(E)-4-[4-(Diethyl-amino)-benzyl-idene-ammonio]-benzene-sulfonate.

The title compound, C(17)H(20)N(2)O(3)S, synthesised from sulfanilic acid and 4-diethyl-amino-benzaldehyde, crystallized out as a zwitterion with the central N atom protonated. The zwitterion exists in an E conformation with respect to the C=N double bond. The dihedral angle between the benzene rings is 37.57 (5)°. In the crystal, the zwitterions are linked into a tape along the a axis by N-H⋯O hydrogen bonds. The crystal structure is further stabilized by weak C-H⋯O inter-actions and π-π inter-actions with a centroid-centroid distance of 3.8541 (6) Å. An O⋯O [2.8498 (11) Å] short contact is present.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Banu & Golzar Hossain (2006 ▶); Yeap et al. (2010 ▶). For background and applications to sulfanilic acids, see: Chanawanno et al. (2010 ▶); Hussain et al. (2009 ▶); Kim et al. (2011 ▶); King (1991 ▶); Taylor et al. (2006 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C17H20N2O3S

M = 332.42

Triclinic,

a = 8.1227 (1) Å

b = 8.8745 (1) Å

c = 12.4070 (2) Å

α = 69.386 (1)°

β = 72.442 (1)°

γ = 75.509 (1)°

V = 787.63 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 100 K

0.45 × 0.22 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.906, T max = 0.969

24759 measured reflections

5685 independent reflections

5040 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.097

S = 1.04

5685 reflections

214 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.77 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026402/is5152sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026402/is5152Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026402/is5152Isup3.cml

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

C17H20N2O3S	Z = 2
Mr = 332.42	F(000) = 352
Triclinic, P1	Dx = 1.402 Mg m−3
Hall symbol: -P 1	Melting point = 540–541 K
a = 8.1227 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8745 (1) Å	Cell parameters from 5685 reflections
c = 12.4070 (2) Å	θ = 1.8–32.5°
α = 69.386 (1)°	µ = 0.22 mm−1
β = 72.442 (1)°	T = 100 K
γ = 75.509 (1)°	Block, yellow
V = 787.63 (2) Å3	0.45 × 0.22 × 0.14 mm

Bruker APEXII CCD area-detector diffractometer	5685 independent reflections
Radiation source: sealed tube	5040 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 32.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.906, Tmax = 0.969	k = −13→13
24759 measured reflections	l = −18→17

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0477P)2 + 0.3239P] where P = (Fo2 + 2Fc2)/3
5685 reflections	(Δ/σ)max = 0.001
214 parameters	Δρmax = 0.77 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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	−0.35313 (3)	0.23999 (3)	0.67776 (2)	0.01330 (6)
O1	−0.38256 (10)	0.25888 (10)	0.79395 (7)	0.02127 (16)
O2	−0.37965 (10)	0.08274 (9)	0.67967 (7)	0.01962 (15)
O3	−0.44670 (9)	0.37665 (9)	0.59896 (7)	0.01834 (14)
N1	0.39588 (10)	0.29545 (10)	0.43756 (8)	0.01497 (15)
N2	1.16999 (11)	0.27158 (11)	0.08368 (8)	0.01660 (16)
C1	0.12637 (12)	0.20179 (11)	0.45697 (8)	0.01394 (16)
H1A	0.1803	0.1600	0.3935	0.017*
C2	−0.04759 (12)	0.18925 (11)	0.51483 (8)	0.01344 (16)
H2A	−0.1106	0.1391	0.4898	0.016*
C3	−0.12775 (11)	0.25131 (11)	0.60985 (8)	0.01259 (15)
C4	−0.03462 (12)	0.32751 (12)	0.64768 (9)	0.01528 (17)
H4A	−0.0885	0.3685	0.7115	0.018*
C5	0.13909 (12)	0.34216 (12)	0.58977 (9)	0.01560 (17)
H5A	0.2013	0.3944	0.6138	0.019*
C6	0.21886 (11)	0.27794 (11)	0.49552 (8)	0.01322 (16)
C7	0.50414 (12)	0.19565 (11)	0.38086 (8)	0.01395 (16)
H7A	0.4650	0.1025	0.3867	0.017*
C8	0.67488 (12)	0.21763 (11)	0.31182 (8)	0.01355 (16)
C9	0.77809 (12)	0.09167 (12)	0.26404 (9)	0.01590 (17)
H9A	0.7332	−0.0032	0.2817	0.019*
C10	0.94259 (13)	0.10588 (12)	0.19236 (9)	0.01669 (17)
H10A	1.0086	0.0198	0.1640	0.020*
C11	1.01332 (12)	0.25146 (12)	0.16084 (8)	0.01427 (16)
C12	0.91019 (12)	0.37647 (12)	0.21180 (9)	0.01533 (17)
H12A	0.9551	0.4708	0.1956	0.018*
C13	0.74652 (12)	0.36035 (12)	0.28410 (9)	0.01506 (17)
H13A	0.6817	0.4442	0.3153	0.018*
C14	1.28157 (13)	0.14184 (13)	0.03449 (10)	0.02023 (19)
H14A	1.2715	0.0372	0.0948	0.024*
H14B	1.4026	0.1575	0.0128	0.024*
C15	1.23208 (15)	0.13989 (16)	−0.07380 (11)	0.0264 (2)
H15A	1.3078	0.0536	−0.1030	0.040*
H15B	1.2442	0.2425	−0.1343	0.040*
H15C	1.1130	0.1223	−0.0524	0.040*
C16	1.24190 (13)	0.42267 (13)	0.04692 (9)	0.01837 (18)
H16A	1.1470	0.5145	0.0429	0.022*
H16B	1.3185	0.4371	−0.0317	0.022*
C17	1.34381 (15)	0.42088 (16)	0.13212 (10)	0.0247 (2)
H17A	1.3825	0.5241	0.1080	0.037*
H17B	1.4434	0.3356	0.1314	0.037*
H17C	1.2698	0.4019	0.2107	0.037*
H1N1	0.427 (2)	0.380 (2)	0.4405 (14)	0.030 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.01089 (10)	0.01367 (10)	0.01646 (11)	−0.00400 (7)	−0.00018 (7)	−0.00702 (8)
O1	0.0193 (3)	0.0295 (4)	0.0174 (4)	−0.0095 (3)	0.0027 (3)	−0.0119 (3)
O2	0.0170 (3)	0.0154 (3)	0.0277 (4)	−0.0073 (2)	0.0013 (3)	−0.0102 (3)
O3	0.0130 (3)	0.0177 (3)	0.0254 (4)	−0.0014 (2)	−0.0054 (3)	−0.0078 (3)
N1	0.0111 (3)	0.0178 (4)	0.0183 (4)	−0.0050 (3)	−0.0009 (3)	−0.0085 (3)
N2	0.0127 (3)	0.0200 (4)	0.0166 (4)	−0.0038 (3)	0.0001 (3)	−0.0071 (3)
C1	0.0130 (4)	0.0163 (4)	0.0146 (4)	−0.0044 (3)	−0.0017 (3)	−0.0070 (3)
C2	0.0124 (3)	0.0145 (4)	0.0149 (4)	−0.0042 (3)	−0.0026 (3)	−0.0053 (3)
C3	0.0112 (3)	0.0126 (4)	0.0146 (4)	−0.0031 (3)	−0.0022 (3)	−0.0046 (3)
C4	0.0135 (4)	0.0174 (4)	0.0174 (4)	−0.0038 (3)	−0.0012 (3)	−0.0092 (3)
C5	0.0132 (4)	0.0181 (4)	0.0192 (4)	−0.0045 (3)	−0.0026 (3)	−0.0097 (3)
C6	0.0105 (3)	0.0143 (4)	0.0157 (4)	−0.0038 (3)	−0.0017 (3)	−0.0054 (3)
C7	0.0131 (4)	0.0155 (4)	0.0141 (4)	−0.0039 (3)	−0.0026 (3)	−0.0048 (3)
C8	0.0118 (3)	0.0156 (4)	0.0140 (4)	−0.0032 (3)	−0.0020 (3)	−0.0054 (3)
C9	0.0163 (4)	0.0147 (4)	0.0161 (4)	−0.0038 (3)	−0.0010 (3)	−0.0054 (3)
C10	0.0158 (4)	0.0155 (4)	0.0175 (4)	−0.0019 (3)	−0.0002 (3)	−0.0070 (3)
C11	0.0121 (4)	0.0169 (4)	0.0138 (4)	−0.0022 (3)	−0.0026 (3)	−0.0051 (3)
C12	0.0128 (4)	0.0160 (4)	0.0186 (4)	−0.0039 (3)	−0.0024 (3)	−0.0069 (3)
C13	0.0122 (4)	0.0162 (4)	0.0187 (4)	−0.0025 (3)	−0.0026 (3)	−0.0082 (3)
C14	0.0142 (4)	0.0241 (5)	0.0203 (5)	−0.0009 (3)	0.0008 (3)	−0.0098 (4)
C15	0.0235 (5)	0.0353 (6)	0.0236 (5)	−0.0071 (4)	0.0004 (4)	−0.0163 (5)
C16	0.0157 (4)	0.0231 (5)	0.0162 (4)	−0.0071 (3)	−0.0014 (3)	−0.0050 (4)
C17	0.0195 (4)	0.0374 (6)	0.0221 (5)	−0.0103 (4)	−0.0023 (4)	−0.0130 (4)

S1—O1	1.4511 (8)	C8—C9	1.4148 (13)
S1—O2	1.4555 (7)	C8—C13	1.4152 (13)
S1—O3	1.4685 (8)	C9—C10	1.3714 (13)
S1—C3	1.7814 (9)	C9—H9A	0.9300
N1—C7	1.3146 (12)	C10—C11	1.4256 (13)
N1—C6	1.4206 (11)	C10—H10A	0.9300
N1—H1N1	0.867 (17)	C11—C12	1.4288 (13)
N2—C11	1.3514 (12)	C12—C13	1.3704 (13)
N2—C16	1.4654 (13)	C12—H12A	0.9300
N2—C14	1.4692 (13)	C13—H13A	0.9300
C1—C2	1.3910 (12)	C14—C15	1.5207 (16)
C1—C6	1.3958 (13)	C14—H14A	0.9700
C1—H1A	0.9300	C14—H14B	0.9700
C2—C3	1.3897 (13)	C15—H15A	0.9600
C2—H2A	0.9300	C15—H15B	0.9600
C3—C4	1.3942 (12)	C15—H15C	0.9600
C4—C5	1.3923 (13)	C16—C17	1.5207 (15)
C4—H4A	0.9300	C16—H16A	0.9700
C5—C6	1.3926 (13)	C16—H16B	0.9700
C5—H5A	0.9300	C17—H17A	0.9600
C7—C8	1.4128 (12)	C17—H17B	0.9600
C7—H7A	0.9300	C17—H17C	0.9600
O1—S1—O2	114.51 (5)	C8—C9—H9A	119.2
O1—S1—O3	112.95 (5)	C9—C10—C11	120.59 (9)
O2—S1—O3	112.08 (5)	C9—C10—H10A	119.7
O1—S1—C3	105.86 (4)	C11—C10—H10A	119.7
O2—S1—C3	106.04 (4)	N2—C11—C10	121.17 (9)
O3—S1—C3	104.40 (4)	N2—C11—C12	121.43 (9)
C7—N1—C6	123.77 (8)	C10—C11—C12	117.38 (8)
C7—N1—H1N1	121.8 (11)	C13—C12—C11	121.44 (8)
C6—N1—H1N1	114.4 (11)	C13—C12—H12A	119.3
C11—N2—C16	121.95 (8)	C11—C12—H12A	119.3
C11—N2—C14	122.25 (8)	C12—C13—C8	120.79 (9)
C16—N2—C14	115.76 (8)	C12—C13—H13A	119.6
C2—C1—C6	119.04 (9)	C8—C13—H13A	119.6
C2—C1—H1A	120.5	N2—C14—C15	112.15 (9)
C6—C1—H1A	120.5	N2—C14—H14A	109.2
C3—C2—C1	120.39 (8)	C15—C14—H14A	109.2
C3—C2—H2A	119.8	N2—C14—H14B	109.2
C1—C2—H2A	119.8	C15—C14—H14B	109.2
C2—C3—C4	120.24 (8)	H14A—C14—H14B	107.9
C2—C3—S1	118.97 (7)	C14—C15—H15A	109.5
C4—C3—S1	120.73 (7)	C14—C15—H15B	109.5
C5—C4—C3	119.90 (9)	H15A—C15—H15B	109.5
C5—C4—H4A	120.0	C14—C15—H15C	109.5
C3—C4—H4A	120.0	H15A—C15—H15C	109.5
C4—C5—C6	119.43 (8)	H15B—C15—H15C	109.5
C4—C5—H5A	120.3	N2—C16—C17	111.85 (9)
C6—C5—H5A	120.3	N2—C16—H16A	109.2
C5—C6—C1	121.00 (8)	C17—C16—H16A	109.2
C5—C6—N1	118.26 (8)	N2—C16—H16B	109.2
C1—C6—N1	120.73 (8)	C17—C16—H16B	109.2
N1—C7—C8	125.64 (8)	H16A—C16—H16B	107.9
N1—C7—H7A	117.2	C16—C17—H17A	109.5
C8—C7—H7A	117.2	C16—C17—H17B	109.5
C7—C8—C9	117.96 (8)	H17A—C17—H17B	109.5
C7—C8—C13	123.96 (8)	C16—C17—H17C	109.5
C9—C8—C13	118.04 (8)	H17A—C17—H17C	109.5
C10—C9—C8	121.68 (9)	H17B—C17—H17C	109.5
C10—C9—H9A	119.2
C6—C1—C2—C3	−0.18 (14)	N1—C7—C8—C13	−6.89 (16)
C1—C2—C3—C4	0.32 (14)	C7—C8—C9—C10	177.47 (9)
C1—C2—C3—S1	177.54 (7)	C13—C8—C9—C10	−0.33 (15)
O1—S1—C3—C2	160.63 (8)	C8—C9—C10—C11	−1.77 (15)
O2—S1—C3—C2	38.60 (9)	C16—N2—C11—C10	177.74 (9)
O3—S1—C3—C2	−79.93 (8)	C14—N2—C11—C10	−4.37 (15)
O1—S1—C3—C4	−22.17 (9)	C16—N2—C11—C12	−0.73 (15)
O2—S1—C3—C4	−144.20 (8)	C14—N2—C11—C12	177.16 (9)
O3—S1—C3—C4	97.27 (8)	C9—C10—C11—N2	−175.28 (10)
C2—C3—C4—C5	0.28 (14)	C9—C10—C11—C12	3.24 (14)
S1—C3—C4—C5	−176.89 (7)	N2—C11—C12—C13	175.78 (9)
C3—C4—C5—C6	−1.00 (15)	C10—C11—C12—C13	−2.75 (14)
C4—C5—C6—C1	1.15 (15)	C11—C12—C13—C8	0.74 (15)
C4—C5—C6—N1	179.62 (9)	C7—C8—C13—C12	−176.80 (9)
C2—C1—C6—C5	−0.56 (14)	C9—C8—C13—C12	0.85 (14)
C2—C1—C6—N1	−178.99 (8)	C11—N2—C14—C15	84.88 (12)
C7—N1—C6—C5	153.95 (10)	C16—N2—C14—C15	−97.11 (11)
C7—N1—C6—C1	−27.57 (14)	C11—N2—C16—C17	86.61 (12)
C6—N1—C7—C8	172.99 (9)	C14—N2—C16—C17	−91.41 (11)
N1—C7—C8—C9	175.46 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3i	0.865 (18)	2.466 (17)	3.0309 (12)	123.6 (13)
N1—H1N1···O3ii	0.865 (18)	2.076 (18)	2.8989 (12)	158.7 (16)
C7—H7A···O2iii	0.93	2.39	3.2719 (13)	157
C13—H13A···O3ii	0.93	2.40	3.3002 (13)	164
C14—H14A···O1iv	0.97	2.58	3.4805 (14)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O3i	0.865 (18)	2.466 (17)	3.0309 (12)	123.6 (13)
N1—H1N1⋯O3ii	0.865 (18)	2.076 (18)	2.8989 (12)	158.7 (16)
C7—H7A⋯O2iii	0.93	2.39	3.2719 (13)	157
C13—H13A⋯O3ii	0.93	2.40	3.3002 (13)	164
C14—H14A⋯O1iv	0.97	2.58	3.4805 (14)	155

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