4-Amino­phenyl naphthalene-1-sulfonate

Vennila, J.P.; Thilagavathi, R.; Kavipriya, R.; Kavitha, H.P.; Manivannan, V.

doi:10.1107/S1600536808014438

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1124

doi:10.1107/S1600536808014438

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4-Aminophenyl naphthalene-1-sulfonate

Jasmine P. Vennila,^a R. Thilagavathi,^b R. Kavipriya,^b Helen P. Kavitha ^b and V. Manivannan ^c ^*

^aDepartment of Physics, Panimalar Institute of Technology, Chennai 600 095, India, ^bDepartment of Chemistry, SRM University, Ramapuram, Chennai 600 089, India, and ^cDepartment of Physics, Presidency College, Chennai 600 005, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 12 May 2008; accepted 13 May 2008; online 21 May 2008)

In the title compound, C₁₆H₁₃NO₃S, the plane of the aminobenzene ring makes a dihedral angle of 61.04 (6)° with the naphthalene ring system. Both ring systems form weak intramolecular C—H⋯O hydrogen bonds with the sulfonate group. In the crystal structure, weak intermolecular N—H⋯O hydrogen bonds and a C—H⋯π interaction 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_r = 299.33
Orthorhombic, P 2₁ 2₁ 2₁
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 (SADABS; 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[F² > 2σ(F²)] = 0.051
wR(F²) = 0.164
S = 1.03
4629 reflections
190 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.37 e Å⁻³
Absolute structure: Flack (1983 ), 1972 Friedel pairs
Flack parameter: −0.01 (10)

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) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y, z+{\script{1\over 2}}]$ . Cg is the centroid of the C11–C16 ring.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014438/is2293sup1.cif

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

checkCIF report

Comment top

Several compounds containing para-toluene sulfonate moiety are used in the fields of biology and industry. The merging of lipids can be monitored using a derivative of para-toluene sulfonate (Yachi et al., 1989).

We report the crystal structure of the title compound, (I). The geometric parameters of the molecule of (I) (Fig. 1) agree well with the reported structures (Manivannan et al. 2005a,b). The plane of the aminobenzene ring forms a dihedral angle of 61.04 (6)° with the naphthalene ring.

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak intermolecular N—H···O interactions and a C—H···π interaction (Table 1), involving the ring C11—C16 (centroid Cg).

Related literature top

For biological activity, see: Yachi et al. (1989). For the structures of closely related compounds, see: Manivannan et al. (2005a,b). Cg is the centroid of the C11–C16 ring.

Experimental top

1-Napthalene sulfonyl chloride (5 mmol) dissolved in acetone (4 ml) was added dropwise to p-amino phenol (5 mmol) in aqueous NaOH (4 ml, 5%) with constant shaking. The precipitated compound (3.5 mmol, yield 70%) was recrystlized from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. Intramolecular H-bonds are shown as dotted lines.
	Fig. 2. The packing of (I), viewed down the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

4-Aminophenyl naphthalene-1-sulfonate top

Crystal data top

C₁₆H₁₃NO₃S	F(000) = 624
M_r = 299.33	D_x = 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 = 2.8–25.7°
b = 12.4789 (6) Å	µ = 0.24 mm⁻¹
c = 15.8064 (8) Å	T = 295 K
V = 1389.72 (11) Å³	Block, brown
Z = 4	0.36 × 0.16 × 0.16 mm

Data collection top

Bruker Kappa APEXII diffractometer	4629 independent reflections
Radiation source: fine-focus sealed tube	3267 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω and ϕ scans	θ_max = 31.9°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.918, T_max = 0.962	k = −18→18
19808 measured reflections	l = −23→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.164	w = 1/[σ²(F_o²) + (0.0956P)² + 0.1498P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4629 reflections	Δρ_max = 0.44 e Å⁻³
190 parameters	Δρ_min = −0.37 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1972 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (10)

Crystal data top

C₁₆H₁₃NO₃S	V = 1389.72 (11) Å³
M_r = 299.33	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.0456 (3) Å	µ = 0.24 mm⁻¹
b = 12.4789 (6) Å	T = 295 K
c = 15.8064 (8) Å	0.36 × 0.16 × 0.16 mm

Data collection top

Bruker Kappa APEXII diffractometer	4629 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3267 reflections with I > 2σ(I)
T_min = 0.918, T_max = 0.962	R_int = 0.030
19808 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.164	Δρ_max = 0.44 e Å⁻³
S = 1.03	Δρ_min = −0.37 e Å⁻³
4629 reflections	Absolute structure: Flack (1983), 1972 Friedel pairs
190 parameters	Absolute structure parameter: −0.01 (10)
2 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1/2, −y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃NO₃S
M_r	299.33
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	7.0456 (3), 12.4789 (6), 15.8064 (8)
V (Å³)	1389.72 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.36 × 0.16 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.918, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	19808, 4629, 3267
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.742

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.164, 1.03
No. of reflections	4629
No. of parameters	190
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.37
Absolute structure	Flack (1983), 1972 Friedel pairs
Absolute structure parameter	−0.01 (10)

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1/2, −y, z+1/2.

Acknowledgements

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Madras, for the data collection.

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