2,4-Dinitro-1-naphthyl 4-toluene-sulfonate.

In the title compound, C(17)H(12)N(2)O(7)S, the dihedral angle between the benzene ring and the naphthyl plane is 26.34 (6)°. The nitro groups make dihedral angles of 40.09 (4) and 37.05 (3)° with the naphthyl plane. In the crystal structure, weak intra- and inter-molecular C-H⋯O inter-actions are observed.

Related literature

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

Experimental

Crystal data

C17H12N2O7S

M = 388.35

Monoclinic,

a = 13.071 (2) Å

b = 7.8660 (13) Å

c = 16.595 (3) Å

β = 90.757 (3)°

V = 1706.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 295 (2) K

0.36 × 0.25 × 0.13 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.920, T max = 0.970

12222 measured reflections

3116 independent reflections

2291 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.104

S = 1.02

3116 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.23 e Å−3

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/S1600536808010052/is2287sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010052/is2287Isup2.hkl

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

C17H12N2O7S	F000 = 800
Mr = 388.35	Dx = 1.512 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4023 reflections
a = 13.071 (2) Å	θ = 1.8–25.2º
b = 7.8660 (13) Å	µ = 0.24 mm−1
c = 16.595 (3) Å	T = 295 (2) K
β = 90.757 (3)º	Block, colourless
V = 1706.0 (5) Å3	0.36 × 0.25 × 0.13 mm
Z = 4

Bruker Kappa APEXII diffractometer	3116 independent reflections
Radiation source: fine-focus sealed tube	2291 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
T = 295(2) K	θmax = 25.4º
ω and φ scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.920, Tmax = 0.970	k = −9→9
12222 measured reflections	l = −19→19

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0486P)2 + 0.4765P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3116 reflections	Δρmax = 0.20 e Å−3
245 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
S1	0.75961 (5)	0.14928 (8)	0.91732 (3)	0.04636 (19)
N2	0.47400 (18)	0.4441 (3)	1.21402 (12)	0.0509 (5)
N1	0.77051 (15)	0.1383 (3)	1.12836 (11)	0.0511 (5)
C8	0.62399 (17)	0.1694 (3)	1.03092 (12)	0.0379 (5)
C9	0.66905 (17)	0.2018 (3)	1.10432 (13)	0.0396 (5)
C10	0.61838 (18)	0.2985 (3)	1.16206 (13)	0.0418 (5)
H10	0.6505	0.3244	1.2109	0.050*
C11	0.52268 (18)	0.3540 (3)	1.14659 (12)	0.0394 (5)
C12	0.47017 (17)	0.3258 (3)	1.07210 (12)	0.0383 (5)
C13	0.52516 (16)	0.2336 (3)	1.01249 (12)	0.0366 (5)
C14	0.37180 (18)	0.3875 (3)	1.05167 (14)	0.0462 (6)
H14	0.3347	0.4476	1.0897	0.055*
C15	0.33082 (18)	0.3603 (3)	0.97732 (15)	0.0502 (6)
H15	0.2658	0.4016	0.9651	0.060*
C16	0.38494 (19)	0.2709 (3)	0.91879 (15)	0.0494 (6)
H16	0.3558	0.2542	0.8680	0.059*
C17	0.47966 (18)	0.2082 (3)	0.93546 (13)	0.0421 (5)
H17	0.5148	0.1484	0.8962	0.051*
C1	0.82025 (17)	−0.0380 (3)	0.88993 (14)	0.0467 (6)
C4	0.9179 (2)	−0.3362 (4)	0.84598 (18)	0.0639 (7)
C2	0.8941 (2)	−0.1075 (4)	0.94025 (17)	0.0660 (8)
H2	0.9113	−0.0548	0.9888	0.079*
C3	0.9421 (2)	−0.2557 (4)	0.91778 (19)	0.0744 (9)
H3	0.9918	−0.3026	0.9516	0.089*
C6	0.7943 (2)	−0.1167 (4)	0.81845 (15)	0.0583 (7)
H6	0.7439	−0.0708	0.7848	0.070*
C5	0.8437 (2)	−0.2639 (4)	0.79741 (18)	0.0671 (8)
H5	0.8264	−0.3163	0.7489	0.081*
C7	0.9719 (2)	−0.4974 (4)	0.8216 (2)	0.0947 (11)
H7A	1.0222	−0.4715	0.7818	0.142*
H7B	0.9230	−0.5762	0.7995	0.142*
H7C	1.0049	−0.5470	0.8680	0.142*
O1	0.70983 (14)	0.2246 (2)	0.84979 (9)	0.0613 (5)
O2	0.82266 (13)	0.2523 (2)	0.96766 (10)	0.0584 (5)
O3	0.67103 (11)	0.06829 (18)	0.97377 (8)	0.0431 (4)
O4	0.82359 (15)	0.2326 (3)	1.16921 (12)	0.0810 (6)
O5	0.79512 (14)	−0.0046 (3)	1.10830 (11)	0.0644 (5)
O6	0.53013 (16)	0.5300 (3)	1.25734 (11)	0.0738 (6)
O7	0.38300 (16)	0.4246 (3)	1.22514 (11)	0.0713 (6)

	U11	U22	U33	U12	U13	U23
S1	0.0527 (4)	0.0503 (4)	0.0362 (3)	−0.0065 (3)	0.0072 (3)	−0.0017 (3)
N2	0.0698 (15)	0.0451 (12)	0.0382 (11)	0.0054 (11)	0.0093 (11)	0.0005 (9)
N1	0.0516 (13)	0.0644 (15)	0.0372 (11)	−0.0010 (12)	−0.0001 (9)	0.0005 (11)
C8	0.0473 (13)	0.0341 (12)	0.0324 (11)	−0.0068 (10)	0.0055 (10)	0.0000 (9)
C9	0.0447 (13)	0.0384 (12)	0.0358 (12)	−0.0044 (10)	0.0001 (10)	0.0041 (10)
C10	0.0582 (15)	0.0389 (12)	0.0285 (11)	−0.0081 (11)	0.0000 (10)	0.0002 (10)
C11	0.0532 (14)	0.0313 (11)	0.0338 (11)	−0.0022 (10)	0.0087 (10)	0.0017 (9)
C12	0.0485 (13)	0.0300 (11)	0.0364 (12)	−0.0069 (10)	0.0043 (10)	0.0048 (9)
C13	0.0446 (13)	0.0309 (11)	0.0344 (11)	−0.0090 (10)	0.0013 (10)	0.0028 (9)
C14	0.0521 (14)	0.0383 (13)	0.0485 (14)	−0.0017 (11)	0.0078 (11)	0.0060 (11)
C15	0.0448 (14)	0.0490 (14)	0.0566 (15)	−0.0038 (11)	−0.0045 (12)	0.0106 (13)
C16	0.0564 (15)	0.0488 (14)	0.0427 (13)	−0.0126 (12)	−0.0088 (12)	0.0061 (11)
C17	0.0517 (14)	0.0394 (12)	0.0352 (12)	−0.0088 (11)	0.0001 (10)	0.0011 (10)
C1	0.0405 (13)	0.0579 (15)	0.0420 (13)	−0.0071 (11)	0.0076 (11)	−0.0057 (11)
C4	0.0484 (15)	0.0653 (18)	0.078 (2)	−0.0063 (14)	0.0158 (14)	−0.0175 (16)
C2	0.0531 (16)	0.087 (2)	0.0578 (16)	0.0052 (15)	−0.0036 (13)	−0.0213 (15)
C3	0.0555 (17)	0.089 (2)	0.079 (2)	0.0164 (16)	−0.0041 (15)	−0.0103 (18)
C6	0.0564 (16)	0.0690 (18)	0.0496 (15)	0.0026 (14)	0.0009 (12)	−0.0111 (13)
C5	0.0612 (17)	0.076 (2)	0.0641 (18)	−0.0081 (15)	0.0040 (14)	−0.0264 (16)
C7	0.075 (2)	0.077 (2)	0.133 (3)	0.0067 (18)	0.022 (2)	−0.028 (2)
O1	0.0794 (12)	0.0660 (12)	0.0387 (9)	0.0039 (9)	0.0059 (9)	0.0086 (8)
O2	0.0630 (11)	0.0584 (11)	0.0539 (10)	−0.0189 (9)	0.0080 (8)	−0.0100 (9)
O3	0.0514 (9)	0.0404 (9)	0.0377 (8)	−0.0031 (7)	0.0076 (7)	−0.0054 (7)
O4	0.0617 (12)	0.1075 (17)	0.0734 (13)	−0.0049 (11)	−0.0180 (11)	−0.0267 (12)
O5	0.0660 (12)	0.0632 (12)	0.0640 (12)	0.0149 (10)	−0.0005 (9)	0.0042 (10)
O6	0.0898 (15)	0.0723 (13)	0.0593 (12)	0.0021 (11)	0.0009 (11)	−0.0308 (10)
O7	0.0664 (13)	0.0885 (15)	0.0596 (12)	0.0031 (11)	0.0229 (10)	−0.0065 (10)

S1—O1	1.4179 (17)	C14—H14	0.9300
S1—O2	1.4196 (16)	C15—C16	1.399 (3)
S1—O3	1.6287 (16)	C15—H15	0.9300
S1—C1	1.736 (3)	C16—C17	1.358 (3)
N2—O7	1.216 (3)	C16—H16	0.9300
N2—O6	1.224 (3)	C17—H17	0.9300
N2—C11	1.476 (3)	C1—C6	1.377 (3)
N1—O4	1.216 (3)	C1—C2	1.381 (3)
N1—O5	1.216 (3)	C4—C5	1.376 (4)
N1—C9	1.467 (3)	C4—C3	1.382 (4)
C8—C9	1.370 (3)	C4—C7	1.509 (4)
C8—O3	1.388 (2)	C2—C3	1.378 (4)
C8—C13	1.416 (3)	C2—H2	0.9300
C9—C10	1.397 (3)	C3—H3	0.9300
C10—C11	1.346 (3)	C6—C5	1.373 (4)
C10—H10	0.9300	C6—H6	0.9300
C11—C12	1.423 (3)	C5—H5	0.9300
C12—C14	1.411 (3)	C7—H7A	0.9600
C12—C13	1.429 (3)	C7—H7B	0.9600
C13—C17	1.417 (3)	C7—H7C	0.9600
C14—C15	1.356 (3)
O1—S1—O2	118.91 (11)	C14—C15—H15	119.5
O1—S1—O3	107.20 (10)	C16—C15—H15	119.5
O2—S1—O3	107.24 (9)	C17—C16—C15	120.6 (2)
O1—S1—C1	110.71 (11)	C17—C16—H16	119.7
O2—S1—C1	112.01 (11)	C15—C16—H16	119.7
O3—S1—C1	98.58 (10)	C16—C17—C13	120.2 (2)
O7—N2—O6	124.1 (2)	C16—C17—H17	119.9
O7—N2—C11	119.1 (2)	C13—C17—H17	119.9
O6—N2—C11	116.7 (2)	C6—C1—C2	120.4 (2)
O4—N1—O5	124.4 (2)	C6—C1—S1	119.9 (2)
O4—N1—C9	116.8 (2)	C2—C1—S1	119.70 (19)
O5—N1—C9	118.8 (2)	C5—C4—C3	117.8 (3)
C9—C8—O3	121.7 (2)	C5—C4—C7	121.3 (3)
C9—C8—C13	120.4 (2)	C3—C4—C7	120.9 (3)
O3—C8—C13	117.89 (18)	C3—C2—C1	119.2 (3)
C8—C9—C10	120.6 (2)	C3—C2—H2	120.4
C8—C9—N1	123.7 (2)	C1—C2—H2	120.4
C10—C9—N1	115.71 (19)	C2—C3—C4	121.4 (3)
C11—C10—C9	119.6 (2)	C2—C3—H3	119.3
C11—C10—H10	120.2	C4—C3—H3	119.3
C9—C10—H10	120.2	C5—C6—C1	119.2 (3)
C10—C11—C12	123.4 (2)	C5—C6—H6	120.4
C10—C11—N2	114.8 (2)	C1—C6—H6	120.4
C12—C11—N2	121.7 (2)	C6—C5—C4	122.0 (3)
C14—C12—C11	125.6 (2)	C6—C5—H5	119.0
C14—C12—C13	118.3 (2)	C4—C5—H5	119.0
C11—C12—C13	116.1 (2)	C4—C7—H7A	109.5
C8—C13—C17	121.0 (2)	C4—C7—H7B	109.5
C8—C13—C12	119.83 (19)	H7A—C7—H7B	109.5
C17—C13—C12	119.1 (2)	C4—C7—H7C	109.5
C15—C14—C12	120.8 (2)	H7A—C7—H7C	109.5
C15—C14—H14	119.6	H7B—C7—H7C	109.5
C12—C14—H14	119.6	C8—O3—S1	119.58 (13)
C14—C15—C16	120.9 (2)
O3—C8—C9—C10	−177.46 (19)	C11—C12—C14—C15	176.7 (2)
C13—C8—C9—C10	0.0 (3)	C13—C12—C14—C15	−0.2 (3)
O3—C8—C9—N1	1.8 (3)	C12—C14—C15—C16	−0.2 (3)
C13—C8—C9—N1	179.21 (19)	C14—C15—C16—C17	0.5 (3)
O4—N1—C9—C8	143.2 (2)	C15—C16—C17—C13	−0.3 (3)
O5—N1—C9—C8	−38.6 (3)	C8—C13—C17—C16	−179.9 (2)
O4—N1—C9—C10	−37.5 (3)	C12—C13—C17—C16	−0.1 (3)
O5—N1—C9—C10	140.7 (2)	O1—S1—C1—C6	−17.0 (2)
C8—C9—C10—C11	2.9 (3)	O2—S1—C1—C6	−152.30 (19)
N1—C9—C10—C11	−176.4 (2)	O3—S1—C1—C6	95.1 (2)
C9—C10—C11—C12	−2.8 (3)	O1—S1—C1—C2	163.2 (2)
C9—C10—C11—N2	175.77 (19)	O2—S1—C1—C2	27.9 (2)
O7—N2—C11—C10	−143.1 (2)	O3—S1—C1—C2	−84.7 (2)
O6—N2—C11—C10	34.3 (3)	C6—C1—C2—C3	0.5 (4)
O7—N2—C11—C12	35.5 (3)	S1—C1—C2—C3	−179.7 (2)
O6—N2—C11—C12	−147.1 (2)	C1—C2—C3—C4	0.0 (5)
C10—C11—C12—C14	−177.1 (2)	C5—C4—C3—C2	−0.3 (4)
N2—C11—C12—C14	4.5 (3)	C7—C4—C3—C2	179.2 (3)
C10—C11—C12—C13	−0.1 (3)	C2—C1—C6—C5	−0.8 (4)
N2—C11—C12—C13	−178.59 (19)	S1—C1—C6—C5	179.4 (2)
C9—C8—C13—C17	176.87 (19)	C1—C6—C5—C4	0.6 (4)
O3—C8—C13—C17	−5.6 (3)	C3—C4—C5—C6	0.0 (4)
C9—C8—C13—C12	−2.9 (3)	C7—C4—C5—C6	−179.5 (3)
O3—C8—C13—C12	174.60 (17)	C9—C8—O3—S1	−80.6 (2)
C14—C12—C13—C8	−179.86 (19)	C13—C8—O3—S1	101.93 (19)
C11—C12—C13—C8	3.0 (3)	O1—S1—O3—C8	−86.68 (17)
C14—C12—C13—C17	0.3 (3)	O2—S1—O3—C8	42.07 (17)
C11—C12—C13—C17	−176.83 (19)	C1—S1—O3—C8	158.41 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O5	0.93	2.55	3.194 (3)	127
C14—H14···O7	0.93	2.33	2.895 (3)	119
C17—H17···O3	0.93	2.48	2.798 (3)	100
C10—H10···O1i	0.93	2.45	3.327 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O5	0.93	2.55	3.194 (3)	127
C14—H14⋯O7	0.93	2.33	2.895 (3)	119
C17—H17⋯O3	0.93	2.48	2.798 (3)	100
C10—H10⋯O1i	0.93	2.45	3.327 (3)	157

Symmetry code: (i) .