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

In the title compound, C16H17NO2S, the heterocyclic ring adopts a half-chair conformation and the bond-angle sum at the N atom is 350.2°. The dihedral angle between the planes of the aromatic rings is 47.74 (10)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds to generate [010] chains.

Related literature

For reactions related to biotransformations, see: Leresche et al. (2006 ▶); Astudillo et al. (2009 ▶). For pharmacological activities, see: Bendale et al. (2007 ▶); Chen et al. (2007 ▶); Singer et al. (2005 ▶).

Experimental

Crystal data

C16H17NO2S

M = 287.37

Monoclinic,

a = 8.2176 (7) Å

b = 8.0468 (6) Å

c = 22.2439 (18) Å

β = 98.107 (4)°

V = 1456.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 94 K

0.24 × 0.22 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.949, T max = 0.961

20017 measured reflections

2568 independent reflections

2327 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.101

S = 1.09

2568 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.37 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: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814022181/hb7292sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814022181/hb7292Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814022181/hb7292Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814022181/hb7292fig1.tif

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

Click here for additional data file.

C . DOI: 10.1107/S1600536814022181/hb7292fig2.tif

The mol­ecular packing of the title compound, dashed lines indicate intra­molecular C—H⋯O and inter­molecular C—H⋯O hydrogen bonds forming C(6) chains viewed along [010].

CCDC reference: 1028050

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

C16H17NO2S	Prism
Mr = 287.37	Dx = 1.311 Mg m−3
Monoclinic, P21/n	Melting point: 402 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.2176 (7) Å	Cell parameters from 2327 reflections
b = 8.0468 (6) Å	θ = 1.9–25.0°
c = 22.2439 (18) Å	µ = 0.22 mm−1
β = 98.107 (4)°	T = 94 K
V = 1456.2 (2) Å3	Prism, colourless
Z = 4	0.24 × 0.22 × 0.18 mm
F(000) = 608

Bruker APEXII CCD diffractometer	2568 independent reflections
Radiation source: fine-focus sealed tube	2327 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
Detector resolution: 1.9 pixels mm-1	θmax = 25.0°, θmin = 1.9°
phi and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −9→9
Tmin = 0.949, Tmax = 0.961	l = −26→26
20017 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0362P)2 + 0.8395P] where P = (Fo2 + 2Fc2)/3
2568 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.37 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.

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	0.5482 (2)	0.4736 (2)	0.17137 (8)	0.0359 (4)
C2	0.5261 (3)	0.6396 (2)	0.15480 (9)	0.0461 (5)
H2	0.4386	0.7015	0.1675	0.055*
C3	0.6312 (3)	0.7140 (3)	0.12003 (10)	0.0565 (6)
H3	0.6146	0.8265	0.1078	0.068*
C4	0.7605 (3)	0.6253 (3)	0.10294 (10)	0.0593 (6)
H4	0.8319	0.6758	0.0782	0.071*
C5	0.7859 (2)	0.4634 (3)	0.12175 (9)	0.0509 (5)
H5	0.8772	0.4043	0.1106	0.061*
C6	0.6818 (2)	0.3838 (2)	0.15666 (8)	0.0400 (4)
C7	0.7232 (3)	0.2110 (3)	0.18038 (11)	0.0553 (6)
H7A	0.7451	0.1398	0.1461	0.066*
H7B	0.8255	0.2161	0.2098	0.066*
C8	0.5908 (3)	0.1313 (3)	0.21082 (11)	0.0553 (6)
H8A	0.6394	0.0426	0.2386	0.066*
H8B	0.5079	0.0799	0.1798	0.066*
C9	0.5085 (3)	0.2589 (3)	0.24637 (9)	0.0505 (5)
H9A	0.4200	0.2043	0.2651	0.061*
H9B	0.5900	0.3033	0.2795	0.061*
C10	0.2228 (2)	0.2132 (2)	0.12881 (8)	0.0368 (4)
C11	0.2794 (3)	0.2300 (3)	0.07339 (9)	0.0536 (5)
H11	0.3210	0.3333	0.0616	0.064*
C12	0.2741 (4)	0.0936 (3)	0.03583 (10)	0.0661 (7)
H12	0.3131	0.1040	−0.0022	0.079*
C13	0.2137 (3)	−0.0582 (3)	0.05179 (10)	0.0577 (6)
C14	0.1579 (3)	−0.0714 (3)	0.10703 (10)	0.0524 (5)
H14	0.1156	−0.1745	0.1187	0.063*
C15	0.1626 (2)	0.0630 (2)	0.14573 (9)	0.0427 (4)
H15	0.1244	0.0520	0.1839	0.051*
C16	0.2090 (4)	−0.2057 (4)	0.00972 (13)	0.0920 (10)
H16A	0.2151	−0.3085	0.0336	0.138*
H16B	0.3025	−0.2004	−0.0131	0.138*
H16C	0.1062	−0.2042	−0.0186	0.138*
O1	0.15775 (18)	0.33842 (19)	0.22946 (7)	0.0548 (4)
O2	0.19664 (17)	0.52807 (17)	0.14578 (7)	0.0532 (4)
N	0.43800 (18)	0.39748 (19)	0.20781 (7)	0.0381 (4)
S	0.24138 (5)	0.38103 (6)	0.17987 (2)	0.03916 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0337 (9)	0.0389 (10)	0.0349 (9)	−0.0051 (8)	0.0038 (7)	−0.0037 (8)
C2	0.0459 (11)	0.0401 (11)	0.0527 (11)	−0.0041 (9)	0.0082 (9)	−0.0020 (9)
C3	0.0605 (14)	0.0486 (12)	0.0607 (13)	−0.0124 (11)	0.0102 (11)	0.0080 (10)
C4	0.0523 (13)	0.0752 (16)	0.0527 (12)	−0.0209 (12)	0.0152 (10)	0.0045 (12)
C5	0.0367 (11)	0.0699 (15)	0.0470 (11)	−0.0057 (10)	0.0092 (9)	−0.0098 (11)
C6	0.0341 (10)	0.0479 (11)	0.0373 (9)	−0.0024 (8)	0.0025 (8)	−0.0061 (8)
C7	0.0451 (12)	0.0545 (13)	0.0660 (14)	0.0119 (10)	0.0070 (10)	−0.0018 (11)
C8	0.0496 (12)	0.0458 (12)	0.0689 (14)	0.0112 (10)	0.0029 (10)	0.0139 (10)
C9	0.0495 (12)	0.0565 (13)	0.0457 (11)	0.0021 (10)	0.0074 (9)	0.0137 (10)
C10	0.0365 (10)	0.0350 (10)	0.0381 (9)	0.0010 (8)	0.0028 (7)	0.0014 (8)
C11	0.0704 (15)	0.0471 (12)	0.0444 (11)	−0.0039 (11)	0.0118 (10)	0.0067 (9)
C12	0.0952 (19)	0.0675 (16)	0.0370 (11)	0.0029 (14)	0.0138 (12)	−0.0015 (11)
C13	0.0697 (15)	0.0497 (13)	0.0498 (12)	0.0089 (11)	−0.0056 (11)	−0.0092 (10)
C14	0.0595 (13)	0.0374 (11)	0.0578 (13)	−0.0024 (10)	−0.0002 (10)	0.0005 (9)
C15	0.0454 (11)	0.0390 (10)	0.0439 (10)	−0.0020 (8)	0.0066 (9)	0.0028 (8)
C16	0.127 (3)	0.0716 (19)	0.0739 (18)	0.0083 (18)	0.0008 (18)	−0.0298 (15)
O1	0.0478 (8)	0.0610 (9)	0.0612 (9)	−0.0083 (7)	0.0268 (7)	−0.0128 (7)
O2	0.0399 (8)	0.0352 (7)	0.0831 (11)	0.0066 (6)	0.0040 (7)	0.0050 (7)
N	0.0361 (8)	0.0379 (8)	0.0410 (8)	−0.0006 (7)	0.0084 (7)	0.0007 (7)
S	0.0332 (3)	0.0345 (3)	0.0516 (3)	0.00026 (18)	0.0119 (2)	−0.0035 (2)

C1—C2	1.390 (3)	C10—C15	1.378 (3)
C1—C6	1.392 (3)	C10—C11	1.384 (3)
C1—N	1.435 (2)	C10—S	1.7577 (19)
C2—C3	1.375 (3)	C11—C12	1.377 (3)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.377 (3)	C12—C13	1.384 (3)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.375 (3)	C13—C14	1.374 (3)
C4—H4	0.9500	C13—C16	1.508 (3)
C5—C6	1.390 (3)	C14—C15	1.379 (3)
C5—H5	0.9500	C14—H14	0.9500
C6—C7	1.509 (3)	C15—H15	0.9500
C7—C8	1.504 (3)	C16—H16A	0.9800
C7—H7A	0.9900	C16—H16B	0.9800
C7—H7B	0.9900	C16—H16C	0.9800
C8—C9	1.512 (3)	O1—S	1.4213 (14)
C8—H8A	0.9900	O2—S	1.4254 (14)
C8—H8B	0.9900	N—S	1.6526 (16)
C9—N	1.475 (2)	S—O1	1.4213 (14)
C9—H9A	0.9900	S—O2	1.4254 (14)
C9—H9B	0.9900
C2—C1—C6	120.95 (17)	H9A—C9—H9B	107.9
C2—C1—N	119.39 (17)	C15—C10—C11	120.52 (18)
C6—C1—N	119.52 (17)	C15—C10—S	119.94 (14)
C3—C2—C1	119.9 (2)	C11—C10—S	119.40 (15)
C3—C2—H2	120.1	C12—C11—C10	118.5 (2)
C1—C2—H2	120.1	C12—C11—H11	120.8
C2—C3—C4	120.0 (2)	C10—C11—H11	120.8
C2—C3—H3	120.0	C11—C12—C13	122.0 (2)
C4—C3—H3	120.0	C11—C12—H12	119.0
C5—C4—C3	119.8 (2)	C13—C12—H12	119.0
C5—C4—H4	120.1	C14—C13—C12	118.3 (2)
C3—C4—H4	120.1	C14—C13—C16	120.8 (2)
C4—C5—C6	121.8 (2)	C12—C13—C16	120.9 (2)
C4—C5—H5	119.1	C13—C14—C15	121.0 (2)
C6—C5—H5	119.1	C13—C14—H14	119.5
C5—C6—C1	117.40 (19)	C15—C14—H14	119.5
C5—C6—C7	119.59 (18)	C10—C15—C14	119.75 (19)
C1—C6—C7	122.88 (17)	C10—C15—H15	120.1
C8—C7—C6	114.12 (17)	C14—C15—H15	120.1
C8—C7—H7A	108.7	C13—C16—H16A	109.5
C6—C7—H7A	108.7	C13—C16—H16B	109.5
C8—C7—H7B	108.7	H16A—C16—H16B	109.5
C6—C7—H7B	108.7	C13—C16—H16C	109.5
H7A—C7—H7B	107.6	H16A—C16—H16C	109.5
C7—C8—C9	110.59 (19)	H16B—C16—H16C	109.5
C7—C8—H8A	109.5	C1—N—C9	115.09 (15)
C9—C8—H8A	109.5	C1—N—S	118.90 (12)
C7—C8—H8B	109.5	C9—N—S	116.17 (13)
C9—C8—H8B	109.5	O1—S—O2	119.76 (9)
H8A—C8—H8B	108.1	O1—S—N	106.36 (9)
N—C9—C8	112.16 (16)	O2—S—N	107.38 (8)
N—C9—H9A	109.2	O1—S—C10	107.98 (9)
C8—C9—H9A	109.2	O2—S—C10	107.57 (9)
N—C9—H9B	109.2	N—S—C10	107.19 (8)
C8—C9—H9B	109.2

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2i	0.95	2.53	3.340 (2)	143

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C14H14O2i	0.95	2.53	3.340(2)	143

Symmetry code: (i) .