N-(2-Hy-droxy-benz-yl)adamantan-1-aminium 4-methyl-benzene-sulfonate.

In the crystal structure of the title salt, C(17)H(24)NO(+)·C(7)H(7)O(3)S(-), the N-(2-hy-droxy-benz-yl)adamantan-1-aminium cations and 4-methyl-benzene-sulfonate anions are linked by O-H⋯O and N-H⋯O hydrogen bonds. C-H⋯π inter-actions are also observed between the cation and the anion.

Related literature

For related compounds, see: Blagden et al. (2008 ▶); Vishweshwar et al. (2006 ▶); Kapildev et al. (2011 ▶); Schultheiss & Newman (2009 ▶).

Experimental

Crystal data

C17H24NO+·C7H7O3S−

M = 429.57

Triclinic,

a = 10.159 (2) Å

b = 10.413 (2) Å

c = 11.270 (2) Å

α = 79.03 (3)°

β = 69.06 (3)°

γ = 78.49 (3)°

V = 1081.8 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 298 K

0.30 × 0.25 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.90, T max = 0.99

11276 measured reflections

4940 independent reflections

3641 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.157

S = 1.08

4940 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.37 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811048860/xu5389sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048860/xu5389Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048860/xu5389Isup3.cml

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

C17H24NO+·C7H7O3S−	Z = 2
Mr = 429.57	F(000) = 460
Triclinic, P1	Dx = 1.319 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.159 (2) Å	Cell parameters from 4940 reflections
b = 10.413 (2) Å	θ = 3.2–27.5°
c = 11.270 (2) Å	µ = 0.18 mm−1
α = 79.03 (3)°	T = 298 K
β = 69.06 (3)°	Block, colorless
γ = 78.49 (3)°	0.30 × 0.25 × 0.15 mm
V = 1081.8 (4) Å3

Rigaku Mercury2 diffractometer	4940 independent reflections
Radiation source: fine-focus sealed tube	3641 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.2°
CCD profile fitting scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
Tmin = 0.90, Tmax = 0.99	l = −14→14
11276 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0745P)2 + 0.0901P] where P = (Fo2 + 2Fc2)/3
4940 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.29772 (5)	0.18203 (5)	−0.09359 (5)	0.03453 (17)
O1	0.3379 (2)	0.27308 (18)	−0.20841 (17)	0.0687 (6)
O2	0.21525 (15)	0.08446 (15)	−0.10027 (16)	0.0436 (4)
O3	0.41568 (16)	0.11518 (16)	−0.05151 (17)	0.0505 (4)
C18	0.1835 (2)	0.2733 (2)	0.0305 (2)	0.0327 (5)
C19	0.1698 (2)	0.4098 (2)	0.0133 (2)	0.0403 (5)
H19A	0.2168	0.4545	−0.0658	0.039 (6)*
C20	0.0866 (3)	0.4795 (2)	0.1134 (3)	0.0477 (6)
H20A	0.0786	0.5712	0.1011	0.049 (7)*
C21	0.0147 (3)	0.4160 (2)	0.2312 (3)	0.0496 (6)
C22	0.0275 (3)	0.2787 (3)	0.2467 (3)	0.0536 (6)
H22A	−0.0212	0.2340	0.3252	0.053 (7)*
C23	0.1107 (3)	0.2083 (2)	0.1477 (2)	0.0455 (6)
H23A	0.1182	0.1166	0.1596	0.052 (7)*
C24	−0.0759 (4)	0.4946 (4)	0.3410 (4)	0.0796 (10)
H24A	−0.1174	0.4350	0.4155	0.107 (14)*
H24B	−0.1503	0.5540	0.3170	0.154 (19)*
H24C	−0.0173	0.5443	0.3597	0.107 (13)*
O4	0.93542 (15)	0.17176 (15)	−0.06761 (14)	0.0415 (4)
H4A	1.0199	0.1458	−0.0778	0.062*
N1	0.61227 (17)	0.16841 (15)	0.05577 (15)	0.0299 (4)
H1A	0.6871	0.1067	0.0593	0.045*
H1B	0.5473	0.1276	0.0460	0.045*
C1	0.9083 (2)	0.1638 (2)	−0.17555 (19)	0.0321 (4)
C2	1.0121 (2)	0.1192 (2)	−0.2840 (2)	0.0416 (5)
H2B	1.1059	0.0937	−0.2862	0.048 (7)*
C3	0.9745 (3)	0.1129 (3)	−0.3888 (2)	0.0510 (6)
H3B	1.0438	0.0832	−0.4619	0.063 (8)*
C4	0.8365 (3)	0.1497 (3)	−0.3867 (2)	0.0549 (7)
H4B	0.8124	0.1436	−0.4575	0.062 (8)*
C5	0.7330 (2)	0.1963 (2)	−0.2791 (2)	0.0440 (6)
H5A	0.6394	0.2210	−0.2778	0.043 (6)*
C6	0.7681 (2)	0.2058 (2)	−0.17350 (19)	0.0326 (5)
C7	0.6613 (2)	0.2667 (2)	−0.06062 (19)	0.0342 (5)
H7A	0.5793	0.3126	−0.0840	0.041 (6)*
H7B	0.7030	0.3318	−0.0398	0.037 (6)*
C8	0.5474 (2)	0.22312 (18)	0.18374 (18)	0.0291 (4)
C9	0.6647 (2)	0.2556 (2)	0.2224 (2)	0.0426 (5)
H9A	0.7140	0.3223	0.1588	0.044 (7)*
H9B	0.7333	0.1770	0.2278	0.051 (7)*
C10	0.5976 (3)	0.3071 (3)	0.3537 (2)	0.0566 (7)
H10A	0.6724	0.3291	0.3790	0.098 (11)*
C11	0.4734 (3)	0.1157 (2)	0.2835 (2)	0.0458 (6)
H11A	0.5417	0.0370	0.2889	0.043 (6)*
H11B	0.3995	0.0927	0.2592	0.054 (7)*
C12	0.4893 (3)	0.4311 (3)	0.3442 (3)	0.0554 (7)
H12A	0.4482	0.4651	0.4261	0.076 (9)*
H12B	0.5367	0.4990	0.2807	0.065 (8)*
C13	0.3727 (3)	0.3962 (2)	0.3060 (2)	0.0483 (6)
H13A	0.3030	0.4752	0.3006	0.069 (8)*
C14	0.4387 (2)	0.3461 (2)	0.1752 (2)	0.0380 (5)
H14A	0.3649	0.3249	0.1495	0.052 (7)*
H14B	0.4851	0.4143	0.1114	0.040 (6)*
C15	0.2985 (3)	0.2895 (3)	0.4054 (2)	0.0572 (7)
H15A	0.2242	0.2672	0.3811	0.070 (9)*
H15B	0.2548	0.3214	0.4882	0.062 (8)*
C16	0.4079 (3)	0.1676 (3)	0.4138 (2)	0.0565 (7)
H16A	0.3603	0.0989	0.4780	0.073 (9)*
C17	0.5229 (4)	0.2011 (3)	0.4530 (3)	0.0684 (8)
H17A	0.5911	0.1227	0.4600	0.085 (10)*
H17B	0.4812	0.2328	0.5360	0.065 (8)*

	U11	U22	U33	U12	U13	U23
S1	0.0308 (3)	0.0307 (3)	0.0430 (3)	−0.0026 (2)	−0.0129 (2)	−0.0076 (2)
O1	0.0865 (14)	0.0502 (11)	0.0455 (10)	−0.0061 (10)	0.0014 (9)	0.0004 (9)
O2	0.0344 (8)	0.0404 (8)	0.0655 (10)	−0.0005 (7)	−0.0227 (7)	−0.0227 (8)
O3	0.0351 (8)	0.0495 (10)	0.0789 (12)	0.0051 (7)	−0.0306 (8)	−0.0252 (9)
C18	0.0311 (10)	0.0294 (10)	0.0428 (12)	−0.0043 (8)	−0.0166 (9)	−0.0085 (9)
C19	0.0397 (12)	0.0277 (11)	0.0539 (14)	−0.0037 (9)	−0.0179 (11)	−0.0024 (10)
C20	0.0486 (14)	0.0294 (12)	0.0693 (17)	0.0021 (10)	−0.0239 (13)	−0.0161 (12)
C21	0.0429 (13)	0.0504 (14)	0.0610 (16)	0.0021 (11)	−0.0185 (12)	−0.0272 (13)
C22	0.0560 (15)	0.0543 (15)	0.0443 (14)	−0.0132 (13)	−0.0046 (12)	−0.0103 (12)
C23	0.0544 (14)	0.0322 (12)	0.0467 (13)	−0.0105 (11)	−0.0103 (11)	−0.0057 (10)
C24	0.071 (2)	0.083 (2)	0.085 (2)	0.000 (2)	−0.0134 (18)	−0.050 (2)
O4	0.0315 (8)	0.0535 (10)	0.0448 (9)	−0.0014 (7)	−0.0160 (7)	−0.0172 (8)
N1	0.0286 (8)	0.0274 (8)	0.0342 (9)	−0.0034 (7)	−0.0091 (7)	−0.0083 (7)
C1	0.0308 (10)	0.0328 (11)	0.0344 (11)	−0.0092 (9)	−0.0093 (8)	−0.0067 (9)
C2	0.0312 (11)	0.0471 (13)	0.0451 (13)	−0.0077 (10)	−0.0072 (10)	−0.0110 (11)
C3	0.0440 (13)	0.0687 (17)	0.0370 (13)	−0.0114 (12)	−0.0017 (11)	−0.0187 (12)
C4	0.0516 (15)	0.085 (2)	0.0323 (12)	−0.0164 (14)	−0.0124 (11)	−0.0139 (13)
C5	0.0361 (12)	0.0604 (15)	0.0356 (12)	−0.0084 (11)	−0.0118 (10)	−0.0058 (11)
C6	0.0301 (10)	0.0341 (11)	0.0328 (10)	−0.0062 (8)	−0.0081 (8)	−0.0050 (9)
C7	0.0315 (11)	0.0318 (11)	0.0368 (11)	−0.0030 (9)	−0.0092 (9)	−0.0042 (9)
C8	0.0304 (10)	0.0266 (10)	0.0315 (10)	−0.0024 (8)	−0.0102 (8)	−0.0087 (8)
C9	0.0385 (12)	0.0485 (14)	0.0477 (13)	−0.0038 (11)	−0.0202 (10)	−0.0135 (11)
C10	0.0604 (16)	0.0713 (18)	0.0536 (15)	−0.0102 (14)	−0.0294 (13)	−0.0232 (14)
C11	0.0560 (15)	0.0351 (12)	0.0390 (12)	−0.0112 (11)	−0.0027 (11)	−0.0087 (10)
C12	0.0723 (18)	0.0459 (14)	0.0525 (16)	−0.0113 (13)	−0.0156 (13)	−0.0245 (13)
C13	0.0493 (14)	0.0387 (13)	0.0528 (14)	0.0085 (11)	−0.0133 (12)	−0.0188 (11)
C14	0.0381 (12)	0.0351 (11)	0.0410 (12)	0.0034 (9)	−0.0155 (10)	−0.0097 (10)
C15	0.0503 (15)	0.0623 (17)	0.0482 (15)	−0.0076 (13)	0.0052 (12)	−0.0250 (13)
C16	0.0745 (18)	0.0446 (14)	0.0359 (13)	−0.0130 (13)	0.0009 (12)	−0.0048 (11)
C17	0.096 (2)	0.0683 (19)	0.0377 (14)	0.0072 (18)	−0.0260 (15)	−0.0122 (14)

S1—O1	1.4319 (18)	C5—C6	1.384 (3)
S1—O3	1.4468 (16)	C5—H5A	0.9300
S1—O2	1.4675 (15)	C6—C7	1.498 (3)
S1—C18	1.764 (2)	C7—H7A	0.9700
C18—C23	1.382 (3)	C7—H7B	0.9700
C18—C19	1.383 (3)	C8—C9	1.520 (3)
C19—C20	1.377 (3)	C8—C14	1.527 (3)
C19—H19A	0.9300	C8—C11	1.528 (3)
C20—C21	1.378 (3)	C9—C10	1.542 (3)
C20—H20A	0.9300	C9—H9A	0.9700
C21—C22	1.392 (4)	C9—H9B	0.9701
C21—C24	1.523 (4)	C10—C17	1.518 (4)
C22—C23	1.374 (3)	C10—C12	1.534 (4)
C22—H22A	0.9300	C10—H10A	0.9799
C23—H23A	0.9300	C11—C16	1.533 (3)
C24—H24A	0.9600	C11—H11A	0.9700
C24—H24B	0.9601	C11—H11B	0.9699
C24—H24C	0.9599	C12—C13	1.523 (4)
O4—C1	1.360 (2)	C12—H12A	0.9700
O4—H4A	0.8200	C12—H12B	0.9700
N1—C7	1.497 (2)	C13—C15	1.521 (4)
N1—C8	1.524 (2)	C13—C14	1.530 (3)
N1—H1A	0.9000	C13—H13A	0.9800
N1—H1B	0.8999	C14—H14A	0.9700
C1—C2	1.386 (3)	C14—H14B	0.9700
C1—C6	1.397 (3)	C15—C16	1.524 (4)
C2—C3	1.381 (3)	C15—H15A	0.9699
C2—H2B	0.9300	C15—H15B	0.9700
C3—C4	1.370 (4)	C16—C17	1.508 (4)
C3—H3B	0.9301	C16—H16A	0.9799
C4—C5	1.385 (3)	C17—H17A	0.9700
C4—H4B	0.9300	C17—H17B	0.9700
O1—S1—O3	113.98 (12)	C9—C8—N1	109.63 (16)
O1—S1—O2	113.46 (11)	C9—C8—C14	110.36 (17)
O3—S1—O2	109.68 (10)	N1—C8—C14	110.60 (16)
O1—S1—C18	107.64 (11)	C9—C8—C11	109.08 (18)
O3—S1—C18	105.85 (10)	N1—C8—C11	107.61 (15)
O2—S1—C18	105.56 (9)	C14—C8—C11	109.50 (18)
C23—C18—C19	119.4 (2)	C8—C9—C10	108.90 (18)
C23—C18—S1	119.99 (16)	C8—C9—H9A	109.9
C19—C18—S1	120.54 (17)	C10—C9—H9A	109.9
C20—C19—C18	119.9 (2)	C8—C9—H9B	109.9
C20—C19—H19A	120.1	C10—C9—H9B	109.9
C18—C19—H19A	120.0	H9A—C9—H9B	108.3
C19—C20—C21	121.4 (2)	C17—C10—C12	109.5 (2)
C19—C20—H20A	119.3	C17—C10—C9	109.4 (2)
C21—C20—H20A	119.3	C12—C10—C9	109.5 (2)
C20—C21—C22	118.1 (2)	C17—C10—H10A	109.5
C20—C21—C24	120.6 (2)	C12—C10—H10A	109.5
C22—C21—C24	121.2 (3)	C9—C10—H10A	109.5
C23—C22—C21	120.9 (2)	C8—C11—C16	108.81 (18)
C23—C22—H22A	119.5	C8—C11—H11A	109.9
C21—C22—H22A	119.5	C16—C11—H11A	109.9
C22—C23—C18	120.2 (2)	C8—C11—H11B	110.0
C22—C23—H23A	119.9	C16—C11—H11B	109.9
C18—C23—H23A	119.9	H11A—C11—H11B	108.3
C21—C24—H24A	109.4	C13—C12—C10	109.3 (2)
C21—C24—H24B	109.5	C13—C12—H12A	109.9
H24A—C24—H24B	109.5	C10—C12—H12A	109.9
C21—C24—H24C	109.5	C13—C12—H12B	109.8
H24A—C24—H24C	109.5	C10—C12—H12B	109.7
H24B—C24—H24C	109.5	H12A—C12—H12B	108.3
C1—O4—H4A	109.4	C15—C13—C12	109.8 (2)
C7—N1—C8	116.28 (14)	C15—C13—C14	109.65 (19)
C7—N1—H1A	108.2	C12—C13—C14	109.3 (2)
C8—N1—H1A	108.2	C15—C13—H13A	109.3
C7—N1—H1B	108.2	C12—C13—H13A	109.3
C8—N1—H1B	108.2	C14—C13—H13A	109.4
H1A—N1—H1B	107.4	C8—C14—C13	109.29 (17)
O4—C1—C2	123.22 (19)	C8—C14—H14A	109.9
O4—C1—C6	116.32 (18)	C13—C14—H14A	109.8
C2—C1—C6	120.45 (19)	C8—C14—H14B	109.8
C3—C2—C1	119.2 (2)	C13—C14—H14B	109.8
C3—C2—H2B	120.3	H14A—C14—H14B	108.3
C1—C2—H2B	120.4	C13—C15—C16	108.9 (2)
C4—C3—C2	120.9 (2)	C13—C15—H15A	109.9
C4—C3—H3B	119.5	C16—C15—H15A	109.8
C2—C3—H3B	119.5	C13—C15—H15B	110.0
C3—C4—C5	119.9 (2)	C16—C15—H15B	109.9
C3—C4—H4B	120.0	H15A—C15—H15B	108.3
C5—C4—H4B	120.1	C17—C16—C15	110.2 (2)
C6—C5—C4	120.4 (2)	C17—C16—C11	110.0 (2)
C6—C5—H5A	119.8	C15—C16—C11	109.6 (2)
C4—C5—H5A	119.8	C17—C16—H16A	109.0
C5—C6—C1	119.01 (19)	C15—C16—H16A	109.0
C5—C6—C7	121.43 (19)	C11—C16—H16A	109.0
C1—C6—C7	119.47 (18)	C16—C17—C10	109.3 (2)
N1—C7—C6	113.46 (16)	C16—C17—H17A	109.8
N1—C7—H7A	108.9	C10—C17—H17A	109.9
C6—C7—H7A	108.9	C16—C17—H17B	109.7
N1—C7—H7B	108.9	C10—C17—H17B	109.8
C6—C7—H7B	108.9	H17A—C17—H17B	108.3
H7A—C7—H7B	107.7

Cg is the centroid of the C18–C23 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.90	2.09	2.922 (2)	154.
N1—H1B···O3	0.90	2.05	2.860 (2)	150.
O4—H4A···O2ii	0.82	1.90	2.719 (2)	180.
C14—H14A···Cg	0.97	2.75	3.668 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C18–C23 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.90	2.09	2.922 (2)	154
N1—H1B⋯O3	0.90	2.05	2.860 (2)	150
O4—H4A⋯O2ii	0.82	1.90	2.719 (2)	180
C14—H14A⋯Cg	0.97	2.75	3.668 (3)	158

Symmetry codes: (i) ; (ii) .