4-Chloro-2-[(E)-({4-[N-(3,4-dimethyl­isoxazol-5-yl)sulfamo­yl]phen­yl}iminio)meth­yl]phenolate

Shad, H.A.; Chohan, Z.H.; Tahir, M.N.; Khan, I.U.

doi:10.1107/S1600536808005321

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o635

doi:10.1107/S1600536808005321

Open

access

4-Chloro-2-[(E)-({4-[N-(3,4-dimethylisoxazol-5-yl)sulfamoyl]phenyl}iminio)methyl]phenolate

Hazoor A. Shad,^a Zahid H. Chohan,^a M. Nawaz Tahir ^b and Islam Ullah Khan ^c ^*

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and ^cGovernment College University, Department of Chemistry, Lahore, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 1 February 2008; accepted 25 February 2008; online 27 February 2008)

The title compound, C₁₈H₁₆ClN₃O₄S, is a Schiff base ligand in which the H atom of the hydroxy group has moved to the N atom of the imine group, resulting in a zwitterion. The structure is stabilized by an intramolecular (N—H⋯O) and five intermolecular (C—H⋯O, C—H⋯N and N—H⋯O) hydrogen bonds. The molecules 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 interactions [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_r = 405.85
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.127
S = 1.04
3443 reflections
250 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) -x+1, -y+1, -z+1.

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.

Supporting information

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

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

checkCIF report

Comment top

Sulfonamides have been found to possess a wide range of medicinal properties such as antibacterial, antitumor, diuretic, anti-carbonic anhydrase, hypoglycaemic, anti-thyroid and protease inhibitor (Nishimori et al., 2005). In view of the versatile chemistry of various derivatives of sulfonamides, a continuous effort of synthesizing Schiff base ligands of substituted halogen salicylaldehyde and various sulfonamides (Chohan et al., 2008) is in progress. In the same context, we herein report the structure of the title compound, (I), derived from the reaction of sulfisoxazole [N-(3,4-dimethyl-5-isoxazol)sulfanilamide] and 5-chlorosalicylaldehyde. The crystal structures of sulfisoxazole (Chatterjee et al., 1982) and a bromo analog of (I) (Hämäläinen et al., 1986) have already been published; the later is isomorphous with (I).

In the solid state the H-atom bonded to hydroxy group in (I) has shifted to N-atom of the Schiff base moiety, resulting in the formation of a zwitterion (Fig. 1). The bond distance C2—O1 [1.302 (2) Å] in (I) compares well with 1.295 (10) Å reported for the corresponding distance in the bromo-analog. The bond lengths in the aromatic rings in (I) are similar to the corresonding bond lengths reported in its bromo-isomorph. The range of bond angles around S-atom [104.86 (10)°-121.02 (11)°] in (I) is also the same as reported [104.5 (4)°-121.2 (4)°] in the bromo-analog (Hämäläinen et al., 1986). The structure is stabilized by an intramolecular and five intermolecular H-bondings, the details of H-bonds are given in Table 1. The molecules linked to each other by H-bonds form a three-dimensional polymeric network (Fig. 2). In addition, π-π interactions between aromatic rings C8—C13 (ring A) and C1—C6 (ring B) are also observed with distance between the centers of gravity for the two rings CgA···CgB^iv (iv = x, y - 1, z) being Å. There also exists a π interaction between five-membered heterocyclic ring (ring C) and Cl1 with Cl1···CgC^v [v = x - 1/2, -y - 1/2, z - 1/2] distance of 3.5371 (11) Å. The dihedral angles between the rings A/B, A/C, B/C have values of 5.84 (9), 43.37 (11), and 43.29 (11)°, respectively.

Related literature top

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

Experimental top

An ethanol solution (15 ml) of sulfisoxazole (0.5346 g, 2 mmol) was added to a solution of 5-chlorosalicylaldehyde (0.3131 g, 2 mmol) in ethanol (10 ml). The reaction mixture was refluxed for 3 h. The solution was cooled to room temperature, filtered and volume reduced to about one-third using rotary evaporator. It was then allowed to stand for 13 days, after which orange-red crystals were obtained (m.p. 509 K).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); 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 (Spek, 2003).

Figures top

	Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of (I) with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. The intramolecular H-bonding is shown by dashed lines.
	Fig. 2. The unit cell packing of (I) (Spek, 2003) showing the interamolecular and intermolecular H-bonds leading to three-dimensional network.

4-Chloro-2-[(E)-({4-[N-(3,4-dimethylisoxazol-5- yl)sulfamoyl]phenyl}iminio)methyl]phenolate top

Crystal data top

C₁₈H₁₆ClN₃O₄S	F(000) = 840
M_r = 405.85	D_x = 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 = 2.2–28.7°
c = 16.6267 (7) Å	µ = 0.35 mm⁻¹
β = 94.081 (2)°	T = 296 K
V = 1827.45 (13) Å³	Prismatic, red
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4669 independent reflections
Radiation source: fine-focus sealed tube	3443 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.6°, θ_min = 1.8°
ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
T_min = 0.886, T_max = 0.935	l = −22→22
18429 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0619P)² + 0.5575P] where P = (F_o² + 2F_c²)/3
3443 reflections	(Δ/σ)_max = 0.001
250 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₈H₁₆ClN₃O₄S	V = 1827.45 (13) Å³
M_r = 405.85	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.1871 (6) Å	µ = 0.35 mm⁻¹
b = 7.2555 (3) Å	T = 296 K
c = 16.6267 (7) Å	0.30 × 0.25 × 0.20 mm
β = 94.081 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4669 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3443 reflections with I > 2σ(I)
T_min = 0.886, T_max = 0.935	R_int = 0.028
18429 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.38 e Å⁻³
3443 reflections	Δρ_min = −0.23 e Å⁻³
250 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆ClN₃O₄S
M_r	405.85
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	15.1871 (6), 7.2555 (3), 16.6267 (7)
β (°)	94.081 (2)
V (Å³)	1827.45 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.886, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	18429, 4669, 3443
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.674

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.127, 1.04
No. of reflections	3443
No. of parameters	250
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.23

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) −x+1, −y+1, −z+1.

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer.

References

Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsion, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsion, USA. Google Scholar
Chatterjee, C., Dattagupta, J. K. & Saha, N. N. (1982). Acta Cryst. B38, 1845–1847. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Chohan, Z. H., Shad, H. A., Tahir, M. N. & Khan, I. U. (2008). Acta Cryst. E64 Submitted. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hämäläinen, R., Lehtinen, M. & Turpeinen, U. (1986). Arch. Pharm. 319, 415–420. Google Scholar
Nishimori, I., Vullo, D., Innocenti, A., Scozzafava, A., Mastrolorenz, A. & Supuran, C. T. (2005). Bioorg. Med. Chem. Lett. 15, 3828–3833. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o635

doi:10.1107/S1600536808005321

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

4-Chloro-2-[(E)-({4-[N-(3,4-di­methyl­isoxazol-5-yl)sulfamo­yl]phen­yl}iminio)meth­yl]phenolate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-Chloro-2-[(E)-({4-[N-(3,4-dimethylisoxazol-5-yl)sulfamoyl]phenyl}iminio)methyl]phenolate