4-{[(E)-2,3-Dihy-droxy-benzyl-idene]amino}-N-(5-methyl-1,2-oxazol-3-yl)benzene-sulfonamide.

In the title compound, C(17)H(15)N(3)O(5)S, the 2,3-dihy-droxy-benzaldehyde unit is oriented at a dihedral angles of 16.83 (10) and 78.87 (6)° with the anilinic and 5-methyl-1,2-oxazol-3-amine groups, respectively. An S(6) loop exists due to intramolecular O-H⋯N hydrogen bonding. In the crystal, inversion dimers with R(2) (2)(8) rings are formed due to N-H⋯N hydrogen bonding between the 5-methyl-1,2-oxazol-3-amine groups. These dimers are inter-linked by O-H⋯O hydrogen bonds, forming chains along [101] and resulting in R(2) (2)(26) rings. π-π inter-actions occur between the central benzene rings with a centroid-centroid distance of 3.7928 (16) Å.

Related literature

For related structures, see: Ebenezer & Muthiah (2010 ▶); Yildiz et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H15N3O5S

M = 373.38

Triclinic,

a = 7.1881 (6) Å

b = 10.6682 (10) Å

c = 11.6865 (9) Å

α = 92.181 (4)°

β = 99.776 (4)°

γ = 99.606 (5)°

V = 868.74 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.25 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.957, T max = 0.966

12511 measured reflections

3389 independent reflections

2004 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.121

S = 1.00

3389 reflections

245 parameters

All H-atom parameters refined

Δρmax = 0.19 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026657/bq2368sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026657/bq2368Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026657/bq2368Isup3.cml

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

C17H15N3O5S	Z = 2
Mr = 373.38	F(000) = 388
Triclinic, P1	Dx = 1.427 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1881 (6) Å	Cell parameters from 2704 reflections
b = 10.6682 (10) Å	θ = 1.8–26.0°
c = 11.6865 (9) Å	µ = 0.22 mm−1
α = 92.181 (4)°	T = 296 K
β = 99.776 (4)°	Prism, red
γ = 99.606 (5)°	0.25 × 0.18 × 0.16 mm
V = 868.74 (13) Å3

Bruker Kappa APEXII CCD diffractometer	3389 independent reflections
Radiation source: fine-focus sealed tube	2004 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 8.00 pixels mm-1	θmax = 26.0°, θmin = 1.9°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
Tmin = 0.957, Tmax = 0.966	l = −14→14
12511 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	All H-atom parameters refined
S = 1.00	w = 1/[σ2(Fo2) + (0.0529P)2] where P = (Fo2 + 2Fc2)/3
3389 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.72001 (10)	0.57361 (7)	0.76687 (5)	0.0470 (3)
O1	−0.2827 (3)	0.2045 (2)	0.35929 (18)	0.0731 (8)
O2	−0.5837 (4)	0.0532 (2)	0.2208 (3)	0.1008 (11)
O3	0.8978 (2)	0.54264 (18)	0.74645 (14)	0.0586 (7)
O4	0.6855 (3)	0.70107 (17)	0.75951 (15)	0.0566 (7)
O5	0.6964 (3)	0.27141 (18)	1.05698 (15)	0.0627 (8)
N1	0.0732 (3)	0.2368 (2)	0.45973 (17)	0.0504 (8)
N2	0.6991 (3)	0.5411 (2)	0.89993 (17)	0.0455 (8)
N3	0.6258 (3)	0.3814 (2)	1.02145 (19)	0.0578 (9)
C1	−0.0786 (4)	0.0495 (3)	0.3390 (2)	0.0482 (10)
C2	−0.2552 (4)	0.0909 (3)	0.3158 (2)	0.0539 (11)
C3	−0.4110 (4)	0.0144 (3)	0.2441 (3)	0.0661 (12)
C4	−0.3908 (5)	−0.1007 (3)	0.1984 (3)	0.0723 (12)
C5	−0.2166 (5)	−0.1433 (3)	0.2209 (3)	0.0711 (14)
C6	−0.0622 (5)	−0.0683 (3)	0.2899 (2)	0.0616 (11)
C7	0.0824 (4)	0.1275 (3)	0.4135 (2)	0.0534 (11)
C8	0.2336 (4)	0.3133 (3)	0.5313 (2)	0.0454 (9)
C9	0.1979 (4)	0.4123 (3)	0.6001 (2)	0.0505 (10)
C10	0.3444 (4)	0.4908 (3)	0.6723 (2)	0.0498 (10)
C11	0.5320 (3)	0.4718 (2)	0.67560 (19)	0.0433 (9)
C12	0.5690 (4)	0.3743 (3)	0.6069 (2)	0.0536 (10)
C13	0.4211 (4)	0.2965 (3)	0.5342 (2)	0.0561 (11)
C14	0.7297 (3)	0.4260 (2)	0.9455 (2)	0.0409 (9)
C15	0.8621 (4)	0.3492 (3)	0.9277 (2)	0.0497 (10)
C16	0.8378 (4)	0.2557 (3)	0.9987 (2)	0.0507 (10)
C17	0.9254 (5)	0.1416 (3)	1.0241 (3)	0.0722 (14)
H1	−0.157 (5)	0.237 (3)	0.409 (3)	0.1096*
H2	−0.575 (7)	0.128 (4)	0.232 (4)	0.1510*
H2A	0.610 (4)	0.571 (3)	0.923 (2)	0.0545*
H4	−0.49539	−0.15176	0.15139	0.0867*
H5	−0.20499	−0.22224	0.18912	0.0852*
H6	0.05487	−0.09628	0.30425	0.0738*
H7	0.19768	0.09741	0.42876	0.0641*
H9	0.07257	0.42547	0.59707	0.0606*
H10	0.31878	0.55625	0.71871	0.0597*
H12	0.69437	0.36111	0.60986	0.0643*
H13	0.44706	0.23211	0.48657	0.0669*
H15	0.94902	0.36074	0.87682	0.0596*
H17A	0.95686	0.13684	1.10685	0.1083*
H17B	1.03998	0.14728	0.99126	0.1083*
H17C	0.83640	0.06668	0.99078	0.1083*

	U11	U22	U33	U12	U13	U23
S1	0.0425 (4)	0.0536 (5)	0.0455 (4)	0.0087 (3)	0.0085 (3)	0.0062 (3)
O1	0.0544 (14)	0.0700 (15)	0.0902 (15)	0.0144 (12)	0.0028 (11)	−0.0234 (12)
O2	0.0566 (16)	0.0831 (19)	0.148 (2)	0.0095 (15)	−0.0128 (14)	−0.0255 (18)
O3	0.0377 (11)	0.0792 (15)	0.0621 (11)	0.0119 (10)	0.0168 (8)	0.0039 (10)
O4	0.0608 (13)	0.0453 (12)	0.0637 (12)	0.0103 (10)	0.0087 (9)	0.0122 (9)
O5	0.0777 (15)	0.0611 (14)	0.0611 (12)	0.0310 (12)	0.0245 (10)	0.0172 (10)
N1	0.0495 (15)	0.0590 (16)	0.0416 (12)	0.0078 (12)	0.0073 (10)	0.0002 (12)
N2	0.0463 (15)	0.0529 (15)	0.0410 (12)	0.0177 (12)	0.0094 (10)	0.0050 (11)
N3	0.0693 (17)	0.0581 (16)	0.0585 (14)	0.0326 (14)	0.0229 (12)	0.0175 (12)
C1	0.0533 (18)	0.0474 (18)	0.0447 (15)	0.0087 (15)	0.0107 (12)	0.0060 (13)
C2	0.058 (2)	0.0494 (19)	0.0536 (16)	0.0082 (16)	0.0106 (13)	−0.0029 (14)
C3	0.054 (2)	0.057 (2)	0.083 (2)	0.0067 (17)	0.0054 (16)	−0.0046 (18)
C4	0.072 (2)	0.051 (2)	0.084 (2)	−0.0021 (18)	0.0013 (18)	−0.0057 (18)
C5	0.090 (3)	0.047 (2)	0.076 (2)	0.010 (2)	0.0170 (19)	−0.0004 (17)
C6	0.071 (2)	0.0500 (19)	0.0683 (19)	0.0191 (17)	0.0161 (16)	0.0089 (16)
C7	0.0518 (19)	0.063 (2)	0.0486 (16)	0.0157 (16)	0.0105 (13)	0.0131 (15)
C8	0.0436 (17)	0.0556 (18)	0.0382 (14)	0.0119 (14)	0.0065 (12)	0.0068 (13)
C9	0.0434 (17)	0.0560 (19)	0.0530 (16)	0.0113 (15)	0.0089 (13)	0.0041 (14)
C10	0.0477 (18)	0.0520 (18)	0.0518 (16)	0.0141 (14)	0.0109 (13)	−0.0016 (14)
C11	0.0425 (16)	0.0496 (17)	0.0388 (13)	0.0097 (13)	0.0072 (11)	0.0083 (12)
C12	0.0431 (17)	0.072 (2)	0.0496 (16)	0.0197 (16)	0.0110 (13)	−0.0007 (15)
C13	0.056 (2)	0.068 (2)	0.0453 (15)	0.0146 (16)	0.0111 (13)	−0.0086 (14)
C14	0.0392 (15)	0.0433 (16)	0.0387 (14)	0.0112 (13)	0.0002 (11)	−0.0024 (12)
C15	0.0443 (17)	0.0561 (19)	0.0518 (16)	0.0171 (15)	0.0094 (12)	0.0038 (14)
C16	0.0521 (18)	0.0532 (19)	0.0472 (15)	0.0178 (15)	0.0025 (13)	−0.0011 (14)
C17	0.091 (3)	0.064 (2)	0.072 (2)	0.040 (2)	0.0165 (17)	0.0122 (17)

S1—O3	1.4275 (17)	C8—C9	1.387 (4)
S1—O4	1.426 (2)	C8—C13	1.384 (4)
S1—N2	1.632 (2)	C9—C10	1.368 (4)
S1—C11	1.754 (2)	C10—C11	1.391 (4)
O1—C2	1.354 (4)	C11—C12	1.378 (4)
O2—C3	1.361 (4)	C12—C13	1.373 (4)
O5—N3	1.404 (3)	C14—C15	1.391 (4)
O5—C16	1.345 (4)	C15—C16	1.330 (4)
O1—H1	0.99 (4)	C16—C17	1.479 (5)
O2—H2	0.79 (4)	C4—H4	0.9300
N1—C8	1.415 (4)	C5—H5	0.9300
N1—C7	1.283 (4)	C6—H6	0.9300
N2—C14	1.393 (3)	C7—H7	0.9300
N3—C14	1.308 (3)	C9—H9	0.9300
N2—H2A	0.84 (3)	C10—H10	0.9300
C1—C2	1.400 (4)	C12—H12	0.9300
C1—C7	1.439 (4)	C13—H13	0.9300
C1—C6	1.393 (4)	C15—H15	0.9300
C2—C3	1.395 (4)	C17—H17A	0.9600
C3—C4	1.360 (5)	C17—H17B	0.9600
C4—C5	1.390 (5)	C17—H17C	0.9600
C5—C6	1.369 (5)
O3—S1—O4	120.39 (13)	S1—C11—C10	119.41 (18)
O3—S1—N2	107.74 (11)	C11—C12—C13	120.1 (3)
O3—S1—C11	108.71 (11)	C8—C13—C12	120.4 (3)
O4—S1—N2	104.10 (11)	N2—C14—N3	117.6 (2)
O4—S1—C11	108.69 (11)	N2—C14—C15	130.5 (2)
N2—S1—C11	106.32 (11)	N3—C14—C15	111.9 (2)
N3—O5—C16	108.6 (2)	C14—C15—C16	105.4 (2)
C2—O1—H1	101.8 (19)	O5—C16—C17	115.6 (3)
C3—O2—H2	113 (4)	C15—C16—C17	135.0 (3)
C7—N1—C8	122.0 (2)	O5—C16—C15	109.4 (3)
S1—N2—C14	123.00 (17)	C3—C4—H4	119.00
O5—N3—C14	104.68 (19)	C5—C4—H4	119.00
C14—N2—H2A	114 (2)	C4—C5—H5	120.00
S1—N2—H2A	113.1 (17)	C6—C5—H5	120.00
C6—C1—C7	120.8 (3)	C1—C6—H6	120.00
C2—C1—C7	120.2 (3)	C5—C6—H6	120.00
C2—C1—C6	119.0 (3)	N1—C7—H7	119.00
O1—C2—C3	117.5 (3)	C1—C7—H7	119.00
C1—C2—C3	119.8 (3)	C8—C9—H9	119.00
O1—C2—C1	122.7 (3)	C10—C9—H9	120.00
O2—C3—C2	120.6 (3)	C9—C10—H10	120.00
O2—C3—C4	119.7 (3)	C11—C10—H10	120.00
C2—C3—C4	119.7 (3)	C11—C12—H12	120.00
C3—C4—C5	121.1 (3)	C13—C12—H12	120.00
C4—C5—C6	119.6 (3)	C8—C13—H13	120.00
C1—C6—C5	120.7 (3)	C12—C13—H13	120.00
N1—C7—C1	122.7 (3)	C14—C15—H15	127.00
N1—C8—C9	117.0 (3)	C16—C15—H15	127.00
N1—C8—C13	124.0 (3)	C16—C17—H17A	109.00
C9—C8—C13	119.0 (3)	C16—C17—H17B	109.00
C8—C9—C10	121.0 (3)	C16—C17—H17C	109.00
C9—C10—C11	119.4 (3)	H17A—C17—H17B	109.00
S1—C11—C12	120.56 (19)	H17A—C17—H17C	109.00
C10—C11—C12	120.0 (2)	H17B—C17—H17C	110.00
O3—S1—N2—C14	−48.5 (2)	C2—C1—C7—N1	−1.1 (4)
O4—S1—N2—C14	−177.4 (2)	C6—C1—C7—N1	179.6 (3)
C11—S1—N2—C14	67.9 (2)	O1—C2—C3—O2	−0.8 (4)
O3—S1—C11—C10	−174.45 (19)	O1—C2—C3—C4	−179.9 (3)
O3—S1—C11—C12	5.1 (2)	C1—C2—C3—O2	179.9 (3)
O4—S1—C11—C10	−41.7 (2)	C1—C2—C3—C4	0.8 (5)
O4—S1—C11—C12	137.8 (2)	O2—C3—C4—C5	−179.7 (3)
N2—S1—C11—C10	69.8 (2)	C2—C3—C4—C5	−0.6 (5)
N2—S1—C11—C12	−110.7 (2)	C3—C4—C5—C6	−0.2 (5)
C16—O5—N3—C14	−0.8 (3)	C4—C5—C6—C1	0.9 (5)
N3—O5—C16—C15	0.0 (3)	N1—C8—C9—C10	179.8 (2)
N3—O5—C16—C17	−178.6 (2)	C13—C8—C9—C10	−1.6 (4)
C8—N1—C7—C1	−179.0 (2)	N1—C8—C13—C12	−179.5 (3)
C7—N1—C8—C9	−163.9 (3)	C9—C8—C13—C12	2.0 (4)
C7—N1—C8—C13	17.6 (4)	C8—C9—C10—C11	0.8 (4)
S1—N2—C14—N3	−146.5 (2)	C9—C10—C11—S1	179.3 (2)
S1—N2—C14—C15	36.6 (4)	C9—C10—C11—C12	−0.3 (4)
O5—N3—C14—N2	−176.12 (19)	S1—C11—C12—C13	−178.9 (2)
O5—N3—C14—C15	1.3 (3)	C10—C11—C12—C13	0.7 (4)
C6—C1—C2—O1	−179.4 (2)	C11—C12—C13—C8	−1.6 (4)
C6—C1—C2—C3	−0.2 (4)	N2—C14—C15—C16	175.6 (2)
C7—C1—C2—O1	1.2 (4)	N3—C14—C15—C16	−1.3 (3)
C7—C1—C2—C3	−179.6 (3)	C14—C15—C16—O5	0.8 (3)
C2—C1—C6—C5	−0.7 (4)	C14—C15—C16—C17	179.0 (3)
C7—C1—C6—C5	178.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.99 (4)	1.66 (4)	2.588 (3)	155 (3)
O2—H2···O4i	0.79 (4)	2.11 (5)	2.848 (3)	154 (5)
N2—H2A···N3ii	0.84 (3)	2.05 (3)	2.881 (3)	172 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.99 (4)	1.66 (4)	2.588 (3)	155 (3)
O2—H2⋯O4i	0.79 (4)	2.11 (5)	2.848 (3)	154 (5)
N2—H2A⋯N3ii	0.84 (3)	2.05 (3)	2.881 (3)	172 (3)

Symmetry codes: (i) ; (ii) .