2-[(E)-2-(4-Methyl-benzene-sulfonamido)ethyl-iminiometh-yl]-4-nitro-phenolate.

The mol-ecule of the title compound, C(16)H(17)N(3)O(5)S, crystallizes in a zwitterionic form, with a strong intra-molecular N-H⋯O hydrogen bond. The dihedral angle between the two benzene rings is 7.06 (9)°. In the crystal, mol-ecules are linked into chains along the c axis by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For general background to Schiff bases, see: Calligaris et al. (1972 ▶); Cohen et al. (1964 ▶); Hadjoudis et al. (1987 ▶); Karabıyık et al. (2008 ▶). For the crystal structure of 2-[2-(1H-indol-3-yl)ethyl­iminiometh­yl]-4-nitro­phenolate, see: Ali et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H17N3O5S

M = 363.39

Monoclinic,

a = 17.915 (5) Å

b = 7.342 (5) Å

c = 13.055 (5) Å

β = 103.928 (5)°

V = 1666.7 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.68 × 0.50 × 0.26 mm

Data collection

Stoe IPDS-II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.887, T max = 0.956

22908 measured reflections

3272 independent reflections

2845 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.094

S = 1.07

3272 reflections

236 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.27 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809031481/ci2882sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031481/ci2882Isup2.hkl

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

C16H17N3O5S	F(000) = 760
Mr = 363.39	Dx = 1.448 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 37649 reflections
a = 17.915 (5) Å	θ = 1.6–28.0°
b = 7.342 (5) Å	µ = 0.23 mm−1
c = 13.055 (5) Å	T = 296 K
β = 103.928 (5)°	Block, yellow
V = 1666.7 (14) Å3	0.68 × 0.50 × 0.26 mm
Z = 4

Stoe IPDS-II diffractometer	3272 independent reflections
Radiation source: fine-focus sealed tube	2845 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 2.3°
ω scans	h = −22→22
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.887, Tmax = 0.956	l = −16→15
22908 measured reflections

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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0542P)2 + 0.2378P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.004
3272 reflections	Δρmax = 0.26 e Å−3
236 parameters	Δρmin = −0.27 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: 0.0025 (8)

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
C1	0.73857 (9)	0.1439 (2)	0.58535 (12)	0.0464 (3)
C2	0.81399 (10)	0.1345 (2)	0.64584 (14)	0.0559 (4)
H2	0.8238	0.1405	0.7190	0.067*
C3	0.87338 (10)	0.1163 (3)	0.59823 (15)	0.0604 (4)
C4	0.86008 (11)	0.1075 (3)	0.48830 (16)	0.0648 (5)
H4	0.9012	0.0958	0.4567	0.078*
C5	0.78743 (11)	0.1160 (3)	0.42812 (15)	0.0642 (5)
H5	0.7796	0.1093	0.3552	0.077*
C6	0.72214 (10)	0.1346 (2)	0.47198 (13)	0.0523 (4)
C7	0.67882 (9)	0.1617 (2)	0.63841 (13)	0.0463 (3)
H7	0.6925	0.1648	0.7118	0.056*
C8	0.54749 (9)	0.1973 (2)	0.65034 (13)	0.0466 (4)
H8A	0.5661	0.1505	0.7214	0.056*
H8B	0.5024	0.1275	0.6162	0.056*
C9	0.52559 (8)	0.3947 (2)	0.65549 (12)	0.0438 (3)
H9A	0.5085	0.4419	0.5843	0.053*
H9B	0.4829	0.4035	0.6889	0.053*
C10	0.69671 (8)	0.65737 (19)	0.62312 (11)	0.0400 (3)
C11	0.69016 (9)	0.6244 (2)	0.51721 (12)	0.0495 (4)
H11	0.6420	0.6182	0.4705	0.059*
C12	0.75608 (10)	0.6008 (3)	0.48147 (13)	0.0571 (4)
H12	0.7515	0.5781	0.4102	0.068*
C13	0.82838 (10)	0.6100 (2)	0.54833 (15)	0.0553 (4)
C14	0.83365 (10)	0.6421 (3)	0.65479 (15)	0.0601 (4)
H14	0.8818	0.6474	0.7015	0.072*
C15	0.76879 (9)	0.6661 (2)	0.69225 (13)	0.0522 (4)
H15	0.7733	0.6882	0.7636	0.063*
C16	0.89969 (12)	0.5917 (3)	0.50703 (19)	0.0795 (6)
H16A	0.8863	0.5403	0.4374	0.119*
H16B	0.9359	0.5136	0.5529	0.119*
H16C	0.9223	0.7097	0.5045	0.119*
N1	0.95110 (10)	0.1062 (3)	0.66326 (18)	0.0917 (6)
N2	0.60663 (7)	0.17413 (18)	0.59235 (11)	0.0456 (3)
N3	0.58876 (7)	0.50612 (18)	0.71366 (10)	0.0448 (3)
O1	0.96069 (10)	0.1084 (5)	0.75840 (16)	0.1571 (12)
O2	1.00420 (9)	0.0954 (4)	0.62016 (16)	0.1183 (7)
O3	0.65360 (7)	0.1427 (2)	0.41569 (9)	0.0669 (4)
O4	0.55334 (6)	0.75149 (15)	0.58460 (9)	0.0479 (3)
O5	0.63776 (6)	0.81294 (15)	0.76080 (9)	0.0522 (3)
S1	0.614192 (19)	0.69488 (5)	0.67146 (3)	0.03887 (13)
H1	0.6088 (10)	0.478 (2)	0.7710 (14)	0.048 (5)*
H1A	0.5970 (12)	0.176 (3)	0.5235 (17)	0.067 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0470 (8)	0.0456 (8)	0.0471 (8)	−0.0002 (6)	0.0121 (7)	−0.0028 (7)
C2	0.0522 (9)	0.0660 (10)	0.0494 (9)	−0.0005 (8)	0.0124 (7)	0.0003 (8)
C3	0.0452 (9)	0.0709 (11)	0.0658 (11)	0.0025 (8)	0.0148 (8)	0.0017 (9)
C4	0.0601 (11)	0.0720 (12)	0.0701 (12)	0.0056 (9)	0.0307 (9)	−0.0012 (10)
C5	0.0709 (12)	0.0753 (12)	0.0507 (9)	0.0086 (10)	0.0232 (9)	−0.0062 (9)
C6	0.0568 (10)	0.0516 (9)	0.0487 (9)	0.0038 (7)	0.0130 (7)	−0.0072 (7)
C7	0.0505 (9)	0.0449 (8)	0.0432 (8)	−0.0021 (6)	0.0107 (7)	−0.0007 (6)
C8	0.0438 (8)	0.0475 (8)	0.0502 (9)	−0.0058 (6)	0.0147 (7)	0.0030 (7)
C9	0.0348 (7)	0.0498 (8)	0.0472 (8)	−0.0037 (6)	0.0109 (6)	0.0008 (7)
C10	0.0389 (7)	0.0409 (7)	0.0399 (7)	−0.0016 (6)	0.0089 (6)	0.0033 (6)
C11	0.0425 (8)	0.0643 (10)	0.0407 (8)	−0.0008 (7)	0.0079 (6)	0.0049 (7)
C12	0.0556 (10)	0.0750 (12)	0.0440 (9)	0.0037 (8)	0.0185 (7)	0.0086 (8)
C13	0.0469 (9)	0.0583 (10)	0.0651 (11)	0.0003 (7)	0.0222 (8)	0.0094 (8)
C14	0.0378 (8)	0.0749 (12)	0.0637 (11)	−0.0013 (8)	0.0044 (7)	0.0005 (9)
C15	0.0444 (8)	0.0643 (10)	0.0450 (8)	0.0001 (7)	0.0054 (7)	−0.0027 (7)
C16	0.0553 (11)	0.0987 (16)	0.0943 (15)	0.0034 (11)	0.0372 (11)	0.0117 (13)
N1	0.0490 (9)	0.1412 (19)	0.0847 (13)	0.0029 (11)	0.0154 (9)	0.0064 (13)
N2	0.0471 (7)	0.0463 (7)	0.0444 (7)	−0.0015 (5)	0.0131 (6)	−0.0026 (6)
N3	0.0466 (7)	0.0521 (8)	0.0328 (7)	−0.0071 (6)	0.0041 (5)	0.0045 (6)
O1	0.0575 (10)	0.327 (4)	0.0791 (12)	0.0105 (15)	0.0021 (9)	0.0096 (18)
O2	0.0494 (8)	0.195 (2)	0.1165 (14)	0.0089 (11)	0.0310 (9)	−0.0005 (14)
O3	0.0600 (8)	0.0888 (9)	0.0472 (7)	0.0093 (7)	0.0038 (6)	−0.0159 (6)
O4	0.0417 (5)	0.0488 (6)	0.0494 (6)	0.0043 (4)	0.0034 (5)	0.0055 (5)
O5	0.0512 (6)	0.0543 (6)	0.0504 (6)	−0.0036 (5)	0.0108 (5)	−0.0159 (5)
S1	0.03696 (19)	0.0403 (2)	0.0382 (2)	0.00009 (14)	0.00693 (14)	−0.00238 (14)

C1—C2	1.393 (2)	C10—C15	1.387 (2)
C1—C7	1.414 (2)	C10—S1	1.7631 (15)
C1—C6	1.440 (2)	C11—C12	1.381 (2)
C2—C3	1.362 (2)	C11—H11	0.93
C2—H2	0.93	C12—C13	1.378 (3)
C3—C4	1.399 (3)	C12—H12	0.93
C3—N1	1.448 (3)	C13—C14	1.390 (3)
C4—C5	1.350 (3)	C13—C16	1.507 (2)
C4—H4	0.93	C14—C15	1.376 (2)
C5—C6	1.427 (2)	C14—H14	0.93
C5—H5	0.93	C15—H15	0.93
C6—O3	1.272 (2)	C16—H16A	0.96
C7—N2	1.292 (2)	C16—H16B	0.96
C7—H7	0.93	C16—H16C	0.96
C8—N2	1.4529 (19)	N1—O1	1.212 (3)
C8—C9	1.507 (2)	N1—O2	1.219 (2)
C8—H8A	0.97	N2—H1A	0.87 (2)
C8—H8B	0.97	N3—S1	1.5976 (16)
C9—N3	1.4537 (19)	N3—H1	0.777 (18)
C9—H9A	0.97	O4—S1	1.4325 (11)
C9—H9B	0.97	O5—S1	1.4329 (12)
C10—C11	1.381 (2)
C2—C1—C7	118.18 (15)	C10—C11—C12	119.13 (15)
C2—C1—C6	120.72 (15)	C10—C11—H11	120.4
C7—C1—C6	121.10 (15)	C12—C11—H11	120.4
C3—C2—C1	120.26 (16)	C13—C12—C11	121.97 (16)
C3—C2—H2	119.9	C13—C12—H12	119.0
C1—C2—H2	119.9	C11—C12—H12	119.0
C2—C3—C4	120.93 (17)	C12—C13—C14	117.95 (15)
C2—C3—N1	118.96 (18)	C12—C13—C16	121.15 (18)
C4—C3—N1	120.11 (17)	C14—C13—C16	120.87 (17)
C5—C4—C3	119.81 (16)	C15—C14—C13	121.12 (16)
C5—C4—H4	120.1	C15—C14—H14	119.4
C3—C4—H4	120.1	C13—C14—H14	119.4
C4—C5—C6	122.64 (17)	C14—C15—C10	119.75 (16)
C4—C5—H5	118.7	C14—C15—H15	120.1
C6—C5—H5	118.7	C10—C15—H15	120.1
O3—C6—C5	122.91 (16)	C13—C16—H16A	109.5
O3—C6—C1	121.46 (15)	C13—C16—H16B	109.5
C5—C6—C1	115.63 (16)	H16A—C16—H16B	109.5
N2—C7—C1	124.73 (15)	C13—C16—H16C	109.5
N2—C7—H7	117.6	H16A—C16—H16C	109.5
C1—C7—H7	117.6	H16B—C16—H16C	109.5
N2—C8—C9	111.47 (12)	O1—N1—O2	122.7 (2)
N2—C8—H8A	109.3	O1—N1—C3	118.65 (18)
C9—C8—H8A	109.3	O2—N1—C3	118.7 (2)
N2—C8—H8B	109.3	C7—N2—C8	122.67 (14)
C9—C8—H8B	109.3	C7—N2—H1A	114.1 (14)
H8A—C8—H8B	108.0	C8—N2—H1A	123.0 (14)
N3—C9—C8	112.72 (13)	C9—N3—S1	123.98 (11)
N3—C9—H9A	109.0	C9—N3—H1	118.3 (13)
C8—C9—H9A	109.0	S1—N3—H1	117.4 (13)
N3—C9—H9B	109.0	O4—S1—O5	119.20 (8)
C8—C9—H9B	109.0	O4—S1—N3	107.39 (7)
H9A—C9—H9B	107.8	O5—S1—N3	107.26 (8)
C11—C10—C15	120.07 (14)	O4—S1—C10	107.82 (7)
C11—C10—S1	120.62 (11)	O5—S1—C10	106.12 (7)
C15—C10—S1	119.29 (12)	N3—S1—C10	108.74 (7)
C7—C1—C2—C3	179.67 (16)	C12—C13—C14—C15	−0.7 (3)
C6—C1—C2—C3	0.0 (3)	C16—C13—C14—C15	177.35 (18)
C1—C2—C3—C4	0.2 (3)	C13—C14—C15—C10	0.3 (3)
C1—C2—C3—N1	−179.76 (18)	C11—C10—C15—C14	0.1 (3)
C2—C3—C4—C5	−0.4 (3)	S1—C10—C15—C14	−178.20 (13)
N1—C3—C4—C5	179.6 (2)	C2—C3—N1—O1	2.3 (4)
C3—C4—C5—C6	0.3 (3)	C4—C3—N1—O1	−177.7 (3)
C4—C5—C6—O3	180.00 (19)	C2—C3—N1—O2	−177.8 (2)
C4—C5—C6—C1	0.0 (3)	C4—C3—N1—O2	2.2 (4)
C2—C1—C6—O3	179.83 (16)	C1—C7—N2—C8	−178.27 (14)
C7—C1—C6—O3	0.2 (3)	C9—C8—N2—C7	96.71 (17)
C2—C1—C6—C5	−0.1 (2)	C8—C9—N3—S1	131.22 (13)
C7—C1—C6—C5	−179.75 (16)	C9—N3—S1—O4	14.65 (14)
C2—C1—C7—N2	179.17 (15)	C9—N3—S1—O5	143.88 (12)
C6—C1—C7—N2	−1.2 (3)	C9—N3—S1—C10	−101.76 (13)
N2—C8—C9—N3	−63.94 (17)	C11—C10—S1—O4	−21.41 (15)
C15—C10—C11—C12	−0.1 (2)	C15—C10—S1—O4	156.87 (13)
S1—C10—C11—C12	178.14 (13)	C11—C10—S1—O5	−150.18 (13)
C10—C11—C12—C13	−0.3 (3)	C15—C10—S1—O5	28.09 (15)
C11—C12—C13—C14	0.7 (3)	C11—C10—S1—N3	94.72 (14)
C11—C12—C13—C16	−177.38 (18)	C15—C10—S1—N3	−87.00 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O3i	0.78 (2)	2.06 (2)	2.833 (2)	170 (2)
N2—H1A···O3	0.87 (2)	1.94 (2)	2.648 (2)	137 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯O3i	0.78 (2)	2.06 (2)	2.833 (2)	170 (2)
N2—H1A⋯O3	0.87 (2)	1.94 (2)	2.648 (2)	137 (2)

Symmetry code: (i) .