4-Chloro-2-[(E)-({4-[N-(3,4-dimethyl-isoxazol-5-yl)sulfamo-yl]phen-yl}iminio)meth-yl]phenolate.

The title compound, C(18)H(16)ClN(3)O(4)S, is a Schiff base ligand in which the H atom of the hydr-oxy group has moved to the N atom of the imine group, resulting in a zwitterion. The structure is stabilized by an intra-molecular (N-H⋯O) and five inter-molecular (C-H⋯O, C-H⋯N and N-H⋯O) hydrogen bonds. The mol-ecules are linked to each other by hydrogen bonds and form a three-dimensional polymeric network. In addition, the aromatic rings are also involved in π-π inter-actions [centroid-centroid distance between aromatic rings = 3.7525 (11) Å].

Related literature

For related literature, see: Chatterjee et al. (1982 ▶); Chohan et al. (2008 ▶); Hämäläinen et al. (1986 ▶); Nishimori et al. (2005 ▶).

Experimental

Crystal data

C18H16ClN3O4S

M = 405.85

Monoclinic,

a = 15.1871 (6) Å

b = 7.2555 (3) Å

c = 16.6267 (7) Å

β = 94.081 (2)°

V = 1827.45 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 296 (2) K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.886, T max = 0.935

18429 measured reflections

4669 independent reflections

3443 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.127

S = 1.04

3443 reflections

250 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); 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 class="Chemical">N (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005321/pv2068sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005321/pv2068Isup2.hkl

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

C18H16ClN3O4S	F000 = 840
Mr = 405.85	Dx = 1.475 Mg m−3
Monoclinic, P21/n	Melting point: 509 K
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71073 Å
a = 15.1871 (6) Å	Cell parameters from 2465 reflections
b = 7.2555 (3) Å	θ = 2.2–28.7º
c = 16.6267 (7) Å	µ = 0.35 mm−1
β = 94.081 (2)º	T = 296 (2) K
V = 1827.45 (13) Å3	Prismatic, red
Z = 4	0.30 × 0.25 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	4669 independent reflections
Radiation source: fine-focus sealed tube	3443 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
Detector resolution: 7.40 pixels mm-1	θmax = 28.6º
T = 296(2) K	θmin = 1.8º
ω scans	h = −20→20
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −9→9
Tmin = 0.886, Tmax = 0.935	l = −22→22
18429 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0619P)2 + 0.5575P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3443 reflections	Δρmax = 0.38 e Å−3
250 parameters	Δρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Cl1	0.87797 (4)	−0.43370 (8)	0.58505 (4)	0.06440 (19)
S1	0.60762 (4)	0.99136 (7)	0.32843 (3)	0.04563 (15)
O1	0.62180 (10)	0.1417 (2)	0.64974 (8)	0.0504 (4)
O2	0.68281 (11)	1.0347 (2)	0.28554 (11)	0.0678 (5)
O3	0.56667 (13)	1.1279 (2)	0.37529 (10)	0.0676 (5)
O4	0.59283 (10)	0.8115 (2)	0.14720 (8)	0.0529 (4)
N1	0.67536 (10)	0.3239 (2)	0.52967 (9)	0.0368 (3)
H1	0.6445 (13)	0.312 (3)	0.5715 (13)	0.044*
N2	0.52879 (11)	0.9215 (2)	0.26153 (10)	0.0400 (4)
H2	0.4845 (15)	0.908 (3)	0.2832 (13)	0.048*
N3	0.59687 (15)	0.6461 (3)	0.10209 (12)	0.0666 (6)
C1	0.73875 (12)	0.0376 (3)	0.57297 (11)	0.0378 (4)
C2	0.68045 (13)	0.0167 (3)	0.63625 (11)	0.0395 (4)
C3	0.68941 (15)	−0.1451 (3)	0.68403 (12)	0.0471 (5)
H3	0.6540	−0.1608	0.7269	0.057*
C4	0.74946 (15)	−0.2786 (3)	0.66788 (12)	0.0496 (5)
H4	0.7533	−0.3850	0.6991	0.059*
C5	0.80496 (13)	−0.2571 (3)	0.60509 (12)	0.0449 (4)
C6	0.80079 (12)	−0.1021 (3)	0.55890 (12)	0.0438 (4)
H6	0.8389	−0.0879	0.5179	0.053*
C7	0.73313 (12)	0.1937 (3)	0.52144 (11)	0.0392 (4)
H7	0.7717	0.2033	0.4807	0.047*
C8	0.66304 (11)	0.4819 (2)	0.48013 (10)	0.0343 (4)
C9	0.60243 (11)	0.6121 (3)	0.50340 (10)	0.0360 (4)
H9	0.5724	0.5928	0.5495	0.043*
C10	0.58692 (12)	0.7701 (3)	0.45801 (11)	0.0388 (4)
H10	0.5463	0.8572	0.4732	0.047*
C11	0.63252 (12)	0.7973 (3)	0.38967 (10)	0.0366 (4)
C12	0.69331 (13)	0.6678 (3)	0.36602 (11)	0.0425 (4)
H12	0.7239	0.6883	0.3203	0.051*
C13	0.70799 (13)	0.5089 (3)	0.41075 (11)	0.0423 (4)
H13	0.7475	0.4206	0.3947	0.051*
C14	0.54518 (11)	0.7736 (3)	0.21080 (10)	0.0373 (4)
C15	0.51814 (13)	0.5968 (3)	0.20979 (11)	0.0417 (4)
C16	0.55223 (16)	0.5232 (3)	0.13954 (13)	0.0537 (5)
C17	0.46521 (19)	0.4975 (3)	0.26793 (16)	0.0662 (7)
H17A	0.4152	0.4405	0.2394	0.099*
H17B	0.4453	0.5832	0.3067	0.099*
H17C	0.5010	0.4045	0.2952	0.099*
C18	0.5413 (2)	0.3294 (4)	0.10901 (18)	0.0851 (9)
H18A	0.5263	0.3313	0.0519	0.128*
H18B	0.4951	0.2697	0.1357	0.128*
H18C	0.5956	0.2631	0.1198	0.128*

	U11	U22	U33	U12	U13	U23
Cl1	0.0529 (3)	0.0449 (3)	0.0932 (5)	0.0139 (2)	−0.0106 (3)	0.0027 (3)
S1	0.0563 (3)	0.0317 (2)	0.0478 (3)	−0.0073 (2)	−0.0044 (2)	0.0078 (2)
O1	0.0551 (8)	0.0479 (8)	0.0507 (8)	0.0055 (7)	0.0206 (7)	0.0053 (6)
O2	0.0592 (9)	0.0676 (11)	0.0756 (11)	−0.0261 (8)	−0.0034 (8)	0.0294 (9)
O3	0.1035 (13)	0.0312 (8)	0.0657 (10)	0.0075 (8)	−0.0100 (9)	−0.0040 (7)
O4	0.0582 (9)	0.0546 (9)	0.0484 (8)	−0.0151 (7)	0.0214 (7)	0.0025 (7)
N1	0.0385 (8)	0.0379 (8)	0.0343 (7)	0.0015 (6)	0.0054 (6)	0.0063 (6)
N2	0.0404 (8)	0.0388 (9)	0.0407 (8)	−0.0005 (7)	0.0033 (7)	0.0074 (7)
N3	0.0833 (14)	0.0628 (13)	0.0581 (11)	−0.0124 (11)	0.0358 (10)	−0.0091 (10)
C1	0.0368 (9)	0.0371 (10)	0.0389 (9)	0.0000 (7)	−0.0002 (7)	0.0046 (7)
C2	0.0434 (10)	0.0396 (10)	0.0352 (9)	−0.0060 (8)	0.0006 (7)	−0.0005 (7)
C3	0.0613 (12)	0.0411 (11)	0.0393 (10)	−0.0094 (9)	0.0056 (9)	0.0045 (8)
C4	0.0646 (13)	0.0362 (10)	0.0456 (11)	−0.0067 (9)	−0.0124 (9)	0.0088 (8)
C5	0.0409 (10)	0.0388 (10)	0.0530 (11)	0.0032 (8)	−0.0103 (8)	0.0002 (9)
C6	0.0382 (9)	0.0440 (11)	0.0495 (11)	0.0044 (8)	0.0050 (8)	0.0056 (9)
C7	0.0380 (9)	0.0399 (10)	0.0402 (9)	0.0019 (8)	0.0071 (7)	0.0053 (8)
C8	0.0344 (8)	0.0353 (9)	0.0329 (8)	−0.0015 (7)	0.0004 (7)	0.0024 (7)
C9	0.0369 (9)	0.0403 (10)	0.0311 (8)	0.0004 (7)	0.0041 (7)	0.0002 (7)
C10	0.0407 (9)	0.0360 (10)	0.0396 (9)	0.0043 (8)	0.0025 (7)	−0.0031 (7)
C11	0.0408 (9)	0.0318 (9)	0.0366 (9)	−0.0027 (7)	−0.0019 (7)	0.0037 (7)
C12	0.0440 (10)	0.0475 (11)	0.0372 (9)	0.0026 (8)	0.0100 (8)	0.0072 (8)
C13	0.0434 (10)	0.0439 (11)	0.0407 (9)	0.0104 (8)	0.0104 (8)	0.0051 (8)
C14	0.0345 (8)	0.0433 (10)	0.0344 (8)	−0.0016 (7)	0.0049 (7)	0.0088 (7)
C15	0.0440 (10)	0.0384 (10)	0.0438 (10)	0.0004 (8)	0.0102 (8)	0.0071 (8)
C16	0.0598 (13)	0.0524 (13)	0.0509 (12)	−0.0057 (10)	0.0174 (10)	−0.0027 (10)
C17	0.0873 (18)	0.0405 (12)	0.0762 (16)	−0.0041 (12)	0.0425 (14)	0.0115 (11)
C18	0.118 (2)	0.0623 (17)	0.0799 (18)	−0.0154 (17)	0.0424 (18)	−0.0195 (14)

Cl1—C5	1.742 (2)	C6—H6	0.9300
S1—O2	1.4238 (17)	C7—H7	0.9300
S1—O3	1.4298 (17)	C8—C9	1.393 (2)
S1—N2	1.6545 (17)	C8—C13	1.395 (2)
S1—C11	1.7630 (18)	C9—C10	1.383 (3)
O1—C2	1.302 (2)	C9—H9	0.9300
O4—C14	1.351 (2)	C10—C11	1.386 (2)
O4—N3	1.419 (2)	C10—H10	0.9300
N1—C7	1.303 (2)	C11—C12	1.393 (3)
N1—C8	1.416 (2)	C12—C13	1.382 (3)
N1—H1	0.87 (2)	C12—H12	0.9300
N2—C14	1.399 (2)	C13—H13	0.9300
N2—H2	0.79 (2)	C14—C15	1.346 (3)
N3—C16	1.305 (3)	C15—C16	1.415 (3)
C1—C6	1.415 (3)	C15—C17	1.487 (3)
C1—C7	1.419 (3)	C16—C18	1.501 (3)
C1—C2	1.431 (2)	C17—H17A	0.9600
C2—C3	1.419 (3)	C17—H17B	0.9600
C3—C4	1.370 (3)	C17—H17C	0.9600
C3—H3	0.9300	C18—H18A	0.9600
C4—C5	1.396 (3)	C18—H18B	0.9600
C4—H4	0.9300	C18—H18C	0.9600
C5—C6	1.361 (3)
O2—S1—O3	121.02 (11)	C13—C8—N1	122.83 (16)
O2—S1—N2	107.38 (10)	C10—C9—C8	120.05 (16)
O3—S1—N2	104.86 (10)	C10—C9—H9	120.0
O2—S1—C11	108.61 (10)	C8—C9—H9	120.0
O3—S1—C11	108.80 (9)	C9—C10—C11	119.31 (17)
N2—S1—C11	105.00 (8)	C9—C10—H10	120.3
C14—O4—N3	106.69 (15)	C11—C10—H10	120.3
C7—N1—C8	126.00 (15)	C10—C11—C12	121.02 (17)
C7—N1—H1	114.5 (14)	C10—C11—S1	119.21 (14)
C8—N1—H1	119.4 (14)	C12—C11—S1	119.64 (13)
C14—N2—S1	119.29 (13)	C13—C12—C11	119.70 (16)
C14—N2—H2	111.7 (17)	C13—C12—H12	120.1
S1—N2—H2	109.3 (16)	C11—C12—H12	120.1
C16—N3—O4	106.39 (16)	C12—C13—C8	119.50 (17)
C6—C1—C7	118.96 (16)	C12—C13—H13	120.3
C6—C1—C2	119.99 (17)	C8—C13—H13	120.3
C7—C1—C2	121.00 (17)	C15—C14—O4	111.35 (17)
O1—C2—C3	121.31 (17)	C15—C14—N2	132.18 (16)
O1—C2—C1	121.30 (17)	O4—C14—N2	116.35 (16)
C3—C2—C1	117.38 (18)	C14—C15—C16	103.91 (17)
C4—C3—C2	120.93 (18)	C14—C15—C17	129.22 (19)
C4—C3—H3	119.5	C16—C15—C17	126.9 (2)
C2—C3—H3	119.5	N3—C16—C15	111.7 (2)
C3—C4—C5	120.87 (18)	N3—C16—C18	121.8 (2)
C3—C4—H4	119.6	C15—C16—C18	126.5 (2)
C5—C4—H4	119.6	C15—C17—H17A	109.5
C6—C5—C4	120.53 (19)	C15—C17—H17B	109.5
C6—C5—Cl1	120.31 (16)	H17A—C17—H17B	109.5
C4—C5—Cl1	119.15 (16)	C15—C17—H17C	109.5
C5—C6—C1	120.25 (18)	H17A—C17—H17C	109.5
C5—C6—H6	119.9	H17B—C17—H17C	109.5
C1—C6—H6	119.9	C16—C18—H18A	109.5
N1—C7—C1	121.81 (16)	C16—C18—H18B	109.5
N1—C7—H7	119.1	H18A—C18—H18B	109.5
C1—C7—H7	119.1	C16—C18—H18C	109.5
C9—C8—C13	120.42 (16)	H18A—C18—H18C	109.5
C9—C8—N1	116.75 (15)	H18B—C18—H18C	109.5
O2—S1—N2—C14	56.27 (16)	C9—C10—C11—S1	176.02 (14)
O3—S1—N2—C14	−173.81 (14)	O2—S1—C11—C10	155.29 (15)
C11—S1—N2—C14	−59.20 (15)	O3—S1—C11—C10	21.74 (19)
C14—O4—N3—C16	0.6 (2)	N2—S1—C11—C10	−90.09 (16)
C6—C1—C2—O1	−178.92 (18)	O2—S1—C11—C12	−28.85 (19)
C7—C1—C2—O1	−1.5 (3)	O3—S1—C11—C12	−162.40 (16)
C6—C1—C2—C3	1.4 (3)	N2—S1—C11—C12	85.77 (17)
C7—C1—C2—C3	178.83 (18)	C10—C11—C12—C13	0.6 (3)
O1—C2—C3—C4	177.98 (19)	S1—C11—C12—C13	−175.17 (16)
C1—C2—C3—C4	−2.4 (3)	C11—C12—C13—C8	−1.4 (3)
C2—C3—C4—C5	1.5 (3)	C9—C8—C13—C12	1.3 (3)
C3—C4—C5—C6	0.4 (3)	N1—C8—C13—C12	−179.16 (18)
C3—C4—C5—Cl1	−178.14 (16)	N3—O4—C14—C15	−0.2 (2)
C4—C5—C6—C1	−1.3 (3)	N3—O4—C14—N2	−176.68 (17)
Cl1—C5—C6—C1	177.20 (15)	S1—N2—C14—C15	105.9 (2)
C7—C1—C6—C5	−177.06 (18)	S1—N2—C14—O4	−78.51 (19)
C2—C1—C6—C5	0.4 (3)	O4—C14—C15—C16	−0.2 (2)
C8—N1—C7—C1	−178.19 (17)	N2—C14—C15—C16	175.5 (2)
C6—C1—C7—N1	177.69 (19)	O4—C14—C15—C17	179.5 (2)
C2—C1—C7—N1	0.3 (3)	N2—C14—C15—C17	−4.7 (4)
C7—N1—C8—C9	−174.85 (18)	O4—N3—C16—C15	−0.7 (3)
C7—N1—C8—C13	5.6 (3)	O4—N3—C16—C18	179.6 (3)
C13—C8—C9—C10	−0.5 (3)	C14—C15—C16—N3	0.6 (3)
N1—C8—C9—C10	179.96 (16)	C17—C15—C16—N3	−179.2 (2)
C8—C9—C10—C11	−0.3 (3)	C14—C15—C16—C18	−179.8 (3)
C9—C10—C11—C12	0.2 (3)	C17—C15—C16—C18	0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.87 (2)	1.85 (2)	2.574 (2)	140 (2)
C7—H7···N3i	0.93	2.54	3.429 (3)	161
C12—H12···O2i	0.93	2.59	3.391 (3)	145
C17—H17C···O3ii	0.96	2.57	3.516 (3)	168
C17—H17B···O1iii	0.96	2.38	3.276 (3)	156
N2—H2···O1iii	0.79 (2)	2.06 (2)	2.846 (2)	173 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.87 (2)	1.85 (2)	2.574 (2)	140 (2)
C7—H7⋯N3i	0.93	2.54	3.429 (3)	161
C12—H12⋯O2i	0.93	2.59	3.391 (3)	145
C17—H17C⋯O3ii	0.96	2.57	3.516 (3)	168
C17—H17B⋯O1iii	0.96	2.38	3.276 (3)	156
N2—H2⋯O1iii	0.79 (2)	2.06 (2)	2.846 (2)	173 (2)

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