(S)-N-Phenyl-tert-butane­sulfinamide

Sun, X.; Zhang, X.; Zhang, B.; Wang, W.; Zeng, Q.

doi:10.1107/S1600536812020673

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1728

doi:10.1107/S1600536812020673

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(S)-N-Phenyl-tert-butanesulfinamide

Xiaofei Sun,^a Xiaoping Zhang,^a Binbin Zhang,^a Wenguo Wang ^b and Qingle Zeng ^a ^*

^aInstitute of Green Catalysis and Synthesis, College of Materials and Chemistry & Chemical Engineering, Chengdu University of Technology, Chengdu 610059, People's Republic of China, and ^bFujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, People's Republic of China
^*Correspondence e-mail: qinglezeng@hotmail.com

(Received 24 April 2012; accepted 7 May 2012; online 16 May 2012)

The asymmetric unit of the title compound, C₁₀H₁₅NOS, contains two independent molecules with similar conformations. In the crystal, molecules are linked in a head-to-tail fashion by N—H⋯O hydrogen bonds into chains running along the b axis. The absolute configuration was assigned on the basis of known chirality of the parent compound.

Related literature

For the structures of related N-alkyl and N-aryl alkanesulfinamides, see: Datta et al. (2008 , 2009a ,b , 2010 ); Sun et al. (2012a ,b ) Zhang et al. (2012 ); Sato et al. (1975 ); Schuckmann et al. (1978 ); Ferreira et al. (2005 ).

Experimental

Crystal data

C₁₀H₁₅NOS
M_r = 197.29
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.3596 (4) Å
b = 10.4702 (4) Å
c = 22.7438 (10) Å
V = 2228.82 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.38 × 0.32 × 0.30 mm

Data collection

Aglenet Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.987, T_max = 1.000
6065 measured reflections
3993 independent reflections
2503 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.090
S = 0.98
3993 reflections
249 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ), 1390 Friedel pairs
Flack parameter: −0.09 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.80 (3)	2.17 (3)	2.937 (4)	161 (3)
N2—H2⋯O1ⁱⁱ	0.83 (2)	2.11 (2)	2.914 (4)	166 (3)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y-{\script{5\over 2}}, -z]$ ; (ii) $[-x-{\script{1\over 2}}, -y-2, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812020673/rz2751sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812020673/rz2751Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812020673/rz2751Isup3.cml

checkCIF report

Comment top

In recent years, sulfonamide moieties have played an increasingly important role in organic chemistry, particularly due to their use as chiral auxiliaries or precursors for the synthesis of a broad family of pharmaceutical agents. As a contribution to this research field, the X-ray crystallographic study of the title compound (Fig. 1) is reported herein. A number of related (R)—N-(3-methoxyphenyl) tert-butanesulfinamides, (R)—N-(4-biphenyl) tert-butanesulfinamide, N-aryl alkanesulfinamides and N-alkyl alkanesulfinamides have been reported recently (Datta et al., 2008, 2009a, 2009b, 2010; Sun et al., 2012a, 2012b Zhang et al., 2012; Sato et al., 1975; Schuckmann et al., 1978; Ferreira et al., 2005).

In the title compound, the value of the N-C(aryl) bond (N1—C1 = 1.403 (4) Å; N2—C11 = 1.403 (4) Å) is considerably shorter than those typically found in N-alkylsulfinamides (1.470–1.530 Å; Sato et al., 1975; Schuckmann et al., 1978; Ferreira et al., 2005), suggesting a significant delocalization of electrons over the nitrogen atom and the benzene ring. In the crystal structure, the molecules are linked into chains parallel to the b axis by intermolecular N—H···O hydrogen bonds (Fig. 2; Table 1).

Related literature top

For the structures of related N-alkyl and N-aryl alkanesulfinamides, see: Datta et al. (2008, 2009a,b, 2010); Sun et al. (2012a,b) Zhang et al. (2012); Sato et al. (1975); Schuckmann et al. (1978); Ferreira et al. (2005).

Experimental top

A oven-dried ground test tube, which was equipped with a magnetic stir bar and fitted with a rubber septum, was charged with (S)-tert-butanesulfinamide (0.121 g, 1.0 mmol), Pd₂(dba)3 (0.018 g, 0.02 mmol), tBu-XPhos (0.0212 g, 0.05 mmol) and NaOH (0.08 g, 2 mmol). The vessel was evacuated and backfilled with argon (this process was repeated a total of 3 times) and then phenyl bromide (1.3 mmol), toluene (10 ml) and degassed water (0.3 ml) were added via syringe. The solution was stirred at 90° for 20 h. The reaction mixture was then cooled to room temperature, quenched by water, and extracted with ethyl acetate (2 × 20 ml). The organic layer was combined, dried over anhydrous sodium sulfate and filtrated. The filterate was condensed under vacuum. The residual was purified with silica gel column chromatography with a solution of petroleum ether/ethyl acetate (5:1 v/v) as an eluent to give a white solid (0.167 g, yield 86%). A test tube containing the eluate (petroleum ether/ethyl acetate (5:1 v/v) was covered with a piece of filter paper and placed motionless at room temperature (about 20°), until a single-crystal was cultured in the bottom of the test tube. M.p.: 383–386 K. [α]D²¹ = +179 (c 3/4, ethyl acetate). Spectroscopic analysis: ¹H NMR (300 MHz, CDCl₃), δ (p.p.m.): 7.25–7.24 (m, 2H), 7.01 (t, J = 6.3 Hz, 3H), 5.41 (d, J = 11.1 Hz, 1H), 1.33 (s, 9H). ¹³C NMR (75 MHz, CDCl₃), δ (p.p.m.): 142.1, 129.1, 122.4, 117.9, 56.3, 22.3. IR (KBr), ν (cm^-1): 3452, 3145, 2961, 2889, 1598, 1495, 1412, 1363, 1287, 1236, 1053, 887, 751. ESI-MS (negative mode), m/z = 196 [M—H]^-.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The one-dimensional structure of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.

(S)-N-Phenyl-tert-butanesulfinamide top

Crystal data top

C₁₀H₁₅NOS	D_x = 1.176 Mg m⁻³
M_r = 197.29	Melting point = 383–386 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.7107 Å
a = 9.3596 (4) Å	Cell parameters from 1915 reflections
b = 10.4702 (4) Å	θ = 3.1–29.1°
c = 22.7438 (10) Å	µ = 0.25 mm⁻¹
V = 2228.82 (17) Å³	T = 293 K
Z = 8	Block, colourless
F(000) = 848	0.38 × 0.32 × 0.30 mm

Data collection top

Aglenet Xcalibur Eos diffractometer	3993 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2503 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 16.0874 pixels mm^-1	θ_max = 26.4°, θ_min = 3.1°
ω scans	h = −11→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −13→10
T_min = 0.987, T_max = 1.000	l = −16→28
6065 measured reflections

Refinement top

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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.090	w = 1/[σ²(F_o²) + (0.0271P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.001
3993 reflections	Δρ_max = 0.26 e Å⁻³
249 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1390 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.09 (9)

Crystal data top

C₁₀H₁₅NOS	V = 2228.82 (17) Å³
M_r = 197.29	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.3596 (4) Å	µ = 0.25 mm⁻¹
b = 10.4702 (4) Å	T = 293 K
c = 22.7438 (10) Å	0.38 × 0.32 × 0.30 mm

Data collection top

Aglenet Xcalibur Eos diffractometer	3993 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2503 reflections with I > 2σ(I)
T_min = 0.987, T_max = 1.000	R_int = 0.025
6065 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.090	Δρ_max = 0.26 e Å⁻³
S = 0.98	Δρ_min = −0.26 e Å⁻³
3993 reflections	Absolute structure: Flack (1983), 1390 Friedel pairs
249 parameters	Absolute structure parameter: −0.09 (9)
0 restraints

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
S1	−0.63522 (11)	−0.88887 (8)	−0.08184 (4)	0.0658 (3)
S2	0.04812 (9)	−1.49605 (8)	0.25283 (4)	0.0596 (2)
O1	−0.6196 (3)	−0.7833 (2)	−0.12453 (11)	0.0943 (9)
O2	0.0446 (3)	−1.3883 (2)	0.20975 (9)	0.0730 (7)
N1	−0.5152 (4)	−0.9991 (3)	−0.09407 (14)	0.0781 (10)
H1	−0.517 (3)	−1.037 (2)	−0.1245 (12)	0.051 (11)*
N2	0.0029 (4)	−1.4435 (3)	0.31882 (13)	0.0702 (10)
H2	0.042 (3)	−1.376 (2)	0.3290 (11)	0.038 (9)*
C1	−0.3963 (4)	−1.0169 (3)	−0.05740 (14)	0.0567 (9)
C2	−0.3226 (4)	−1.1295 (3)	−0.06151 (15)	0.0697 (11)
H2A	−0.3507	−1.1910	−0.0887	0.084*
C3	−0.2065 (5)	−1.1521 (4)	−0.02543 (17)	0.0783 (12)
H3	−0.1560	−1.2283	−0.0289	0.094*
C4	−0.1653 (5)	−1.0632 (5)	0.01535 (16)	0.0814 (13)
H4	−0.0881	−1.0792	0.0400	0.098*
C5	−0.2383 (5)	−0.9517 (4)	0.01931 (17)	0.0805 (12)
H5	−0.2106	−0.8912	0.0470	0.097*
C6	−0.3530 (5)	−0.9262 (3)	−0.01707 (15)	0.0683 (11)
H6	−0.4007	−0.8485	−0.0144	0.082*
C7	−0.7985 (4)	−0.9729 (3)	−0.10372 (14)	0.0651 (10)
C8	−0.7966 (4)	−0.9995 (4)	−0.17018 (14)	0.0892 (12)
H8A	−0.7820	−0.9209	−0.1911	0.134*
H8B	−0.8861	−1.0365	−0.1818	0.134*
H8C	−0.7204	−1.0577	−0.1792	0.134*
C9	−0.9184 (4)	−0.8808 (3)	−0.08820 (16)	0.0868 (12)
H9A	−0.9160	−0.8631	−0.0468	0.130*
H9B	−1.0086	−0.9185	−0.0982	0.130*
H9C	−0.9061	−0.8027	−0.1097	0.130*
C10	−0.8088 (4)	−1.0947 (3)	−0.06758 (17)	0.1018 (15)
H10A	−0.7340	−1.1523	−0.0790	0.153*
H10B	−0.8999	−1.1343	−0.0743	0.153*
H10C	−0.7991	−1.0744	−0.0266	0.153*
C11	−0.1317 (4)	−1.4709 (3)	0.34283 (13)	0.0549 (9)
C12	−0.2013 (4)	−1.5837 (3)	0.33049 (14)	0.0687 (11)
H12	−0.1604	−1.6432	0.3052	0.082*
C13	−0.3322 (4)	−1.6075 (4)	0.35607 (17)	0.0791 (11)
H13	−0.3804	−1.6823	0.3466	0.095*
C14	−0.3932 (4)	−1.5244 (5)	0.39494 (17)	0.0868 (13)
H14	−0.4807	−1.5427	0.4123	0.104*
C15	−0.3220 (4)	−1.4137 (4)	0.40762 (16)	0.0815 (13)
H15	−0.3619	−1.3566	0.4343	0.098*
C16	−0.1937 (4)	−1.3846 (3)	0.38212 (14)	0.0705 (10)
H16	−0.1481	−1.3080	0.3909	0.085*
C17	0.2373 (4)	−1.5304 (3)	0.26576 (14)	0.0632 (10)
C18	0.2876 (5)	−1.5848 (4)	0.20743 (18)	0.1162 (16)
H18A	0.2232	−1.6508	0.1950	0.174*
H18B	0.3817	−1.6199	0.2120	0.174*
H18C	0.2898	−1.5182	0.1785	0.174*
C19	0.3190 (4)	−1.4111 (3)	0.28162 (15)	0.0825 (12)
H19A	0.3082	−1.3490	0.2509	0.124*
H19B	0.4184	−1.4314	0.2863	0.124*
H19C	0.2825	−1.3768	0.3178	0.124*
C20	0.2443 (5)	−1.6306 (4)	0.31436 (17)	0.1057 (15)
H20A	0.2186	−1.5922	0.3512	0.159*
H20B	0.3397	−1.6639	0.3169	0.159*
H20C	0.1791	−1.6988	0.3056	0.159*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0774 (6)	0.0593 (5)	0.0608 (5)	0.0046 (6)	0.0068 (6)	−0.0011 (5)
S2	0.0663 (5)	0.0637 (5)	0.0488 (4)	−0.0082 (6)	0.0024 (5)	−0.0111 (5)
O1	0.102 (2)	0.0703 (15)	0.1102 (19)	−0.0104 (17)	0.011 (2)	0.0274 (15)
O2	0.0870 (17)	0.0736 (15)	0.0582 (14)	0.0001 (18)	−0.0085 (15)	0.0076 (12)
N1	0.087 (2)	0.092 (2)	0.0550 (19)	0.022 (2)	−0.005 (2)	−0.027 (2)
N2	0.078 (2)	0.071 (2)	0.0618 (19)	−0.024 (2)	0.0131 (19)	−0.0221 (17)
C1	0.067 (2)	0.060 (2)	0.0430 (18)	0.001 (2)	0.0080 (18)	−0.0012 (18)
C2	0.078 (3)	0.067 (3)	0.063 (2)	0.000 (3)	0.003 (2)	−0.0006 (19)
C3	0.082 (3)	0.075 (3)	0.078 (3)	0.017 (3)	0.013 (3)	0.010 (2)
C4	0.077 (3)	0.106 (3)	0.061 (3)	0.002 (3)	−0.003 (3)	0.012 (3)
C5	0.094 (3)	0.088 (3)	0.059 (3)	−0.011 (3)	0.002 (3)	−0.004 (2)
C6	0.087 (3)	0.066 (2)	0.052 (2)	−0.002 (3)	0.007 (2)	0.0038 (19)
C7	0.072 (3)	0.054 (2)	0.069 (2)	0.004 (2)	0.009 (2)	0.0059 (18)
C8	0.087 (3)	0.102 (3)	0.078 (3)	0.004 (3)	−0.009 (3)	−0.017 (2)
C9	0.076 (3)	0.083 (3)	0.101 (3)	0.011 (3)	0.014 (3)	−0.004 (2)
C10	0.116 (4)	0.073 (3)	0.117 (3)	−0.010 (3)	0.024 (3)	0.021 (2)
C11	0.062 (2)	0.057 (2)	0.0462 (19)	−0.001 (2)	0.000 (2)	0.0024 (17)
C12	0.068 (3)	0.073 (3)	0.065 (2)	0.001 (2)	0.012 (2)	−0.0014 (19)
C13	0.071 (3)	0.082 (3)	0.084 (3)	−0.009 (3)	0.007 (3)	0.004 (2)
C14	0.065 (3)	0.117 (3)	0.079 (3)	0.010 (3)	0.014 (2)	0.017 (3)
C15	0.081 (3)	0.097 (3)	0.066 (3)	0.027 (3)	0.017 (3)	−0.004 (2)
C16	0.086 (3)	0.070 (2)	0.055 (2)	0.012 (3)	0.008 (2)	−0.004 (2)
C17	0.068 (2)	0.063 (2)	0.058 (2)	0.002 (2)	0.001 (2)	−0.0055 (18)
C18	0.091 (3)	0.150 (4)	0.107 (3)	0.016 (3)	0.013 (3)	−0.052 (3)
C19	0.071 (3)	0.078 (3)	0.098 (3)	−0.009 (2)	−0.004 (2)	−0.002 (2)
C20	0.105 (3)	0.084 (3)	0.128 (4)	0.000 (3)	−0.019 (3)	0.025 (3)

Geometric parameters (Å, º) top

S1—O1	1.479 (2)	C9—H9B	0.9600
S1—N1	1.634 (3)	C9—H9C	0.9600
S1—C7	1.832 (4)	C10—H10A	0.9600
S2—O2	1.494 (2)	C10—H10B	0.9600
S2—N2	1.654 (3)	C10—H10C	0.9600
S2—C17	1.831 (4)	C11—C12	1.378 (4)
N1—H1	0.80 (3)	C11—C16	1.397 (4)
N1—C1	1.403 (4)	C12—H12	0.9300
N2—H2	0.83 (2)	C12—C13	1.379 (5)
N2—C11	1.403 (4)	C13—H13	0.9300
C1—C2	1.370 (4)	C13—C14	1.365 (5)
C1—C6	1.381 (4)	C14—H14	0.9300
C2—H2A	0.9300	C14—C15	1.368 (5)
C2—C3	1.382 (5)	C15—H15	0.9300
C3—H3	0.9300	C15—C16	1.368 (5)
C3—C4	1.370 (5)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.519 (4)
C4—C5	1.356 (5)	C17—C19	1.509 (4)
C5—H5	0.9300	C17—C20	1.526 (4)
C5—C6	1.381 (5)	C18—H18A	0.9600
C6—H6	0.9300	C18—H18B	0.9600
C7—C8	1.537 (4)	C18—H18C	0.9600
C7—C9	1.521 (4)	C19—H19A	0.9600
C7—C10	1.520 (4)	C19—H19B	0.9600
C8—H8A	0.9600	C19—H19C	0.9600
C8—H8B	0.9600	C20—H20A	0.9600
C8—H8C	0.9600	C20—H20B	0.9600
C9—H9A	0.9600	C20—H20C	0.9600

O1—S1—N1	110.38 (17)	C7—C10—H10A	109.5
O1—S1—C7	105.27 (16)	C7—C10—H10B	109.5
N1—S1—C7	100.83 (16)	C7—C10—H10C	109.5
O2—S2—N2	109.77 (14)	H10A—C10—H10B	109.5
O2—S2—C17	105.97 (15)	H10A—C10—H10C	109.5
N2—S2—C17	99.62 (16)	H10B—C10—H10C	109.5
S1—N1—H1	119 (2)	C12—C11—N2	121.4 (3)
C1—N1—S1	122.5 (3)	C12—C11—C16	119.3 (4)
C1—N1—H1	118 (2)	C16—C11—N2	119.3 (3)
S2—N2—H2	115.2 (19)	C11—C12—H12	120.4
C11—N2—S2	121.0 (3)	C11—C12—C13	119.2 (4)
C11—N2—H2	117.5 (19)	C13—C12—H12	120.4
C2—C1—N1	118.3 (3)	C12—C13—H13	119.0
C2—C1—C6	119.3 (3)	C14—C13—C12	122.0 (4)
C6—C1—N1	122.5 (4)	C14—C13—H13	119.0
C1—C2—H2A	119.9	C13—C14—H14	120.9
C1—C2—C3	120.2 (4)	C13—C14—C15	118.2 (4)
C3—C2—H2A	119.9	C15—C14—H14	120.9
C2—C3—H3	119.8	C14—C15—H15	119.1
C4—C3—C2	120.5 (4)	C14—C15—C16	121.8 (4)
C4—C3—H3	119.8	C16—C15—H15	119.1
C3—C4—H4	120.4	C11—C16—H16	120.3
C5—C4—C3	119.2 (4)	C15—C16—C11	119.4 (4)
C5—C4—H4	120.4	C15—C16—H16	120.3
C4—C5—H5	119.4	C18—C17—S2	103.5 (2)
C4—C5—C6	121.2 (4)	C18—C17—C20	111.2 (3)
C6—C5—H5	119.4	C19—C17—S2	111.5 (2)
C1—C6—C5	119.6 (4)	C19—C17—C18	111.3 (3)
C1—C6—H6	120.2	C19—C17—C20	112.0 (3)
C5—C6—H6	120.2	C20—C17—S2	107.0 (3)
C8—C7—S1	110.1 (3)	C17—C18—H18A	109.5
C9—C7—S1	104.3 (2)	C17—C18—H18B	109.5
C9—C7—C8	110.6 (3)	C17—C18—H18C	109.5
C10—C7—S1	108.0 (3)	H18A—C18—H18B	109.5
C10—C7—C8	112.4 (3)	H18A—C18—H18C	109.5
C10—C7—C9	111.1 (3)	H18B—C18—H18C	109.5
C7—C8—H8A	109.5	C17—C19—H19A	109.5
C7—C8—H8B	109.5	C17—C19—H19B	109.5
C7—C8—H8C	109.5	C17—C19—H19C	109.5
H8A—C8—H8B	109.5	H19A—C19—H19B	109.5
H8A—C8—H8C	109.5	H19A—C19—H19C	109.5
H8B—C8—H8C	109.5	H19B—C19—H19C	109.5
C7—C9—H9A	109.5	C17—C20—H20A	109.5
C7—C9—H9B	109.5	C17—C20—H20B	109.5
C7—C9—H9C	109.5	C17—C20—H20C	109.5
H9A—C9—H9B	109.5	H20A—C20—H20B	109.5
H9A—C9—H9C	109.5	H20A—C20—H20C	109.5
H9B—C9—H9C	109.5	H20B—C20—H20C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.80 (3)	2.17 (3)	2.937 (4)	161 (3)
N2—H2···O1ⁱⁱ	0.83 (2)	2.11 (2)	2.914 (4)	166 (3)

Symmetry codes: (i) x−1/2, −y−5/2, −z; (ii) −x−1/2, −y−2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₅NOS
M_r	197.29
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	9.3596 (4), 10.4702 (4), 22.7438 (10)
V (Å³)	2228.82 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.38 × 0.32 × 0.30

Data collection
Diffractometer	Aglenet Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.987, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6065, 3993, 2503
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.090, 0.98
No. of reflections	3993
No. of parameters	249
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.26
Absolute structure	Flack (1983), 1390 Friedel pairs
Absolute structure parameter	−0.09 (9)

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.80 (3)	2.17 (3)	2.937 (4)	161 (3)
N2—H2···O1ⁱⁱ	0.83 (2)	2.11 (2)	2.914 (4)	166 (3)

Symmetry codes: (i) x−1/2, −y−5/2, −z; (ii) −x−1/2, −y−2, z+1/2.

Acknowledgements

We thank the Ministry of Human Resources and Social Security of China, the Science and Technology Bureau of Sichuan (grant No. 2011HH0016), the Open Fund of the State Key Laboratory of Geohazard Prevention and Geoenvironment Protection and the Cultivating Programme for Excellent Innovation Teams of Chengdu University of Technology (No. HY0084) for financial support.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England. Google Scholar
Datta, M., Buglass, A. J. & Elsegood, M. R. J. (2009a). Acta Cryst. E65, o2823. Web of Science CSD CrossRef IUCr Journals Google Scholar
Datta, M., Buglass, A. J. & Elsegood, M. R. J. (2009b). Acta Cryst. E65, o2034. Web of Science CSD CrossRef IUCr Journals Google Scholar
Datta, M., Buglass, A. J. & Elsegood, M. R. J. (2010). Acta Cryst. E66, o109. Web of Science CSD CrossRef IUCr Journals Google Scholar
Datta, M., Buglass, A. J., Hong, C. S. & Lim, J. H. (2008). Acta Cryst. E64, o1393. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ferreira, F., Audoin, M. & Chemla, F. (2005). Chem. Eur. J. 11, 5269–5278. Web of Science CSD CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sato, S., Yoshioka, T. & Tamura, C. (1975). Acta Cryst. B31, 1385–1392. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Schuckmann, W., Fuess, H., Mösinger, O. & Ried, W. (1978). Acta Cryst. B34, 1516–1520. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, X., Dai, C., Tu, X., Wang, W. & Zeng, Q. (2012a). Acta Cryst. E68, o773. CSD CrossRef IUCr Journals Google Scholar
Sun, X. F., Tu, X. Z., Dai, C., Zhang, X. P., Zhang, B. B. & Zeng, Q. L. (2012b). J. Org. Chem. 77, 4454–4459. Web of Science CSD CrossRef CAS PubMed Google Scholar
Zhang, B., Wang, Y., Sun, X., Wang, W. & Zeng, Q. (2012). Acta Cryst. E68, o1389. CSD CrossRef IUCr Journals Google Scholar