Crystal structure of 2-(3-nitro-phen-yl)-1,3-di-thiane.

In the title compound, C10H11NO2S2, the 1,3-di-thiane ring has a chair conformation with the 1,4-disposed C atoms being above and below the remaining four atoms. The nitro-benzene substituent occupies an equatorial position and forms a dihedral angle of 88.28 (5)° with the least-squares plane through the 1,3-di-thiane ring. The nitro group is twisted out of the plane of the benzene ring to which it is connected, forming a dihedral angle of 10.12 (3)°. In the crystal, mol-ecules aggregate into supra-molecular zigzag chains (glide symmetry along the c axis) via nitro-benzene N-O⋯π [N-O⋯Cg(benzene) = 3.4279 (18) Å and angle at O = 93.95 (11)°] inter-actions. The chains pack with no specific inter-molecular inter-actions between them.

Related literature

For background to substituted 1,3-di­thia­nes, see: Ballesteros et al. (2005 ▸). For nitro–aryl N—O⋯π inter­actions, see: Huang et al. (2008 ▸). For the structure of the closely related 3-bromo-substituted compound, see: Zukerman-Schpector et al. (2015 ▸).

Experimental

Crystal data

C10H11NO2S2

M = 241.32

Monoclinic,

a = 10.8547 (2) Å

b = 13.2655 (3) Å

c = 8.0891 (2) Å

β = 109.087 (1)°

V = 1100.74 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 293 K

0.49 × 0.46 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T min = 0.687, T max = 0.745

7241 measured reflections

2035 independent reflections

1799 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.089

S = 1.06

2035 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SIR2014 (Burla et al., 2015 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and DIAMOND (Brandenburg, 2006 ▸); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015002844/hg5430sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015002844/hg5430Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015002844/hg5430Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015002844/hg5430fig1.tif

The mol­ecular structure of the title compound showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.

Click here for additional data file.

c . DOI: 10.1107/S2056989015002844/hg5430fig2.tif

Upper view: detail of the nitro-N—O⋯π(benzene) inter­action. Lower view: the zigzag supra­molecular chain along the c axis (glide symmetry) mediated by nitro-N—O⋯π(benzene) inter­actions shown as purple dashed lines.

Click here for additional data file.

b . DOI: 10.1107/S2056989015002844/hg5430fig3.tif

A view in projection down the b axis of the unit-cell contents. The nitro-N—O⋯π(benzene) inter­actions are shown as purple dashed lines.

CCDC reference: 1048518

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H11NO2S2	F(000) = 504
Mr = 241.32	Dx = 1.456 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.8547 (2) Å	Cell parameters from 4425 reflections
b = 13.2655 (3) Å	θ = 2.5–25.4°
c = 8.0891 (2) Å	µ = 0.46 mm−1
β = 109.087 (1)°	T = 293 K
V = 1100.74 (4) Å3	Slab, colourless
Z = 4	0.49 × 0.46 × 0.21 mm

Bruker APEXII CCD diffractometer	1799 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.020
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 25.4°, θmin = 2.0°
Tmin = 0.687, Tmax = 0.745	h = −13→12
7241 measured reflections	k = −16→16
2035 independent reflections	l = −8→9

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031	w = 1/[σ2(Fo2) + (0.0444P)2 + 0.3472P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.089	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.29 e Å−3
2035 reflections	Δρmin = −0.24 e Å−3
137 parameters	Extinction correction: SHELXL2014 (Sheldrick 2014, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0192 (17)

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.

	x	y	z	Uiso*/Ueq
S1	0.93087 (4)	0.75719 (3)	0.69969 (5)	0.04460 (16)
S2	0.93019 (4)	0.98623 (3)	0.69835 (6)	0.04646 (16)
O1	0.54267 (18)	0.88063 (13)	0.15045 (19)	0.0830 (5)
O2	0.35484 (16)	0.85594 (14)	0.1765 (2)	0.0917 (6)
N1	0.47188 (18)	0.86855 (11)	0.2380 (2)	0.0608 (5)
C1	0.86732 (14)	0.87164 (10)	0.76325 (19)	0.0340 (3)
H1	0.8887	0.8719	0.8907	0.041*
C2	1.10282 (17)	0.96790 (14)	0.8068 (2)	0.0511 (4)
H2A	1.1494	1.0248	0.7804	0.061*
H2B	1.1198	0.9673	0.9322	0.061*
C3	1.15622 (17)	0.87200 (13)	0.7556 (2)	0.0519 (5)
H3A	1.1364	0.8713	0.6297	0.062*
H3B	1.2503	0.8720	0.8085	0.062*
C4	1.10278 (17)	0.77709 (14)	0.8096 (2)	0.0503 (4)
H4A	1.1185	0.7796	0.9347	0.060*
H4B	1.1503	0.7198	0.7868	0.060*
C5	0.72187 (15)	0.87186 (10)	0.6807 (2)	0.0353 (3)
C6	0.66533 (16)	0.86907 (11)	0.4999 (2)	0.0403 (4)
H6	0.7169	0.8669	0.4280	0.048*
C7	0.53161 (17)	0.86960 (11)	0.4295 (2)	0.0454 (4)
C8	0.45093 (17)	0.87258 (13)	0.5303 (3)	0.0538 (5)
H8	0.3607	0.8722	0.4790	0.065*
C9	0.50821 (18)	0.87617 (13)	0.7092 (3)	0.0539 (5)
H9	0.4561	0.8788	0.7803	0.065*
C10	0.64180 (17)	0.87591 (11)	0.7842 (2)	0.0441 (4)
H10	0.6789	0.8785	0.9053	0.053*

	U11	U22	U33	U12	U13	U23
S1	0.0499 (3)	0.0379 (2)	0.0436 (3)	0.00382 (16)	0.01201 (19)	−0.00589 (15)
S2	0.0441 (3)	0.0374 (3)	0.0589 (3)	−0.00061 (16)	0.0181 (2)	0.00780 (17)
O1	0.0889 (12)	0.1119 (14)	0.0382 (8)	0.0027 (9)	0.0071 (8)	0.0037 (7)
O2	0.0563 (9)	0.1212 (14)	0.0696 (10)	0.0056 (9)	−0.0178 (8)	−0.0135 (9)
N1	0.0629 (11)	0.0593 (10)	0.0454 (9)	0.0066 (7)	−0.0023 (8)	−0.0033 (7)
C1	0.0388 (8)	0.0344 (8)	0.0294 (7)	−0.0002 (6)	0.0119 (6)	−0.0002 (5)
C2	0.0416 (9)	0.0581 (11)	0.0532 (10)	−0.0114 (8)	0.0152 (8)	−0.0059 (8)
C3	0.0368 (8)	0.0729 (13)	0.0477 (10)	0.0044 (8)	0.0161 (7)	0.0004 (8)
C4	0.0467 (9)	0.0580 (11)	0.0433 (9)	0.0163 (8)	0.0107 (7)	0.0050 (7)
C5	0.0378 (8)	0.0338 (8)	0.0351 (8)	−0.0015 (6)	0.0128 (6)	0.0003 (5)
C6	0.0426 (9)	0.0438 (9)	0.0355 (8)	0.0009 (6)	0.0140 (7)	0.0009 (6)
C7	0.0456 (9)	0.0417 (9)	0.0408 (9)	−0.0002 (7)	0.0032 (7)	−0.0022 (6)
C8	0.0353 (9)	0.0542 (11)	0.0689 (12)	−0.0036 (7)	0.0131 (8)	−0.0020 (8)
C9	0.0462 (10)	0.0625 (12)	0.0608 (11)	−0.0065 (8)	0.0282 (9)	−0.0023 (8)
C10	0.0472 (9)	0.0490 (9)	0.0403 (9)	−0.0052 (7)	0.0201 (7)	−0.0006 (7)

S1—C4	1.8048 (18)	C3—H3B	0.9700
S1—C1	1.8102 (14)	C4—H4A	0.9700
S2—C2	1.8069 (18)	C4—H4B	0.9700
S2—C1	1.8128 (14)	C5—C6	1.389 (2)
O1—N1	1.214 (2)	C5—C10	1.391 (2)
O2—N1	1.215 (2)	C6—C7	1.375 (2)
N1—C7	1.471 (2)	C6—H6	0.9300
C1—C5	1.500 (2)	C7—C8	1.379 (3)
C1—H1	0.9800	C8—C9	1.377 (3)
C2—C3	1.511 (2)	C8—H8	0.9300
C2—H2A	0.9700	C9—C10	1.377 (3)
C2—H2B	0.9700	C9—H9	0.9300
C3—C4	1.509 (3)	C10—H10	0.9300
C3—H3A	0.9700
C4—S1—C1	99.55 (8)	C3—C4—H4A	108.7
C2—S2—C1	100.11 (8)	S1—C4—H4A	108.7
O1—N1—O2	123.77 (18)	C3—C4—H4B	108.7
O1—N1—C7	117.90 (17)	S1—C4—H4B	108.7
O2—N1—C7	118.32 (19)	H4A—C4—H4B	107.6
C5—C1—S1	108.59 (10)	C6—C5—C10	119.13 (15)
C5—C1—S2	108.10 (10)	C6—C5—C1	120.46 (13)
S1—C1—S2	113.99 (8)	C10—C5—C1	120.41 (14)
C5—C1—H1	108.7	C7—C6—C5	118.65 (15)
S1—C1—H1	108.7	C7—C6—H6	120.7
S2—C1—H1	108.7	C5—C6—H6	120.7
C3—C2—S2	114.22 (12)	C6—C7—C8	122.93 (16)
C3—C2—H2A	108.7	C6—C7—N1	118.60 (16)
S2—C2—H2A	108.7	C8—C7—N1	118.46 (16)
C3—C2—H2B	108.7	C9—C8—C7	117.84 (16)
S2—C2—H2B	108.7	C9—C8—H8	121.1
H2A—C2—H2B	107.6	C7—C8—H8	121.1
C4—C3—C2	113.89 (15)	C10—C9—C8	120.77 (16)
C4—C3—H3A	108.8	C10—C9—H9	119.6
C2—C3—H3A	108.8	C8—C9—H9	119.6
C4—C3—H3B	108.8	C9—C10—C5	120.67 (16)
C2—C3—H3B	108.8	C9—C10—H10	119.7
H3A—C3—H3B	107.7	C5—C10—H10	119.7
C3—C4—S1	114.37 (12)
C4—S1—C1—C5	178.82 (10)	C1—C5—C6—C7	−179.86 (13)
C4—S1—C1—S2	58.27 (10)	C5—C6—C7—C8	−0.1 (2)
C2—S2—C1—C5	−178.78 (10)	C5—C6—C7—N1	178.88 (13)
C2—S2—C1—S1	−57.95 (10)	O1—N1—C7—C6	−9.5 (2)
C1—S2—C2—C3	57.35 (14)	O2—N1—C7—C6	170.67 (16)
S2—C2—C3—C4	−65.25 (19)	O1—N1—C7—C8	169.54 (17)
C2—C3—C4—S1	66.18 (19)	O2—N1—C7—C8	−10.3 (2)
C1—S1—C4—C3	−58.63 (14)	C6—C7—C8—C9	0.7 (2)
S1—C1—C5—C6	−60.31 (15)	N1—C7—C8—C9	−178.35 (15)
S2—C1—C5—C6	63.82 (15)	C7—C8—C9—C10	−0.5 (3)
S1—C1—C5—C10	120.35 (13)	C8—C9—C10—C5	−0.1 (2)
S2—C1—C5—C10	−115.51 (13)	C6—C5—C10—C9	0.6 (2)
C10—C5—C6—C7	−0.5 (2)	C1—C5—C10—C9	179.98 (14)