4-[(2-Hy-droxy-benzyl-idene)amino]-N-(5-methyl-isoxazol-3-yl)benzene-sulfonamide: a monoclinic polymorph.

The title compound, C(17)H(15)N(3)O(4)S, is a monoclinic polymorph with space group P2(1)/c of the previously reported triclinic form in P [Subashini et al. (2009 ▶). J. Chem. Crystallogr.39, 112-116]. In both polymorphs, intra-molecular O-H⋯N hydrogen bonds and dimer formation via a pair of inter-molecular N-H⋯N hydrogen bonds with an R(2) (2)(8) motif are observed. The two polymorphs differ in the next level of supra-molecular 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 (8) ring motifs in sulfonamides, see: Adsmond & Grant (2001 ▶). For conformational studies on sulfonamides, see: Kálmán et al. (1981 ▶).

Experimental

Crystal data

C17H15N3O4S

M = 357.39

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.115

S = 1.06

2953 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.30 e Å−3

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.

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

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

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

C17H15N3O4S	F(000) = 744
Mr = 357.39	Dx = 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

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

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(Fo2) + (0.040P)2 + 0.9817P] where P = (Fo2 + 2Fc2)/3
2953 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.30 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 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.

	x	y	z	Uiso*/Ueq
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*

	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)

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···H12ix	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···C7iv	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···N3vii	2.2400
O3···H12	2.6800	H3···O4i	2.7400
O3···H4v	2.9000	H3···C16i	2.8500
O3···H7iv	2.7800	H4···O3x	2.9000
O4···H5vi	2.6800	H5···H7	2.4200
O4···H3i	2.7400	H5···O4xi	2.6800
N1···O1	2.606 (3)	H7···C13	2.6400
N1···O1i	3.245 (3)	H7···H5	2.4200
N2···N3vii	2.898 (4)	H7···H13	2.3100
N3···N2vii	2.898 (4)	H7···O3ix	2.7800
N1···H1	1.8800	H10···O2	2.5800
N3···H2Avii	2.2400	H10···O1ii	2.5300
C2···C8i	3.546 (4)	H12···O3	2.6800
C5···C9viii	3.581 (4)	H12···C5iv	3.0000
C7···O3ix	3.172 (3)	H13···O2viii	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···O2viii	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)

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···N3vii	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

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) ; (ii) .