N-(2,3-Dihydro-1,3-thia-zol-2-yl-idene)-4-[(2-hydroxy-benzyl-idene)amino]benzene-sulfonamide.

The title compound, C(16)H(13)N(3)O(3)S(2), was prepared by reaction of salicylaldehyde and sulfathia-zole in methanol. The dihedral angle between the central benzene ring and the thia-zole ring is 85.2 (2)° and that between the two benzene rings is 17.9 (2)°. An intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are held together by inter-molecular N-H⋯N and C-H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane.

Related literature

For the biological activity of Schiff bases, see: Billson et al. (2000 ▶); Carlton et al. (1995 ▶). For a related structure, see: Li et al. (2006 ▶).

Experimental

Crystal data

C16H13N3O3S2

M = 359.41

Monoclinic,

a = 16.1693 (18) Å

b = 9.1211 (11) Å

c = 11.0292 (13) Å

β = 101.896 (1)°

V = 1591.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 298 K

0.40 × 0.37 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.871, T max = 0.932

7737 measured reflections

2806 independent reflections

1927 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.108

S = 1.04

2806 reflections

224 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809033704/ci2883sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033704/ci2883Isup2.hkl

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

C16H13N3O3S2	F(000) = 744
Mr = 359.41	Dx = 1.500 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2137 reflections
a = 16.1693 (18) Å	θ = 2.6–25.0°
b = 9.1211 (11) Å	µ = 0.36 mm−1
c = 11.0292 (13) Å	T = 298 K
β = 101.896 (1)°	Block, yellow
V = 1591.7 (3) Å3	0.40 × 0.37 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2806 independent reflections
Radiation source: fine-focus sealed tube	1927 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.871, Tmax = 0.932	k = −10→10
7737 measured reflections	l = −8→13

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.04P)2 + 1.0601P] where P = (Fo2 + 2Fc2)/3
2806 reflections	(Δ/σ)max = 0.001
224 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.30 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
N1	0.54316 (16)	0.2823 (3)	0.3783 (2)	0.0517 (7)
N2	0.95632 (15)	0.6826 (3)	0.4499 (2)	0.0375 (6)
H2A	0.9910 (19)	0.640 (3)	0.513 (3)	0.055 (10)*
N3	0.93153 (14)	0.4585 (2)	0.3503 (2)	0.0370 (6)
O1	0.86589 (13)	0.4333 (2)	0.12312 (17)	0.0484 (5)
O2	0.91746 (13)	0.2184 (2)	0.2533 (2)	0.0506 (6)
O3	0.45423 (16)	0.1377 (3)	0.5144 (2)	0.0728 (8)
H3A	0.498 (3)	0.166 (5)	0.470 (4)	0.109*
S1	0.87791 (4)	0.35993 (8)	0.24101 (7)	0.0379 (2)
S2	0.86729 (5)	0.71804 (9)	0.23688 (7)	0.0475 (2)
C1	0.77728 (17)	0.3381 (3)	0.2773 (3)	0.0363 (7)
C2	0.70885 (18)	0.4196 (3)	0.2163 (3)	0.0441 (8)
H2	0.7157	0.4862	0.1553	0.053*
C3	0.63071 (18)	0.4019 (4)	0.2458 (3)	0.0494 (8)
H3B	0.5849	0.4559	0.2036	0.059*
C4	0.61981 (19)	0.3047 (4)	0.3375 (3)	0.0458 (8)
C5	0.68850 (19)	0.2214 (3)	0.3959 (3)	0.0482 (8)
H5	0.6814	0.1526	0.4551	0.058*
C6	0.76694 (19)	0.2390 (3)	0.3675 (3)	0.0438 (7)
H6	0.8127	0.1845	0.4090	0.053*
C7	0.4851 (2)	0.3782 (4)	0.3608 (3)	0.0555 (9)
H7	0.4919	0.4613	0.3151	0.067*
C8	0.40865 (19)	0.3643 (4)	0.4087 (3)	0.0496 (8)
C9	0.39700 (19)	0.2481 (4)	0.4865 (3)	0.0527 (8)
C10	0.3252 (2)	0.2432 (4)	0.5367 (3)	0.0633 (10)
H10	0.3174	0.1666	0.5889	0.076*
C11	0.2658 (2)	0.3519 (5)	0.5089 (3)	0.0662 (11)
H11	0.2180	0.3485	0.5435	0.079*
C12	0.2749 (2)	0.4648 (5)	0.4319 (4)	0.0655 (10)
H12	0.2333	0.5364	0.4125	0.079*
C13	0.3464 (2)	0.4713 (4)	0.3833 (3)	0.0625 (10)
H13	0.3534	0.5493	0.3320	0.075*
C14	0.92217 (16)	0.6028 (3)	0.3501 (2)	0.0336 (6)
C15	0.9408 (2)	0.8303 (3)	0.4400 (3)	0.0477 (8)
H15	0.9614	0.8969	0.5029	0.057*
C16	0.8939 (2)	0.8685 (4)	0.3323 (3)	0.0554 (9)
H16	0.8772	0.9641	0.3104	0.066*

	U11	U22	U33	U12	U13	U23
N1	0.0409 (15)	0.0615 (19)	0.0528 (17)	−0.0026 (14)	0.0101 (13)	0.0003 (14)
N2	0.0399 (14)	0.0344 (14)	0.0362 (14)	−0.0024 (11)	0.0033 (12)	−0.0005 (12)
N3	0.0402 (13)	0.0306 (14)	0.0378 (13)	0.0001 (11)	0.0027 (11)	−0.0001 (11)
O1	0.0591 (13)	0.0538 (14)	0.0323 (11)	−0.0072 (11)	0.0092 (9)	−0.0014 (10)
O2	0.0532 (13)	0.0349 (12)	0.0674 (15)	0.0032 (10)	0.0213 (11)	−0.0078 (11)
O3	0.0607 (16)	0.0759 (19)	0.0865 (19)	0.0096 (14)	0.0256 (14)	0.0188 (15)
S1	0.0420 (4)	0.0339 (4)	0.0378 (4)	−0.0013 (3)	0.0086 (3)	−0.0048 (3)
S2	0.0595 (5)	0.0377 (5)	0.0424 (5)	0.0064 (4)	0.0033 (4)	0.0063 (4)
C1	0.0392 (16)	0.0360 (16)	0.0320 (15)	−0.0005 (13)	0.0032 (12)	−0.0047 (13)
C2	0.0451 (18)	0.0501 (19)	0.0344 (16)	−0.0025 (15)	0.0018 (14)	0.0069 (15)
C3	0.0388 (17)	0.062 (2)	0.0437 (19)	0.0040 (15)	0.0005 (14)	0.0058 (16)
C4	0.0422 (18)	0.052 (2)	0.0427 (18)	−0.0049 (15)	0.0083 (14)	−0.0030 (15)
C5	0.0508 (19)	0.048 (2)	0.0475 (19)	−0.0005 (16)	0.0134 (15)	0.0095 (15)
C6	0.0452 (18)	0.0428 (18)	0.0427 (18)	0.0046 (14)	0.0073 (14)	0.0029 (14)
C7	0.054 (2)	0.057 (2)	0.057 (2)	−0.0035 (18)	0.0133 (17)	0.0027 (17)
C8	0.0437 (18)	0.056 (2)	0.0481 (19)	−0.0037 (16)	0.0083 (15)	−0.0077 (17)
C9	0.0405 (18)	0.062 (2)	0.053 (2)	−0.0013 (17)	0.0044 (16)	−0.0071 (18)
C10	0.054 (2)	0.078 (3)	0.060 (2)	−0.011 (2)	0.0173 (18)	−0.007 (2)
C11	0.045 (2)	0.092 (3)	0.064 (2)	−0.004 (2)	0.0176 (18)	−0.025 (2)
C12	0.052 (2)	0.072 (3)	0.070 (3)	0.0065 (19)	0.0075 (19)	−0.019 (2)
C13	0.058 (2)	0.062 (2)	0.066 (2)	0.0037 (19)	0.0111 (19)	−0.0043 (19)
C14	0.0300 (14)	0.0360 (17)	0.0356 (16)	−0.0015 (12)	0.0087 (12)	−0.0014 (13)
C15	0.056 (2)	0.0333 (18)	0.054 (2)	−0.0060 (15)	0.0122 (16)	−0.0056 (15)
C16	0.068 (2)	0.0320 (18)	0.066 (2)	0.0033 (16)	0.0122 (19)	0.0023 (16)

N1—C7	1.269 (4)	C4—C5	1.389 (4)
N1—C4	1.418 (4)	C5—C6	1.377 (4)
N2—C14	1.340 (3)	C5—H5	0.93
N2—C15	1.371 (4)	C6—H6	0.93
N2—H2A	0.89 (3)	C7—C8	1.446 (4)
N3—C14	1.325 (3)	C7—H7	0.93
N3—S1	1.607 (2)	C8—C13	1.388 (4)
O1—S1	1.440 (2)	C8—C9	1.401 (5)
O2—S1	1.434 (2)	C9—C10	1.386 (5)
O3—C9	1.359 (4)	C10—C11	1.371 (5)
O3—H3A	0.97 (4)	C10—H10	0.93
S1—C1	1.765 (3)	C11—C12	1.362 (5)
S2—C16	1.728 (3)	C11—H11	0.93
S2—C14	1.730 (3)	C12—C13	1.373 (5)
C1—C6	1.379 (4)	C12—H12	0.93
C1—C2	1.387 (4)	C13—H13	0.93
C2—C3	1.377 (4)	C15—C16	1.318 (4)
C2—H2	0.93	C15—H15	0.93
C3—C4	1.384 (4)	C16—H16	0.93
C3—H3B	0.93
C7—N1—C4	121.4 (3)	N1—C7—C8	123.1 (3)
C14—N2—C15	115.6 (3)	N1—C7—H7	118.5
C14—N2—H2A	119 (2)	C8—C7—H7	118.5
C15—N2—H2A	125 (2)	C13—C8—C9	118.2 (3)
C14—N3—S1	120.72 (19)	C13—C8—C7	120.2 (3)
C9—O3—H3A	103 (3)	C9—C8—C7	121.5 (3)
O2—S1—O1	118.59 (13)	O3—C9—C10	118.2 (3)
O2—S1—N3	105.74 (12)	O3—C9—C8	121.9 (3)
O1—S1—N3	111.64 (12)	C10—C9—C8	119.9 (3)
O2—S1—C1	106.91 (13)	C11—C10—C9	119.6 (4)
O1—S1—C1	107.36 (13)	C11—C10—H10	120.2
N3—S1—C1	105.84 (12)	C9—C10—H10	120.2
C16—S2—C14	90.97 (15)	C12—C11—C10	121.7 (4)
C6—C1—C2	119.9 (3)	C12—C11—H11	119.2
C6—C1—S1	119.5 (2)	C10—C11—H11	119.2
C2—C1—S1	120.7 (2)	C11—C12—C13	118.9 (4)
C3—C2—C1	120.1 (3)	C11—C12—H12	120.5
C3—C2—H2	119.9	C13—C12—H12	120.5
C1—C2—H2	119.9	C12—C13—C8	121.7 (4)
C2—C3—C4	120.6 (3)	C12—C13—H13	119.2
C2—C3—H3B	119.7	C8—C13—H13	119.2
C4—C3—H3B	119.7	N3—C14—N2	120.7 (3)
C3—C4—C5	118.6 (3)	N3—C14—S2	130.3 (2)
C3—C4—N1	125.2 (3)	N2—C14—S2	109.0 (2)
C5—C4—N1	116.2 (3)	C16—C15—N2	113.1 (3)
C6—C5—C4	121.1 (3)	C16—C15—H15	123.4
C6—C5—H5	119.4	N2—C15—H15	123.4
C4—C5—H5	119.4	C15—C16—S2	111.3 (2)
C5—C6—C1	119.6 (3)	C15—C16—H16	124.3
C5—C6—H6	120.2	S2—C16—H16	124.3
C1—C6—H6	120.2
C14—N3—S1—O2	166.3 (2)	N1—C7—C8—C13	−178.2 (3)
C14—N3—S1—O1	36.0 (3)	N1—C7—C8—C9	5.1 (5)
C14—N3—S1—C1	−80.5 (2)	C13—C8—C9—O3	178.9 (3)
O2—S1—C1—C6	34.9 (3)	C7—C8—C9—O3	−4.3 (5)
O1—S1—C1—C6	163.2 (2)	C13—C8—C9—C10	−0.7 (5)
N3—S1—C1—C6	−77.5 (3)	C7—C8—C9—C10	176.1 (3)
O2—S1—C1—C2	−145.2 (2)	O3—C9—C10—C11	−179.1 (3)
O1—S1—C1—C2	−16.9 (3)	C8—C9—C10—C11	0.5 (5)
N3—S1—C1—C2	102.4 (2)	C9—C10—C11—C12	0.6 (5)
C6—C1—C2—C3	0.1 (4)	C10—C11—C12—C13	−1.5 (5)
S1—C1—C2—C3	−179.8 (2)	C11—C12—C13—C8	1.3 (5)
C1—C2—C3—C4	0.9 (5)	C9—C8—C13—C12	−0.2 (5)
C2—C3—C4—C5	−2.4 (5)	C7—C8—C13—C12	−177.0 (3)
C2—C3—C4—N1	177.4 (3)	S1—N3—C14—N2	169.4 (2)
C7—N1—C4—C3	−21.1 (5)	S1—N3—C14—S2	−8.7 (4)
C7—N1—C4—C5	158.7 (3)	C15—N2—C14—N3	−178.5 (3)
C3—C4—C5—C6	2.8 (5)	C15—N2—C14—S2	0.0 (3)
N1—C4—C5—C6	−177.0 (3)	C16—S2—C14—N3	178.1 (3)
C4—C5—C6—C1	−1.8 (5)	C16—S2—C14—N2	−0.1 (2)
C2—C1—C6—C5	0.3 (4)	C14—N2—C15—C16	0.3 (4)
S1—C1—C6—C5	−179.8 (2)	N2—C15—C16—S2	−0.4 (4)
C4—N1—C7—C8	−175.4 (3)	C14—S2—C16—C15	0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N1	0.97 (4)	1.73 (4)	2.636 (4)	154 (4)
N2—H2A···N3i	0.89 (3)	1.97 (3)	2.856 (3)	179 (3)
C6—H6···O1ii	0.93	2.58	3.334 (4)	139
C16—H16···O2iii	0.93	2.52	3.351 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N1	0.97 (4)	1.73 (4)	2.636 (4)	154 (4)
N2—H2A⋯N3i	0.89 (3)	1.97 (3)	2.856 (3)	179 (3)
C6—H6⋯O1ii	0.93	2.58	3.334 (4)	139
C16—H16⋯O2iii	0.93	2.52	3.351 (4)	148

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