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

In the crystal of the title compound, C(18)H(22)N(2)O(4)S·2H(2)O, mol-ecules are linked into a one-dimensional chain structure by C-H⋯O, N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds.

Related literature

For the biological and pharmacological activities of Schiff base compounds, see: Bu et al. (2001 ▶); Ranford et al. (1998 ▶).

Experimental

Crystal data

C18H22N2O4S·2H2O

M = 398.47

Monoclinic,

a = 21.690 (3) Å

b = 11.4142 (17) Å

c = 16.639 (2) Å

β = 112.459 (2)°

V = 3806.9 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 273 K

0.19 × 0.16 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.962, T max = 0.988

9821 measured reflections

3379 independent reflections

2910 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.171

S = 1.05

3379 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.41 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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/S1600536809035090/at2871sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035090/at2871Isup2.hkl

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

C18H22N2O4S·2H2O	F(000) = 1696
Mr = 398.47	Dx = 1.390 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4718 reflections
a = 21.690 (3) Å	θ = 2.2–28.4°
b = 11.4142 (17) Å	µ = 0.21 mm−1
c = 16.639 (2) Å	T = 273 K
β = 112.459 (2)°	Block, colourless
V = 3806.9 (9) Å3	0.19 × 0.16 × 0.06 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	3379 independent reflections
Radiation source: fine-focus sealed tube	2910 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→25
Tmin = 0.962, Tmax = 0.988	k = −13→13
9821 measured reflections	l = −19→19

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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.171	w = 1/[σ2(Fo2) + (0.1015P)2 + 5.082P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3379 reflections	Δρmax = 0.73 e Å−3
246 parameters	Δρmin = −0.41 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0019 (5)

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	0.18156 (3)	0.09473 (5)	−0.21298 (4)	0.0405 (3)
O1	0.17722 (12)	0.1276 (2)	−0.29916 (14)	0.0750 (8)
O2	0.11837 (9)	0.1127 (2)	−0.20400 (13)	0.0573 (6)
O3	0.20786 (13)	−0.0203 (2)	−0.1892 (2)	0.0980 (11)
O4	0.18994 (19)	0.6795 (4)	0.0958 (2)	0.1365 (14)
H16	0.2252	0.6420	0.1254	0.205*
H15	0.1630	0.6669	0.1209	0.205*
O5	0.276 (2)	0.6202 (16)	1.001 (2)	0.81 (3)
H18	0.3031	0.5664	1.0016	1.213*
H17	0.2582	0.6426	0.9487	1.213*
O6	0.50747 (8)	0.45092 (15)	0.15864 (11)	0.0392 (4)
H6	0.5392	0.4405	0.2047	0.059*
N1	0.39104 (9)	0.41470 (17)	0.02004 (12)	0.0332 (5)
H1	0.4154	0.3891	0.0709	0.040*
N2	0.60480 (10)	0.83477 (18)	0.19161 (14)	0.0404 (5)
C1	0.24039 (11)	0.1925 (2)	−0.13942 (15)	0.0343 (5)
C2	0.28796 (12)	0.1511 (2)	−0.06245 (15)	0.0345 (5)
H2	0.2863	0.0733	−0.0468	0.041*
C3	0.33840 (11)	0.2239 (2)	−0.00783 (14)	0.0306 (5)
C4	0.33861 (11)	0.3409 (2)	−0.03262 (14)	0.0303 (5)
C5	0.28903 (12)	0.3837 (2)	−0.10848 (16)	0.0387 (6)
H5	0.2886	0.4624	−0.1230	0.046*
C6	0.24063 (12)	0.3090 (2)	−0.16183 (16)	0.0412 (6)
H6A	0.2081	0.3371	−0.2129	0.049*
C7	0.39164 (13)	0.1746 (2)	0.07302 (16)	0.0442 (6)
H7A	0.3837	0.0925	0.0774	0.066*
H7B	0.3905	0.2145	0.1232	0.066*
H7C	0.4346	0.1853	0.0700	0.066*
C8	0.40592 (11)	0.5183 (2)	−0.00150 (15)	0.0338 (5)
H8	0.3790	0.5459	−0.0563	0.041*
C9	0.45786 (11)	0.59191 (19)	0.04893 (15)	0.0322 (5)
C10	0.50910 (11)	0.5615 (2)	0.13088 (14)	0.0304 (5)
C11	0.55669 (11)	0.6412 (2)	0.17671 (15)	0.0343 (5)
H11	0.5891	0.6194	0.2299	0.041*
C12	0.55782 (11)	0.7562 (2)	0.14517 (16)	0.0355 (5)
C13	0.50789 (13)	0.7859 (2)	0.06268 (17)	0.0417 (6)
H13	0.5073	0.8605	0.0400	0.050*
C14	0.46131 (13)	0.7060 (2)	0.01705 (16)	0.0412 (6)
H14	0.4303	0.7270	−0.0374	0.049*
C15	0.65369 (14)	0.8065 (3)	0.27868 (18)	0.0514 (7)
H15A	0.6912	0.8598	0.2929	0.062*
H15B	0.6702	0.7277	0.2782	0.062*
C16	0.6252 (3)	0.8148 (4)	0.3481 (2)	0.0935 (13)
H16A	0.5824	0.7771	0.3282	0.140*
H16B	0.6203	0.8957	0.3603	0.140*
H16C	0.6547	0.7768	0.4000	0.140*
C17	0.60749 (14)	0.9541 (2)	0.1600 (2)	0.0490 (7)
H17A	0.5944	0.9516	0.0973	0.059*
H17B	0.6532	0.9818	0.1850	0.059*
C18	0.56346 (19)	1.0404 (3)	0.1815 (3)	0.0720 (10)
H18A	0.5791	1.0499	0.2434	0.108*
H18B	0.5185	1.0116	0.1598	0.108*
H18C	0.5648	1.1145	0.1549	0.108*

	U11	U22	U33	U12	U13	U23
S1	0.0310 (4)	0.0404 (4)	0.0444 (4)	−0.0065 (2)	0.0080 (3)	−0.0132 (3)
O1	0.0836 (16)	0.1016 (18)	0.0462 (12)	−0.0473 (14)	0.0318 (12)	−0.0338 (12)
O2	0.0341 (10)	0.0851 (15)	0.0515 (11)	−0.0193 (9)	0.0150 (8)	−0.0287 (10)
O3	0.0664 (15)	0.0437 (13)	0.128 (2)	0.0007 (11)	−0.0253 (15)	−0.0222 (14)
O4	0.102 (3)	0.148 (3)	0.120 (3)	0.026 (2)	−0.002 (2)	0.010 (2)
O5	1.22 (7)	0.36 (2)	1.12 (5)	−0.11 (3)	0.75 (6)	−0.22 (3)
O6	0.0317 (9)	0.0359 (9)	0.0378 (9)	−0.0044 (7)	−0.0004 (7)	0.0086 (7)
N1	0.0283 (10)	0.0372 (11)	0.0262 (10)	−0.0048 (8)	0.0018 (8)	0.0015 (8)
N2	0.0344 (11)	0.0346 (11)	0.0480 (12)	−0.0076 (9)	0.0112 (9)	−0.0070 (9)
C1	0.0255 (11)	0.0394 (13)	0.0366 (12)	−0.0036 (9)	0.0101 (10)	−0.0069 (10)
C2	0.0353 (12)	0.0305 (12)	0.0386 (13)	−0.0035 (9)	0.0150 (10)	−0.0023 (9)
C3	0.0296 (11)	0.0340 (12)	0.0279 (11)	0.0010 (9)	0.0106 (9)	0.0014 (9)
C4	0.0271 (11)	0.0359 (12)	0.0266 (11)	−0.0046 (9)	0.0087 (9)	−0.0020 (9)
C5	0.0355 (13)	0.0324 (12)	0.0380 (13)	−0.0030 (10)	0.0027 (10)	0.0054 (10)
C6	0.0332 (13)	0.0428 (14)	0.0363 (13)	−0.0028 (10)	0.0005 (10)	0.0015 (10)
C7	0.0459 (15)	0.0393 (14)	0.0376 (13)	0.0019 (11)	0.0049 (11)	0.0055 (10)
C8	0.0305 (12)	0.0382 (13)	0.0284 (11)	−0.0007 (9)	0.0066 (9)	0.0026 (9)
C9	0.0278 (12)	0.0349 (12)	0.0304 (12)	−0.0024 (9)	0.0073 (9)	0.0012 (9)
C10	0.0269 (11)	0.0323 (11)	0.0304 (11)	−0.0003 (9)	0.0091 (9)	0.0022 (9)
C11	0.0279 (11)	0.0361 (12)	0.0332 (12)	0.0001 (9)	0.0053 (9)	0.0001 (9)
C12	0.0309 (12)	0.0356 (13)	0.0417 (13)	−0.0022 (10)	0.0157 (10)	−0.0053 (10)
C13	0.0430 (14)	0.0343 (13)	0.0427 (14)	−0.0049 (10)	0.0105 (11)	0.0065 (10)
C14	0.0394 (14)	0.0411 (14)	0.0354 (13)	−0.0014 (10)	0.0056 (11)	0.0078 (10)
C15	0.0443 (16)	0.0477 (16)	0.0514 (16)	−0.0131 (12)	0.0061 (13)	−0.0089 (12)
C16	0.137 (4)	0.091 (3)	0.053 (2)	0.004 (3)	0.038 (2)	−0.004 (2)
C17	0.0440 (15)	0.0393 (14)	0.0621 (17)	−0.0096 (12)	0.0185 (13)	−0.0068 (13)
C18	0.072 (2)	0.0533 (19)	0.089 (3)	0.0109 (17)	0.0290 (19)	−0.0022 (17)

S1—O3	1.426 (2)	C7—H7A	0.9600
S1—O2	1.449 (2)	C7—H7B	0.9600
S1—O1	1.450 (2)	C7—H7C	0.9600
S1—C1	1.783 (2)	C8—C9	1.399 (3)
O4—H16	0.8502	C8—H8	0.9300
O4—H15	0.8505	C9—C14	1.419 (3)
O5—H18	0.8491	C9—C10	1.434 (3)
O5—H17	0.8505	C10—C11	1.369 (3)
O6—C10	1.349 (3)	C11—C12	1.417 (3)
O6—H6	0.8200	C11—H11	0.9300
N1—C8	1.311 (3)	C12—C13	1.427 (3)
N1—C4	1.417 (3)	C13—C14	1.357 (3)
N1—H1	0.8600	C13—H13	0.9300
N2—C12	1.356 (3)	C14—H14	0.9300
N2—C15	1.467 (3)	C15—C16	1.507 (5)
N2—C17	1.470 (3)	C15—H15A	0.9700
C1—C6	1.382 (4)	C15—H15B	0.9700
C1—C2	1.385 (3)	C16—H16A	0.9600
C2—C3	1.398 (3)	C16—H16B	0.9600
C2—H2	0.9300	C16—H16C	0.9600
C3—C4	1.399 (3)	C17—C18	1.506 (4)
C3—C7	1.508 (3)	C17—H17A	0.9700
C4—C5	1.397 (3)	C17—H17B	0.9700
C5—C6	1.380 (3)	C18—H18A	0.9600
C5—H5	0.9300	C18—H18B	0.9600
C6—H6A	0.9300	C18—H18C	0.9600
O3—S1—O2	113.29 (17)	C8—C9—C14	118.2 (2)
O3—S1—O1	112.40 (19)	C8—C9—C10	125.4 (2)
O2—S1—O1	111.02 (14)	C14—C9—C10	116.4 (2)
O3—S1—C1	106.26 (12)	O6—C10—C11	123.0 (2)
O2—S1—C1	107.32 (11)	O6—C10—C9	116.08 (19)
O1—S1—C1	106.02 (12)	C11—C10—C9	121.0 (2)
H16—O4—H15	105.3	C10—C11—C12	121.7 (2)
H18—O5—H17	105.4	C10—C11—H11	119.1
C10—O6—H6	109.5	C12—C11—H11	119.1
C8—N1—C4	126.16 (19)	N2—C12—C11	121.1 (2)
C8—N1—H1	116.9	N2—C12—C13	121.4 (2)
C4—N1—H1	116.9	C11—C12—C13	117.5 (2)
C12—N2—C15	121.3 (2)	C14—C13—C12	120.5 (2)
C12—N2—C17	122.2 (2)	C14—C13—H13	119.7
C15—N2—C17	116.4 (2)	C12—C13—H13	119.7
C6—C1—C2	120.0 (2)	C13—C14—C9	122.8 (2)
C6—C1—S1	119.52 (18)	C13—C14—H14	118.6
C2—C1—S1	120.39 (18)	C9—C14—H14	118.6
C1—C2—C3	121.3 (2)	N2—C15—C16	112.9 (3)
C1—C2—H2	119.3	N2—C15—H15A	109.0
C3—C2—H2	119.3	C16—C15—H15A	109.0
C2—C3—C4	117.8 (2)	N2—C15—H15B	109.0
C2—C3—C7	120.1 (2)	C16—C15—H15B	109.0
C4—C3—C7	122.1 (2)	H15A—C15—H15B	107.8
C5—C4—C3	120.8 (2)	C15—C16—H16A	109.5
C5—C4—N1	120.7 (2)	C15—C16—H16B	109.5
C3—C4—N1	118.52 (19)	H16A—C16—H16B	109.5
C6—C5—C4	119.9 (2)	C15—C16—H16C	109.5
C6—C5—H5	120.0	H16A—C16—H16C	109.5
C4—C5—H5	120.0	H16B—C16—H16C	109.5
C5—C6—C1	120.1 (2)	N2—C17—C18	113.9 (3)
C5—C6—H6A	120.0	N2—C17—H17A	108.8
C1—C6—H6A	120.0	C18—C17—H17A	108.8
C3—C7—H7A	109.5	N2—C17—H17B	108.8
C3—C7—H7B	109.5	C18—C17—H17B	108.8
H7A—C7—H7B	109.5	H17A—C17—H17B	107.7
C3—C7—H7C	109.5	C17—C18—H18A	109.5
H7A—C7—H7C	109.5	C17—C18—H18B	109.5
H7B—C7—H7C	109.5	H18A—C18—H18B	109.5
N1—C8—C9	127.1 (2)	C17—C18—H18C	109.5
N1—C8—H8	116.4	H18A—C18—H18C	109.5
C9—C8—H8	116.4	H18B—C18—H18C	109.5
O3—S1—C1—C6	159.2 (2)	N1—C8—C9—C10	7.0 (4)
O2—S1—C1—C6	−79.3 (2)	C8—C9—C10—O6	2.7 (3)
O1—S1—C1—C6	39.4 (2)	C14—C9—C10—O6	−176.7 (2)
O3—S1—C1—C2	−17.3 (3)	C8—C9—C10—C11	−177.9 (2)
O2—S1—C1—C2	104.2 (2)	C14—C9—C10—C11	2.7 (3)
O1—S1—C1—C2	−137.1 (2)	O6—C10—C11—C12	178.9 (2)
C6—C1—C2—C3	−2.6 (4)	C9—C10—C11—C12	−0.6 (4)
S1—C1—C2—C3	173.88 (17)	C15—N2—C12—C11	−3.9 (4)
C1—C2—C3—C4	1.2 (3)	C17—N2—C12—C11	179.4 (2)
C1—C2—C3—C7	−176.6 (2)	C15—N2—C12—C13	176.3 (2)
C2—C3—C4—C5	1.4 (3)	C17—N2—C12—C13	−0.4 (4)
C7—C3—C4—C5	179.2 (2)	C10—C11—C12—N2	179.3 (2)
C2—C3—C4—N1	−177.30 (19)	C10—C11—C12—C13	−1.0 (3)
C7—C3—C4—N1	0.5 (3)	N2—C12—C13—C14	179.9 (2)
C8—N1—C4—C5	−12.5 (4)	C11—C12—C13—C14	0.2 (4)
C8—N1—C4—C3	166.3 (2)	C12—C13—C14—C9	2.2 (4)
C3—C4—C5—C6	−2.7 (4)	C8—C9—C14—C13	177.0 (2)
N1—C4—C5—C6	176.0 (2)	C10—C9—C14—C13	−3.6 (4)
C4—C5—C6—C1	1.3 (4)	C12—N2—C15—C16	−78.0 (3)
C2—C1—C6—C5	1.3 (4)	C17—N2—C15—C16	98.9 (3)
S1—C1—C6—C5	−175.2 (2)	C12—N2—C17—C18	85.9 (3)
C4—N1—C8—C9	−179.1 (2)	C15—N2—C17—C18	−91.0 (3)
N1—C8—C9—C14	−173.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6	0.86	2.10	2.723 (3)	129
N1—H1···O2i	0.86	2.58	3.160 (3)	125
O6—H6···O2ii	0.82	1.91	2.709 (3)	166
O4—H16···O3i	0.85	2.00	2.828 (5)	166
O5—H18···N1iii	0.85	2.51	3.35 (3)	174
C2—H2···O3	0.93	2.56	2.915 (4)	103
C5—H5···O1iv	0.93	2.55	3.392 (3)	150
C7—H7B···O2i	0.96	2.44	3.325 (3)	154
C8—H8···O1iv	0.93	2.43	3.353 (3)	172
C15—H15B···O3ii	0.97	2.50	3.444 (4)	166
C16—H16C···O5v	0.96	2.51	3.42 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6	0.86	2.10	2.723 (3)	129
N1—H1⋯O2i	0.86	2.58	3.160 (3)	125
O6—H6⋯O2ii	0.82	1.91	2.709 (3)	166
O4—H16⋯O3i	0.85	2.00	2.828 (5)	166
O5—H18⋯N1iii	0.85	2.51	3.35 (3)	174
C2—H2⋯O3	0.93	2.56	2.915 (4)	103
C5—H5⋯O1iv	0.93	2.55	3.392 (3)	150
C7—H7B⋯O2i	0.96	2.44	3.325 (3)	154
C8—H8⋯O1iv	0.93	2.43	3.353 (3)	172
C15—H15B⋯O3ii	0.97	2.50	3.444 (4)	166
C16—H16C⋯O5v	0.96	2.51	3.42 (3)	160

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