Crystal structure of 1-benzyl-sulfonyl-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 354.6°. The dihedral angle between the planes of the aromatic rings is 74.15 (10)°. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, generating C(8) and C(4) chains propagating along [100] and [010], respectively, which together generate (001) sheets.

Related literature

For the biological properties of 1,2,3,4-tetra­hydro­quinoline derivatives, see: Bendale et al. (2007 ▸); Singer et al. (2005 ▸). For related structures, see: Jeyaseelan et al. (2014 ▸, 2015 ▸).

Experimental

Crystal data

C16H17NO2S

M = 287.36

Monoclinic,

a = 13.5690 (5) Å

b = 6.7128 (2) Å

c = 16.8317 (6) Å

β = 110.243 (1)°

V = 1438.44 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 295 K

0.24 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.947, T max = 0.960

19601 measured reflections

2529 independent reflections

2264 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.101

S = 1.08

2529 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.38 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, 2015 ▸); molecular graphics: Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL2014.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015004727/hb7377sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015004727/hb7377Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015004727/hb7377Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015004727/hb7377fig1.tif

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

Click here for additional data file.

ab . DOI: 10.1107/S2056989015004727/hb7377fig2.tif

The mol­ecular packing of the title compound, dashed lines indicates the C—H⋯O weak hydrogen bonds in the ab plane.

CCDC reference: 1052632

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

C16H17NO2S	Prism
Mr = 287.36	Dx = 1.327 Mg m−3
Monoclinic, P21/n	Melting point: 514 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 13.5690 (5) Å	Cell parameters from 2529 reflections
b = 6.7128 (2) Å	θ = 1.7–25°
c = 16.8317 (6) Å	µ = 0.23 mm−1
β = 110.243 (1)°	T = 295 K
V = 1438.44 (9) Å3	Prism, colourless
Z = 4	0.24 × 0.20 × 0.18 mm
F(000) = 608

Bruker APEXII CCD diffractometer	2529 independent reflections
Radiation source: fine-focus sealed tube	2264 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
Detector resolution: 1.90 pixels mm-1	θmax = 25.0°, θmin = 1.7°
phi and ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −7→7
Tmin = 0.947, Tmax = 0.960	l = −19→20
19601 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0563P)2 + 0.3073P] where P = (Fo2 + 2Fc2)/3
2529 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.38 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
S1	0.36706 (3)	0.52581 (6)	0.20696 (2)	0.04077 (16)
N1	0.47088 (9)	0.40403 (18)	0.20485 (8)	0.0377 (3)
O1	0.37882 (9)	0.73063 (17)	0.18920 (8)	0.0515 (3)
C11	0.47391 (11)	0.5739 (2)	0.37732 (10)	0.0395 (4)
C1	0.60202 (12)	0.6674 (2)	0.22242 (10)	0.0419 (4)
H1	0.5827	0.7225	0.2656	0.050*
O2	0.27373 (9)	0.4236 (2)	0.15618 (8)	0.0634 (4)
C6	0.55139 (11)	0.4980 (2)	0.18039 (9)	0.0334 (3)
C12	0.55291 (13)	0.4389 (3)	0.41491 (11)	0.0488 (4)
H12	0.5430	0.3051	0.3999	0.059*
C5	0.58183 (13)	0.4084 (2)	0.11812 (10)	0.0448 (4)
C10	0.37241 (13)	0.5045 (3)	0.31416 (11)	0.0477 (4)
H10A	0.3155	0.5818	0.3211	0.057*
H10B	0.3615	0.3662	0.3257	0.057*
C9	0.46039 (15)	0.1865 (2)	0.19022 (11)	0.0516 (4)
H9A	0.4017	0.1368	0.2047	0.062*
H9B	0.5236	0.1200	0.2260	0.062*
C16	0.49091 (15)	0.7733 (3)	0.40037 (12)	0.0547 (4)
H16	0.4387	0.8669	0.3758	0.066*
C2	0.68073 (13)	0.7538 (3)	0.20020 (13)	0.0555 (5)
H2	0.7137	0.8689	0.2275	0.067*
C3	0.71051 (15)	0.6695 (3)	0.13749 (14)	0.0679 (6)
H3	0.7633	0.7280	0.1221	0.081*
C13	0.64626 (15)	0.4993 (3)	0.47439 (12)	0.0632 (5)
H13	0.6984	0.4061	0.4996	0.076*
C14	0.66280 (15)	0.6951 (4)	0.49666 (12)	0.0646 (6)
H14	0.7262	0.7354	0.5366	0.078*
C7	0.53441 (17)	0.2149 (3)	0.07532 (12)	0.0625 (5)
H7A	0.5113	0.2333	0.0145	0.075*
H7B	0.5885	0.1131	0.0903	0.075*
C4	0.66236 (16)	0.4995 (3)	0.09785 (14)	0.0634 (5)
H4	0.6840	0.4431	0.0562	0.076*
C8	0.44285 (18)	0.1420 (3)	0.09850 (13)	0.0667 (6)
H8A	0.4346	−0.0005	0.0888	0.080*
H8B	0.3789	0.2067	0.0629	0.080*
C15	0.58539 (18)	0.8325 (3)	0.45973 (13)	0.0654 (5)
H15	0.5966	0.9662	0.4747	0.079*

	U11	U22	U33	U12	U13	U23
S1	0.0284 (2)	0.0475 (3)	0.0419 (3)	−0.00260 (14)	0.00645 (17)	0.00823 (16)
N1	0.0394 (7)	0.0304 (6)	0.0437 (7)	−0.0068 (5)	0.0147 (5)	−0.0008 (5)
O1	0.0455 (7)	0.0438 (7)	0.0627 (7)	0.0085 (5)	0.0155 (6)	0.0154 (5)
C11	0.0358 (8)	0.0506 (9)	0.0373 (8)	0.0036 (7)	0.0193 (6)	0.0022 (7)
C1	0.0376 (8)	0.0386 (8)	0.0478 (9)	−0.0041 (6)	0.0127 (7)	−0.0021 (7)
O2	0.0352 (6)	0.0850 (9)	0.0578 (8)	−0.0170 (6)	0.0004 (5)	0.0074 (7)
C6	0.0308 (7)	0.0326 (7)	0.0349 (8)	−0.0002 (5)	0.0088 (6)	0.0035 (6)
C12	0.0503 (10)	0.0531 (10)	0.0431 (9)	0.0111 (8)	0.0165 (8)	−0.0011 (7)
C5	0.0502 (9)	0.0451 (9)	0.0392 (8)	0.0065 (7)	0.0157 (7)	0.0047 (7)
C10	0.0347 (8)	0.0621 (10)	0.0496 (10)	0.0006 (7)	0.0187 (7)	0.0069 (8)
C9	0.0659 (11)	0.0311 (8)	0.0573 (10)	−0.0103 (7)	0.0205 (9)	0.0010 (7)
C16	0.0605 (11)	0.0515 (10)	0.0575 (11)	0.0093 (8)	0.0272 (9)	0.0028 (8)
C2	0.0405 (9)	0.0500 (10)	0.0697 (12)	−0.0115 (7)	0.0108 (8)	0.0085 (9)
C3	0.0477 (10)	0.0809 (14)	0.0836 (14)	−0.0053 (10)	0.0336 (10)	0.0238 (12)
C13	0.0463 (10)	0.0953 (16)	0.0442 (10)	0.0197 (10)	0.0107 (8)	0.0000 (10)
C14	0.0509 (10)	0.1025 (17)	0.0424 (10)	−0.0162 (11)	0.0185 (8)	−0.0123 (10)
C7	0.0889 (14)	0.0505 (10)	0.0481 (10)	0.0043 (10)	0.0236 (10)	−0.0111 (8)
C4	0.0630 (12)	0.0794 (14)	0.0605 (12)	0.0072 (10)	0.0375 (10)	0.0079 (10)
C8	0.0895 (15)	0.0432 (10)	0.0611 (12)	−0.0192 (10)	0.0180 (10)	−0.0149 (9)
C15	0.0842 (14)	0.0607 (12)	0.0607 (12)	−0.0209 (11)	0.0368 (11)	−0.0156 (10)

S1—O1	1.4277 (12)	C9—H9A	0.9700
S1—O2	1.4341 (12)	C9—H9B	0.9700
S1—N1	1.6397 (13)	C16—C15	1.383 (3)
S1—C10	1.7863 (18)	C16—H16	0.9300
N1—C6	1.4397 (18)	C2—C3	1.376 (3)
N1—C9	1.4794 (19)	C2—H2	0.9300
C11—C12	1.379 (2)	C3—C4	1.368 (3)
C11—C16	1.390 (2)	C3—H3	0.9300
C11—C10	1.494 (2)	C13—C14	1.364 (3)
C1—C2	1.376 (2)	C13—H13	0.9300
C1—C6	1.389 (2)	C14—C15	1.374 (3)
C1—H1	0.9300	C14—H14	0.9300
C6—C5	1.389 (2)	C7—C8	1.507 (3)
C12—C13	1.376 (3)	C7—H7A	0.9700
C12—H12	0.9300	C7—H7B	0.9700
C5—C4	1.394 (3)	C4—H4	0.9300
C5—C7	1.517 (2)	C8—H8A	0.9700
C10—H10A	0.9700	C8—H8B	0.9700
C10—H10B	0.9700	C15—H15	0.9300
C9—C8	1.508 (3)
O1—S1—O2	118.41 (8)	H9A—C9—H9B	108.2
O1—S1—N1	108.44 (7)	C15—C16—C11	120.08 (18)
O2—S1—N1	109.67 (8)	C15—C16—H16	120.0
O1—S1—C10	108.68 (8)	C11—C16—H16	120.0
O2—S1—C10	106.42 (8)	C1—C2—C3	119.78 (17)
N1—S1—C10	104.30 (7)	C1—C2—H2	120.1
C6—N1—C9	115.08 (12)	C3—C2—H2	120.1
C6—N1—S1	122.03 (10)	C4—C3—C2	119.99 (17)
C9—N1—S1	117.50 (10)	C4—C3—H3	120.0
C12—C11—C16	118.48 (16)	C2—C3—H3	120.0
C12—C11—C10	120.05 (15)	C14—C13—C12	120.44 (18)
C16—C11—C10	121.46 (15)	C14—C13—H13	119.8
C2—C1—C6	120.02 (16)	C12—C13—H13	119.8
C2—C1—H1	120.0	C13—C14—C15	119.68 (18)
C6—C1—H1	120.0	C13—C14—H14	120.2
C1—C6—C5	120.99 (14)	C15—C14—H14	120.2
C1—C6—N1	120.25 (13)	C8—C7—C5	114.05 (15)
C5—C6—N1	118.62 (13)	C8—C7—H7A	108.7
C13—C12—C11	120.92 (17)	C5—C7—H7A	108.7
C13—C12—H12	119.5	C8—C7—H7B	108.7
C11—C12—H12	119.5	C5—C7—H7B	108.7
C6—C5—C4	117.24 (16)	H7A—C7—H7B	107.6
C6—C5—C7	122.76 (15)	C3—C4—C5	121.93 (18)
C4—C5—C7	119.95 (16)	C3—C4—H4	119.0
C11—C10—S1	113.53 (11)	C5—C4—H4	119.0
C11—C10—H10A	108.9	C7—C8—C9	110.39 (15)
S1—C10—H10A	108.9	C7—C8—H8A	109.6
C11—C10—H10B	108.9	C9—C8—H8A	109.6
S1—C10—H10B	108.9	C7—C8—H8B	109.6
H10A—C10—H10B	107.7	C9—C8—H8B	109.6
N1—C9—C8	109.76 (14)	H8A—C8—H8B	108.1
N1—C9—H9A	109.7	C14—C15—C16	120.39 (19)
C8—C9—H9A	109.7	C14—C15—H15	119.8
N1—C9—H9B	109.7	C16—C15—H15	119.8
C8—C9—H9B	109.7

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1i	0.93	2.69	3.573 (2)	158
C10—H10A···O2ii	0.97	2.68	3.575 (2)	153

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C14H14O1i	0.93	2.69	3.573(2)	158
C10H10AO2ii	0.97	2.68	3.575(2)	153

Symmetry codes: (i) ; (ii) .