3-Amino­phenyl naphthalene-1-sulfonate

Vennila, J.P.; Kavitha, H.P.; Thiruvadigal, D.J.; Venkatraman, B.R.; Manivannan, V.

doi:10.1107/S1600536808041032

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o72

doi:10.1107/S1600536808041032

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3-Aminophenyl naphthalene-1-sulfonate

Jasmine P. Vennila,^a Helen P. Kavitha,^b D. John Thiruvadigal,^c B. R. Venkatraman ^d and V. Manivannan ^e ^*

^aDepartment of Physics, Panimalar Institute of Technology, Chennai 600 095, India, ^bDepartment of Chemistry, SRM University, Ramapuram, Chennai 600 089, India, ^cDepartment of Physics, SRM University, Kattankulathur Campus, Chennai, India, ^dDepartment of Chemistry, Periyar E.V.R. College, Tiruchirappalli 620 023, India, and ^eDepartment of Physics, Presidency College, Chennai 600 005, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 24 November 2008; accepted 4 December 2008; online 10 December 2008)

In the title compound, C₁₆H₁₃NO₃S, the plane of the naphthalene ring system forms a dihedral angle of 64.66 (10)° with the benzene 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 and C—H⋯O interactions and by π–π stacking interactions 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_r = 299.33
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.055
wR(F²) = 0.174
S = 1.05
4981 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.44 e Å⁻³

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Several compounds containing the 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). This method has been used in studying the membrane fusion during the acrosome reaction (Spungin et al., 1984).

The plane of the benzene ring forms a dihedral angle of 64.66 (10) ° with the naphthalene ring system. The torsion angles O2—S1—C1—C2 and O3—S1—C1—C10 [5.58 (17) ° and 52.09 (16) °, respectively] indicate the syn conformation of sulfonyl moiety. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak intermolecular C—H···O interactions, N—H···O interactions and π-π stacking interactions of the naphthalene fragments related by inversion center

Related literature top

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 top

1-Napthalene sulfonyl chloride (5 mmol) dissolved in acetone (4 ml) was added dropwise to 3-amino phenol (5 mmol) in aqueous NaOH (4 ml, 5%) with constant shaking. The precipitated compound (3 mmol, yield 60%) was recrystlized from ethanol to get diffraction quality brown colored crystals.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (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 the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing viewed down the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

3-Aminophenyl naphthalene-1-sulfonate top

Crystal data top

C₁₆H₁₃NO₃S	F(000) = 624
M_r = 299.33	D_x = 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

Data collection top

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

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0763P)² + 0.3485P] where P = (F_o² + 2F_c²)/3
4981 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₆H₁₃NO₃S	V = 1413.24 (7) Å³
M_r = 299.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4558 (2) Å	µ = 0.24 mm⁻¹
b = 8.6712 (3) Å	T = 295 K
c = 19.5915 (6) Å	0.30 × 0.25 × 0.20 mm
β = 100.321 (2)°

Data collection top

Bruker Kappa APEX2 diffractometer	4981 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3126 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.954	R_int = 0.023
19808 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 1.05	Δρ_max = 0.46 e Å⁻³
4981 reflections	Δρ_min = −0.44 e Å⁻³
190 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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃NO₃S
M_r	299.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	8.4558 (2), 8.6712 (3), 19.5915 (6)
β (°)	100.321 (2)
V (Å³)	1413.24 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEX2 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.932, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	19808, 4981, 3126
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.750

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.174, 1.05
No. of reflections	4981
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.44

Computer programs: APEX2 (Bruker, 2004), SAINT (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
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)	153.7

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, −y+3/2, 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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