N-(2,3-Dihydro-1,3-thia­zol-2-yl­idene)-4-[(2-hydroxy­benzyl­idene)amino]benzene­sulfonamide

Zhang, X.-L.

doi:10.1107/S1600536809033704

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2274

doi:10.1107/S1600536809033704

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N-(2,3-Dihydro-1,3-thiazol-2-ylidene)-4-[(2-hydroxybenzylidene)amino]benzenesulfonamide

Xin-Li Zhang ^a ^*

^aDepartment of Chemistry, Baoji University of Arts and Sciences, Baoji, Shaanxi 721007, People's Republic of China
^*Correspondence e-mail: zhangxinli6008@163.com

(Received 7 August 2009; accepted 24 August 2009; online 29 August 2009)

The title compound, C₁₆H₁₃N₃O₃S₂, was prepared by reaction of salicylaldehyde and sulfathiazole in methanol. The dihedral angle between the central benzene ring and the thiazole ring is 85.2 (2)° and that between the two benzene rings is 17.9 (2)°. An intramolecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, molecules are held together by intermolecular 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_r = 359.41
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.108
S = 1.04
2806 reflections
224 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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) -x+2, -y+1, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x, y+1, z.

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.

Supporting information

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

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

checkCIF report

Comment top

The synthesis and characterization of Schiff base compounds have received a great deal of attention due to their biological activities, such as anti-bacterial, anti-cancer and anti-virus (Billson et al., 2000; Carlton et al., 1995). In this paper, we report the crystal structure of the title compound, a new Schiff-base ligand, (I).

Bbond lengths and angles in (I) are normal and they agree with those observed in a salicylaldehyde Schiff base (Li et al., 2006). The C7db// N1 bond length of 1.269 (4) Å conforms to the value for a double bond. The dihedral angle between C1-C6 benzene ring and thiazole ring is 85.2 (2)°. The dihedral angle between the two benzene rings is 17.9 (2)°. An intramolecular O3—H3A···N1 hydrogen bond generates an S(6) ring motif (Fig. 1).

The molecules are held together by N—H···N and C—H···O intermolecular hydrogen bonds (Table 1), forming a two-dimensional network parallel to the bc plane (Fig. 2).

Related literature top

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 top

All chemicals were of reagent grade and commercially available from the Beijing Chemical Reagents Company of China, and were used without further purification. A methanol solution (10 ml) of salicylaldehyde (0.1 mmol, 12.2 mg) and sulfathiazloe (0.1 mmol, 25.5 mg) was stirred at room temperature for 30 min and then filtered. The filtrate was left to stand in air for 7 d, and the title compound was formed in slow evaporation of the solvent. The crystals were collected, washed with methanol and dried in a vacuum desiccator using anhydrous CaCl₂ (yield 64%).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The crystal packing of (I), viewed along the b axis. Hydrogen bonds are shown as dashed lines.

N-(2,3-Dihydro-1,3-thiazol-2-ylidene)-4-[(2- hydroxybenzylidene)amino]benzenesulfonamide top

Crystal data top

C₁₆H₁₃N₃O₃S₂	F(000) = 744
M_r = 359.41	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.04P)² + 1.0601P] where P = (F_o² + 2F_c²)/3
2806 reflections	(Δ/σ)_max = 0.001
224 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₆H₁₃N₃O₃S₂	V = 1591.7 (3) Å³
M_r = 359.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.1693 (18) Å	µ = 0.36 mm⁻¹
b = 9.1211 (11) Å	T = 298 K
c = 11.0292 (13) Å	0.40 × 0.37 × 0.20 mm
β = 101.896 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2806 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1927 reflections with I > 2σ(I)
T_min = 0.871, T_max = 0.932	R_int = 0.031
7737 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.30 e Å⁻³
2806 reflections	Δρ_min = −0.30 e Å⁻³
224 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z+1; (ii) x, −y+1/2, z+1/2; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃N₃O₃S₂
M_r	359.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	16.1693 (18), 9.1211 (11), 11.0292 (13)
β (°)	101.896 (1)
V (Å³)	1591.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.40 × 0.37 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.871, 0.932
No. of measured, independent and observed [I > 2σ(I)] reflections	7737, 2806, 1927
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.108, 1.04
No. of reflections	2806
No. of parameters	224
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.30

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z+1; (ii) x, −y+1/2, z+1/2; (iii) x, y+1, z.

Acknowledgements

The work was supported financially by research grant No. 09JS068 from the Phytochemistry Key Laboratory of Shaanxi Province.

References

Billson, T. S., Crane, J. D., Fox, O. D. & Heath, S. L. (2000). Inorg. Chem. Commun. 3, 718–720. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Carlton, L. D., Schmith, V. D. & Brouwer, K. L. R. (1995). Prostaglandins, 50, 341–347. CrossRef CAS PubMed Web of Science Google Scholar
Li, Z.-X., Zhang, X.-L. & Wang, X.-L. (2006). Acta Cryst. E62, o4513–o4514. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 9| September 2009| Page o2274

doi:10.1107/S1600536809033704

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-(2,3-Di­hydro-1,3-thia­zol-2-yl­­idene)-4-[(2-hy­droxy­benzyl­­idene)amino]benzene­sulfonamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-(2,3-Dihydro-1,3-thiazol-2-ylidene)-4-[(2-hydroxybenzylidene)amino]benzenesulfonamide