1-[(4-tert-Butyl­phen­yl)sulfon­yl]-1H-benzimidazole

Abdireymov, K.B.; Mukhamedov, N.S.; Okmanov, R.Y.; Ayimbetov, M.J.; Shakhidoyatov, K.M.

doi:10.1107/S1600536811005551

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o709

doi:10.1107/S1600536811005551

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1-[(4-tert-Butylphenyl)sulfonyl]-1H-benzimidazole

K. B. Abdireymov,^a ^* N. S. Mukhamedov,^a R. Ya. Okmanov,^a M. J. Ayimbetov ^b and Kh. M. Shakhidoyatov ^a

^aS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan, and ^bKara-Kalpak State University, Acad. Abdirov Str. 1, Nukus 742000, Uzbekistan
^*Correspondence e-mail: abdireymovqudaybergen@mail.ru

(Received 10 February 2011; accepted 15 February 2011; online 26 February 2011)

The title compound, C₁₇H₁₈N₂O₂S, was synthesized by arylsulfonylation of 1-hydroxymethyl-1H-benzimidazole in the presence of triethylamine. The benzimidazole and benzene rings form a dihedral angle of 84.1 (1)°. The tert-butyl group was treated as rotationally disordered over two orientations in a 0.51 (2):0.49 (2) ratio. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link the molecules into chains propagating in [010].

Related literature

For the biological and pharmaceutical properties of benzimidazole derivatives, see: Koči et al. (2002 ); Matsuno et al. (2000 ); Garuti et al. (1999 ). For related structures, see: Rashid et al. (2006 , 2007 ). For the arylsulfonylation of benzimidazole derivatives, see: Abdireimov et al. (2010 ).

Experimental

Crystal data

C₁₇H₁₈N₂O₂S
M_r = 314.39
Monoclinic, P 2₁ /n
a = 12.142 (2) Å
b = 8.8940 (18) Å
c = 15.324 (3) Å
β = 96.78 (3)°
V = 1643.3 (6) Å³
Z = 4
Cu Kα radiation
μ = 1.82 mm⁻¹
T = 302 K
0.60 × 0.25 × 0.22 mm

Data collection

Stoe Stadi-4 four-circle diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.609, T_max = 0.670
2727 measured reflections
2429 independent reflections
1813 reflections with I > 2σ(I)
R_int = 0.044
θ_max = 60.0°
3 standard reflections every 60 min intensity decay: 5.2%

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.150
S = 1.12
2429 reflections
234 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O2ⁱ	0.93	2.56	3.430 (5)	156
C13—H13A⋯O1ⁱ	0.93	2.56	3.292 (5)	136
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: STADI4 (Stoe & Cie, 1997 ); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 1998 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005551/cv5052sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005551/cv5052Isup2.hkl

checkCIF report

Comment top

Benzimidazole derivatives are important heteroaromatic compounds which have attracted great attention due to their biological and pharmaceutical activities (Koči et al., 2002; Matsuno et al., 2000; Garuti et al., 1999). The title compound has been obtained by the reaction of hydroxymethyl-1H-benzimidazole with 4-tert-butilbenzolsulfochlorid in the presence of triethylamine (Abdireimov et al., 2010; see also Fig. 1), where occurs deformylation of oxymethyl groups. The structure of the final product was investigated by ¹H NMR-spectroscopy and X-ray diffraction.

The molecule (Fig. 2) consist of two flat fragments - benzimidazolic (N1/C2/N3/C3A–C7A) and benzolic (C8–C13) (r.m.s. deviation = 0.0082 and 0.0017 Å) ones, which form a dihedral angle of 84.1 (1)°. All bond lengths and angles are normal and comparable with those in related structures (Rashid et al., 2006, 2007). The tert-butyl group was rotationally disordered over two orientations with occupancies refined to 0.51 (2) and 0.49 (2), respectively.

In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into chains propagated in direction [010].

Related literature top

For the biological and pharmaceutical properties of benzimidazole derivatives, see: Koči et al. (2002); Matsuno et al. (2000); Garuti et al. (1999). For related structures, see: Rashid et al. (2006, 2007). For the arylsulfonylation of benzimidazole derivatives, see: Abdireimov et al. (2010).

Experimental top

To three-necked flask supplied with a mixer, containing solution of 2.32 g (10 mmol) 4-tert-butilbenzolsulfochloride in 15 ml acetone is added mixture of 1.48 g (10 mmol) 1-hydroxymethyl-1Hbenzimidazole and 1.01 g (10 mmol) triethylamine in 30 ml of acetone. The reaction mixture is mixed at room temperature for 4 h and acetone is evaporated. The rest of mass is washed by 100 ml of water and filtered, and recrystallized from benzine and received 2.61 g (76%) of title compound, m.p. 395–396 K.

The colorless crystals suitable for x-ray analysis have been grown from absolutized ethanol at room temperature.

¹H NMR (400 MHz, CDCl₃): 8.33 (1H,s, H-2), 7.85 (3H, m, H-4, 5, 6,), 7.71 (1H, dd, J═2.1, J═8.2 Hz H-7), 7.45 (2H, m, H-9, 13), 7.32 (2H, m, H-10, 12), 1.20 (9H, s, C(CH₃)₃).

Computing details top

Data collection: STADI4 (Stoe & Cie, 1997); cell refinement: STADI4 (Stoe & Cie, 1997); data reduction: X-RED (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 1998); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Reaction sequence.
	Fig. 2. The molecular structure of the title compound, showing the atomic numbering scheme. The displacement ellipsoids are drawn at the 30% probability level. Minor parts of the disordered atoms were omitted for clarity.

1-[(4-tert-Butylphenyl)sulfonyl]-1H-benzimidazole top

Crystal data top

C₁₇H₁₈N₂O₂S	F(000) = 664
M_r = 314.39	D_x = 1.271 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 395(1) K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54184 Å
a = 12.142 (2) Å	Cell parameters from 14 reflections
b = 8.8940 (18) Å	θ = 10–20°
c = 15.324 (3) Å	µ = 1.82 mm⁻¹
β = 96.78 (3)°	T = 302 K
V = 1643.3 (6) Å³	Prism, colourless
Z = 4	0.60 × 0.25 × 0.22 mm

Data collection top

Stoe Stadi-4 four-circle diffractometer	1813 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 60.0°, θ_min = 4.4°
Scan width (ω) = 1.56 – 1.80, scan ratio 2θ:ω = 1.00 I(Net) and sigma(I) calculated according to Blessing (1987)	h = −13→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
T_min = 0.609, T_max = 0.670	l = 0→17
2727 measured reflections	3 standard reflections every 60 min
2429 independent reflections	intensity decay: 5.2%

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)] = 0.058	H-atom parameters constrained
wR(F²) = 0.150	w = 1/[σ²(F_o²) + (0.0478P)² + 1.1618P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
2429 reflections	Δρ_max = 0.15 e Å⁻³
234 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0054 (4)

Crystal data top

C₁₇H₁₈N₂O₂S	V = 1643.3 (6) Å³
M_r = 314.39	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 12.142 (2) Å	µ = 1.82 mm⁻¹
b = 8.8940 (18) Å	T = 302 K
c = 15.324 (3) Å	0.60 × 0.25 × 0.22 mm
β = 96.78 (3)°

Data collection top

Stoe Stadi-4 four-circle diffractometer	1813 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.044
T_min = 0.609, T_max = 0.670	θ_max = 60.0°
2727 measured reflections	3 standard reflections every 60 min
2429 independent reflections	intensity decay: 5.2%

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.12	Δρ_max = 0.15 e Å⁻³
2429 reflections	Δρ_min = −0.27 e Å⁻³
234 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	Occ. (<1)
S1	0.15656 (9)	0.56256 (13)	0.30146 (7)	0.0817 (4)
O1	0.2287 (3)	0.6147 (4)	0.24143 (18)	0.1059 (11)
O2	0.0939 (3)	0.4275 (3)	0.2866 (2)	0.1116 (11)
N1	0.2366 (2)	0.5318 (4)	0.39620 (19)	0.0695 (8)
N3	0.2705 (3)	0.4528 (4)	0.5352 (3)	0.0882 (11)
C2	0.2092 (4)	0.4382 (5)	0.4623 (3)	0.0855 (12)
H2B	0.1509	0.3700	0.4542	0.103*
C3A	0.3453 (3)	0.5650 (4)	0.5199 (3)	0.0678 (10)
C4	0.4313 (4)	0.6232 (5)	0.5767 (3)	0.0857 (12)
H4A	0.4460	0.5875	0.6340	0.103*
C5	0.4939 (4)	0.7339 (6)	0.5467 (4)	0.0924 (13)
H5A	0.5514	0.7757	0.5845	0.111*
C6	0.4741 (4)	0.7862 (5)	0.4611 (4)	0.0907 (13)
H6A	0.5189	0.8618	0.4425	0.109*
C7	0.3901 (3)	0.7286 (4)	0.4032 (3)	0.0764 (11)
H7A	0.3773	0.7625	0.3455	0.092*
C7A	0.3259 (3)	0.6188 (4)	0.4344 (2)	0.0621 (9)
C8	0.0676 (3)	0.7078 (4)	0.3232 (2)	0.0593 (9)
C9	−0.0313 (3)	0.6758 (4)	0.3528 (2)	0.0639 (9)
H9A	−0.0507	0.5766	0.3627	0.077*
C10	−0.1020 (3)	0.7904 (4)	0.3678 (2)	0.0635 (9)
H10A	−0.1696	0.7674	0.3875	0.076*
C11	−0.0760 (3)	0.9392 (4)	0.3545 (2)	0.0542 (8)
C12	0.0251 (3)	0.9681 (4)	0.3244 (2)	0.0673 (10)
H12A	0.0450	1.0670	0.3146	0.081*
C13	0.0966 (3)	0.8541 (4)	0.3086 (2)	0.0672 (10)
H13A	0.1640	0.8759	0.2883	0.081*
C14	−0.1562 (3)	1.0652 (5)	0.3703 (3)	0.0709 (10)
C15	−0.2610 (16)	1.044 (3)	0.3059 (11)	0.131 (7)	0.51 (2)
H15A	−0.3100	1.1275	0.3104	0.197*	0.51 (2)
H15B	−0.2974	0.9526	0.3196	0.197*	0.51 (2)
H15C	−0.2413	1.0382	0.2471	0.197*	0.51 (2)
C16	−0.113 (2)	1.2215 (18)	0.361 (3)	0.234 (18)	0.51 (2)
H16A	−0.0440	1.2326	0.3985	0.351*	0.51 (2)
H16B	−0.1658	1.2926	0.3788	0.351*	0.51 (2)
H16C	−0.1015	1.2394	0.3015	0.351*	0.51 (2)
C17	−0.1958 (18)	1.047 (2)	0.4597 (8)	0.142 (10)	0.51 (2)
H17A	−0.1330	1.0447	0.5041	0.214*	0.51 (2)
H17B	−0.2367	0.9549	0.4613	0.214*	0.51 (2)
H17C	−0.2428	1.1302	0.4706	0.214*	0.51 (2)
C15A	−0.0948 (12)	1.1855 (16)	0.4249 (10)	0.093 (5)	0.49 (2)
H15D	−0.1469	1.2544	0.4454	0.140*	0.49 (2)
H15E	−0.0470	1.2386	0.3899	0.140*	0.49 (2)
H15F	−0.0511	1.1403	0.4743	0.140*	0.49 (2)
C16A	−0.248 (2)	1.013 (2)	0.415 (3)	0.233 (19)	0.49 (2)
H16D	−0.2963	1.0962	0.4239	0.350*	0.49 (2)
H16E	−0.2204	0.9706	0.4708	0.350*	0.49 (2)
H16F	−0.2894	0.9380	0.3797	0.350*	0.49 (2)
C17A	−0.192 (3)	1.141 (3)	0.2816 (11)	0.150 (10)	0.49 (2)
H17D	−0.2465	1.2174	0.2891	0.226*	0.49 (2)
H17E	−0.2240	1.0676	0.2403	0.226*	0.49 (2)
H17F	−0.1290	1.1865	0.2600	0.226*	0.49 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0854 (7)	0.0894 (8)	0.0698 (6)	0.0210 (6)	0.0072 (5)	−0.0219 (6)
O1	0.112 (2)	0.145 (3)	0.0660 (17)	0.044 (2)	0.0306 (16)	−0.0054 (18)
O2	0.116 (2)	0.087 (2)	0.126 (3)	0.0087 (19)	−0.012 (2)	−0.0552 (19)
N1	0.0673 (19)	0.069 (2)	0.0716 (19)	0.0118 (16)	0.0044 (16)	0.0041 (16)
N3	0.083 (2)	0.086 (3)	0.096 (3)	0.001 (2)	0.014 (2)	0.026 (2)
C2	0.080 (3)	0.067 (3)	0.112 (4)	0.000 (2)	0.020 (3)	0.016 (3)
C3A	0.061 (2)	0.068 (2)	0.075 (2)	0.0119 (19)	0.0132 (19)	0.008 (2)
C4	0.082 (3)	0.095 (3)	0.079 (3)	0.012 (3)	0.007 (2)	0.006 (2)
C5	0.071 (3)	0.094 (3)	0.111 (4)	0.004 (3)	0.003 (3)	−0.015 (3)
C6	0.073 (3)	0.075 (3)	0.128 (4)	−0.003 (2)	0.023 (3)	0.006 (3)
C7	0.075 (3)	0.070 (3)	0.087 (3)	0.012 (2)	0.024 (2)	0.019 (2)
C7A	0.059 (2)	0.059 (2)	0.070 (2)	0.0141 (18)	0.0141 (17)	0.0043 (18)
C8	0.057 (2)	0.070 (2)	0.0502 (19)	0.0035 (18)	0.0041 (15)	−0.0080 (17)
C9	0.060 (2)	0.058 (2)	0.071 (2)	−0.0046 (18)	0.0000 (18)	−0.0060 (18)
C10	0.050 (2)	0.071 (2)	0.069 (2)	−0.0058 (18)	0.0079 (16)	−0.0093 (19)
C11	0.0482 (18)	0.062 (2)	0.0502 (18)	−0.0012 (16)	−0.0024 (14)	−0.0048 (16)
C12	0.067 (2)	0.059 (2)	0.076 (2)	−0.0038 (19)	0.0100 (19)	0.0078 (19)
C13	0.058 (2)	0.081 (3)	0.065 (2)	−0.002 (2)	0.0149 (17)	0.005 (2)
C14	0.063 (2)	0.074 (3)	0.074 (2)	0.011 (2)	0.0002 (18)	−0.006 (2)
C15	0.100 (10)	0.177 (19)	0.106 (11)	0.076 (11)	−0.037 (8)	−0.032 (11)
C16	0.17 (2)	0.069 (9)	0.49 (6)	0.027 (10)	0.14 (3)	0.05 (2)
C17	0.20 (2)	0.153 (18)	0.071 (8)	0.102 (16)	0.023 (8)	−0.007 (8)
C15A	0.095 (7)	0.057 (8)	0.122 (9)	0.014 (7)	−0.010 (7)	−0.037 (7)
C16A	0.157 (18)	0.104 (11)	0.48 (5)	−0.015 (13)	0.23 (3)	−0.07 (2)
C17A	0.18 (2)	0.153 (18)	0.105 (10)	0.096 (16)	−0.050 (13)	−0.022 (11)

Geometric parameters (Å, º) top

S1—O1	1.421 (3)	C12—C13	1.375 (5)
S1—O2	1.426 (3)	C12—H12A	0.9300
S1—N1	1.671 (3)	C13—H13A	0.9300
S1—C8	1.742 (3)	C14—C16A	1.455 (17)
N1—C2	1.381 (5)	C14—C16	1.498 (17)
N1—C7A	1.402 (5)	C14—C15A	1.501 (12)
N3—C2	1.274 (5)	C14—C17	1.513 (15)
N3—C3A	1.387 (5)	C14—C15	1.527 (15)
C2—H2B	0.9300	C14—C17A	1.535 (18)
C3A—C4	1.379 (5)	C15—H15A	0.9600
C3A—C7A	1.389 (5)	C15—H15B	0.9600
C4—C5	1.357 (6)	C15—H15C	0.9600
C4—H4A	0.9300	C16—H16A	0.9600
C5—C6	1.386 (6)	C16—H16B	0.9600
C5—H5A	0.9300	C16—H16C	0.9600
C6—C7	1.369 (6)	C17—H17A	0.9600
C6—H6A	0.9300	C17—H17B	0.9600
C7—C7A	1.371 (5)	C17—H17C	0.9600
C7—H7A	0.9300	C15A—H15D	0.9600
C8—C9	1.363 (5)	C15A—H15E	0.9600
C8—C13	1.373 (5)	C15A—H15F	0.9600
C9—C10	1.369 (5)	C16A—H16D	0.9600
C9—H9A	0.9300	C16A—H16E	0.9600
C10—C11	1.381 (5)	C16A—H16F	0.9600
C10—H10A	0.9300	C17A—H17D	0.9600
C11—C12	1.385 (5)	C17A—H17E	0.9600
C11—C14	1.523 (5)	C17A—H17F	0.9600

O1—S1—O2	122.0 (2)	C13—C12—H12A	119.2
O1—S1—N1	106.03 (18)	C11—C12—H12A	119.2
O2—S1—N1	104.21 (19)	C8—C13—C12	119.4 (3)
O1—S1—C8	109.00 (19)	C8—C13—H13A	120.3
O2—S1—C8	108.89 (18)	C12—C13—H13A	120.3
N1—S1—C8	105.39 (15)	C16A—C14—C15A	109.0 (13)
C2—N1—C7A	105.5 (3)	C16—C14—C17	109.4 (14)
C2—N1—S1	124.7 (3)	C16A—C14—C11	112.5 (8)
C7A—N1—S1	127.9 (3)	C16—C14—C11	115.5 (8)
C2—N3—C3A	104.6 (4)	C15A—C14—C11	109.1 (6)
N3—C2—N1	114.5 (4)	C17—C14—C11	110.1 (7)
N3—C2—H2B	122.7	C16—C14—C15	109.3 (12)
N1—C2—H2B	122.7	C17—C14—C15	104.1 (10)
C4—C3A—N3	128.7 (4)	C11—C14—C15	107.8 (7)
C4—C3A—C7A	119.9 (4)	C16A—C14—C17A	113.7 (12)
N3—C3A—C7A	111.4 (4)	C15A—C14—C17A	104.5 (10)
C5—C4—C3A	118.1 (4)	C11—C14—C17A	107.7 (7)
C5—C4—H4A	120.9	C14—C15—H15A	109.5
C3A—C4—H4A	120.9	C14—C15—H15B	109.5
C4—C5—C6	121.5 (4)	C14—C15—H15C	109.5
C4—C5—H5A	119.2	C14—C16—H16A	109.5
C6—C5—H5A	119.2	C14—C16—H16B	109.5
C7—C6—C5	121.4 (4)	C14—C16—H16C	109.5
C7—C6—H6A	119.3	C14—C17—H17A	109.5
C5—C6—H6A	119.3	C14—C17—H17B	109.5
C6—C7—C7A	116.8 (4)	C14—C17—H17C	109.5
C6—C7—H7A	121.6	C14—C15A—H15D	109.5
C7A—C7—H7A	121.6	C14—C15A—H15E	109.5
C7—C7A—C3A	122.3 (4)	H15D—C15A—H15E	109.5
C7—C7A—N1	133.7 (4)	C14—C15A—H15F	109.5
C3A—C7A—N1	104.0 (3)	H15D—C15A—H15F	109.5
C9—C8—C13	120.4 (3)	H15E—C15A—H15F	109.5
C9—C8—S1	120.0 (3)	C14—C16A—H16D	109.5
C13—C8—S1	119.7 (3)	C14—C16A—H16E	109.5
C8—C9—C10	119.6 (3)	H16D—C16A—H16E	109.5
C8—C9—H9A	120.2	C14—C16A—H16F	109.5
C10—C9—H9A	120.2	H16D—C16A—H16F	109.5
C9—C10—C11	122.0 (3)	H16E—C16A—H16F	109.5
C9—C10—H10A	119.0	C14—C17A—H17D	109.5
C11—C10—H10A	119.0	C14—C17A—H17E	109.5
C10—C11—C12	117.0 (3)	H17D—C17A—H17E	109.5
C10—C11—C14	121.3 (3)	C14—C17A—H17F	109.5
C12—C11—C14	121.7 (3)	H17D—C17A—H17F	109.5
C13—C12—C11	121.7 (3)	H17E—C17A—H17F	109.5

O1—S1—N1—C2	−158.3 (3)	O2—S1—C8—C9	22.1 (3)
O2—S1—N1—C2	−28.4 (4)	N1—S1—C8—C9	−89.2 (3)
C8—S1—N1—C2	86.2 (3)	O1—S1—C8—C13	−21.3 (3)
O1—S1—N1—C7A	39.6 (4)	O2—S1—C8—C13	−156.6 (3)
O2—S1—N1—C7A	169.5 (3)	N1—S1—C8—C13	92.1 (3)
C8—S1—N1—C7A	−75.9 (3)	C13—C8—C9—C10	0.2 (5)
C3A—N3—C2—N1	0.6 (5)	S1—C8—C9—C10	−178.5 (3)
C7A—N1—C2—N3	−1.4 (5)	C8—C9—C10—C11	−0.5 (5)
S1—N1—C2—N3	−166.9 (3)	C9—C10—C11—C12	0.5 (5)
C2—N3—C3A—C4	−178.8 (4)	C9—C10—C11—C14	179.2 (3)
C2—N3—C3A—C7A	0.5 (5)	C10—C11—C12—C13	−0.2 (5)
N3—C3A—C4—C5	−179.9 (4)	C14—C11—C12—C13	−178.8 (3)
C7A—C3A—C4—C5	0.8 (6)	C9—C8—C13—C12	0.1 (5)
C3A—C4—C5—C6	−1.2 (7)	S1—C8—C13—C12	178.8 (3)
C4—C5—C6—C7	0.3 (7)	C11—C12—C13—C8	−0.1 (5)
C5—C6—C7—C7A	0.9 (6)	C10—C11—C14—C16A	10.7 (19)
C6—C7—C7A—C3A	−1.2 (5)	C12—C11—C14—C16A	−170.7 (19)
C6—C7—C7A—N1	−178.1 (4)	C10—C11—C14—C16	174 (2)
C4—C3A—C7A—C7	0.4 (6)	C12—C11—C14—C16	−7 (2)
N3—C3A—C7A—C7	−179.0 (3)	C10—C11—C14—C15A	131.8 (8)
C4—C3A—C7A—N1	178.0 (3)	C12—C11—C14—C15A	−49.7 (8)
N3—C3A—C7A—N1	−1.3 (4)	C10—C11—C14—C17	49.9 (10)
C2—N1—C7A—C7	178.8 (4)	C12—C11—C14—C17	−131.5 (10)
S1—N1—C7A—C7	−16.3 (6)	C10—C11—C14—C15	−63.0 (13)
C2—N1—C7A—C3A	1.6 (4)	C12—C11—C14—C15	115.6 (13)
S1—N1—C7A—C3A	166.4 (3)	C10—C11—C14—C17A	−115.3 (15)
O1—S1—C8—C9	157.3 (3)	C12—C11—C14—C17A	63.2 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2ⁱ	0.93	2.56	3.430 (5)	156
C13—H13A···O1ⁱ	0.93	2.56	3.292 (5)	136

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₂S
M_r	314.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	302
a, b, c (Å)	12.142 (2), 8.8940 (18), 15.324 (3)
β (°)	96.78 (3)
V (Å³)	1643.3 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.82
Crystal size (mm)	0.60 × 0.25 × 0.22

Data collection
Diffractometer	Stoe Stadi-4 four-circle diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.609, 0.670
No. of measured, independent and observed [I > 2σ(I)] reflections	2727, 2429, 1813
R_int	0.044
θ_max (°)	60.0
(sin θ/λ)_max (Å⁻¹)	0.562

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.150, 1.12
No. of reflections	2429
No. of parameters	234
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.27

Computer programs: STADI4 (Stoe & Cie, 1997), X-RED (Stoe & Cie, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Bruker, 1998), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2ⁱ	0.93	2.558	3.430 (5)	156
C13—H13A···O1ⁱ	0.93	2.560	3.292 (5)	136

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant Nos. FA-F3-T045 & FA-A6-T114).

References

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