4-Methyl-anilinium 4-hy-droxy-benzene-sulfonate.

In the crystal of the title molecular salt, C7H10N(+)·C6H5O4S(-), the benzene-sulfonate units are linked through phenol-sulfonate O-H⋯O hydrogen bonds, forming chains along the c-axis direction. These chains are linked via N-H⋯O hydrogen bonds involving two of the three H atoms of the ammonium group of the 4-methyl-anilium cation, giving rise to two-dimensional networks parallel to the bc plane which are further connected through an additional N-H⋯O inter-action in which the third ammonium H atom is involved, generating a three-dimensional network.

Related literature

For the biological activity of related compounds, see: Fukami et al. (2000 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C7H10N+·C6H5O4S−

M = 281.32

Monoclinic,

a = 11.6450 (2) Å

b = 7.1670 (1) Å

c = 16.3080 (3) Å

β = 107.654 (1)°

V = 1296.96 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.926, T max = 0.950

11047 measured reflections

2285 independent reflections

2045 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.091

S = 1.06

2285 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813009410/lr2102sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009410/lr2102Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009410/lr2102Isup3.cml

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

C7H10N+·C6H5O4S−	F(000) = 592
Mr = 281.32	Dx = 1.441 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5614 reflections
a = 11.6450 (2) Å	θ = 2.8–29.4°
b = 7.1670 (1) Å	µ = 0.26 mm−1
c = 16.3080 (3) Å	T = 293 K
β = 107.654 (1)°	Block, colourless
V = 1296.96 (4) Å3	0.30 × 0.30 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2285 independent reflections
Radiation source: fine-focus sealed tube	2045 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω and φ scan	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→13
Tmin = 0.926, Tmax = 0.950	k = −8→8
11047 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)] = 0.030	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0467P)2 + 0.4532P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2285 reflections	Δρmax = 0.24 e Å−3
175 parameters	Δρmin = −0.29 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: 0.0070 (12)

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	0.65813 (14)	0.2000 (2)	0.30612 (10)	0.0311 (4)
C2	0.54731 (14)	0.1192 (2)	0.26762 (10)	0.0375 (4)
H2	0.5057	0.0616	0.3011	0.045*
C3	0.49842 (14)	0.1242 (2)	0.17924 (10)	0.0391 (4)
H3	0.4240	0.0688	0.1532	0.047*
C4	0.55951 (14)	0.2109 (2)	0.12920 (10)	0.0328 (4)
C5	0.67033 (15)	0.2933 (2)	0.16791 (11)	0.0365 (4)
H5	0.7116	0.3521	0.1345	0.044*
C6	0.71913 (14)	0.2878 (2)	0.25594 (10)	0.0355 (4)
H6	0.7935	0.3432	0.2820	0.043*
C7	0.91246 (16)	−0.3025 (2)	0.27651 (11)	0.0420 (4)
C8	0.79646 (16)	−0.2324 (3)	0.24420 (12)	0.0455 (4)
H8	0.7542	−0.2001	0.2822	0.055*
C9	0.74260 (15)	−0.2096 (2)	0.15731 (12)	0.0423 (4)
H9	0.6646	−0.1628	0.1367	0.051*
C10	0.80527 (14)	−0.2568 (2)	0.10108 (11)	0.0353 (4)
C11	0.92034 (15)	−0.3268 (2)	0.13049 (12)	0.0432 (4)
H11	0.9623	−0.3581	0.0922	0.052*
C12	0.97244 (15)	−0.3499 (3)	0.21799 (12)	0.0450 (4)
H12	1.0500	−0.3986	0.2382	0.054*
C13	0.9715 (2)	−0.3262 (3)	0.37143 (13)	0.0614 (6)
H13A	0.9581	−0.2166	0.4011	0.092*
H13B	1.0565	−0.3446	0.3825	0.092*
H13C	0.9377	−0.4327	0.3914	0.092*
N1	0.74899 (13)	−0.2321 (2)	0.00829 (9)	0.0424 (4)
H1A	0.7692	−0.1211	−0.0076	0.064*
H1B	0.6692	−0.2387	−0.0039	0.064*
H1C	0.7743	−0.3214	−0.0200	0.064*
O1	0.82148 (11)	0.05029 (17)	0.43307 (7)	0.0458 (3)
O2	0.77002 (13)	0.37156 (18)	0.44678 (8)	0.0559 (4)
O3	0.63246 (11)	0.1221 (2)	0.45415 (8)	0.0526 (4)
O4	0.50641 (11)	0.21139 (18)	0.04252 (7)	0.0450 (3)
H4	0.5499	0.2661	0.0192	0.068*
S1	0.72587 (4)	0.18720 (6)	0.41863 (2)	0.03519 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0357 (8)	0.0251 (8)	0.0341 (8)	0.0030 (6)	0.0128 (7)	−0.0003 (6)
C2	0.0401 (9)	0.0344 (9)	0.0402 (9)	−0.0053 (7)	0.0156 (7)	0.0051 (7)
C3	0.0354 (8)	0.0381 (9)	0.0416 (9)	−0.0091 (7)	0.0084 (7)	0.0018 (7)
C4	0.0377 (8)	0.0283 (8)	0.0332 (8)	0.0027 (6)	0.0119 (7)	−0.0009 (6)
C5	0.0384 (9)	0.0356 (9)	0.0404 (9)	−0.0032 (7)	0.0193 (7)	0.0013 (7)
C6	0.0329 (8)	0.0336 (9)	0.0405 (9)	−0.0048 (7)	0.0119 (7)	−0.0026 (7)
C7	0.0459 (9)	0.0283 (9)	0.0484 (10)	−0.0016 (7)	0.0093 (8)	−0.0028 (7)
C8	0.0492 (10)	0.0398 (10)	0.0502 (10)	0.0040 (8)	0.0192 (8)	−0.0065 (8)
C9	0.0358 (9)	0.0345 (9)	0.0548 (11)	0.0065 (7)	0.0108 (8)	−0.0039 (8)
C10	0.0376 (8)	0.0243 (8)	0.0429 (9)	−0.0023 (7)	0.0105 (7)	−0.0014 (7)
C11	0.0404 (9)	0.0381 (9)	0.0542 (11)	0.0022 (7)	0.0191 (8)	−0.0033 (8)
C12	0.0349 (9)	0.0372 (9)	0.0589 (11)	0.0045 (7)	0.0079 (8)	0.0003 (8)
C13	0.0728 (14)	0.0525 (12)	0.0495 (12)	0.0006 (10)	0.0045 (10)	−0.0017 (9)
N1	0.0475 (8)	0.0328 (8)	0.0455 (8)	−0.0036 (6)	0.0119 (7)	0.0014 (6)
O1	0.0507 (7)	0.0420 (7)	0.0437 (7)	0.0128 (6)	0.0126 (5)	0.0063 (5)
O2	0.0760 (9)	0.0356 (7)	0.0452 (7)	−0.0002 (7)	0.0020 (6)	−0.0077 (6)
O3	0.0587 (8)	0.0666 (9)	0.0394 (7)	0.0015 (7)	0.0252 (6)	0.0000 (6)
O4	0.0464 (7)	0.0555 (8)	0.0325 (6)	−0.0069 (6)	0.0110 (5)	−0.0001 (5)
S1	0.0436 (3)	0.0304 (2)	0.0315 (2)	0.00412 (16)	0.01122 (17)	−0.00084 (15)

C1—C2	1.380 (2)	C9—C10	1.376 (2)
C1—C6	1.386 (2)	C9—H9	0.9300
C1—S1	1.7662 (16)	C10—C11	1.374 (2)
C2—C3	1.380 (2)	C10—N1	1.466 (2)
C2—H2	0.9300	C11—C12	1.381 (3)
C3—C4	1.382 (2)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
C4—O4	1.3603 (19)	C13—H13A	0.9600
C4—C5	1.385 (2)	C13—H13B	0.9600
C5—C6	1.375 (2)	C13—H13C	0.9600
C5—H5	0.9300	N1—H1A	0.8900
C6—H6	0.9300	N1—H1B	0.8900
C7—C12	1.385 (3)	N1—H1C	0.8900
C7—C8	1.387 (2)	O1—S1	1.4487 (12)
C7—C13	1.501 (3)	O2—S1	1.4414 (13)
C8—C9	1.374 (3)	O3—S1	1.4556 (13)
C8—H8	0.9300	O4—H4	0.8200
C2—C1—C6	119.85 (15)	C11—C10—N1	119.19 (15)
C2—C1—S1	120.82 (12)	C9—C10—N1	119.79 (15)
C6—C1—S1	119.30 (12)	C10—C11—C12	118.74 (16)
C1—C2—C3	119.81 (15)	C10—C11—H11	120.6
C1—C2—H2	120.1	C12—C11—H11	120.6
C3—C2—H2	120.1	C11—C12—C7	121.83 (16)
C2—C3—C4	120.32 (15)	C11—C12—H12	119.1
C2—C3—H3	119.8	C7—C12—H12	119.1
C4—C3—H3	119.8	C7—C13—H13A	109.5
O4—C4—C3	117.48 (14)	C7—C13—H13B	109.5
O4—C4—C5	122.66 (14)	H13A—C13—H13B	109.5
C3—C4—C5	119.85 (15)	C7—C13—H13C	109.5
C6—C5—C4	119.78 (15)	H13A—C13—H13C	109.5
C6—C5—H5	120.1	H13B—C13—H13C	109.5
C4—C5—H5	120.1	C10—N1—H1A	109.5
C5—C6—C1	120.38 (14)	C10—N1—H1B	109.5
C5—C6—H6	119.8	H1A—N1—H1B	109.5
C1—C6—H6	119.8	C10—N1—H1C	109.5
C12—C7—C8	117.63 (17)	H1A—N1—H1C	109.5
C12—C7—C13	120.91 (17)	H1B—N1—H1C	109.5
C8—C7—C13	121.46 (17)	C4—O4—H4	109.5
C9—C8—C7	121.47 (17)	O2—S1—O1	112.76 (8)
C9—C8—H8	119.3	O2—S1—O3	113.86 (8)
C7—C8—H8	119.3	O1—S1—O3	110.38 (8)
C8—C9—C10	119.31 (16)	O2—S1—C1	106.67 (7)
C8—C9—H9	120.3	O1—S1—C1	106.46 (7)
C10—C9—H9	120.3	O3—S1—C1	106.13 (7)
C11—C10—C9	121.02 (16)
C6—C1—C2—C3	0.8 (2)	C8—C9—C10—C11	0.3 (3)
S1—C1—C2—C3	−177.26 (13)	C8—C9—C10—N1	−179.65 (15)
C1—C2—C3—C4	−0.5 (2)	C9—C10—C11—C12	0.2 (3)
C2—C3—C4—O4	−179.85 (15)	N1—C10—C11—C12	−179.88 (15)
C2—C3—C4—C5	0.0 (2)	C10—C11—C12—C7	−0.7 (3)
O4—C4—C5—C6	−179.95 (14)	C8—C7—C12—C11	0.8 (3)
C3—C4—C5—C6	0.2 (2)	C13—C7—C12—C11	−179.14 (17)
C4—C5—C6—C1	0.1 (2)	C2—C1—S1—O2	−134.51 (14)
C2—C1—C6—C5	−0.6 (2)	C6—C1—S1—O2	47.42 (14)
S1—C1—C6—C5	177.49 (12)	C2—C1—S1—O1	104.85 (14)
C12—C7—C8—C9	−0.3 (3)	C6—C1—S1—O1	−73.21 (14)
C13—C7—C8—C9	179.63 (17)	C2—C1—S1—O3	−12.76 (15)
C7—C8—C9—C10	−0.2 (3)	C6—C1—S1—O3	169.17 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1i	0.89	1.96	2.8367 (19)	169
N1—H1B···O4ii	0.89	1.96	2.839 (2)	170
N1—H1A···O2iii	0.89	1.94	2.8091 (19)	166
O4—H4···O3iii	0.82	1.82	2.6343 (17)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O1i	0.89	1.96	2.8367 (19)	169
N1—H1B⋯O4ii	0.89	1.96	2.839 (2)	170
N1—H1A⋯O2iii	0.89	1.94	2.8091 (19)	166
O4—H4⋯O3iii	0.82	1.82	2.6343 (17)	173

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