1,3-Bis(2-quinolylcarbon-yl)-1H,3H-2,1,3-benzothia-diazole 2-oxide.

In the title compound, C(26)H(16)N(4)O(3)S, the thia-diazole ring adopts an envelope conformation, with the S atom occupying the flap position. The dihedral angle between the two quinoline ring systems is 55.32 (8)°. In the crystal, the mol-ecules are linked into chains along [010] by C-H⋯O hydrogen bonds. The chains are connected via π-π inter-actions involving one of the pyridine rings [centroid-centroid distance = 3.5558 (18) Å].

Related literature

For benzothia­diazole derivatives as potential anti­depressants, see: Pullar et al. (2000 ▶).

Experimental

Crystal data

C26H16N4O3S

M = 464.49

Triclinic,

a = 8.0914 (5) Å

b = 10.2920 (6) Å

c = 12.8843 (7) Å

α = 93.232 (2)°

β = 93.791 (2)°

γ = 101.746 (2)°

V = 1045.51 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 153 K

0.26 × 0.18 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: none

10347 measured reflections

4764 independent reflections

3074 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.189

S = 1.01

4764 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.66 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033182/ci2890sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033182/ci2890Isup2.hkl

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

C26H16N4O3S	Z = 2
Mr = 464.49	F(000) = 480
Triclinic, P1	Dx = 1.475 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0914 (5) Å	Cell parameters from 6929 reflections
b = 10.2920 (6) Å	θ = 3.1–27.5°
c = 12.8843 (7) Å	µ = 0.20 mm−1
α = 93.232 (2)°	T = 153 K
β = 93.791 (2)°	Block, white
γ = 101.746 (2)°	0.26 × 0.18 × 0.12 mm
V = 1045.51 (11) Å3

Rigaku R-AXIS RAPID diffractometer	3074 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
graphite	θmax = 27.5°, θmin = 3.1°
ω scans	h = −10→10
10347 measured reflections	k = −13→13
4764 independent reflections	l = −16→16

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.1P)2 + 0.398P] where P = (Fo2 + 2Fc2)/3
4764 reflections	(Δ/σ)max = 0.001
307 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.66 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	0.69178 (9)	0.31618 (7)	0.73387 (5)	0.0259 (2)
N1	0.6436 (3)	0.1832 (2)	0.81493 (19)	0.0270 (5)
N2	0.7768 (3)	0.2062 (2)	0.6523 (2)	0.0307 (6)
N3	0.4869 (3)	0.3845 (2)	0.86504 (18)	0.0247 (5)
N4	0.7299 (3)	0.4345 (2)	0.56732 (19)	0.0298 (6)
O1	0.8377 (2)	0.40615 (19)	0.78560 (15)	0.0294 (5)
O2	0.4360 (3)	0.0432 (2)	0.89052 (18)	0.0361 (5)
O3	0.8451 (3)	0.1354 (2)	0.49310 (17)	0.0419 (6)
C1	0.7478 (4)	0.0898 (3)	0.8014 (2)	0.0286 (6)
C2	0.7825 (4)	−0.0001 (3)	0.8718 (2)	0.0323 (7)
H2	0.7318	−0.0064	0.9362	0.039*
C3	0.8936 (4)	−0.0807 (3)	0.8452 (3)	0.0358 (7)
H3	0.9189	−0.1434	0.8919	0.043*
C4	0.9685 (4)	−0.0710 (3)	0.7510 (3)	0.0349 (7)
H4	1.0437	−0.1274	0.7342	0.042*
C5	0.9345 (4)	0.0204 (3)	0.6810 (2)	0.0340 (7)
H5	0.9867	0.0278	0.6171	0.041*
C6	0.8234 (4)	0.0996 (3)	0.7071 (2)	0.0292 (6)
C7	0.4910 (3)	0.1526 (3)	0.8607 (2)	0.0250 (6)
C8	0.3985 (3)	0.2634 (3)	0.8743 (2)	0.0254 (6)
C9	0.2277 (3)	0.2344 (3)	0.8967 (2)	0.0273 (6)
H9	0.1702	0.1455	0.9033	0.033*
C10	0.1467 (4)	0.3382 (3)	0.9088 (2)	0.0285 (6)
H10	0.0309	0.3219	0.9232	0.034*
C11	0.1604 (4)	0.5824 (3)	0.9083 (2)	0.0298 (6)
H11	0.0446	0.5719	0.9218	0.036*
C12	0.2545 (4)	0.7056 (3)	0.8968 (2)	0.0342 (7)
H12	0.2034	0.7807	0.9033	0.041*
C13	0.4257 (4)	0.7242 (3)	0.8756 (2)	0.0327 (7)
H13	0.4882	0.8111	0.8671	0.039*
C14	0.5021 (4)	0.6186 (3)	0.8672 (2)	0.0299 (6)
H14	0.6184	0.6318	0.8543	0.036*
C15	0.4078 (3)	0.4884 (3)	0.8777 (2)	0.0253 (6)
C16	0.2359 (4)	0.4696 (3)	0.8999 (2)	0.0267 (6)
C17	0.8056 (4)	0.2214 (3)	0.5479 (2)	0.0321 (7)
C18	0.7883 (4)	0.3522 (3)	0.5066 (2)	0.0291 (6)
C19	0.8409 (4)	0.3778 (3)	0.4052 (2)	0.0369 (7)
H19	0.8819	0.3140	0.3636	0.044*
C20	0.8294 (4)	0.5000 (4)	0.3707 (2)	0.0392 (8)
H20	0.8667	0.5233	0.3045	0.047*
C21	0.7451 (4)	0.7167 (3)	0.4011 (3)	0.0414 (8)
H21	0.7778	0.7432	0.3347	0.050*
C22	0.6821 (4)	0.8002 (3)	0.4645 (3)	0.0442 (9)
H22	0.6720	0.8850	0.4425	0.053*
C23	0.6310 (4)	0.7630 (3)	0.5634 (3)	0.0423 (8)
H23	0.5855	0.8223	0.6070	0.051*
C24	0.6469 (4)	0.6424 (3)	0.5963 (2)	0.0355 (7)
H24	0.6134	0.6179	0.6629	0.043*
C25	0.7126 (4)	0.5542 (3)	0.5320 (2)	0.0299 (6)
C26	0.7633 (4)	0.5896 (3)	0.4320 (2)	0.0344 (7)

	U11	U22	U33	U12	U13	U23
S1	0.0268 (4)	0.0243 (4)	0.0281 (4)	0.0063 (3)	0.0061 (3)	0.0076 (3)
N1	0.0305 (13)	0.0221 (11)	0.0321 (12)	0.0105 (10)	0.0093 (10)	0.0068 (10)
N2	0.0303 (13)	0.0303 (13)	0.0349 (13)	0.0104 (11)	0.0086 (10)	0.0097 (11)
N3	0.0255 (12)	0.0234 (11)	0.0259 (11)	0.0055 (9)	0.0035 (9)	0.0060 (10)
N4	0.0307 (13)	0.0310 (13)	0.0278 (12)	0.0042 (11)	0.0046 (10)	0.0080 (11)
O1	0.0271 (10)	0.0271 (10)	0.0329 (11)	0.0024 (8)	0.0023 (8)	0.0043 (9)
O2	0.0350 (12)	0.0281 (11)	0.0502 (13)	0.0108 (9)	0.0157 (10)	0.0154 (10)
O3	0.0513 (15)	0.0421 (13)	0.0348 (12)	0.0150 (12)	0.0085 (10)	−0.0010 (11)
C1	0.0259 (14)	0.0245 (13)	0.0377 (16)	0.0083 (12)	0.0047 (12)	0.0066 (12)
C2	0.0326 (16)	0.0296 (15)	0.0371 (16)	0.0085 (13)	0.0073 (13)	0.0090 (13)
C3	0.0306 (16)	0.0295 (15)	0.0498 (19)	0.0100 (13)	0.0035 (14)	0.0105 (14)
C4	0.0290 (15)	0.0278 (15)	0.0503 (19)	0.0118 (13)	0.0043 (14)	0.0016 (14)
C5	0.0297 (16)	0.0356 (16)	0.0382 (16)	0.0093 (13)	0.0062 (13)	0.0026 (14)
C6	0.0277 (15)	0.0275 (14)	0.0345 (15)	0.0091 (12)	0.0053 (12)	0.0063 (13)
C7	0.0281 (14)	0.0216 (13)	0.0271 (13)	0.0076 (11)	0.0053 (11)	0.0045 (11)
C8	0.0264 (14)	0.0266 (14)	0.0242 (13)	0.0059 (11)	0.0031 (11)	0.0072 (12)
C9	0.0271 (14)	0.0262 (14)	0.0294 (14)	0.0051 (11)	0.0046 (11)	0.0075 (12)
C10	0.0251 (14)	0.0319 (15)	0.0294 (14)	0.0055 (12)	0.0057 (11)	0.0086 (12)
C11	0.0307 (15)	0.0294 (14)	0.0306 (14)	0.0102 (12)	0.0013 (12)	0.0006 (13)
C12	0.0387 (17)	0.0276 (15)	0.0387 (17)	0.0135 (13)	0.0001 (13)	0.0023 (13)
C13	0.0360 (16)	0.0255 (14)	0.0374 (16)	0.0078 (12)	0.0000 (13)	0.0071 (13)
C14	0.0299 (15)	0.0306 (15)	0.0286 (14)	0.0035 (12)	0.0014 (11)	0.0083 (13)
C15	0.0283 (14)	0.0266 (13)	0.0224 (13)	0.0075 (11)	0.0028 (11)	0.0065 (11)
C16	0.0287 (14)	0.0289 (14)	0.0238 (13)	0.0086 (12)	0.0026 (11)	0.0046 (12)
C17	0.0327 (16)	0.0346 (16)	0.0301 (15)	0.0079 (13)	0.0076 (12)	0.0031 (13)
C18	0.0268 (14)	0.0332 (15)	0.0250 (14)	0.0007 (12)	0.0018 (11)	0.0040 (13)
C19	0.0360 (17)	0.0472 (19)	0.0272 (15)	0.0071 (15)	0.0033 (13)	0.0041 (15)
C20	0.0341 (17)	0.055 (2)	0.0279 (15)	0.0038 (15)	0.0054 (13)	0.0157 (16)
C21	0.0404 (18)	0.0418 (18)	0.0382 (17)	−0.0024 (15)	−0.0037 (14)	0.0174 (16)
C22	0.0432 (19)	0.0295 (16)	0.055 (2)	−0.0025 (14)	−0.0107 (16)	0.0165 (17)
C23	0.0421 (19)	0.0340 (17)	0.051 (2)	0.0087 (15)	−0.0011 (15)	0.0038 (16)
C24	0.0359 (17)	0.0356 (16)	0.0342 (16)	0.0041 (14)	0.0030 (13)	0.0074 (14)
C25	0.0263 (14)	0.0319 (15)	0.0288 (14)	−0.0008 (12)	−0.0001 (11)	0.0075 (13)
C26	0.0283 (15)	0.0415 (17)	0.0300 (15)	−0.0020 (13)	−0.0010 (12)	0.0123 (14)

S1—O1	1.441 (2)	C10—H10	0.95
S1—N1	1.764 (2)	C11—C12	1.361 (4)
S1—N2	1.771 (3)	C11—C16	1.420 (4)
N1—C7	1.390 (3)	C11—H11	0.95
N1—C1	1.413 (3)	C12—C13	1.407 (4)
N2—C17	1.393 (4)	C12—H12	0.95
N2—C6	1.437 (3)	C13—C14	1.359 (4)
N3—C8	1.321 (3)	C13—H13	0.95
N3—C15	1.361 (3)	C14—C15	1.419 (4)
N4—C18	1.300 (4)	C14—H14	0.95
N4—C25	1.368 (3)	C15—C16	1.416 (4)
O2—C7	1.217 (3)	C17—C18	1.504 (4)
O3—C17	1.208 (4)	C18—C19	1.422 (4)
C1—C2	1.388 (4)	C19—C20	1.376 (5)
C1—C6	1.396 (4)	C19—H19	0.95
C2—C3	1.388 (4)	C20—C26	1.391 (5)
C2—H2	0.95	C20—H20	0.95
C3—C4	1.391 (5)	C21—C22	1.349 (5)
C3—H3	0.95	C21—C26	1.422 (4)
C4—C5	1.393 (4)	C21—H21	0.95
C4—H4	0.95	C22—C23	1.415 (5)
C5—C6	1.376 (4)	C22—H22	0.95
C5—H5	0.95	C23—C24	1.362 (4)
C7—C8	1.495 (4)	C23—H23	0.95
C8—C9	1.406 (4)	C24—C25	1.400 (4)
C9—C10	1.369 (4)	C24—H24	0.95
C9—H9	0.95	C25—C26	1.422 (4)
C10—C16	1.412 (4)
O1—S1—N1	105.89 (12)	C11—C12—H12	119.3
O1—S1—N2	104.62 (12)	C13—C12—H12	119.3
N1—S1—N2	86.41 (10)	C14—C13—C12	120.4 (3)
C7—N1—C1	122.2 (2)	C14—C13—H13	119.8
C7—N1—S1	122.68 (17)	C12—C13—H13	119.8
C1—N1—S1	112.25 (17)	C13—C14—C15	119.8 (3)
C17—N2—C6	122.0 (3)	C13—C14—H14	120.1
C17—N2—S1	125.42 (19)	C15—C14—H14	120.1
C6—N2—S1	112.54 (19)	N3—C15—C16	121.9 (2)
C8—N3—C15	118.0 (2)	N3—C15—C14	118.2 (2)
C18—N4—C25	118.8 (2)	C16—C15—C14	119.9 (2)
C2—C1—C6	121.0 (3)	C10—C16—C15	117.9 (2)
C2—C1—N1	126.8 (3)	C10—C16—C11	123.4 (3)
C6—C1—N1	112.2 (2)	C15—C16—C11	118.7 (3)
C3—C2—C1	118.0 (3)	O3—C17—N2	122.2 (3)
C3—C2—H2	121.0	O3—C17—C18	121.2 (3)
C1—C2—H2	121.0	N2—C17—C18	116.6 (3)
C2—C3—C4	120.9 (3)	N4—C18—C19	125.0 (3)
C2—C3—H3	119.5	N4—C18—C17	117.4 (2)
C4—C3—H3	119.5	C19—C18—C17	117.6 (3)
C3—C4—C5	120.9 (3)	C20—C19—C18	116.5 (3)
C3—C4—H4	119.6	C20—C19—H19	121.8
C5—C4—H4	119.6	C18—C19—H19	121.8
C6—C5—C4	118.2 (3)	C19—C20—C26	120.4 (3)
C6—C5—H5	120.9	C19—C20—H20	119.8
C4—C5—H5	120.9	C26—C20—H20	119.8
C5—C6—C1	121.1 (2)	C22—C21—C26	121.0 (3)
C5—C6—N2	128.8 (3)	C22—C21—H21	119.5
C1—C6—N2	110.0 (2)	C26—C21—H21	119.5
O2—C7—N1	122.7 (2)	C21—C22—C23	120.8 (3)
O2—C7—C8	121.1 (2)	C21—C22—H22	119.6
N1—C7—C8	116.2 (2)	C23—C22—H22	119.6
N3—C8—C9	124.4 (2)	C24—C23—C22	120.1 (3)
N3—C8—C7	116.1 (2)	C24—C23—H23	120.0
C9—C8—C7	119.5 (2)	C22—C23—H23	120.0
C10—C9—C8	118.0 (2)	C23—C24—C25	120.2 (3)
C10—C9—H9	121.0	C23—C24—H24	119.9
C8—C9—H9	121.0	C25—C24—H24	119.9
C9—C10—C16	119.8 (2)	N4—C25—C24	119.1 (2)
C9—C10—H10	120.1	N4—C25—C26	120.4 (3)
C16—C10—H10	120.1	C24—C25—C26	120.4 (3)
C12—C11—C16	119.8 (3)	C20—C26—C21	123.6 (3)
C12—C11—H11	120.1	C20—C26—C25	118.9 (3)
C16—C11—H11	120.1	C21—C26—C25	117.5 (3)
C11—C12—C13	121.4 (3)
O1—S1—N1—C7	118.1 (2)	C12—C13—C14—C15	1.3 (5)
N2—S1—N1—C7	−137.7 (3)	C8—N3—C15—C16	−0.1 (4)
O1—S1—N1—C1	−80.7 (2)	C8—N3—C15—C14	−179.6 (3)
N2—S1—N1—C1	23.5 (2)	C13—C14—C15—N3	177.7 (3)
O1—S1—N2—C17	−93.9 (3)	C13—C14—C15—C16	−1.9 (4)
N1—S1—N2—C17	160.6 (3)	C9—C10—C16—C15	0.5 (4)
O1—S1—N2—C6	83.0 (2)	C9—C10—C16—C11	178.1 (3)
N1—S1—N2—C6	−22.5 (2)	N3—C15—C16—C10	0.0 (4)
C7—N1—C1—C2	−40.6 (5)	C14—C15—C16—C10	179.5 (3)
S1—N1—C1—C2	158.0 (3)	N3—C15—C16—C11	−177.7 (3)
C7—N1—C1—C6	142.0 (3)	C14—C15—C16—C11	1.8 (4)
S1—N1—C1—C6	−19.3 (3)	C12—C11—C16—C10	−178.8 (3)
C6—C1—C2—C3	−0.5 (5)	C12—C11—C16—C15	−1.2 (4)
N1—C1—C2—C3	−177.7 (3)	C6—N2—C17—O3	12.3 (5)
C1—C2—C3—C4	0.3 (5)	S1—N2—C17—O3	−171.1 (2)
C2—C3—C4—C5	0.3 (5)	C6—N2—C17—C18	−166.5 (3)
C3—C4—C5—C6	−0.8 (5)	S1—N2—C17—C18	10.1 (4)
C4—C5—C6—C1	0.6 (5)	C25—N4—C18—C19	1.7 (5)
C4—C5—C6—N2	175.4 (3)	C25—N4—C18—C17	−180.0 (3)
C2—C1—C6—C5	0.1 (5)	O3—C17—C18—N4	173.6 (3)
N1—C1—C6—C5	177.6 (3)	N2—C17—C18—N4	−7.6 (4)
C2—C1—C6—N2	−175.6 (3)	O3—C17—C18—C19	−7.8 (5)
N1—C1—C6—N2	1.9 (4)	N2—C17—C18—C19	171.0 (3)
C17—N2—C6—C5	18.0 (5)	N4—C18—C19—C20	0.6 (5)
S1—N2—C6—C5	−159.0 (3)	C17—C18—C19—C20	−177.8 (3)
C17—N2—C6—C1	−166.8 (3)	C18—C19—C20—C26	−2.2 (5)
S1—N2—C6—C1	16.2 (3)	C26—C21—C22—C23	−0.6 (5)
C1—N1—C7—O2	−1.1 (5)	C21—C22—C23—C24	0.8 (5)
S1—N1—C7—O2	158.3 (2)	C22—C23—C24—C25	−0.5 (5)
C1—N1—C7—C8	177.2 (3)	C18—N4—C25—C24	178.9 (3)
S1—N1—C7—C8	−23.4 (4)	C18—N4—C25—C26	−2.2 (4)
C15—N3—C8—C9	−0.2 (4)	C23—C24—C25—N4	179.0 (3)
C15—N3—C8—C7	−179.5 (2)	C23—C24—C25—C26	0.0 (5)
O2—C7—C8—N3	162.9 (3)	C19—C20—C26—C21	−179.1 (3)
N1—C7—C8—N3	−15.4 (4)	C19—C20—C26—C25	1.7 (5)
O2—C7—C8—C9	−16.4 (4)	C22—C21—C26—C20	−179.1 (3)
N1—C7—C8—C9	165.2 (3)	C22—C21—C26—C25	0.1 (5)
N3—C8—C9—C10	0.7 (4)	N4—C25—C26—C20	0.5 (5)
C7—C8—C9—C10	179.9 (3)	C24—C25—C26—C20	179.5 (3)
C8—C9—C10—C16	−0.8 (4)	N4—C25—C26—C21	−178.7 (3)
C16—C11—C12—C13	0.7 (5)	C24—C25—C26—C21	0.2 (4)
C11—C12—C13—C14	−0.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2i	0.95	2.51	3.262 (4)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2i	0.95	2.51	3.262 (4)	136

Symmetry code: (i) .