2-Bromo-4-phenyl-1,3-thia-zole.

In the title mol-ecule, C9H6BrNS, the planes of the 2-bromo-1,3-thia-zole and phenyl rings are inclined at 7.45 (10)° with respect to each other. In the crystal, mol-ecules related by a centre of symmetry are held together via π-π inter-actions, with a short distance of 3.815 (2) Å between the centroids of the five- and six-membered rings. The crystal packing exhibits short inter-molecular S⋯Br contacts of 3.5402 (6) Å.

Related literature

For syntheses and properties of compounds containing a thia­zole fragment, see: Kelly & Lang (1995 ▶); Nicolaou et al. (1999 ▶); Cosford et al. (2003 ▶); Fyfe et al. (2004 ▶); Hamill et al. (2005 ▶). For the crystal structures of related compounds, see: Abbenante et al. (1996 ▶); Zhao et al. (2011 ▶); Ghabbour, Chia et al. (2012 ▶); Ghabbour, Kadi et al. (2012 ▶).

Experimental

Crystal data

C9H6BrNS

M = 240.12

Monoclinic,

a = 5.8934 (3) Å

b = 10.6591 (6) Å

c = 13.8697 (7) Å

β = 90.812 (1)°

V = 871.18 (8) Å3

Z = 4

Mo Kα radiation

μ = 4.89 mm−1

T = 120 K

0.15 × 0.12 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.527, T max = 0.591

12144 measured reflections

2780 independent reflections

2258 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.068

S = 1.03

2780 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681400066X/cv5440sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400066X/cv5440Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400066X/cv5440Isup3.cml

CCDC reference:

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

C9H6BrNS	F(000) = 472
Mr = 240.12	Dx = 1.831 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3185 reflections
a = 5.8934 (3) Å	θ = 2.4–29.5°
b = 10.6591 (6) Å	µ = 4.89 mm−1
c = 13.8697 (7) Å	T = 120 K
β = 90.812 (1)°	Prism, yellow
V = 871.18 (8) Å3	0.15 × 0.12 × 0.12 mm
Z = 4

Bruker APEXII CCD diffractometer	2780 independent reflections
Radiation source: fine–focus sealed tube	2258 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 31.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −8→8
Tmin = 0.527, Tmax = 0.591	k = −15→15
12144 measured reflections	l = −20→19

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0323P)2 + 0.1245P] where P = (Fo2 + 2Fc2)/3
2780 reflections	(Δ/σ)max = 0.002
109 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

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
Br1	0.21824 (3)	0.90020 (2)	0.576233 (15)	0.02238 (7)
S1	−0.24024 (8)	0.75866 (5)	0.55984 (4)	0.01975 (11)
C2	0.0322 (3)	0.77659 (19)	0.52049 (14)	0.0165 (4)
N3	0.0960 (3)	0.70330 (16)	0.45150 (11)	0.0161 (3)
C4	−0.0825 (3)	0.62475 (17)	0.42443 (14)	0.0144 (4)
C5	−0.2768 (3)	0.64278 (19)	0.47549 (14)	0.0178 (4)
H5	−0.4135	0.5972	0.4655	0.021*
C6	−0.0500 (3)	0.53485 (18)	0.34463 (14)	0.0151 (4)
C7	−0.2155 (3)	0.4453 (2)	0.32167 (14)	0.0184 (4)
H7	−0.3508	0.4419	0.3580	0.022*
C8	−0.1849 (4)	0.3613 (2)	0.24652 (14)	0.0214 (4)
H8	−0.2988	0.3009	0.2318	0.026*
C9	0.0134 (4)	0.3655 (2)	0.19254 (15)	0.0213 (4)
H9	0.0354	0.3080	0.1411	0.026*
C10	0.1778 (4)	0.4544 (2)	0.21484 (15)	0.0208 (4)
H10	0.3130	0.4576	0.1784	0.025*
C11	0.1471 (3)	0.53900 (19)	0.28978 (14)	0.0174 (4)
H11	0.2605	0.5999	0.3038	0.021*

	U11	U22	U33	U12	U13	U23
Br1	0.02065 (11)	0.02080 (11)	0.02561 (12)	−0.00021 (8)	−0.00253 (8)	−0.00725 (8)
S1	0.0181 (2)	0.0210 (3)	0.0202 (2)	0.00233 (19)	0.00358 (19)	−0.00361 (19)
C2	0.0156 (9)	0.0158 (9)	0.0181 (9)	0.0006 (7)	−0.0012 (7)	−0.0013 (7)
N3	0.0167 (8)	0.0160 (8)	0.0155 (8)	−0.0008 (6)	−0.0005 (6)	−0.0006 (6)
C4	0.0162 (9)	0.0129 (9)	0.0142 (8)	0.0009 (7)	−0.0008 (7)	0.0015 (7)
C5	0.0173 (9)	0.0173 (9)	0.0190 (10)	0.0002 (7)	0.0009 (7)	−0.0011 (8)
C6	0.0187 (9)	0.0137 (9)	0.0129 (8)	0.0020 (7)	−0.0013 (7)	0.0015 (7)
C7	0.0194 (9)	0.0182 (9)	0.0176 (9)	−0.0013 (8)	0.0002 (7)	0.0010 (8)
C8	0.0264 (10)	0.0180 (10)	0.0198 (10)	−0.0019 (8)	−0.0054 (8)	−0.0004 (8)
C9	0.0307 (11)	0.0180 (10)	0.0153 (9)	0.0045 (8)	−0.0019 (8)	−0.0026 (7)
C10	0.0224 (10)	0.0225 (10)	0.0175 (9)	0.0041 (8)	0.0028 (8)	0.0006 (8)
C11	0.0184 (9)	0.0165 (9)	0.0172 (9)	−0.0013 (7)	0.0019 (7)	−0.0004 (7)

Br1—C2	1.874 (2)	C7—C8	1.388 (3)
S1—C5	1.713 (2)	C7—H7	0.9500
S1—C2	1.714 (2)	C8—C9	1.398 (3)
C2—N3	1.295 (2)	C8—H8	0.9500
N3—C4	1.392 (2)	C9—C10	1.388 (3)
C4—C5	1.368 (3)	C9—H9	0.9500
C4—C6	1.478 (3)	C10—C11	1.390 (3)
C5—H5	0.9500	C10—H10	0.9500
C6—C11	1.398 (3)	C11—H11	0.9500
C6—C7	1.398 (3)
C5—S1—C2	88.40 (10)	C8—C7—H7	119.5
N3—C2—S1	116.81 (15)	C6—C7—H7	119.5
N3—C2—Br1	123.68 (15)	C7—C8—C9	120.0 (2)
S1—C2—Br1	119.49 (11)	C7—C8—H8	120.0
C2—N3—C4	109.64 (17)	C9—C8—H8	120.0
C5—C4—N3	114.24 (17)	C10—C9—C8	119.28 (19)
C5—C4—C6	126.63 (18)	C10—C9—H9	120.4
N3—C4—C6	119.11 (17)	C8—C9—H9	120.4
C4—C5—S1	110.91 (15)	C9—C10—C11	120.80 (19)
C4—C5—H5	124.5	C9—C10—H10	119.6
S1—C5—H5	124.5	C11—C10—H10	119.6
C11—C6—C7	118.68 (18)	C10—C11—C6	120.30 (19)
C11—C6—C4	120.27 (17)	C10—C11—H11	119.9
C7—C6—C4	121.05 (17)	C6—C11—H11	119.9
C8—C7—C6	120.92 (19)
C5—S1—C2—N3	−0.65 (17)	C5—C4—C6—C7	−8.5 (3)
C5—S1—C2—Br1	178.28 (13)	N3—C4—C6—C7	173.20 (18)
S1—C2—N3—C4	0.5 (2)	C11—C6—C7—C8	0.5 (3)
Br1—C2—N3—C4	−178.35 (13)	C4—C6—C7—C8	179.78 (19)
C2—N3—C4—C5	−0.1 (2)	C6—C7—C8—C9	0.0 (3)
C2—N3—C4—C6	178.41 (17)	C7—C8—C9—C10	−0.2 (3)
N3—C4—C5—S1	−0.4 (2)	C8—C9—C10—C11	−0.1 (3)
C6—C4—C5—S1	−178.74 (16)	C9—C10—C11—C6	0.6 (3)
C2—S1—C5—C4	0.56 (16)	C7—C6—C11—C10	−0.8 (3)
C5—C4—C6—C11	170.74 (19)	C4—C6—C11—C10	179.93 (18)
N3—C4—C6—C11	−7.5 (3)