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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3383
https://doi.org/10.1107/S1600536811048860

N-(2-Hy­dr­oxy­benz­yl)adamantan-1-aminium 4-methyl­benzene­sulfonate

Shao-Gang Houa*

aDepartment of Chemical & Environmental Engineering, Anyang Institute of Technology, Anyang 455000, People's Republic of China
*Correspondence e-mail: ayithou@yahoo.com.cn

(Received 12 November 2011; accepted 16 November 2011; online 19 November 2011)

In the crystal structure of the title salt, C17H24NO+·C7H7O3S−, the N-(2-hy­droxy­benz­yl)adamantan-1-aminium cations and 4-methyl­benzene­sulfonate anions are linked by O—H⋯O and N—H⋯O hydrogen bonds. C—H⋯π inter­actions are also observed between the cation and the anion.

Related literature

For related compounds, see: Blagden et al. (2008[Blagden, N., Berry, D. J., Parkin, A., Javed, H., Ibrahim, A., Gavan, P. T., De Matos, L. L. & Seaton, C. C. (2008). New J. Chem. 32, 1659-1672.]); Vishweshwar et al. (2006[Vishweshwar, P., McMahon, J. A., Bis, J. A. & Zaworotko, M. J. (2006). J. Pharm. Sci. 95, 499-516.]); Kapildev et al. (2011[Kapildev, K. A., Nitin, G. T. & Raj, S. (2011). Mol. Pharm. 8, 982-989.]); Schultheiss & Newman (2009[Schultheiss, N. & Newman, A. (2009). Cryst. Growth Des., 9, 2950-2967.]).

[Scheme 1]

Experimental

Crystal data

  • C17H24NO+·C7H7O3S−

  • Mr = 429.57

  • Triclinic, [P \overline 1]

  • 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.90, Tmax = 0.99

  • 11276 measured reflections

  • 4940 independent reflections

  • 3641 reflections with I > 2σ(I)

  • Rint = 0.051
Refinement

  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 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

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) -x+1, -y, -z; (ii) x+1, y, z.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811048860/xu5389sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048860/xu5389Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811048860/xu5389Isup3.cml

checkCIF report


Comment top

Organic salts are becoming increasingly important as new molecule-based crystalline materials with the potential to provide optimal physical properties whilst retaining the chemical properties of the organic components (Blagden et al., 2008; Vishweshwar et al., 2006). Physicochemical properties such as the melting point, stability and solubility can be tuned through crystallization (Kapildev et al., 2011; Schultheiss & Newman, 2009). The synthesis of organic salts often relies on the acid-amide H-bonds interactions. Herein, we report the crystal structure of the title compound, N-(2-hydroxybenzyl)adamantan-1-aminium 4-methylbenzenesulfonate.

The asymmetric unit is composed of one N-(2-Hydroxybenzyl)adamantan-1-aminium cation and one 4-methylbenzenesulfonate anion. The amine N1 atom was protonated. And the sulfonic group was deprotonated to keep the charge balance. The two benzene rings are nearly perpendicular and twisted from each other by a dihedral of 83.11 (1)°. The geometric parameters of the title compound are in the normal range.

In the crystal structure, all the hydroxy and amino H atoms are involved in intermolecular O—H···O and N—H···O hydrogen bonds interactions with the sulfonic O atoms. These hydrogen bonds link the molecules into an one-dimentional chain parallel to the a-axis (Table 1 and Fig.2).

Related literature top

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

Experimental top

A mixture of N-(2-hydroxybenzyl)adamantan-1-amine (2.0 mmol), 4-methylbenzenesulfonic acid (2.0 mL) and 20 mL distilled water were added into a 50 ml flask and refluxed for 5 h, then cooled and filtrated. The solution was evaporated slowly in the air. Colorless block crystals suitable for X-ray analysis were obtained after one week.

Refinement top

All H atoms attached to C atoms were fixed geometrically and treated as riding with C–H = 0.93 Å (aromatic), C–H = 0.97 Å (methylene), C–H = 0.98 Å (methine) and C–H = 0.96 Å (methyl) with Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.5Ueq(methyl). H atoms bonded to N and O atoms were located in a difference Fourier map and restrained with the H—N1 = 0.90 (2)Å and H—O4 = 0.82 (2)Å. In the last stage of refinement they were treated as riding on the N and O atoms with Uiso(H) = 1.5Ueq(N,O).

Structure description top

Organic salts are becoming increasingly important as new molecule-based crystalline materials with the potential to provide optimal physical properties whilst retaining the chemical properties of the organic components (Blagden et al., 2008; Vishweshwar et al., 2006). Physicochemical properties such as the melting point, stability and solubility can be tuned through crystallization (Kapildev et al., 2011; Schultheiss & Newman, 2009). The synthesis of organic salts often relies on the acid-amide H-bonds interactions. Herein, we report the crystal structure of the title compound, N-(2-hydroxybenzyl)adamantan-1-aminium 4-methylbenzenesulfonate.

The asymmetric unit is composed of one N-(2-Hydroxybenzyl)adamantan-1-aminium cation and one 4-methylbenzenesulfonate anion. The amine N1 atom was protonated. And the sulfonic group was deprotonated to keep the charge balance. The two benzene rings are nearly perpendicular and twisted from each other by a dihedral of 83.11 (1)°. The geometric parameters of the title compound are in the normal range.

In the crystal structure, all the hydroxy and amino H atoms are involved in intermolecular O—H···O and N—H···O hydrogen bonds interactions with the sulfonic O atoms. These hydrogen bonds link the molecules into an one-dimentional chain parallel to the a-axis (Table 1 and Fig.2).

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

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed along the b axis showing the one-dimensionnal hydrogen bondings chain (dashed line).
N-(2-Hydroxybenzyl)adamantan-1-aminium 4-methylbenzenesulfonate top
Crystal data top
C17H24NO+·C7H7O3S−Z = 2
Mr = 429.57F(000) = 460
Triclinic, P1Dx = 1.319 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.159 (2) ÅCell parameters from 4940 reflections
b = 10.413 (2) Åθ = 3.2–27.5°
c = 11.270 (2) ŵ = 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
Data collection top
Rigaku Mercury2
diffractometer		4940 independent reflections
Radiation source: fine-focus sealed tube3641 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.2°
CCD profile fitting scansh = −13→13
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −13→13
Tmin = 0.90, Tmax = 0.99l = −14→14
11276 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-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 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
Crystal data top
C17H24NO+·C7H7O3S−γ = 78.49 (3)°
Mr = 429.57V = 1081.8 (4) Å3
Triclinic, P1Z = 2
a = 10.159 (2) ÅMo Kα radiation
b = 10.413 (2) ŵ = 0.18 mm−1
c = 11.270 (2) ÅT = 298 K
α = 79.03 (3)°0.30 × 0.25 × 0.15 mm
β = 69.06 (3)°
Data collection top
Rigaku Mercury2
diffractometer		4940 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		3641 reflections with I > 2σ(I)
Tmin = 0.90, Tmax = 0.99Rint = 0.051
11276 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.157H-atom parameters constrained
S = 1.08Δρmax = 0.30 e Å−3
4940 reflectionsΔρmin = −0.37 e Å−3
299 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.29772 (5)0.18203 (5)−0.09359 (5)0.03453 (17)
O10.3379 (2)0.27308 (18)−0.20841 (17)0.0687 (6)
O20.21525 (15)0.08446 (15)−0.10027 (16)0.0436 (4)
O30.41568 (16)0.11518 (16)−0.05151 (17)0.0505 (4)
C180.1835 (2)0.2733 (2)0.0305 (2)0.0327 (5)
C190.1698 (2)0.4098 (2)0.0133 (2)0.0403 (5)
H19A0.21680.4545−0.06580.039 (6)*
C200.0866 (3)0.4795 (2)0.1134 (3)0.0477 (6)
H20A0.07860.57120.10110.049 (7)*
C210.0147 (3)0.4160 (2)0.2312 (3)0.0496 (6)
C220.0275 (3)0.2787 (3)0.2467 (3)0.0536 (6)
H22A−0.02120.23400.32520.053 (7)*
C230.1107 (3)0.2083 (2)0.1477 (2)0.0455 (6)
H23A0.11820.11660.15960.052 (7)*
C24−0.0759 (4)0.4946 (4)0.3410 (4)0.0796 (10)
H24A−0.11740.43500.41550.107 (14)*
H24B−0.15030.55400.31700.154 (19)*
H24C−0.01730.54430.35970.107 (13)*
O40.93542 (15)0.17176 (15)−0.06761 (14)0.0415 (4)
H4A1.01990.1458−0.07780.062*
N10.61227 (17)0.16841 (15)0.05577 (15)0.0299 (4)
H1A0.68710.10670.05930.045*
H1B0.54730.12760.04600.045*
C10.9083 (2)0.1638 (2)−0.17555 (19)0.0321 (4)
C21.0121 (2)0.1192 (2)−0.2840 (2)0.0416 (5)
H2B1.10590.0937−0.28620.048 (7)*
C30.9745 (3)0.1129 (3)−0.3888 (2)0.0510 (6)
H3B1.04380.0832−0.46190.063 (8)*
C40.8365 (3)0.1497 (3)−0.3867 (2)0.0549 (7)
H4B0.81240.1436−0.45750.062 (8)*
C50.7330 (2)0.1963 (2)−0.2791 (2)0.0440 (6)
H5A0.63940.2210−0.27780.043 (6)*
C60.7681 (2)0.2058 (2)−0.17350 (19)0.0326 (5)
C70.6613 (2)0.2667 (2)−0.06062 (19)0.0342 (5)
H7A0.57930.3126−0.08400.041 (6)*
H7B0.70300.3318−0.03980.037 (6)*
C80.5474 (2)0.22312 (18)0.18374 (18)0.0291 (4)
C90.6647 (2)0.2556 (2)0.2224 (2)0.0426 (5)
H9A0.71400.32230.15880.044 (7)*
H9B0.73330.17700.22780.051 (7)*
C100.5976 (3)0.3071 (3)0.3537 (2)0.0566 (7)
H10A0.67240.32910.37900.098 (11)*
C110.4734 (3)0.1157 (2)0.2835 (2)0.0458 (6)
H11A0.54170.03700.28890.043 (6)*
H11B0.39950.09270.25920.054 (7)*
C120.4893 (3)0.4311 (3)0.3442 (3)0.0554 (7)
H12A0.44820.46510.42610.076 (9)*
H12B0.53670.49900.28070.065 (8)*
C130.3727 (3)0.3962 (2)0.3060 (2)0.0483 (6)
H13A0.30300.47520.30060.069 (8)*
C140.4387 (2)0.3461 (2)0.1752 (2)0.0380 (5)
H14A0.36490.32490.14950.052 (7)*
H14B0.48510.41430.11140.040 (6)*
C150.2985 (3)0.2895 (3)0.4054 (2)0.0572 (7)
H15A0.22420.26720.38110.070 (9)*
H15B0.25480.32140.48820.062 (8)*
C160.4079 (3)0.1676 (3)0.4138 (2)0.0565 (7)
H16A0.36030.09890.47800.073 (9)*
C170.5229 (4)0.2011 (3)0.4530 (3)0.0684 (8)
H17A0.59110.12270.46000.085 (10)*
H17B0.48120.23280.53600.065 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0308 (3)0.0307 (3)0.0430 (3)−0.0026 (2)−0.0129 (2)−0.0076 (2)
O10.0865 (14)0.0502 (11)0.0455 (10)−0.0061 (10)0.0014 (9)0.0004 (9)
O20.0344 (8)0.0404 (8)0.0655 (10)−0.0005 (7)−0.0227 (7)−0.0227 (8)
O30.0351 (8)0.0495 (10)0.0789 (12)0.0051 (7)−0.0306 (8)−0.0252 (9)
C180.0311 (10)0.0294 (10)0.0428 (12)−0.0043 (8)−0.0166 (9)−0.0085 (9)
C190.0397 (12)0.0277 (11)0.0539 (14)−0.0037 (9)−0.0179 (11)−0.0024 (10)
C200.0486 (14)0.0294 (12)0.0693 (17)0.0021 (10)−0.0239 (13)−0.0161 (12)
C210.0429 (13)0.0504 (14)0.0610 (16)0.0021 (11)−0.0185 (12)−0.0272 (13)
C220.0560 (15)0.0543 (15)0.0443 (14)−0.0132 (13)−0.0046 (12)−0.0103 (12)
C230.0544 (14)0.0322 (12)0.0467 (13)−0.0105 (11)−0.0103 (11)−0.0057 (10)
C240.071 (2)0.083 (2)0.085 (2)0.000 (2)−0.0134 (18)−0.050 (2)
O40.0315 (8)0.0535 (10)0.0448 (9)−0.0014 (7)−0.0160 (7)−0.0172 (8)
N10.0286 (8)0.0274 (8)0.0342 (9)−0.0034 (7)−0.0091 (7)−0.0083 (7)
C10.0308 (10)0.0328 (11)0.0344 (11)−0.0092 (9)−0.0093 (8)−0.0067 (9)
C20.0312 (11)0.0471 (13)0.0451 (13)−0.0077 (10)−0.0072 (10)−0.0110 (11)
C30.0440 (13)0.0687 (17)0.0370 (13)−0.0114 (12)−0.0017 (11)−0.0187 (12)
C40.0516 (15)0.085 (2)0.0323 (12)−0.0164 (14)−0.0124 (11)−0.0139 (13)
C50.0361 (12)0.0604 (15)0.0356 (12)−0.0084 (11)−0.0118 (10)−0.0058 (11)
C60.0301 (10)0.0341 (11)0.0328 (10)−0.0062 (8)−0.0081 (8)−0.0050 (9)
C70.0315 (11)0.0318 (11)0.0368 (11)−0.0030 (9)−0.0092 (9)−0.0042 (9)
C80.0304 (10)0.0266 (10)0.0315 (10)−0.0024 (8)−0.0102 (8)−0.0087 (8)
C90.0385 (12)0.0485 (14)0.0477 (13)−0.0038 (11)−0.0202 (10)−0.0135 (11)
C100.0604 (16)0.0713 (18)0.0536 (15)−0.0102 (14)−0.0294 (13)−0.0232 (14)
C110.0560 (15)0.0351 (12)0.0390 (12)−0.0112 (11)−0.0027 (11)−0.0087 (10)
C120.0723 (18)0.0459 (14)0.0525 (16)−0.0113 (13)−0.0156 (13)−0.0245 (13)
C130.0493 (14)0.0387 (13)0.0528 (14)0.0085 (11)−0.0133 (12)−0.0188 (11)
C140.0381 (12)0.0351 (11)0.0410 (12)0.0034 (9)−0.0155 (10)−0.0097 (10)
C150.0503 (15)0.0623 (17)0.0482 (15)−0.0076 (13)0.0052 (12)−0.0250 (13)
C160.0745 (18)0.0446 (14)0.0359 (13)−0.0130 (13)0.0009 (12)−0.0048 (11)
C170.096 (2)0.0683 (19)0.0377 (14)0.0072 (18)−0.0260 (15)−0.0122 (14)
Geometric parameters (Å, º) top
S1—O11.4319 (18)C5—C61.384 (3)
S1—O31.4468 (16)C5—H5A0.9300
S1—O21.4675 (15)C6—C71.498 (3)
S1—C181.764 (2)C7—H7A0.9700
C18—C231.382 (3)C7—H7B0.9700
C18—C191.383 (3)C8—C91.520 (3)
C19—C201.377 (3)C8—C141.527 (3)
C19—H19A0.9300C8—C111.528 (3)
C20—C211.378 (3)C9—C101.542 (3)
C20—H20A0.9300C9—H9A0.9700
C21—C221.392 (4)C9—H9B0.9701
C21—C241.523 (4)C10—C171.518 (4)
C22—C231.374 (3)C10—C121.534 (4)
C22—H22A0.9300C10—H10A0.9799
C23—H23A0.9300C11—C161.533 (3)
C24—H24A0.9600C11—H11A0.9700
C24—H24B0.9601C11—H11B0.9699
C24—H24C0.9599C12—C131.523 (4)
O4—C11.360 (2)C12—H12A0.9700
O4—H4A0.8200C12—H12B0.9700
N1—C71.497 (2)C13—C151.521 (4)
N1—C81.524 (2)C13—C141.530 (3)
N1—H1A0.9000C13—H13A0.9800
N1—H1B0.8999C14—H14A0.9700
C1—C21.386 (3)C14—H14B0.9700
C1—C61.397 (3)C15—C161.524 (4)
C2—C31.381 (3)C15—H15A0.9699
C2—H2B0.9300C15—H15B0.9700
C3—C41.370 (4)C16—C171.508 (4)
C3—H3B0.9301C16—H16A0.9799
C4—C51.385 (3)C17—H17A0.9700
C4—H4B0.9300C17—H17B0.9700
O1—S1—O3113.98 (12)C9—C8—N1109.63 (16)
O1—S1—O2113.46 (11)C9—C8—C14110.36 (17)
O3—S1—O2109.68 (10)N1—C8—C14110.60 (16)
O1—S1—C18107.64 (11)C9—C8—C11109.08 (18)
O3—S1—C18105.85 (10)N1—C8—C11107.61 (15)
O2—S1—C18105.56 (9)C14—C8—C11109.50 (18)
C23—C18—C19119.4 (2)C8—C9—C10108.90 (18)
C23—C18—S1119.99 (16)C8—C9—H9A109.9
C19—C18—S1120.54 (17)C10—C9—H9A109.9
C20—C19—C18119.9 (2)C8—C9—H9B109.9
C20—C19—H19A120.1C10—C9—H9B109.9
C18—C19—H19A120.0H9A—C9—H9B108.3
C19—C20—C21121.4 (2)C17—C10—C12109.5 (2)
C19—C20—H20A119.3C17—C10—C9109.4 (2)
C21—C20—H20A119.3C12—C10—C9109.5 (2)
C20—C21—C22118.1 (2)C17—C10—H10A109.5
C20—C21—C24120.6 (2)C12—C10—H10A109.5
C22—C21—C24121.2 (3)C9—C10—H10A109.5
C23—C22—C21120.9 (2)C8—C11—C16108.81 (18)
C23—C22—H22A119.5C8—C11—H11A109.9
C21—C22—H22A119.5C16—C11—H11A109.9
C22—C23—C18120.2 (2)C8—C11—H11B110.0
C22—C23—H23A119.9C16—C11—H11B109.9
C18—C23—H23A119.9H11A—C11—H11B108.3
C21—C24—H24A109.4C13—C12—C10109.3 (2)
C21—C24—H24B109.5C13—C12—H12A109.9
H24A—C24—H24B109.5C10—C12—H12A109.9
C21—C24—H24C109.5C13—C12—H12B109.8
H24A—C24—H24C109.5C10—C12—H12B109.7
H24B—C24—H24C109.5H12A—C12—H12B108.3
C1—O4—H4A109.4C15—C13—C12109.8 (2)
C7—N1—C8116.28 (14)C15—C13—C14109.65 (19)
C7—N1—H1A108.2C12—C13—C14109.3 (2)
C8—N1—H1A108.2C15—C13—H13A109.3
C7—N1—H1B108.2C12—C13—H13A109.3
C8—N1—H1B108.2C14—C13—H13A109.4
H1A—N1—H1B107.4C8—C14—C13109.29 (17)
O4—C1—C2123.22 (19)C8—C14—H14A109.9
O4—C1—C6116.32 (18)C13—C14—H14A109.8
C2—C1—C6120.45 (19)C8—C14—H14B109.8
C3—C2—C1119.2 (2)C13—C14—H14B109.8
C3—C2—H2B120.3H14A—C14—H14B108.3
C1—C2—H2B120.4C13—C15—C16108.9 (2)
C4—C3—C2120.9 (2)C13—C15—H15A109.9
C4—C3—H3B119.5C16—C15—H15A109.8
C2—C3—H3B119.5C13—C15—H15B110.0
C3—C4—C5119.9 (2)C16—C15—H15B109.9
C3—C4—H4B120.0H15A—C15—H15B108.3
C5—C4—H4B120.1C17—C16—C15110.2 (2)
C6—C5—C4120.4 (2)C17—C16—C11110.0 (2)
C6—C5—H5A119.8C15—C16—C11109.6 (2)
C4—C5—H5A119.8C17—C16—H16A109.0
C5—C6—C1119.01 (19)C15—C16—H16A109.0
C5—C6—C7121.43 (19)C11—C16—H16A109.0
C1—C6—C7119.47 (18)C16—C17—C10109.3 (2)
N1—C7—C6113.46 (16)C16—C17—H17A109.8
N1—C7—H7A108.9C10—C17—H17A109.9
C6—C7—H7A108.9C16—C17—H17B109.7
N1—C7—H7B108.9C10—C17—H17B109.8
C6—C7—H7B108.9H17A—C17—H17B108.3
H7A—C7—H7B107.7
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C18–C23 benzene ring.
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.902.092.922 (2)154
N1—H1B···O30.902.052.860 (2)150
O4—H4A···O2ii0.821.902.719 (2)180
C14—H14A···Cg0.972.753.668 (3)158
Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC17H24NO+·C7H7O3S−
Mr429.57
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)10.159 (2), 10.413 (2), 11.270 (2)
α, β, γ (°)79.03 (3), 69.06 (3), 78.49 (3)
V (Å3)1081.8 (4)
Z2
Radiation typeMo Kα
µ (mm−1)0.18
Crystal size (mm)0.30 × 0.25 × 0.15
Data collection
DiffractometerRigaku Mercury2
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.90, 0.99
No. of measured, independent and
observed [I > 2σ(I)] reflections		11276, 4940, 3641
Rint0.051
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.157, 1.08
No. of reflections4940
No. of parameters299
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.30, −0.37

Computer programs: CrystalClear (Rigaku, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C18–C23 benzene ring.
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.902.092.922 (2)154.3
N1—H1B···O30.902.052.860 (2)149.9
O4—H4A···O2ii0.821.902.719 (2)179.5
C14—H14A···Cg0.972.753.668 (3)158
Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y, z.
 

Acknowledgements

This work was supported by the start-up fund of Anyang Institute of Technology, China.

References

First citationBlagden, N., Berry, D. J., Parkin, A., Javed, H., Ibrahim, A., Gavan, P. T., De Matos, L. L. & Seaton, C. C. (2008). New J. Chem. 32, 1659–1672.  Web of Science CSD CrossRef CAS Google Scholar
 First citationKapildev, K. A., Nitin, G. T. & Raj, S. (2011). Mol. Pharm. 8, 982–989.  Web of Science PubMed Google Scholar
 First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSchultheiss, N. & Newman, A. (2009). Cryst. Growth Des., 9, 2950–2967.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationVishweshwar, P., McMahon, J. A., Bis, J. A. & Zaworotko, M. J. (2006). J. Pharm. Sci. 95, 499–516.  Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3383
https://doi.org/10.1107/S1600536811048860
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