Crystal structure of 1-methane-sulfonyl-1,2,3,4-tetra-hydro-quinoline.

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 R 2 (2)(8) loops.

Related literature

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 ▸).

Experimental

Crystal data

C10H13NO2S

M = 211.27

Triclinic,

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

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.933, T max = 0.955

7417 measured reflections

1973 independent reflections

1844 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 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

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT; 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.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989014025353/hb7314sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014025353/hb7314Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014025353/hb7314Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014025353/hb7314fig1.tif

The mol­ecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989014025353/hb7314fig2.tif

The mol­ecular packing of the title compound, dashed lines indicates the inversion dimers linked by pairs of C—H⋯O hydrogen bonds with (8) ring motifs.

CCDC reference: 1034951

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H13NO2S	F(000) = 224
Mr = 211.27	Prism
Triclinic, P1	Dx = 1.379 Mg m−3
Hall symbol: -P 1	Melting point: 414 K
a = 5.5865 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2195 (4) Å	Cell parameters from 1844 reflections
c = 10.1924 (4) Å	θ = 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) Å3	0.24 × 0.20 × 0.16 mm
Z = 2

Bruker APEXII CCD diffractometer	1973 independent reflections
Radiation source: fine-focus sealed tube	1844 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 1.09 pixels mm-1	θmax = 26.0°, θmin = 2.0°
phi and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −11→11
Tmin = 0.933, Tmax = 0.955	l = −12→12
7417 measured reflections

Refinement on F2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-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 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.31 e Å−3
0 constraints

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.

	x	y	z	Uiso*/Ueq
O1	−0.0188 (3)	0.52244 (15)	0.71208 (15)	0.0682 (4)
C1	0.3459 (3)	0.12140 (16)	0.73875 (15)	0.0323 (3)
C2	0.2249 (4)	0.0388 (2)	0.83231 (18)	0.0478 (4)
H2	0.0635	0.0778	0.8639	0.057*
C3	0.3448 (4)	−0.1007 (2)	0.8780 (2)	0.0620 (6)
H3	0.2647	−0.1549	0.9413	0.074*
C4	0.5827 (4)	−0.1601 (2)	0.8300 (2)	0.0593 (5)
H4	0.6643	−0.2534	0.8619	0.071*
C5	0.6980 (3)	−0.0810 (2)	0.73512 (18)	0.0480 (4)
H5	0.8574	−0.1227	0.7022	0.058*
C6	0.5840 (3)	0.06025 (17)	0.68628 (15)	0.0359 (4)
C7	0.7133 (3)	0.1364 (2)	0.57329 (19)	0.0489 (4)
H7A	0.8788	0.1355	0.5955	0.059*
H7B	0.7273	0.0797	0.4954	0.059*
C8	0.5850 (4)	0.2949 (2)	0.54063 (19)	0.0537 (5)
H8A	0.6378	0.3244	0.4512	0.064*
H8B	0.6293	0.3604	0.6001	0.064*
C9	0.3091 (4)	0.3101 (2)	0.55315 (16)	0.0461 (4)
H9A	0.2296	0.4127	0.5318	0.055*
H9B	0.2648	0.2483	0.4903	0.055*
N1	0.2186 (2)	0.26547 (14)	0.68785 (12)	0.0343 (3)
C10	0.3540 (4)	0.4495 (2)	0.8543 (2)	0.0548 (5)
H10A	0.4427	0.4978	0.7856	0.082*
H10B	0.4619	0.3619	0.8890	0.082*
H10C	0.2931	0.5165	0.9235	0.082*
O2	−0.0312 (3)	0.33906 (15)	0.89749 (14)	0.0592 (4)
S1	0.10556 (7)	0.39877 (4)	0.78957 (4)	0.03662 (17)

	U11	U22	U33	U12	U13	U23
O1	0.0777 (10)	0.0463 (8)	0.0683 (9)	0.0213 (7)	−0.0239 (8)	−0.0061 (7)
C1	0.0337 (7)	0.0307 (7)	0.0331 (7)	−0.0068 (6)	−0.0033 (6)	−0.0056 (6)
C2	0.0479 (10)	0.0421 (9)	0.0499 (10)	−0.0084 (8)	0.0107 (8)	−0.0023 (7)
C3	0.0783 (15)	0.0417 (10)	0.0591 (12)	−0.0096 (10)	0.0141 (10)	0.0071 (9)
C4	0.0768 (14)	0.0358 (9)	0.0578 (11)	0.0021 (9)	−0.0054 (10)	0.0022 (8)
C5	0.0419 (9)	0.0425 (9)	0.0553 (10)	0.0027 (7)	−0.0041 (8)	−0.0117 (8)
C6	0.0336 (8)	0.0364 (8)	0.0390 (8)	−0.0080 (6)	−0.0024 (6)	−0.0093 (6)
C7	0.0381 (9)	0.0537 (10)	0.0543 (10)	−0.0125 (8)	0.0100 (8)	−0.0084 (8)
C8	0.0626 (12)	0.0528 (11)	0.0455 (10)	−0.0200 (9)	0.0140 (9)	−0.0013 (8)
C9	0.0606 (11)	0.0445 (9)	0.0308 (8)	−0.0067 (8)	−0.0049 (7)	0.0003 (7)
N1	0.0350 (7)	0.0333 (7)	0.0336 (7)	−0.0043 (5)	−0.0030 (5)	−0.0042 (5)
C10	0.0488 (10)	0.0674 (12)	0.0529 (11)	−0.0158 (9)	−0.0023 (8)	−0.0261 (9)
O2	0.0526 (8)	0.0569 (8)	0.0645 (9)	−0.0122 (6)	0.0261 (7)	−0.0179 (7)
S1	0.0304 (2)	0.0346 (3)	0.0418 (3)	0.00108 (16)	−0.00305 (16)	−0.00688 (17)

O1—S1	1.4227 (13)	C7—H7B	0.9700
C1—C2	1.396 (2)	C8—C9	1.511 (3)
C1—C6	1.398 (2)	C8—H8A	0.9700
C1—N1	1.4446 (18)	C8—H8B	0.9700
C2—C3	1.381 (3)	C9—N1	1.480 (2)
C2—H2	0.9300	C9—H9A	0.9700
C3—C4	1.379 (3)	C9—H9B	0.9700
C3—H3	0.9300	N1—S1	1.6446 (13)
C4—C5	1.369 (3)	C10—S1	1.7555 (18)
C4—H4	0.9300	C10—H10A	0.9600
C5—C6	1.394 (2)	C10—H10B	0.9600
C5—H5	0.9300	C10—H10C	0.9600
C6—C7	1.515 (2)	O2—S1	1.4279 (13)
C7—C8	1.505 (3)	S1—O1	1.4227 (13)
C7—H7A	0.9700
C2—C1—C6	120.12 (15)	C9—C8—H8A	109.6
C2—C1—N1	120.16 (14)	C7—C8—H8B	109.6
C6—C1—N1	119.53 (13)	C9—C8—H8B	109.6
C3—C2—C1	120.02 (17)	H8A—C8—H8B	108.1
C3—C2—H2	120.0	N1—C9—C8	111.80 (14)
C1—C2—H2	120.0	N1—C9—H9A	109.3
C4—C3—C2	120.28 (18)	C8—C9—H9A	109.3
C4—C3—H3	119.9	N1—C9—H9B	109.3
C2—C3—H3	119.9	C8—C9—H9B	109.3
C5—C4—C3	119.56 (18)	H9A—C9—H9B	107.9
C5—C4—H4	120.2	C1—N1—C9	114.89 (12)
C3—C4—H4	120.2	C1—N1—S1	119.76 (10)
C4—C5—C6	122.06 (16)	C9—N1—S1	117.41 (10)
C4—C5—H5	119.0	S1—C10—H10A	109.5
C6—C5—H5	119.0	S1—C10—H10B	109.5
C5—C6—C1	117.87 (15)	H10A—C10—H10B	109.5
C5—C6—C7	119.39 (15)	S1—C10—H10C	109.5
C1—C6—C7	122.61 (15)	H10A—C10—H10C	109.5
C8—C7—C6	114.00 (14)	H10B—C10—H10C	109.5
C8—C7—H7A	108.8	O1—S1—O2	118.38 (10)
C6—C7—H7A	108.8	O1—S1—N1	106.54 (8)
C8—C7—H7B	108.8	O2—S1—N1	108.22 (7)
C6—C7—H7B	108.8	O1—S1—C10	108.39 (10)
H7A—C7—H7B	107.6	O2—S1—C10	107.06 (9)
C7—C8—C9	110.45 (15)	N1—S1—C10	107.85 (8)
C7—C8—H8A	109.6
C6—C1—C2—C3	3.1 (3)	C6—C1—N1—C9	22.44 (19)
N1—C1—C2—C3	178.13 (17)	C2—C1—N1—S1	59.22 (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—C6	1.2 (3)	C8—C9—N1—S1	97.83 (15)
C4—C5—C6—C1	0.9 (3)	C1—N1—S1—O1	−176.90 (12)
C4—C5—C6—C7	−174.89 (18)	C9—N1—S1—O1	35.68 (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—O1	35.68 (15)
C2—C1—C6—C7	172.62 (15)	C1—N1—S1—O2	−48.59 (13)
N1—C1—C6—C7	−2.4 (2)	C9—N1—S1—O2	163.98 (12)
C5—C6—C7—C8	−173.18 (16)	C1—N1—S1—O2	−48.59 (13)
C1—C6—C7—C8	11.2 (2)	C9—N1—S1—O2	163.98 (12)
C6—C7—C8—C9	−38.3 (2)	C1—N1—S1—C10	66.91 (14)
C7—C8—C9—N1	58.9 (2)	C9—N1—S1—C10	−80.52 (14)
C2—C1—N1—C9	−152.58 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···O2i	0.96	2.50	3.431 (2)	164

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C10H10CO2i	0.96	2.50	3.431(2)	164

Symmetry code: (i) .