4-(4-Bromo-5-methyl­thio­phen-2-yl)­pyridine

The title compound, C₁₀H₈BrNS, is used as a precursor to di­aryl­ethene derivatives. The dihedral angle between the thio­phene and pyridine rings is 4.9 (1)°, and there is evidence for conjugation throughout the mol­ecule. The structure is stabilized by π–π stacking interactions down the c axis.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.049
• wR factor = 0.098
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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

   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4-(4-bromo-5-methylthiophen-2-yl)pyridine

Crystal data

C10H8BrNS	F(000) = 1008
Mr = 254.14	Dx = 1.665 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 47 reflections
a = 12.726 (4) Å	θ = 5.1–12.5°
b = 11.629 (4) Å	µ = 4.21 mm^−1
c = 13.705 (5) Å	T = 295 K
V = 2028.3 (11) Å^3	Prism, yellow
Z = 8	0.4 × 0.4 × 0.3 mm

Data collection

Bruker P4 diffractometer	1028 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
Graphite monochromator	θmax = 25.0°, θmin = 2.8°
ω scans	h = −1→15
Absorption correction: multi-scan (North et al., 1968)	k = −1→13
Tmin = 0.217, Tmax = 0.283	l = −16→1
2321 measured reflections	3 standard reflections every 97 reflections
1776 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.001P)^2 + 3.5P] where P = (Fo^2 + 2Fc^2)/3
1776 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.58285 (6)	0.09948 (5)	0.58074 (6)	0.0932 (3)
S1	0.63015 (11)	0.46445 (12)	0.63320 (12)	0.0639 (4)
N1	0.2656 (4)	0.6984 (4)	0.6460 (4)	0.0766 (14)
C1	0.4972 (4)	0.4335 (4)	0.6283 (4)	0.0549 (13)
C2	0.4827 (4)	0.3181 (4)	0.6130 (4)	0.0587 (15)
H2A	0.4172	0.2828	0.6088	0.070*
C3	0.5792 (4)	0.2595 (4)	0.6044 (4)	0.0608 (14)
C4	0.6657 (4)	0.3231 (4)	0.6139 (4)	0.0593 (15)
C5	0.7819 (4)	0.2910 (5)	0.6119 (5)	0.0739 (18)
H5A	0.8206	0.3497	0.5783	0.111*
H5B	0.7906	0.2190	0.5787	0.111*
H5C	0.8076	0.2842	0.6775	0.111*
C6	0.4189 (4)	0.5242 (4)	0.6365 (4)	0.0539 (13)
C7	0.3132 (4)	0.4983 (4)	0.6342 (4)	0.0660 (15)
H7A	0.2904	0.4226	0.6292	0.079*
C8	0.2414 (5)	0.5886 (5)	0.6395 (5)	0.0769 (17)
H8A	0.1704	0.5696	0.6384	0.092*
C9	0.3682 (5)	0.7210 (5)	0.6495 (5)	0.0752 (18)
H9A	0.3887	0.7974	0.6557	0.090*
C10	0.4462 (4)	0.6388 (4)	0.6447 (4)	0.0658 (16)
H10A	0.5165	0.6604	0.6469	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0957 (5)	0.0556 (3)	0.1283 (6)	0.0089 (4)	0.0006 (5)	−0.0164 (4)
S1	0.0511 (7)	0.0553 (8)	0.0853 (11)	−0.0011 (7)	−0.0027 (8)	−0.0011 (8)
N1	0.077 (4)	0.069 (3)	0.084 (4)	0.018 (3)	0.009 (3)	0.005 (3)
C1	0.049 (3)	0.050 (3)	0.066 (4)	0.002 (2)	−0.001 (3)	0.000 (3)
C2	0.052 (3)	0.059 (3)	0.065 (4)	−0.005 (3)	0.001 (3)	−0.004 (3)
C3	0.063 (3)	0.048 (3)	0.071 (4)	0.001 (3)	0.001 (3)	−0.008 (3)
C4	0.063 (3)	0.050 (3)	0.064 (4)	0.007 (3)	0.001 (3)	0.005 (3)
C5	0.058 (3)	0.067 (4)	0.097 (5)	0.023 (3)	−0.001 (3)	0.004 (3)
C6	0.052 (3)	0.056 (3)	0.054 (3)	0.003 (3)	−0.006 (3)	0.000 (3)
C7	0.059 (3)	0.049 (3)	0.090 (4)	0.004 (3)	0.004 (3)	0.003 (3)
C8	0.054 (3)	0.080 (4)	0.096 (5)	0.006 (3)	0.009 (3)	0.009 (4)
C9	0.081 (4)	0.052 (3)	0.092 (5)	0.011 (3)	0.002 (4)	−0.002 (3)
C10	0.055 (3)	0.060 (3)	0.082 (4)	−0.003 (3)	0.001 (3)	−0.004 (3)

Geometric parameters (Å, º)

Br1—C3	1.889 (5)	C5—H5A	0.9600
S1—C4	1.726 (5)	C5—H5B	0.9600
S1—C1	1.731 (5)	C5—H5C	0.9600
N1—C8	1.317 (7)	C6—C7	1.379 (6)
N1—C9	1.333 (7)	C6—C10	1.382 (7)
C1—C2	1.371 (7)	C7—C8	1.393 (7)
C1—C6	1.456 (6)	C7—H7A	0.9300
C2—C3	1.410 (7)	C8—H8A	0.9300
C2—H2A	0.9300	C9—C10	1.379 (7)
C3—C4	1.332 (7)	C9—H9A	0.9300
C4—C5	1.526 (7)	C10—H10A	0.9300
C4—S1—C1	93.0 (2)	H5A—C5—H5C	109.5
C8—N1—C9	115.0 (5)	H5B—C5—H5C	109.5
C2—C1—C6	128.9 (5)	C7—C6—C10	117.3 (5)
C2—C1—S1	110.0 (4)	C7—C6—C1	120.5 (5)
C6—C1—S1	121.0 (4)	C10—C6—C1	122.2 (5)
C1—C2—C3	111.6 (5)	C6—C7—C8	118.3 (5)
C1—C2—H2A	124.2	C6—C7—H7A	120.9
C3—C2—H2A	124.2	C8—C7—H7A	120.9
C4—C3—C2	116.3 (5)	N1—C8—C7	125.5 (5)
C4—C3—Br1	122.9 (4)	N1—C8—H8A	117.2
C2—C3—Br1	120.8 (4)	C7—C8—H8A	117.2
C3—C4—C5	131.6 (5)	N1—C9—C10	124.5 (5)
C3—C4—S1	109.1 (4)	N1—C9—H9A	117.8
C5—C4—S1	119.3 (4)	C10—C9—H9A	117.8
C4—C5—H5A	109.5	C9—C10—C6	119.4 (5)
C4—C5—H5B	109.5	C9—C10—H10A	120.3
H5A—C5—H5B	109.5	C6—C10—H10A	120.3
C4—C5—H5C	109.5