1-Bromo-8-(ethyl­sulfan­yl)naphthalene

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

doi:10.1107/S1600536807042432

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1-Bromo-8-(ethylsulfanyl)naphthalene

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

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 π–π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042432/hb2511sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042432/hb2511Isup2.hkl Contains datablock I

CCDC reference: 663689

checkCIF report

Key indicators

Single-crystal X-ray study
T = 125 K
Mean (C-C) = 0.009 Å
R factor = 0.053
wR factor = 0.106
Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96

Alert level C
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        400 Ang.
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9
PLAT480_ALERT_4_C Long H...A H-Bond Reported H22A   ..  BR1     ..       3.03 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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.

Structure description top

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

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

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

C₁₂H₁₁BrS	F(000) = 1072
M_r = 267.18	D_x = 1.688 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3763 reflections
a = 11.632 (4) Å	θ = 1.6–25.2°
b = 12.260 (4) Å	µ = 4.06 mm⁻¹
c = 14.748 (4) Å	T = 125 K
β = 91.692 (9)°	Block, colourless
V = 2102.2 (11) Å³	0.25 × 0.20 × 0.20 mm
Z = 8

Data collection top

Rigaku SCXmini CCD diffractometer	3543 independent reflections
Radiation source: fine-focus sealed tube	2316 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
ω scans	θ_max = 25.0°, θ_min = 7.8°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = 0→13
T_min = 0.396, T_max = 0.452	k = −14→14
6713 measured reflections	l = −17→17

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.044P)²] where P = (F_o² + 2F_c²)/3
3543 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₂H₁₁BrS	V = 2102.2 (11) Å³
M_r = 267.18	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.632 (4) Å	µ = 4.06 mm⁻¹
b = 12.260 (4) Å	T = 125 K
c = 14.748 (4) Å	0.25 × 0.20 × 0.20 mm
β = 91.692 (9)°

Data collection top

Rigaku SCXmini CCD diffractometer	3543 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2316 reflections with I > 2σ(I)
T_min = 0.396, T_max = 0.452	R_int = 0.079
6713 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 0.99	Δρ_max = 0.46 e Å⁻³
3543 reflections	Δρ_min = −0.47 e Å⁻³
254 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
Br1	0.07289 (6)	0.47998 (5)	0.38936 (4)	0.02453 (19)
C1	0.0346 (5)	0.4500 (5)	0.2657 (4)	0.0190 (14)
C2	−0.0539 (6)	0.5134 (6)	0.2332 (4)	0.0275 (15)
H2A	−0.0850	0.5682	0.2709	0.033*
C3	−0.0995 (6)	0.4985 (6)	0.1450 (5)	0.0291 (17)
H3A	−0.1620	0.5418	0.1229	0.035*
C4	−0.0529 (5)	0.4216 (6)	0.0921 (4)	0.0229 (15)
H4A	−0.0837	0.4111	0.0323	0.027*
C5	0.0391 (5)	0.3568 (5)	0.1223 (4)	0.0201 (14)
C6	0.0854 (5)	0.2758 (5)	0.0626 (4)	0.0191 (14)
H6A	0.0515	0.2656	0.0038	0.023*
C7	0.1740 (6)	0.2160 (5)	0.0887 (4)	0.0195 (14)
H7A	0.2043	0.1642	0.0478	0.023*
C8	0.2248 (6)	0.2269 (5)	0.1753 (4)	0.0222 (14)
H8A	0.2887	0.1821	0.1917	0.027*
C9	0.1853 (5)	0.3003 (5)	0.2373 (4)	0.0172 (13)
C10	0.0884 (5)	0.3688 (5)	0.2130 (3)	0.0138 (12)
S9	0.25526 (14)	0.31016 (13)	0.34520 (10)	0.0209 (4)
C11	0.3730 (6)	0.2139 (5)	0.3396 (4)	0.0222 (14)
H11A	0.3434	0.1385	0.3332	0.027*
H11B	0.4215	0.2304	0.2872	0.027*
C12	0.4421 (6)	0.2271 (5)	0.4288 (4)	0.0253 (15)
H12A	0.5073	0.1766	0.4298	0.038*
H12B	0.3926	0.2111	0.4798	0.038*
H12C	0.4705	0.3022	0.4339	0.038*
Br21	0.33155 (6)	0.74894 (6)	0.39260 (4)	0.0266 (2)
C21	0.2805 (5)	0.7861 (5)	0.2732 (4)	0.0184 (14)
C22	0.1837 (6)	0.7288 (5)	0.2451 (4)	0.0254 (15)
H22A	0.1494	0.6781	0.2848	0.031*
C23	0.1365 (6)	0.7454 (6)	0.1584 (4)	0.0270 (15)
H23A	0.0708	0.7048	0.1387	0.032*
C24	0.1827 (6)	0.8179 (5)	0.1030 (4)	0.0236 (15)
H24A	0.1493	0.8279	0.0440	0.028*
C25	0.2803 (5)	0.8805 (5)	0.1297 (4)	0.0209 (14)
C26	0.3233 (6)	0.9574 (5)	0.0688 (4)	0.0220 (15)
H26A	0.2874	0.9659	0.0106	0.026*
C27	0.4170 (6)	1.0206 (6)	0.0931 (4)	0.0261 (15)
H27A	0.4446	1.0742	0.0525	0.031*
C28	0.4710 (6)	1.0053 (5)	0.1774 (4)	0.0255 (15)
H28A	0.5368	1.0481	0.1929	0.031*
C29	0.4327 (5)	0.9304 (5)	0.2397 (4)	0.0186 (13)
C30	0.3345 (5)	0.8662 (5)	0.2180 (4)	0.0164 (13)
S29	0.50989 (14)	0.92059 (13)	0.34520 (10)	0.0221 (4)
C31	0.6292 (5)	1.0142 (5)	0.3351 (4)	0.0227 (14)
H31A	0.6778	0.9927	0.2841	0.027*
H31B	0.6008	1.0893	0.3243	0.027*
C32	0.6973 (6)	1.0079 (6)	0.4242 (5)	0.0309 (17)
H32A	0.7635	1.0571	0.4221	0.046*
H32B	0.7243	0.9330	0.4341	0.046*
H32C	0.6481	1.0295	0.4739	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0280 (4)	0.0259 (3)	0.0197 (3)	0.0037 (3)	−0.0004 (3)	−0.0061 (3)
C1	0.021 (3)	0.018 (3)	0.018 (3)	0.001 (3)	0.003 (3)	−0.002 (2)
C2	0.031 (4)	0.025 (4)	0.027 (3)	0.003 (3)	0.006 (3)	0.001 (3)
C3	0.019 (3)	0.045 (5)	0.024 (3)	0.010 (3)	−0.001 (3)	0.015 (3)
C4	0.013 (3)	0.039 (4)	0.016 (3)	−0.004 (3)	−0.002 (3)	0.004 (3)
C5	0.021 (3)	0.026 (3)	0.014 (3)	−0.009 (3)	0.002 (3)	0.001 (3)
C6	0.015 (3)	0.032 (4)	0.010 (3)	−0.010 (3)	−0.005 (2)	−0.001 (3)
C7	0.026 (4)	0.019 (3)	0.013 (3)	−0.009 (3)	0.003 (3)	−0.006 (2)
C8	0.025 (4)	0.018 (3)	0.024 (3)	0.001 (3)	0.003 (3)	0.004 (3)
C9	0.018 (3)	0.014 (3)	0.019 (3)	−0.004 (3)	−0.006 (3)	0.005 (3)
C10	0.013 (3)	0.022 (3)	0.006 (3)	−0.009 (3)	−0.001 (2)	0.003 (2)
S9	0.0258 (9)	0.0229 (8)	0.0140 (7)	0.0070 (7)	−0.0020 (7)	−0.0021 (6)
C11	0.025 (4)	0.022 (3)	0.019 (3)	0.004 (3)	−0.003 (3)	−0.001 (3)
C12	0.025 (4)	0.026 (4)	0.024 (3)	0.008 (3)	−0.008 (3)	0.002 (3)
Br21	0.0342 (4)	0.0279 (4)	0.0174 (3)	−0.0057 (3)	−0.0042 (3)	0.0074 (3)
C21	0.020 (3)	0.021 (3)	0.014 (3)	0.005 (3)	−0.001 (3)	−0.005 (2)
C22	0.025 (4)	0.024 (4)	0.028 (3)	−0.003 (3)	0.006 (3)	−0.003 (3)
C23	0.021 (4)	0.034 (4)	0.026 (4)	0.003 (3)	−0.004 (3)	−0.010 (3)
C24	0.021 (4)	0.034 (4)	0.015 (3)	0.012 (3)	−0.004 (3)	−0.004 (3)
C25	0.021 (3)	0.028 (4)	0.013 (3)	0.016 (3)	0.000 (3)	−0.006 (3)
C26	0.027 (4)	0.027 (4)	0.012 (3)	0.012 (3)	0.002 (3)	0.002 (3)
C27	0.035 (4)	0.024 (3)	0.020 (3)	0.007 (3)	0.014 (3)	0.012 (3)
C28	0.032 (4)	0.015 (3)	0.029 (3)	−0.004 (3)	0.005 (3)	−0.003 (3)
C29	0.019 (3)	0.021 (3)	0.016 (3)	0.008 (3)	0.001 (3)	−0.001 (3)
C30	0.023 (3)	0.013 (3)	0.014 (3)	0.008 (3)	0.001 (2)	−0.005 (2)
S29	0.0246 (9)	0.0236 (9)	0.0179 (8)	−0.0030 (7)	−0.0032 (7)	0.0010 (7)
C31	0.021 (3)	0.022 (3)	0.025 (3)	−0.001 (3)	−0.003 (3)	−0.002 (3)
C32	0.031 (4)	0.027 (4)	0.034 (4)	−0.008 (3)	−0.007 (3)	−0.004 (3)

Geometric parameters (Å, º) top

Br1—C1	1.901 (6)	Br21—C21	1.897 (6)
C1—C2	1.365 (9)	C21—C22	1.381 (9)
C1—C10	1.419 (8)	C21—C30	1.433 (9)
C2—C3	1.403 (10)	C22—C23	1.391 (9)
C2—H2A	0.9500	C22—H22A	0.9500
C3—C4	1.348 (9)	C23—C24	1.331 (10)
C3—H3A	0.9500	C23—H23A	0.9500
C4—C5	1.395 (9)	C24—C25	1.417 (10)
C4—H4A	0.9500	C24—H24A	0.9500
C5—C6	1.443 (9)	C25—C26	1.404 (9)
C5—C10	1.446 (8)	C25—C30	1.441 (8)
C6—C7	1.312 (9)	C26—C27	1.376 (10)
C6—H6A	0.9500	C26—H26A	0.9500
C7—C8	1.398 (8)	C27—C28	1.388 (10)
C7—H7A	0.9500	C27—H27A	0.9500
C8—C9	1.371 (9)	C28—C29	1.382 (9)
C8—H8A	0.9500	C28—H28A	0.9500
C9—C10	1.443 (8)	C29—C30	1.415 (9)
C9—S9	1.770 (6)	C29—S29	1.778 (6)
S9—C11	1.811 (7)	S29—C31	1.810 (7)
C11—C12	1.530 (9)	C31—C32	1.516 (9)
C11—H11A	0.9900	C31—H31A	0.9900
C11—H11B	0.9900	C31—H31B	0.9900
C12—H12A	0.9800	C32—H32A	0.9800
C12—H12B	0.9800	C32—H32B	0.9800
C12—H12C	0.9800	C32—H32C	0.9800

C2—C1—C10	123.2 (6)	C22—C21—C30	123.1 (5)
C2—C1—Br1	112.3 (5)	C22—C21—Br21	112.8 (5)
C10—C1—Br1	124.5 (4)	C30—C21—Br21	124.1 (4)
C1—C2—C3	120.8 (6)	C21—C22—C23	119.9 (6)
C1—C2—H2A	119.6	C21—C22—H22A	120.1
C3—C2—H2A	119.6	C23—C22—H22A	120.1
C4—C3—C2	118.7 (6)	C24—C23—C22	120.4 (6)
C4—C3—H3A	120.6	C24—C23—H23A	119.8
C2—C3—H3A	120.6	C22—C23—H23A	119.8
C3—C4—C5	122.0 (6)	C23—C24—C25	121.7 (6)
C3—C4—H4A	119.0	C23—C24—H24A	119.1
C5—C4—H4A	119.0	C25—C24—H24A	119.1
C4—C5—C6	119.5 (5)	C26—C25—C24	118.9 (5)
C4—C5—C10	121.1 (6)	C26—C25—C30	120.3 (6)
C6—C5—C10	119.3 (6)	C24—C25—C30	120.8 (6)
C7—C6—C5	120.6 (5)	C27—C26—C25	120.4 (5)
C7—C6—H6A	119.7	C27—C26—H26A	119.8
C5—C6—H6A	119.7	C25—C26—H26A	119.8
C6—C7—C8	121.5 (6)	C26—C27—C28	119.4 (6)
C6—C7—H7A	119.3	C26—C27—H27A	120.3
C8—C7—H7A	119.3	C28—C27—H27A	120.3
C9—C8—C7	122.1 (6)	C29—C28—C27	122.6 (6)
C9—C8—H8A	119.0	C29—C28—H28A	118.7
C7—C8—H8A	119.0	C27—C28—H28A	118.7
C8—C9—C10	119.4 (5)	C28—C29—C30	119.6 (6)
C8—C9—S9	119.4 (5)	C28—C29—S29	117.5 (5)
C10—C9—S9	121.2 (4)	C30—C29—S29	122.9 (5)
C1—C10—C9	128.8 (5)	C29—C30—C21	128.1 (5)
C1—C10—C5	114.1 (5)	C29—C30—C25	117.7 (6)
C9—C10—C5	117.1 (5)	C21—C30—C25	114.1 (5)
C9—S9—C11	104.0 (3)	C29—S29—C31	104.7 (3)
C12—C11—S9	105.7 (4)	C32—C31—S29	106.2 (5)
C12—C11—H11A	110.6	C32—C31—H31A	110.5
S9—C11—H11A	110.6	S29—C31—H31A	110.5
C12—C11—H11B	110.6	C32—C31—H31B	110.5
S9—C11—H11B	110.6	S29—C31—H31B	110.5
H11A—C11—H11B	108.7	H31A—C31—H31B	108.7
C11—C12—H12A	109.5	C31—C32—H32A	109.5
C11—C12—H12B	109.5	C31—C32—H32B	109.5
H12A—C12—H12B	109.5	H32A—C32—H32B	109.5
C11—C12—H12C	109.5	C31—C32—H32C	109.5
H12A—C12—H12C	109.5	H32A—C32—H32C	109.5
H12B—C12—H12C	109.5	H32B—C32—H32C	109.5

C10—C1—C2—C3	2.1 (10)	C30—C21—C22—C23	2.1 (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—C10	0.6 (10)	C23—C24—C25—C30	1.2 (9)
C4—C5—C6—C7	178.1 (6)	C24—C25—C26—C27	179.1 (6)
C10—C5—C6—C7	−2.5 (9)	C30—C25—C26—C27	−0.6 (9)
C5—C6—C7—C8	1.4 (9)	C25—C26—C27—C28	1.9 (9)
C6—C7—C8—C9	−0.1 (9)	C26—C27—C28—C29	−1.6 (10)
C7—C8—C9—C10	0.0 (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—C9	176.8 (6)	C28—C29—C30—C21	−178.9 (6)
Br1—C1—C10—C9	−5.5 (9)	S29—C29—C30—C21	0.4 (9)
C2—C1—C10—C5	−1.5 (9)	C28—C29—C30—C25	1.6 (8)
Br1—C1—C10—C5	176.2 (4)	S29—C29—C30—C25	−179.2 (4)
C8—C9—C10—C1	−179.4 (6)	C22—C21—C30—C29	179.3 (6)
S9—C9—C10—C1	−0.1 (9)	Br21—C21—C30—C29	0.5 (9)
C8—C9—C10—C5	−1.0 (8)	C22—C21—C30—C25	−1.1 (8)
S9—C9—C10—C5	178.3 (4)	Br21—C21—C30—C25	−179.9 (4)
C4—C5—C10—C1	0.2 (8)	C26—C25—C30—C29	−1.2 (8)
C6—C5—C10—C1	−179.2 (5)	C24—C25—C30—C29	179.1 (5)
C4—C5—C10—C9	−178.4 (6)	C26—C25—C30—C21	179.2 (5)
C6—C5—C10—C9	2.2 (8)	C24—C25—C30—C21	−0.5 (8)
C8—C9—S9—C11	2.1 (6)	C28—C29—S29—C31	−3.3 (6)
C10—C9—S9—C11	−177.2 (5)	C30—C29—S29—C31	177.4 (5)
C9—S9—C11—C12	175.2 (4)	C29—S29—C31—C32	−179.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22A···Br1	0.95	3.03	Missing	167

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁BrS
M_r	267.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	125
a, b, c (Å)	11.632 (4), 12.260 (4), 14.748 (4)
β (°)	91.692 (9)
V (Å³)	2102.2 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	4.06
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini CCD
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.396, 0.452
No. of measured, independent and observed [I > 2σ(I)] reflections	6713, 3543, 2316
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.106, 0.99
No. of reflections	3543
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.47

Computer programs: SCXmini (Rigaku, 2006), PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), CrystalStructure (Rigaku, 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22A···Br1	0.95	3.025	Missing	167

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