2-(Pyrene-1-yl)-1,3-dithiane.

In the title compound, C(20)H(16)S(2), the pyrene ring is planar [maximum deviation 0.0144 (15) Å] and the dithiane ring adopts a chair conformation. The crystal packing is stabilized by C-H⋯π inter-actions. An intra-molecular C-H⋯S hydrogen bond generates an S(5) ring motif.

Related literature

For thio­nation reactions, see: Goswami & Maity (2008 ▶); Goswami et al. (2009 ▶); Fun et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H16S2

M = 320.45

Orthorhombic,

a = 7.1424 (1) Å

b = 8.6016 (1) Å

c = 24.5049 (2) Å

V = 1505.48 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 100 K

0.36 × 0.17 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.885, T max = 0.962

29712 measured reflections

6424 independent reflections

5501 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.092

S = 1.05

6424 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 2662 Friedel pairs

Flack parameter: 0.03 (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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010320/at2745sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010320/at2745Isup2.hkl

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

C20H16S2	F(000) = 672
Mr = 320.45	Dx = 1.414 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9340 reflections
a = 7.1424 (1) Å	θ = 2.5–33.7°
b = 8.6016 (1) Å	µ = 0.35 mm−1
c = 24.5049 (2) Å	T = 100 K
V = 1505.48 (3) Å3	Block, colourless
Z = 4	0.36 × 0.17 × 0.11 mm

Bruker SMART APEXII CCD area-detector diffractometer	6424 independent reflections
Radiation source: fine-focus sealed tube	5501 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 35.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.885, Tmax = 0.962	k = −13→13
29712 measured reflections	l = −39→39

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0461P)2 + 0.0807P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.004
6424 reflections	Δρmax = 0.48 e Å−3
199 parameters	Δρmin = −0.27 e Å−3
0 restraints	Absolute structure: Flack (1983), 2662 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (5)

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
S1	0.38288 (5)	0.10233 (4)	0.977454 (13)	0.01668 (8)
S2	0.68513 (5)	−0.07534 (4)	1.037145 (12)	0.01665 (8)
C1	0.6709 (2)	−0.12016 (15)	0.77433 (5)	0.0134 (2)
C2	0.73272 (19)	−0.07300 (16)	0.82744 (5)	0.0131 (2)
C3	0.9112 (2)	−0.00108 (16)	0.83308 (5)	0.0140 (2)
C4	1.0265 (2)	0.01927 (17)	0.78565 (6)	0.0173 (3)
H4A	1.1443	0.0640	0.7894	0.021*
C5	0.9675 (2)	−0.02513 (17)	0.73559 (6)	0.0177 (3)
H5A	1.0456	−0.0107	0.7057	0.021*
C6	0.7869 (2)	−0.09392 (16)	0.72787 (5)	0.0156 (3)
C7	0.7187 (2)	−0.13545 (17)	0.67611 (5)	0.0180 (3)
H7A	0.7932	−0.1193	0.6455	0.022*
C8	0.5425 (2)	−0.19998 (17)	0.66994 (6)	0.0190 (3)
H8A	0.4998	−0.2264	0.6353	0.023*
C9	0.4287 (2)	−0.22556 (16)	0.71502 (5)	0.0180 (3)
H9A	0.3102	−0.2682	0.7103	0.022*
C10	0.4912 (2)	−0.18750 (16)	0.76761 (5)	0.0145 (2)
C11	0.3773 (2)	−0.21097 (16)	0.81490 (5)	0.0162 (3)
H11A	0.2612	−0.2588	0.8110	0.019*
C12	0.4341 (2)	−0.16537 (17)	0.86520 (5)	0.0155 (3)
H12A	0.3555	−0.1810	0.8950	0.019*
C13	0.61341 (19)	−0.09331 (15)	0.87345 (5)	0.0129 (2)
C14	0.6739 (2)	−0.03780 (15)	0.92506 (5)	0.0139 (2)
C15	0.8468 (2)	0.03716 (16)	0.92932 (5)	0.0159 (3)
H15A	0.8838	0.0771	0.9629	0.019*
C16	0.9649 (2)	0.05354 (16)	0.88468 (5)	0.0164 (3)
H16A	1.0808	0.1012	0.8890	0.020*
C17	0.54924 (19)	−0.05773 (15)	0.97455 (5)	0.0142 (2)
H17A	0.4780	−0.1542	0.9698	0.017*
C18	0.2364 (2)	0.03068 (18)	1.03263 (5)	0.0201 (3)
H18A	0.1366	0.1049	1.0391	0.024*
H18B	0.1791	−0.0663	1.0213	0.024*
C19	0.3411 (2)	0.00340 (18)	1.08623 (5)	0.0184 (3)
H19A	0.3993	0.1001	1.0975	0.022*
H19B	0.2516	−0.0259	1.1142	0.022*
C20	0.4911 (2)	−0.12196 (17)	1.08241 (5)	0.0174 (3)
H20A	0.4331	−0.2175	1.0699	0.021*
H20B	0.5404	−0.1410	1.1187	0.021*

	U11	U22	U33	U12	U13	U23
S1	0.01679 (16)	0.01854 (16)	0.01470 (14)	0.00372 (13)	−0.00236 (11)	0.00034 (12)
S2	0.01684 (15)	0.02099 (17)	0.01214 (13)	0.00328 (14)	−0.00233 (11)	0.00104 (12)
C1	0.0165 (6)	0.0116 (5)	0.0120 (5)	0.0012 (5)	−0.0008 (4)	−0.0008 (4)
C2	0.0142 (6)	0.0121 (6)	0.0131 (5)	0.0004 (5)	−0.0012 (4)	0.0010 (4)
C3	0.0131 (6)	0.0128 (6)	0.0160 (5)	0.0010 (5)	−0.0021 (5)	0.0015 (4)
C4	0.0148 (7)	0.0169 (6)	0.0203 (6)	0.0002 (5)	0.0011 (5)	0.0020 (5)
C5	0.0171 (7)	0.0185 (7)	0.0177 (6)	0.0019 (5)	0.0038 (5)	0.0024 (5)
C6	0.0174 (6)	0.0145 (6)	0.0148 (5)	0.0021 (5)	0.0004 (4)	0.0012 (5)
C7	0.0236 (7)	0.0177 (7)	0.0128 (6)	0.0025 (5)	0.0003 (5)	0.0001 (5)
C8	0.0256 (7)	0.0182 (7)	0.0133 (6)	0.0021 (6)	−0.0034 (5)	−0.0019 (5)
C9	0.0216 (7)	0.0158 (6)	0.0166 (6)	−0.0008 (5)	−0.0035 (5)	−0.0020 (5)
C10	0.0178 (6)	0.0124 (6)	0.0134 (5)	0.0001 (5)	−0.0017 (5)	−0.0019 (4)
C11	0.0159 (6)	0.0169 (6)	0.0159 (6)	−0.0033 (5)	−0.0015 (5)	−0.0010 (5)
C12	0.0159 (6)	0.0164 (6)	0.0141 (5)	−0.0028 (5)	0.0002 (5)	0.0007 (5)
C13	0.0153 (6)	0.0103 (5)	0.0130 (5)	0.0004 (5)	−0.0015 (4)	0.0001 (4)
C14	0.0151 (6)	0.0133 (6)	0.0133 (5)	0.0012 (5)	−0.0021 (5)	0.0003 (4)
C15	0.0181 (7)	0.0157 (6)	0.0138 (5)	−0.0010 (5)	−0.0043 (5)	−0.0001 (5)
C16	0.0147 (6)	0.0160 (6)	0.0186 (6)	−0.0016 (5)	−0.0027 (5)	0.0016 (5)
C17	0.0163 (6)	0.0148 (6)	0.0115 (5)	0.0014 (5)	−0.0024 (4)	−0.0008 (4)
C18	0.0154 (6)	0.0269 (7)	0.0179 (6)	0.0021 (6)	−0.0001 (5)	−0.0018 (5)
C19	0.0212 (7)	0.0212 (7)	0.0128 (5)	0.0008 (6)	0.0005 (5)	−0.0010 (5)
C20	0.0207 (7)	0.0179 (7)	0.0136 (5)	−0.0005 (6)	0.0001 (5)	0.0018 (5)

S1—C18	1.8173 (15)	C9—H9A	0.9300
S1—C17	1.8200 (14)	C10—C11	1.4301 (19)
S2—C20	1.8200 (15)	C11—C12	1.3557 (18)
S2—C17	1.8214 (13)	C11—H11A	0.9300
C1—C10	1.418 (2)	C12—C13	1.4373 (19)
C1—C6	1.4260 (18)	C12—H12A	0.9300
C1—C2	1.4328 (17)	C13—C14	1.4191 (17)
C2—C3	1.4239 (19)	C14—C15	1.397 (2)
C2—C13	1.4242 (17)	C14—C17	1.5144 (18)
C3—C16	1.4024 (18)	C15—C16	1.3884 (19)
C3—C4	1.4349 (19)	C15—H15A	0.9300
C4—C5	1.3521 (19)	C16—H16A	0.9300
C4—H4A	0.9300	C17—H17A	0.9800
C5—C6	1.432 (2)	C18—C19	1.5298 (19)
C5—H5A	0.9300	C18—H18A	0.9700
C6—C7	1.4047 (18)	C18—H18B	0.9700
C7—C8	1.384 (2)	C19—C20	1.523 (2)
C7—H7A	0.9300	C19—H19A	0.9700
C8—C9	1.389 (2)	C19—H19B	0.9700
C8—H8A	0.9300	C20—H20A	0.9700
C9—C10	1.4025 (18)	C20—H20B	0.9700
C18—S1—C17	98.54 (7)	C13—C12—H12A	119.4
C20—S2—C17	97.23 (6)	C14—C13—C2	118.82 (12)
C10—C1—C6	119.86 (11)	C14—C13—C12	122.81 (12)
C10—C1—C2	120.01 (12)	C2—C13—C12	118.34 (11)
C6—C1—C2	120.09 (12)	C15—C14—C13	119.42 (12)
C3—C2—C13	120.81 (11)	C15—C14—C17	120.80 (11)
C3—C2—C1	119.16 (12)	C13—C14—C17	119.77 (12)
C13—C2—C1	120.00 (12)	C16—C15—C14	121.66 (12)
C16—C3—C2	118.55 (12)	C16—C15—H15A	119.2
C16—C3—C4	122.18 (13)	C14—C15—H15A	119.2
C2—C3—C4	119.21 (12)	C15—C16—C3	120.69 (13)
C5—C4—C3	121.43 (14)	C15—C16—H16A	119.7
C5—C4—H4A	119.3	C3—C16—H16A	119.7
C3—C4—H4A	119.3	C14—C17—S1	109.24 (9)
C4—C5—C6	121.17 (13)	C14—C17—S2	111.75 (9)
C4—C5—H5A	119.4	S1—C17—S2	112.20 (7)
C6—C5—H5A	119.4	C14—C17—H17A	107.8
C7—C6—C1	118.64 (13)	S1—C17—H17A	107.8
C7—C6—C5	122.46 (12)	S2—C17—H17A	107.8
C1—C6—C5	118.89 (11)	C19—C18—S1	114.16 (10)
C8—C7—C6	121.05 (13)	C19—C18—H18A	108.7
C8—C7—H7A	119.5	S1—C18—H18A	108.7
C6—C7—H7A	119.5	C19—C18—H18B	108.7
C7—C8—C9	120.58 (13)	S1—C18—H18B	108.7
C7—C8—H8A	119.7	H18A—C18—H18B	107.6
C9—C8—H8A	119.7	C20—C19—C18	113.57 (11)
C8—C9—C10	120.51 (14)	C20—C19—H19A	108.9
C8—C9—H9A	119.7	C18—C19—H19A	108.9
C10—C9—H9A	119.7	C20—C19—H19B	108.9
C9—C10—C1	119.35 (13)	C18—C19—H19B	108.9
C9—C10—C11	122.04 (13)	H19A—C19—H19B	107.7
C1—C10—C11	118.60 (11)	C19—C20—S2	114.65 (10)
C12—C11—C10	121.71 (13)	C19—C20—H20A	108.6
C12—C11—H11A	119.1	S2—C20—H20A	108.6
C10—C11—H11A	119.1	C19—C20—H20B	108.6
C11—C12—C13	121.29 (13)	S2—C20—H20B	108.6
C11—C12—H12A	119.4	H20A—C20—H20B	107.6
C10—C1—C2—C3	−178.01 (12)	C10—C11—C12—C13	−1.0 (2)
C6—C1—C2—C3	−0.47 (19)	C3—C2—C13—C14	1.21 (19)
C10—C1—C2—C13	−0.20 (19)	C1—C2—C13—C14	−176.56 (12)
C6—C1—C2—C13	177.34 (12)	C3—C2—C13—C12	179.43 (12)
C13—C2—C3—C16	−1.84 (19)	C1—C2—C13—C12	1.66 (19)
C1—C2—C3—C16	175.95 (13)	C11—C12—C13—C14	177.07 (13)
C13—C2—C3—C4	−179.16 (13)	C11—C12—C13—C2	−1.1 (2)
C1—C2—C3—C4	−1.37 (19)	C2—C13—C14—C15	0.97 (19)
C16—C3—C4—C5	−175.68 (14)	C12—C13—C14—C15	−177.17 (13)
C2—C3—C4—C5	1.5 (2)	C2—C13—C14—C17	179.86 (12)
C3—C4—C5—C6	0.2 (2)	C12—C13—C14—C17	1.7 (2)
C10—C1—C6—C7	0.25 (19)	C13—C14—C15—C16	−2.6 (2)
C2—C1—C6—C7	−177.30 (13)	C17—C14—C15—C16	178.56 (12)
C10—C1—C6—C5	179.72 (13)	C14—C15—C16—C3	1.9 (2)
C2—C1—C6—C5	2.17 (19)	C2—C3—C16—C15	0.3 (2)
C4—C5—C6—C7	177.38 (14)	C4—C3—C16—C15	177.52 (13)
C4—C5—C6—C1	−2.1 (2)	C15—C14—C17—S1	93.99 (13)
C1—C6—C7—C8	0.3 (2)	C13—C14—C17—S1	−84.88 (13)
C5—C6—C7—C8	−179.18 (13)	C15—C14—C17—S2	−30.77 (16)
C6—C7—C8—C9	−0.2 (2)	C13—C14—C17—S2	150.36 (10)
C7—C8—C9—C10	−0.5 (2)	C18—S1—C17—C14	171.69 (9)
C8—C9—C10—C1	1.0 (2)	C18—S1—C17—S2	−63.82 (9)
C8—C9—C10—C11	179.45 (13)	C20—S2—C17—C14	−172.85 (9)
C6—C1—C10—C9	−0.88 (19)	C20—S2—C17—S1	64.05 (8)
C2—C1—C10—C9	176.67 (13)	C17—S1—C18—C19	59.16 (12)
C6—C1—C10—C11	−179.38 (13)	S1—C18—C19—C20	−63.42 (15)
C2—C1—C10—C11	−1.83 (19)	C18—C19—C20—S2	65.04 (15)
C9—C10—C11—C12	−175.99 (14)	C17—S2—C20—C19	−61.20 (11)
C1—C10—C11—C12	2.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···S2	0.93	2.65	3.0416 (13)	106
C9—H9A···Cg1i	0.93	2.68	3.4196 (15)	137
C4—H4A···Cg2ii	0.93	2.98	3.8073 (16)	149
C20—H20A···Cg3iii	0.97	2.78	3.5339 (15)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯S2	0.93	2.65	3.0416 (13)	106
C9—H9A⋯Cg1i	0.93	2.68	3.4196 (15)	137
C4—H4A⋯Cg2ii	0.93	2.98	3.8073 (16)	149
C20—H20A⋯Cg3iii	0.97	2.78	3.5339 (15)	135

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C1–C6 ring, Cg2 is the centroid of the C1/C6–C10 ring and Cg3 is the centroid of the C2/C3/C13–C16 ring.