4-(5-Chloro-2-hydroxy-benzyl-idene-amino)-N-(4,6-dimethyl-pyrimidin-2-yl)benzene-sulfonamide.

The title compound, C(19)H(17)ClN(4)O(3)S, is a Schiff base compound of 5-chloro-salicylaldehyde and sulfamethazine [4-amino-N-(4,6-dimethyl-2-pyrimidin-yl)benzene-sulfonamide]. The geometry around the S atom is distorted tetra-hedral, comprising two O atoms of the sulfonyl group, a C atom of a benzene ring and the amino N atom. The title compound has an intra-molecular O-H⋯N hydrogen bond and two inter-molecular C-H⋯O and N-H⋯O hydrogen bonds, which link neighbouring mol-ecules into 10-membered rings. As a result of an unavoidable conformational arrangement, a slightly short intra-molecular contact of distance 2.59 Å exists between an O atom of the sulfonyl group and an H atom of the sulfamethazine benzene ring.

Related literature

For related literature, see: Basak et al. (1983 ▶); Chohan & Shad (2007 ▶); Yang (2006 ▶); Shad et al. (2008 ▶); Zareef et al. (2007 ▶).

Experimental

Crystal data

C19H17ClN4O3S

M = 416.88

Orthorhombic,

a = 11.7332 (7) Å

b = 13.8506 (6) Å

c = 23.6635 (14) Å

V = 3845.6 (4) Å3

Z = 8

Mo Kα radiation radiation

μ = 0.34 mm−1

T = 296 (2) K

0.22 × 0.18 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.940, T max = 0.958

21114 measured reflections

4787 independent reflections

2797 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.148

S = 1.05

2797 reflections

259 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.28 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/S1600536808005606/fj2100sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005606/fj2100Isup2.hkl

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

C19H17ClN4O3S	Dx = 1.440 Mg m−3
Mr = 416.88	Melting point: 497 K
Orthorhombic, Pbca	Mo Kα radiation radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2797 reflections
a = 11.7332 (7) Å	θ = 1.7–28.3º
b = 13.8506 (6) Å	µ = 0.34 mm−1
c = 23.6635 (14) Å	T = 296 (2) K
V = 3845.6 (4) Å3	Prismatic, red
Z = 8	0.22 × 0.18 × 0.14 mm
F000 = 1728

Bruker Kappa APEXII CCD diffractometer	4787 independent reflections
Radiation source: fine-focus sealed tube	2797 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.043
Detector resolution: 7.40 pixels mm-1	θmax = 28.3º
T = 296(2) K	θmin = 1.7º
ω scans	h = −15→15
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −17→18
Tmin = 0.940, Tmax = 0.958	l = −31→30
21114 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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.148	w = 1/[σ2(Fo2) + (0.0488P)2 + 2.8076P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2797 reflections	Δρmax = 0.32 e Å−3
259 parameters	Δρmin = −0.28 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	1.17644 (10)	−0.26287 (7)	−0.12764 (5)	0.0872 (3)
S1	0.40720 (6)	0.12989 (5)	0.10363 (3)	0.04261 (19)
O1	0.9575 (2)	0.11270 (16)	−0.10024 (12)	0.0767 (8)
H1	0.902 (4)	0.105 (3)	−0.0865 (19)	0.092*
O2	0.34086 (18)	0.19106 (14)	0.06787 (9)	0.0566 (6)
O3	0.35672 (17)	0.04443 (14)	0.12555 (9)	0.0533 (5)
N1	0.82013 (19)	0.03779 (16)	−0.03019 (10)	0.0449 (6)
N2	0.4449 (2)	0.20143 (17)	0.15497 (11)	0.0484 (6)
H2	0.442 (3)	0.252 (2)	0.1502 (14)	0.058*
N3	0.5377 (2)	0.25140 (17)	0.23450 (10)	0.0504 (6)
N4	0.5464 (2)	0.08644 (17)	0.20508 (10)	0.0494 (6)
C1	0.9660 (2)	−0.05366 (19)	−0.07463 (12)	0.0438 (6)
C2	1.0209 (3)	−0.1429 (2)	−0.08168 (13)	0.0535 (8)
H2A	0.9970	−0.1960	−0.0608	0.064*
C3	1.1091 (3)	−0.1523 (2)	−0.11879 (14)	0.0546 (8)
C4	1.1463 (3)	−0.0739 (2)	−0.14968 (16)	0.0685 (10)
H4A	1.2067	−0.0811	−0.1748	0.082*
C5	1.0950 (3)	0.0147 (2)	−0.14375 (16)	0.0703 (10)
H5	1.1202	0.0668	−0.1651	0.084*
C6	1.0057 (3)	0.0265 (2)	−0.10596 (14)	0.0543 (8)
C7	0.8701 (2)	−0.0437 (2)	−0.03688 (12)	0.0479 (7)
H7	0.8442	−0.0973	−0.0171	0.058*
C8	0.7233 (2)	0.05312 (19)	0.00426 (11)	0.0412 (6)
C9	0.6811 (3)	0.1460 (2)	0.00458 (14)	0.0565 (8)
H9	0.7170	0.1935	−0.0168	0.068*
C10	0.5868 (3)	0.1695 (2)	0.03601 (14)	0.0561 (8)
H10	0.5597	0.2325	0.0364	0.067*
C11	0.5325 (2)	0.09899 (18)	0.06706 (11)	0.0390 (6)
C12	0.5748 (2)	0.00607 (19)	0.06810 (12)	0.0448 (7)
H12	0.5395	−0.0409	0.0901	0.054*
C13	0.6696 (2)	−0.01695 (19)	0.03636 (12)	0.0479 (7)
H13	0.6976	−0.0798	0.0365	0.057*
C14	0.5142 (2)	0.1773 (2)	0.20062 (11)	0.0432 (6)
C15	0.6017 (3)	0.2304 (2)	0.27940 (13)	0.0577 (8)
C16	0.6394 (3)	0.1374 (3)	0.28828 (14)	0.0631 (9)
H16	0.6841	0.1229	0.3196	0.076*
C17	0.6107 (3)	0.0666 (2)	0.25061 (14)	0.0552 (8)
C18	0.6497 (3)	−0.0362 (3)	0.25674 (17)	0.0825 (12)
H18A	0.6198	−0.0741	0.2262	0.124*
H18B	0.6227	−0.0618	0.2920	0.124*
H18C	0.7314	−0.0385	0.2560	0.124*
C19	0.6268 (4)	0.3114 (3)	0.31925 (16)	0.0894 (13)
H19A	0.5930	0.3698	0.3053	0.134*
H19B	0.7078	0.3198	0.3223	0.134*
H19C	0.5958	0.2966	0.3558	0.134*

	U11	U22	U33	U12	U13	U23
Cl1	0.0896 (8)	0.0611 (5)	0.1110 (9)	0.0210 (5)	0.0139 (6)	−0.0059 (5)
S1	0.0421 (4)	0.0436 (4)	0.0421 (4)	0.0046 (3)	−0.0031 (3)	0.0001 (3)
O1	0.0854 (19)	0.0453 (12)	0.099 (2)	0.0069 (12)	0.0452 (16)	0.0174 (12)
O2	0.0549 (13)	0.0587 (12)	0.0562 (13)	0.0154 (10)	−0.0166 (10)	0.0013 (10)
O3	0.0474 (12)	0.0526 (11)	0.0601 (13)	−0.0030 (9)	0.0087 (10)	0.0007 (10)
N1	0.0447 (13)	0.0476 (13)	0.0424 (14)	−0.0036 (11)	0.0031 (11)	−0.0003 (10)
N2	0.0594 (16)	0.0417 (12)	0.0442 (14)	0.0095 (12)	−0.0076 (12)	−0.0026 (11)
N3	0.0539 (15)	0.0534 (14)	0.0440 (14)	−0.0051 (12)	−0.0003 (12)	−0.0005 (11)
N4	0.0525 (15)	0.0515 (14)	0.0442 (14)	0.0134 (11)	−0.0001 (11)	0.0037 (11)
C1	0.0435 (16)	0.0447 (14)	0.0433 (16)	−0.0046 (12)	−0.0021 (13)	−0.0001 (12)
C2	0.060 (2)	0.0440 (15)	0.0562 (19)	−0.0030 (14)	0.0014 (15)	0.0036 (14)
C3	0.0499 (18)	0.0502 (16)	0.064 (2)	0.0036 (14)	0.0001 (15)	−0.0047 (14)
C4	0.056 (2)	0.068 (2)	0.081 (3)	0.0001 (17)	0.0257 (18)	−0.0003 (19)
C5	0.068 (2)	0.0556 (19)	0.087 (3)	−0.0026 (17)	0.030 (2)	0.0141 (18)
C6	0.0564 (19)	0.0460 (16)	0.060 (2)	−0.0028 (14)	0.0102 (16)	0.0026 (14)
C7	0.0500 (17)	0.0491 (15)	0.0447 (16)	−0.0117 (13)	−0.0008 (14)	0.0043 (13)
C8	0.0442 (15)	0.0434 (14)	0.0360 (14)	−0.0049 (12)	0.0003 (12)	−0.0006 (12)
C9	0.063 (2)	0.0436 (16)	0.063 (2)	−0.0043 (14)	0.0172 (16)	0.0136 (14)
C10	0.065 (2)	0.0387 (14)	0.064 (2)	0.0033 (14)	0.0120 (17)	0.0105 (14)
C11	0.0428 (15)	0.0409 (13)	0.0334 (14)	−0.0002 (11)	−0.0030 (11)	0.0017 (11)
C12	0.0522 (17)	0.0375 (14)	0.0446 (16)	−0.0021 (12)	0.0090 (13)	0.0071 (12)
C13	0.0533 (18)	0.0386 (14)	0.0517 (18)	0.0031 (12)	0.0073 (14)	0.0044 (13)
C14	0.0405 (15)	0.0512 (16)	0.0378 (15)	0.0043 (13)	0.0040 (12)	0.0023 (12)
C15	0.0516 (19)	0.076 (2)	0.0454 (18)	−0.0206 (16)	−0.0016 (15)	0.0042 (16)
C16	0.0472 (18)	0.093 (2)	0.0489 (19)	−0.0113 (17)	−0.0124 (15)	0.0199 (18)
C17	0.0459 (17)	0.0693 (19)	0.0504 (18)	0.0065 (15)	0.0032 (14)	0.0173 (16)
C18	0.081 (3)	0.081 (2)	0.086 (3)	0.026 (2)	−0.007 (2)	0.027 (2)
C19	0.105 (3)	0.096 (3)	0.068 (2)	−0.046 (3)	−0.019 (2)	−0.004 (2)

Cl1—C3	1.736 (3)	C5—H5	0.9300
S1—O3	1.422 (2)	C7—H7	0.9300
S1—O2	1.4282 (19)	C8—C9	1.379 (4)
S1—N2	1.629 (3)	C8—C13	1.384 (4)
S1—C11	1.759 (3)	C9—C10	1.371 (4)
O1—C6	1.328 (4)	C9—H9	0.9300
O1—H1	0.74 (4)	C10—C11	1.378 (4)
N1—C7	1.282 (4)	C10—H10	0.9300
N1—C8	1.414 (3)	C11—C12	1.379 (3)
N2—C14	1.393 (4)	C12—C13	1.380 (4)
N2—H2	0.71 (3)	C12—H12	0.9300
N3—C14	1.332 (3)	C13—H13	0.9300
N3—C15	1.333 (4)	C15—C16	1.378 (5)
N4—C14	1.318 (3)	C15—C19	1.495 (5)
N4—C17	1.343 (4)	C16—C17	1.368 (5)
C1—C2	1.404 (4)	C16—H16	0.9300
C1—C6	1.414 (4)	C17—C18	1.503 (4)
C1—C7	1.443 (4)	C18—H18A	0.9600
C2—C3	1.363 (4)	C18—H18B	0.9600
C2—H2A	0.9300	C18—H18C	0.9600
C3—C4	1.380 (4)	C19—H19A	0.9600
C4—C5	1.373 (4)	C19—H19B	0.9600
C4—H4A	0.9300	C19—H19C	0.9600
C5—C6	1.388 (4)
O3—S1—O2	118.89 (13)	C10—C9—H9	119.6
O3—S1—N2	110.33 (13)	C8—C9—H9	119.6
O2—S1—N2	103.22 (12)	C9—C10—C11	119.6 (3)
O3—S1—C11	108.98 (12)	C9—C10—H10	120.2
O2—S1—C11	107.97 (13)	C11—C10—H10	120.2
N2—S1—C11	106.75 (13)	C10—C11—C12	120.3 (3)
C6—O1—H1	107 (3)	C10—C11—S1	118.5 (2)
C7—N1—C8	124.8 (2)	C12—C11—S1	121.3 (2)
C14—N2—S1	126.2 (2)	C11—C12—C13	119.7 (2)
C14—N2—H2	113 (3)	C11—C12—H12	120.1
S1—N2—H2	118 (3)	C13—C12—H12	120.1
C14—N3—C15	115.3 (3)	C12—C13—C8	120.2 (3)
C14—N4—C17	114.9 (3)	C12—C13—H13	119.9
C2—C1—C6	118.5 (3)	C8—C13—H13	119.9
C2—C1—C7	121.1 (3)	N4—C14—N3	128.9 (3)
C6—C1—C7	120.4 (3)	N4—C14—N2	117.3 (3)
C3—C2—C1	120.6 (3)	N3—C14—N2	113.8 (2)
C3—C2—H2A	119.7	N3—C15—C16	120.5 (3)
C1—C2—H2A	119.7	N3—C15—C19	116.7 (3)
C2—C3—C4	120.4 (3)	C16—C15—C19	122.8 (3)
C2—C3—Cl1	120.5 (2)	C17—C16—C15	119.4 (3)
C4—C3—Cl1	119.1 (3)	C17—C16—H16	120.3
C5—C4—C3	120.7 (3)	C15—C16—H16	120.3
C5—C4—H4A	119.7	N4—C17—C16	120.9 (3)
C3—C4—H4A	119.7	N4—C17—C18	116.3 (3)
C4—C5—C6	120.1 (3)	C16—C17—C18	122.8 (3)
C4—C5—H5	119.9	C17—C18—H18A	109.5
C6—C5—H5	119.9	C17—C18—H18B	109.5
O1—C6—C5	119.5 (3)	H18A—C18—H18B	109.5
O1—C6—C1	120.8 (3)	C17—C18—H18C	109.5
C5—C6—C1	119.6 (3)	H18A—C18—H18C	109.5
N1—C7—C1	121.2 (3)	H18B—C18—H18C	109.5
N1—C7—H7	119.4	C15—C19—H19A	109.5
C1—C7—H7	119.4	C15—C19—H19B	109.5
C9—C8—C13	119.2 (3)	H19A—C19—H19B	109.5
C9—C8—N1	115.6 (2)	C15—C19—H19C	109.5
C13—C8—N1	125.2 (2)	H19A—C19—H19C	109.5
C10—C9—C8	120.9 (3)	H19B—C19—H19C	109.5
O3—S1—N2—C14	54.0 (3)	O3—S1—C11—C10	171.4 (2)
O2—S1—N2—C14	−178.0 (3)	O2—S1—C11—C10	41.0 (3)
C11—S1—N2—C14	−64.3 (3)	N2—S1—C11—C10	−69.4 (3)
C6—C1—C2—C3	−1.3 (4)	O3—S1—C11—C12	−7.1 (3)
C7—C1—C2—C3	177.9 (3)	O2—S1—C11—C12	−137.5 (2)
C1—C2—C3—C4	0.6 (5)	N2—S1—C11—C12	112.0 (2)
C1—C2—C3—Cl1	−179.7 (2)	C10—C11—C12—C13	−2.2 (4)
C2—C3—C4—C5	−0.3 (6)	S1—C11—C12—C13	176.3 (2)
Cl1—C3—C4—C5	−180.0 (3)	C11—C12—C13—C8	1.0 (4)
C3—C4—C5—C6	0.7 (6)	C9—C8—C13—C12	0.2 (4)
C4—C5—C6—O1	179.4 (4)	N1—C8—C13—C12	−179.4 (3)
C4—C5—C6—C1	−1.5 (6)	C17—N4—C14—N3	0.9 (4)
C2—C1—C6—O1	−179.1 (3)	C17—N4—C14—N2	−178.4 (3)
C7—C1—C6—O1	1.7 (5)	C15—N3—C14—N4	−0.9 (4)
C2—C1—C6—C5	1.8 (5)	C15—N3—C14—N2	178.4 (3)
C7—C1—C6—C5	−177.4 (3)	S1—N2—C14—N4	−4.9 (4)
C8—N1—C7—C1	177.5 (2)	S1—N2—C14—N3	175.7 (2)
C2—C1—C7—N1	179.7 (3)	C14—N3—C15—C16	0.4 (4)
C6—C1—C7—N1	−1.1 (4)	C14—N3—C15—C19	−178.2 (3)
C7—N1—C8—C9	−178.6 (3)	N3—C15—C16—C17	−0.1 (5)
C7—N1—C8—C13	1.1 (4)	C19—C15—C16—C17	178.4 (3)
C13—C8—C9—C10	−0.2 (5)	C14—N4—C17—C16	−0.5 (4)
N1—C8—C9—C10	179.4 (3)	C14—N4—C17—C18	−179.5 (3)
C8—C9—C10—C11	−0.9 (5)	C15—C16—C17—N4	0.2 (5)
C9—C10—C11—C12	2.2 (5)	C15—C16—C17—C18	179.1 (3)
C9—C10—C11—S1	−176.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.73 (5)	1.90 (4)	2.534 (3)	146 (5)
N2—H2···O1i	0.71 (3)	2.22 (3)	2.886 (3)	156 (3)
C9—H9···O2ii	0.93	2.48	3.398 (4)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.73 (5)	1.90 (4)	2.534 (3)	146 (5)
N2—H2⋯O1i	0.71 (3)	2.22 (3)	2.886 (3)	156 (3)
C9—H9⋯O2ii	0.93	2.48	3.398 (4)	171

Symmetry codes: (i) ; (ii) .