2-[(E)-({4-[(4,6-Dimethyl­pyrimidin-2-yl)sulfamo­yl]phen­yl}iminio)meth­yl]-6-hy­droxy­phenolate

Tahir, M.N.; Khan, A.H.; Iqbal, M.S.; Shad, H.A.; Yaqub, M.

doi:10.1107/S1600536812034757

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2687

doi:10.1107/S1600536812034757

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2-[(E)-({4-[(4,6-Dimethylpyrimidin-2-yl)sulfamoyl]phenyl}iminio)methyl]-6-hydroxyphenolate

M. Nawaz Tahir,^a ^* Abdul Haleem Khan,^b Mohammad S. Iqbal,^c Hazoor Ahmad Shad ^d and Muhammad Yaqub ^e

^aDepartment of Physics, University of Sargodha, Sargodha, Pakistan, ^bDepartment of Pharmacy Services, Jinnah Hospital, Lahore, Pakistan, ^cDepartment of Chemistry, Forman Christian College, Lahore 54600, Pakistan, ^dDepartment of Chemistry, Government Post Graduate College, Gojra, Punjab, Pakistan, and ^eDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 21 July 2012; accepted 5 August 2012; online 11 August 2012)

The title compound, C₁₉H₁₈N₄O₄S, exists as a zwitterion in the solid state, with nominal proton transfer from a phenol group to the imine N atom. The 2,3-dihydroxybenzaldehyde 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-dimethylpyrimidin-2-amine group. Intramolecular 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 molecules joined end-to-end by N—H⋯O and O—H⋯N hydrogen bonds; these feature R₂³(6) loops. The polymeric chains are linked by C—H⋯O interactions and there are π–π interactions 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_r = 398.43
Orthorhombic, P b c n
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[F² > 2σ(F²)] = 0.054
wR(F²) = 0.151
S = 1.01
3796 reflections
259 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.78 (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) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034757/hb6908sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812034757/hb6908Isup3.cml

checkCIF report

Comment top

We have reported the crystal structure of 4-{[(E)-(2,3-dihydroxyphenyl) methylidene]amino}-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide (Tahir et al., 2012) and the title compound (I), (Fig. 1) has also been synthesized for the biological studies and forming different metal complexes.

The crystal structures of 4-(5-chloro-2-hydroxybenzylideneamino)-N- (4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (Chohan et al., 2008) and 4-[(5-bromo-2-hydroxybenzylidene)amino]-N-(4,6-dimethylpyrimidin- 2-yl)benzenesulfonamide–4-bromo-2-[(E)-({4-[(4,6-dimethylpyrimidin-2-yl) sulfamoyl]phenyl}iminio)methyl]phenolate (Shad et al., 2009) have been published which are related to the title compound.

In (I) the parts of 2,3-dihydroxybenzaldehyde A (C1—C7/O1/O2), annilinic group B (C8—C13/N1) and 4,6-dimethylpyrimidin-2-amine C (C14—C19/N2/N3/N4) are planar with r.m.s. deviation of 0.0105, 0.0070 and 0.0216 Å, respectively. The dihedral angle between A/B, A/C and B/C is 35.51 (11)°, 76.99 (6)° and 88.92 (6)°, respectively. The sulfonyl group D (O3/S1/O4) is of course planar. The dihedral angle between A/D, B/D and C/D is 62.20 (13)°, 47.66 (17)° and 50.34 (15)°, respectively. In (I), S(5) and S(6) ring motif (Bernstein et al., 1995) are present due to H-bondings of O—H···O and N—H···O types, respectively (Table 1, Fig. 1). The molecules are interlinked from end to end due to H-bondings of N—H···O and O—H···O types (Table 1, Fig. 2). Due to these bondings R₂³(6) loops are also formed. The molecules are interlinked in the form of polymeric chains along the c-axis. The polymeric chains are also interlinked due to C–H···O bondings (Table 1, Fig. 2), Where CH is of methyl group and O-atom is of sulfonyl group. There exist π–π interaction between Cg1···Cg1ⁱ [i = 1 - x, y, 1/2 - z] at a distance of 3.446 (2) Å, where Cg1 is the centroid of pyrimidin ring (C14—C17/N3/N4).

Related literature top

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 top

Equimolar quantities of 4-amino-N-(4,6-dimethylpyrimidin-2-yl) benzenesulfonamide (Sulfamethazine) and 2,3-dihydroxybenzaldehyde were refluxed in methanol along with few drops of acetic acid as catalyst for 3 h. The solution was kept at room temperature which afforded dark red plates after four days upon slow evaporation of the solvent.

Computing details top

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

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level. The dotted lines represent the intramolecular H-bonds.
	Fig. 2. The partial packing, which shows that molecules form polymeric chains along [001]. The H-atoms not involved in H-bondings are omitted for clarity.

2-[(E)-({4-[(4,6-Dimethylpyrimidin-2-yl)sulfamoyl]phenyl}iminio)methyl]- 6-hydroxyphenolate top

Crystal data top

C₁₉H₁₈N₄O₄S	F(000) = 1664
M_r = 398.43	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	3796 independent reflections
Radiation source: fine-focus sealed tube	1778 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
Detector resolution: 8.00 pixels mm^-1	θ_max = 26.0°, θ_min = 1.7°
ω scans	h = −30→29
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
T_min = 0.935, T_max = 0.971	l = −15→14
16627 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)] = 0.054	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(F_o²) + (0.0534P)² + 1.0105P] where P = (F_o² + 2F_c²)/3
3796 reflections	(Δ/σ)_max < 0.001
259 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₉H₁₈N₄O₄S	V = 3867.5 (3) Å³
M_r = 398.43	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 24.7506 (12) Å	µ = 0.20 mm⁻¹
b = 12.1689 (6) Å	T = 296 K
c = 12.8408 (5) Å	0.34 × 0.28 × 0.15 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3796 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1778 reflections with I > 2σ(I)
T_min = 0.935, T_max = 0.971	R_int = 0.069
16627 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.21 e Å⁻³
3796 reflections	Δρ_min = −0.28 e Å⁻³
259 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 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈N₄O₄S
M_r	398.43
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	296
a, b, c (Å)	24.7506 (12), 12.1689 (6), 12.8408 (5)
V (Å³)	3867.5 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.34 × 0.28 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.935, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	16627, 3796, 1778
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.151, 1.01
No. of reflections	3796
No. of parameters	259
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chohan, Z. H., Tahir, M. N., Shad, H. A. & Khan, I. U. (2008). Acta Cryst. E64, o648. Web of Science 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
Shad, H. A., Tahir, M. N. & Chohan, Z. H. (2009). Acta Cryst. E65, o98–o99. Web of Science CSD CrossRef 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
Tahir, M. N., Khan, A. H., Iqbal, M. S., Munir, C. & Aziz, T. (2012). Acta Cryst. E68, o2125. CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 9| September 2012| Page o2687

doi:10.1107/S1600536812034757

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

2-[(E)-({4-[(4,6-Di­methyl­pyrimidin-2-yl)sulfamo­yl]phen­yl}iminio)meth­yl]-6-hy­dr­oxy­phenolate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[(E)-({4-[(4,6-Dimethylpyrimidin-2-yl)sulfamoyl]phenyl}iminio)methyl]-6-hydroxyphenolate