	0.0452 (10)	0.0631 (13)	−0.0036 (8)	−0.0047 (9)	0.0182 (9)
O1	0.0663 (10)	0.0520 (9)	0.0594 (10)	−0.0055 (8)	0.0036 (8)	−0.0032 (8)
O2	0.0897 (16)	0.0419 (10)	0.0803 (14)	−0.0233 (10)	0.0025 (12)	0.0052 (10)
O3	0.0465 (9)	0.0750 (14)	0.0763 (13)	−0.0157 (9)	0.0011 (9)	−0.0054 (11)
S1	0.0510 (3)	0.0416 (3)	0.0573 (4)	−0.0135 (2)	0.0011 (3)	−0.0021 (3)

C1—C6	1.378 (3)	C9—H9	0.9300
C1—C2	1.389 (3)	C10—C11	1.428 (5)
C1—O1	1.438 (3)	C10—H10	0.9300
C2—C3	1.381 (4)	C11—C12	1.390 (4)
C2—H2	0.9300	C11—C16	1.427 (3)
C3—C4	1.380 (3)	C12—C13	1.362 (5)
C3—H3	0.9300	C12—H12	0.9300
C4—N1	1.368 (3)	C13—C14	1.406 (5)
C4—C5	1.377 (3)	C13—H13	0.9300
C5—C6	1.392 (3)	C14—C15	1.358 (4)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—C16	1.401 (4)
C7—C8	1.360 (4)	C15—H15	0.9300
C7—C16	1.430 (3)	N1—H1A	0.8600
C7—S1	1.762 (3)	N1—H1B	0.8600
C8—C9	1.404 (4)	O2—S1	1.417 (2)
C8—H8	0.9300	O3—S1	1.436 (2)
C9—C10	1.332 (5)	O1—S1	1.624 (2)
C6—C1—C2	119.8 (2)	C11—C10—H10	119.3
C6—C1—O1	121.0 (2)	C12—C11—C16	120.2 (3)
C2—C1—O1	119.1 (2)	C12—C11—C10	120.8 (3)
C3—C2—C1	119.7 (2)	C16—C11—C10	119.0 (3)
C3—C2—H2	120.1	C13—C12—C11	121.0 (3)
C1—C2—H2	120.1	C13—C12—H12	119.5
C4—C3—C2	120.1 (2)	C11—C12—H12	119.5
C4—C3—H3	119.9	C12—C13—C14	119.2 (3)
C2—C3—H3	119.9	C12—C13—H13	120.4
N1—C4—C5	121.5 (2)	C14—C13—H13	120.4
N1—C4—C3	117.9 (2)	C15—C14—C13	120.9 (3)
C5—C4—C3	120.6 (2)	C15—C14—H14	119.5
C4—C5—C6	119.2 (2)	C13—C14—H14	119.5
C4—C5—H5	120.4	C14—C15—C16	121.4 (3)
C6—C5—H5	120.4	C14—C15—H15	119.3
C1—C6—C5	120.5 (2)	C16—C15—H15	119.3
C1—C6—H6	119.8	C15—C16—C11	117.3 (2)
C5—C6—H6	119.8	C15—C16—C7	125.8 (2)
C8—C7—C16	121.9 (2)	C11—C16—C7	116.9 (2)
C8—C7—S1	116.8 (2)	C4—N1—H1A	120.0
C16—C7—S1	121.19 (19)	C4—N1—H1B	120.0
C7—C8—C9	119.9 (3)	H1A—N1—H1B	120.0
C7—C8—H8	120.1	C1—O1—S1	120.50 (15)
C9—C8—H8	120.1	O2—S1—O3	118.25 (13)
C10—C9—C8	120.9 (3)	O2—S1—O1	105.20 (13)
C10—C9—H9	119.6	O3—S1—O1	107.43 (12)
C8—C9—H9	119.6	O2—S1—C7	111.02 (13)
C9—C10—C11	121.4 (3)	O3—S1—C7	107.04 (13)
C9—C10—H10	119.3	O1—S1—C7	107.38 (11)
C6—C1—C2—C3	0.7 (4)	C14—C15—C16—C11	1.1 (4)
O1—C1—C2—C3	−176.8 (2)	C14—C15—C16—C7	−179.1 (2)
C1—C2—C3—C4	−1.9 (4)	C12—C11—C16—C15	−1.9 (4)
C2—C3—C4—N1	−177.2 (2)	C10—C11—C16—C15	178.9 (2)
C2—C3—C4—C5	1.6 (4)	C12—C11—C16—C7	178.3 (2)
N1—C4—C5—C6	178.7 (2)	C10—C11—C16—C7	−1.0 (3)
C3—C4—C5—C6	−0.1 (4)	C8—C7—C16—C15	−179.7 (3)
C2—C1—C6—C5	0.9 (4)	S1—C7—C16—C15	4.3 (3)
O1—C1—C6—C5	178.3 (2)	C8—C7—C16—C11	0.1 (3)
C4—C5—C6—C1	−1.1 (4)	S1—C7—C16—C11	−175.90 (18)
C16—C7—C8—C9	1.4 (4)	C6—C1—O1—S1	63.1 (3)
S1—C7—C8—C9	177.6 (2)	C2—C1—O1—S1	−119.4 (2)
C7—C8—C9—C10	−2.0 (5)	C1—O1—S1—O2	174.10 (17)
C8—C9—C10—C11	1.2 (5)	C1—O1—S1—O3	−59.1 (2)
C9—C10—C11—C12	−178.9 (3)	C1—O1—S1—C7	55.8 (2)
C9—C10—C11—C16	0.4 (4)	C8—C7—S1—O2	137.0 (2)
C16—C11—C12—C13	1.4 (4)	C16—C7—S1—O2	−46.8 (2)
C10—C11—C12—C13	−179.4 (3)	C8—C7—S1—O3	6.6 (2)
C11—C12—C13—C14	0.0 (4)	C16—C7—S1—O3	−177.21 (18)
C12—C13—C14—C15	−0.8 (4)	C8—C7—S1—O1	−108.5 (2)
C13—C14—C15—C16	0.3 (4)	C16—C7—S1—O1	67.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3	0.93	2.52	3.038 (3)	116
C8—H8···O3	0.93	2.38	2.804 (4)	108
C15—H15···O2	0.93	2.44	3.071 (4)	125
N1—H1B···O1i	0.86	2.05	2.909 (3)	173
N1—H1A···O3ii	0.86	1.94	2.773 (3)	162
C6—H6···Cgiii	0.93	2.84	3.380 (3)	107

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3	0.93	2.52	3.038 (3)	116
C8—H8⋯O3	0.93	2.38	2.804 (4)	108
C15—H15⋯O2	0.93	2.44	3.071 (4)	125
N1—H1B⋯O1i	0.86	2.05	2.909 (3)	173
N1—H1A⋯O3ii	0.86	1.94	2.773 (3)	162
C6—H6⋯Cgiii	0.93	2.84	3.380 (3)	107

Symmetry codes: (i) ; (ii) ; (iii) . Cg is the centroid of the C11–C16 ring.