N,N-Bis(quinolin-8-yl)-2,2'-[(1,3,4-thia-diazole-2,5-di-yl)bis-(sulfanedi-yl)]diacetamide monohydrate.

In the title compound, C(24)H(18)N(6)O(2)S(3)·H(2)O, the thia-diazole ring makes dihedral angles of 78.00 (13) and 77.27 (13)° with the quinoline ring systems. In the crystal, mol-ecules are linked into a two-dimensional network by O-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For background to the applications of 2,5-dimercapto-1,3,4-thia­diazole, see: Vullo et al. (2003 ▶); Gurn (2001 ▶). For related 2,5-dimercapto-1,3,4-thia­diazole structures, see: Wen et al. (2005 ▶); Zhang et al. (2005 ▶).

Experimental

Crystal data

C24H18N6O2S3·H2O

M = 536.64

Monoclinic,

a = 10.8215 (8) Å

b = 10.2355 (8) Å

c = 21.5510 (16) Å

β = 90.068 (1)°

V = 2387.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 293 K

0.15 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.949, T max = 0.966

12711 measured reflections

4542 independent reflections

3469 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.109

S = 1.02

4542 reflections

333 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker 2001 ▶); cell refinement: SAINT (Bruker 2001 ▶); 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/S1600536811047222/hg5124sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047222/hg5124Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047222/hg5124Isup3.cml

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

C24H18N6O2S3·H2O	F(000) = 1112
Mr = 536.64	Dx = 1.493 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2913 reflections
a = 10.8215 (8) Å	θ = 2.2–24.6°
b = 10.2355 (8) Å	µ = 0.35 mm−1
c = 21.5510 (16) Å	T = 293 K
β = 90.068 (1)°	Prism, brown
V = 2387.1 (3) Å3	0.15 × 0.10 × 0.10 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4542 independent reflections
Radiation source: fine-focus sealed tube	3469 reflections with I > 2σ(I)
graphite	Rint = 0.031
phi and ω scans	θmax = 25.7°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→13
Tmin = 0.949, Tmax = 0.966	k = −12→11
12711 measured reflections	l = −26→26

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0551P)2 + 0.3494P] where P = (Fo2 + 2Fc2)/3
4542 reflections	(Δ/σ)max < 0.001
333 parameters	Δρmax = 0.28 e Å−3
3 restraints	Δρmin = −0.19 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	0.48854 (6)	0.33999 (6)	0.03568 (3)	0.04181 (18)
S2	0.65584 (6)	0.67713 (6)	0.23342 (3)	0.04294 (18)
S3	0.52541 (6)	0.56902 (7)	0.12152 (3)	0.0484 (2)
N2	0.93916 (17)	0.68189 (19)	0.23701 (8)	0.0376 (5)
H2	0.8860	0.7272	0.2166	0.045*
N4	0.68075 (18)	0.4337 (2)	0.18382 (9)	0.0409 (5)
N5	0.78366 (18)	0.4925 (2)	−0.08496 (9)	0.0445 (5)
N6	0.98890 (17)	0.8914 (2)	0.16646 (9)	0.0422 (5)
O2	0.95579 (16)	0.5195 (2)	0.30789 (9)	0.0598 (5)
C24	1.0876 (2)	0.8188 (2)	0.18599 (10)	0.0342 (5)
C16	1.0642 (2)	0.7078 (2)	0.22398 (10)	0.0344 (5)
O1	0.76858 (17)	0.09593 (19)	0.04223 (9)	0.0592 (5)
C8	0.8872 (2)	0.4250 (2)	−0.06819 (10)	0.0375 (5)
C10	0.7060 (2)	0.1861 (2)	0.02251 (10)	0.0395 (6)
C20	1.2107 (2)	0.8493 (2)	0.16943 (11)	0.0374 (5)
C15	0.8927 (2)	0.5951 (2)	0.27744 (10)	0.0383 (5)
C9	0.8725 (2)	0.3130 (2)	−0.02972 (10)	0.0382 (5)
N3	0.63967 (18)	0.35305 (19)	0.13605 (8)	0.0413 (5)
N1	0.75026 (17)	0.2858 (2)	−0.01150 (9)	0.0416 (5)
H1	0.6958	0.3411	−0.0240	0.050*
C13	0.62927 (19)	0.5483 (2)	0.18185 (10)	0.0353 (5)
C4	1.0072 (2)	0.4606 (3)	−0.08780 (11)	0.0435 (6)
C12	0.5590 (2)	0.4104 (2)	0.10073 (10)	0.0361 (5)
C14	0.7546 (2)	0.5972 (2)	0.28903 (10)	0.0398 (6)
H14A	0.7410	0.6384	0.3290	0.080*
H14B	0.7271	0.5074	0.2927	0.080*
C11	0.5678 (2)	0.1851 (2)	0.03428 (11)	0.0416 (6)
H11A	0.5537	0.1423	0.0738	0.080*
H11B	0.5295	0.1314	0.0025	0.080*
C1	0.9732 (2)	0.2404 (3)	−0.01294 (12)	0.0499 (7)
H1A	0.9633	0.1663	0.0115	0.060*
C19	1.3081 (2)	0.7714 (3)	0.19269 (12)	0.0467 (6)
H19	1.3895	0.7920	0.1831	0.056*
C21	1.2295 (2)	0.9559 (3)	0.12920 (12)	0.0461 (6)
H21	1.3089	0.9783	0.1166	0.055*
C22	1.1310 (3)	1.0255 (3)	0.10913 (12)	0.0513 (7)
H22	1.1418	1.0958	0.0824	0.062*
C6	0.9135 (3)	0.6360 (3)	−0.14421 (12)	0.0560 (7)
H6	0.9186	0.7077	−0.1705	0.067*
C17	1.1607 (2)	0.6324 (2)	0.24427 (11)	0.0432 (6)
H17	1.1456	0.5584	0.2682	0.052*
C18	1.2827 (2)	0.6669 (3)	0.22894 (12)	0.0506 (7)
H18	1.3476	0.6166	0.2441	0.061*
C2	1.0919 (2)	0.2781 (3)	−0.03267 (13)	0.0585 (8)
H2A	1.1599	0.2284	−0.0208	0.070*
C23	1.0124 (3)	0.9901 (3)	0.12920 (12)	0.0517 (7)
H23	0.9459	1.0397	0.1153	0.062*
C7	0.7990 (3)	0.5934 (3)	−0.12173 (12)	0.0542 (7)
H7	0.7290	0.6398	−0.1337	0.065*
C3	1.1092 (2)	0.3847 (3)	−0.06834 (13)	0.0552 (7)
H3	1.1887	0.4084	−0.0802	0.066*
C5	1.0168 (3)	0.5704 (3)	−0.12682 (12)	0.0520 (7)
H5	1.0939	0.5980	−0.1407	0.062*
O1W	0.6164 (3)	−0.1290 (2)	0.08683 (12)	0.0789 (7)
H1WA	0.679 (6)	−0.071 (7)	0.073 (3)	0.27 (4)*
H1WB	0.593 (4)	−0.085 (4)	0.1230 (19)	0.130 (17)*

	U11	U22	U33	U12	U13	U23
S1	0.0407 (4)	0.0475 (4)	0.0372 (3)	0.0041 (3)	−0.0073 (3)	−0.0041 (3)
S2	0.0381 (3)	0.0438 (4)	0.0470 (4)	0.0016 (3)	−0.0049 (3)	−0.0076 (3)
S3	0.0509 (4)	0.0457 (4)	0.0487 (4)	0.0147 (3)	−0.0176 (3)	−0.0088 (3)
N2	0.0308 (10)	0.0446 (12)	0.0373 (10)	0.0012 (8)	−0.0025 (8)	0.0077 (9)
N4	0.0423 (11)	0.0442 (13)	0.0363 (11)	0.0041 (9)	−0.0060 (9)	−0.0003 (9)
N5	0.0432 (12)	0.0470 (13)	0.0434 (12)	−0.0013 (10)	0.0001 (9)	0.0033 (10)
N6	0.0392 (11)	0.0471 (13)	0.0403 (11)	0.0049 (9)	0.0019 (9)	0.0064 (10)
O2	0.0464 (11)	0.0685 (13)	0.0645 (12)	0.0073 (9)	0.0055 (9)	0.0286 (10)
C24	0.0353 (13)	0.0353 (13)	0.0319 (11)	0.0013 (10)	−0.0001 (10)	−0.0070 (10)
C16	0.0321 (12)	0.0392 (14)	0.0321 (12)	0.0000 (10)	−0.0004 (9)	−0.0036 (10)
O1	0.0534 (11)	0.0576 (13)	0.0666 (12)	0.0114 (9)	0.0089 (9)	0.0233 (10)
C8	0.0389 (13)	0.0430 (14)	0.0307 (12)	−0.0013 (10)	0.0004 (10)	−0.0067 (11)
C10	0.0451 (14)	0.0397 (14)	0.0337 (12)	0.0017 (11)	−0.0002 (10)	0.0017 (11)
C20	0.0350 (13)	0.0375 (14)	0.0398 (13)	−0.0025 (10)	0.0018 (10)	−0.0083 (11)
C15	0.0380 (13)	0.0415 (14)	0.0355 (12)	−0.0014 (11)	−0.0010 (10)	−0.0017 (11)
C9	0.0379 (13)	0.0454 (15)	0.0313 (12)	0.0014 (11)	0.0027 (10)	−0.0061 (11)
N3	0.0487 (12)	0.0406 (12)	0.0345 (10)	0.0035 (9)	−0.0069 (9)	−0.0001 (9)
N1	0.0385 (11)	0.0450 (12)	0.0414 (11)	0.0037 (9)	0.0025 (9)	0.0054 (10)
C13	0.0276 (11)	0.0439 (14)	0.0346 (12)	−0.0019 (10)	0.0010 (9)	0.0009 (11)
C4	0.0447 (15)	0.0487 (16)	0.0373 (13)	−0.0034 (12)	0.0056 (11)	−0.0073 (12)
C12	0.0329 (12)	0.0422 (14)	0.0331 (12)	0.0008 (10)	0.0010 (10)	0.0006 (10)
C14	0.0366 (13)	0.0502 (16)	0.0326 (12)	−0.0058 (11)	0.0007 (10)	−0.0035 (11)
C11	0.0453 (14)	0.0381 (14)	0.0415 (13)	−0.0019 (11)	0.0010 (11)	−0.0014 (11)
C1	0.0477 (16)	0.0579 (18)	0.0440 (14)	0.0072 (13)	0.0041 (12)	0.0048 (13)
C19	0.0324 (13)	0.0504 (16)	0.0574 (16)	−0.0016 (11)	0.0048 (11)	−0.0051 (13)
C21	0.0440 (14)	0.0458 (16)	0.0484 (15)	−0.0084 (12)	0.0081 (12)	−0.0052 (12)
C22	0.0588 (17)	0.0461 (16)	0.0492 (15)	−0.0045 (13)	0.0042 (13)	0.0104 (13)
C6	0.067 (2)	0.0495 (17)	0.0520 (16)	−0.0082 (14)	0.0080 (14)	0.0066 (13)
C17	0.0412 (14)	0.0404 (15)	0.0479 (14)	0.0023 (11)	0.0007 (11)	0.0053 (12)
C18	0.0353 (14)	0.0530 (17)	0.0634 (17)	0.0087 (12)	−0.0035 (12)	0.0026 (14)
C2	0.0413 (15)	0.076 (2)	0.0586 (17)	0.0156 (14)	0.0047 (13)	0.0043 (16)
C23	0.0528 (17)	0.0515 (17)	0.0507 (16)	0.0107 (13)	0.0016 (12)	0.0124 (13)
C7	0.0529 (17)	0.0523 (18)	0.0575 (17)	0.0025 (13)	0.0021 (13)	0.0093 (14)
C3	0.0374 (15)	0.072 (2)	0.0567 (17)	0.0002 (13)	0.0064 (12)	−0.0029 (15)
C5	0.0480 (16)	0.0574 (18)	0.0505 (16)	−0.0131 (13)	0.0100 (12)	−0.0044 (14)
O1W	0.0971 (18)	0.0642 (15)	0.0753 (16)	−0.0058 (13)	−0.0050 (13)	−0.0143 (13)

S1—C12	1.750 (2)	N1—H1	0.8600
S1—C11	1.803 (3)	C4—C5	1.407 (4)
S2—C13	1.748 (2)	C4—C3	1.414 (4)
S2—C14	1.801 (2)	C14—H14A	0.9700
S3—C12	1.723 (2)	C14—H14B	0.9700
S3—C13	1.731 (2)	C11—H11A	0.9700
N2—C15	1.343 (3)	C11—H11B	0.9700
N2—C16	1.408 (3)	C1—C2	1.408 (4)
N2—H2	0.8600	C1—H1A	0.9300
N4—C13	1.299 (3)	C19—C18	1.353 (4)
N4—N3	1.392 (3)	C19—H19	0.9300
N5—C7	1.313 (3)	C21—C22	1.352 (4)
N5—C8	1.365 (3)	C21—H21	0.9300
N6—C23	1.316 (3)	C22—C23	1.403 (4)
N6—C24	1.367 (3)	C22—H22	0.9300
O2—C15	1.222 (3)	C6—C5	1.357 (4)
C24—C20	1.414 (3)	C6—C7	1.400 (4)
C24—C16	1.424 (3)	C6—H6	0.9300
C16—C17	1.370 (3)	C17—C18	1.406 (3)
O1—C10	1.221 (3)	C17—H17	0.9300
C8—C4	1.414 (3)	C18—H18	0.9300
C8—C9	1.424 (3)	C2—C3	1.347 (4)
C10—N1	1.345 (3)	C2—H2A	0.9300
C10—C11	1.517 (3)	C23—H23	0.9300
C20—C21	1.409 (3)	C7—H7	0.9300
C20—C19	1.413 (3)	C3—H3	0.9300
C15—C14	1.516 (3)	C5—H5	0.9300
C9—C1	1.367 (3)	O1W—H1WA	0.95 (6)
C9—N1	1.408 (3)	O1W—H1WB	0.93 (4)
N3—C12	1.298 (3)
C12—S1—C11	99.71 (11)	C15—C14—H14B	107.6
C13—S2—C14	100.22 (11)	S2—C14—H14B	107.6
C12—S3—C13	86.72 (11)	H14A—C14—H14B	107.1
C15—N2—C16	127.9 (2)	C10—C11—S1	117.78 (17)
C15—N2—H2	116.0	C10—C11—H11A	107.9
C16—N2—H2	116.0	S1—C11—H11A	107.9
C13—N4—N3	112.00 (18)	C10—C11—H11B	107.9
C7—N5—C8	117.0 (2)	S1—C11—H11B	107.9
C23—N6—C24	117.0 (2)	H11A—C11—H11B	107.2
N6—C24—C20	122.5 (2)	C9—C1—C2	119.9 (3)
N6—C24—C16	118.1 (2)	C9—C1—H1A	120.0
C20—C24—C16	119.3 (2)	C2—C1—H1A	120.0
C17—C16—N2	124.3 (2)	C18—C19—C20	120.0 (2)
C17—C16—C24	119.8 (2)	C18—C19—H19	120.0
N2—C16—C24	115.88 (19)	C20—C19—H19	120.0
N5—C8—C4	123.0 (2)	C22—C21—C20	119.3 (2)
N5—C8—C9	118.0 (2)	C22—C21—H21	120.3
C4—C8—C9	119.1 (2)	C20—C21—H21	120.3
O1—C10—N1	124.5 (2)	C21—C22—C23	119.1 (2)
O1—C10—C11	118.9 (2)	C21—C22—H22	120.4
N1—C10—C11	116.6 (2)	C23—C22—H22	120.4
C21—C20—C19	123.2 (2)	C5—C6—C7	118.7 (3)
C21—C20—C24	117.6 (2)	C5—C6—H6	120.7
C19—C20—C24	119.2 (2)	C7—C6—H6	120.7
O2—C15—N2	123.9 (2)	C16—C17—C18	119.9 (2)
O2—C15—C14	118.1 (2)	C16—C17—H17	120.0
N2—C15—C14	117.8 (2)	C18—C17—H17	120.0
C1—C9—N1	124.6 (2)	C19—C18—C17	121.7 (2)
C1—C9—C8	120.1 (2)	C19—C18—H18	119.2
N1—C9—C8	115.3 (2)	C17—C18—H18	119.2
C12—N3—N4	112.3 (2)	C3—C2—C1	121.5 (3)
C10—N1—C9	129.6 (2)	C3—C2—H2A	119.3
C10—N1—H1	115.2	C1—C2—H2A	119.3
C9—N1—H1	115.2	N6—C23—C22	124.3 (2)
N4—C13—S3	114.42 (17)	N6—C23—H23	117.8
N4—C13—S2	126.16 (17)	C22—C23—H23	117.8
S3—C13—S2	119.42 (14)	N5—C7—C6	124.5 (3)
C5—C4—C3	123.9 (2)	N5—C7—H7	117.8
C5—C4—C8	117.0 (2)	C6—C7—H7	117.8
C3—C4—C8	119.1 (2)	C2—C3—C4	120.3 (2)
N3—C12—S3	114.56 (17)	C2—C3—H3	119.8
N3—C12—S1	125.12 (19)	C4—C3—H3	119.8
S3—C12—S1	120.31 (13)	C6—C5—C4	119.9 (2)
C15—C14—S2	118.78 (16)	C6—C5—H5	120.1
C15—C14—H14A	107.6	C4—C5—H5	120.1
S2—C14—H14A	107.6	H1WA—O1W—H1WB	99 (4)
C23—N6—C24—C20	2.3 (3)	N4—N3—C12—S3	0.5 (3)
C23—N6—C24—C16	−177.1 (2)	N4—N3—C12—S1	179.22 (15)
C15—N2—C16—C17	10.7 (4)	C13—S3—C12—N3	−0.37 (18)
C15—N2—C16—C24	−170.7 (2)	C13—S3—C12—S1	−179.18 (15)
N6—C24—C16—C17	179.8 (2)	C11—S1—C12—N3	−3.3 (2)
C20—C24—C16—C17	0.3 (3)	C11—S1—C12—S3	175.39 (14)
N6—C24—C16—N2	1.1 (3)	O2—C15—C14—S2	−165.45 (19)
C20—C24—C16—N2	−178.34 (19)	N2—C15—C14—S2	18.5 (3)
C7—N5—C8—C4	1.0 (3)	C13—S2—C14—C15	87.36 (19)
C7—N5—C8—C9	−178.3 (2)	O1—C10—C11—S1	154.2 (2)
N6—C24—C20—C21	−2.6 (3)	N1—C10—C11—S1	−28.2 (3)
C16—C24—C20—C21	176.8 (2)	C12—S1—C11—C10	−64.46 (19)
N6—C24—C20—C19	178.5 (2)	N1—C9—C1—C2	−178.6 (2)
C16—C24—C20—C19	−2.1 (3)	C8—C9—C1—C2	1.3 (4)
C16—N2—C15—O2	−3.4 (4)	C21—C20—C19—C18	−177.0 (2)
C16—N2—C15—C14	172.5 (2)	C24—C20—C19—C18	1.8 (4)
N5—C8—C9—C1	178.4 (2)	C19—C20—C21—C22	−180.0 (2)
C4—C8—C9—C1	−0.9 (3)	C24—C20—C21—C22	1.2 (3)
N5—C8—C9—N1	−1.7 (3)	C20—C21—C22—C23	0.4 (4)
C4—C8—C9—N1	179.0 (2)	N2—C16—C17—C18	−179.7 (2)
C13—N4—N3—C12	−0.3 (3)	C24—C16—C17—C18	1.8 (3)
O1—C10—N1—C9	−2.8 (4)	C20—C19—C18—C17	0.3 (4)
C11—C10—N1—C9	179.8 (2)	C16—C17—C18—C19	−2.1 (4)
C1—C9—N1—C10	−2.6 (4)	C9—C1—C2—C3	−0.3 (4)
C8—C9—N1—C10	177.5 (2)	C24—N6—C23—C22	−0.6 (4)
N3—N4—C13—S3	0.1 (2)	C21—C22—C23—N6	−0.7 (4)
N3—N4—C13—S2	179.95 (15)	C8—N5—C7—C6	−0.4 (4)
C12—S3—C13—N4	0.17 (18)	C5—C6—C7—N5	−0.7 (4)
C12—S3—C13—S2	−179.74 (14)	C1—C2—C3—C4	−1.1 (4)
C14—S2—C13—N4	−5.8 (2)	C5—C4—C3—C2	−177.7 (3)
C14—S2—C13—S3	174.10 (13)	C8—C4—C3—C2	1.4 (4)
N5—C8—C4—C5	−0.6 (3)	C7—C6—C5—C4	1.1 (4)
C9—C8—C4—C5	178.7 (2)	C3—C4—C5—C6	178.6 (3)
N5—C8—C4—C3	−179.8 (2)	C8—C4—C5—C6	−0.5 (4)
C9—C8—C4—C3	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1	0.95 (7)	2.07 (7)	2.990 (3)	162 (6)
O1W—H1WB···O2i	0.94 (4)	1.91 (4)	2.841 (3)	175 (4)
C11—H11B···O1Wii	0.97	2.49	3.332 (4)	145
C23—H23···O1iii	0.93	2.55	3.411 (4)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O1	0.95 (7)	2.07 (7)	2.990 (3)	162 (6)
O1W—H1WB⋯O2i	0.94 (4)	1.91 (4)	2.841 (3)	175 (4)
C11—H11B⋯O1Wii	0.97	2.49	3.332 (4)	145
C23—H23⋯O1iii	0.93	2.55	3.411 (4)	155

Symmetry codes: (i) ; (ii) ; (iii) .