7-Nitro-1,2,3,4-tetra-hydro-naphthalene-1-spiro-2'-(1,3-dithiane).

In the title compound, C(13)H(15)NO(2)S(2), the nitro group is coplanar with the benzene ring to which it is attached, forming a dihedral angle of 1.07 (14)°. The dithiane ring adopts a chair conformation. In the crystal structure, mol-ecules are linked through C-H⋯O and C-H⋯π [C⋯Cg = 3.7164 (15) Å] inter-actions. The crystal studied was an inversion twin with an 0.134 (5):0.866 (5) domain ratio.

Related literature

For the calculation of ring puckering parameters, see: Cremer & Pople (1975 ▶). For related literature including applications, see: Goswami & Maity (2008 ▶); Fun et al. (2009 ▶).

Experimental

Crystal data

C13H15NO2S2

M = 281.38

Orthorhombic,

a = 12.8673 (1) Å

b = 42.2330 (6) Å

c = 9.1819 (1) Å

V = 4989.67 (10) Å3

Z = 16

Mo Kα radiation

μ = 0.42 mm−1

T = 100.0 (1) K

0.41 × 0.30 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.849, T max = 0.977

54206 measured reflections

6726 independent reflections

5979 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.077

S = 1.06

6726 reflections

164 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 3202 Friedel pairs

Flack parameter: 0.13 (5)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001536/tk2351sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001536/tk2351Isup2.hkl

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

C13H15NO2S2	F(000) = 2368
Mr = 281.38	Dx = 1.498 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 9946 reflections
a = 12.8673 (1) Å	θ = 2.8–35.0°
b = 42.2330 (6) Å	µ = 0.42 mm−1
c = 9.1819 (1) Å	T = 100 K
V = 4989.67 (10) Å3	Plate, colourless
Z = 16	0.41 × 0.30 × 0.06 mm

Bruker SMART APEXII CCD area-detector diffractometer	6726 independent reflections
Radiation source: fine-focus sealed tube	5979 reflections with I > 2σ(I)
graphite	Rint = 0.067
φ and ω scans	θmax = 37.9°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −22→22
Tmin = 0.849, Tmax = 0.977	k = −72→72
54206 measured reflections	l = −15→15

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0258P)2 + 6.6616P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
6726 reflections	Δρmax = 0.42 e Å−3
164 parameters	Δρmin = −0.23 e Å−3
1 restraint	Absolute structure: Flack (1983), 3202 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.13 (5)

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
S1	0.10407 (2)	0.241432 (7)	0.34587 (3)	0.01374 (6)
S2	−0.04426 (2)	0.186537 (7)	0.31249 (4)	0.01436 (6)
O1	0.08674 (9)	0.16135 (3)	0.79752 (12)	0.0220 (2)
O2	0.22833 (9)	0.13439 (3)	0.82907 (13)	0.0258 (2)
N1	0.16994 (9)	0.15045 (3)	0.75344 (12)	0.0163 (2)
C1	0.08854 (9)	0.20066 (3)	0.27797 (13)	0.01231 (19)
C2	0.11450 (10)	0.19792 (3)	0.11508 (14)	0.0159 (2)
H2A	0.0911	0.1775	0.0791	0.019*
H2B	0.0776	0.2143	0.0618	0.019*
C3	0.23059 (10)	0.20125 (3)	0.08744 (15)	0.0167 (2)
H3A	0.2552	0.2212	0.1269	0.020*
H3B	0.2440	0.2011	−0.0165	0.020*
C4	0.28806 (11)	0.17388 (3)	0.15959 (15)	0.0167 (2)
H4A	0.2745	0.1546	0.1055	0.020*
H4B	0.3622	0.1779	0.1556	0.020*
C5	0.25624 (9)	0.16909 (3)	0.31606 (15)	0.0139 (2)
C6	0.32137 (11)	0.15154 (3)	0.40812 (16)	0.0173 (2)
H6A	0.3840	0.1439	0.3719	0.021*
C7	0.29507 (11)	0.14526 (3)	0.55123 (16)	0.0169 (2)
H7A	0.3388	0.1335	0.6112	0.020*
C8	0.20103 (10)	0.15708 (3)	0.60257 (14)	0.0140 (2)
C9	0.13528 (10)	0.17506 (3)	0.51660 (14)	0.0132 (2)
H9A	0.0739	0.1831	0.5550	0.016*
C10	0.16192 (10)	0.18097 (3)	0.37155 (13)	0.0127 (2)
C11	−0.11830 (10)	0.21555 (3)	0.20993 (15)	0.0160 (2)
H11A	−0.0973	0.2145	0.1086	0.019*
H11B	−0.1913	0.2100	0.2147	0.019*
C12	−0.10538 (11)	0.24943 (3)	0.26325 (16)	0.0176 (2)
H12A	−0.1238	0.2503	0.3656	0.021*
H12B	−0.1535	0.2629	0.2107	0.021*
C13	0.00429 (10)	0.26252 (3)	0.24439 (15)	0.0164 (2)
H13A	0.0046	0.2845	0.2747	0.020*
H13B	0.0220	0.2619	0.1418	0.020*

	U11	U22	U33	U12	U13	U23
S1	0.01297 (12)	0.01371 (11)	0.01454 (13)	0.00002 (10)	−0.00051 (10)	−0.00104 (10)
S2	0.01150 (11)	0.01563 (11)	0.01593 (13)	−0.00058 (10)	−0.00027 (10)	0.00191 (10)
O1	0.0251 (5)	0.0258 (5)	0.0152 (4)	0.0057 (4)	0.0027 (4)	−0.0002 (4)
O2	0.0277 (5)	0.0308 (5)	0.0188 (5)	0.0073 (4)	−0.0041 (4)	0.0086 (4)
N1	0.0198 (5)	0.0157 (4)	0.0135 (5)	0.0000 (4)	−0.0024 (4)	0.0006 (4)
C1	0.0110 (5)	0.0143 (4)	0.0117 (5)	−0.0003 (4)	0.0009 (4)	−0.0003 (4)
C2	0.0159 (5)	0.0197 (5)	0.0121 (5)	0.0014 (4)	0.0012 (4)	−0.0010 (4)
C3	0.0171 (5)	0.0185 (5)	0.0146 (5)	0.0009 (4)	0.0045 (4)	0.0010 (4)
C4	0.0154 (5)	0.0187 (5)	0.0159 (5)	0.0023 (4)	0.0047 (4)	0.0002 (4)
C5	0.0123 (5)	0.0135 (4)	0.0158 (5)	−0.0003 (4)	0.0018 (4)	−0.0002 (4)
C6	0.0141 (5)	0.0172 (5)	0.0205 (6)	0.0031 (4)	0.0015 (5)	0.0006 (5)
C7	0.0153 (5)	0.0156 (5)	0.0197 (6)	0.0020 (4)	−0.0024 (4)	0.0013 (4)
C8	0.0158 (5)	0.0137 (4)	0.0124 (5)	−0.0012 (4)	−0.0010 (4)	0.0003 (4)
C9	0.0123 (5)	0.0146 (5)	0.0128 (5)	−0.0001 (4)	−0.0003 (4)	−0.0006 (4)
C10	0.0116 (5)	0.0135 (4)	0.0129 (5)	−0.0009 (4)	−0.0002 (4)	−0.0002 (4)
C11	0.0129 (5)	0.0179 (5)	0.0173 (6)	0.0011 (4)	−0.0022 (4)	0.0010 (4)
C12	0.0158 (6)	0.0164 (5)	0.0207 (6)	0.0033 (4)	−0.0006 (5)	−0.0002 (4)
C13	0.0152 (5)	0.0152 (5)	0.0187 (6)	0.0019 (4)	−0.0006 (4)	0.0013 (4)

S1—C13	1.8192 (13)	C5—C6	1.4022 (18)
S1—C1	1.8421 (12)	C5—C10	1.4086 (17)
S2—C11	1.8153 (13)	C6—C7	1.383 (2)
S2—C1	1.8375 (12)	C6—H6A	0.9300
O1—N1	1.2337 (16)	C7—C8	1.3915 (18)
O2—N1	1.2276 (15)	C7—H7A	0.9300
N1—C8	1.4688 (17)	C8—C9	1.3840 (17)
C1—C10	1.5236 (17)	C9—C10	1.3977 (17)
C1—C2	1.5369 (17)	C9—H9A	0.9300
C2—C3	1.5217 (18)	C11—C12	1.5216 (19)
C2—H2A	0.9700	C11—H11A	0.9700
C2—H2B	0.9700	C11—H11B	0.9700
C3—C4	1.5237 (18)	C12—C13	1.5254 (19)
C3—H3A	0.9700	C12—H12A	0.9700
C3—H3B	0.9700	C12—H12B	0.9700
C4—C5	1.5075 (19)	C13—H13A	0.9700
C4—H4A	0.9700	C13—H13B	0.9700
C4—H4B	0.9700
C13—S1—C1	101.98 (6)	C7—C6—H6A	119.1
C11—S2—C1	100.34 (6)	C5—C6—H6A	119.1
O2—N1—O1	123.49 (12)	C6—C7—C8	117.77 (12)
O2—N1—C8	118.18 (11)	C6—C7—H7A	121.1
O1—N1—C8	118.33 (11)	C8—C7—H7A	121.1
C10—C1—C2	111.90 (10)	C9—C8—C7	122.36 (12)
C10—C1—S2	107.56 (8)	C9—C8—N1	118.43 (11)
C2—C1—S2	110.21 (9)	C7—C8—N1	119.20 (11)
C10—C1—S1	104.60 (8)	C8—C9—C10	119.44 (11)
C2—C1—S1	112.11 (8)	C8—C9—H9A	120.3
S2—C1—S1	110.24 (6)	C10—C9—H9A	120.3
C3—C2—C1	111.63 (11)	C9—C10—C5	119.50 (11)
C3—C2—H2A	109.3	C9—C10—C1	118.87 (11)
C1—C2—H2A	109.3	C5—C10—C1	121.62 (11)
C3—C2—H2B	109.3	C12—C11—S2	114.24 (9)
C1—C2—H2B	109.3	C12—C11—H11A	108.7
H2A—C2—H2B	108.0	S2—C11—H11A	108.7
C2—C3—C4	109.49 (11)	C12—C11—H11B	108.7
C2—C3—H3A	109.8	S2—C11—H11B	108.7
C4—C3—H3A	109.8	H11A—C11—H11B	107.6
C2—C3—H3B	109.8	C11—C12—C13	113.91 (11)
C4—C3—H3B	109.8	C11—C12—H12A	108.8
H3A—C3—H3B	108.2	C13—C12—H12A	108.8
C5—C4—C3	112.60 (11)	C11—C12—H12B	108.8
C5—C4—H4A	109.1	C13—C12—H12B	108.8
C3—C4—H4A	109.1	H12A—C12—H12B	107.7
C5—C4—H4B	109.1	C12—C13—S1	114.67 (9)
C3—C4—H4B	109.1	C12—C13—H13A	108.6
H4A—C4—H4B	107.8	S1—C13—H13A	108.6
C6—C5—C10	119.02 (12)	C12—C13—H13B	108.6
C6—C5—C4	118.89 (11)	S1—C13—H13B	108.6
C10—C5—C4	122.07 (11)	H13A—C13—H13B	107.6
C7—C6—C5	121.88 (12)
C11—S2—C1—C10	173.57 (8)	O2—N1—C8—C7	−0.47 (18)
C11—S2—C1—C2	−64.20 (9)	O1—N1—C8—C7	179.39 (12)
C11—S2—C1—S1	60.08 (7)	C7—C8—C9—C10	1.89 (18)
C13—S1—C1—C10	−173.77 (8)	N1—C8—C9—C10	−178.31 (11)
C13—S1—C1—C2	64.78 (10)	C8—C9—C10—C5	−1.31 (17)
C13—S1—C1—S2	−58.40 (8)	C8—C9—C10—C1	179.70 (11)
C10—C1—C2—C3	−45.80 (14)	C6—C5—C10—C9	0.02 (17)
S2—C1—C2—C3	−165.44 (8)	C4—C5—C10—C9	178.31 (11)
S1—C1—C2—C3	71.36 (12)	C6—C5—C10—C1	178.98 (11)
C1—C2—C3—C4	64.05 (14)	C4—C5—C10—C1	−2.73 (18)
C2—C3—C4—C5	−49.41 (15)	C2—C1—C10—C9	−165.62 (11)
C3—C4—C5—C6	−161.70 (12)	S2—C1—C10—C9	−44.44 (13)
C3—C4—C5—C10	20.01 (17)	S1—C1—C10—C9	72.78 (12)
C10—C5—C6—C7	0.79 (19)	C2—C1—C10—C5	15.41 (16)
C4—C5—C6—C7	−177.56 (12)	S2—C1—C10—C5	136.59 (10)
C5—C6—C7—C8	−0.27 (19)	S1—C1—C10—C5	−106.18 (11)
C6—C7—C8—C9	−1.09 (19)	C1—S2—C11—C12	−61.71 (11)
C6—C7—C8—N1	179.11 (11)	S2—C11—C12—C13	65.29 (14)
O2—N1—C8—C9	179.72 (12)	C11—C12—C13—S1	−62.18 (14)
O1—N1—C8—C9	−0.42 (17)	C1—S1—C13—C12	56.76 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1i	0.97	2.58	3.4565 (18)	151
C7—H7A···Cg1ii	0.93	2.82	3.7164 (15)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1i	0.97	2.58	3.4565 (18)	151
C7—H7A⋯Cg1ii	0.93	2.82	3.7164 (15)	162

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C5–C10 benzene ring.