Crystal structure of 2-(p-tol-yl)-6-(tri-fluoro-meth-yl)benzo[b]thio-phene-3-carbo-nitrile.

In the title compound, C17H10F3NS, the dihedral angle between the fused benzo-thio-phene ring system (r.m.s. deviation = 0.042 Å) and the benzene ring is 29.78 (11)°. The crystal structure features C-H⋯F and very weak C-H⋯N hydrogen bonds, which generate (001) sheets.

Related literature

For background to benzo­thio­phene derivatives, see: Bettinetti et al. (2002 ▸); Roberts & Hartley (2004 ▸).

Experimental

Crystal data

C17H10F3NS

M = 317.33

Monoclinic,

a = 13.7576 (5) Å

b = 14.5343 (6) Å

c = 7.1353 (3) Å

β = 92.817 (3)°

V = 1425.03 (10) Å3

Z = 4

Cu Kα radiation

μ = 2.29 mm−1

T = 293 K

0.30 × 0.27 × 0.25 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.546, T max = 0.598

7045 measured reflections

2316 independent reflections

1860 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.141

S = 1.06

2316 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015008671/hb7416sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015008671/hb7416Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015008671/hb7416Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015008671/hb7416fig1.tif

A view of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015008671/hb7416fig2.tif

A view along the a axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 2 for details).

CCDC reference: 1063141

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

C17H10F3NS	F(000) = 648
Mr = 317.33	Dx = 1.479 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 2316 reflections
a = 13.7576 (5) Å	θ = 6.4–64.7°
b = 14.5343 (6) Å	µ = 2.29 mm−1
c = 7.1353 (3) Å	T = 293 K
β = 92.817 (3)°	Block, colourless
V = 1425.03 (10) Å3	0.30 × 0.27 × 0.25 mm
Z = 4

Bruker X8 Proteum diffractometer	2316 independent reflections
Radiation source: Rotating Anode	1860 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
Detector resolution: 18.4 pixels mm-1	θmax = 64.7°, θmin = 6.4°
φ and ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −15→16
Tmin = 0.546, Tmax = 0.598	l = −8→6
7045 measured reflections

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) = 0.141	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0726P)2 + 0.2459P] where P = (Fo2 + 2Fc2)/3
2316 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.51842 (5)	0.17833 (5)	0.23250 (10)	0.0214 (2)
F13	0.10569 (13)	−0.01265 (15)	0.0632 (4)	0.0518 (8)
F14	0.14077 (13)	0.11887 (16)	−0.0469 (3)	0.0450 (7)
F15	0.11752 (13)	0.10360 (17)	0.2439 (3)	0.0484 (8)
N11	0.64047 (19)	−0.14957 (19)	0.3600 (4)	0.0297 (9)
C2	0.4251 (2)	0.0996 (2)	0.1944 (4)	0.0202 (9)
C3	0.3272 (2)	0.1178 (2)	0.1485 (4)	0.0212 (9)
C4	0.2634 (2)	0.0444 (2)	0.1373 (4)	0.0210 (9)
C5	0.2957 (2)	−0.0459 (2)	0.1679 (4)	0.0217 (9)
C6	0.3920 (2)	−0.0643 (2)	0.2103 (4)	0.0203 (8)
C7	0.4583 (2)	0.0087 (2)	0.2249 (4)	0.0178 (8)
C8	0.5601 (2)	0.0069 (2)	0.2816 (4)	0.0174 (8)
C9	0.6018 (2)	0.0928 (2)	0.2949 (4)	0.0183 (8)
C10	0.6079 (2)	−0.0785 (2)	0.3267 (4)	0.0204 (9)
C12	0.1574 (2)	0.0636 (2)	0.0993 (4)	0.0253 (9)
C16	0.7014 (2)	0.1180 (2)	0.3613 (4)	0.0182 (8)
C17	0.7798 (2)	0.0588 (2)	0.3430 (4)	0.0198 (9)
C18	0.8717 (2)	0.0826 (2)	0.4144 (4)	0.0236 (9)
C19	0.8890 (2)	0.1655 (2)	0.5074 (4)	0.0235 (9)
C20	0.8107 (2)	0.2255 (2)	0.5220 (4)	0.0217 (9)
C21	0.7190 (2)	0.2025 (2)	0.4506 (4)	0.0194 (8)
C22	0.9878 (2)	0.1887 (2)	0.5939 (5)	0.0306 (10)
H3	0.30560	0.17760	0.12600	0.0250*
H5	0.25120	−0.09410	0.15940	0.0260*
H6	0.41310	−0.12450	0.22910	0.0240*
H17	0.77040	0.00260	0.28230	0.0240*
H18	0.92320	0.04210	0.39990	0.0280*
H20	0.82050	0.28200	0.58110	0.0260*
H21	0.66800	0.24390	0.46190	0.0230*
H22A	0.99640	0.15870	0.71340	0.0460*
H22B	0.99300	0.25410	0.61070	0.0460*
H22C	1.03700	0.16810	0.51280	0.0460*

	U11	U22	U33	U12	U13	U23
S1	0.0194 (4)	0.0164 (4)	0.0281 (4)	−0.0001 (3)	−0.0009 (3)	0.0010 (3)
F13	0.0215 (9)	0.0385 (13)	0.0941 (17)	−0.0028 (9)	−0.0107 (10)	−0.0047 (12)
F14	0.0293 (10)	0.0607 (15)	0.0442 (12)	0.0123 (10)	−0.0052 (9)	0.0178 (11)
F15	0.0285 (10)	0.0782 (17)	0.0390 (11)	0.0161 (10)	0.0059 (9)	−0.0160 (11)
N11	0.0321 (15)	0.0196 (16)	0.0369 (16)	0.0022 (12)	−0.0027 (12)	0.0019 (13)
C2	0.0237 (15)	0.0198 (16)	0.0171 (14)	−0.0014 (12)	0.0024 (11)	−0.0003 (13)
C3	0.0214 (14)	0.0211 (17)	0.0210 (14)	0.0051 (12)	0.0011 (12)	−0.0005 (13)
C4	0.0223 (15)	0.0258 (17)	0.0149 (13)	−0.0007 (13)	0.0005 (11)	−0.0005 (13)
C5	0.0244 (15)	0.0211 (17)	0.0196 (14)	−0.0038 (12)	−0.0001 (12)	−0.0010 (13)
C6	0.0268 (15)	0.0145 (15)	0.0198 (14)	−0.0004 (12)	0.0026 (12)	0.0003 (12)
C7	0.0216 (14)	0.0207 (16)	0.0111 (13)	0.0011 (12)	0.0023 (11)	0.0016 (12)
C8	0.0203 (14)	0.0170 (15)	0.0149 (13)	0.0012 (12)	0.0017 (11)	−0.0007 (12)
C9	0.0220 (14)	0.0191 (16)	0.0142 (13)	0.0006 (12)	0.0041 (11)	−0.0006 (12)
C10	0.0199 (14)	0.0220 (18)	0.0191 (15)	−0.0039 (13)	−0.0011 (12)	−0.0006 (13)
C12	0.0240 (15)	0.0254 (18)	0.0265 (16)	0.0002 (13)	0.0002 (13)	−0.0017 (14)
C16	0.0206 (14)	0.0174 (16)	0.0166 (13)	−0.0004 (12)	0.0005 (11)	0.0015 (12)
C17	0.0219 (15)	0.0169 (16)	0.0209 (14)	−0.0001 (12)	0.0034 (12)	−0.0013 (13)
C18	0.0229 (15)	0.0240 (17)	0.0241 (15)	0.0042 (13)	0.0026 (12)	−0.0007 (13)
C19	0.0237 (15)	0.0293 (18)	0.0175 (14)	−0.0019 (13)	0.0003 (12)	0.0033 (13)
C20	0.0240 (15)	0.0223 (17)	0.0187 (14)	−0.0044 (13)	0.0011 (12)	−0.0009 (13)
C21	0.0204 (14)	0.0186 (16)	0.0195 (14)	0.0003 (12)	0.0032 (11)	0.0022 (13)
C22	0.0251 (16)	0.037 (2)	0.0295 (16)	0.0014 (14)	−0.0015 (13)	−0.0015 (16)

S1—C2	1.731 (3)	C16—C17	1.391 (4)
S1—C9	1.735 (3)	C16—C21	1.399 (4)
F13—C12	1.335 (4)	C17—C18	1.384 (4)
F14—C12	1.328 (4)	C18—C19	1.390 (4)
F15—C12	1.326 (4)	C19—C20	1.394 (4)
N11—C10	1.146 (4)	C19—C22	1.503 (4)
C2—C3	1.396 (4)	C20—C21	1.378 (4)
C2—C7	1.411 (4)	C3—H3	0.9300
C3—C4	1.381 (4)	C5—H5	0.9300
C4—C5	1.399 (4)	C6—H6	0.9300
C4—C12	1.496 (4)	C17—H17	0.9300
C5—C6	1.371 (4)	C18—H18	0.9300
C6—C7	1.400 (4)	C20—H20	0.9300
C7—C8	1.439 (4)	C21—H21	0.9300
C8—C9	1.375 (4)	C22—H22A	0.9600
C8—C10	1.434 (4)	C22—H22B	0.9600
C9—C16	1.474 (4)	C22—H22C	0.9600
C2—S1—C9	92.44 (14)	C17—C16—C21	117.9 (3)
S1—C2—C3	127.7 (2)	C16—C17—C18	120.6 (3)
S1—C2—C7	111.3 (2)	C17—C18—C19	121.6 (3)
C3—C2—C7	121.0 (3)	C18—C19—C20	117.6 (3)
C2—C3—C4	118.1 (3)	C18—C19—C22	121.4 (3)
C3—C4—C5	121.3 (3)	C20—C19—C22	121.0 (3)
C3—C4—C12	118.5 (3)	C19—C20—C21	121.2 (3)
C5—C4—C12	120.2 (3)	C16—C21—C20	121.1 (3)
C4—C5—C6	120.9 (3)	C2—C3—H3	121.00
C5—C6—C7	119.2 (3)	C4—C3—H3	121.00
C2—C7—C6	119.6 (3)	C4—C5—H5	120.00
C2—C7—C8	111.3 (2)	C6—C5—H5	120.00
C6—C7—C8	129.0 (3)	C5—C6—H6	120.00
C7—C8—C9	113.6 (3)	C7—C6—H6	120.00
C7—C8—C10	120.6 (3)	C16—C17—H17	120.00
C9—C8—C10	125.8 (3)	C18—C17—H17	120.00
S1—C9—C8	111.4 (2)	C17—C18—H18	119.00
S1—C9—C16	119.8 (2)	C19—C18—H18	119.00
C8—C9—C16	128.7 (3)	C19—C20—H20	119.00
N11—C10—C8	175.6 (3)	C21—C20—H20	119.00
F13—C12—F14	106.3 (2)	C16—C21—H21	120.00
F13—C12—F15	106.1 (2)	C20—C21—H21	119.00
F13—C12—C4	112.7 (2)	C19—C22—H22A	109.00
F14—C12—F15	106.5 (2)	C19—C22—H22B	109.00
F14—C12—C4	112.6 (2)	C19—C22—H22C	109.00
F15—C12—C4	112.2 (2)	H22A—C22—H22B	109.00
C9—C16—C17	121.9 (3)	H22A—C22—H22C	110.00
C9—C16—C21	120.1 (3)	H22B—C22—H22C	109.00
C9—S1—C2—C3	175.6 (3)	C2—C7—C8—C9	0.5 (4)
C9—S1—C2—C7	−1.4 (2)	C2—C7—C8—C10	177.7 (3)
C2—S1—C9—C8	1.7 (2)	C6—C7—C8—C9	−175.0 (3)
C2—S1—C9—C16	−175.3 (2)	C6—C7—C8—C10	2.2 (5)
S1—C2—C3—C4	−175.5 (2)	C7—C8—C9—S1	−1.6 (3)
C7—C2—C3—C4	1.2 (4)	C7—C8—C9—C16	175.2 (3)
S1—C2—C7—C6	176.7 (2)	C10—C8—C9—S1	−178.6 (2)
S1—C2—C7—C8	0.8 (3)	C10—C8—C9—C16	−1.8 (5)
C3—C2—C7—C6	−0.5 (4)	S1—C9—C16—C17	−154.1 (2)
C3—C2—C7—C8	−176.4 (3)	S1—C9—C16—C21	27.8 (4)
C2—C3—C4—C5	−1.0 (4)	C8—C9—C16—C17	29.4 (5)
C2—C3—C4—C12	176.5 (3)	C8—C9—C16—C21	−148.7 (3)
C3—C4—C5—C6	0.1 (4)	C9—C16—C17—C18	−177.0 (3)
C12—C4—C5—C6	−177.4 (3)	C21—C16—C17—C18	1.2 (4)
C3—C4—C12—F13	170.3 (3)	C9—C16—C21—C20	176.8 (3)
C3—C4—C12—F14	50.1 (4)	C17—C16—C21—C20	−1.5 (4)
C3—C4—C12—F15	−70.0 (3)	C16—C17—C18—C19	0.4 (4)
C5—C4—C12—F13	−12.2 (4)	C17—C18—C19—C20	−1.8 (4)
C5—C4—C12—F14	−132.4 (3)	C17—C18—C19—C22	176.6 (3)
C5—C4—C12—F15	107.5 (3)	C18—C19—C20—C21	1.5 (4)
C4—C5—C6—C7	0.7 (4)	C22—C19—C20—C21	−176.9 (3)
C5—C6—C7—C2	−0.5 (4)	C19—C20—C21—C16	0.1 (4)
C5—C6—C7—C8	174.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N11i	0.93	2.62	3.411 (4)	143
C22—H22C···F15ii	0.96	2.45	3.375 (4)	162

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C3H3N11i	0.93	2.62	3.411(4)	143
C22H22CF15ii	0.96	2.45	3.375(4)	162

Symmetry codes: (i) ; (ii) .