4-[(4-Diethyl­amino-2-hydroxy­benzyl­idene)ammonio]-3-methyl­benzene­sulfonate

Tai, X.-S.; Zhao, Z.-B.

doi:10.1107/S1600536809043098

organic compounds

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Volume 65| Part 11| November 2009| Page o2843

https://doi.org/10.1107/S1600536809043098

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4-[(4-Diethylamino-2-hydroxybenzylidene)ammonio]-3-methylbenzenesulfonate

Xi-Shi Tai ^a ^* and Zeng-Bing Zhao ^b

^aDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^bDepartment of Chemistry, Qinghai Normal University, Xining 810008, People's Republic of China
^*Correspondence e-mail: taixishi@lzu.edu.cn

(Received 17 October 2009; accepted 20 October 2009; online 23 October 2009)

In the zwitterionic title compound, C₁₈H₂₂N₂O₄S, the dihedral angle between the aromatic rings is 16.39 (11)° and an intramolecular N—H⋯O hydrogen bond occurs. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, forming chains propagating in [ $[\overline{1}]$ 01].

Related literature

For background to Schiff bases, see: Bu et al. (2001 ); Ranford et al. (1998 ).

Experimental

Crystal data

C₁₈H₂₂N₂O₄S
M_r = 362.44
Monoclinic, P 2₁ /n
a = 8.230 (9) Å
b = 12.143 (14) Å
c = 18.96 (2) Å
β = 96.848 (19)°
V = 1882 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 273 K
0.18 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
9430 measured reflections
3337 independent reflections
2737 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.136
S = 1.05
3337 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.86	1.99	2.668 (4)	135
O4—H4⋯O3ⁱ	0.82	1.84	2.623 (4)	160
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809043098/hb5148sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809043098/hb5148Isup2.hkl

checkCIF report

Comment top

Schiff bases play an important role in the field of bioinorganic chemistry because they have remarkable wide biological and pharmacological activities, such as antitumor, antidiabetic, antitubercular activities [Ranford, et al., 1998; Bu, et al., 2001]. In this paper, we report on the synthesis and crystal structure of the title compound, (I), (Scheme I).

The dihedral angle between the aromatic ring planes is 16.4, showing that the whole compound is not a plane molecule. The bond distances of C8—N1(1.335 (3)), S1—O1 (1.461 (3)) and S1—O2 (1.464 (2)) are consistent with the carbon-nitrogen and sulfur-oxygen double-bond lengths, respectively. In the crystal packing, the molecules form a one-dimensional chain structure by hydrogen bonds.

Related literature top

For background to Schiff bases, see: Bu et al. (2001); Ranford et al. (1998).

Experimental top

A solution of 1.0 mmol 4-(Diethylamino)salicylaldehyde was added to a solution of 1.0 mmol 3-methyl-benzenesulfonic acid in 5 ml ethanol at room temperature. The mixture was refluxed for 4 h with stirring, then the resulting precipitate was filtered, washed, and dried in vacuo over P₄O₁₀ for 48 h. Brown blocks of (I) were obtained by slowly evaporating from methanol at room temperature.

Structure description top

For background to Schiff bases, see: Bu et al. (2001); Ranford et al. (1998).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing 30% displacement ellipsoids.

4-[(4-Diethylamino-2-hydroxybenzylidene)ammonio]-3-methylbenzenesulfonate top

Crystal data top

C₁₈H₂₂N₂O₄S	F(000) = 768
M_r = 362.44	D_x = 1.279 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3420 reflections
a = 8.230 (9) Å	θ = 2.6–27.8°
b = 12.143 (14) Å	µ = 0.20 mm⁻¹
c = 18.96 (2) Å	T = 273 K
β = 96.848 (19)°	Block, brown
V = 1882 (4) Å³	0.18 × 0.16 × 0.12 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2737 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 25.1°, θ_min = 2.0°
ω scans	h = −9→9
9430 measured reflections	k = −13→14
3337 independent reflections	l = −19→22

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0682P)² + 0.8828P] where P = (F_o² + 2F_c²)/3
3337 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₈H₂₂N₂O₄S	V = 1882 (4) Å³
M_r = 362.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.230 (9) Å	µ = 0.20 mm⁻¹
b = 12.143 (14) Å	T = 273 K
c = 18.96 (2) Å	0.18 × 0.16 × 0.12 mm
β = 96.848 (19)°

Data collection top

Bruker SMART CCD diffractometer	2737 reflections with I > 2σ(I)
9430 measured reflections	R_int = 0.028
3337 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.05	Δρ_max = 0.44 e Å⁻³
3337 reflections	Δρ_min = −0.24 e Å⁻³
227 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.24693 (7)	0.19093 (5)	0.55953 (3)	0.0423 (2)
O1	0.2152 (3)	0.30892 (16)	0.56444 (12)	0.0792 (7)
O2	0.1087 (2)	0.12620 (16)	0.52607 (9)	0.0582 (5)
O3	0.3181 (2)	0.14533 (16)	0.62907 (8)	0.0561 (5)
O4	0.8678 (2)	0.22390 (14)	0.23964 (8)	0.0496 (4)
H4	0.8646	0.2536	0.2006	0.074*
N1	0.7742 (2)	0.15936 (16)	0.36312 (9)	0.0394 (4)
H1	0.7599	0.2026	0.3270	0.047*
N2	1.3356 (2)	0.04143 (18)	0.15486 (10)	0.0513 (5)
C1	0.4078 (3)	0.17934 (17)	0.50261 (11)	0.0359 (5)
C2	0.3808 (3)	0.22288 (18)	0.43351 (11)	0.0396 (5)
H2	0.2808	0.2558	0.4183	0.047*
C3	0.5015 (3)	0.21780 (18)	0.38679 (11)	0.0373 (5)
C4	0.6527 (3)	0.16570 (17)	0.41184 (11)	0.0349 (5)
C5	0.6818 (3)	0.1232 (2)	0.48125 (11)	0.0447 (6)
H5	0.7821	0.0911	0.4971	0.054*
C6	0.5588 (3)	0.1295 (2)	0.52658 (11)	0.0437 (6)
H6	0.5771	0.1008	0.5723	0.052*
C7	0.4692 (3)	0.2677 (2)	0.31182 (13)	0.0572 (7)
H7A	0.3545	0.2828	0.3008	0.086*
H7B	0.5030	0.2165	0.2778	0.086*
H7C	0.5300	0.3349	0.3101	0.086*
C8	0.9062 (3)	0.09465 (19)	0.36714 (11)	0.0394 (5)
H8	0.9291	0.0510	0.4074	0.047*
C9	1.0147 (3)	0.08791 (19)	0.31374 (11)	0.0381 (5)
C10	0.9949 (3)	0.15006 (18)	0.24798 (11)	0.0368 (5)
C11	1.0999 (3)	0.13405 (19)	0.19596 (11)	0.0410 (5)
H11	1.0830	0.1739	0.1539	0.049*
C12	1.2333 (3)	0.05717 (19)	0.20639 (11)	0.0408 (5)
C13	1.2563 (3)	−0.0028 (2)	0.27321 (12)	0.0456 (6)
H13	1.3434	−0.0516	0.2823	0.055*
C14	1.1492 (3)	0.0123 (2)	0.32326 (12)	0.0452 (6)
H14	1.1651	−0.0285	0.3650	0.054*
C15	1.3247 (3)	0.1109 (2)	0.08923 (13)	0.0555 (7)
H15A	1.4317	0.1149	0.0728	0.067*
H15B	1.2924	0.1850	0.1006	0.067*
C16	1.2015 (5)	0.0648 (3)	0.02963 (16)	0.0824 (10)
H16A	1.2287	−0.0102	0.0204	0.124*
H16B	1.2051	0.1079	−0.0126	0.124*
H16C	1.0934	0.0680	0.0438	0.124*
C17	1.4625 (3)	−0.0487 (2)	0.15911 (15)	0.0596 (7)
H17A	1.4728	−0.0754	0.1116	0.072*
H17B	1.4268	−0.1096	0.1865	0.072*
C18	1.6273 (4)	−0.0090 (3)	0.1931 (2)	0.0841 (10)
H18A	1.6586	0.0554	0.1687	0.126*
H18B	1.7073	−0.0659	0.1902	0.126*
H18C	1.6209	0.0086	0.2420	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0342 (3)	0.0489 (4)	0.0459 (3)	0.0009 (2)	0.0136 (2)	−0.0093 (2)
O1	0.0831 (15)	0.0529 (12)	0.1121 (17)	0.0114 (10)	0.0548 (13)	−0.0103 (11)
O2	0.0361 (9)	0.0829 (13)	0.0558 (10)	−0.0121 (9)	0.0062 (8)	−0.0059 (9)
O3	0.0521 (11)	0.0770 (12)	0.0408 (9)	0.0002 (9)	0.0121 (8)	−0.0073 (8)
O4	0.0489 (10)	0.0619 (10)	0.0405 (9)	0.0212 (8)	0.0156 (7)	0.0156 (8)
N1	0.0357 (10)	0.0501 (11)	0.0333 (9)	0.0066 (8)	0.0074 (7)	0.0048 (8)
N2	0.0420 (11)	0.0646 (13)	0.0501 (12)	0.0110 (10)	0.0170 (9)	0.0091 (10)
C1	0.0314 (11)	0.0381 (11)	0.0391 (11)	0.0000 (9)	0.0082 (9)	−0.0078 (9)
C2	0.0312 (11)	0.0421 (12)	0.0448 (12)	0.0058 (9)	0.0022 (9)	−0.0017 (10)
C3	0.0343 (11)	0.0395 (11)	0.0374 (11)	0.0018 (9)	0.0012 (9)	0.0011 (9)
C4	0.0328 (11)	0.0401 (12)	0.0325 (11)	0.0004 (9)	0.0065 (8)	−0.0028 (9)
C5	0.0344 (12)	0.0636 (15)	0.0364 (12)	0.0158 (11)	0.0057 (9)	0.0036 (10)
C6	0.0406 (13)	0.0595 (15)	0.0315 (11)	0.0107 (11)	0.0059 (9)	0.0037 (10)
C7	0.0469 (15)	0.0750 (18)	0.0496 (14)	0.0103 (13)	0.0048 (11)	0.0190 (13)
C8	0.0358 (12)	0.0511 (13)	0.0309 (11)	0.0024 (10)	0.0026 (9)	0.0037 (9)
C9	0.0336 (11)	0.0486 (13)	0.0320 (11)	0.0029 (10)	0.0038 (9)	0.0018 (9)
C10	0.0321 (11)	0.0426 (12)	0.0357 (11)	0.0030 (9)	0.0041 (9)	0.0018 (9)
C11	0.0381 (12)	0.0505 (13)	0.0352 (11)	0.0037 (10)	0.0077 (9)	0.0067 (10)
C12	0.0323 (11)	0.0508 (13)	0.0403 (12)	0.0019 (10)	0.0082 (9)	0.0007 (10)
C13	0.0349 (12)	0.0543 (14)	0.0480 (13)	0.0110 (11)	0.0063 (10)	0.0074 (11)
C14	0.0402 (13)	0.0569 (14)	0.0387 (12)	0.0088 (11)	0.0054 (10)	0.0118 (10)
C15	0.0516 (15)	0.0636 (16)	0.0552 (15)	0.0077 (13)	0.0231 (12)	0.0119 (12)
C16	0.104 (3)	0.084 (2)	0.0573 (18)	0.019 (2)	0.0021 (17)	−0.0009 (16)
C17	0.0518 (16)	0.0632 (17)	0.0674 (17)	0.0093 (13)	0.0218 (13)	0.0080 (13)
C18	0.0546 (18)	0.076 (2)	0.122 (3)	−0.0037 (16)	0.0109 (18)	0.021 (2)

Geometric parameters (Å, º) top

S1—O1	1.461 (3)	C7—H7C	0.9600
S1—O2	1.464 (2)	C8—C9	1.430 (3)
S1—O3	1.485 (2)	C8—H8	0.9300
S1—C1	1.811 (3)	C9—C14	1.433 (3)
O4—C10	1.372 (3)	C9—C10	1.450 (3)
O4—H4	0.8200	C10—C11	1.401 (3)
N1—C8	1.335 (3)	C11—C12	1.437 (3)
N1—C4	1.442 (3)	C11—H11	0.9300
N1—H1	0.8600	C12—C13	1.454 (3)
N2—C12	1.377 (3)	C13—C14	1.383 (3)
N2—C15	1.497 (3)	C13—H13	0.9300
N2—C17	1.508 (3)	C14—H14	0.9300
C1—C2	1.406 (3)	C15—C16	1.531 (4)
C1—C6	1.408 (3)	C15—H15A	0.9700
C2—C3	1.409 (3)	C15—H15B	0.9700
C2—H2	0.9300	C16—H16A	0.9600
C3—C4	1.426 (3)	C16—H16B	0.9600
C3—C7	1.539 (3)	C16—H16C	0.9600
C4—C5	1.407 (3)	C17—C18	1.509 (4)
C5—C6	1.406 (3)	C17—H17A	0.9700
C5—H5	0.9300	C17—H17B	0.9700
C6—H6	0.9300	C18—H18A	0.9600
C7—H7A	0.9600	C18—H18B	0.9600
C7—H7B	0.9600	C18—H18C	0.9600

O1—S1—O2	114.73 (14)	C8—C9—C10	124.3 (2)
O1—S1—O3	111.33 (13)	C14—C9—C10	116.60 (19)
O2—S1—O3	112.88 (12)	O4—C10—C11	122.38 (19)
O1—S1—C1	105.25 (11)	O4—C10—C9	116.42 (18)
O2—S1—C1	106.60 (12)	C11—C10—C9	121.2 (2)
O3—S1—C1	105.14 (12)	C10—C11—C12	121.3 (2)
C10—O4—H4	109.5	C10—C11—H11	119.4
C8—N1—C4	128.05 (19)	C12—C11—H11	119.4
C8—N1—H1	116.0	N2—C12—C11	121.0 (2)
C4—N1—H1	116.0	N2—C12—C13	121.4 (2)
C12—N2—C15	122.0 (2)	C11—C12—C13	117.61 (19)
C12—N2—C17	122.8 (2)	C14—C13—C12	120.3 (2)
C15—N2—C17	115.20 (19)	C14—C13—H13	119.9
C2—C1—C6	119.88 (19)	C12—C13—H13	119.9
C2—C1—S1	118.72 (17)	C13—C14—C9	123.0 (2)
C6—C1—S1	121.39 (18)	C13—C14—H14	118.5
C1—C2—C3	121.6 (2)	C9—C14—H14	118.5
C1—C2—H2	119.2	N2—C15—C16	112.1 (2)
C3—C2—H2	119.2	N2—C15—H15A	109.2
C2—C3—C4	117.6 (2)	C16—C15—H15A	109.2
C2—C3—C7	120.4 (2)	N2—C15—H15B	109.2
C4—C3—C7	122.0 (2)	C16—C15—H15B	109.2
C5—C4—C3	121.26 (19)	H15A—C15—H15B	107.9
C5—C4—N1	121.70 (19)	C15—C16—H16A	109.5
C3—C4—N1	117.04 (19)	C15—C16—H16B	109.5
C6—C5—C4	119.8 (2)	H16A—C16—H16B	109.5
C6—C5—H5	120.1	C15—C16—H16C	109.5
C4—C5—H5	120.1	H16A—C16—H16C	109.5
C5—C6—C1	119.9 (2)	H16B—C16—H16C	109.5
C5—C6—H6	120.1	N2—C17—C18	111.9 (3)
C1—C6—H6	120.1	N2—C17—H17A	109.2
C3—C7—H7A	109.5	C18—C17—H17A	109.2
C3—C7—H7B	109.5	N2—C17—H17B	109.2
H7A—C7—H7B	109.5	C18—C17—H17B	109.2
C3—C7—H7C	109.5	H17A—C17—H17B	107.9
H7A—C7—H7C	109.5	C17—C18—H18A	109.5
H7B—C7—H7C	109.5	C17—C18—H18B	109.5
N1—C8—C9	124.4 (2)	H18A—C18—H18B	109.5
N1—C8—H8	117.8	C17—C18—H18C	109.5
C9—C8—H8	117.8	H18A—C18—H18C	109.5
C8—C9—C14	119.0 (2)	H18B—C18—H18C	109.5

O1—S1—C1—C2	−58.2 (2)	N1—C8—C9—C10	−0.4 (4)
O2—S1—C1—C2	64.0 (2)	C8—C9—C10—O4	3.7 (3)
O3—S1—C1—C2	−175.90 (17)	C14—C9—C10—O4	−178.8 (2)
O1—S1—C1—C6	120.8 (2)	C8—C9—C10—C11	−175.8 (2)
O2—S1—C1—C6	−117.0 (2)	C14—C9—C10—C11	1.7 (3)
O3—S1—C1—C6	3.1 (2)	O4—C10—C11—C12	179.2 (2)
C6—C1—C2—C3	0.2 (3)	C9—C10—C11—C12	−1.3 (3)
S1—C1—C2—C3	179.24 (17)	C15—N2—C12—C11	6.4 (4)
C1—C2—C3—C4	0.6 (3)	C17—N2—C12—C11	−171.6 (2)
C1—C2—C3—C7	−179.1 (2)	C15—N2—C12—C13	−173.4 (2)
C2—C3—C4—C5	−1.5 (3)	C17—N2—C12—C13	8.6 (4)
C7—C3—C4—C5	178.2 (2)	C10—C11—C12—N2	179.7 (2)
C2—C3—C4—N1	178.98 (19)	C10—C11—C12—C13	−0.5 (3)
C7—C3—C4—N1	−1.3 (3)	N2—C12—C13—C14	−178.2 (2)
C8—N1—C4—C5	17.3 (3)	C11—C12—C13—C14	1.9 (3)
C8—N1—C4—C3	−163.2 (2)	C12—C13—C14—C9	−1.6 (4)
C3—C4—C5—C6	1.5 (3)	C8—C9—C14—C13	177.4 (2)
N1—C4—C5—C6	−178.9 (2)	C10—C9—C14—C13	−0.3 (3)
C4—C5—C6—C1	−0.7 (4)	C12—N2—C15—C16	−87.6 (3)
C2—C1—C6—C5	−0.2 (3)	C17—N2—C15—C16	90.5 (3)
S1—C1—C6—C5	−179.17 (18)	C12—N2—C17—C18	−93.3 (3)
C4—N1—C8—C9	175.3 (2)	C15—N2—C17—C18	88.5 (3)
N1—C8—C9—C14	−177.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	1.99	2.668 (4)	135
O4—H4···O3ⁱ	0.82	1.84	2.623 (4)	160

Symmetry code: (i) x+1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₂N₂O₄S
M_r	362.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	8.230 (9), 12.143 (14), 18.96 (2)
β (°)	96.848 (19)
V (Å³)	1882 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.18 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9430, 3337, 2737
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.136, 1.05
No. of reflections	3337
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.24

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	1.99	2.668 (4)	135
O4—H4···O3ⁱ	0.82	1.84	2.623 (4)	160

Symmetry code: (i) x+1/2, −y+1/2, z−1/2.

Acknowledgements

This project was supported by the National Natural Science Foundation of China (20671073), the Natural Science Foundation of Shandong (Y2007B60) and Science Foundation of Weifang University.

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bu, X. H., Gao, Y. X., Chen, W. & Zhang, R. H. (2001). J. Rare Earth, 19, 70–75. Google Scholar
Ranford, J. D., Vittal, J. J. & Wang, Y. M. (1998). Inorg. Chem. 37, 1226–1231. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 11| November 2009| Page o2843

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

4-[(4-Di­ethyl­amino-2-hy­droxy­benzyl­­idene)ammonio]-3-methyl­benzene­sulfonate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-[(4-Diethylamino-2-hydroxybenzylidene)ammonio]-3-methylbenzenesulfonate