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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 71| Part 1| January 2015| Page o20
https://doi.org/10.1107/S2056989014025353

Crystal structure of 1-methane­sulfonyl-1,2,3,4-tetra­hydro­quinoline

S. Jeyaseelan,a S. L. Nagendra Babu,b G. Venkateshappa,c P. Raghavendra Kumarc and B. S. Palakshamurthyb*

aDepartment of Physics, St Philomenas College (Autonomous), Mysore, Karnataka 570 015, India, bDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, and cDepartment of Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India
*Correspondence e-mail: palaksha.bspm@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 9 November 2014; accepted 19 November 2014; online 1 January 2015)

In the title compound, C10H13NO2S, the heterocyclic ring adopts a half-chair conformation and the bond-angle sum at the N atom is 347.9°. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R22(8) loops.

CCDC reference: 1034951

Similar articles

1. Related literature

For background to tetra­hydro­quinolines, see: Chulakov et al. (2012[Chulakov, E. N., Levit, G. L., Tumashov, A. A., Sadretdinova, L. Sh. & Krasnov, V. P. (2012). Chem. Heterocycl. Compd, 48, 724-732.]); Kadutskii et al. (2012[Kadutskii, A. P., Kozlov, N. G., Frolova, L. L., Alekseev, I. N. & Kuchin, A. V. (2012). Chem. Nat. Compd, 48, 404-411.]); Katritsky et al. (1996[Katritsky, A. R., Rachwal, S. & Rachwal, B. (1996). Tetrahedron, 52, 15031-15070.]); Keith et al. (2001[Keith, J. M., Larrow, J. F. & Jacobsen, E. N. (2001). Adv. Synth. Catal. 343, 5-27.]). For a related structure, see: Jeyaseelan et al. (2014[Jeyaseelan, S., Asha, K. V., Venkateshappa, G., Raghavendrakumar, P. & Palakshamurthy, B. S. (2014). Acta Cryst. E70, o1176.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C10H13NO2S

  • Mr = 211.27

  • Triclinic, [P \overline 1]

  • a = 5.5865 (2) Å

  • b = 9.2195 (4) Å

  • c = 10.1924 (4) Å

  • α = 85.798 (2)°

  • β = 84.686 (2)°

  • γ = 77.166 (2)°

  • V = 508.89 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.29 mm−1

  • T = 294 K

  • 0.24 × 0.20 × 0.16 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.933, Tmax = 0.955

  • 7417 measured reflections

  • 1973 independent reflections

  • 1844 reflections with I > 2σ(I)

  • Rint = 0.042

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.106

  • S = 1.07

  • 1973 reflections

  • 128 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C10—H10C⋯O2i 0.96 2.50 3.431 (2) 164
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]);; program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL2014.

Supporting information

CCDC reference: 1034951

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989014025353/hb7314sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989014025353/hb7314Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989014025353/hb7314Isup3.cml

checkCIF report


Chemical context top

Derivatives of tetra­hydro­quinolines display a wide range of physiological activities, they been found to be pesticides, anti­oxidants, photosensitizers, and dyes (Katritsky et al., 1996). Heterocyclic compounds of 1,2,3,4-tetra­hydro­quinoline derivatives play important role in synthesize efficient kinetic resolution with predominant (S,S)-(R,R)-diastereoisomers (Chulakov et al., 2012), optically active camphor moieties (Kadutskii et al., 2012), and biologically active compounds, synthetic inter­mediates (Keith et al., 2001).

In due course of our study, we have synthised a series of 1,2,3,4-tetra­hydro­quinoline with derivatives of suloponyl chlorides they exhibit a few pharmacological activities (our unpublished data). As a part of our study we have undertaken crystal structure determination of the title compound and the results are compared with crystal structure of 1-tosyl-1,2,3,4-tetra­hydro­quinoline­(II) (Jeyaseelan et al., 2014) .

Structural commentary top

The molecular structure of the title compound(I) is shown in Fig. 1. In both the compounds (I) and (II), the C1/C6–C9/N1 rings are in a half-chair conformation, with the methyl­ene C9 atom as the flap, but the bond-angle sum at the N atom in the compound (I) and (II) are 347.9° and 350.2°, respectively.

Supra­molecular features top

In the crystal, inversion dimers linked by pairs of C10—H10C···O2 hydrogen bonds generate R22(8) ring motifs.

Synthesis and crystallization top

To a stirred solution of 1,2,3,4-tetra­hydro­quinoline (10 mmol) in 30 ml dry methyl­ene dichloride, tri­ethyl­amine (15 mmol) was added at 0 - 5°C. To this reaction mixture methane­sulfonyl chloride (12 mmol) in 10 ml dry di­chloro­methane was added drop wise. After 2h of stirring at 15 - 20°C, the reaction mixture was washed with 5% Na2CO3 and brine. The organic phase was dried over Na2SO4 and then it was concentrated on vacuum to yield titled compound as colourless solid. The crude product was recrystallized from a slovent mixture of ethyl acetate and hexane­(1:2) to yield colourless prisms of (I).

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 1. The H atoms were positioned with idealized geometry using a riding model with C—H = 0.93-0.99 Å. All H-atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times of the U eq of the parent atom).

Related literature top

For background to tetrahydroquinolines, see: Chulakov et al. (2012); Kadutskii et al. (2012); Katritsky et al. (1996); Keith et al. (2001). For a related structure, see: Jeyaseelan et al. (2014).

Structure description top

Derivatives of tetra­hydro­quinolines display a wide range of physiological activities, they been found to be pesticides, anti­oxidants, photosensitizers, and dyes (Katritsky et al., 1996). Heterocyclic compounds of 1,2,3,4-tetra­hydro­quinoline derivatives play important role in synthesize efficient kinetic resolution with predominant (S,S)-(R,R)-diastereoisomers (Chulakov et al., 2012), optically active camphor moieties (Kadutskii et al., 2012), and biologically active compounds, synthetic inter­mediates (Keith et al., 2001).

In due course of our study, we have synthised a series of 1,2,3,4-tetra­hydro­quinoline with derivatives of suloponyl chlorides they exhibit a few pharmacological activities (our unpublished data). As a part of our study we have undertaken crystal structure determination of the title compound and the results are compared with crystal structure of 1-tosyl-1,2,3,4-tetra­hydro­quinoline­(II) (Jeyaseelan et al., 2014) .

The molecular structure of the title compound(I) is shown in Fig. 1. In both the compounds (I) and (II), the C1/C6–C9/N1 rings are in a half-chair conformation, with the methyl­ene C9 atom as the flap, but the bond-angle sum at the N atom in the compound (I) and (II) are 347.9° and 350.2°, respectively.

In the crystal, inversion dimers linked by pairs of C10—H10C···O2 hydrogen bonds generate R22(8) ring motifs.

For background to tetrahydroquinolines, see: Chulakov et al. (2012); Kadutskii et al. (2012); Katritsky et al. (1996); Keith et al. (2001). For a related structure, see: Jeyaseelan et al. (2014).

Synthesis and crystallization top

To a stirred solution of 1,2,3,4-tetra­hydro­quinoline (10 mmol) in 30 ml dry methyl­ene dichloride, tri­ethyl­amine (15 mmol) was added at 0 - 5°C. To this reaction mixture methane­sulfonyl chloride (12 mmol) in 10 ml dry di­chloro­methane was added drop wise. After 2h of stirring at 15 - 20°C, the reaction mixture was washed with 5% Na2CO3 and brine. The organic phase was dried over Na2SO4 and then it was concentrated on vacuum to yield titled compound as colourless solid. The crude product was recrystallized from a slovent mixture of ethyl acetate and hexane­(1:2) to yield colourless prisms of (I).

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 1. The H atoms were positioned with idealized geometry using a riding model with C—H = 0.93-0.99 Å. All H-atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times of the U eq of the parent atom).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008);; program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. The molecular packing of the title compound, dashed lines indicates the inversion dimers linked by pairs of C—H···O hydrogen bonds with R22(8) ring motifs.
1-Methanesulfonyl-1,2,3,4-tetrahydroquinoline top
Crystal data top
C10H13NO2SF(000) = 224
Mr = 211.27Prism
Triclinic, P1Dx = 1.379 Mg m−3
Hall symbol: -P 1Melting point: 414 K
a = 5.5865 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.2195 (4) ÅCell parameters from 1844 reflections
c = 10.1924 (4) Åθ = 2.0–26.0°
α = 85.798 (2)°µ = 0.29 mm−1
β = 84.686 (2)°T = 294 K
γ = 77.166 (2)°Prism, colourless
V = 508.89 (4) Å30.24 × 0.20 × 0.16 mm
Z = 2
Data collection top
Bruker APEXII CCD
diffractometer		1973 independent reflections
Radiation source: fine-focus sealed tube1844 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
Detector resolution: 1.09 pixels mm-1θmax = 26.0°, θmin = 2.0°
phi and ω scansh = −6→6
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		k = −11→11
Tmin = 0.933, Tmax = 0.955l = −12→12
7417 measured reflections
Refinement top
Refinement on F2Primary atom site location: difference Fourier map
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0543P)2 + 0.1542P]
where P = (Fo2 + 2Fc2)/3
1973 reflections(Δ/σ)max = 0.001
128 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.31 e Å−3
0 constraints
Crystal data top
C10H13NO2Sγ = 77.166 (2)°
Mr = 211.27V = 508.89 (4) Å3
Triclinic, P1Z = 2
a = 5.5865 (2) ÅMo Kα radiation
b = 9.2195 (4) ŵ = 0.29 mm−1
c = 10.1924 (4) ÅT = 294 K
α = 85.798 (2)°0.24 × 0.20 × 0.16 mm
β = 84.686 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		1973 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		1844 reflections with I > 2σ(I)
Tmin = 0.933, Tmax = 0.955Rint = 0.042
7417 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 1.07Δρmax = 0.24 e Å−3
1973 reflectionsΔρmin = −0.31 e Å−3
128 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1−0.0188 (3)0.52244 (15)0.71208 (15)0.0682 (4)
C10.3459 (3)0.12140 (16)0.73875 (15)0.0323 (3)
C20.2249 (4)0.0388 (2)0.83231 (18)0.0478 (4)
H20.06350.07780.86390.057*
C30.3448 (4)−0.1007 (2)0.8780 (2)0.0620 (6)
H30.2647−0.15490.94130.074*
C40.5827 (4)−0.1601 (2)0.8300 (2)0.0593 (5)
H40.6643−0.25340.86190.071*
C50.6980 (3)−0.0810 (2)0.73512 (18)0.0480 (4)
H50.8574−0.12270.70220.058*
C60.5840 (3)0.06025 (17)0.68628 (15)0.0359 (4)
C70.7133 (3)0.1364 (2)0.57329 (19)0.0489 (4)
H7A0.87880.13550.59550.059*
H7B0.72730.07970.49540.059*
C80.5850 (4)0.2949 (2)0.54063 (19)0.0537 (5)
H8A0.63780.32440.45120.064*
H8B0.62930.36040.60010.064*
C90.3091 (4)0.3101 (2)0.55315 (16)0.0461 (4)
H9A0.22960.41270.53180.055*
H9B0.26480.24830.49030.055*
N10.2186 (2)0.26547 (14)0.68785 (12)0.0343 (3)
C100.3540 (4)0.4495 (2)0.8543 (2)0.0548 (5)
H10A0.44270.49780.78560.082*
H10B0.46190.36190.88900.082*
H10C0.29310.51650.92350.082*
O2−0.0312 (3)0.33906 (15)0.89749 (14)0.0592 (4)
S10.10556 (7)0.39877 (4)0.78957 (4)0.03662 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0777 (10)0.0463 (8)0.0683 (9)0.0213 (7)−0.0239 (8)−0.0061 (7)
C10.0337 (7)0.0307 (7)0.0331 (7)−0.0068 (6)−0.0033 (6)−0.0056 (6)
C20.0479 (10)0.0421 (9)0.0499 (10)−0.0084 (8)0.0107 (8)−0.0023 (7)
C30.0783 (15)0.0417 (10)0.0591 (12)−0.0096 (10)0.0141 (10)0.0071 (9)
C40.0768 (14)0.0358 (9)0.0578 (11)0.0021 (9)−0.0054 (10)0.0022 (8)
C50.0419 (9)0.0425 (9)0.0553 (10)0.0027 (7)−0.0041 (8)−0.0117 (8)
C60.0336 (8)0.0364 (8)0.0390 (8)−0.0080 (6)−0.0024 (6)−0.0093 (6)
C70.0381 (9)0.0537 (10)0.0543 (10)−0.0125 (8)0.0100 (8)−0.0084 (8)
C80.0626 (12)0.0528 (11)0.0455 (10)−0.0200 (9)0.0140 (9)−0.0013 (8)
C90.0606 (11)0.0445 (9)0.0308 (8)−0.0067 (8)−0.0049 (7)0.0003 (7)
N10.0350 (7)0.0333 (7)0.0336 (7)−0.0043 (5)−0.0030 (5)−0.0042 (5)
C100.0488 (10)0.0674 (12)0.0529 (11)−0.0158 (9)−0.0023 (8)−0.0261 (9)
O20.0526 (8)0.0569 (8)0.0645 (9)−0.0122 (6)0.0261 (7)−0.0179 (7)
S10.0304 (2)0.0346 (3)0.0418 (3)0.00108 (16)−0.00305 (16)−0.00688 (17)
Geometric parameters (Å, º) top
O1—S11.4227 (13)C7—H7B0.9700
C1—C21.396 (2)C8—C91.511 (3)
C1—C61.398 (2)C8—H8A0.9700
C1—N11.4446 (18)C8—H8B0.9700
C2—C31.381 (3)C9—N11.480 (2)
C2—H20.9300C9—H9A0.9700
C3—C41.379 (3)C9—H9B0.9700
C3—H30.9300N1—S11.6446 (13)
C4—C51.369 (3)C10—S11.7555 (18)
C4—H40.9300C10—H10A0.9600
C5—C61.394 (2)C10—H10B0.9600
C5—H50.9300C10—H10C0.9600
C6—C71.515 (2)O2—S11.4279 (13)
C7—C81.505 (3)S1—O11.4227 (13)
C7—H7A0.9700
C2—C1—C6120.12 (15)C9—C8—H8A109.6
C2—C1—N1120.16 (14)C7—C8—H8B109.6
C6—C1—N1119.53 (13)C9—C8—H8B109.6
C3—C2—C1120.02 (17)H8A—C8—H8B108.1
C3—C2—H2120.0N1—C9—C8111.80 (14)
C1—C2—H2120.0N1—C9—H9A109.3
C4—C3—C2120.28 (18)C8—C9—H9A109.3
C4—C3—H3119.9N1—C9—H9B109.3
C2—C3—H3119.9C8—C9—H9B109.3
C5—C4—C3119.56 (18)H9A—C9—H9B107.9
C5—C4—H4120.2C1—N1—C9114.89 (12)
C3—C4—H4120.2C1—N1—S1119.76 (10)
C4—C5—C6122.06 (16)C9—N1—S1117.41 (10)
C4—C5—H5119.0S1—C10—H10A109.5
C6—C5—H5119.0S1—C10—H10B109.5
C5—C6—C1117.87 (15)H10A—C10—H10B109.5
C5—C6—C7119.39 (15)S1—C10—H10C109.5
C1—C6—C7122.61 (15)H10A—C10—H10C109.5
C8—C7—C6114.00 (14)H10B—C10—H10C109.5
C8—C7—H7A108.8O1—S1—O2118.38 (10)
C6—C7—H7A108.8O1—S1—N1106.54 (8)
C8—C7—H7B108.8O2—S1—N1108.22 (7)
C6—C7—H7B108.8O1—S1—C10108.39 (10)
H7A—C7—H7B107.6O2—S1—C10107.06 (9)
C7—C8—C9110.45 (15)N1—S1—C10107.85 (8)
C7—C8—H8A109.6
C6—C1—C2—C33.1 (3)C6—C1—N1—C922.44 (19)
N1—C1—C2—C3178.13 (17)C2—C1—N1—S159.22 (18)
C1—C2—C3—C4−1.0 (3)C6—C1—N1—S1−125.77 (13)
C2—C3—C4—C5−1.1 (3)C8—C9—N1—C1−51.15 (19)
C3—C4—C5—C61.2 (3)C8—C9—N1—S197.83 (15)
C4—C5—C6—C10.9 (3)C1—N1—S1—O1−176.90 (12)
C4—C5—C6—C7−174.89 (18)C9—N1—S1—O135.68 (15)
C2—C1—C6—C5−3.1 (2)C1—N1—S1—O1−176.90 (12)
N1—C1—C6—C5−178.07 (13)C9—N1—S1—O135.68 (15)
C2—C1—C6—C7172.62 (15)C1—N1—S1—O2−48.59 (13)
N1—C1—C6—C7−2.4 (2)C9—N1—S1—O2163.98 (12)
C5—C6—C7—C8−173.18 (16)C1—N1—S1—O2−48.59 (13)
C1—C6—C7—C811.2 (2)C9—N1—S1—O2163.98 (12)
C6—C7—C8—C9−38.3 (2)C1—N1—S1—C1066.91 (14)
C7—C8—C9—N158.9 (2)C9—N1—S1—C10−80.52 (14)
C2—C1—N1—C9−152.58 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10C···O2i0.962.503.431 (2)164
Symmetry code: (i) −x, −y+1, −z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10C···O2i0.962.503.431 (2)164
Symmetry code: (i) −x, −y+1, −z+2.
 

Acknowledgements

SJ thanks Vision Group on Science and Technology, Government of Karnataka, for awarding a major project under CISE scheme (reference No. VGST/CISE/GRD-192/2013–14). BSP thanks Rajegowda, Department of Studies and Research in Physics, UCS, Tumkur University, Karnataka 572 103, India, for his support.

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 71| Part 1| January 2015| Page o20
https://doi.org/10.1107/S2056989014025353
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