4-Nitro-phenyl naphthalene-1-sulfonate.

In the crystal structure of the title compound, C(16)H(11)NO(5)S, 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 inter-molecular C-H⋯O inter-actions 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 = 329.32

Monoclinic,

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 (; 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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.160

S = 1.08

2801 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.20 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027396/is2328sup1.cif

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

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

C16H11NO5S	F000 = 680
Mr = 329.32	Dx = 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 = 2.2–25.4º
b = 6.2990 (3) Å	µ = 0.24 mm−1
c = 18.2556 (12) Å	T = 295 (2) K
β = 106.296 (2)º	Block, yellow
V = 1483.48 (15) Å3	0.28 × 0.20 × 0.16 mm
Z = 4

Bruker Kappa APEX2 diffractometer	2801 independent reflections
Radiation source: fine-focus sealed tube	1935 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.041
T = 295(2) K	θmax = 25.7º
ω and φ scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.935, Tmax = 0.962	k = −7→5
14281 measured reflections	l = −22→22

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.160	w = 1/[σ2(Fo2) + (0.0801P)2 + 0.4092P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2801 reflections	Δρmax = 0.25 e Å−3
208 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .