4-(4-Diethyl­amino-2-hydroxy­benzyl­idene­ammonio)-3-methyl­benzene­sulfonate dihydrate

Zhang, W.; Chen, Y.-T.

doi:10.1107/S1600536809035090

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2339

doi:10.1107/S1600536809035090

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4-(4-Diethylamino-2-hydroxybenzylideneammonio)-3-methylbenzenesulfonate dihydrate

Wei Zhang ^a and Yuan-Tao Chen ^a ^*

^aDepartment of Chemistry, Qinghai Normal University, Xining 810008, People's Republic of China
^*Correspondence e-mail: chenyt@qhnu.edu.cn

(Received 27 August 2009; accepted 1 September 2009; online 5 September 2009)

In the crystal of the title compound, C₁₈H₂₂N₂O₄S·2H₂O, molecules 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_r = 398.47
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.054
wR(F²) = 0.171
S = 1.05
3379 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.41 e Å⁻³

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⋯O1^iv	0.93	2.55	3.392 (3)	150
C7—H7B⋯O2ⁱ	0.96	2.44	3.325 (3)	154
C8—H8⋯O1^iv	0.93	2.43	3.353 (3)	172
C15—H15B⋯O3ⁱⁱ	0.97	2.50	3.444 (4)	166
C16—H16C⋯O5^v	0.96	2.51	3.42 (3)	160
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x, y, z+1; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (v) $[-x+1, y, -z+{\script{3\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035090/at2871sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809035090/at2871Isup2.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]. Therefore, investigating the synthesis and proper ties of hydrazone of these compounds seems to be a very interesting problem. as one part of our systematic work, In this paper, we report on the synthesis and crystal structure of the title compound, (I), (Fig. 1).

The dihedral angle between the aromatic ring planes (C1–C6) and (C9–C14) is 5.70 (12)°, showing that the whole compound is not a plane molecule. The bond distances of C8—N1 [1.311 (3) Å], S1—O2 [1.449 (2) Å] and S1—O3 [1.426 (3) Å] 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 C—H···O, N—H···O, O—H···O and O—H···N hydrogen bonds (Table 1).

Related literature top

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

Experimental top

The 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. Single crystals suitable for X-ray structural analysis was obtained by slowly evaporating from methanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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-hydroxybenzylideneammonio)-3-methylbenzenesulfonate dihydrate top

Crystal data top

C₁₈H₂₂N₂O₄S·2H₂O	F(000) = 1696
M_r = 398.47	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1015P)² + 5.082P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3379 reflections	Δρ_max = 0.73 e Å⁻³
246 parameters	Δρ_min = −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)

Crystal data top

C₁₈H₂₂N₂O₄S·2H₂O	V = 3806.9 (9) Å³
M_r = 398.47	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.690 (3) Å	µ = 0.21 mm⁻¹
b = 11.4142 (17) Å	T = 273 K
c = 16.639 (2) Å	0.19 × 0.16 × 0.06 mm
β = 112.459 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3379 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2910 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.988	R_int = 0.026
9821 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.171	H-atom parameters constrained
S = 1.05	Δρ_max = 0.73 e Å⁻³
3379 reflections	Δρ_min = −0.41 e Å⁻³
246 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	0.18156 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.93	2.55	3.392 (3)	150
C7—H7B···O2ⁱ	0.96	2.44	3.325 (3)	154
C8—H8···O1^iv	0.93	2.43	3.353 (3)	172
C15—H15B···O3ⁱⁱ	0.97	2.50	3.444 (4)	166
C16—H16C···O5^v	0.96	2.51	3.42 (3)	160

Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) x+1/2, −y+1/2, z+1/2; (iii) x, y, z+1; (iv) −x+1/2, y+1/2, −z−1/2; (v) −x+1, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₂N₂O₄S·2H₂O
M_r	398.47
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	273
a, b, c (Å)	21.690 (3), 11.4142 (17), 16.639 (2)
β (°)	112.459 (2)
V (Å³)	3806.9 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.19 × 0.16 × 0.06

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.962, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	9821, 3379, 2910
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.171, 1.05
No. of reflections	3379
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.41

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), 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···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···O1^iv	0.93	2.55	3.392 (3)	150
C7—H7B···O2ⁱ	0.96	2.44	3.325 (3)	154
C8—H8···O1^iv	0.93	2.43	3.353 (3)	172
C15—H15B···O3ⁱⁱ	0.97	2.50	3.444 (4)	166
C16—H16C···O5^v	0.96	2.51	3.42 (3)	160

Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) x+1/2, −y+1/2, z+1/2; (iii) x, y, z+1; (iv) −x+1/2, y+1/2, −z−1/2; (v) −x+1, y, −z+3/2.

Acknowledgements

The authors thank the Program for New Century Excellent Talents in Universities for a research grant.

References

Bruker (2000). 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. (1996). SADABS. University of Göttingen, Germany. 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 10| October 2009| Page o2339

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

4-(4-Di­ethyl­amino-2-hy­droxy­benzyl­­idene­ammonio)-3-methyl­benzene­sulfonate dihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-(4-Diethylamino-2-hydroxybenzylideneammonio)-3-methylbenzenesulfonate dihydrate