4-Nitro­phenyl naphthalene-1-sulfonate

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

doi:10.1107/S1600536808027396

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1848

doi:10.1107/S1600536808027396

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4-Nitrophenyl 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 21 August 2008; accepted 25 August 2008; online 30 August 2008)

In the crystal structure of the title compound, C₁₆H₁₁NO₅S, the plane of the naphthalene ring system forms a dihedral angle of 63.39 (8)° with the benzene ring. The nitro group makes a dihedral angle of 10.73 (16)° with the benzene ring. Weak intra- and intermolecular C—H⋯O interactions are observed.

Related literature

For related literature, see: Manivannan et al. (2005 ); Vennila et al. (2008 ); Yachi et al. (1989 ).

Experimental

Crystal data

C₁₆H₁₁NO₅S
M_r = 329.32
Monoclinic, P 2₁ /n
a = 13.4407 (8) Å
b = 6.2990 (3) Å
c = 18.2556 (12) Å
β = 106.296 (2)°
V = 1483.48 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 295 (2) K
0.28 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.935, T_max = 0.962
14281 measured reflections
2801 independent reflections
1935 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.160
S = 1.08
2801 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2	0.93	2.43	2.829 (5)	106
C16—H16⋯O3	0.93	2.46	3.058 (4)	122
C5—H5⋯O2ⁱ	0.93	2.48	3.179 (3)	132
C15—H15⋯O4ⁱⁱ	0.93	2.47	3.340 (5)	155
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[-x+{\script{1\over 2}}, y+{\script{3\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 and SAINT (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/S1600536808027396/is2328sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027396/is2328Isup2.hkl

checkCIF report

Comment top

The merging of lipids can be monitored using a derivative of para-toluene sulfonate (Yachi et al., 1989). The geometric parameters of the title molecule, (I) (Fig. 1), agree well with the reported structures (Manivannan et al. 2005; Vennila et al. 2008)

The plane of the benzene ring forms a dihedral angle of 63.39 (8)° with the naphthalene ring system. The torsion angles O2—S1—C7—C8 and O3—S1—C7—C12 [0.1 (3) ° and 45.8 (2)°, 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 (Fig. 2).

Related literature top

For related literature, see: Manivannan et al. (2005); Vennila et al. (2008); Yachi et al. (1989).

Experimental top

1-Naphthalene sulfonyl chloride (2.5 mmol) dissolved in acetone (4 ml) was added dropwise to 4-nitrophenol (2.5 mmol) in aqueous NaOH (4 ml, 5%) with constant shaking. The precipitated compound (1.8 mmol, yield 72%) was recrystallized from ethanol to get diffraction quality pale yellow crystals.

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.
	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-Nitrophenyl naphthalene-1-sulfonate top

Crystal data top

C₁₆H₁₁NO₅S	F(000) = 680
M_r = 329.32	D_x = 1.474 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4818 reflections
a = 13.4407 (8) Å	θ = 2.2–25.4°
b = 6.2990 (3) Å	µ = 0.24 mm⁻¹
c = 18.2556 (12) Å	T = 295 K
β = 106.296 (2)°	Block, yellow
V = 1483.48 (15) Å³	0.28 × 0.20 × 0.16 mm
Z = 4

Data collection top

Bruker Kappa APEX2 diffractometer	2801 independent reflections
Radiation source: fine-focus sealed tube	1935 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω and ϕ scans	θ_max = 25.7°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.935, T_max = 0.962	k = −7→5
14281 measured reflections	l = −22→22

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0801P)² + 0.4092P] where P = (F_o² + 2F_c²)/3
2801 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₆H₁₁NO₅S	V = 1483.48 (15) Å³
M_r = 329.32	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.4407 (8) Å	µ = 0.24 mm⁻¹
b = 6.2990 (3) Å	T = 295 K
c = 18.2556 (12) Å	0.28 × 0.20 × 0.16 mm
β = 106.296 (2)°

Data collection top

Bruker Kappa APEX2 diffractometer	2801 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1935 reflections with I > 2σ(I)
T_min = 0.935, T_max = 0.962	R_int = 0.041
14281 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.08	Δρ_max = 0.25 e Å⁻³
2801 reflections	Δρ_min = −0.20 e Å⁻³
208 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.54713 (6)	0.94373 (13)	0.12153 (4)	0.0704 (3)
C1	0.37278 (18)	0.7401 (4)	0.09748 (13)	0.0528 (6)
C2	0.3303 (2)	0.7033 (4)	0.15655 (14)	0.0598 (6)
H2	0.3391	0.8008	0.1961	0.072*
C3	0.2749 (2)	0.5218 (4)	0.15633 (15)	0.0613 (7)
H3	0.2454	0.4937	0.1957	0.074*
C4	0.26342 (18)	0.3817 (4)	0.09726 (14)	0.0537 (6)
C5	0.3065 (2)	0.4177 (4)	0.03838 (15)	0.0654 (7)
H5	0.2979	0.3198	−0.0010	0.079*
C6	0.3621 (2)	0.5999 (4)	0.03865 (15)	0.0673 (7)
H6	0.3921	0.6277	−0.0005	0.081*
C7	0.58144 (18)	0.8465 (4)	0.21516 (15)	0.0576 (6)
C8	0.6346 (2)	0.6587 (5)	0.2287 (2)	0.0839 (9)
H8	0.6500	0.5851	0.1891	0.101*
C9	0.6658 (3)	0.5785 (7)	0.3043 (4)	0.1117 (16)
H9	0.7032	0.4525	0.3147	0.134*
C10	0.6415 (3)	0.6838 (9)	0.3611 (3)	0.1157 (15)
H10	0.6627	0.6289	0.4103	0.139*
C11	0.5863 (2)	0.8702 (6)	0.34821 (18)	0.0846 (10)
C12	0.55403 (18)	0.9590 (4)	0.27417 (14)	0.0577 (6)
C13	0.5581 (4)	0.9799 (11)	0.4083 (2)	0.1245 (18)
H13	0.5799	0.9270	0.4579	0.149*
C14	0.5005 (4)	1.1579 (11)	0.3943 (3)	0.137 (2)
H14	0.4815	1.2248	0.4337	0.165*
C15	0.4701 (3)	1.2404 (7)	0.3225 (3)	0.1029 (12)
H15	0.4312	1.3647	0.3139	0.124*
C16	0.4949 (2)	1.1465 (5)	0.26351 (18)	0.0725 (8)
H16	0.4725	1.2067	0.2151	0.087*
O1	0.42304 (14)	0.9358 (3)	0.09765 (10)	0.0644 (5)
O2	0.58335 (18)	0.7992 (4)	0.07547 (14)	0.1056 (8)
O3	0.56871 (18)	1.1638 (4)	0.11968 (12)	0.0901 (7)
O4	0.1795 (2)	0.1450 (4)	0.15547 (16)	0.1094 (9)
O5	0.1800 (2)	0.0787 (4)	0.04028 (14)	0.0949 (7)
N1	0.20241 (18)	0.1888 (4)	0.09722 (15)	0.0705 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0768 (5)	0.0848 (6)	0.0604 (5)	−0.0147 (4)	0.0373 (4)	−0.0034 (3)
C1	0.0608 (14)	0.0552 (14)	0.0448 (12)	0.0025 (11)	0.0187 (10)	0.0049 (11)
C2	0.0746 (16)	0.0619 (16)	0.0507 (14)	0.0009 (12)	0.0304 (12)	−0.0052 (12)
C3	0.0741 (16)	0.0690 (17)	0.0507 (15)	0.0013 (13)	0.0337 (12)	0.0051 (12)
C4	0.0581 (14)	0.0527 (14)	0.0511 (14)	0.0055 (11)	0.0168 (11)	0.0068 (11)
C5	0.0781 (17)	0.0737 (18)	0.0491 (14)	−0.0039 (14)	0.0254 (13)	−0.0083 (12)
C6	0.0809 (18)	0.085 (2)	0.0436 (14)	−0.0105 (15)	0.0306 (13)	−0.0030 (13)
C7	0.0517 (13)	0.0586 (15)	0.0676 (16)	−0.0013 (12)	0.0252 (12)	0.0026 (12)
C8	0.0627 (16)	0.0708 (19)	0.124 (3)	0.0023 (15)	0.0362 (18)	−0.0020 (19)
C9	0.065 (2)	0.092 (3)	0.167 (5)	0.0121 (17)	0.014 (2)	0.057 (3)
C10	0.080 (2)	0.154 (4)	0.098 (3)	−0.011 (3)	0.001 (2)	0.056 (3)
C11	0.0654 (18)	0.120 (3)	0.0612 (19)	−0.0228 (19)	0.0052 (14)	0.0139 (18)
C12	0.0504 (13)	0.0711 (17)	0.0525 (15)	−0.0091 (12)	0.0158 (11)	0.0008 (12)
C13	0.101 (3)	0.224 (6)	0.0479 (19)	−0.057 (3)	0.0186 (19)	−0.009 (3)
C14	0.119 (4)	0.214 (6)	0.096 (4)	−0.058 (4)	0.058 (3)	−0.076 (4)
C15	0.095 (2)	0.116 (3)	0.112 (3)	−0.019 (2)	0.052 (2)	−0.053 (2)
C16	0.0740 (18)	0.0747 (19)	0.0751 (19)	−0.0021 (15)	0.0312 (15)	−0.0112 (15)
O1	0.0746 (12)	0.0641 (12)	0.0561 (11)	−0.0065 (9)	0.0206 (9)	0.0071 (8)
O2	0.1001 (16)	0.145 (2)	0.0946 (16)	−0.0191 (15)	0.0642 (14)	−0.0393 (15)
O3	0.1088 (17)	0.0895 (15)	0.0763 (14)	−0.0348 (12)	0.0328 (12)	0.0139 (11)
O4	0.151 (2)	0.0943 (17)	0.1024 (19)	−0.0314 (15)	0.0678 (18)	0.0109 (14)
O5	0.1127 (19)	0.0819 (16)	0.0837 (17)	−0.0223 (12)	0.0167 (13)	−0.0090 (12)
N1	0.0763 (15)	0.0610 (15)	0.0735 (17)	0.0015 (11)	0.0196 (13)	0.0074 (13)

Geometric parameters (Å, º) top

S1—O2	1.415 (2)	C8—C9	1.418 (6)
S1—O3	1.419 (2)	C8—H8	0.9300
S1—O1	1.602 (2)	C9—C10	1.346 (6)
S1—C7	1.751 (3)	C9—H9	0.9300
C1—C6	1.367 (4)	C10—C11	1.374 (6)
C1—C2	1.374 (3)	C10—H10	0.9300
C1—O1	1.405 (3)	C11—C12	1.414 (4)
C2—C3	1.364 (4)	C11—C13	1.435 (6)
C2—H2	0.9300	C12—C16	1.406 (4)
C3—C4	1.368 (4)	C13—C14	1.345 (7)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.375 (4)	C14—C15	1.361 (7)
C4—N1	1.466 (3)	C14—H14	0.9300
C5—C6	1.369 (4)	C15—C16	1.350 (4)
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.368 (4)	O4—N1	1.218 (3)
C7—C12	1.422 (4)	O5—N1	1.215 (3)

O2—S1—O3	120.53 (15)	C9—C8—H8	120.6
O2—S1—O1	108.88 (12)	C10—C9—C8	120.3 (4)
O3—S1—O1	103.19 (12)	C10—C9—H9	119.9
O2—S1—C7	108.34 (15)	C8—C9—H9	119.9
O3—S1—C7	111.42 (13)	C9—C10—C11	121.7 (4)
O1—S1—C7	102.92 (10)	C9—C10—H10	119.1
C6—C1—C2	122.2 (2)	C11—C10—H10	119.1
C6—C1—O1	120.9 (2)	C10—C11—C12	120.5 (4)
C2—C1—O1	116.9 (2)	C10—C11—C13	121.8 (4)
C3—C2—C1	119.1 (2)	C12—C11—C13	117.7 (4)
C3—C2—H2	120.5	C16—C12—C11	118.3 (3)
C1—C2—H2	120.5	C16—C12—C7	124.8 (2)
C2—C3—C4	118.9 (2)	C11—C12—C7	116.9 (3)
C2—C3—H3	120.5	C14—C13—C11	121.1 (4)
C4—C3—H3	120.5	C14—C13—H13	119.5
C3—C4—C5	122.1 (2)	C11—C13—H13	119.5
C3—C4—N1	118.3 (2)	C13—C14—C15	120.3 (4)
C5—C4—N1	119.6 (2)	C13—C14—H14	119.9
C6—C5—C4	119.0 (2)	C15—C14—H14	119.9
C6—C5—H5	120.5	C16—C15—C14	121.7 (4)
C4—C5—H5	120.5	C16—C15—H15	119.1
C1—C6—C5	118.8 (2)	C14—C15—H15	119.1
C1—C6—H6	120.6	C15—C16—C12	120.9 (3)
C5—C6—H6	120.6	C15—C16—H16	119.5
C8—C7—C12	121.8 (3)	C12—C16—H16	119.5
C8—C7—S1	117.4 (2)	C1—O1—S1	119.41 (15)
C12—C7—S1	120.8 (2)	O5—N1—O4	123.7 (3)
C7—C8—C9	118.8 (4)	O5—N1—C4	118.6 (2)
C7—C8—H8	120.6	O4—N1—C4	117.7 (3)

C6—C1—C2—C3	−0.5 (4)	C13—C11—C12—C16	−1.2 (4)
O1—C1—C2—C3	175.8 (2)	C10—C11—C12—C7	0.1 (4)
C1—C2—C3—C4	0.1 (4)	C13—C11—C12—C7	−179.1 (3)
C2—C3—C4—C5	0.4 (4)	C8—C7—C12—C16	−176.5 (3)
C2—C3—C4—N1	−179.1 (2)	S1—C7—C12—C16	3.0 (3)
C3—C4—C5—C6	−0.3 (4)	C8—C7—C12—C11	1.3 (4)
N1—C4—C5—C6	179.1 (2)	S1—C7—C12—C11	−179.13 (19)
C2—C1—C6—C5	0.5 (4)	C10—C11—C13—C14	−177.4 (4)
O1—C1—C6—C5	−175.6 (2)	C12—C11—C13—C14	1.8 (6)
C4—C5—C6—C1	−0.1 (4)	C11—C13—C14—C15	−1.7 (7)
O2—S1—C7—C8	0.1 (3)	C13—C14—C15—C16	0.9 (7)
O3—S1—C7—C8	−134.7 (2)	C14—C15—C16—C12	−0.3 (5)
O1—S1—C7—C8	115.3 (2)	C11—C12—C16—C15	0.5 (4)
O2—S1—C7—C12	−179.42 (19)	C7—C12—C16—C15	178.3 (3)
O3—S1—C7—C12	45.8 (2)	C6—C1—O1—S1	−78.7 (3)
O1—S1—C7—C12	−64.2 (2)	C2—C1—O1—S1	104.9 (2)
C12—C7—C8—C9	−2.0 (4)	O2—S1—O1—C1	54.4 (2)
S1—C7—C8—C9	178.4 (2)	O3—S1—O1—C1	−176.40 (18)
C7—C8—C9—C10	1.3 (5)	C7—S1—O1—C1	−60.4 (2)
C8—C9—C10—C11	0.1 (6)	C3—C4—N1—O5	170.0 (3)
C9—C10—C11—C12	−0.8 (5)	C5—C4—N1—O5	−9.4 (4)
C9—C10—C11—C13	178.4 (4)	C3—C4—N1—O4	−12.0 (4)
C10—C11—C12—C16	178.0 (3)	C5—C4—N1—O4	168.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2	0.93	2.43	2.829 (5)	106
C16—H16···O3	0.93	2.46	3.058 (4)	122
C5—H5···O2ⁱ	0.93	2.48	3.179 (3)	132
C15—H15···O4ⁱⁱ	0.93	2.47	3.340 (5)	155

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁NO₅S
M_r	329.32
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	13.4407 (8), 6.2990 (3), 18.2556 (12)
β (°)	106.296 (2)
V (Å³)	1483.48 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.28 × 0.20 × 0.16

Data collection
Diffractometer	Bruker Kappa APEX2 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.935, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	14281, 2801, 1935
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.611

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.160, 1.08
No. of reflections	2801
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.20

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
C8—H8···O2	0.93	2.43	2.829 (5)	106
C16—H16···O3	0.93	2.46	3.058 (4)	122
C5—H5···O2ⁱ	0.93	2.48	3.179 (3)	132
C15—H15···O4ⁱⁱ	0.93	2.47	3.340 (5)	155

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

Acknowledgements

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

References

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