(Z)-2-Benzyl-idenebenzo[d]thia-zolo[3,2-a]imidazol-3(2H)-one.

The mol-ecule of the title compound, C(16)H(10)N(2)OS, is approximately planar, the dihedral angle between the 1,3-benzothia-zolo[3,2-a]imidazol-3(2H)-one and the benzyl-idene moieties being 4.10 (8)°. A weak intra-molecular C-H⋯S inter-action generates an S(6) ring. No inter-molecular hydrogen bonds are observed in the crystal structure.

Related literature

For background to and the biological activity of thia­zolo[3,2-a]benzimidazoles, see: Al-Rashood & Abdel-Aziz (2010 ▶); Chimirri et al. (1988 ▶), For a related structure, references to our previous work in this area and references to further synthetic details, see: Fun et al. (2012 ▶).

Experimental

Crystal data

C16H10N2OS

M = 278.32

Orthorhombic,

a = 12.1721 (5) Å

b = 7.7697 (3) Å

c = 27.2200 (8) Å

V = 2574.29 (16) Å3

Z = 8

Cu Kα radiation

μ = 2.20 mm−1

T = 296 K

0.77 × 0.65 × 0.04 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.282, T max = 0.917

8750 measured reflections

2270 independent reflections

1912 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.127

S = 1.03

2270 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035003/hb6910sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035003/hb6910Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035003/hb6910Isup3.cml

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

C16H10N2OS	F(000) = 1152
Mr = 278.32	Dx = 1.436 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1434 reflections
a = 12.1721 (5) Å	θ = 3.3–69.8°
b = 7.7697 (3) Å	µ = 2.20 mm−1
c = 27.2200 (8) Å	T = 296 K
V = 2574.29 (16) Å3	Plate, yellow
Z = 8	0.77 × 0.65 × 0.04 mm

Bruker SMART APEXII CCD diffractometer	2270 independent reflections
Radiation source: fine-focus sealed tube	1912 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
φ and ω scans	θmax = 67.4°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→14
Tmin = 0.282, Tmax = 0.917	k = −8→6
8750 measured reflections	l = −32→28

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) = 0.127	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0558P)2 + 0.7634P] where P = (Fo2 + 2Fc2)/3
2270 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.20 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 > 2sigma(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	0.78126 (4)	0.01576 (8)	0.554734 (19)	0.0518 (2)
O1	1.04329 (12)	−0.1399 (2)	0.62205 (6)	0.0608 (5)
N1	0.89265 (13)	0.0307 (2)	0.63592 (6)	0.0441 (4)
N2	0.72939 (15)	0.1641 (3)	0.64488 (7)	0.0556 (5)
C1	0.95869 (16)	−0.0762 (3)	0.60802 (7)	0.0450 (5)
C2	0.90610 (16)	−0.0989 (3)	0.55886 (7)	0.0440 (5)
C3	0.79414 (17)	0.0814 (3)	0.61580 (8)	0.0470 (5)
C4	0.78928 (17)	0.1704 (3)	0.68946 (8)	0.0488 (5)
C5	0.75984 (19)	0.2391 (3)	0.73449 (9)	0.0580 (6)
H5A	0.6924	0.2931	0.7389	0.070*
C6	0.8340 (2)	0.2249 (3)	0.77273 (8)	0.0591 (6)
H6A	0.8156	0.2700	0.8033	0.071*
C7	0.9350 (2)	0.1456 (3)	0.76682 (8)	0.0569 (6)
H7A	0.9826	0.1387	0.7935	0.068*
C8	0.96661 (18)	0.0763 (3)	0.72232 (8)	0.0506 (5)
H8A	1.0349	0.0248	0.7180	0.061*
C9	0.89105 (17)	0.0880 (3)	0.68454 (7)	0.0439 (5)
C10	0.95483 (17)	−0.1957 (3)	0.52492 (8)	0.0472 (5)
H10A	1.0213	−0.2430	0.5350	0.057*
C11	0.92361 (16)	−0.2417 (3)	0.47492 (8)	0.0460 (5)
C12	0.82753 (19)	−0.1866 (4)	0.45178 (9)	0.0592 (6)
H12A	0.7789	−0.1147	0.4683	0.071*
C13	0.8045 (2)	−0.2387 (4)	0.40425 (10)	0.0714 (7)
H13A	0.7401	−0.2021	0.3892	0.086*
C14	0.8757 (2)	−0.3439 (4)	0.37915 (9)	0.0659 (7)
H14A	0.8594	−0.3784	0.3472	0.079*
C15	0.9707 (2)	−0.3979 (4)	0.40123 (9)	0.0655 (7)
H15A	1.0197	−0.4677	0.3842	0.079*
C16	0.99336 (19)	−0.3485 (3)	0.44864 (8)	0.0554 (6)
H16A	1.0574	−0.3879	0.4635	0.066*

	U11	U22	U33	U12	U13	U23
S1	0.0486 (4)	0.0588 (4)	0.0480 (3)	0.0084 (2)	−0.0101 (2)	−0.0030 (2)
O1	0.0484 (8)	0.0820 (12)	0.0522 (9)	0.0157 (8)	−0.0082 (7)	−0.0057 (8)
N1	0.0437 (9)	0.0443 (10)	0.0442 (9)	0.0009 (7)	−0.0052 (7)	−0.0007 (7)
N2	0.0549 (10)	0.0609 (13)	0.0509 (10)	0.0135 (9)	−0.0049 (8)	−0.0033 (9)
C1	0.0437 (11)	0.0476 (12)	0.0438 (11)	−0.0019 (9)	−0.0018 (9)	0.0002 (9)
C2	0.0416 (10)	0.0465 (13)	0.0438 (11)	−0.0023 (9)	−0.0034 (8)	0.0035 (9)
C3	0.0484 (11)	0.0451 (12)	0.0474 (11)	0.0040 (9)	−0.0060 (9)	0.0031 (9)
C4	0.0530 (12)	0.0463 (13)	0.0471 (11)	0.0022 (9)	−0.0013 (9)	0.0029 (9)
C5	0.0586 (13)	0.0613 (15)	0.0542 (13)	0.0076 (11)	0.0057 (11)	−0.0022 (11)
C6	0.0708 (14)	0.0632 (16)	0.0432 (12)	−0.0013 (12)	0.0060 (10)	−0.0032 (11)
C7	0.0656 (14)	0.0616 (15)	0.0437 (12)	−0.0062 (11)	−0.0053 (10)	−0.0001 (11)
C8	0.0499 (11)	0.0527 (14)	0.0492 (11)	−0.0013 (10)	−0.0059 (9)	0.0003 (10)
C9	0.0497 (11)	0.0409 (12)	0.0413 (10)	−0.0030 (9)	0.0006 (8)	0.0001 (9)
C10	0.0449 (10)	0.0520 (13)	0.0446 (11)	0.0002 (9)	−0.0022 (9)	0.0036 (10)
C11	0.0473 (10)	0.0461 (12)	0.0446 (11)	−0.0049 (9)	−0.0009 (9)	0.0016 (9)
C12	0.0542 (12)	0.0716 (17)	0.0519 (12)	0.0081 (11)	−0.0052 (10)	−0.0082 (12)
C13	0.0661 (15)	0.090 (2)	0.0578 (15)	0.0089 (14)	−0.0158 (12)	−0.0099 (14)
C14	0.0783 (16)	0.0715 (18)	0.0478 (12)	−0.0034 (13)	−0.0079 (12)	−0.0104 (12)
C15	0.0772 (16)	0.0656 (17)	0.0538 (13)	0.0069 (13)	0.0063 (12)	−0.0083 (12)
C16	0.0544 (13)	0.0606 (15)	0.0511 (13)	0.0049 (11)	−0.0014 (10)	0.0002 (11)

S1—C3	1.746 (2)	C7—H7A	0.9300
S1—C2	1.765 (2)	C8—C9	1.383 (3)
O1—C1	1.205 (2)	C8—H8A	0.9300
N1—C3	1.376 (3)	C10—C11	1.457 (3)
N1—C1	1.383 (3)	C10—H10A	0.9300
N1—C9	1.396 (3)	C11—C16	1.386 (3)
N2—C3	1.289 (3)	C11—C12	1.396 (3)
N2—C4	1.417 (3)	C12—C13	1.384 (3)
C1—C2	1.494 (3)	C12—H12A	0.9300
C2—C10	1.331 (3)	C13—C14	1.373 (4)
C4—C5	1.384 (3)	C13—H13A	0.9300
C4—C9	1.401 (3)	C14—C15	1.369 (4)
C5—C6	1.382 (3)	C14—H14A	0.9300
C5—H5A	0.9300	C15—C16	1.374 (3)
C6—C7	1.384 (3)	C15—H15A	0.9300
C6—H6A	0.9300	C16—H16A	0.9300
C7—C8	1.380 (3)
C3—S1—C2	90.54 (10)	C7—C8—H8A	121.9
C3—N1—C1	117.37 (17)	C9—C8—H8A	121.9
C3—N1—C9	105.91 (17)	C8—C9—N1	132.4 (2)
C1—N1—C9	136.04 (18)	C8—C9—C4	123.2 (2)
C3—N2—C4	103.21 (17)	N1—C9—C4	104.39 (17)
O1—C1—N1	124.72 (19)	C2—C10—C11	132.1 (2)
O1—C1—C2	127.0 (2)	C2—C10—H10A	113.9
N1—C1—C2	108.28 (17)	C11—C10—H10A	113.9
C10—C2—C1	119.84 (19)	C16—C11—C12	117.6 (2)
C10—C2—S1	128.66 (16)	C16—C11—C10	117.96 (19)
C1—C2—S1	111.49 (15)	C12—C11—C10	124.4 (2)
N2—C3—N1	115.54 (19)	C13—C12—C11	120.1 (2)
N2—C3—S1	132.50 (16)	C13—C12—H12A	119.9
N1—C3—S1	111.95 (15)	C11—C12—H12A	119.9
C5—C4—C9	119.3 (2)	C14—C13—C12	120.7 (2)
C5—C4—N2	129.7 (2)	C14—C13—H13A	119.6
C9—C4—N2	110.95 (18)	C12—C13—H13A	119.6
C6—C5—C4	117.8 (2)	C15—C14—C13	119.8 (2)
C6—C5—H5A	121.1	C15—C14—H14A	120.1
C4—C5—H5A	121.1	C13—C14—H14A	120.1
C5—C6—C7	121.9 (2)	C14—C15—C16	119.8 (2)
C5—C6—H6A	119.1	C14—C15—H15A	120.1
C7—C6—H6A	119.1	C16—C15—H15A	120.1
C8—C7—C6	121.6 (2)	C15—C16—C11	121.9 (2)
C8—C7—H7A	119.2	C15—C16—H16A	119.0
C6—C7—H7A	119.2	C11—C16—H16A	119.0
C7—C8—C9	116.2 (2)
C3—N1—C1—O1	−174.8 (2)	C6—C7—C8—C9	−1.2 (4)
C9—N1—C1—O1	−5.8 (4)	C7—C8—C9—N1	−178.4 (2)
C3—N1—C1—C2	4.5 (3)	C7—C8—C9—C4	2.4 (3)
C9—N1—C1—C2	173.5 (2)	C3—N1—C9—C8	−179.5 (2)
O1—C1—C2—C10	−1.4 (4)	C1—N1—C9—C8	10.7 (4)
N1—C1—C2—C10	179.30 (19)	C3—N1—C9—C4	−0.1 (2)
O1—C1—C2—S1	179.0 (2)	C1—N1—C9—C4	−169.9 (2)
N1—C1—C2—S1	−0.3 (2)	C5—C4—C9—C8	−2.3 (3)
C3—S1—C2—C10	177.7 (2)	N2—C4—C9—C8	179.4 (2)
C3—S1—C2—C1	−2.71 (16)	C5—C4—C9—N1	178.3 (2)
C4—N2—C3—N1	−0.2 (3)	N2—C4—C9—N1	0.0 (2)
C4—N2—C3—S1	178.6 (2)	C1—C2—C10—C11	179.5 (2)
C1—N1—C3—N2	172.3 (2)	S1—C2—C10—C11	−1.0 (4)
C9—N1—C3—N2	0.2 (3)	C2—C10—C11—C16	−179.5 (2)
C1—N1—C3—S1	−6.8 (3)	C2—C10—C11—C12	−0.1 (4)
C9—N1—C3—S1	−178.84 (14)	C16—C11—C12—C13	0.1 (4)
C2—S1—C3—N2	−173.7 (3)	C10—C11—C12—C13	−179.3 (2)
C2—S1—C3—N1	5.20 (17)	C11—C12—C13—C14	−0.4 (5)
C3—N2—C4—C5	−178.0 (3)	C12—C13—C14—C15	−0.1 (5)
C3—N2—C4—C9	0.1 (3)	C13—C14—C15—C16	1.0 (4)
C9—C4—C5—C6	0.9 (4)	C14—C15—C16—C11	−1.3 (4)
N2—C4—C5—C6	178.8 (2)	C12—C11—C16—C15	0.8 (4)
C4—C5—C6—C7	0.2 (4)	C10—C11—C16—C15	−179.7 (2)
C5—C6—C7—C8	0.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···S1	0.93	2.56	3.262 (3)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯S1	0.93	2.56	3.262 (3)	132