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

The title compound, C(18)H(16)BrN(3)O(4)S, is a Schiff base ligand of 5-bromo-salicylaldehyde and sulfisoxazole [or N-(3,4-dimethyl-5-isoxazol)sulfanilamide]. The present structure is a zwitterion and is a more precise reinterpretation of the structure which was originally reported by Hämäläinen, Lehtinen & Turpeinen [Arch. Pharm. (1986), 319, 415-420]. The two aromatic rings which make π-π inter-actions [centroid-centroid distance 3.7538 (18) Å] through intermolecular interactions. There is also a C-Br⋯π inter-action [3.6333 (15) Å] with the heterocyclic ring. An intra-molecular N-H⋯O hydrogen bond also exists. Dimers are formed due to inter-molecular N-H⋯O hydrogen bonding. Inter-molecular C-H⋯O hydrogen bonding links a methyl C atom and the phenolate O atom. The dimers are linked by C-H⋯N hydrogen bonds, where the C atom is from the Schiff base group and the N atom is of five-membered heterocyclic ring.

Related literature

For related literature, see: Chohan et al. (2008 ▶); Hämäläinen et al. (1986 ▶); Shad et al. (2008 ▶).

Experimental

Crystal data

C18H16BrN3O4S

M = 450.31

Monoclinic,

a = 15.3846 (10) Å

b = 7.2235 (5) Å

c = 16.5520 (11) Å

β = 93.201 (4)°

V = 1836.6 (2) Å3

Z = 4

Mo Kα radiation radiation

μ = 2.38 mm−1

T = 296 (2) K

0.18 × 0.14 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.685, T max = 0.793

18874 measured reflections

3955 independent reflections

2704 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.115

S = 1.00

3955 reflections

252 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.62 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 (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800682X/bq2069sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800682X/bq2069Isup2.hkl

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

C18H16BrN3O4S	F000 = 912
Mr = 450.31	Dx = 1.629 Mg m−3
Monoclinic, P21/n	Melting point: 481 K
Hall symbol: -P 2yn	Mo Kα radiation radiation λ = 0.71073 Å
a = 15.3846 (10) Å	Cell parameters from 2704 reflections
b = 7.2235 (5) Å	θ = 1.8–27.0º
c = 16.5520 (11) Å	µ = 2.38 mm−1
β = 93.201 (4)º	T = 296 (2) K
V = 1836.6 (2) Å3	Prismatic, red
Z = 4	0.18 × 0.14 × 0.10 mm

Bruker KappaAPEXII CCD diffractometer	3955 independent reflections
Radiation source: fine-focus sealed tube	2704 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.058
Detector resolution: 7.40 pixels mm-1	θmax = 27.0º
T = 296(2) K	θmin = 1.8º
ω scans	h = −19→19
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −9→9
Tmin = 0.685, Tmax = 0.793	l = −21→18
18874 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) = 0.115	w = 1/[σ2(Fo2) + (0.00.057P)2 + 0.7324P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3955 reflections	Δρmax = 0.46 e Å−3
252 parameters	Δρmin = −0.62 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
Br1	0.11987 (2)	−0.44715 (5)	0.41651 (3)	0.05783 (16)
S1	0.39184 (6)	0.99341 (12)	0.67050 (5)	0.0440 (2)
O1	0.38204 (15)	0.1394 (3)	0.34949 (14)	0.0491 (6)
O2	0.4329 (2)	1.1298 (3)	0.62307 (15)	0.0647 (7)
O3	0.31683 (17)	1.0380 (4)	0.71321 (17)	0.0645 (8)
O4	0.40342 (15)	0.8167 (3)	0.85228 (14)	0.0514 (6)
N1	0.32829 (17)	0.3238 (4)	0.47030 (16)	0.0365 (6)
H1	0.364 (2)	0.300 (5)	0.439 (2)	0.044*
N2	0.46806 (18)	0.9255 (4)	0.73775 (17)	0.0380 (6)
H2	0.510 (2)	0.918 (5)	0.717 (2)	0.046*
N3	0.3987 (2)	0.6529 (5)	0.89824 (19)	0.0669 (10)
C1	0.26586 (19)	0.0371 (4)	0.42687 (18)	0.0352 (7)
C2	0.3239 (2)	0.0154 (4)	0.36301 (19)	0.0382 (7)
C3	0.3146 (2)	−0.1448 (5)	0.3150 (2)	0.0466 (8)
H3	0.3501	−0.1604	0.2718	0.056*
C4	0.2547 (2)	−0.2782 (5)	0.33041 (19)	0.0449 (8)
H4	0.2503	−0.3839	0.2984	0.054*
C5	0.1997 (2)	−0.2558 (5)	0.3945 (2)	0.0416 (7)
C6	0.2043 (2)	−0.1014 (5)	0.4411 (2)	0.0407 (8)
H6	0.1666	−0.0871	0.4826	0.049*
C7	0.2714 (2)	0.1925 (4)	0.47838 (19)	0.0383 (7)
H7	0.2330	0.2017	0.5197	0.046*
C8	0.34005 (19)	0.4812 (4)	0.52001 (18)	0.0329 (7)
C9	0.39958 (18)	0.6121 (4)	0.49609 (18)	0.0349 (7)
H9	0.4295	0.5926	0.4495	0.042*
C10	0.41460 (19)	0.7704 (4)	0.54089 (18)	0.0375 (7)
H10	0.4549	0.8577	0.5255	0.045*
C11	0.3682 (2)	0.7976 (4)	0.60991 (18)	0.0361 (7)
C12	0.3092 (2)	0.6689 (5)	0.63357 (19)	0.0414 (8)
H12	0.2786	0.6893	0.6797	0.050*
C13	0.2952 (2)	0.5096 (5)	0.5892 (2)	0.0411 (8)
H13	0.2558	0.4214	0.6056	0.049*
C14	0.45153 (18)	0.7779 (4)	0.78862 (17)	0.0346 (7)
C15	0.4783 (2)	0.6014 (5)	0.7904 (2)	0.0410 (8)
C16	0.4434 (3)	0.5296 (5)	0.8609 (2)	0.0572 (10)
C17	0.5315 (3)	0.5017 (5)	0.7328 (3)	0.0692 (13)
H17A	0.5086	0.3792	0.7242	0.104*
H17B	0.5906	0.4938	0.7546	0.104*
H17C	0.5300	0.5672	0.6823	0.104*
C18	0.4540 (4)	0.3344 (6)	0.8916 (3)	0.0978 (18)
H18A	0.3996	0.2914	0.9103	0.147*
H18B	0.4976	0.3314	0.9354	0.147*
H18C	0.4714	0.2559	0.8486	0.147*

	U11	U22	U33	U12	U13	U23
Br1	0.0474 (2)	0.0454 (2)	0.0799 (3)	−0.01217 (17)	−0.00429 (19)	−0.00371 (19)
S1	0.0541 (5)	0.0327 (4)	0.0448 (5)	0.0070 (4)	−0.0016 (4)	−0.0070 (4)
O1	0.0517 (13)	0.0490 (14)	0.0487 (13)	−0.0079 (12)	0.0226 (11)	−0.0059 (11)
O2	0.105 (2)	0.0305 (13)	0.0578 (16)	−0.0076 (14)	−0.0076 (15)	0.0067 (12)
O3	0.0561 (15)	0.0677 (18)	0.0693 (17)	0.0268 (13)	−0.0017 (13)	−0.0284 (14)
O4	0.0569 (14)	0.0549 (15)	0.0449 (13)	0.0158 (12)	0.0248 (12)	−0.0003 (12)
N1	0.0342 (14)	0.0397 (15)	0.0362 (15)	−0.0020 (12)	0.0080 (11)	−0.0048 (12)
N2	0.0384 (14)	0.0388 (15)	0.0372 (15)	−0.0013 (12)	0.0068 (12)	−0.0050 (12)
N3	0.083 (2)	0.062 (2)	0.059 (2)	0.0189 (19)	0.0412 (18)	0.0139 (17)
C1	0.0343 (15)	0.0365 (17)	0.0350 (17)	−0.0005 (13)	0.0044 (13)	−0.0045 (14)
C2	0.0399 (17)	0.0392 (18)	0.0357 (17)	0.0051 (14)	0.0052 (14)	−0.0004 (14)
C3	0.058 (2)	0.046 (2)	0.0358 (18)	0.0073 (17)	0.0095 (16)	−0.0042 (16)
C4	0.056 (2)	0.0372 (18)	0.0403 (19)	0.0041 (16)	−0.0072 (16)	−0.0082 (15)
C5	0.0401 (17)	0.0379 (18)	0.0461 (19)	−0.0026 (14)	−0.0036 (15)	0.0010 (15)
C6	0.0347 (16)	0.0437 (19)	0.0440 (19)	−0.0029 (14)	0.0059 (14)	−0.0044 (15)
C7	0.0359 (16)	0.0411 (18)	0.0384 (17)	−0.0021 (14)	0.0066 (14)	−0.0043 (15)
C8	0.0318 (15)	0.0353 (16)	0.0315 (16)	−0.0006 (12)	0.0007 (12)	−0.0019 (13)
C9	0.0348 (16)	0.0408 (17)	0.0294 (16)	−0.0005 (13)	0.0057 (13)	0.0017 (14)
C10	0.0394 (16)	0.0372 (17)	0.0363 (17)	−0.0053 (14)	0.0058 (14)	0.0014 (14)
C11	0.0398 (16)	0.0340 (17)	0.0338 (17)	0.0032 (13)	−0.0032 (13)	−0.0038 (13)
C12	0.0407 (17)	0.048 (2)	0.0365 (17)	−0.0022 (15)	0.0117 (14)	−0.0057 (15)
C13	0.0414 (17)	0.0431 (18)	0.0399 (18)	−0.0120 (14)	0.0126 (15)	−0.0035 (15)
C14	0.0329 (15)	0.0420 (18)	0.0294 (15)	0.0027 (13)	0.0068 (13)	−0.0095 (14)
C15	0.0448 (17)	0.0390 (18)	0.0405 (18)	−0.0009 (14)	0.0132 (15)	−0.0056 (14)
C16	0.067 (2)	0.049 (2)	0.058 (2)	0.0105 (19)	0.025 (2)	0.0077 (18)
C17	0.096 (3)	0.041 (2)	0.076 (3)	0.005 (2)	0.048 (3)	−0.008 (2)
C18	0.140 (5)	0.066 (3)	0.094 (3)	0.028 (3)	0.065 (3)	0.029 (3)

Br1—C5	1.898 (3)	C6—H6	0.9300
S1—O3	1.424 (3)	C7—H7	0.9300
S1—O2	1.429 (3)	C8—C13	1.385 (4)
S1—N2	1.646 (3)	C8—C9	1.389 (4)
S1—C11	1.760 (3)	C9—C10	1.375 (4)
O1—C2	1.294 (4)	C9—H9	0.9300
O4—C14	1.350 (3)	C10—C11	1.395 (4)
O4—N3	1.411 (4)	C10—H10	0.9300
N1—C7	1.302 (4)	C11—C12	1.371 (4)
N1—C8	1.409 (4)	C12—C13	1.376 (5)
N1—H1	0.80 (3)	C12—H12	0.9300
N2—C14	1.391 (4)	C13—H13	0.9300
N2—H2	0.75 (4)	C14—C15	1.339 (4)
N3—C16	1.302 (5)	C15—C16	1.410 (5)
C1—C6	1.406 (4)	C15—C17	1.478 (5)
C1—C7	1.409 (4)	C16—C18	1.504 (6)
C1—C2	1.429 (4)	C17—H17A	0.9600
C2—C3	1.406 (5)	C17—H17B	0.9600
C3—C4	1.368 (5)	C17—H17C	0.9600
C3—H3	0.9300	C18—H18A	0.9600
C4—C5	1.402 (5)	C18—H18B	0.9600
C4—H4	0.9300	C18—H18C	0.9600
C5—C6	1.355 (5)
O3—S1—O2	120.84 (18)	C9—C8—N1	116.6 (3)
O3—S1—N2	107.36 (15)	C10—C9—C8	120.4 (3)
O2—S1—N2	104.87 (16)	C10—C9—H9	119.8
O3—S1—C11	108.49 (16)	C8—C9—H9	119.8
O2—S1—C11	108.95 (16)	C9—C10—C11	118.7 (3)
N2—S1—C11	105.22 (14)	C9—C10—H10	120.7
C14—O4—N3	107.1 (2)	C11—C10—H10	120.7
C7—N1—C8	126.3 (3)	C12—C11—C10	121.1 (3)
C7—N1—H1	114 (3)	C12—C11—S1	120.1 (2)
C8—N1—H1	119 (3)	C10—C11—S1	118.7 (2)
C14—N2—S1	119.4 (2)	C11—C12—C13	120.0 (3)
C14—N2—H2	114 (3)	C11—C12—H12	120.0
S1—N2—H2	108 (3)	C13—C12—H12	120.0
C16—N3—O4	105.9 (3)	C12—C13—C8	119.7 (3)
C6—C1—C7	119.0 (3)	C12—C13—H13	120.2
C6—C1—C2	119.9 (3)	C8—C13—H13	120.2
C7—C1—C2	121.0 (3)	C15—C14—O4	111.2 (3)
O1—C2—C3	121.4 (3)	C15—C14—N2	132.6 (3)
O1—C2—C1	121.2 (3)	O4—C14—N2	116.1 (3)
C3—C2—C1	117.4 (3)	C14—C15—C16	103.8 (3)
C4—C3—C2	121.5 (3)	C14—C15—C17	129.1 (3)
C4—C3—H3	119.3	C16—C15—C17	127.2 (3)
C2—C3—H3	119.3	N3—C16—C15	112.1 (3)
C3—C4—C5	120.1 (3)	N3—C16—C18	122.1 (3)
C3—C4—H4	120.0	C15—C16—C18	125.8 (3)
C5—C4—H4	120.0	C15—C17—H17A	109.5
C6—C5—C4	120.7 (3)	C15—C17—H17B	109.5
C6—C5—Br1	120.2 (3)	H17A—C17—H17B	109.5
C4—C5—Br1	119.0 (3)	C15—C17—H17C	109.5
C5—C6—C1	120.3 (3)	H17A—C17—H17C	109.5
C5—C6—H6	119.8	H17B—C17—H17C	109.5
C1—C6—H6	119.8	C16—C18—H18A	109.5
N1—C7—C1	122.4 (3)	C16—C18—H18B	109.5
N1—C7—H7	118.8	H18A—C18—H18B	109.5
C1—C7—H7	118.8	C16—C18—H18C	109.5
C13—C8—C9	120.1 (3)	H18A—C18—H18C	109.5
C13—C8—N1	123.3 (3)	H18B—C18—H18C	109.5
O3—S1—N2—C14	56.9 (3)	C9—C10—C11—S1	176.4 (2)
O2—S1—N2—C14	−173.4 (2)	O3—S1—C11—C12	−29.4 (3)
C11—S1—N2—C14	−58.5 (3)	O2—S1—C11—C12	−162.7 (3)
C14—O4—N3—C16	0.5 (4)	N2—S1—C11—C12	85.3 (3)
C6—C1—C2—O1	−178.9 (3)	O3—S1—C11—C10	154.8 (3)
C7—C1—C2—O1	−1.4 (5)	O2—S1—C11—C10	21.5 (3)
C6—C1—C2—C3	1.8 (5)	N2—S1—C11—C10	−90.5 (3)
C7—C1—C2—C3	179.3 (3)	C10—C11—C12—C13	0.2 (5)
O1—C2—C3—C4	178.3 (3)	S1—C11—C12—C13	−175.5 (3)
C1—C2—C3—C4	−2.3 (5)	C11—C12—C13—C8	−0.9 (5)
C2—C3—C4—C5	1.0 (5)	C9—C8—C13—C12	0.7 (5)
C3—C4—C5—C6	0.9 (5)	N1—C8—C13—C12	−178.7 (3)
C3—C4—C5—Br1	−177.9 (3)	N3—O4—C14—C15	−0.2 (4)
C4—C5—C6—C1	−1.4 (5)	N3—O4—C14—N2	−176.6 (3)
Br1—C5—C6—C1	177.4 (2)	S1—N2—C14—C15	105.7 (4)
C7—C1—C6—C5	−177.5 (3)	S1—N2—C14—O4	−78.9 (3)
C2—C1—C6—C5	0.0 (5)	O4—C14—C15—C16	−0.1 (4)
C8—N1—C7—C1	−178.3 (3)	N2—C14—C15—C16	175.5 (4)
C6—C1—C7—N1	178.1 (3)	O4—C14—C15—C17	179.7 (4)
C2—C1—C7—N1	0.6 (5)	N2—C14—C15—C17	−4.7 (7)
C7—N1—C8—C13	4.9 (5)	O4—N3—C16—C15	−0.6 (5)
C7—N1—C8—C9	−174.5 (3)	O4—N3—C16—C18	−180.0 (4)
C13—C8—C9—C10	0.1 (5)	C14—C15—C16—N3	0.5 (5)
N1—C8—C9—C10	179.6 (3)	C17—C15—C16—N3	−179.4 (4)
C8—C9—C10—C11	−0.8 (5)	C14—C15—C16—C18	179.8 (5)
C9—C10—C11—C12	0.6 (5)	C17—C15—C16—C18	0.0 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.80 (3)	1.91 (3)	2.577 (4)	141 (3)
N2—H2···O1i	0.75 (3)	2.09	2.828 (4)	171 (4)
C17—H17C···O1i	0.96	2.58	3.248 (5)	126
C7—H7···N3ii	0.93	2.53	3.420 (4)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.80 (3)	1.91 (3)	2.577 (4)	141 (3)
N2—H2⋯O1i	0.75 (3)	2.09	2.828 (4)	171 (4)
C17—H17C⋯O1i	0.96	2.58	3.248 (5)	126
C7—H7⋯N3ii	0.93	2.53	3.420 (4)	161

Symmetry codes: (i) ; (ii) .