(2,6-Diisopropyl­phen­yl)(2-thienylmethyl­ene)amine

Imhof, W.

doi:10.1107/S1600536809006291

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o593

doi:10.1107/S1600536809006291

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(2,6-Diisopropylphenyl)(2-thienylmethylene)amine

Wolfgang Imhof ^a ^*

^aInstitute of Inorganic and Analytical Chemistry, Friedrich Schiller University, August-Bebel-Strasse 2, 07743 Jena, Germany
^*Correspondence e-mail: wolfgang.imhof@uni-jena.de

(Received 19 February 2009; accepted 20 February 2009; online 25 February 2009)

The title compound, C₁₇H₂₁NS, was prepared by the condensation of thiophene-2-carbaldehyde with 2,6-diisopropylaniline. It crystallizes with two molecules in the asymmetric unit. The molecules are interconnected via a C—H⋯N hydrogen bond. The dihedral angles between the thiophene and phenyl rings are 81.7 (7) and 85.5 (7)°.

Related literature

For the synthetic procedure, see: Drisko & McKennis (1952 ); Wang et al. (2007 ). For related structures, see: Kazak et al. (2000 ); Małeki et al. (2007 ). For the organometallic chemistry of related ligands, see: Imhof (1997a ,b ).

Experimental

Crystal data

C₁₇H₂₁NS
M_r = 271.42
Monoclinic, P 2₁
a = 10.0877 (9) Å
b = 14.275 (3) Å
c = 11.4503 (9) Å
β = 109.651 (8)°
V = 1552.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.51 × 0.43 × 0.33 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.884, T_max = 0.939
2222 measured reflections
2096 independent reflections
2055 reflections with I > 2σ(I)
R_int = 0.023
θ_max = 23.0°
3 standard reflections frequency: 120 min intensity decay: 0.02%

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.079
S = 1.08
2096 reflections
353 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯N1	0.93	2.52	3.449 (8)	178

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: SET4 (de Boer et al., 1984 ); data reduction: MolEN (Enraf–Nonius, 1990 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1990 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006291/bt2882sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006291/bt2882Isup2.hkl

checkCIF report

Comment top

In the course of a study on stoichiometric and catalytic C—H activation reactions of imines derived from 2- or 3-thiophene-carbaldehydes and aniline derivatives (Imhof, 1997a, 1997b) we synthesized the title compound that exhibits two bulky ortho-substituents at the phenyl ring. The compound crystallizes with two molecules per asymmetric unit. These molecules are interconnected by hydrogen bonds between the imine nitrogen atom as the acceptor and one of the thiophene C—H functions as the hydrogen bond donor (Table 1). Bond lengths and angles correspond to values that have been reported for related imines from 2-thiophenecarbaldehyde and aniline derivatives (Kazak et al., 2000; Małeki et al., 2007). The dihedral angles between the thiophene and the phenyl rings measure to 98.3 (7)° and 94.5 (7)°, respectively. These values are significantly higher than those observed for compounds without bulky ortho-substituents (Kazak et al., 2000: 20.8 (1)°; Małeki et al., 2007: 49.38 (6)°).

Related literature top

For the synthetic procedure, see: Drisko & McKennis (1952); Wang et al. (2007). For related structures, see: Kazak et al. (2000); Małeki et al. (2007). For the organometallic chemistry of related ligands, see: Imhof (1997a,b).

Experimental top

The title compound was prepared in analogy to a literature method (Drisko & McKennis, 1952). The synthesis of the compound has also been recently described as an intermediate in the synthesis of the corresponding amine (Wang et al., 2007). The ¹H-NMR spectrum of the title compound is identical to the one described in the latter publication. Single crystals are produced from a solution of the compound in light petroleum (b.p. 40–60°) and dichloromethane (20:1) at -20°. MS (EI) [m/z, %]: 271 (M⁺, 76), 256 (M⁺ - Me, 59), 214 (C₁₃H₁₂NS⁺, 100), 199 (C₁₂H₉NS⁺, 17), 172 (C₁₀H₆NS⁺, 25), 146 (C₉H₆S⁺, 33), 132 (C₈H₄S⁺, 25), 115 (C₉H₇⁺, 15), 97 (C₅H₅S⁺, 36), 91 (C₇H₇⁺, 19), 77 (C₆H₅⁺, 13), 53 (C₄H₅⁺, 8), 41 (C₃H₅⁺, 14); IR (nujol mull) [cm^-1]: 1629 (CH=N); ¹³C-NMR (CDCl₃, 298 K) [p.p.m.]: 23.5 (CH₃), 28.0 (CH), 123.0 (C_arH), 124.3 (C_arH), 127.7 (C_arH), 130.2 (C_arH), 131.6 (C_arH), 137.9 (C_ar), 142.6 (C_ar), 148.6 (C_ar), 154.9 (N=CH).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: SET4 (de Boer et al., 1984); data reduction: MolEN (Enraf–Nonius, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, presenting the labelling scheme and 30% probability displacement ellipsoids for non-H atoms.

(2,6-Diisopropylphenyl)(2-thienylmethylene)amine top

Crystal data top

C₁₇H₂₁NS	F(000) = 584
M_r = 271.42	D_x = 1.161 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 10.0877 (9) Å	θ = 36.5–42.8°
b = 14.275 (3) Å	µ = 0.20 mm⁻¹
c = 11.4503 (9) Å	T = 173 K
β = 109.651 (8)°	Cube, yellow
V = 1552.8 (4) Å³	0.51 × 0.43 × 0.33 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2055 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 23.0°, θ_min = 1.9°
ω/2θ scans	h = −11→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→15
T_min = 0.884, T_max = 0.939	l = 0→12
2222 measured reflections	3 standard reflections every 120 min
2096 independent reflections	intensity decay: 0.02%

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)] = 0.028	H-atom parameters constrained
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.0606P)² + 0.2045P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
2096 reflections	Δρ_max = 0.20 e Å⁻³
353 parameters	Δρ_min = −0.19 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0222 (27)

Crystal data top

C₁₇H₂₁NS	V = 1552.8 (4) Å³
M_r = 271.42	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 10.0877 (9) Å	µ = 0.20 mm⁻¹
b = 14.275 (3) Å	T = 173 K
c = 11.4503 (9) Å	0.51 × 0.43 × 0.33 mm
β = 109.651 (8)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2055 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.023
T_min = 0.884, T_max = 0.939	θ_max = 23.0°
2222 measured reflections	3 standard reflections every 120 min
2096 independent reflections	intensity decay: 0.02%

Refinement top

R[F² > 2σ(F²)] = 0.028	1 restraint
wR(F²) = 0.079	H-atom parameters constrained
S = 1.08	Δρ_max = 0.20 e Å⁻³
2096 reflections	Δρ_min = −0.19 e Å⁻³
353 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 on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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	0.92670 (8)	0.27773 (6)	0.17143 (7)	0.0403 (2)
C1	0.8043 (4)	0.3644 (2)	0.1137 (3)	0.0455 (8)
H1	0.8191	0.4169	0.0716	0.055*
C2	0.6842 (4)	0.3472 (2)	0.1367 (3)	0.0441 (8)
H2	0.6065	0.3868	0.1122	0.053*
C3	0.6886 (3)	0.2627 (2)	0.2017 (3)	0.0373 (7)
H3	0.6143	0.2407	0.2250	0.045*
C4	0.8135 (3)	0.2166 (2)	0.2268 (2)	0.0304 (7)
C5	0.8510 (3)	0.1257 (2)	0.2850 (2)	0.0290 (6)
H5	0.7887	0.0959	0.3170	0.035*
N1	0.9657 (2)	0.08570 (16)	0.2936 (2)	0.0307 (6)
C6	0.9982 (3)	−0.0052 (2)	0.3474 (3)	0.0303 (6)
C7	1.0936 (3)	−0.0118 (2)	0.4707 (3)	0.0332 (7)
C8	1.1362 (3)	−0.1004 (2)	0.5183 (3)	0.0402 (7)
H8	1.1975	−0.1061	0.5994	0.048*
C9	1.0900 (4)	−0.1802 (2)	0.4487 (3)	0.0459 (8)
H9	1.1204	−0.2389	0.4822	0.055*
C10	0.9987 (4)	−0.1719 (2)	0.3292 (3)	0.0481 (9)
H10	0.9695	−0.2259	0.2820	0.058*
C11	0.9485 (3)	−0.0855 (2)	0.2764 (3)	0.0371 (7)
C12	1.1462 (3)	0.0744 (2)	0.5499 (3)	0.0425 (8)
H12	1.1123	0.1299	0.4980	0.051*
C13	1.3055 (5)	0.0779 (4)	0.6001 (6)	0.0936 (16)
H13A	1.3415	0.0749	0.5326	0.112*
H13B	1.3405	0.0258	0.6547	0.112*
H13C	1.3353	0.1354	0.6449	0.112*
C14	1.0880 (6)	0.0770 (3)	0.6541 (5)	0.0860 (15)
H14A	1.1285	0.1288	0.7079	0.103*
H14B	1.1105	0.0196	0.7002	0.103*
H14C	0.9876	0.0844	0.6211	0.103*
C15	0.8490 (4)	−0.0815 (2)	0.1424 (3)	0.0483 (9)
H15	0.8103	−0.0180	0.1261	0.058*
C16	0.7261 (4)	−0.1501 (3)	0.1206 (4)	0.0586 (10)
H16A	0.6602	−0.1416	0.0384	0.070*
H16B	0.6800	−0.1386	0.1802	0.070*
H16C	0.7611	−0.2132	0.1296	0.070*
C17	0.9284 (4)	−0.1013 (3)	0.0537 (3)	0.0595 (10)
H17A	0.8637	−0.1017	−0.0299	0.071*
H17B	0.9739	−0.1611	0.0728	0.071*
H17C	0.9979	−0.0534	0.0621	0.071*
S2	1.45567 (7)	0.01922 (5)	0.12971 (7)	0.0362 (2)
C18	1.3736 (3)	0.1201 (2)	0.0597 (3)	0.0364 (7)
H18	1.4044	0.1563	0.0064	0.044*
C19	1.2598 (3)	0.1407 (2)	0.0909 (3)	0.0376 (7)
H19	1.2027	0.1927	0.0613	0.045*
C20	1.2366 (3)	0.0744 (2)	0.1739 (3)	0.0338 (7)
H20	1.1629	0.0785	0.2052	0.041*
C21	1.3337 (3)	0.0036 (2)	0.2034 (2)	0.0299 (6)
C22	1.3372 (3)	−0.0769 (2)	0.2809 (3)	0.0306 (7)
H22	1.2697	−0.0816	0.3194	0.037*
N2	1.4285 (3)	−0.14133 (17)	0.2987 (2)	0.0330 (6)
C23	1.4182 (3)	−0.2197 (2)	0.3739 (2)	0.0284 (6)
C24	1.3357 (3)	−0.2969 (2)	0.3184 (3)	0.0298 (6)
C25	1.3289 (3)	−0.3717 (2)	0.3932 (3)	0.0336 (7)
H25	1.2725	−0.4229	0.3582	0.040*
C26	1.4047 (3)	−0.3717 (2)	0.5197 (3)	0.0346 (7)
H26	1.3980	−0.4222	0.5688	0.041*
C27	1.4899 (3)	−0.2964 (2)	0.5719 (3)	0.0351 (7)
H27	1.5428	−0.2977	0.6559	0.042*
C28	1.4983 (3)	−0.2185 (2)	0.5012 (3)	0.0318 (6)
C29	1.2653 (3)	−0.3020 (2)	0.1779 (3)	0.0349 (7)
H29	1.2322	−0.2389	0.1487	0.042*
C30	1.3730 (4)	−0.3295 (3)	0.1190 (3)	0.0516 (9)
H30A	1.4096	−0.3905	0.1478	0.062*
H30B	1.4484	−0.2847	0.1413	0.062*
H30C	1.3294	−0.3306	0.0304	0.062*
C31	1.1389 (3)	−0.3669 (3)	0.1358 (3)	0.0480 (8)
H31A	1.0931	−0.3608	0.0479	0.058*
H31B	1.0741	−0.3506	0.1777	0.058*
H31C	1.1694	−0.4305	0.1553	0.058*
C32	1.5953 (3)	−0.1370 (2)	0.5574 (3)	0.0417 (8)
H32	1.5458	−0.0794	0.5207	0.050*
C33	1.6322 (5)	−0.1290 (3)	0.6970 (3)	0.0681 (12)
H33A	1.6913	−0.0753	0.7265	0.082*
H33B	1.6812	−0.1844	0.7360	0.082*
H33C	1.5475	−0.1222	0.7168	0.082*
C34	1.7288 (4)	−0.1426 (3)	0.5227 (4)	0.0704 (12)
H34A	1.7039	−0.1416	0.4340	0.084*
H34B	1.7781	−0.1997	0.5546	0.084*
H34C	1.7884	−0.0901	0.5576	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0442 (4)	0.0359 (4)	0.0387 (4)	0.0012 (4)	0.0110 (3)	0.0054 (4)
C1	0.065 (2)	0.0341 (18)	0.0314 (17)	0.0049 (17)	0.0084 (16)	0.0048 (15)
C2	0.0512 (19)	0.0363 (18)	0.0319 (17)	0.0130 (15)	−0.0027 (15)	0.0002 (15)
C3	0.0383 (15)	0.0336 (18)	0.0328 (16)	0.0051 (14)	0.0023 (13)	−0.0005 (14)
C4	0.0334 (14)	0.0325 (16)	0.0187 (14)	0.0017 (12)	0.0000 (12)	−0.0056 (13)
C5	0.0338 (14)	0.0297 (15)	0.0189 (14)	−0.0001 (13)	0.0028 (11)	−0.0028 (13)
N1	0.0334 (13)	0.0268 (13)	0.0280 (13)	0.0034 (11)	0.0051 (10)	0.0002 (11)
C6	0.0343 (14)	0.0281 (16)	0.0286 (16)	0.0019 (12)	0.0109 (12)	0.0022 (13)
C7	0.0403 (16)	0.0293 (16)	0.0282 (16)	0.0003 (13)	0.0090 (13)	0.0033 (13)
C8	0.0479 (17)	0.0363 (17)	0.0280 (16)	0.0050 (15)	0.0018 (14)	0.0030 (15)
C9	0.064 (2)	0.0281 (17)	0.0399 (19)	0.0096 (16)	0.0093 (16)	0.0048 (15)
C10	0.064 (2)	0.0284 (17)	0.044 (2)	0.0051 (16)	0.0069 (17)	−0.0067 (15)
C11	0.0416 (16)	0.0295 (16)	0.0340 (17)	0.0049 (13)	0.0045 (14)	−0.0049 (14)
C12	0.0499 (18)	0.0313 (17)	0.0337 (16)	−0.0038 (15)	−0.0023 (14)	0.0059 (15)
C13	0.065 (3)	0.080 (4)	0.124 (4)	−0.029 (3)	0.016 (3)	−0.031 (3)
C14	0.140 (4)	0.055 (3)	0.081 (3)	−0.010 (3)	0.062 (3)	−0.028 (3)
C15	0.058 (2)	0.0320 (17)	0.0383 (19)	0.0107 (16)	−0.0054 (16)	−0.0065 (15)
C16	0.0452 (19)	0.062 (2)	0.056 (2)	0.0053 (17)	0.0012 (18)	−0.016 (2)
C17	0.069 (2)	0.064 (2)	0.0341 (18)	−0.008 (2)	0.0018 (16)	0.0017 (19)
S2	0.0377 (4)	0.0345 (4)	0.0361 (4)	0.0016 (3)	0.0120 (3)	0.0049 (3)
C18	0.0454 (17)	0.0320 (16)	0.0280 (15)	−0.0045 (14)	0.0073 (13)	0.0094 (14)
C19	0.0380 (16)	0.0284 (16)	0.0393 (17)	0.0013 (14)	0.0034 (14)	0.0053 (15)
C20	0.0354 (15)	0.0311 (16)	0.0320 (15)	0.0005 (13)	0.0074 (12)	0.0013 (13)
C21	0.0335 (14)	0.0277 (15)	0.0216 (14)	−0.0030 (12)	0.0003 (11)	0.0013 (13)
C22	0.0325 (15)	0.0292 (15)	0.0257 (15)	−0.0037 (13)	0.0038 (12)	0.0001 (13)
N2	0.0393 (13)	0.0289 (13)	0.0270 (13)	0.0025 (11)	0.0060 (11)	0.0055 (11)
C23	0.0325 (13)	0.0270 (14)	0.0243 (14)	0.0045 (13)	0.0076 (12)	0.0066 (13)
C24	0.0343 (14)	0.0282 (15)	0.0248 (15)	0.0058 (12)	0.0070 (12)	0.0067 (13)
C25	0.0398 (15)	0.0281 (15)	0.0296 (16)	0.0006 (14)	0.0072 (13)	−0.0006 (14)
C26	0.0493 (16)	0.0261 (15)	0.0289 (16)	0.0040 (14)	0.0138 (13)	0.0061 (13)
C27	0.0437 (16)	0.0370 (17)	0.0205 (15)	0.0036 (14)	0.0053 (12)	0.0029 (14)
C28	0.0379 (13)	0.0261 (14)	0.0290 (14)	0.0035 (14)	0.0080 (11)	0.0041 (14)
C29	0.0394 (16)	0.0342 (16)	0.0240 (16)	0.0010 (13)	0.0013 (13)	0.0053 (13)
C30	0.0513 (19)	0.076 (3)	0.0222 (16)	0.0061 (18)	0.0056 (14)	0.0009 (17)
C31	0.0544 (18)	0.051 (2)	0.0296 (16)	−0.0086 (18)	0.0019 (14)	0.0020 (17)
C32	0.0548 (19)	0.0315 (17)	0.0286 (17)	−0.0016 (15)	0.0007 (15)	0.0032 (14)
C33	0.108 (3)	0.047 (2)	0.0354 (19)	−0.028 (2)	0.005 (2)	−0.0012 (18)
C34	0.057 (2)	0.069 (3)	0.073 (3)	−0.021 (2)	0.006 (2)	−0.011 (2)

Geometric parameters (Å, º) top

S1—C1	1.715 (3)	S2—C18	1.719 (3)
S1—C4	1.719 (3)	S2—C21	1.724 (3)
C1—C2	1.345 (5)	C18—C19	1.345 (4)
C1—H1	0.9300	C18—H18	0.9300
C2—C3	1.411 (5)	C19—C20	1.415 (4)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.364 (4)	C20—C21	1.368 (4)
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.449 (4)	C21—C22	1.445 (4)
C5—N1	1.264 (3)	C22—N2	1.269 (4)
C5—H5	0.9300	C22—H22	0.9300
N1—C6	1.427 (4)	N2—C23	1.437 (4)
C6—C11	1.398 (4)	C23—C24	1.398 (4)
C6—C7	1.419 (4)	C23—C28	1.409 (4)
C7—C8	1.387 (5)	C24—C25	1.385 (4)
C7—C12	1.515 (4)	C24—C29	1.526 (4)
C8—C9	1.379 (5)	C25—C26	1.393 (4)
C8—H8	0.9300	C25—H25	0.9300
C9—C10	1.374 (5)	C26—C27	1.381 (4)
C9—H9	0.9300	C26—H26	0.9300
C10—C11	1.392 (5)	C27—C28	1.395 (5)
C10—H10	0.9300	C27—H27	0.9300
C11—C15	1.527 (4)	C28—C32	1.517 (4)
C12—C14	1.498 (6)	C29—C30	1.511 (5)
C12—C13	1.514 (5)	C29—C31	1.518 (5)
C12—H12	0.9800	C29—H29	0.9800
C13—H13A	0.9600	C30—H30A	0.9600
C13—H13B	0.9600	C30—H30B	0.9600
C13—H13C	0.9600	C30—H30C	0.9600
C14—H14A	0.9600	C31—H31A	0.9600
C14—H14B	0.9600	C31—H31B	0.9600
C14—H14C	0.9600	C31—H31C	0.9600
C15—C17	1.517 (5)	C32—C33	1.519 (5)
C15—C16	1.533 (5)	C32—C34	1.530 (5)
C15—H15	0.9800	C32—H32	0.9800
C16—H16A	0.9600	C33—H33A	0.9600
C16—H16B	0.9600	C33—H33B	0.9600
C16—H16C	0.9600	C33—H33C	0.9600
C17—H17A	0.9600	C34—H34A	0.9600
C17—H17B	0.9600	C34—H34B	0.9600
C17—H17C	0.9600	C34—H34C	0.9600

C1—S1—C4	91.53 (16)	C18—S2—C21	91.46 (14)
C2—C1—S1	111.8 (3)	C19—C18—S2	112.3 (2)
C2—C1—H1	124.1	C19—C18—H18	123.8
S1—C1—H1	124.1	S2—C18—H18	123.8
C1—C2—C3	112.9 (3)	C18—C19—C20	112.3 (3)
C1—C2—H2	123.6	C18—C19—H19	123.8
C3—C2—H2	123.6	C20—C19—H19	123.8
C4—C3—C2	112.8 (3)	C21—C20—C19	113.2 (3)
C4—C3—H3	123.6	C21—C20—H20	123.4
C2—C3—H3	123.6	C19—C20—H20	123.4
C3—C4—C5	127.5 (3)	C20—C21—C22	127.3 (3)
C3—C4—S1	111.0 (2)	C20—C21—S2	110.7 (2)
C5—C4—S1	121.4 (2)	C22—C21—S2	121.9 (2)
N1—C5—C4	122.0 (3)	N2—C22—C21	122.8 (3)
N1—C5—H5	119.0	N2—C22—H22	118.6
C4—C5—H5	119.0	C21—C22—H22	118.6
C5—N1—C6	121.0 (3)	C22—N2—C23	117.8 (2)
C11—C6—C7	121.0 (3)	C24—C23—C28	121.8 (3)
C11—C6—N1	120.6 (2)	C24—C23—N2	119.5 (2)
C7—C6—N1	118.1 (2)	C28—C23—N2	118.6 (3)
C8—C7—C6	117.9 (3)	C25—C24—C23	118.1 (3)
C8—C7—C12	120.4 (2)	C25—C24—C29	120.8 (3)
C6—C7—C12	121.7 (3)	C23—C24—C29	120.8 (3)
C9—C8—C7	121.8 (3)	C24—C25—C26	121.3 (3)
C9—C8—H8	119.1	C24—C25—H25	119.3
C7—C8—H8	119.1	C26—C25—H25	119.3
C10—C9—C8	119.2 (3)	C27—C26—C25	119.6 (3)
C10—C9—H9	120.4	C27—C26—H26	120.2
C8—C9—H9	120.4	C25—C26—H26	120.2
C9—C10—C11	122.2 (3)	C26—C27—C28	121.3 (3)
C9—C10—H10	118.9	C26—C27—H27	119.3
C11—C10—H10	118.9	C28—C27—H27	119.3
C10—C11—C6	117.9 (3)	C27—C28—C23	117.7 (3)
C10—C11—C15	119.4 (3)	C27—C28—C32	121.5 (3)
C6—C11—C15	122.7 (3)	C23—C28—C32	120.8 (3)
C14—C12—C7	110.2 (3)	C30—C29—C31	110.7 (3)
C14—C12—C13	110.3 (4)	C30—C29—C24	109.5 (2)
C7—C12—C13	111.6 (3)	C31—C29—C24	114.1 (3)
C14—C12—H12	108.2	C30—C29—H29	107.4
C7—C12—H12	108.2	C31—C29—H29	107.4
C13—C12—H12	108.2	C24—C29—H29	107.4
C12—C13—H13A	109.5	C29—C30—H30A	109.5
C12—C13—H13B	109.5	C29—C30—H30B	109.5
H13A—C13—H13B	109.5	H30A—C30—H30B	109.5
C12—C13—H13C	109.5	C29—C30—H30C	109.5
H13A—C13—H13C	109.5	H30A—C30—H30C	109.5
H13B—C13—H13C	109.5	H30B—C30—H30C	109.5
C12—C14—H14A	109.5	C29—C31—H31A	109.5
C12—C14—H14B	109.5	C29—C31—H31B	109.5
H14A—C14—H14B	109.5	H31A—C31—H31B	109.5
C12—C14—H14C	109.5	C29—C31—H31C	109.5
H14A—C14—H14C	109.5	H31A—C31—H31C	109.5
H14B—C14—H14C	109.5	H31B—C31—H31C	109.5
C17—C15—C11	110.4 (3)	C28—C32—C33	113.5 (3)
C17—C15—C16	110.7 (3)	C28—C32—C34	110.4 (3)
C11—C15—C16	111.2 (3)	C33—C32—C34	110.6 (3)
C17—C15—H15	108.1	C28—C32—H32	107.4
C11—C15—H15	108.1	C33—C32—H32	107.4
C16—C15—H15	108.1	C34—C32—H32	107.4
C15—C16—H16A	109.5	C32—C33—H33A	109.5
C15—C16—H16B	109.5	C32—C33—H33B	109.5
H16A—C16—H16B	109.5	H33A—C33—H33B	109.5
C15—C16—H16C	109.5	C32—C33—H33C	109.5
H16A—C16—H16C	109.5	H33A—C33—H33C	109.5
H16B—C16—H16C	109.5	H33B—C33—H33C	109.5
C15—C17—H17A	109.5	C32—C34—H34A	109.5
C15—C17—H17B	109.5	C32—C34—H34B	109.5
H17A—C17—H17B	109.5	H34A—C34—H34B	109.5
C15—C17—H17C	109.5	C32—C34—H34C	109.5
H17A—C17—H17C	109.5	H34A—C34—H34C	109.5
H17B—C17—H17C	109.5	H34B—C34—H34C	109.5

C4—S1—C1—C2	0.4 (3)	C21—S2—C18—C19	0.1 (2)
S1—C1—C2—C3	−0.2 (4)	S2—C18—C19—C20	0.3 (3)
C1—C2—C3—C4	−0.2 (4)	C18—C19—C20—C21	−0.5 (4)
C2—C3—C4—C5	−176.0 (3)	C19—C20—C21—C22	−177.2 (3)
C2—C3—C4—S1	0.5 (3)	C19—C20—C21—S2	0.6 (3)
C1—S1—C4—C3	−0.5 (2)	C18—S2—C21—C20	−0.4 (2)
C1—S1—C4—C5	176.2 (2)	C18—S2—C21—C22	177.6 (2)
C3—C4—C5—N1	173.4 (3)	C20—C21—C22—N2	176.8 (3)
S1—C4—C5—N1	−2.8 (4)	S2—C21—C22—N2	−0.8 (4)
C4—C5—N1—C6	−177.8 (2)	C21—C22—N2—C23	−177.7 (2)
C5—N1—C6—C11	84.0 (3)	C22—N2—C23—C24	88.5 (3)
C5—N1—C6—C7	−102.3 (3)	C22—N2—C23—C28	−94.9 (3)
C11—C6—C7—C8	0.1 (4)	C28—C23—C24—C25	3.0 (4)
N1—C6—C7—C8	−173.5 (3)	N2—C23—C24—C25	179.5 (2)
C11—C6—C7—C12	−178.7 (3)	C28—C23—C24—C29	−172.0 (3)
N1—C6—C7—C12	7.6 (4)	N2—C23—C24—C29	4.5 (4)
C6—C7—C8—C9	1.0 (5)	C23—C24—C25—C26	−1.7 (4)
C12—C7—C8—C9	179.9 (3)	C29—C24—C25—C26	173.2 (3)
C7—C8—C9—C10	−0.5 (5)	C24—C25—C26—C27	−0.8 (4)
C8—C9—C10—C11	−1.4 (6)	C25—C26—C27—C28	2.2 (4)
C9—C10—C11—C6	2.5 (5)	C26—C27—C28—C23	−0.9 (4)
C9—C10—C11—C15	179.1 (3)	C26—C27—C28—C32	−178.1 (3)
C7—C6—C11—C10	−1.8 (4)	C24—C23—C28—C27	−1.7 (4)
N1—C6—C11—C10	171.7 (3)	N2—C23—C28—C27	−178.2 (3)
C7—C6—C11—C15	−178.3 (3)	C24—C23—C28—C32	175.5 (3)
N1—C6—C11—C15	−4.8 (5)	N2—C23—C28—C32	−1.0 (4)
C8—C7—C12—C14	−67.3 (4)	C25—C24—C29—C30	−97.0 (3)
C6—C7—C12—C14	111.6 (4)	C23—C24—C29—C30	77.8 (4)
C8—C7—C12—C13	55.6 (5)	C25—C24—C29—C31	27.7 (4)
C6—C7—C12—C13	−125.6 (4)	C23—C24—C29—C31	−157.5 (3)
C10—C11—C15—C17	−72.7 (4)	C27—C28—C32—C33	−23.4 (5)
C6—C11—C15—C17	103.7 (4)	C23—C28—C32—C33	159.5 (3)
C10—C11—C15—C16	50.5 (4)	C27—C28—C32—C34	101.4 (4)
C6—C11—C15—C16	−133.1 (3)	C23—C28—C32—C34	−75.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···N1	0.93	2.52	3.449 (8)	178

Experimental details

Crystal data
Chemical formula	C₁₇H₂₁NS
M_r	271.42
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	10.0877 (9), 14.275 (3), 11.4503 (9)
β (°)	109.651 (8)
V (Å³)	1552.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.51 × 0.43 × 0.33

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.884, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	2222, 2096, 2055
R_int	0.023
θ_max (°)	23.0
(sin θ/λ)_max (Å⁻¹)	0.549

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.079, 1.08
No. of reflections	2096
No. of parameters	353
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.19

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), SET4 (de Boer et al., 1984), MolEN (Enraf–Nonius, 1990), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Siemens, 1990).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···N1	0.93	2.519	3.449 (8)	178.4

Acknowledgements

The author thanks the Deutsche Forschungsgemeinschaft (SFB 436) for financial support.

References

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