N-Phenyl-adamantane-1-sulfinamide.

In the racemic title compound, C(16)H(21)NOS, the mol-ecules are packed into polymeric chains in the b-axis direction and are linked along the b axis by N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For literature on N-alkyl­alkanesulfinamides, see: Sato et al. (1975 ▶), Schuckmann et al. (1978 ▶); Ferreira et al. (2005 ▶). For related literature on cyclic N-aryl­alkanesulfinamides (sultims), see: Schulze et al. (2005 ▶). For the synthesis, see: Stretter et al. (1969 ▶). For related literature, see: Han et al. (2002 ▶); Weix & Ellman (2003 ▶).

Experimental

Crystal data

C16H21NOS

M = 275.40

Monoclinic,

a = 11.6614 (2) Å

b = 14.5582 (3) Å

c = 9.0632 (2) Å

β = 109.7770 (10)°

V = 1447.90 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 293 (2) K

0.12 × 0.08 × 0.06 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.975, T max = 0.987

14147 measured reflections

3563 independent reflections

2623 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.126

S = 1.07

3563 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019570/lx2059sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019570/lx2059Isup2.hkl

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

C16H21NOS	F000 = 592
Mr = 275.40	Dx = 1.263 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4542 reflections
a = 11.6614 (2) Å	θ = 2.3–18.3º
b = 14.5582 (3) Å	µ = 0.22 mm−1
c = 9.0632 (2) Å	T = 293 (2) K
β = 109.7770 (10)º	Block, white
V = 1447.90 (5) Å3	0.12 × 0.08 × 0.06 mm
Z = 4

Bruker APEXII diffractometer	3563 independent reflections
Radiation source: fine-focus sealed tube	2623 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
T = 293(2) K	θmax = 28.3º
ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.975, Tmax = 0.987	k = −18→19
14147 measured reflections	l = −12→12

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.0675P)2 + 0.1762P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
3563 reflections	Δρmax = 0.28 e Å−3
172 parameters	Δρmin = −0.30 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.58983 (13)	0.39058 (9)	0.82150 (16)	0.0364 (3)
C2	0.56242 (15)	0.48043 (11)	0.7296 (2)	0.0484 (4)
H2A	0.5187	0.5217	0.7757	0.058*
H2B	0.5117	0.4685	0.6219	0.058*
C3	0.68250 (16)	0.52473 (12)	0.7334 (2)	0.0580 (5)
H3	0.6652	0.5824	0.6741	0.070*
C4	0.76125 (18)	0.54460 (12)	0.9024 (3)	0.0638 (5)
H4A	0.8368	0.5736	0.9047	0.077*
H4B	0.7188	0.5863	0.9496	0.077*
C5	0.78874 (16)	0.45500 (12)	0.9943 (2)	0.0535 (4)
H5	0.8397	0.4677	1.1029	0.064*
C6	0.66905 (15)	0.41030 (12)	0.99233 (18)	0.0481 (4)
H6A	0.6261	0.4511	1.0403	0.058*
H6B	0.6861	0.3535	1.0517	0.058*
C7	0.74864 (17)	0.45997 (14)	0.6590 (2)	0.0619 (5)
H7A	0.8239	0.4881	0.6583	0.074*
H7B	0.6983	0.4476	0.5514	0.074*
C8	0.77682 (15)	0.37019 (13)	0.7515 (2)	0.0536 (4)
H8	0.8203	0.3288	0.7034	0.064*
C9	0.85636 (16)	0.38968 (13)	0.9200 (2)	0.0579 (4)
H9A	0.9326	0.4173	0.9220	0.069*
H9B	0.8748	0.3327	0.9789	0.069*
C10	0.65764 (15)	0.32443 (11)	0.7496 (2)	0.0473 (4)
H10A	0.6077	0.3099	0.6427	0.057*
H10B	0.6754	0.2678	0.8094	0.057*
S1	0.44633 (4)	0.34441 (3)	0.82885 (4)	0.04623 (15)
O1	0.47547 (12)	0.25339 (9)	0.90826 (15)	0.0702 (4)
N1	0.37398 (12)	0.32958 (9)	0.63941 (15)	0.0463 (3)
H1	0.4153	0.3178	0.5790	0.056*
C11	0.24605 (13)	0.33580 (9)	0.57455 (18)	0.0390 (3)
C12	0.18648 (15)	0.29240 (11)	0.4345 (2)	0.0499 (4)
H12	0.2305	0.2573	0.3866	0.060*
C13	0.06152 (17)	0.30068 (14)	0.3647 (2)	0.0657 (5)
H13	0.0223	0.2726	0.2687	0.079*
C14	−0.00505 (17)	0.35041 (14)	0.4370 (3)	0.0686 (6)
H14	−0.0893	0.3546	0.3917	0.082*
C15	0.05395 (17)	0.39325 (14)	0.5752 (3)	0.0654 (5)
H15	0.0094	0.4275	0.6235	0.078*
C16	0.17819 (16)	0.38689 (13)	0.6449 (2)	0.0542 (4)
H16	0.2169	0.4169	0.7393	0.065*

	U11	U22	U33	U12	U13	U23
C1	0.0339 (7)	0.0456 (7)	0.0304 (7)	0.0010 (6)	0.0117 (6)	0.0018 (6)
C2	0.0400 (8)	0.0553 (9)	0.0519 (9)	0.0083 (7)	0.0180 (7)	0.0142 (7)
C3	0.0517 (10)	0.0570 (10)	0.0698 (12)	0.0027 (8)	0.0264 (9)	0.0205 (9)
C4	0.0553 (11)	0.0540 (10)	0.0831 (14)	−0.0106 (8)	0.0248 (10)	−0.0099 (9)
C5	0.0447 (9)	0.0632 (10)	0.0455 (9)	−0.0046 (7)	0.0060 (8)	−0.0122 (8)
C6	0.0499 (10)	0.0593 (9)	0.0335 (8)	−0.0017 (7)	0.0121 (7)	−0.0036 (7)
C7	0.0453 (10)	0.0912 (13)	0.0554 (10)	−0.0031 (9)	0.0252 (9)	0.0080 (9)
C8	0.0359 (9)	0.0692 (10)	0.0574 (10)	0.0059 (7)	0.0180 (8)	−0.0127 (8)
C9	0.0376 (9)	0.0674 (11)	0.0607 (11)	0.0053 (8)	0.0061 (8)	−0.0033 (9)
C10	0.0412 (9)	0.0542 (9)	0.0446 (8)	0.0038 (7)	0.0121 (7)	−0.0094 (7)
S1	0.0400 (2)	0.0676 (3)	0.0334 (2)	−0.00510 (17)	0.01537 (18)	0.00352 (16)
O1	0.0590 (8)	0.0870 (9)	0.0588 (8)	−0.0153 (7)	0.0123 (7)	0.0304 (7)
N1	0.0355 (7)	0.0683 (9)	0.0359 (7)	0.0016 (6)	0.0133 (6)	−0.0037 (6)
C11	0.0358 (8)	0.0410 (7)	0.0413 (8)	0.0004 (6)	0.0142 (7)	0.0068 (6)
C12	0.0423 (9)	0.0498 (9)	0.0552 (10)	−0.0023 (7)	0.0131 (8)	−0.0067 (7)
C13	0.0449 (10)	0.0674 (11)	0.0719 (13)	−0.0087 (9)	0.0031 (9)	−0.0068 (10)
C14	0.0361 (10)	0.0729 (12)	0.0899 (16)	0.0032 (8)	0.0122 (11)	0.0168 (11)
C15	0.0509 (11)	0.0761 (12)	0.0751 (14)	0.0205 (9)	0.0292 (10)	0.0158 (10)
C16	0.0498 (10)	0.0646 (10)	0.0500 (10)	0.0118 (8)	0.0192 (8)	0.0012 (8)

C1—C10	1.525 (2)	C8—C10	1.536 (2)
C1—C2	1.526 (2)	C8—H8	0.980
C1—C6	1.538 (2)	C9—H9A	0.970
C1—S1	1.825 (2)	C9—H9B	0.970
C2—C3	1.531 (2)	C10—H10A	0.970
C2—H2A	0.970	C10—H10B	0.970
C2—H2B	0.970	S1—O1	1.491 (1)
C3—C7	1.513 (3)	S1—N1	1.651 (1)
C3—C4	1.523 (3)	N1—C11	1.409 (2)
C3—H3	0.980	N1—H1	0.860
C4—C5	1.522 (3)	C11—C12	1.377 (2)
C4—H4A	0.970	C11—C16	1.388 (2)
C4—H4B	0.970	C12—C13	1.384 (2)
C5—C9	1.530 (2)	C12—H12	0.930
C5—C6	1.535 (2)	C13—C14	1.378 (3)
C5—H5	0.980	C13—H13	0.930
C6—H6A	0.970	C14—C15	1.360 (3)
C6—H6B	0.970	C14—H14	0.930
C7—C8	1.527 (3)	C15—C16	1.374 (3)
C7—H7A	0.970	C15—H15	0.930
C7—H7B	0.970	C16—H16	0.930
C8—C9	1.521 (2)
C10—C1—C2	110.6 (1)	C9—C8—C7	109.7 (2)
C10—C1—C6	109.0 (1)	C9—C8—C10	109.5 (1)
C2—C1—C6	109.5 (1)	C7—C8—C10	109.8 (2)
C10—C1—S1	113.4 (1)	C9—C8—H8	109.3
C2—C1—S1	108.1 (1)	C7—C8—H8	109.3
C6—C1—S1	106.1 (1)	C10—C8—H8	109.3
C1—C2—C3	109.1 (1)	C8—C9—C5	109.2 (1)
C1—C2—H2A	109.9	C8—C9—H9A	109.9
C3—C2—H2A	109.9	C5—C9—H9A	109.9
C1—C2—H2B	109.9	C8—C9—H9B	109.9
C3—C2—H2B	109.9	C5—C9—H9B	109.9
H2A—C2—H2B	108.3	H9A—C9—H9B	108.3
C7—C3—C4	110.0 (2)	C1—C10—C8	108.6 (1)
C7—C3—C2	109.1 (2)	C1—C10—H10A	110.0
C4—C3—C2	109.8 (1)	C8—C10—H10A	110.0
C7—C3—H3	109.3	C1—C10—H10B	110.0
C4—C3—H3	109.3	C8—C10—H10B	110.0
C2—C3—H3	109.3	H10A—C10—H10B	108.3
C5—C4—C3	109.4 (1)	O1—S1—N1	109.79 (8)
C5—C4—H4A	109.8	O1—S1—C1	106.43 (7)
C3—C4—H4A	109.8	N1—S1—C1	99.34 (6)
C5—C4—H4B	109.8	C11—N1—S1	121.5 (1)
C3—C4—H4B	109.8	C11—N1—H1	119.3
H4A—C4—H4B	108.3	S1—N1—H1	119.3
C4—C5—C9	109.6 (2)	C12—C11—C16	118.7 (2)
C4—C5—C6	109.6 (1)	C12—C11—N1	119.2 (1)
C9—C5—C6	109.5 (1)	C16—C11—N1	122.0 (1)
C4—C5—H5	109.4	C11—C12—C13	120.4 (2)
C9—C5—H5	109.4	C11—C12—H12	119.8
C6—C5—H5	109.4	C13—C12—H12	119.8
C5—C6—C1	109.0 (1)	C14—C13—C12	120.3 (2)
C5—C6—H6A	109.9	C14—C13—H13	119.9
C1—C6—H6A	109.9	C12—C13—H13	119.9
C5—C6—H6B	109.9	C15—C14—C13	119.2 (2)
C1—C6—H6B	109.9	C15—C14—H14	120.4
H6A—C6—H6B	108.3	C13—C14—H14	120.4
C3—C7—C8	109.6 (1)	C14—C15—C16	121.3 (2)
C3—C7—H7A	109.7	C14—C15—H15	119.4
C8—C7—H7A	109.7	C16—C15—H15	119.4
C3—C7—H7B	109.7	C15—C16—C11	120.1 (2)
C8—C7—H7B	109.7	C15—C16—H16	120.0
H7A—C7—H7B	108.2	C11—C16—H16	120.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.17	2.988 (2)	160
C10—H10A···O1i	0.97	2.35	3.305 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.17	2.988 (2)	160
C10—H10A⋯O1i	0.97	2.35	3.305 (2)	168

Symmetry code: (i) .