3-Fluoro-12H-benzimidazo[2,1-b][1,3]benzothia-zin-12-one.

In the title compound, C(14)H(7)FN(2)OS, prepared by the reaction of 2-bromo-4-fluoro-benzoyl choride with 2-mercaptobenzimidazole, the four-membered fused-ring system is essentially planar [maximum deviation from the mean plane = 0.035 (2) Å]. The crystal packing is stabilized by weak inter-molecular π-π [minimum ring centroid-centroid separation = 3.509 (7) Å], weak C-F⋯π [F⋯centroid = 3.4464 (17) Å, C-F⋯centroid = 97.72 (11)°] and C-O⋯π [O⋯centroid = 3.5230 (16) and 3.7296 (17) Å, C-O⋯centroid = 86.40 (10) and 86.25 (10)°] inter-actions and weak inter-molecular C-H⋯N hydrogen bonds.

Related literature

For general background to spiranes, see: Dawood & Abdel-Wahab (2010 ▶); Dolbier et al. (1994 ▶); Mavrova et al. (2010 ▶); Sekar et al. (2011 ▶).

Experimental

Crystal data

C14H7FN2OS

M = 270.28

Monoclinic,

a = 9.5027 (12) Å

b = 7.0759 (9) Å

c = 16.931 (2) Å

β = 94.375 (3)°

V = 1135.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.20 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.944, T max = 0.958

5987 measured reflections

1989 independent reflections

1772 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.106

S = 1.00

1989 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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) I, global. DOI: 10.1107/S1600536811054948/ds2160sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054948/ds2160Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811054948/ds2160Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H7FN2OS	F(000) = 552
Mr = 270.28	Dx = 1.582 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3848 reflections
a = 9.5027 (12) Å	θ = 2.4–29.8°
b = 7.0759 (9) Å	µ = 0.29 mm−1
c = 16.931 (2) Å	T = 293 K
β = 94.375 (3)°	Block, colourless
V = 1135.1 (2) Å3	0.20 × 0.18 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1989 independent reflections
Radiation source: fine-focus sealed tube	1772 reflections with I > 2σ(I)
graphite	Rint = 0.031
phi and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→11
Tmin = 0.944, Tmax = 0.958	k = −8→8
5987 measured reflections	l = −20→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0611P)2 + 0.4006P] where P = (Fo2 + 2Fc2)/3
1989 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.33 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
S1	−0.14487 (5)	0.16939 (8)	0.36622 (3)	0.0538 (2)
F1	−0.43167 (13)	0.1082 (2)	0.59933 (8)	0.0691 (4)
O1	0.19345 (15)	0.3338 (2)	0.54945 (8)	0.0550 (4)
N1	0.08266 (18)	0.2319 (2)	0.28889 (9)	0.0512 (4)
N2	0.12490 (15)	0.2778 (2)	0.42060 (8)	0.0386 (3)
C1	0.4856 (2)	0.4053 (3)	0.36667 (13)	0.0549 (5)
H1	0.5742	0.4478	0.3860	0.066*
C2	0.3838 (2)	0.3749 (3)	0.41907 (12)	0.0478 (4)
H2	0.4024	0.3929	0.4733	0.057*
C3	0.2520 (2)	0.3161 (2)	0.38695 (11)	0.0409 (4)
C4	0.2239 (2)	0.2870 (3)	0.30570 (11)	0.0458 (4)
C5	0.3284 (2)	0.3134 (3)	0.25403 (12)	0.0570 (5)
H5	0.3112	0.2914	0.2000	0.068*
C6	0.4596 (2)	0.3741 (3)	0.28586 (13)	0.0600 (5)
H6	0.5314	0.3942	0.2525	0.072*
C7	0.0288 (2)	0.2291 (2)	0.35679 (10)	0.0429 (4)
C8	0.0987 (2)	0.2875 (2)	0.50112 (10)	0.0404 (4)
C9	−0.04393 (18)	0.2395 (2)	0.52280 (10)	0.0387 (4)
C10	−0.1557 (2)	0.1855 (2)	0.46872 (11)	0.0420 (4)
C11	−0.2867 (2)	0.1387 (3)	0.49526 (12)	0.0474 (5)
H11	−0.3609	0.0999	0.4599	0.057*
C12	−0.3033 (2)	0.1512 (3)	0.57463 (12)	0.0496 (5)
C13	−0.1972 (2)	0.2037 (3)	0.62965 (12)	0.0517 (5)
H13	−0.2121	0.2090	0.6833	0.062*
C14	−0.0687 (2)	0.2480 (3)	0.60323 (11)	0.0446 (4)
H14	0.0043	0.2848	0.6397	0.054*

	U11	U22	U33	U12	U13	U23
S1	0.0482 (3)	0.0744 (4)	0.0365 (3)	−0.0045 (2)	−0.0113 (2)	−0.0035 (2)
F1	0.0542 (7)	0.0824 (9)	0.0723 (8)	−0.0065 (6)	0.0150 (6)	−0.0017 (7)
O1	0.0544 (8)	0.0695 (9)	0.0387 (7)	−0.0113 (7)	−0.0121 (6)	−0.0058 (6)
N1	0.0585 (10)	0.0611 (10)	0.0325 (8)	0.0036 (8)	−0.0060 (7)	0.0026 (7)
N2	0.0429 (8)	0.0397 (8)	0.0319 (7)	0.0020 (6)	−0.0068 (6)	−0.0009 (6)
C1	0.0490 (11)	0.0546 (11)	0.0610 (12)	0.0014 (9)	0.0031 (9)	0.0037 (9)
C2	0.0474 (10)	0.0477 (10)	0.0475 (10)	0.0006 (8)	−0.0014 (8)	−0.0001 (8)
C3	0.0469 (10)	0.0344 (8)	0.0407 (9)	0.0051 (7)	−0.0021 (8)	0.0031 (7)
C4	0.0537 (11)	0.0430 (9)	0.0399 (10)	0.0074 (8)	−0.0024 (8)	0.0059 (8)
C5	0.0690 (14)	0.0596 (12)	0.0425 (11)	0.0118 (10)	0.0046 (10)	0.0067 (9)
C6	0.0596 (13)	0.0646 (13)	0.0573 (13)	0.0074 (10)	0.0135 (10)	0.0108 (10)
C7	0.0491 (10)	0.0412 (9)	0.0362 (9)	0.0041 (8)	−0.0105 (7)	0.0007 (7)
C8	0.0480 (10)	0.0377 (9)	0.0341 (9)	0.0022 (7)	−0.0070 (7)	−0.0009 (7)
C9	0.0448 (10)	0.0336 (8)	0.0365 (9)	0.0050 (7)	−0.0052 (7)	0.0002 (7)
C10	0.0488 (10)	0.0368 (9)	0.0389 (9)	0.0059 (7)	−0.0066 (8)	0.0012 (7)
C11	0.0431 (10)	0.0449 (10)	0.0525 (11)	0.0021 (8)	−0.0075 (8)	0.0003 (8)
C12	0.0473 (11)	0.0447 (10)	0.0572 (12)	0.0039 (8)	0.0069 (9)	0.0030 (8)
C13	0.0619 (12)	0.0507 (11)	0.0425 (10)	0.0065 (9)	0.0053 (9)	−0.0003 (8)
C14	0.0507 (10)	0.0443 (9)	0.0378 (9)	0.0050 (8)	−0.0046 (8)	−0.0012 (7)

S1—C7	1.723 (2)	C4—C5	1.385 (3)
S1—C10	1.7501 (19)	C5—C6	1.388 (3)
F1—C12	1.354 (2)	C5—H5	0.9300
O1—C8	1.214 (2)	C6—H6	0.9300
N1—C7	1.294 (2)	C8—C9	1.471 (3)
N1—C4	1.406 (3)	C9—C10	1.402 (2)
N2—C3	1.401 (2)	C9—C14	1.401 (2)
N2—C7	1.403 (2)	C10—C11	1.395 (3)
N2—C8	1.406 (2)	C11—C12	1.368 (3)
C1—C2	1.378 (3)	C11—H11	0.9300
C1—C6	1.389 (3)	C12—C13	1.371 (3)
C1—H1	0.9300	C13—C14	1.369 (3)
C2—C3	1.390 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.397 (3)
C7—S1—C10	101.85 (9)	N1—C7—S1	122.20 (14)
C7—N1—C4	105.11 (16)	N2—C7—S1	124.09 (14)
C3—N2—C7	105.38 (14)	O1—C8—N2	119.32 (17)
C3—N2—C8	127.34 (15)	O1—C8—C9	122.96 (16)
C7—N2—C8	127.28 (15)	N2—C8—C9	117.72 (15)
C2—C1—C6	121.9 (2)	C10—C9—C14	118.16 (17)
C2—C1—H1	119.1	C10—C9—C8	124.53 (16)
C6—C1—H1	119.1	C14—C9—C8	117.31 (16)
C1—C2—C3	116.76 (19)	C11—C10—C9	120.31 (17)
C1—C2—H2	121.6	C11—C10—S1	115.18 (14)
C3—C2—H2	121.6	C9—C10—S1	124.51 (15)
C2—C3—C4	121.90 (18)	C12—C11—C10	118.25 (18)
C2—C3—N2	132.68 (17)	C12—C11—H11	120.9
C4—C3—N2	105.41 (16)	C10—C11—H11	120.9
C5—C4—C3	120.66 (19)	F1—C12—C13	118.95 (18)
C5—C4—N1	128.96 (19)	F1—C12—C11	117.57 (18)
C3—C4—N1	110.38 (17)	C13—C12—C11	123.47 (19)
C4—C5—C6	117.5 (2)	C12—C13—C14	117.93 (19)
C4—C5—H5	121.2	C12—C13—H13	121.0
C6—C5—H5	121.2	C14—C13—H13	121.0
C5—C6—C1	121.2 (2)	C13—C14—C9	121.85 (18)
C5—C6—H6	119.4	C13—C14—H14	119.1
C1—C6—H6	119.4	C9—C14—H14	119.1
N1—C7—N2	113.71 (17)
C6—C1—C2—C3	−1.7 (3)	C10—S1—C7—N2	−0.75 (17)
C1—C2—C3—C4	0.7 (3)	C3—N2—C8—O1	0.0 (3)
C1—C2—C3—N2	−177.85 (18)	C7—N2—C8—O1	−179.37 (17)
C7—N2—C3—C2	178.39 (19)	C3—N2—C8—C9	−179.66 (15)
C8—N2—C3—C2	−1.1 (3)	C7—N2—C8—C9	0.9 (2)
C7—N2—C3—C4	−0.31 (18)	O1—C8—C9—C10	180.00 (17)
C8—N2—C3—C4	−179.83 (15)	N2—C8—C9—C10	−0.3 (2)
C2—C3—C4—C5	1.0 (3)	O1—C8—C9—C14	−0.2 (3)
N2—C3—C4—C5	179.83 (16)	N2—C8—C9—C14	179.46 (15)
C2—C3—C4—N1	−178.82 (16)	C14—C9—C10—C11	−1.1 (2)
N2—C3—C4—N1	0.06 (19)	C8—C9—C10—C11	178.63 (16)
C7—N1—C4—C5	−179.51 (19)	C14—C9—C10—S1	179.32 (13)
C7—N1—C4—C3	0.2 (2)	C8—C9—C10—S1	−0.9 (2)
C3—C4—C5—C6	−1.6 (3)	C7—S1—C10—C11	−178.27 (13)
N1—C4—C5—C6	178.15 (19)	C7—S1—C10—C9	1.29 (17)
C4—C5—C6—C1	0.6 (3)	C9—C10—C11—C12	1.5 (3)
C2—C1—C6—C5	1.0 (3)	S1—C10—C11—C12	−178.94 (14)
C4—N1—C7—N2	−0.5 (2)	C10—C11—C12—F1	178.98 (16)
C4—N1—C7—S1	179.82 (13)	C10—C11—C12—C13	−1.4 (3)
C3—N2—C7—N1	0.5 (2)	F1—C12—C13—C14	−179.48 (17)
C8—N2—C7—N1	−179.97 (16)	C11—C12—C13—C14	0.9 (3)
C3—N2—C7—S1	−179.78 (13)	C12—C13—C14—C9	−0.5 (3)
C8—N2—C7—S1	−0.3 (2)	C10—C9—C14—C13	0.6 (3)
C10—S1—C7—N1	178.93 (15)	C8—C9—C14—C13	−179.15 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···N1i	0.93	2.58	3.359 (2)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯N1i	0.93	2.58	3.359 (2)	141

Symmetry code: (i) .