2-[(E)-({4-[(4,6-Dimethyl-pyrimidin-2-yl)sulfamo-yl]phen-yl}iminio)meth-yl]-6-hy-droxy-phenolate.

The title compound, C(19)H(18)N(4)O(4)S, exists as a zwitterion in the solid state, with nominal proton transfer from a phenol group to the imine N atom. The 2,3-dihy-droxy-benzaldehyde fragment is oriented at a dihedral angle of 35.51 (11)° to the adajacent aniline group and makes a dihedral angle of 76.99 (6)° with the 4,6-dimethyl-pyrimidin-2-amine group. Intra-molecular O-H⋯O and N-H⋯O hydrogen bonds close S(5) and S(6) rings, respectively; the same O atom accepts both bonds. In the crystal, polymeric chains along [001] are formed from mol-ecules joined end-to-end by N-H⋯O and O-H⋯N hydrogen bonds; these feature R(2) (3)(6) loops. The polymeric chains are linked by C-H⋯O inter-actions and there are π-π inter-actions between the pyrimidine rings with a centroid-centroid distance of 3.446 (2) Å.

Related literature

For related structures, see: Chohan et al. (2008 ▶); Shad et al. (2009 ▶); Tahir et al. (2012 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H18N4O4S

M = 398.43

Orthorhombic,

a = 24.7506 (12) Å

b = 12.1689 (6) Å

c = 12.8408 (5) Å

V = 3867.5 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.20 mm−1

T = 296 K

0.34 × 0.28 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.935, T max = 0.971

16627 measured reflections

3796 independent reflections

1778 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.151

S = 1.01

3796 reflections

259 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034757/hb6908sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034757/hb6908Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034757/hb6908Isup3.cml

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

C19H18N4O4S	F(000) = 1664
Mr = 398.43	Dx = 1.369 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 1778 reflections
a = 24.7506 (12) Å	θ = 1.7–26.0°
b = 12.1689 (6) Å	µ = 0.20 mm−1
c = 12.8408 (5) Å	T = 296 K
V = 3867.5 (3) Å3	Plate, dark red
Z = 8	0.34 × 0.28 × 0.15 mm

Bruker Kappa APEXII CCD diffractometer	3796 independent reflections
Radiation source: fine-focus sealed tube	1778 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 8.00 pixels mm-1	θmax = 26.0°, θmin = 1.7°
ω scans	h = −30→29
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
Tmin = 0.935, Tmax = 0.971	l = −15→14
16627 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0534P)2 + 1.0105P] where P = (Fo2 + 2Fc2)/3
3796 reflections	(Δ/σ)max < 0.001
259 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.28 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 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
S1	0.33210 (4)	0.16234 (8)	0.39452 (7)	0.0639 (3)
O1	0.14274 (12)	0.0303 (2)	−0.1123 (2)	0.0874 (11)
O2	0.07789 (15)	−0.0466 (3)	−0.2721 (3)	0.1110 (16)
O3	0.30024 (11)	0.2317 (2)	0.46012 (18)	0.0765 (10)
O4	0.36264 (12)	0.0762 (2)	0.43976 (18)	0.0799 (10)
N1	0.19699 (14)	−0.0123 (3)	0.0534 (3)	0.0683 (14)
N2	0.37120 (13)	0.2493 (3)	0.3342 (2)	0.0719 (11)
N3	0.42863 (12)	0.3128 (3)	0.2071 (2)	0.0638 (11)
N4	0.41470 (12)	0.1191 (3)	0.2320 (2)	0.0650 (12)
C1	0.15104 (16)	−0.1524 (3)	−0.0429 (3)	0.0673 (17)
C2	0.13077 (16)	−0.0756 (3)	−0.1170 (3)	0.0683 (16)
C3	0.09721 (18)	−0.1143 (3)	−0.1978 (3)	0.0783 (17)
C4	0.08434 (18)	−0.2239 (4)	−0.2017 (4)	0.091 (2)
C5	0.10447 (18)	−0.2985 (3)	−0.1295 (4)	0.0843 (19)
C6	0.13772 (17)	−0.2643 (3)	−0.0517 (3)	0.0773 (17)
C7	0.18412 (16)	−0.1152 (3)	0.0396 (3)	0.0700 (17)
C8	0.22986 (15)	0.0266 (3)	0.1351 (3)	0.0567 (14)
C9	0.27177 (16)	−0.0346 (3)	0.1735 (3)	0.0667 (16)
C10	0.30228 (15)	0.0054 (3)	0.2545 (3)	0.0653 (14)
C11	0.29108 (14)	0.1070 (3)	0.2961 (2)	0.0523 (12)
C12	0.24920 (16)	0.1698 (3)	0.2564 (3)	0.0633 (14)
C13	0.21849 (16)	0.1290 (3)	0.1757 (3)	0.0653 (14)
C14	0.40682 (15)	0.2243 (3)	0.2534 (3)	0.0613 (16)
C15	0.46458 (16)	0.2897 (3)	0.1314 (3)	0.0663 (16)
C16	0.47691 (16)	0.1837 (3)	0.1050 (3)	0.0730 (16)
C17	0.45058 (16)	0.0989 (3)	0.1559 (3)	0.0683 (16)
C18	0.45913 (17)	−0.0204 (3)	0.1284 (3)	0.0923 (19)
C19	0.48948 (18)	0.3859 (3)	0.0768 (3)	0.0920 (19)
H1	0.1840 (16)	0.024 (3)	0.010 (3)	0.0821*
H2	0.08717	0.01670	−0.25928	0.1666*
H2A	0.36975	0.31672	0.35398	0.0861*
H4	0.06153	−0.24894	−0.25413	0.1089*
H5	0.09512	−0.37230	−0.13437	0.1011*
H6	0.15163	−0.31479	−0.00446	0.0928*
H7	0.19743	−0.16678	0.08640	0.0841*
H9	0.27959	−0.10292	0.14484	0.0801*
H10	0.33052	−0.03633	0.28130	0.0782*
H12	0.24188	0.23889	0.28391	0.0759*
H13	0.19016	0.17036	0.14875	0.0779*
H16	0.50251	0.16893	0.05389	0.0876*
H18A	0.43576	−0.04011	0.07173	0.1383*
H18B	0.45100	−0.06537	0.18778	0.1383*
H18C	0.49606	−0.03159	0.10819	0.1383*
H19A	0.46303	0.42001	0.03270	0.1379*
H19B	0.51940	0.36133	0.03535	0.1379*
H19C	0.50198	0.43815	0.12743	0.1379*

	U11	U22	U33	U12	U13	U23
S1	0.0759 (7)	0.0645 (6)	0.0512 (5)	−0.0047 (6)	0.0066 (5)	−0.0030 (5)
O1	0.112 (2)	0.0531 (16)	0.097 (2)	0.0023 (16)	−0.0265 (17)	−0.0057 (15)
O2	0.141 (3)	0.080 (2)	0.112 (3)	0.012 (2)	−0.051 (2)	−0.016 (2)
O3	0.090 (2)	0.0805 (18)	0.0591 (15)	−0.0076 (15)	0.0199 (14)	−0.0167 (14)
O4	0.099 (2)	0.0790 (18)	0.0618 (16)	0.0104 (16)	−0.0146 (15)	0.0079 (14)
N1	0.083 (3)	0.060 (2)	0.062 (2)	0.0034 (19)	−0.0070 (19)	0.0035 (18)
N2	0.081 (2)	0.0598 (18)	0.075 (2)	−0.0124 (17)	0.0241 (19)	−0.0180 (17)
N3	0.066 (2)	0.068 (2)	0.0573 (19)	−0.0040 (17)	−0.0016 (16)	0.0028 (16)
N4	0.065 (2)	0.068 (2)	0.062 (2)	−0.0039 (17)	0.0091 (17)	−0.0125 (17)
C1	0.066 (3)	0.062 (3)	0.074 (3)	−0.001 (2)	0.005 (2)	−0.007 (2)
C2	0.071 (3)	0.057 (2)	0.077 (3)	−0.002 (2)	−0.001 (2)	−0.019 (2)
C3	0.079 (3)	0.070 (3)	0.086 (3)	0.003 (2)	−0.010 (3)	−0.015 (3)
C4	0.090 (4)	0.073 (3)	0.109 (4)	−0.009 (3)	−0.010 (3)	−0.029 (3)
C5	0.084 (3)	0.059 (3)	0.110 (4)	−0.011 (2)	0.009 (3)	−0.017 (3)
C6	0.080 (3)	0.059 (3)	0.093 (3)	−0.006 (2)	0.016 (3)	0.000 (2)
C7	0.071 (3)	0.062 (3)	0.077 (3)	0.003 (2)	0.009 (2)	0.005 (2)
C8	0.068 (3)	0.051 (2)	0.051 (2)	−0.003 (2)	−0.0007 (19)	0.0017 (19)
C9	0.076 (3)	0.051 (2)	0.073 (3)	0.009 (2)	−0.002 (2)	−0.004 (2)
C10	0.072 (3)	0.055 (2)	0.069 (2)	0.008 (2)	−0.007 (2)	−0.002 (2)
C11	0.061 (2)	0.047 (2)	0.049 (2)	−0.0016 (18)	0.0038 (17)	0.0042 (17)
C12	0.086 (3)	0.048 (2)	0.056 (2)	0.006 (2)	0.013 (2)	−0.002 (2)
C13	0.076 (3)	0.060 (2)	0.060 (2)	0.015 (2)	−0.001 (2)	0.005 (2)
C14	0.061 (3)	0.066 (3)	0.057 (2)	−0.008 (2)	0.002 (2)	−0.008 (2)
C15	0.061 (3)	0.087 (3)	0.051 (2)	−0.006 (2)	−0.004 (2)	0.006 (2)
C16	0.071 (3)	0.091 (3)	0.057 (2)	0.001 (2)	0.009 (2)	−0.004 (2)
C17	0.068 (3)	0.081 (3)	0.056 (2)	0.002 (2)	−0.002 (2)	−0.004 (2)
C18	0.106 (4)	0.088 (3)	0.083 (3)	0.011 (3)	0.017 (3)	−0.018 (3)
C19	0.095 (4)	0.104 (3)	0.077 (3)	−0.013 (3)	0.018 (2)	0.023 (3)

S1—O3	1.430 (3)	C8—C13	1.380 (5)
S1—O4	1.417 (3)	C9—C10	1.374 (5)
S1—N2	1.630 (3)	C10—C11	1.375 (5)
S1—C11	1.755 (3)	C11—C12	1.385 (5)
O1—C2	1.324 (4)	C12—C13	1.378 (5)
O2—C3	1.348 (5)	C15—C16	1.368 (5)
O2—H2	0.8200	C15—C19	1.497 (5)
N1—C7	1.304 (5)	C16—C17	1.385 (5)
N1—C8	1.409 (5)	C17—C18	1.509 (5)
N2—C14	1.395 (5)	C4—H4	0.9300
N3—C15	1.347 (5)	C5—H5	0.9300
N3—C14	1.343 (5)	C6—H6	0.9300
N4—C14	1.324 (5)	C7—H7	0.9300
N4—C17	1.343 (5)	C9—H9	0.9300
N1—H1	0.78 (4)	C10—H10	0.9300
N2—H2A	0.8600	C12—H12	0.9300
C1—C2	1.425 (5)	C13—H13	0.9300
C1—C6	1.406 (5)	C16—H16	0.9300
C1—C7	1.413 (5)	C18—H18A	0.9600
C2—C3	1.410 (6)	C18—H18B	0.9600
C3—C4	1.372 (6)	C18—H18C	0.9600
C4—C5	1.390 (7)	C19—H19A	0.9600
C5—C6	1.360 (6)	C19—H19B	0.9600
C8—C9	1.369 (5)	C19—H19C	0.9600
O3—S1—O4	119.31 (15)	N3—C14—N4	128.6 (3)
O3—S1—N2	102.96 (16)	N2—C14—N3	114.1 (3)
O3—S1—C11	109.37 (16)	N3—C15—C19	116.5 (3)
O4—S1—N2	111.00 (17)	C16—C15—C19	122.0 (4)
O4—S1—C11	108.66 (17)	N3—C15—C16	121.5 (4)
N2—S1—C11	104.50 (15)	C15—C16—C17	118.7 (4)
C3—O2—H2	109.00	N4—C17—C18	116.0 (3)
C7—N1—C8	124.4 (4)	C16—C17—C18	122.7 (3)
S1—N2—C14	126.0 (3)	N4—C17—C16	121.2 (3)
C14—N3—C15	114.7 (3)	C3—C4—H4	119.00
C14—N4—C17	115.2 (3)	C5—C4—H4	119.00
C7—N1—H1	110 (3)	C4—C5—H5	120.00
C8—N1—H1	125 (3)	C6—C5—H5	120.00
C14—N2—H2A	117.00	C1—C6—H6	120.00
S1—N2—H2A	117.00	C5—C6—H6	120.00
C2—C1—C7	119.6 (3)	N1—C7—H7	118.00
C2—C1—C6	119.9 (4)	C1—C7—H7	118.00
C6—C1—C7	120.4 (3)	C8—C9—H9	120.00
C1—C2—C3	118.7 (3)	C10—C9—H9	120.00
O1—C2—C1	122.0 (3)	C9—C10—H10	120.00
O1—C2—C3	119.4 (3)	C11—C10—H10	120.00
C2—C3—C4	119.2 (4)	C11—C12—H12	120.00
O2—C3—C2	121.7 (3)	C13—C12—H12	120.00
O2—C3—C4	119.1 (4)	C8—C13—H13	120.00
C3—C4—C5	121.8 (4)	C12—C13—H13	120.00
C4—C5—C6	120.5 (4)	C15—C16—H16	121.00
C1—C6—C5	119.8 (4)	C17—C16—H16	121.00
N1—C7—C1	123.4 (4)	C17—C18—H18A	109.00
N1—C8—C9	121.5 (3)	C17—C18—H18B	109.00
C9—C8—C13	120.7 (4)	C17—C18—H18C	109.00
N1—C8—C13	117.8 (3)	H18A—C18—H18B	109.00
C8—C9—C10	119.8 (3)	H18A—C18—H18C	109.00
C9—C10—C11	120.1 (3)	H18B—C18—H18C	109.00
S1—C11—C10	120.5 (3)	C15—C19—H19A	109.00
S1—C11—C12	119.1 (3)	C15—C19—H19B	109.00
C10—C11—C12	120.3 (3)	C15—C19—H19C	109.00
C11—C12—C13	119.4 (3)	H19A—C19—H19B	109.00
C8—C13—C12	119.8 (4)	H19A—C19—H19C	109.00
N2—C14—N4	117.3 (3)	H19B—C19—H19C	109.00
O3—S1—N2—C14	−173.5 (3)	C2—C1—C6—C5	−1.6 (6)
O4—S1—N2—C14	57.7 (3)	C7—C1—C6—C5	177.9 (4)
C11—S1—N2—C14	−59.3 (3)	C2—C1—C7—N1	1.0 (6)
O3—S1—C11—C10	−149.8 (3)	C6—C1—C7—N1	−178.5 (4)
O3—S1—C11—C12	34.1 (3)	O1—C2—C3—O2	1.6 (6)
O4—S1—C11—C10	−18.0 (3)	O1—C2—C3—C4	−179.2 (4)
O4—S1—C11—C12	165.9 (3)	C1—C2—C3—O2	−178.1 (4)
N2—S1—C11—C10	100.5 (3)	C1—C2—C3—C4	1.1 (6)
N2—S1—C11—C12	−75.6 (3)	O2—C3—C4—C5	177.8 (4)
C8—N1—C7—C1	180.0 (4)	C2—C3—C4—C5	−1.5 (7)
C7—N1—C8—C9	34.0 (6)	C3—C4—C5—C6	0.3 (7)
C7—N1—C8—C13	−146.0 (4)	C4—C5—C6—C1	1.2 (7)
S1—N2—C14—N3	170.9 (3)	N1—C8—C9—C10	−178.8 (4)
S1—N2—C14—N4	−8.9 (5)	C13—C8—C9—C10	1.1 (6)
C15—N3—C14—N2	177.7 (3)	N1—C8—C13—C12	179.3 (4)
C15—N3—C14—N4	−2.5 (6)	C9—C8—C13—C12	−0.7 (6)
C14—N3—C15—C16	0.3 (5)	C8—C9—C10—C11	−0.7 (6)
C14—N3—C15—C19	179.4 (3)	C9—C10—C11—S1	−176.4 (3)
C17—N4—C14—N2	−178.0 (3)	C9—C10—C11—C12	−0.3 (5)
C17—N4—C14—N3	2.2 (6)	S1—C11—C12—C13	176.9 (3)
C14—N4—C17—C16	0.1 (5)	C10—C11—C12—C13	0.8 (5)
C14—N4—C17—C18	−178.5 (3)	C11—C12—C13—C8	−0.3 (6)
C6—C1—C2—O1	−179.3 (4)	N3—C15—C16—C17	1.7 (6)
C6—C1—C2—C3	0.4 (6)	C19—C15—C16—C17	−177.3 (4)
C7—C1—C2—O1	1.2 (6)	C15—C16—C17—N4	−1.9 (6)
C7—C1—C2—C3	−179.1 (4)	C15—C16—C17—C18	176.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.78 (4)	1.88 (4)	2.569 (5)	148 (4)
O2—H2···O1	0.82	2.34	2.768 (5)	113
O2—H2···N3i	0.82	2.16	2.862 (5)	144
N2—H2A···O1ii	0.86	1.94	2.790 (4)	172
C18—H18A···O4iii	0.96	2.52	3.469 (5)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.78 (4)	1.88 (4)	2.569 (5)	148 (4)
O2—H2⋯O1	0.82	2.34	2.768 (5)	113
O2—H2⋯N3i	0.82	2.16	2.862 (5)	144
N2—H2A⋯O1ii	0.86	1.94	2.790 (4)	172
C18—H18A⋯O4iii	0.96	2.52	3.469 (5)	171

Symmetry codes: (i) ; (ii) ; (iii) .