4-[(2-Hy­droxy­benzyl­idene)amino]-N-(5-methyl­isoxazol-3-yl)benzene­sulfonamide: a monoclinic polymorph

Ebenezer, S.; Muthiah, P.T.

doi:10.1107/S1600536810036585

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2574

doi:10.1107/S1600536810036585

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4-[(2-Hydroxybenzylidene)amino]-N-(5-methylisoxazol-3-yl)benzenesulfonamide: a monoclinic polymorph

Samuel Ebenezer ^a and Packianathan Thomas Muthiah ^a ^*

^aSchool of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, Tamilnadu, India
^*Correspondence e-mail: tommtrichy@yahoo.co.in

(Received 25 August 2010; accepted 13 September 2010; online 18 September 2010)

The title compound, C₁₇H₁₅N₃O₄S, is a monoclinic polymorph with space group P2₁/c of the previously reported triclinic form in P $[\overline{1}]$ [Subashini et al. (2009 ). J. Chem. Crystallogr. 39, 112–116]. In both polymorphs, intramolecular O—H⋯N hydrogen bonds and dimer formation via a pair of intermolecular N—H⋯N hydrogen bonds with an R₂²(8) motif are observed. The two polymorphs differ in the next level of supramolecular organization involving C—H⋯O hydrogen bonds with varied packing and different conformations.

Related literature

For the biological relevance of sulfonamide drugs and their Schiff base derivatives, see: Genc et al. (2008 ); Supuran et al. (1997 ). For the triclinic polymorph of the title compound, see: Subashini et al. (2009). For $[R_{2}^{2}]$ (8) ring motifs in sulfonamides, see: Adsmond & Grant (2001 ). For conformational studies on sulfonamides, see: Kálmán et al. (1981 ).

Experimental

Crystal data

C₁₇H₁₅N₃O₄S
M_r = 357.39
Monoclinic, P 2₁ /c
a = 7.0374 (1) Å
b = 17.9244 (3) Å
c = 14.5175 (3) Å
β = 112.962 (1)°
V = 1686.15 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.947, T_max = 0.957
14935 measured reflections
2953 independent reflections
2198 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.115
S = 1.06
2953 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.25 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
O1—H1⋯N1	0.82	1.88	2.606 (3)	147
N2—H2A⋯N3ⁱ	0.86	2.24	2.898 (4)	134
C10—H10⋯O1ⁱⁱ	0.93	2.53	3.313 (3)	141
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036585/is2595sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810036585/is2595Isup2.hkl

checkCIF report

Comment top

Sulfonamide drugs are known to have antibacterial, antifungal,antimalarial and antileprotic properties (Genc et al., 2008). Schiff bases derived from sulfonamide compounds also display enzymatic inhibition (Supuran et al., 1997). A polymorph, I, of the title compound has been reported earlier from our group (Subashini et al., 2009). In the present study we report a new dimorph, II, and its crystal structure.

The new dimorph crystallizes in monoclinic system (P2₁/c) which contains only one molecule in the asymmetric unit (Fig. 1). There is one N—H···N intermolecular hydrogen bond [N2···N3 = 2.899 (3) Å; Table 1], where the amido nitrogen acts as a donor and the nitrogen of the isoxazole acts as an acceptor. The donor and acceptor of one of the Schiff base molecule pair up with another inversely related molecule to form a dimer with graph set notation R₂²(8) (Fig 2). A similar type of homosynthon is also formed in the polymorph I. A recent statistical survey has shown that the absence of amino group in the sulfonamide compounds further encourages amido protons to hydrogen bond with an activated nitrogen (atom of a heterocycle that lies in conjugation with the amido nitrogen) of the heterocyclic ring to form an optimum sized R₂²(8) ring motif (Adsmond & Grant, 2001). This could be the reason why both the polymorphs form the same synthons thereby succumb to similar first order arrangement of molecules.

Polymorph II forms an intramolecular C—H···O bond with a graph set notation S(6) similar to its predecessor. It is only the weaker bonds in both the polymorphs that are significantly responsible for the differences in arrangement of molecules in the crystal. In both the polymorphs the homosynthon combines with each other through a couple of weak C—H···O bonds (C10—H10···O1 in polymorph II) forming a large ring motif with graph set notation R₄⁴(12) and R₄⁴(14) for polymorphs I and II respectively. These homosynthons stretch along a particular direction linked through weak C—H···O interaction forming a supramolecular chain (Fig. 3).

In addition to the packing differences there are changes in the conformations of the molecules which are obvious from their torsion angles. Though there are many possible conformations in which the molecule could exist, the steric and electrostatic constraints of sulfonamides have restricted them to torsion angles between 70–120° and 60–90° for ε1 and ε2 respectively [where ε1 and ε2 are the modulus of the torsion angles along C—S and S—N bonds respectively] (Kálmán et al., 1981). The angles ε1 and ε2 for polymorph II lie in the expected range. The bond lengths and the bond angles among the polymorphs are more or less close to one another but differ hugely in their torsion angles.

To conclude with, both dimorphs posses same intermolecular hydrogen bonds leading to formation of dimers through N—H···N hydrogen bonds, showing similar first level of organization. They differ only in the higher level supramolecular organization through C—H···O hydrogen bonds. A thorough inspection reveals that conformational changes in the molecule lead to the packing differences between the dimorphs.

Related literature top

For the biological relevance of sulfonamide drugs and their Schiff base derivatives, see: Genc et al. (2008); Supuran et al. (1997). For the triclinic polymorph of the title compound, see: Subashini et al. (2009). For R₂²(8) ring motifs in sulfonamides, see: Adsmond & Grant (2001). For conformational studies on sulfonamides, see: Kálmán et al. (1981).

Experimental top

The base of the title compound was synthesized by refluxing ethanolic solutions of 4-amino-N-(5-methyl-3-isoxazolyl) benzene sulfonamide (SMZ) (25 mg, Qualigens) with 2-hydroxy benzaldehyde (SA) (25 mg, LOBA Chemie) in an equimolar ratio. The mixture was refluxed for up to 6 h and then transferred to a beaker which was eventually allowed to evaporate slowly in the mother liquor. After a couple of days yellow crystals separated out. This base was characterized using single-crystal XRD method and found to be a new polymorph.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. An ORTEP view of new dimorph showing 50% probability displacement ellipsoids.
	Fig. 2. Two inversely related molecules form dimer through R₂²(8) motif. [Symmetry code: (i) -x + 2, -y + 1, -z + 2.]
	Fig. 3. View of supramolecular chain formed through the dimers via weak C—H···O interactions.

4-[(2-Hydroxybenzylidene)amino]-N-(5-methylisoxazol-3- yl)benzenesulfonamide top

Crystal data top

C₁₇H₁₅N₃O₄S	F(000) = 744
M_r = 357.39	D_x = 1.408 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2953 reflections
a = 7.0374 (1) Å	θ = 1.9–25.0°
b = 17.9244 (3) Å	µ = 0.22 mm⁻¹
c = 14.5175 (3) Å	T = 293 K
β = 112.962 (1)°	PRISM, yellow
V = 1686.15 (5) Å³	0.25 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2953 independent reflections
Radiation source: fine-focus sealed tube	2198 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −7→8
T_min = 0.947, T_max = 0.957	k = −19→21
14935 measured reflections	l = −17→17

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.040P)² + 0.9817P] where P = (F_o² + 2F_c²)/3
2953 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₇H₁₅N₃O₄S	V = 1686.15 (5) Å³
M_r = 357.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.0374 (1) Å	µ = 0.22 mm⁻¹
b = 17.9244 (3) Å	T = 293 K
c = 14.5175 (3) Å	0.25 × 0.22 × 0.20 mm
β = 112.962 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2953 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2198 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.957	R_int = 0.038
14935 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.06	Δρ_max = 0.25 e Å⁻³
2953 reflections	Δρ_min = −0.30 e Å⁻³
227 parameters

Special details top

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 on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
S1	0.61583 (11)	0.37355 (3)	0.87561 (5)	0.0507 (3)
O1	0.8540 (3)	0.47399 (10)	0.37502 (16)	0.0676 (8)
O2	0.3998 (3)	0.38398 (10)	0.84707 (15)	0.0625 (7)
O3	0.7159 (3)	0.30911 (10)	0.93038 (15)	0.0667 (8)
O4	0.7150 (3)	0.63662 (10)	0.93497 (15)	0.0658 (7)
N1	0.8210 (4)	0.39344 (12)	0.51746 (17)	0.0551 (8)
N2	0.7352 (3)	0.44313 (11)	0.94686 (16)	0.0501 (8)
N3	0.8188 (4)	0.56808 (12)	0.96244 (18)	0.0594 (9)
C1	0.9847 (4)	0.42129 (14)	0.3684 (2)	0.0528 (10)
C2	1.0800 (5)	0.43213 (17)	0.3024 (2)	0.0664 (11)
C3	1.2136 (6)	0.38013 (19)	0.2939 (3)	0.0770 (14)
C4	1.2539 (6)	0.31558 (19)	0.3500 (3)	0.0787 (16)
C5	1.1614 (5)	0.30449 (15)	0.4157 (2)	0.0650 (11)
C6	1.0262 (4)	0.35658 (13)	0.4270 (2)	0.0495 (9)
C7	0.9426 (4)	0.34594 (15)	0.5023 (2)	0.0549 (10)
C8	0.7705 (4)	0.38551 (14)	0.6022 (2)	0.0506 (9)
C9	0.5773 (4)	0.40732 (14)	0.5957 (2)	0.0544 (10)
C10	0.5264 (4)	0.40347 (14)	0.6783 (2)	0.0511 (10)
C11	0.6728 (4)	0.37909 (13)	0.7690 (2)	0.0459 (8)
C12	0.8681 (4)	0.35926 (15)	0.7762 (2)	0.0544 (10)
C13	0.9170 (4)	0.36252 (15)	0.6943 (2)	0.0561 (10)
C14	0.6769 (4)	0.51741 (13)	0.92693 (19)	0.0447 (9)
C15	0.4810 (4)	0.54900 (15)	0.8754 (2)	0.0543 (10)
C16	0.5134 (4)	0.62267 (15)	0.8831 (2)	0.0551 (10)
C17	0.3782 (5)	0.68894 (17)	0.8475 (3)	0.0798 (13)
H1	0.81330	0.46250	0.41890	0.1010*
H2	1.05290	0.47510	0.26360	0.0800*
H2A	0.84130	0.43320	1.00030	0.0600*
H3	1.27820	0.38830	0.24980	0.0920*
H4	1.34340	0.27990	0.34300	0.0940*
H5	1.18960	0.26110	0.45380	0.0780*
H7	0.97800	0.30310	0.54140	0.0660*
H9	0.48080	0.42480	0.53520	0.0650*
H10	0.39510	0.41710	0.67330	0.0610*
H12	0.96640	0.34360	0.83730	0.0650*
H13	1.04890	0.34940	0.69990	0.0670*
H15	0.35650	0.52420	0.84310	0.0650*
H17A	0.39730	0.71040	0.79110	0.1200*
H17B	0.41320	0.72510	0.90030	0.1200*
H17C	0.23670	0.67420	0.82810	0.1200*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0458 (4)	0.0386 (4)	0.0611 (5)	−0.0045 (3)	0.0136 (3)	0.0006 (3)
O1	0.0703 (14)	0.0556 (12)	0.0757 (14)	0.0180 (10)	0.0273 (12)	0.0130 (10)
O2	0.0397 (11)	0.0645 (12)	0.0791 (14)	−0.0079 (9)	0.0186 (10)	−0.0030 (10)
O3	0.0735 (14)	0.0420 (10)	0.0787 (15)	0.0032 (10)	0.0233 (12)	0.0149 (10)
O4	0.0604 (13)	0.0418 (10)	0.0777 (14)	0.0020 (9)	0.0081 (11)	−0.0114 (10)
N1	0.0494 (14)	0.0503 (13)	0.0569 (15)	−0.0036 (11)	0.0112 (12)	−0.0023 (11)
N2	0.0453 (13)	0.0437 (12)	0.0482 (14)	0.0015 (10)	0.0040 (10)	0.0004 (10)
N3	0.0514 (15)	0.0416 (13)	0.0701 (17)	0.0036 (11)	0.0072 (12)	−0.0079 (11)
C1	0.0501 (17)	0.0427 (15)	0.0569 (18)	−0.0005 (13)	0.0115 (14)	−0.0037 (13)
C2	0.075 (2)	0.0521 (18)	0.072 (2)	−0.0019 (16)	0.0286 (18)	0.0057 (15)
C3	0.093 (3)	0.070 (2)	0.081 (2)	0.0014 (19)	0.048 (2)	−0.0028 (18)
C4	0.086 (3)	0.063 (2)	0.092 (3)	0.0162 (18)	0.040 (2)	−0.0062 (19)
C5	0.074 (2)	0.0438 (16)	0.066 (2)	0.0054 (15)	0.0150 (17)	−0.0016 (14)
C6	0.0493 (16)	0.0375 (14)	0.0508 (17)	−0.0035 (12)	0.0077 (13)	−0.0032 (12)
C7	0.0539 (18)	0.0430 (15)	0.0542 (18)	−0.0101 (13)	0.0062 (14)	−0.0002 (13)
C8	0.0494 (17)	0.0421 (14)	0.0530 (18)	−0.0076 (12)	0.0120 (14)	−0.0018 (13)
C9	0.0432 (17)	0.0520 (16)	0.0547 (18)	0.0016 (13)	0.0048 (14)	0.0039 (13)
C10	0.0371 (15)	0.0427 (15)	0.066 (2)	0.0016 (12)	0.0121 (14)	0.0005 (13)
C11	0.0417 (15)	0.0334 (13)	0.0529 (16)	−0.0021 (11)	0.0080 (13)	−0.0019 (12)
C12	0.0446 (17)	0.0538 (16)	0.0513 (18)	0.0040 (13)	0.0042 (14)	0.0002 (13)
C13	0.0401 (16)	0.0588 (18)	0.061 (2)	0.0018 (13)	0.0105 (14)	−0.0047 (14)
C14	0.0452 (16)	0.0420 (14)	0.0426 (16)	0.0005 (12)	0.0125 (13)	−0.0054 (12)
C15	0.0433 (16)	0.0483 (16)	0.0607 (19)	0.0027 (12)	0.0087 (14)	−0.0045 (13)
C16	0.0545 (18)	0.0513 (17)	0.0512 (17)	0.0068 (14)	0.0115 (14)	−0.0074 (13)
C17	0.078 (2)	0.0523 (18)	0.090 (3)	0.0170 (16)	0.012 (2)	−0.0013 (17)

Geometric parameters (Å, º) top

S1—O2	1.424 (2)	C8—C9	1.382 (4)
S1—O3	1.423 (2)	C9—C10	1.381 (4)
S1—N2	1.629 (2)	C10—C11	1.388 (4)
S1—C11	1.747 (3)	C11—C12	1.384 (4)
O1—C1	1.348 (3)	C12—C13	1.362 (4)
O4—N3	1.405 (3)	C14—C15	1.406 (4)
O4—C16	1.345 (4)	C15—C16	1.337 (4)
O1—H1	0.8200	C16—C17	1.483 (4)
N1—C7	1.286 (4)	C2—H2	0.9300
N1—C8	1.415 (4)	C3—H3	0.9300
N2—C14	1.390 (3)	C4—H4	0.9300
N3—C14	1.299 (4)	C5—H5	0.9300
N2—H2A	0.8600	C7—H7	0.9300
C1—C2	1.381 (4)	C9—H9	0.9300
C1—C6	1.400 (4)	C10—H10	0.9300
C2—C3	1.363 (5)	C12—H12	0.9300
C3—C4	1.379 (5)	C13—H13	0.9300
C4—C5	1.363 (5)	C15—H15	0.9300
C5—C6	1.388 (4)	C17—H17A	0.9600
C6—C7	1.442 (4)	C17—H17B	0.9600
C8—C13	1.395 (4)	C17—H17C	0.9600

S1···H15	3.1900	C2···H15ⁱⁱ	3.0700
O1···N1	2.606 (3)	C5···H12^ix	3.0000
O1···N1ⁱ	3.245 (3)	C7···H13	2.6700
O1···C10ⁱⁱ	3.313 (3)	C7···H1	2.4100
O2···C13ⁱⁱⁱ	3.276 (4)	C13···H7	2.6400
O2···C15	3.010 (3)	C13···H2ⁱ	2.9600
O3···C7^iv	3.172 (3)	C16···H3ⁱ	2.8500
O1···H10ⁱⁱ	2.5300	H1···N1	1.8800
O2···H10	2.5800	H1···C7	2.4100
O2···H15	2.5300	H2···C13ⁱ	2.9600
O2···H13ⁱⁱⁱ	2.6300	H2A···N3^vii	2.2400
O3···H12	2.6800	H3···O4ⁱ	2.7400
O3···H4^v	2.9000	H3···C16ⁱ	2.8500
O3···H7^iv	2.7800	H4···O3^x	2.9000
O4···H5^vi	2.6800	H5···H7	2.4200
O4···H3ⁱ	2.7400	H5···O4^xi	2.6800
N1···O1	2.606 (3)	H7···C13	2.6400
N1···O1ⁱ	3.245 (3)	H7···H5	2.4200
N2···N3^vii	2.898 (4)	H7···H13	2.3100
N3···N2^vii	2.898 (4)	H7···O3^ix	2.7800
N1···H1	1.8800	H10···O2	2.5800
N3···H2A^vii	2.2400	H10···O1ⁱⁱ	2.5300
C2···C8ⁱ	3.546 (4)	H12···O3	2.6800
C5···C9^viii	3.581 (4)	H12···C5^iv	3.0000
C7···O3^ix	3.172 (3)	H13···O2^viii	2.6300
C8···C2ⁱ	3.546 (4)	H13···C7	2.6700
C9···C5ⁱⁱⁱ	3.581 (4)	H13···H7	2.3100
C10···O1ⁱⁱ	3.313 (3)	H15···S1	3.1900
C13···O2^viii	3.276 (4)	H15···O2	2.5300
C15···O2	3.010 (3)	H15···C2ⁱⁱ	3.0700
C2···H17Cⁱⁱ	2.9800	H17C···C2ⁱⁱ	2.9800

O2—S1—O3	120.58 (13)	N3—C14—C15	111.9 (2)
O2—S1—N2	108.18 (12)	N2—C14—N3	117.9 (3)
O2—S1—C11	108.84 (13)	N2—C14—C15	130.2 (2)
O3—S1—N2	104.27 (12)	C14—C15—C16	104.7 (2)
O3—S1—C11	107.86 (13)	O4—C16—C15	109.8 (2)
N2—S1—C11	106.23 (12)	O4—C16—C17	116.1 (2)
N3—O4—C16	108.3 (2)	C15—C16—C17	134.1 (3)
C1—O1—H1	110.00	C1—C2—H2	120.00
C7—N1—C8	119.5 (2)	C3—C2—H2	120.00
S1—N2—C14	124.33 (18)	C2—C3—H3	120.00
O4—N3—C14	105.4 (2)	C4—C3—H3	120.00
S1—N2—H2A	118.00	C3—C4—H4	120.00
C14—N2—H2A	118.00	C5—C4—H4	120.00
C2—C1—C6	119.7 (3)	C4—C5—H5	119.00
O1—C1—C6	121.6 (3)	C6—C5—H5	119.00
O1—C1—C2	118.7 (2)	N1—C7—H7	119.00
C1—C2—C3	120.4 (3)	C6—C7—H7	119.00
C2—C3—C4	120.7 (4)	C8—C9—H9	120.00
C3—C4—C5	119.4 (4)	C10—C9—H9	120.00
C4—C5—C6	121.4 (3)	C9—C10—H10	120.00
C5—C6—C7	120.1 (2)	C11—C10—H10	120.00
C1—C6—C5	118.4 (3)	C11—C12—H12	120.00
C1—C6—C7	121.3 (2)	C13—C12—H12	120.00
N1—C7—C6	122.5 (2)	C8—C13—H13	120.00
N1—C8—C9	119.1 (2)	C12—C13—H13	120.00
N1—C8—C13	121.4 (3)	C14—C15—H15	128.00
C9—C8—C13	119.3 (3)	C16—C15—H15	128.00
C8—C9—C10	120.5 (3)	C16—C17—H17A	109.00
C9—C10—C11	119.4 (3)	C16—C17—H17B	109.00
S1—C11—C12	118.9 (2)	C16—C17—H17C	109.00
S1—C11—C10	121.1 (2)	H17A—C17—H17B	109.00
C10—C11—C12	120.0 (3)	H17A—C17—H17C	110.00
C11—C12—C13	120.3 (3)	H17B—C17—H17C	109.00
C8—C13—C12	120.4 (3)

O2—S1—N2—C14	−44.7 (3)	C2—C1—C6—C5	−0.8 (4)
O3—S1—N2—C14	−174.2 (2)	C2—C1—C6—C7	175.1 (3)
C11—S1—N2—C14	72.0 (3)	C1—C2—C3—C4	0.8 (5)
O2—S1—C11—C10	10.4 (2)	C2—C3—C4—C5	−1.1 (6)
O2—S1—C11—C12	−170.1 (2)	C3—C4—C5—C6	0.4 (5)
O3—S1—C11—C10	142.8 (2)	C4—C5—C6—C1	0.5 (5)
O3—S1—C11—C12	−37.7 (2)	C4—C5—C6—C7	−175.4 (3)
N2—S1—C11—C10	−105.9 (2)	C1—C6—C7—N1	2.4 (4)
N2—S1—C11—C12	73.6 (2)	C5—C6—C7—N1	178.2 (3)
C16—O4—N3—C14	−0.4 (3)	N1—C8—C9—C10	−177.1 (2)
N3—O4—C16—C15	−0.1 (3)	C13—C8—C9—C10	−2.7 (4)
N3—O4—C16—C17	−180.0 (3)	N1—C8—C13—C12	176.3 (2)
C8—N1—C7—C6	−170.2 (3)	C9—C8—C13—C12	2.1 (4)
C7—N1—C8—C9	−147.2 (3)	C8—C9—C10—C11	1.5 (4)
C7—N1—C8—C13	38.6 (4)	C9—C10—C11—S1	179.81 (19)
S1—N2—C14—N3	−152.9 (2)	C9—C10—C11—C12	0.3 (4)
S1—N2—C14—C15	29.5 (4)	S1—C11—C12—C13	179.6 (2)
O4—N3—C14—N2	−177.3 (2)	C10—C11—C12—C13	−0.9 (4)
O4—N3—C14—C15	0.7 (3)	C11—C12—C13—C8	−0.3 (4)
O1—C1—C2—C3	179.8 (3)	N2—C14—C15—C16	177.0 (3)
C6—C1—C2—C3	0.2 (5)	N3—C14—C15—C16	−0.7 (3)
O1—C1—C6—C5	179.6 (3)	C14—C15—C16—O4	0.4 (3)
O1—C1—C6—C7	−4.6 (4)	C14—C15—C16—C17	−179.7 (3)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z; (iv) x, −y+1/2, z+1/2; (v) x−1, −y+1/2, z+1/2; (vi) −x+2, y+1/2, −z+3/2; (vii) −x+2, −y+1, −z+2; (viii) x+1, y, z; (ix) x, −y+1/2, z−1/2; (x) x+1, −y+1/2, z−1/2; (xi) −x+2, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.606 (3)	147
N2—H2A···N3^vii	0.86	2.24	2.898 (4)	134
C10—H10···O1ⁱⁱ	0.93	2.53	3.313 (3)	141
C15—H15···O2	0.93	2.53	3.010 (3)	112

Symmetry codes: (ii) −x+1, −y+1, −z+1; (vii) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅N₃O₄S
M_r	357.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.0374 (1), 17.9244 (3), 14.5175 (3)
β (°)	112.962 (1)
V (Å³)	1686.15 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.25 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.947, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	14935, 2953, 2198
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.115, 1.06
No. of reflections	2953
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.30

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.606 (3)	147
N2—H2A···N3ⁱ	0.86	2.24	2.898 (4)	134
C10—H10···O1ⁱⁱ	0.93	2.53	3.313 (3)	141

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank the DST-India (FIST programme) for the use of diffractometer at the School of Chemistry, Bharathidasan University.

References

Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058–2077. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
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Kálmán, A., Czugler, M. & Argay, Gy. (1981). Acta Cryst. B37, 868–877. CSD CrossRef Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Subashini, A., Hemamalini, M., Muthiah, P. T., Bocelli, G. & Cantoni, A. (2009). J. Chem. Crystallogr. 39, 112–116. Web of Science CSD CrossRef CAS Google Scholar
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Volume 66| Part 10| October 2010| Page o2574

doi:10.1107/S1600536810036585

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

4-[(2-Hy­dr­oxy­benzyl­­idene)amino]-N-(5-methyl­isoxazol-3-yl)benzene­sulfonamide: a monoclinic polymorph

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-[(2-Hydroxybenzylidene)amino]-N-(5-methylisoxazol-3-yl)benzenesulfonamide: a monoclinic polymorph