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Acta Cryst. (2007). E63, o3957    [ doi:10.1107/S1600536807042432 ]

1-Bromo-8-(ethylsulfanyl)naphthalene

A. L. Fuller, F. R. Knight, A. M. Z. Slawin and J. D. Woollins

Abstract top

There are two molecules in the asymmetric unit of the title compound, C12H11BrS, with similar conformations. Intramolecular Br...S(ethyl) distances are 3.056 (2) and 3.050 (2) Å. The molecules pack into a herringbone array with no significant [pi]-[pi] interactions.

Comment top

As part of a broader study into sterically crowded naphthalene derivatives (Aucott et al., 2004), here we report the structure of the title compound, (I), (Fig. 1), which contains two independent molecules. The intramolecular Br···SEt distances are 3.056 (2) and 3.050 (2) Å. The bromine and sulfur atoms show minor deviations above/below their attached ring planes: S9 = 0.022 (2) Å, S29 = −0.016 (2) Å, Br1 = −0.117 (1) Å and Br21 = −0.018 (1) Å. naphthalene planes

The molecules pack in a herringbone array with no significant π–π interactions. The shortest intermolecular S···S distance is 4.199 (2) Å and there is a weak intermolecular C—H···Br interaction [for C22–H22A···Br1: H···Br = 3.025 Å, C—H···Br = 167°].

Related literature top

For background, see: Aucott et al. (2004). For synthesis, see Oki & Yamada (1988).

Experimental top

The title compound was prepared as described previously (Oki & Yamada, 1988) and colourless blocks of (I) were recystallized from n-hexane.

Refinement top

All the H atoms were geometrically placed (C—H = 0.95–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Computing details top

Data collection: SCXmini (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku, 2006); software used to prepare material for publication: CrystalStructure (Rigaku, 2006).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level (arbitrary spheres for the H atoms).
1-Bromo-8-(ethylsulfanyl)naphthalene top
Crystal data top
C12H11BrSF000 = 1072
Mr = 267.18Dx = 1.688 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3763 reflections
a = 11.632 (4) Åθ = 1.6–25.2º
b = 12.260 (4) ŵ = 4.06 mm−1
c = 14.748 (4) ÅT = 125 (2) K
β = 91.692 (9)ºBlock, colourless
V = 2102.2 (11) Å30.25 × 0.20 × 0.20 mm
Z = 8
Data collection top
Rigaku SCXmini CCD
diffractometer		3543 independent reflections
Radiation source: fine-focus sealed tube2316 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.079
T = 125(2) Kθmax = 25.0º
ω scansθmin = 7.8º
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = 0→13
Tmin = 0.396, Tmax = 0.452k = −14→14
6713 measured reflectionsl = −17→17
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.106  w = 1/[σ2(Fo2) + (0.044P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
3543 reflectionsΔρmax = 0.46 e Å−3
254 parametersΔρmin = −0.47 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C12H11BrSV = 2102.2 (11) Å3
Mr = 267.18Z = 8
Monoclinic, P21/cMo Kα
a = 11.632 (4) ŵ = 4.06 mm−1
b = 12.260 (4) ÅT = 125 (2) K
c = 14.748 (4) Å0.25 × 0.20 × 0.20 mm
β = 91.692 (9)º
Data collection top
Rigaku SCXmini CCD
diffractometer		3543 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		2316 reflections with I > 2σ(I)
Tmin = 0.396, Tmax = 0.452Rint = 0.079
6713 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.053254 parameters
wR(F2) = 0.106H-atom parameters constrained
S = 0.99Δρmax = 0.46 e Å−3
3543 reflectionsΔρmin = −0.47 e Å−3
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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.07289 (6)0.47998 (5)0.38936 (4)0.02453 (19)
C10.0346 (5)0.4500 (5)0.2657 (4)0.0190 (14)
C2−0.0539 (6)0.5134 (6)0.2332 (4)0.0275 (15)
H2A−0.08500.56820.27090.033*
C3−0.0995 (6)0.4985 (6)0.1450 (5)0.0291 (17)
H3A−0.16200.54180.12290.035*
C4−0.0529 (5)0.4216 (6)0.0921 (4)0.0229 (15)
H4A−0.08370.41110.03230.027*
C50.0391 (5)0.3568 (5)0.1223 (4)0.0201 (14)
C60.0854 (5)0.2758 (5)0.0626 (4)0.0191 (14)
H6A0.05150.26560.00380.023*
C70.1740 (6)0.2160 (5)0.0887 (4)0.0195 (14)
H7A0.20430.16420.04780.023*
C80.2248 (6)0.2269 (5)0.1753 (4)0.0222 (14)
H8A0.28870.18210.19170.027*
C90.1853 (5)0.3003 (5)0.2373 (4)0.0172 (13)
C100.0884 (5)0.3688 (5)0.2130 (3)0.0138 (12)
S90.25526 (14)0.31016 (13)0.34520 (10)0.0209 (4)
C110.3730 (6)0.2139 (5)0.3396 (4)0.0222 (14)
H11A0.34340.13850.33320.027*
H11B0.42150.23040.28720.027*
C120.4421 (6)0.2271 (5)0.4288 (4)0.0253 (15)
H12A0.50730.17660.42980.038*
H12B0.39260.21110.47980.038*
H12C0.47050.30220.43390.038*
Br210.33155 (6)0.74894 (6)0.39260 (4)0.0266 (2)
C210.2805 (5)0.7861 (5)0.2732 (4)0.0184 (14)
C220.1837 (6)0.7288 (5)0.2451 (4)0.0254 (15)
H22A0.14940.67810.28480.031*
C230.1365 (6)0.7454 (6)0.1584 (4)0.0270 (15)
H23A0.07080.70480.13870.032*
C240.1827 (6)0.8179 (5)0.1030 (4)0.0236 (15)
H24A0.14930.82790.04400.028*
C250.2803 (5)0.8805 (5)0.1297 (4)0.0209 (14)
C260.3233 (6)0.9574 (5)0.0688 (4)0.0220 (15)
H26A0.28740.96590.01060.026*
C270.4170 (6)1.0206 (6)0.0931 (4)0.0261 (15)
H27A0.44461.07420.05250.031*
C280.4710 (6)1.0053 (5)0.1774 (4)0.0255 (15)
H28A0.53681.04810.19290.031*
C290.4327 (5)0.9304 (5)0.2397 (4)0.0186 (13)
C300.3345 (5)0.8662 (5)0.2180 (4)0.0164 (13)
S290.50989 (14)0.92059 (13)0.34520 (10)0.0221 (4)
C310.6292 (5)1.0142 (5)0.3351 (4)0.0227 (14)
H31A0.67780.99270.28410.027*
H31B0.60081.08930.32430.027*
C320.6973 (6)1.0079 (6)0.4242 (5)0.0309 (17)
H32A0.76351.05710.42210.046*
H32B0.72430.93300.43410.046*
H32C0.64811.02950.47390.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0280 (4)0.0259 (3)0.0197 (3)0.0037 (3)−0.0004 (3)−0.0061 (3)
C10.021 (3)0.018 (3)0.018 (3)0.001 (3)0.003 (3)−0.002 (2)
C20.031 (4)0.025 (4)0.027 (3)0.003 (3)0.006 (3)0.001 (3)
C30.019 (3)0.045 (5)0.024 (3)0.010 (3)−0.001 (3)0.015 (3)
C40.013 (3)0.039 (4)0.016 (3)−0.004 (3)−0.002 (3)0.004 (3)
C50.021 (3)0.026 (3)0.014 (3)−0.009 (3)0.002 (3)0.001 (3)
C60.015 (3)0.032 (4)0.010 (3)−0.010 (3)−0.005 (2)−0.001 (3)
C70.026 (4)0.019 (3)0.013 (3)−0.009 (3)0.003 (3)−0.006 (2)
C80.025 (4)0.018 (3)0.024 (3)0.001 (3)0.003 (3)0.004 (3)
C90.018 (3)0.014 (3)0.019 (3)−0.004 (3)−0.006 (3)0.005 (3)
C100.013 (3)0.022 (3)0.006 (3)−0.009 (3)−0.001 (2)0.003 (2)
S90.0258 (9)0.0229 (8)0.0140 (7)0.0070 (7)−0.0020 (7)−0.0021 (6)
C110.025 (4)0.022 (3)0.019 (3)0.004 (3)−0.003 (3)−0.001 (3)
C120.025 (4)0.026 (4)0.024 (3)0.008 (3)−0.008 (3)0.002 (3)
Br210.0342 (4)0.0279 (4)0.0174 (3)−0.0057 (3)−0.0042 (3)0.0074 (3)
C210.020 (3)0.021 (3)0.014 (3)0.005 (3)−0.001 (3)−0.005 (2)
C220.025 (4)0.024 (4)0.028 (3)−0.003 (3)0.006 (3)−0.003 (3)
C230.021 (4)0.034 (4)0.026 (4)0.003 (3)−0.004 (3)−0.010 (3)
C240.021 (4)0.034 (4)0.015 (3)0.012 (3)−0.004 (3)−0.004 (3)
C250.021 (3)0.028 (4)0.013 (3)0.016 (3)0.000 (3)−0.006 (3)
C260.027 (4)0.027 (4)0.012 (3)0.012 (3)0.002 (3)0.002 (3)
C270.035 (4)0.024 (3)0.020 (3)0.007 (3)0.014 (3)0.012 (3)
C280.032 (4)0.015 (3)0.029 (3)−0.004 (3)0.005 (3)−0.003 (3)
C290.019 (3)0.021 (3)0.016 (3)0.008 (3)0.001 (3)−0.001 (3)
C300.023 (3)0.013 (3)0.014 (3)0.008 (3)0.001 (2)−0.005 (2)
S290.0246 (9)0.0236 (9)0.0179 (8)−0.0030 (7)−0.0032 (7)0.0010 (7)
C310.021 (3)0.022 (3)0.025 (3)−0.001 (3)−0.003 (3)−0.002 (3)
C320.031 (4)0.027 (4)0.034 (4)−0.008 (3)−0.007 (3)−0.004 (3)
Geometric parameters (Å, °) top
Br1—C11.901 (6)Br21—C211.897 (6)
C1—C21.365 (9)C21—C221.381 (9)
C1—C101.419 (8)C21—C301.433 (9)
C2—C31.403 (10)C22—C231.391 (9)
C2—H2A0.9500C22—H22A0.9500
C3—C41.348 (9)C23—C241.331 (10)
C3—H3A0.9500C23—H23A0.9500
C4—C51.395 (9)C24—C251.417 (10)
C4—H4A0.9500C24—H24A0.9500
C5—C61.443 (9)C25—C261.404 (9)
C5—C101.446 (8)C25—C301.441 (8)
C6—C71.312 (9)C26—C271.376 (10)
C6—H6A0.9500C26—H26A0.9500
C7—C81.398 (8)C27—C281.388 (10)
C7—H7A0.9500C27—H27A0.9500
C8—C91.371 (9)C28—C291.382 (9)
C8—H8A0.9500C28—H28A0.9500
C9—C101.443 (8)C29—C301.415 (9)
C9—S91.770 (6)C29—S291.778 (6)
S9—C111.811 (7)S29—C311.810 (7)
C11—C121.530 (9)C31—C321.516 (9)
C11—H11A0.9900C31—H31A0.9900
C11—H11B0.9900C31—H31B0.9900
C12—H12A0.9800C32—H32A0.9800
C12—H12B0.9800C32—H32B0.9800
C12—H12C0.9800C32—H32C0.9800
C2—C1—C10123.2 (6)C22—C21—C30123.1 (5)
C2—C1—Br1112.3 (5)C22—C21—Br21112.8 (5)
C10—C1—Br1124.5 (4)C30—C21—Br21124.1 (4)
C1—C2—C3120.8 (6)C21—C22—C23119.9 (6)
C1—C2—H2A119.6C21—C22—H22A120.1
C3—C2—H2A119.6C23—C22—H22A120.1
C4—C3—C2118.7 (6)C24—C23—C22120.4 (6)
C4—C3—H3A120.6C24—C23—H23A119.8
C2—C3—H3A120.6C22—C23—H23A119.8
C3—C4—C5122.0 (6)C23—C24—C25121.7 (6)
C3—C4—H4A119.0C23—C24—H24A119.1
C5—C4—H4A119.0C25—C24—H24A119.1
C4—C5—C6119.5 (5)C26—C25—C24118.9 (5)
C4—C5—C10121.1 (6)C26—C25—C30120.3 (6)
C6—C5—C10119.3 (6)C24—C25—C30120.8 (6)
C7—C6—C5120.6 (5)C27—C26—C25120.4 (5)
C7—C6—H6A119.7C27—C26—H26A119.8
C5—C6—H6A119.7C25—C26—H26A119.8
C6—C7—C8121.5 (6)C26—C27—C28119.4 (6)
C6—C7—H7A119.3C26—C27—H27A120.3
C8—C7—H7A119.3C28—C27—H27A120.3
C9—C8—C7122.1 (6)C29—C28—C27122.6 (6)
C9—C8—H8A119.0C29—C28—H28A118.7
C7—C8—H8A119.0C27—C28—H28A118.7
C8—C9—C10119.4 (5)C28—C29—C30119.6 (6)
C8—C9—S9119.4 (5)C28—C29—S29117.5 (5)
C10—C9—S9121.2 (4)C30—C29—S29122.9 (5)
C1—C10—C9128.8 (5)C29—C30—C21128.1 (5)
C1—C10—C5114.1 (5)C29—C30—C25117.7 (6)
C9—C10—C5117.1 (5)C21—C30—C25114.1 (5)
C9—S9—C11104.0 (3)C29—S29—C31104.7 (3)
C12—C11—S9105.7 (4)C32—C31—S29106.2 (5)
C12—C11—H11A110.6C32—C31—H31A110.5
S9—C11—H11A110.6S29—C31—H31A110.5
C12—C11—H11B110.6C32—C31—H31B110.5
S9—C11—H11B110.6S29—C31—H31B110.5
H11A—C11—H11B108.7H31A—C31—H31B108.7
C11—C12—H12A109.5C31—C32—H32A109.5
C11—C12—H12B109.5C31—C32—H32B109.5
H12A—C12—H12B109.5H32A—C32—H32B109.5
C11—C12—H12C109.5C31—C32—H32C109.5
H12A—C12—H12C109.5H32A—C32—H32C109.5
H12B—C12—H12C109.5H32B—C32—H32C109.5
C10—C1—C2—C32.1 (10)C30—C21—C22—C232.1 (9)
Br1—C1—C2—C3−175.9 (5)Br21—C21—C22—C23−179.0 (5)
C1—C2—C3—C4−1.1 (10)C21—C22—C23—C24−1.4 (9)
C2—C3—C4—C5−0.2 (10)C22—C23—C24—C25−0.2 (10)
C3—C4—C5—C6−180.0 (6)C23—C24—C25—C26−178.5 (6)
C3—C4—C5—C100.6 (10)C23—C24—C25—C301.2 (9)
C4—C5—C6—C7178.1 (6)C24—C25—C26—C27179.1 (6)
C10—C5—C6—C7−2.5 (9)C30—C25—C26—C27−0.6 (9)
C5—C6—C7—C81.4 (9)C25—C26—C27—C281.9 (9)
C6—C7—C8—C9−0.1 (9)C26—C27—C28—C29−1.6 (10)
C7—C8—C9—C100.0 (9)C27—C28—C29—C30−0.2 (9)
C7—C8—C9—S9−179.4 (5)C27—C28—C29—S29−179.6 (5)
C2—C1—C10—C9176.8 (6)C28—C29—C30—C21−178.9 (6)
Br1—C1—C10—C9−5.5 (9)S29—C29—C30—C210.4 (9)
C2—C1—C10—C5−1.5 (9)C28—C29—C30—C251.6 (8)
Br1—C1—C10—C5176.2 (4)S29—C29—C30—C25−179.2 (4)
C8—C9—C10—C1−179.4 (6)C22—C21—C30—C29179.3 (6)
S9—C9—C10—C1−0.1 (9)Br21—C21—C30—C290.5 (9)
C8—C9—C10—C5−1.0 (8)C22—C21—C30—C25−1.1 (8)
S9—C9—C10—C5178.3 (4)Br21—C21—C30—C25−179.9 (4)
C4—C5—C10—C10.2 (8)C26—C25—C30—C29−1.2 (8)
C6—C5—C10—C1−179.2 (5)C24—C25—C30—C29179.1 (5)
C4—C5—C10—C9−178.4 (6)C26—C25—C30—C21179.2 (5)
C6—C5—C10—C92.2 (8)C24—C25—C30—C21−0.5 (8)
C8—C9—S9—C112.1 (6)C28—C29—S29—C31−3.3 (6)
C10—C9—S9—C11−177.2 (5)C30—C29—S29—C31177.4 (5)
C9—S9—C11—C12175.2 (4)C29—S29—C31—C32−179.9 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C22—H22A···Br10.953.03Missing167
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C22—H22A···Br10.953.03Missing167
references
References top

Aucott, S. M., Milton, H. M., Robertson, S. D., Slawin, A. M. Z. & Woollins, J. D. (2004). Heteroat. Chem. 15, 531–542.

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.

Oki, M. & Yamada, Y. (1988). Bull. Chem. Soc. Jpn, 61, 1191–1194.

Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.

Rigaku (2006). SCXmini Benchtop Crystallography System and CrystalStructure. Rigaku, Tokyo, Japan.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.