Benzyl 2-(benzylsulfanyl)benzoate.

In the title compound, C(21)H(18)O(2)S, the central aromatic ring makes dihedral angles of 5.86 (12) and 72.02 (6)° with the rings of the terminal O-benzyl and S-benzyl groups, respectively. The dihedral angle between the peripheral phenyl rings is 66.16 (6)°. In the crystal, mol-ecules are linked by pairs of C-H⋯O hydrogen bonds, forming inversion dimers. These dimers are linked via C-H⋯π inter-actions, forming a three-dimensional network.

Related literature

For related structures, see: Radić et al. (2012 ▶); Lucena et al. (1996 ▶); Sillanpää et al. (1994 ▶); Alhadi et al. (2010 ▶). For the biological activity of thio­salicylic acid derivatives, see: Bernardelli et al. (2005 ▶); Halaschek-Wiener et al. (2003 ▶); Sadao et al. (2000 ▶).

Experimental

Crystal data

C21H18O2S

M = 334.41

Triclinic,

a = 5.6957 (3) Å

b = 12.1117 (11) Å

c = 13.0813 (11) Å

α = 72.748 (8)°

β = 86.477 (6)°

γ = 89.941 (6)°

V = 860.04 (12) Å3

Z = 2

Cu Kα radiation

μ = 1.74 mm−1

T = 293 K

0.11 × 0.10 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur Gemini Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2012 ▶) T min = 0.944, T max = 1.000

5368 measured reflections

3299 independent reflections

2554 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.113

S = 1.04

3299 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2012 ▶); 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: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶), PLATON (Spek, 2009) ▶ and PARST (Nardelli, 1995 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813001761/rz5036sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001761/rz5036Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001761/rz5036Isup3.cml

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

C21H18O2S	Z = 2
Mr = 334.41	F(000) = 352
Triclinic, P1	Dx = 1.291 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 5.6957 (3) Å	Cell parameters from 2123 reflections
b = 12.1117 (11) Å	θ = 3.5–72.3°
c = 13.0813 (11) Å	µ = 1.74 mm−1
α = 72.748 (8)°	T = 293 K
β = 86.477 (6)°	Prism, colourless
γ = 89.941 (6)°	0.11 × 0.10 × 0.05 mm
V = 860.04 (12) Å3

Oxford Diffraction Xcalibur Gemini Sapphire3 diffractometer	3299 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2554 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 16.3280 pixels mm-1	θmax = 72.4°, θmin = 3.6°
ω scans	h = −5→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2012)	k = −14→14
Tmin = 0.944, Tmax = 1.000	l = −16→15
5368 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0493P)2 + 0.0651P] where P = (Fo2 + 2Fc2)/3
3299 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Experimental. IR (KBr, cm-1): 3414, 3061, 2920, 2648, 2559, 1674, 1584, 1562, 1463, 1412, 1317, 1272, 1255, 1154, 1062, 1046, 897, 743, 711, 652, 551. 1H NMR (200 MHz, CDCl3, δ p.p.m.): 4.11 (s, 2H, C15H2), 5.45 (s, 2H, C8H2), 7.00–7.93 (m, 17H, Ar and bz). 13C NMR (50 MHz, DMSO-d6, δ p.p.m.): 38.5 (C15H2), 68.3 (C8H2) 125.0; 126.3; 126.8; 127.0; 127.2; 127.5; 127.8; 127.9; 128.1; 128.3; 128.8; 128.9, 129.3; 130.2; 133.5; 139.5; 141.7; 142.3 (Ar and bz), 166.8 (COObz).

	x	y	z	Uiso*/Ueq
S1	0.60616 (9)	0.22258 (5)	0.48163 (4)	0.06178 (18)
O1	0.1278 (2)	0.47589 (12)	0.28903 (10)	0.0595 (4)
O2	0.2518 (3)	0.37675 (15)	0.44697 (11)	0.0859 (6)
C1	0.2696 (3)	0.40163 (17)	0.35128 (15)	0.0549 (5)
C2	0.4509 (3)	0.35644 (16)	0.28855 (14)	0.0519 (4)
C3	0.6149 (3)	0.27491 (16)	0.34054 (14)	0.0519 (4)
C4	0.7850 (4)	0.23806 (19)	0.27595 (16)	0.0632 (5)
H4	0.8945	0.1838	0.3081	0.076*
C5	0.7919 (4)	0.2808 (2)	0.16621 (17)	0.0728 (6)
H5	0.9072	0.2555	0.1253	0.087*
C6	0.6324 (4)	0.3601 (2)	0.11575 (17)	0.0743 (6)
H6	0.6388	0.3885	0.0413	0.089*
C7	0.4622 (4)	0.39694 (19)	0.17718 (15)	0.0650 (5)
H7	0.3525	0.4501	0.1433	0.078*
C8	−0.0440 (4)	0.53023 (19)	0.34328 (15)	0.0602 (5)
H8A	0.0348	0.5751	0.3817	0.072*
H8B	−0.1426	0.4718	0.3946	0.072*
C9	−0.1923 (3)	0.60777 (16)	0.26112 (15)	0.0522 (4)
C10	−0.1380 (4)	0.6363 (2)	0.15204 (16)	0.0659 (6)
H10	−0.0031	0.6073	0.1264	0.079*
C11	−0.2821 (4)	0.7076 (2)	0.08082 (17)	0.0725 (6)
H11	−0.2437	0.7260	0.0075	0.087*
C12	−0.4810 (4)	0.7514 (2)	0.11702 (18)	0.0712 (6)
H12	−0.5780	0.7990	0.0686	0.085*
C13	−0.5362 (4)	0.7247 (2)	0.22537 (18)	0.0678 (6)
H13	−0.6698	0.7552	0.2505	0.081*
C14	−0.3935 (3)	0.65252 (18)	0.29709 (16)	0.0592 (5)
H14	−0.4332	0.6339	0.3703	0.071*
C15	0.8417 (4)	0.11867 (19)	0.50644 (16)	0.0637 (5)
H15A	0.8106	0.0571	0.4754	0.076*
H15B	0.9904	0.1561	0.4746	0.076*
C16	0.8515 (3)	0.07081 (16)	0.62584 (15)	0.0555 (5)
C17	0.6840 (4)	−0.0071 (2)	0.68695 (18)	0.0715 (6)
H17	0.5632	−0.0315	0.6536	0.086*
C18	0.6927 (4)	−0.0493 (2)	0.79649 (19)	0.0817 (7)
H18	0.5787	−0.1022	0.8364	0.098*
C19	0.8689 (4)	−0.0138 (2)	0.84739 (19)	0.0757 (6)
H19	0.8743	−0.0418	0.9215	0.091*
C20	1.0364 (4)	0.0634 (2)	0.78757 (19)	0.0746 (6)
H20	1.1571	0.0872	0.8214	0.090*
C21	1.0283 (4)	0.10629 (19)	0.67754 (17)	0.0641 (5)
H21	1.1423	0.1594	0.6380	0.077*

	U11	U22	U33	U12	U13	U23
S1	0.0688 (3)	0.0641 (3)	0.0475 (3)	0.0269 (2)	−0.0004 (2)	−0.0098 (2)
O1	0.0647 (8)	0.0623 (8)	0.0502 (7)	0.0208 (7)	−0.0064 (6)	−0.0145 (6)
O2	0.0995 (12)	0.1023 (13)	0.0475 (8)	0.0567 (10)	−0.0012 (7)	−0.0103 (8)
C1	0.0607 (11)	0.0530 (11)	0.0481 (10)	0.0107 (9)	−0.0047 (8)	−0.0106 (8)
C2	0.0601 (11)	0.0465 (10)	0.0469 (10)	0.0058 (8)	0.0000 (8)	−0.0111 (8)
C3	0.0570 (11)	0.0489 (10)	0.0483 (10)	0.0060 (8)	0.0028 (8)	−0.0136 (8)
C4	0.0660 (12)	0.0638 (13)	0.0567 (11)	0.0154 (10)	0.0050 (9)	−0.0152 (9)
C5	0.0790 (15)	0.0769 (15)	0.0615 (13)	0.0124 (12)	0.0148 (10)	−0.0229 (11)
C6	0.0987 (17)	0.0748 (15)	0.0450 (11)	0.0102 (13)	0.0089 (11)	−0.0139 (10)
C7	0.0794 (14)	0.0618 (13)	0.0501 (11)	0.0136 (11)	−0.0039 (10)	−0.0109 (9)
C8	0.0645 (12)	0.0638 (12)	0.0502 (11)	0.0173 (10)	−0.0028 (9)	−0.0138 (9)
C9	0.0542 (10)	0.0489 (10)	0.0523 (10)	0.0059 (8)	−0.0050 (8)	−0.0129 (8)
C10	0.0618 (12)	0.0783 (15)	0.0537 (11)	0.0165 (11)	−0.0007 (9)	−0.0142 (10)
C11	0.0755 (14)	0.0837 (16)	0.0506 (11)	0.0134 (12)	−0.0052 (10)	−0.0077 (10)
C12	0.0655 (13)	0.0764 (15)	0.0673 (14)	0.0172 (11)	−0.0186 (10)	−0.0120 (11)
C13	0.0591 (12)	0.0716 (14)	0.0738 (14)	0.0181 (10)	−0.0061 (10)	−0.0228 (11)
C14	0.0609 (12)	0.0636 (12)	0.0546 (11)	0.0099 (10)	−0.0031 (9)	−0.0202 (9)
C15	0.0637 (12)	0.0635 (12)	0.0621 (12)	0.0257 (10)	−0.0048 (9)	−0.0160 (10)
C16	0.0553 (11)	0.0490 (10)	0.0615 (12)	0.0180 (9)	−0.0052 (9)	−0.0150 (9)
C17	0.0682 (13)	0.0626 (13)	0.0766 (15)	0.0004 (11)	−0.0176 (11)	−0.0073 (11)
C18	0.0813 (16)	0.0699 (15)	0.0762 (16)	−0.0043 (12)	−0.0062 (12)	0.0059 (12)
C19	0.0878 (17)	0.0730 (15)	0.0603 (13)	0.0167 (13)	−0.0134 (12)	−0.0091 (11)
C20	0.0734 (15)	0.0783 (16)	0.0769 (15)	0.0095 (12)	−0.0201 (12)	−0.0272 (13)
C21	0.0563 (12)	0.0637 (13)	0.0717 (14)	0.0039 (10)	−0.0022 (10)	−0.0197 (10)

S1—C3	1.7623 (19)	C10—H10	0.9300
S1—C15	1.8159 (18)	C11—C12	1.368 (3)
O1—C1	1.331 (2)	C11—H11	0.9300
O1—C8	1.444 (2)	C12—C13	1.373 (3)
O2—C1	1.195 (2)	C12—H12	0.9300
C1—C2	1.483 (3)	C13—C14	1.382 (3)
C2—C7	1.390 (2)	C13—H13	0.9300
C2—C3	1.410 (3)	C14—H14	0.9300
C3—C4	1.405 (2)	C15—C16	1.501 (3)
C4—C5	1.372 (3)	C15—H15A	0.9700
C4—H4	0.9300	C15—H15B	0.9700
C5—C6	1.371 (3)	C16—C17	1.379 (3)
C5—H5	0.9300	C16—C21	1.383 (3)
C6—C7	1.379 (3)	C17—C18	1.375 (3)
C6—H6	0.9300	C17—H17	0.9300
C7—H7	0.9300	C18—C19	1.375 (3)
C8—C9	1.504 (2)	C18—H18	0.9300
C8—H8A	0.9700	C19—C20	1.368 (3)
C8—H8B	0.9700	C19—H19	0.9300
C9—C10	1.380 (3)	C20—C21	1.381 (3)
C9—C14	1.383 (3)	C20—H20	0.9300
C10—C11	1.379 (3)	C21—H21	0.9300
C3—S1—C15	103.19 (9)	C12—C11—H11	119.7
C1—O1—C8	116.17 (14)	C10—C11—H11	119.7
O2—C1—O1	122.68 (18)	C11—C12—C13	119.5 (2)
O2—C1—C2	124.83 (17)	C11—C12—H12	120.2
O1—C1—C2	112.48 (16)	C13—C12—H12	120.2
C7—C2—C3	119.66 (17)	C12—C13—C14	120.1 (2)
C7—C2—C1	119.51 (17)	C12—C13—H13	120.0
C3—C2—C1	120.82 (16)	C14—C13—H13	120.0
C4—C3—C2	117.65 (17)	C13—C14—C9	120.71 (19)
C4—C3—S1	121.64 (15)	C13—C14—H14	119.6
C2—C3—S1	120.71 (14)	C9—C14—H14	119.6
C5—C4—C3	121.03 (19)	C16—C15—S1	107.11 (13)
C5—C4—H4	119.5	C16—C15—H15A	110.3
C3—C4—H4	119.5	S1—C15—H15A	110.3
C6—C5—C4	121.3 (2)	C16—C15—H15B	110.3
C6—C5—H5	119.4	S1—C15—H15B	110.3
C4—C5—H5	119.4	H15A—C15—H15B	108.5
C5—C6—C7	118.9 (2)	C17—C16—C21	118.3 (2)
C5—C6—H6	120.5	C17—C16—C15	121.5 (2)
C7—C6—H6	120.5	C21—C16—C15	120.2 (2)
C6—C7—C2	121.5 (2)	C18—C17—C16	121.0 (2)
C6—C7—H7	119.3	C18—C17—H17	119.5
C2—C7—H7	119.3	C16—C17—H17	119.5
O1—C8—C9	108.69 (15)	C19—C18—C17	120.4 (2)
O1—C8—H8A	110.0	C19—C18—H18	119.8
C9—C8—H8A	110.0	C17—C18—H18	119.8
O1—C8—H8B	110.0	C20—C19—C18	119.1 (2)
C9—C8—H8B	110.0	C20—C19—H19	120.4
H8A—C8—H8B	108.3	C18—C19—H19	120.4
C10—C9—C14	118.49 (17)	C19—C20—C21	120.8 (2)
C10—C9—C8	123.42 (17)	C19—C20—H20	119.6
C14—C9—C8	118.09 (17)	C21—C20—H20	119.6
C11—C10—C9	120.55 (19)	C20—C21—C16	120.4 (2)
C11—C10—H10	119.7	C20—C21—H21	119.8
C9—C10—H10	119.7	C16—C21—H21	119.8
C12—C11—C10	120.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2i	0.93	2.63	3.408 (3)	142
C4—H4···Cg3ii	0.93	3.11	3.846 (3)	137
C13—H13···Cg3i	0.93	2.88	3.653 (3)	141
C18—H18···Cg1iii	0.93	3.20	3.820 (3)	126
C20—H20···Cg2iv	0.93	2.96	3.651 (3)	132

Table 1

Geometry of hydrogen bonds and weak C—H⋯π interactions (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C2–C7, C9–C14 and C16–C21 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2i	0.93	2.63	3.408 (3)	142
C4—H4⋯Cg3ii	0.93	3.11	3.846 (3)	137
C13—H13⋯Cg3i	0.93	2.88	3.653 (3)	141
C18—H18⋯Cg1iii	0.93	3.20	3.820 (3)	126
C20—H20⋯Cg2iv	0.93	2.96	3.651 (3)	132

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .