4-[(4-Diethyl-amino-2-hydroxy-benzyl-idene)ammonio]-3-methyl-benzene-sulfonate.

In the zwitterionic title compound, C(18)H(22)N(2)O(4)S, the dihedral angle between the aromatic rings is 16.39 (11)° and an intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, forming chains propagating in [01].

Related literature

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

Experimental

Crystal data

C18H22N2O4S

M = 362.44

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.136

S = 1.05

3337 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.24 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043098/hb5148Isup2.hkl

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

C18H22N2O4S	F(000) = 768
Mr = 362.44	Dx = 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

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

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(Fo2) + (0.0682P)2 + 0.8828P] where P = (Fo2 + 2Fc2)/3
3337 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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
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*

	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)

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)

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

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) .