N-Phenyl­adamantane-1-sulfinamide

Datta, M.; Buglass, A.J.; Hong, C.S.; Lim, J.H.

doi:10.1107/S1600536808019570

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1393

doi:10.1107/S1600536808019570

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N-Phenyladamantane-1-sulfinamide

Mrityunjoy Datta,^a Alan J Buglass,^a ^* Chang Seop Hong ^b and Jeon Hak Lim ^b

^aDepartment of Chemistry, Korea Advanced Institute of Science and Technology, Daejeon 305-701, Republic of Korea, and ^bDepartment of Chemistry, Korea University, Seoul 136-701, Republic of Korea
^*Correspondence e-mail: ajbuglass@kaist.ac.kr

(Received 11 June 2008; accepted 27 June 2008; online 5 July 2008)

In the racemic title compound, C₁₆H₂₁NOS, the molecules 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_r = 275.40
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.126
S = 1.07
3563 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

The title compound (I) was prepared from aniline and 1-adamantanesulfinyl chloride, which was itself prepared from adamantane and thionyl chloride in the presence of anhydrous AlCl₃ (Stretter et al., 1969).

The molecular structure of (I) (Fig. 1) resembles those of N-alkylsulfinamides, except that the N-(aryl)C bond (1.409 Å) is considerably shorter than typical N-(alkyl)C bonds in N-alkylsulfinamides (1.470–1.530 Å) (Sato et al., 1975; Schuckmann et al., 1978; Ferreira et al., 2005). The short bond suggests significant delocalization of electrons over the nitrogen atom and the benzene ring. This can be interpreted as indicating considerable contributions to the overall structure of (I) from resonance structures such as those in Fig. 2. The molecules of (I) (with alternating (R) and (S) configurations) are packed in a chain along the b axis (Fig. 3). The crystal packing (Fig. 3) is stabilized by intermolecular N—H···O and C—H···O hydrogen bonds (Fig. 3 and Table 1; symmetry code as in Fig. 3). Interest in sulfinamides lies mainly in their performance as chiral building blocks in organic synthesis (Han et al., 2002; Weix and Ellman, 2003).

Related literature top

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 top

Compound (I) was prepared by the method of Stretter et al.(1969), using aniline (424 mg, 4.56 mmol), 1-adamantanesulfinyl chloride (500 mg, 2.28 mmol) and anhydrous diethyl ether (30 ml). Column chromatography (silica gel, ethyl acetate-dichloromethane, 1:9) gave (I) as white crystals (610 mg, 97%) mp 427–428 K. Literature mp was 428 K (Stretter et al., 1969). Single crystals suitable for X-ray analysis were obtained by evaporation of a solution of the title compound (I) in dichloromethane at room temperature. Spectroscopic analysis: FTIR (KBr) (cm^-1) 3179, 2908, 2851, 1595, 1488, 1450, 1285, 1228, 1175, 1063, 1034, 877. ¹H NMR (400 MHz, CDCl₃, p.p.m. with respect to TMS) 7.26–7.22 (m, 2H), 7.01–6.97 (m, 3H), 5.43 (bs, 1H), 2.18 (s, 3H), 1.92 (dd, J = 11.8, 22.8 Hz, 6H), 1.74 (dd, J = 12.2, 23.4 Hz, 6H). ¹³C NMR (100 MHz, CDCl₃, p.p.m. with respect to TMS) 142.4, 129.2, 122.4, 117.9, 58.2, 36.3, 34.6, 28.5. EIMS m/z (%) 276 (MH⁺,39), 275 (M⁺, 85), 259(M⁺–16, 16), 228 (18), 227 (M⁺–SO,75), 136 (59), 135 (M⁺–PhNHSO, 100), 107 (28), 93 (MH⁺–adamantanesulfinyl, 66), 79 (61).

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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).

Figures top

	Fig. 1. Molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Resonance structures for (I).
	Fig. 3. The packing of (I), viewed down the b axis, showing hydrogen bonding [symmetry code: (i) x, -y + 1/2, z - 1/2; (ii) x, -y + 1/2, z + 1/2].

N-Phenyladamantane-1-sulfinamide top

Crystal data top

C₁₆H₂₁NOS	F(000) = 592
M_r = 275.40	D_x = 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 = 2.3–18.3°
b = 14.5582 (3) Å	µ = 0.22 mm⁻¹
c = 9.0632 (2) Å	T = 293 K
β = 109.777 (1)°	Block, white
V = 1447.90 (5) Å³	0.12 × 0.08 × 0.06 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	3563 independent reflections
Radiation source: fine-focus sealed tube	2623 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω scans	θ_max = 28.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.975, T_max = 0.987	k = −18→19
14147 measured reflections	l = −12→12

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0675P)² + 0.1762P] where P = (F_o² + 2F_c²)/3
3563 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₆H₂₁NOS	V = 1447.90 (5) Å³
M_r = 275.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.6614 (2) Å	µ = 0.22 mm⁻¹
b = 14.5582 (3) Å	T = 293 K
c = 9.0632 (2) Å	0.12 × 0.08 × 0.06 mm
β = 109.777 (1)°

Data collection top

Bruker APEXII diffractometer	3563 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2623 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.987	R_int = 0.030
14147 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.07	Δρ_max = 0.28 e Å⁻³
3563 reflections	Δρ_min = −0.30 e Å⁻³
172 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₁NOS
M_r	275.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.6614 (2), 14.5582 (3), 9.0632 (2)
β (°)	109.777 (1)
V (Å³)	1447.90 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.12 × 0.08 × 0.06

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.975, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	14147, 3563, 2623
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.126, 1.07
No. of reflections	3563
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.30

Computer programs: APEX2 (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.17	2.988 (2)	159.5
C10—H10A···O1ⁱ	0.97	2.35	3.305 (2)	167.7

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

MD and AJB thank KAIST for financial support.

References

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