7H-[1,2]Benzothia-zolo[3,2-b]quinazoline 5,5-dioxide.

In the title compound, C(14)H(10)N(2)O(2)S, the benzothia-zole and quinazoline ring systems are essentially planar with maximum deviations of 0.0127 (16) and 0.1588 (15) Å, respectively, and make a dihedral angleof 3.02 (5)°, which shows that the entire mol-ecule is almost planar. The O atoms deviate from the benzothia-zole ring system by 1.2231 (14) and -1.1989 (15) Å. The crystal packing features non-classical C-H⋯O hydrogen bonds and is further consolidated by π-π inter-actions [centroid-centroid distances = 3.7568 (8) and 3.8848 (9) Å].

Related literature

For the uses and biological importance of benzothia­zole and quinazoline derivatives, see: Schwartz et al. (1992 ▶); Wolfe et al. (1990 ▶); Tereshima et al. (1995 ▶). For related structures, see: Khan et al. (2012 ▶); Grundt et al. (2010 ▶).

Experimental

Crystal data

C14H10N2O2S

M = 270.31

Orthorhombic,

a = 7.9389 (2) Å

b = 13.1460 (4) Å

c = 22.7952 (7) Å

V = 2379.02 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 295 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.922, T max = 0.947

21710 measured reflections

2328 independent reflections

1981 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.122

S = 1.06

2328 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812040871/rk2382sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040871/rk2382Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812040871/rk2382Isup3.cml

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

C14H10N2O2S	F(000) = 1120
Mr = 270.31	Dx = 1.509 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2328 reflections
a = 7.9389 (2) Å	θ = 3.1–26.0°
b = 13.1460 (4) Å	µ = 0.27 mm−1
c = 22.7952 (7) Å	T = 295 K
V = 2379.02 (12) Å3	Block, yellow
Z = 8	0.30 × 0.25 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	2328 independent reflections
Radiation source: fine–focus sealed tube	1981 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω– & φ–scans	θmax = 26.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→6
Tmin = 0.922, Tmax = 0.947	k = −16→14
21710 measured reflections	l = −28→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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0837P)2 + 0.4043P] where P = (Fo2 + 2Fc2)/3
2328 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.0174 (2)	0.49618 (13)	0.32511 (7)	0.0390 (4)
C2	−0.0613 (2)	0.51583 (15)	0.27215 (8)	0.0506 (5)
H2	−0.0732	0.4655	0.2438	0.061*
C3	−0.1217 (3)	0.61328 (16)	0.26314 (9)	0.0556 (5)
H3	−0.1767	0.6288	0.2283	0.067*
C4	−0.1014 (2)	0.68776 (16)	0.30527 (9)	0.0532 (5)
H4	−0.1421	0.7529	0.2981	0.064*
C5	−0.0215 (2)	0.66715 (14)	0.35795 (8)	0.0447 (4)
H5	−0.0084	0.7177	0.3861	0.054*
C6	0.0382 (2)	0.56991 (12)	0.36773 (7)	0.0354 (4)
C7	0.12413 (19)	0.53087 (11)	0.42037 (7)	0.0335 (4)
C8	0.2162 (3)	0.36384 (13)	0.46019 (8)	0.0457 (4)
H8A	0.3027	0.3170	0.4471	0.055*
H8B	0.1206	0.3244	0.4738	0.055*
C9	0.2830 (2)	0.42841 (13)	0.50934 (7)	0.0365 (4)
C10	0.24723 (19)	0.53228 (12)	0.51127 (6)	0.0342 (4)
C11	0.3012 (2)	0.58936 (14)	0.55898 (7)	0.0433 (4)
H11	0.2774	0.6586	0.5605	0.052*
C12	0.3900 (2)	0.54436 (16)	0.60411 (8)	0.0497 (5)
H12	0.4248	0.5832	0.6360	0.060*
C13	0.4270 (2)	0.44222 (16)	0.60202 (8)	0.0498 (5)
H13	0.4872	0.4119	0.6323	0.060*
C14	0.3743 (2)	0.38476 (13)	0.55469 (8)	0.0449 (4)
H14	0.4004	0.3158	0.5532	0.054*
N1	0.1652 (2)	0.42909 (10)	0.41195 (6)	0.0414 (4)
N2	0.15773 (18)	0.58305 (10)	0.46603 (6)	0.0371 (3)
O1	0.24864 (17)	0.35324 (11)	0.31425 (6)	0.0575 (4)
O2	−0.01803 (19)	0.30315 (10)	0.35705 (6)	0.0581 (4)
S1	0.10439 (6)	0.38070 (3)	0.348166 (18)	0.04023 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0408 (9)	0.0411 (9)	0.0352 (9)	−0.0072 (7)	0.0019 (7)	−0.0004 (6)
C2	0.0551 (11)	0.0603 (11)	0.0363 (9)	−0.0090 (10)	−0.0058 (8)	−0.0043 (8)
C3	0.0545 (12)	0.0697 (13)	0.0425 (10)	−0.0024 (10)	−0.0114 (8)	0.0090 (9)
C4	0.0570 (12)	0.0512 (11)	0.0514 (11)	0.0031 (9)	−0.0086 (8)	0.0096 (9)
C5	0.0487 (10)	0.0390 (9)	0.0464 (9)	0.0016 (8)	−0.0060 (8)	0.0006 (7)
C6	0.0359 (8)	0.0360 (8)	0.0343 (8)	−0.0053 (7)	0.0003 (6)	0.0003 (6)
C7	0.0338 (8)	0.0296 (7)	0.0373 (8)	−0.0023 (6)	0.0014 (6)	−0.0002 (6)
C8	0.0606 (11)	0.0329 (8)	0.0436 (9)	0.0040 (8)	−0.0039 (8)	0.0006 (7)
C9	0.0351 (8)	0.0373 (8)	0.0370 (8)	0.0003 (7)	0.0051 (6)	0.0029 (6)
C10	0.0322 (8)	0.0360 (8)	0.0345 (8)	−0.0005 (7)	0.0016 (6)	0.0005 (6)
C11	0.0472 (10)	0.0428 (9)	0.0401 (9)	−0.0004 (8)	−0.0019 (7)	−0.0042 (7)
C12	0.0515 (11)	0.0588 (12)	0.0387 (9)	−0.0042 (9)	−0.0051 (8)	−0.0030 (8)
C13	0.0481 (10)	0.0595 (12)	0.0418 (9)	0.0005 (9)	−0.0062 (8)	0.0107 (8)
C14	0.0456 (10)	0.0424 (10)	0.0468 (10)	0.0029 (8)	0.0014 (8)	0.0085 (7)
N1	0.0576 (9)	0.0303 (7)	0.0362 (7)	0.0016 (7)	−0.0044 (6)	−0.0028 (5)
N2	0.0417 (7)	0.0335 (7)	0.0363 (7)	0.0022 (6)	−0.0034 (6)	−0.0021 (5)
O1	0.0659 (9)	0.0564 (8)	0.0501 (8)	0.0070 (7)	0.0156 (6)	−0.0062 (6)
O2	0.0750 (10)	0.0423 (7)	0.0570 (8)	−0.0208 (7)	0.0046 (7)	−0.0050 (6)
S1	0.0516 (3)	0.0345 (3)	0.0346 (3)	−0.00603 (18)	0.00492 (17)	−0.00507 (14)

C1—C6	1.382 (2)	C8—H8A	0.9700
C1—C2	1.384 (2)	C8—H8B	0.9700
C1—S1	1.7485 (18)	C9—C14	1.387 (2)
C2—C3	1.383 (3)	C9—C10	1.395 (2)
C2—H2	0.9300	C10—C11	1.389 (2)
C3—C4	1.381 (3)	C10—N2	1.419 (2)
C3—H3	0.9300	C11—C12	1.380 (3)
C4—C5	1.384 (2)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.375 (3)
C5—C6	1.382 (2)	C12—H12	0.9300
C5—H5	0.9300	C13—C14	1.382 (3)
C6—C7	1.473 (2)	C13—H13	0.9300
C7—N2	1.275 (2)	C14—H14	0.9300
C7—N1	1.390 (2)	N1—S1	1.6589 (14)
C8—N1	1.452 (2)	O1—S1	1.4281 (13)
C8—C9	1.502 (2)	O2—S1	1.4230 (13)
C6—C1—C2	122.42 (17)	C14—C9—C8	120.43 (16)
C6—C1—S1	110.51 (12)	C10—C9—C8	120.31 (14)
C2—C1—S1	127.06 (14)	C11—C10—C9	119.36 (15)
C3—C2—C1	117.32 (18)	C11—C10—N2	118.00 (14)
C3—C2—H2	121.3	C9—C10—N2	122.63 (14)
C1—C2—H2	121.3	C12—C11—C10	120.64 (17)
C2—C3—C4	120.86 (18)	C12—C11—H11	119.7
C2—C3—H3	119.6	C10—C11—H11	119.7
C4—C3—H3	119.6	C13—C12—C11	120.12 (17)
C3—C4—C5	121.19 (18)	C13—C12—H12	119.9
C3—C4—H4	119.4	C11—C12—H12	119.9
C5—C4—H4	119.4	C12—C13—C14	119.74 (16)
C6—C5—C4	118.57 (17)	C12—C13—H13	120.1
C6—C5—H5	120.7	C14—C13—H13	120.1
C4—C5—H5	120.7	C13—C14—C9	120.93 (16)
C1—C6—C5	119.62 (15)	C13—C14—H14	119.5
C1—C6—C7	112.56 (14)	C9—C14—H14	119.5
C5—C6—C7	127.81 (15)	C7—N1—C8	121.96 (13)
N2—C7—N1	125.55 (14)	C7—N1—S1	114.95 (11)
N2—C7—C6	125.08 (14)	C8—N1—S1	121.22 (11)
N1—C7—C6	109.36 (13)	C7—N2—C10	116.43 (13)
N1—C8—C9	109.23 (14)	O2—S1—O1	116.34 (9)
N1—C8—H8A	109.8	O2—S1—N1	110.41 (8)
C9—C8—H8A	109.8	O1—S1—N1	109.76 (8)
N1—C8—H8B	109.8	O2—S1—C1	113.27 (9)
C9—C8—H8B	109.8	O1—S1—C1	111.92 (8)
H8A—C8—H8B	108.3	N1—S1—C1	92.60 (7)
C14—C9—C10	119.20 (15)
C6—C1—C2—C3	−0.7 (3)	C12—C13—C14—C9	−0.6 (3)
S1—C1—C2—C3	179.80 (15)	C10—C9—C14—C13	1.3 (3)
C1—C2—C3—C4	0.9 (3)	C8—C9—C14—C13	−175.78 (16)
C2—C3—C4—C5	−0.6 (3)	N2—C7—N1—C8	15.1 (3)
C3—C4—C5—C6	0.1 (3)	C6—C7—N1—C8	−165.98 (16)
C2—C1—C6—C5	0.2 (3)	N2—C7—N1—S1	179.66 (14)
S1—C1—C6—C5	179.80 (13)	C6—C7—N1—S1	−1.41 (17)
C2—C1—C6—C7	179.50 (15)	C9—C8—N1—C7	−22.8 (2)
S1—C1—C6—C7	−0.94 (18)	C9—C8—N1—S1	173.54 (12)
C4—C5—C6—C1	0.1 (3)	N1—C7—N2—C10	1.1 (2)
C4—C5—C6—C7	−179.04 (16)	C6—C7—N2—C10	−177.62 (13)
C1—C6—C7—N2	−179.58 (16)	C11—C10—N2—C7	173.48 (15)
C5—C6—C7—N2	−0.4 (3)	C9—C10—N2—C7	−6.2 (2)
C1—C6—C7—N1	1.48 (19)	C7—N1—S1—O2	−115.25 (13)
C5—C6—C7—N1	−179.33 (16)	C8—N1—S1—O2	49.45 (17)
N1—C8—C9—C14	−165.40 (15)	C7—N1—S1—O1	115.20 (13)
N1—C8—C9—C10	17.6 (2)	C8—N1—S1—O1	−80.10 (16)
C14—C9—C10—C11	−1.1 (2)	C7—N1—S1—C1	0.78 (14)
C8—C9—C10—C11	175.98 (16)	C8—N1—S1—C1	165.48 (15)
C14—C9—C10—N2	178.63 (15)	C6—C1—S1—O2	113.68 (13)
C8—C9—C10—N2	−4.3 (2)	C2—C1—S1—O2	−66.78 (18)
C9—C10—C11—C12	0.2 (3)	C6—C1—S1—O1	−112.40 (13)
N2—C10—C11—C12	−179.50 (15)	C2—C1—S1—O1	67.14 (18)
C10—C11—C12—C13	0.5 (3)	C6—C1—S1—N1	0.13 (14)
C11—C12—C13—C14	−0.3 (3)	C2—C1—S1—N1	179.66 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.43	3.275 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.43	3.275 (2)	150

Symmetry code: (i) .