3-tert-Butyl-5,6,8-trinitro­naphtho[1,8a,8-cd][1,2]dithiole

Jiang, Y.; Wan, X.; Chen, Y.

doi:10.1107/S160053680800946X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o830

doi:10.1107/S160053680800946X

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3-tert-Butyl-5,6,8-trinitronaphtho[1,8a,8-cd][1,2]dithiole

Yuqin Jiang,^a Xiangjian Wan ^a and Yongsheng Chen ^a ^*

^aKey Laboratory for Functional Polymer Materials and Center for Nanoscale Science and Technology, Institute of Polymer Chemistry, College of Chemistry, Nankai University, Weijin Road No. 94, Tianjin, People's Republic of China
^*Correspondence e-mail: yschen99@nankai.edu.cn

(Received 18 March 2008; accepted 7 April 2008; online 10 April 2008)

Nitration of 2,7-di-tert-butylnaphthalene 1,8-disulfide with fuming nitric acid in 1:3 molar ratio gives the title compound, C₁₄H₁₁N₃O₆S₂. A tape motif is formed by weak head-to-tail interactions (3.131 Å) between S and NO₂ O atoms of a symmetry-related molecule.

Related literature

For related literature, see: Barltrop et al. (1954 ); Claeson et al. (1960 ); Shigeru et al. (1982 ); Smiles & Price (1928 ); Stepanov et al. (1977 ); Tesmer & Vahrenkamp (2001 ); Zweig & Hoffman (1965 ); Ashe et al. (1994 ).

Experimental

Crystal data

C₁₄H₁₁N₃O₆S₂
M_r = 381.38
Monoclinic, C 2/c
a = 19.477 (3) Å
b = 20.754 (4) Å
c = 8.1658 (14) Å
β = 105.909 (3)°
V = 3174.4 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 294 (2) K
0.26 × 0.24 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.876, T_max = 0.964
8118 measured reflections
2803 independent reflections
1856 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.108
S = 1.03
2803 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800946X/pk2089sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680800946X/pk2089Isup2.hkl

checkCIF report

Comment top

Naphthalene-1,8-disulfide is a bright-red crystalline compound (Smiles et al., 1928; Zweig et al., 1965) due to the introduction of S—S group into the naphthalene ring leading to a considerable bathochromic shift of the absorption bands characteristic of disulfides in the electronic spectrum (Barltrop et al., 1954; Claeson et al., 1960). There are only a few reports concerning the nitration of naphthalene-1,8-disulfide (Stepanov et al., 1977; Shigeru et al., 1982). In an attempt to nitrate 2,7-di-tert-butyl-naphthalene-1,8-disulfide(BNT) (Tesmer et al., 2001) with fuming nitric acid in an attempted synthesis of 3,8-di-tert-butyl-5,6-dinitro-naphtho[1,8-cd][1,2]dithiole, the title compound was obtained unexpectedly. Herein, we present its preparation and single-crystal structure (Fig. 1).

The crystal was obtained by recrystallization from ethyl acetate. The length of the S—S bond is 2.0627 (10) Å, which is consistent with that of analogues reported by Arthur et al. (1994). The three rings form a slightly non-perfect plane owing to the asymmetric substitution of nitro and tert-butyl groups. The dihedral angles between the rings are: A/B, 3.9 (3) °; A/C, 2.3 (3) °; B/C, 3.0 (3) °. A perspective view of the packing is shown in Figure 2. A slightly wavy tape motif is formed by the head-to-tail weak interactions between S1 and O2 of a molecule related via 0.5+x,0.5-y,0.5+z.

Related literature top

For related literature, see: Barltrop et al. (1954); Claeson et al. (1960); Shigeru et al. (1982); Smiles & Price (1928); Stepanov et al. (1977); Tesmer & Vahrenkamp (2001); Zweig & Hoffman (1965); Ashe et al. (1994).

Experimental top

To a solution of BNT (3.02 g, 10 mmol) in acetic acid (50 mL), fuming nitric acid (30 mmol) was added. The reaction mixture was stirred for 0.5 h and cooled to room temperature. The precipitate was collected by filtration and recrystallized from ethyl acetate to give the title compound as red crystals, yield 80%.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound showing 30% probability ellipsoids.
	Fig. 2. Packing structure of the title compound.

3-tert-Butyl-5,6,8-trinitronaphtho[1,8a,8-cd][1,2]dithiole top

Crystal data top

C₁₄H₁₁N₃O₆S₂	F(000) = 1568
M_r = 381.38	D_x = 1.596 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2099 reflections
a = 19.477 (3) Å	θ = 2.7–25.8°
b = 20.754 (4) Å	µ = 0.37 mm⁻¹
c = 8.1658 (14) Å	T = 294 K
β = 105.909 (3)°	Block, red
V = 3174.4 (10) Å³	0.26 × 0.24 × 0.10 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	2803 independent reflections
Radiation source: fine-focus sealed tube	1856 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −19→23
T_min = 0.876, T_max = 0.964	k = −24→22
8118 measured reflections	l = −9→9

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0578P)²] where P = (F_o² + 2F_c²)/3
2803 reflections	(Δ/σ)_max = 0.001
229 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₄H₁₁N₃O₆S₂	V = 3174.4 (10) Å³
M_r = 381.38	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 19.477 (3) Å	µ = 0.37 mm⁻¹
b = 20.754 (4) Å	T = 294 K
c = 8.1658 (14) Å	0.26 × 0.24 × 0.10 mm
β = 105.909 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2803 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	1856 reflections with I > 2σ(I)
T_min = 0.876, T_max = 0.964	R_int = 0.037
8118 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
2803 reflections	Δρ_min = −0.26 e Å⁻³
229 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
S1	0.22607 (3)	0.26843 (3)	0.74057 (9)	0.0476 (2)
S2	0.21867 (3)	0.17028 (3)	0.77160 (9)	0.0490 (2)
O1	−0.10572 (11)	0.34597 (11)	0.3300 (3)	0.0838 (7)
O2	−0.12517 (9)	0.26776 (9)	0.4864 (2)	0.0525 (5)
O3	−0.10009 (10)	0.18790 (11)	0.2446 (2)	0.0661 (6)
O4	−0.12944 (10)	0.12220 (10)	0.4212 (3)	0.0665 (6)
O5	0.08457 (13)	0.00261 (10)	0.7190 (3)	0.1019 (9)
O6	0.18753 (12)	0.05183 (10)	0.7857 (3)	0.0809 (7)
N1	−0.08510 (11)	0.30111 (12)	0.4295 (3)	0.0494 (6)
N2	−0.08763 (12)	0.15858 (12)	0.3800 (3)	0.0513 (6)
N3	0.12234 (14)	0.05040 (12)	0.7216 (3)	0.0693 (8)
C1	0.13641 (12)	0.28171 (11)	0.6422 (3)	0.0349 (6)
C2	0.09381 (12)	0.22503 (11)	0.6122 (3)	0.0332 (6)
C3	0.12897 (13)	0.16621 (11)	0.6715 (3)	0.0378 (6)
C4	0.08893 (14)	0.10991 (12)	0.6509 (3)	0.0469 (7)
C5	0.01708 (14)	0.10991 (13)	0.5605 (3)	0.0487 (7)
H5	−0.0084	0.0714	0.5431	0.058*
C6	−0.01603 (12)	0.16565 (12)	0.4978 (3)	0.0402 (6)
C7	0.01938 (12)	0.22687 (11)	0.5293 (3)	0.0349 (6)
C8	−0.00856 (12)	0.28886 (12)	0.4886 (3)	0.0378 (6)
C9	0.03362 (13)	0.34351 (12)	0.5203 (3)	0.0418 (6)
H9	0.0116	0.3831	0.4882	0.050*
C10	0.10644 (13)	0.34324 (12)	0.5964 (3)	0.0388 (6)
C11	0.14946 (14)	0.40632 (12)	0.6359 (3)	0.0445 (7)
C12	0.20882 (15)	0.40735 (14)	0.5453 (4)	0.0603 (8)
H12A	0.2363	0.4462	0.5746	0.090*
H12B	0.1880	0.4058	0.4244	0.090*
H12C	0.2394	0.3707	0.5803	0.090*
C13	0.18252 (17)	0.41303 (14)	0.8288 (3)	0.0655 (9)
H13A	0.2145	0.3777	0.8691	0.098*
H13B	0.1453	0.4127	0.8853	0.098*
H13C	0.2084	0.4529	0.8523	0.098*
C14	0.10141 (16)	0.46540 (13)	0.5768 (4)	0.0678 (9)
H14A	0.1295	0.5040	0.6038	0.102*
H14B	0.0643	0.4661	0.6338	0.102*
H14C	0.0804	0.4631	0.4560	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0239 (3)	0.0561 (5)	0.0571 (5)	0.0011 (3)	0.0013 (3)	−0.0029 (3)
S2	0.0287 (4)	0.0533 (4)	0.0576 (5)	0.0105 (3)	−0.0008 (3)	−0.0063 (3)
O1	0.0463 (13)	0.1089 (19)	0.0858 (15)	0.0205 (12)	0.0004 (11)	0.0525 (15)
O2	0.0270 (10)	0.0763 (14)	0.0557 (12)	0.0019 (9)	0.0140 (9)	0.0021 (10)
O3	0.0457 (12)	0.1145 (17)	0.0317 (10)	0.0013 (11)	0.0000 (9)	−0.0013 (11)
O4	0.0399 (12)	0.0745 (15)	0.0789 (14)	−0.0160 (11)	0.0057 (11)	−0.0059 (11)
O5	0.0882 (18)	0.0412 (13)	0.155 (3)	−0.0054 (12)	−0.0030 (17)	−0.0026 (14)
O6	0.0535 (14)	0.0582 (13)	0.1134 (19)	0.0205 (11)	−0.0069 (13)	−0.0051 (12)
N1	0.0285 (12)	0.0749 (17)	0.0422 (13)	0.0080 (11)	0.0051 (10)	0.0072 (12)
N2	0.0314 (13)	0.0721 (17)	0.0468 (14)	−0.0024 (12)	0.0050 (11)	−0.0145 (12)
N3	0.0602 (18)	0.0427 (15)	0.093 (2)	0.0105 (14)	0.0005 (16)	−0.0149 (14)
C1	0.0269 (13)	0.0478 (15)	0.0289 (13)	0.0022 (11)	0.0060 (10)	−0.0008 (11)
C2	0.0247 (13)	0.0481 (15)	0.0252 (12)	0.0044 (11)	0.0042 (10)	−0.0027 (10)
C3	0.0315 (13)	0.0438 (15)	0.0352 (13)	0.0043 (11)	0.0041 (11)	−0.0106 (11)
C4	0.0418 (16)	0.0425 (16)	0.0504 (16)	0.0070 (13)	0.0027 (13)	−0.0099 (13)
C5	0.0423 (16)	0.0485 (17)	0.0507 (17)	−0.0061 (13)	0.0053 (13)	−0.0127 (13)
C6	0.0269 (13)	0.0571 (17)	0.0336 (14)	−0.0022 (12)	0.0032 (11)	−0.0081 (12)
C7	0.0292 (13)	0.0541 (16)	0.0219 (12)	0.0015 (11)	0.0079 (10)	−0.0016 (11)
C8	0.0248 (13)	0.0569 (17)	0.0303 (13)	0.0072 (12)	0.0051 (10)	0.0064 (12)
C9	0.0395 (15)	0.0478 (17)	0.0383 (14)	0.0105 (12)	0.0107 (12)	0.0116 (12)
C10	0.0350 (14)	0.0505 (17)	0.0313 (13)	0.0015 (12)	0.0097 (11)	0.0039 (11)
C11	0.0460 (17)	0.0451 (16)	0.0410 (15)	−0.0004 (12)	0.0097 (13)	0.0026 (12)
C12	0.0556 (19)	0.066 (2)	0.0591 (19)	−0.0194 (15)	0.0155 (15)	−0.0042 (14)
C13	0.094 (3)	0.0513 (18)	0.0480 (18)	−0.0007 (16)	0.0145 (17)	−0.0109 (14)
C14	0.068 (2)	0.0496 (18)	0.082 (2)	0.0001 (15)	0.0139 (17)	0.0122 (15)

Geometric parameters (Å, º) top

S1—C1	1.733 (2)	C5—H5	0.9300
S1—S2	2.0627 (10)	C6—C7	1.435 (3)
S2—C3	1.716 (2)	C7—C8	1.401 (3)
O1—N1	1.229 (3)	C8—C9	1.383 (3)
O2—N1	1.226 (3)	C9—C10	1.384 (3)
O3—N2	1.227 (3)	C9—H9	0.9300
O4—N2	1.223 (3)	C10—C11	1.540 (3)
O5—N3	1.231 (3)	C11—C12	1.534 (4)
O6—N3	1.234 (3)	C11—C13	1.536 (3)
N1—C8	1.458 (3)	C11—C14	1.538 (4)
N2—C6	1.468 (3)	C12—H12A	0.9600
N3—C4	1.441 (3)	C12—H12B	0.9600
C1—C10	1.411 (3)	C12—H12C	0.9600
C1—C2	1.421 (3)	C13—H13A	0.9600
C2—C3	1.419 (3)	C13—H13B	0.9600
C2—C7	1.422 (3)	C13—H13C	0.9600
C3—C4	1.389 (3)	C14—H14A	0.9600
C4—C5	1.392 (3)	C14—H14B	0.9600
C5—C6	1.355 (3)	C14—H14C	0.9600

C1—S1—S2	96.81 (8)	C9—C8—N1	114.8 (2)
C3—S2—S1	94.96 (9)	C7—C8—N1	122.3 (2)
O2—N1—O1	123.5 (2)	C8—C9—C10	124.3 (2)
O2—N1—C8	118.4 (2)	C8—C9—H9	117.8
O1—N1—C8	118.1 (2)	C10—C9—H9	117.8
O4—N2—O3	124.9 (2)	C9—C10—C1	114.9 (2)
O4—N2—C6	117.8 (2)	C9—C10—C11	121.5 (2)
O3—N2—C6	117.3 (2)	C1—C10—C11	123.5 (2)
O5—N3—O6	124.5 (3)	C12—C11—C13	109.5 (2)
O5—N3—C4	118.8 (3)	C12—C11—C14	108.2 (2)
O6—N3—C4	116.6 (3)	C13—C11—C14	107.3 (2)
C10—C1—C2	121.6 (2)	C12—C11—C10	110.5 (2)
C10—C1—S1	123.91 (18)	C13—C11—C10	110.1 (2)
C2—C1—S1	114.50 (17)	C14—C11—C10	111.3 (2)
C3—C2—C1	116.7 (2)	C11—C12—H12A	109.5
C3—C2—C7	121.3 (2)	C11—C12—H12B	109.5
C1—C2—C7	122.0 (2)	H12A—C12—H12B	109.5
C4—C3—C2	118.7 (2)	C11—C12—H12C	109.5
C4—C3—S2	124.31 (19)	H12A—C12—H12C	109.5
C2—C3—S2	116.97 (18)	H12B—C12—H12C	109.5
C3—C4—C5	120.9 (2)	C11—C13—H13A	109.5
C3—C4—N3	119.7 (2)	C11—C13—H13B	109.5
C5—C4—N3	119.4 (2)	H13A—C13—H13B	109.5
C6—C5—C4	120.4 (2)	C11—C13—H13C	109.5
C6—C5—H5	119.8	H13A—C13—H13C	109.5
C4—C5—H5	119.8	H13B—C13—H13C	109.5
C5—C6—C7	122.2 (2)	C11—C14—H14A	109.5
C5—C6—N2	115.5 (2)	C11—C14—H14B	109.5
C7—C6—N2	122.0 (2)	H14A—C14—H14B	109.5
C8—C7—C2	114.6 (2)	C11—C14—H14C	109.5
C8—C7—C6	129.4 (2)	H14A—C14—H14C	109.5
C2—C7—C6	116.0 (2)	H14B—C14—H14C	109.5
C9—C8—C7	122.5 (2)

C1—S1—S2—C3	2.27 (11)	C1—C2—C7—C8	−3.2 (3)
S2—S1—C1—C10	176.23 (18)	C3—C2—C7—C6	−4.8 (3)
S2—S1—C1—C2	−2.85 (17)	C1—C2—C7—C6	176.2 (2)
C10—C1—C2—C3	−176.8 (2)	C5—C6—C7—C8	−173.2 (2)
S1—C1—C2—C3	2.3 (3)	N2—C6—C7—C8	13.8 (4)
C10—C1—C2—C7	2.3 (3)	C5—C6—C7—C2	7.6 (3)
S1—C1—C2—C7	−178.63 (16)	N2—C6—C7—C2	−165.4 (2)
C1—C2—C3—C4	177.5 (2)	C2—C7—C8—C9	2.6 (3)
C7—C2—C3—C4	−1.5 (3)	C6—C7—C8—C9	−176.7 (2)
C1—C2—C3—S2	−0.2 (3)	C2—C7—C8—N1	−169.64 (19)
C7—C2—C3—S2	−179.27 (17)	C6—C7—C8—N1	11.1 (4)
S1—S2—C3—C4	−179.1 (2)	O2—N1—C8—C9	−138.7 (2)
S1—S2—C3—C2	−1.51 (19)	O1—N1—C8—C9	38.6 (3)
C2—C3—C4—C5	5.7 (4)	O2—N1—C8—C7	34.1 (3)
S2—C3—C4—C5	−176.7 (2)	O1—N1—C8—C7	−148.6 (3)
C2—C3—C4—N3	−175.3 (2)	C7—C8—C9—C10	−1.0 (4)
S2—C3—C4—N3	2.3 (4)	N1—C8—C9—C10	171.8 (2)
O5—N3—C4—C3	171.9 (3)	C8—C9—C10—C1	−0.2 (4)
O6—N3—C4—C3	−6.0 (4)	C8—C9—C10—C11	−176.9 (2)
O5—N3—C4—C5	−9.0 (4)	C2—C1—C10—C9	−0.5 (3)
O6—N3—C4—C5	173.0 (3)	S1—C1—C10—C9	−179.49 (17)
C3—C4—C5—C6	−3.2 (4)	C2—C1—C10—C11	176.2 (2)
N3—C4—C5—C6	177.8 (2)	S1—C1—C10—C11	−2.8 (3)
C4—C5—C6—C7	−3.7 (4)	C9—C10—C11—C12	−121.4 (3)
C4—C5—C6—N2	169.7 (2)	C1—C10—C11—C12	62.2 (3)
O4—N2—C6—C5	46.7 (3)	C9—C10—C11—C13	117.6 (3)
O3—N2—C6—C5	−130.7 (3)	C1—C10—C11—C13	−58.8 (3)
O4—N2—C6—C7	−139.9 (2)	C9—C10—C11—C14	−1.2 (3)
O3—N2—C6—C7	42.7 (3)	C1—C10—C11—C14	−177.6 (2)
C3—C2—C7—C8	175.8 (2)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁N₃O₆S₂
M_r	381.38
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	294
a, b, c (Å)	19.477 (3), 20.754 (4), 8.1658 (14)
β (°)	105.909 (3)
V (Å³)	3174.4 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.26 × 0.24 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.876, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	8118, 2803, 1856
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.108, 1.03
No. of reflections	2803
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.26

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the NSFC (grant Nos. 20644004, 20774047), MoST (grant No. 2006CB932702) and the NSF of Tianjin City (grant No. 07JCYBJC03000).

References

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