N-[2-(Phenyl-sulfon-yl)eth-yl]benzyl-amine.

The title compound, C(15)H(17)NO(2)S, exhibits intra-molecular hydrogen bonding between the amine H atom and a sulfonyl O atom. The conformation of the mol-ecule is described by the four PhCH(2)-NH-CH(2)-CH(2)-SO(2)Ph torsion angles of 79.6 (2), -166.21 (14), -70.29 (17) and -58.93 (13)°.

Related literature

For the synthesis, see: Bandini et al. (2008 ▶). For reactions of benzyl­amine and vinyl­sulfonyl­benzene, see: Makosza et al. (2008 ▶); Ni et al. (2003 ▶). For the determination of absolute structure from Bijvoet pairs, see: Hooft et al. (2008 ▶). For inter­molecular inter­actions, see: Steiner (1996 ▶).

Experimental

Crystal data

C15H17NO2S

M = 275.36

Monoclinic,

a = 5.7428 (11) Å

b = 10.170 (2) Å

c = 12.486 (2) Å

β = 102.09 (3)°

V = 713.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 298 K

0.50 × 0.45 × 0.32 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.896, T max = 0.932

5320 measured reflections

3264 independent reflections

2990 reflections with I > 2σ(I)

R int = 0.021

3 standard reflections every 60 min intensity decay: 4.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.086

S = 0.99

3264 reflections

177 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 2081 Bijvoet pairs

Flack parameter: 0.07 (6)

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Farrugia, 1999 ▶); program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203886X/bg2477sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203886X/bg2477Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203886X/bg2477Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H17NO2S	F(000) = 292
Mr = 275.36	Dx = 1.282 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 5.7428 (11) Å	θ = 2.6–27.5°
b = 10.170 (2) Å	µ = 0.22 mm−1
c = 12.486 (2) Å	T = 298 K
β = 102.09 (3)°	Prism, colorless
V = 713.1 (2) Å3	0.50 × 0.45 × 0.32 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	2990 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 27.5°, θmin = 2.6°
θ/2θ scans	h = −7→7
Absorption correction: ψ scan (North et al., 1968)	k = −13→13
Tmin = 0.896, Tmax = 0.932	l = −16→16
5320 measured reflections	3 standard reflections every 60 min
3264 independent reflections	intensity decay: 4.0%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.0562P)2 + 0.0525P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
3264 reflections	Δρmax = 0.15 e Å−3
177 parameters	Δρmin = −0.22 e Å−3
1 restraint	Absolute structure: Flack (1983), 2081 Bijvoet pairs
0 constraints	Flack parameter: 0.07 (6)
Primary atom site location: structure-invariant direct methods

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
C1	0.1957 (3)	0.01813 (15)	0.34724 (12)	0.0424 (3)
C2	0.0482 (3)	−0.08893 (17)	0.34717 (13)	0.0533 (4)
H2	−0.0657	−0.0884	0.3903	0.064*
C3	0.0698 (4)	−0.1963 (2)	0.28342 (15)	0.0657 (5)
H3	−0.0305	−0.2682	0.2826	0.079*
C4	0.2404 (4)	−0.1973 (2)	0.22054 (14)	0.0639 (5)
H4	0.254	−0.2699	0.177	0.077*
C5	0.3912 (4)	−0.0917 (2)	0.22157 (15)	0.0656 (5)
H5	0.5078	−0.094	0.1799	0.079*
C6	0.3693 (3)	0.01759 (19)	0.28437 (14)	0.0561 (4)
H6	0.469	0.0897	0.2847	0.067*
C7	0.4077 (2)	0.1536 (2)	0.53880 (12)	0.0522 (3)
H7A	0.5518	0.1629	0.5105	0.063*
H7B	0.3977	0.2293	0.5848	0.063*
C8	0.4311 (3)	0.03164 (18)	0.60956 (14)	0.0560 (4)
H8A	0.4215	−0.0452	0.5628	0.067*
H8B	0.587	0.0316	0.658	0.067*
C9	0.3093 (4)	−0.0788 (2)	0.76111 (17)	0.0691 (5)
H9A	0.374	−0.1558	0.732	0.083*
H9B	0.1651	−0.1049	0.7843	0.083*
C10	0.4876 (3)	−0.02798 (17)	0.85863 (14)	0.0554 (4)
C11	0.7095 (4)	−0.0864 (2)	0.88806 (17)	0.0698 (5)
H11	0.7488	−0.156	0.8469	0.084*
C12	0.8722 (4)	−0.0421 (3)	0.97776 (19)	0.0892 (8)
H12	1.021	−0.0819	0.9964	0.107*
C13	0.8185 (5)	0.0584 (3)	1.03905 (17)	0.0914 (8)
H13	0.9293	0.0868	1.1	0.11*
C14	0.6002 (5)	0.1187 (3)	1.01140 (17)	0.0836 (7)
H14	0.5637	0.1887	1.0529	0.1*
C15	0.4339 (4)	0.0746 (2)	0.92103 (16)	0.0670 (5)
H15	0.2854	0.1147	0.9027	0.08*
N1	0.2511 (3)	0.02105 (18)	0.67505 (12)	0.0610 (4)
H1	0.122 (4)	−0.001 (2)	0.6295 (17)	0.059 (5)*
O1	−0.05605 (19)	0.13963 (16)	0.46634 (10)	0.0646 (4)
O2	0.1828 (3)	0.27332 (14)	0.36372 (13)	0.0725 (4)
S1	0.16006 (6)	0.15714 (4)	0.42668 (3)	0.04876 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0372 (7)	0.0472 (8)	0.0405 (6)	0.0003 (6)	0.0032 (5)	0.0037 (6)
C2	0.0498 (8)	0.0577 (9)	0.0529 (8)	−0.0103 (7)	0.0121 (7)	0.0007 (7)
C3	0.0720 (11)	0.0584 (10)	0.0625 (10)	−0.0135 (9)	0.0046 (9)	−0.0038 (8)
C4	0.0772 (12)	0.0615 (10)	0.0479 (8)	0.0123 (9)	0.0017 (8)	−0.0040 (8)
C5	0.0635 (10)	0.0825 (13)	0.0540 (9)	0.0153 (10)	0.0195 (8)	0.0043 (9)
C6	0.0481 (8)	0.0630 (10)	0.0598 (9)	−0.0047 (7)	0.0170 (7)	0.0065 (8)
C7	0.0383 (6)	0.0595 (8)	0.0546 (7)	0.0006 (9)	0.0004 (5)	−0.0105 (9)
C8	0.0480 (8)	0.0631 (10)	0.0521 (8)	0.0157 (7)	−0.0006 (7)	−0.0062 (7)
C9	0.0672 (11)	0.0664 (11)	0.0689 (11)	−0.0122 (9)	0.0035 (9)	0.0035 (9)
C10	0.0537 (9)	0.0578 (9)	0.0535 (8)	−0.0053 (7)	0.0082 (7)	0.0125 (7)
C11	0.0607 (10)	0.0811 (13)	0.0670 (11)	0.0066 (10)	0.0123 (9)	0.0108 (10)
C12	0.0620 (12)	0.129 (2)	0.0703 (13)	0.0054 (13)	0.0007 (10)	0.0235 (15)
C13	0.0837 (16)	0.133 (2)	0.0498 (10)	−0.0307 (16)	−0.0048 (10)	0.0129 (13)
C14	0.1094 (19)	0.0896 (16)	0.0552 (10)	−0.0127 (13)	0.0251 (11)	−0.0065 (10)
C15	0.0675 (12)	0.0706 (12)	0.0636 (10)	0.0038 (9)	0.0152 (9)	0.0075 (9)
N1	0.0474 (8)	0.0746 (10)	0.0560 (8)	0.0048 (7)	−0.0005 (6)	−0.0003 (7)
O1	0.0386 (5)	0.0823 (10)	0.0720 (7)	0.0089 (6)	0.0094 (5)	−0.0116 (7)
O2	0.0716 (9)	0.0513 (7)	0.0871 (9)	0.0056 (6)	−0.0010 (7)	0.0134 (7)
S1	0.03744 (16)	0.04880 (18)	0.05641 (19)	0.00474 (16)	0.00158 (12)	0.00009 (18)

C1—C2	1.379 (2)	C9—N1	1.465 (3)
C1—C6	1.392 (2)	C9—C10	1.508 (3)
C1—S1	1.7634 (16)	C9—H9A	0.97
C2—C3	1.372 (3)	C9—H9B	0.97
C2—H2	0.93	C10—C15	1.375 (3)
C3—C4	1.378 (3)	C10—C11	1.384 (3)
C3—H3	0.93	C11—C12	1.376 (3)
C4—C5	1.378 (3)	C11—H11	0.93
C4—H4	0.93	C12—C13	1.351 (4)
C5—C6	1.381 (3)	C12—H12	0.93
C5—H5	0.93	C13—C14	1.373 (4)
C6—H6	0.93	C13—H13	0.93
C7—C8	1.512 (3)	C14—C15	1.391 (3)
C7—S1	1.7748 (15)	C14—H14	0.93
C7—H7A	0.97	C15—H15	0.93
C7—H7B	0.97	N1—H1	0.87 (2)
C8—N1	1.450 (2)	O1—S1	1.4404 (12)
C8—H8A	0.97	O2—S1	1.4402 (15)
C8—H8B	0.97
C2—C1—C6	120.57 (16)	C10—C9—H9A	109.3
C2—C1—S1	119.32 (12)	N1—C9—H9B	109.3
C6—C1—S1	120.10 (13)	C10—C9—H9B	109.3
C3—C2—C1	119.89 (16)	H9A—C9—H9B	108
C3—C2—H2	120.1	C15—C10—C11	118.58 (19)
C1—C2—H2	120.1	C15—C10—C9	121.49 (18)
C2—C3—C4	119.87 (18)	C11—C10—C9	119.93 (19)
C2—C3—H3	120.1	C12—C11—C10	120.4 (2)
C4—C3—H3	120.1	C12—C11—H11	119.8
C5—C4—C3	120.62 (18)	C10—C11—H11	119.8
C5—C4—H4	119.7	C13—C12—C11	120.8 (2)
C3—C4—H4	119.7	C13—C12—H12	119.6
C4—C5—C6	120.05 (17)	C11—C12—H12	119.6
C4—C5—H5	120	C12—C13—C14	120.0 (2)
C6—C5—H5	120	C12—C13—H13	120
C5—C6—C1	118.99 (16)	C14—C13—H13	120
C5—C6—H6	120.5	C13—C14—C15	119.7 (2)
C1—C6—H6	120.5	C13—C14—H14	120.2
C8—C7—S1	115.86 (13)	C15—C14—H14	120.2
C8—C7—H7A	108.3	C10—C15—C14	120.5 (2)
S1—C7—H7A	108.3	C10—C15—H15	119.8
C8—C7—H7B	108.3	C14—C15—H15	119.8
S1—C7—H7B	108.3	C8—N1—C9	112.65 (15)
H7A—C7—H7B	107.4	C8—N1—H1	105.3 (13)
N1—C8—C7	113.80 (13)	C9—N1—H1	109.5 (14)
N1—C8—H8A	108.8	O2—S1—O1	118.19 (9)
C7—C8—H8A	108.8	O2—S1—C1	108.44 (8)
N1—C8—H8B	108.8	O1—S1—C1	107.70 (8)
C7—C8—H8B	108.8	O2—S1—C7	107.33 (10)
H8A—C8—H8B	107.7	O1—S1—C7	109.39 (8)
N1—C9—C10	111.51 (16)	C1—S1—C7	105.02 (8)
N1—C9—H9A	109.3
C6—C1—C2—C3	−1.0 (3)	C12—C13—C14—C15	0.9 (4)
S1—C1—C2—C3	178.24 (14)	C11—C10—C15—C14	0.3 (3)
C1—C2—C3—C4	0.7 (3)	C9—C10—C15—C14	179.22 (18)
C2—C3—C4—C5	0.5 (3)	C13—C14—C15—C10	−0.7 (3)
C3—C4—C5—C6	−1.2 (3)	C7—C8—N1—C9	−166.21 (14)
C4—C5—C6—C1	0.9 (3)	C10—C9—N1—C8	79.6 (2)
C2—C1—C6—C5	0.2 (2)	C2—C1—S1—O2	−138.39 (14)
S1—C1—C6—C5	−179.02 (13)	C6—C1—S1—O2	40.86 (14)
S1—C7—C8—N1	−70.29 (17)	C2—C1—S1—O1	−9.40 (15)
N1—C9—C10—C15	64.2 (2)	C6—C1—S1—O1	169.85 (13)
N1—C9—C10—C11	−116.9 (2)	C2—C1—S1—C7	107.12 (14)
C15—C10—C11—C12	−0.1 (3)	C6—C1—S1—C7	−73.64 (14)
C9—C10—C11—C12	−179.06 (19)	C8—C7—S1—O2	−174.19 (12)
C10—C11—C12—C13	0.4 (4)	C8—C7—S1—O1	56.42 (15)
C11—C12—C13—C14	−0.7 (4)	C8—C7—S1—C1	−58.93 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.87 (2)	2.52 (2)	3.071 (2)	121.9 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.87 (2)	2.52 (2)	3.071 (2)	121.9 (17)