Crystal structure of 2-fluoro-N-(1,3-thia-zol-2-yl)benzamide.

In the title compound, C10H7FN2OS, the mean plane of the central amide fragment (r.m.s. deviation = 0.048 Å) makes dihedral angles of 35.28 (8) and 10.14 (12)° with those of the fluoro-benzene and thia-zole rings, respectively. The thia-zole S and amide O atoms lie to the same side of the mol-ecule. In the crystal, pairs of N-H⋯N hydrogen bonds connect the mol-ecules into inversion dimers with R 2 (2)(8) motifs, and weak C-H⋯O inter-actions connect the mol-ecules into C(6) [001] chains. Together, the N-H⋯N and C-H⋯O hydrogen bonds generate (100) sheets.

Related literature

For thia­zole derivatives as inhibitors for cancer cell growth, see: Schade et al. (2008 ▸). For carboxamides with synthetic and biological inter­est, see: Moreno-Fuquen et al. (2014a ▸,b ▸). For related structures, see: Zonouzi et al. (2009 ▸); Saeed et al. (2010 ▸).

Experimental

Crystal data

C10H7FN2OS

M = 222.24

Monoclinic,

a = 12.2171 (8) Å

b = 5.0741 (3) Å

c = 15.7078 (10) Å

β = 98.820 (6)°

V = 962.22 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 295 K

0.40 × 0.17 × 0.08 mm

Data collection

Rigaku Pilatus 200K diffractometer

Absorption correction: multi-scan CrystalClear; Rigaku, 2008 ▸ T min = 0.701, T max = 1.000

8722 measured reflections

2169 independent reflections

1556 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.098

S = 0.89

2169 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▸); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2006 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015019192/hb7520sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015019192/hb7520Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015019192/hb7520Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015019192/hb7520fig1.tif

The mol­ecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

x y z . DOI: 10.1107/S2056989015019192/hb7520fig2.tif

Part of the crystal structure of (I), showing the formation of hydrogen-bonded C(13) chains parallel to [31] [Symmetry code: (i) −x − , y − , −z + ].

CCDC reference: 1430605

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

C10H7FN2OS	Dx = 1.534 Mg m−3
Mr = 222.24	Melting point: 443(1) K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.2171 (8) Å	Cell parameters from 8732 reflections
b = 5.0741 (3) Å	θ = 3.3–27.5°
c = 15.7078 (10) Å	µ = 0.32 mm−1
β = 98.820 (6)°	T = 295 K
V = 962.22 (11) Å3	Plate, colourless
Z = 4	0.40 × 0.17 × 0.08 mm
F(000) = 456

Rigaku Pilatus 200K diffractometer	2169 independent reflections
Radiation source: Sealed tube_Mo	1556 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.060
profile data from ω–scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan CrystalClear; Rigaku, 2008	h = −15→15
Tmin = 0.701, Tmax = 1.000	k = −6→6
8722 measured reflections	l = −20→20

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 0.89	w = 1/[σ2(Fo2) + (0.0481P)2] where P = (Fo2 + 2Fc2)/3
2169 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
S1	0.18106 (4)	0.17354 (10)	0.85154 (3)	0.04570 (16)
F1	0.21170 (8)	0.5331 (2)	1.16166 (6)	0.0518 (3)
C1	0.30360 (13)	0.7730 (4)	1.06395 (10)	0.0358 (4)
O1	0.31999 (9)	0.5432 (3)	0.93486 (8)	0.0496 (3)
C8	0.11054 (13)	0.3206 (3)	0.92625 (10)	0.0343 (4)
N1	0.15631 (11)	0.5105 (3)	0.98371 (9)	0.0383 (3)
H1	0.1156	0.5758	1.0185	0.046*
C3	0.32638 (15)	0.8821 (4)	1.21586 (12)	0.0479 (5)
H3	0.3093	0.8492	1.2706	0.057*
N2	0.01031 (11)	0.2339 (3)	0.92704 (9)	0.0398 (3)
C2	0.28064 (13)	0.7317 (4)	1.14663 (11)	0.0380 (4)
C5	0.42365 (16)	1.1283 (4)	1.12149 (14)	0.0533 (5)
H5	0.4722	1.2635	1.1129	0.064*
C9	−0.01271 (15)	0.0323 (4)	0.86792 (11)	0.0432 (4)
H9	−0.0799	−0.0572	0.8604	0.052*
C7	0.26161 (13)	0.6006 (4)	0.98871 (10)	0.0362 (4)
C10	0.06810 (15)	−0.0259 (4)	0.82218 (11)	0.0466 (5)
H10	0.0636	−0.1565	0.7802	0.056*
C6	0.37735 (14)	0.9737 (4)	1.05305 (12)	0.0442 (4)
H6	0.3959	1.0045	0.9987	0.053*
C4	0.39778 (16)	1.0819 (4)	1.20273 (14)	0.0549 (5)
H4	0.4289	1.1864	1.2488	0.066*

	U11	U22	U33	U12	U13	U23
S1	0.0485 (3)	0.0515 (3)	0.0392 (3)	0.0029 (2)	0.01349 (19)	−0.0103 (2)
F1	0.0561 (6)	0.0604 (8)	0.0405 (6)	−0.0113 (6)	0.0126 (5)	0.0059 (5)
C1	0.0343 (8)	0.0378 (9)	0.0358 (9)	0.0023 (8)	0.0067 (6)	−0.0007 (7)
O1	0.0485 (7)	0.0616 (9)	0.0425 (7)	−0.0039 (7)	0.0198 (6)	−0.0084 (6)
C8	0.0403 (9)	0.0355 (9)	0.0279 (8)	0.0032 (7)	0.0077 (6)	0.0002 (7)
N1	0.0380 (7)	0.0433 (9)	0.0351 (7)	−0.0017 (7)	0.0109 (6)	−0.0090 (6)
C3	0.0443 (9)	0.0626 (13)	0.0361 (9)	0.0066 (9)	0.0042 (7)	−0.0049 (9)
N2	0.0415 (8)	0.0404 (8)	0.0385 (8)	−0.0017 (7)	0.0097 (6)	−0.0049 (7)
C2	0.0345 (8)	0.0425 (10)	0.0375 (9)	0.0023 (8)	0.0065 (6)	0.0019 (8)
C5	0.0442 (10)	0.0454 (12)	0.0687 (14)	−0.0062 (9)	0.0037 (9)	−0.0016 (10)
C9	0.0482 (10)	0.0382 (10)	0.0421 (10)	−0.0024 (9)	0.0037 (8)	−0.0026 (8)
C7	0.0392 (8)	0.0370 (10)	0.0335 (9)	0.0012 (8)	0.0088 (7)	0.0014 (7)
C10	0.0588 (11)	0.0410 (11)	0.0392 (10)	0.0036 (9)	0.0047 (8)	−0.0094 (8)
C6	0.0401 (9)	0.0467 (11)	0.0470 (10)	−0.0022 (8)	0.0105 (8)	0.0036 (9)
C4	0.0489 (10)	0.0569 (13)	0.0551 (12)	0.0012 (10)	−0.0045 (9)	−0.0170 (11)

S1—C10	1.716 (2)	C3—C2	1.375 (2)
S1—C8	1.7280 (16)	C3—H3	0.9300
F1—C2	1.357 (2)	N2—C9	1.381 (2)
C1—C2	1.386 (2)	C5—C6	1.380 (3)
C1—C6	1.388 (2)	C5—C4	1.381 (3)
C1—C7	1.496 (2)	C5—H5	0.9300
O1—C7	1.2223 (18)	C9—C10	1.340 (2)
C8—N2	1.303 (2)	C9—H9	0.9300
C8—N1	1.379 (2)	C10—H10	0.9300
N1—C7	1.356 (2)	C6—H6	0.9300
N1—H1	0.8600	C4—H4	0.9300
C3—C4	1.373 (3)
C10—S1—C8	88.45 (8)	C6—C5—H5	120.1
C2—C1—C6	117.07 (16)	C4—C5—H5	120.1
C2—C1—C7	123.89 (16)	C10—C9—N2	115.65 (16)
C6—C1—C7	118.82 (15)	C10—C9—H9	122.2
N2—C8—N1	121.13 (14)	N2—C9—H9	122.2
N2—C8—S1	115.33 (13)	O1—C7—N1	121.90 (16)
N1—C8—S1	123.50 (12)	O1—C7—C1	121.34 (15)
C7—N1—C8	124.02 (14)	N1—C7—C1	116.75 (14)
C7—N1—H1	118.0	C9—C10—S1	110.75 (14)
C8—N1—H1	118.0	C9—C10—H10	124.6
C4—C3—C2	118.77 (18)	S1—C10—H10	124.6
C4—C3—H3	120.6	C5—C6—C1	121.16 (18)
C2—C3—H3	120.6	C5—C6—H6	119.4
C8—N2—C9	109.78 (14)	C1—C6—H6	119.4
F1—C2—C3	117.53 (15)	C3—C4—C5	120.35 (18)
F1—C2—C1	119.71 (15)	C3—C4—H4	119.8
C3—C2—C1	122.75 (17)	C5—C4—H4	119.8
C6—C5—C4	119.88 (19)
C10—S1—C8—N2	−1.98 (14)	C8—N1—C7—O1	9.4 (3)
C10—S1—C8—N1	175.93 (15)	C8—N1—C7—C1	−170.15 (15)
N2—C8—N1—C7	177.02 (16)	C2—C1—C7—O1	−140.34 (18)
S1—C8—N1—C7	−0.8 (2)	C6—C1—C7—O1	34.1 (3)
N1—C8—N2—C9	−175.59 (15)	C2—C1—C7—N1	39.2 (2)
S1—C8—N2—C9	2.38 (19)	C6—C1—C7—N1	−146.37 (16)
C4—C3—C2—F1	179.02 (16)	N2—C9—C10—S1	0.2 (2)
C4—C3—C2—C1	0.0 (3)	C8—S1—C10—C9	0.94 (14)
C6—C1—C2—F1	−178.05 (14)	C4—C5—C6—C1	0.8 (3)
C7—C1—C2—F1	−3.6 (3)	C2—C1—C6—C5	−1.3 (3)
C6—C1—C2—C3	0.9 (3)	C7—C1—C6—C5	−176.13 (16)
C7—C1—C2—C3	175.41 (16)	C2—C3—C4—C5	−0.6 (3)
C8—N2—C9—C10	−1.6 (2)	C6—C5—C4—C3	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.86	2.11	2.944 (2)	165
C3—H3···O1ii	0.93	2.62	3.474 (2)	153

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1N2i	0.86	2.11	2.944(2)	165
C3H3O1ii	0.93	2.62	3.474(2)	153

Symmetry codes: (i) ; (ii) .