2-[(3,5-Di-tert-butyl-4-hy-droxy-benz-yl)sulfan-yl]benzoic acid.

In the title compound, C(22)H(28)O(3)S, the dihedral angle between the two aromatic rings is 80.56 (6)°. The hy-droxy group is shielded by the two sterically hindered tert-butyl groups and therefore is not involved in any hydrogen bonding. The C-O-H fragment is coplanar with the aromatic ring, the dihedral angle between them being 7(5)°. In the crystal structure, pairs of mol-ecules are hydrogen bonded across crystallographic centers of symmetry.

Related literature

For a similar structure based on nicotinic acid, see: Mansor et al. (2008 ▶).

Experimental

Crystal data

C22H28O3S

M = 372.50

Monoclinic,

a = 18.1496 (4) Å

b = 5.6863 (1) Å

c = 20.2159 (4) Å

β = 101.172 (1)°

V = 2046.83 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 296 K

0.35 × 0.28 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.941, T max = 0.969

15313 measured reflections

3610 independent reflections

2477 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.123

S = 1.02

3610 reflections

247 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810023731/pk2249sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023731/pk2249Isup2.hkl

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

C22H28O3S	F(000) = 800
Mr = 372.50	Dx = 1.209 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2170 reflections
a = 18.1496 (4) Å	θ = 2.2–21.4°
b = 5.6863 (1) Å	µ = 0.18 mm−1
c = 20.2159 (4) Å	T = 296 K
β = 101.172 (1)°	Block, colourless
V = 2046.83 (7) Å3	0.35 × 0.28 × 0.18 mm
Z = 4

Bruker APEXII CCD diffractometer	3610 independent reflections
Radiation source: fine-focus sealed tube	2477 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→21
Tmin = 0.941, Tmax = 0.969	k = −6→6
15313 measured reflections	l = −24→24

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0518P)2 + 0.6688P] where P = (Fo2 + 2Fc2)/3
3610 reflections	(Δ/σ)max < 0.001
247 parameters	Δρmax = 0.32 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.08318 (3)	0.07380 (12)	0.38838 (3)	0.0556 (2)
O1	−0.08616 (10)	−0.4044 (4)	0.44667 (10)	0.0713 (6)
H1	−0.0691 (18)	−0.500 (5)	0.4773 (14)	0.107*
O2	0.03143 (10)	−0.2849 (3)	0.45796 (9)	0.0722 (6)
H3	0.437 (2)	0.532 (6)	0.4727 (18)	0.108*
O3	0.42604 (9)	0.4524 (3)	0.44311 (8)	0.0570 (5)
C1	−0.03435 (13)	−0.2647 (5)	0.43156 (12)	0.0511 (6)
C2	−0.06278 (12)	−0.0867 (4)	0.37992 (11)	0.0455 (5)
C3	−0.13987 (13)	−0.0776 (5)	0.35422 (12)	0.0560 (6)
H3A	−0.1715	−0.1827	0.3704	0.067*
C4	−0.17013 (14)	0.0820 (5)	0.30591 (13)	0.0602 (7)
H4	−0.2217	0.0869	0.2898	0.072*
C5	−0.12312 (14)	0.2351 (5)	0.28141 (13)	0.0617 (7)
H5	−0.1431	0.3419	0.2478	0.074*
C6	−0.04738 (14)	0.2318 (5)	0.30594 (12)	0.0555 (6)
H6	−0.0168	0.3374	0.2887	0.067*
C7	−0.01457 (12)	0.0736 (4)	0.35630 (11)	0.0453 (5)
C8	0.11580 (13)	0.3226 (4)	0.34536 (13)	0.0551 (6)
H8A	0.1071	0.2936	0.2972	0.066*
H8B	0.0887	0.4637	0.3532	0.066*
C9	0.19819 (13)	0.3541 (4)	0.37237 (12)	0.0476 (6)
C10	0.25124 (13)	0.2638 (4)	0.33862 (11)	0.0482 (6)
H10	0.2348	0.1782	0.2993	0.058*
C11	0.32779 (12)	0.2952 (4)	0.36066 (11)	0.0438 (5)
C12	0.34993 (12)	0.4227 (4)	0.42063 (11)	0.0424 (5)
C13	0.29827 (13)	0.5169 (4)	0.45709 (11)	0.0448 (5)
C14	0.22284 (13)	0.4794 (4)	0.43102 (12)	0.0506 (6)
H14	0.1874	0.5410	0.4539	0.061*
C15	0.32235 (14)	0.6534 (4)	0.52338 (12)	0.0545 (6)
C16	0.25557 (18)	0.7412 (8)	0.55221 (18)	0.1132 (14)
H16A	0.2253	0.8436	0.5202	0.170*
H16B	0.2735	0.8257	0.5933	0.170*
H16C	0.2259	0.6096	0.5613	0.170*
C17	0.3697 (2)	0.4965 (6)	0.57768 (14)	0.0901 (10)
H17A	0.3393	0.3695	0.5886	0.135*
H17B	0.3876	0.5883	0.6174	0.135*
H17C	0.4117	0.4342	0.5609	0.135*
C18	0.36869 (19)	0.8726 (5)	0.51428 (16)	0.0828 (9)
H18A	0.4140	0.8260	0.5000	0.124*
H18B	0.3812	0.9555	0.5563	0.124*
H18C	0.3399	0.9734	0.4808	0.124*
C19	0.38448 (14)	0.1959 (4)	0.31979 (11)	0.0518 (6)
C20	0.34466 (17)	0.0547 (6)	0.25871 (14)	0.0856 (10)
H20A	0.3111	0.1559	0.2290	0.128*
H20B	0.3166	−0.0712	0.2736	0.128*
H20C	0.3813	−0.0092	0.2352	0.128*
C21	0.42732 (18)	0.3964 (5)	0.29384 (16)	0.0828 (10)
H21A	0.4538	0.4857	0.3313	0.124*
H21B	0.3925	0.4970	0.2651	0.124*
H21C	0.4625	0.3326	0.2688	0.124*
C22	0.43946 (16)	0.0255 (5)	0.36205 (14)	0.0700 (8)
H22A	0.4747	−0.0302	0.3358	0.105*
H22B	0.4123	−0.1054	0.3754	0.105*
H22C	0.4660	0.1050	0.4015	0.105*

	U11	U22	U33	U12	U13	U23
S1	0.0401 (4)	0.0669 (4)	0.0595 (4)	−0.0046 (3)	0.0088 (3)	0.0124 (3)
O1	0.0490 (11)	0.0898 (15)	0.0741 (13)	−0.0145 (10)	0.0098 (9)	0.0283 (11)
O2	0.0433 (11)	0.0890 (14)	0.0831 (13)	−0.0060 (9)	0.0095 (9)	0.0368 (11)
O3	0.0446 (10)	0.0721 (12)	0.0559 (11)	−0.0047 (8)	0.0137 (8)	−0.0186 (9)
C1	0.0431 (15)	0.0646 (16)	0.0484 (14)	−0.0046 (12)	0.0156 (11)	0.0040 (12)
C2	0.0401 (13)	0.0562 (14)	0.0413 (12)	0.0000 (11)	0.0108 (10)	−0.0043 (11)
C3	0.0454 (15)	0.0684 (17)	0.0564 (15)	−0.0010 (12)	0.0152 (12)	−0.0016 (14)
C4	0.0394 (14)	0.0803 (19)	0.0595 (16)	0.0066 (13)	0.0060 (12)	−0.0020 (15)
C5	0.0558 (17)	0.0677 (18)	0.0595 (16)	0.0139 (14)	0.0058 (13)	0.0074 (14)
C6	0.0488 (15)	0.0601 (16)	0.0574 (15)	0.0003 (12)	0.0102 (12)	0.0096 (13)
C7	0.0415 (13)	0.0538 (14)	0.0420 (12)	0.0015 (11)	0.0112 (10)	−0.0032 (11)
C8	0.0468 (15)	0.0589 (16)	0.0610 (16)	−0.0042 (12)	0.0136 (12)	0.0061 (12)
C9	0.0458 (14)	0.0485 (14)	0.0505 (14)	−0.0057 (11)	0.0142 (11)	0.0037 (11)
C10	0.0532 (15)	0.0498 (14)	0.0424 (13)	−0.0057 (11)	0.0112 (11)	−0.0051 (11)
C11	0.0470 (14)	0.0464 (13)	0.0405 (12)	−0.0016 (10)	0.0151 (10)	−0.0006 (10)
C12	0.0410 (13)	0.0451 (13)	0.0435 (12)	−0.0036 (10)	0.0139 (10)	−0.0015 (10)
C13	0.0505 (14)	0.0458 (13)	0.0421 (12)	−0.0036 (10)	0.0190 (11)	−0.0026 (10)
C14	0.0503 (15)	0.0532 (15)	0.0543 (15)	−0.0017 (11)	0.0254 (12)	−0.0018 (12)
C15	0.0667 (17)	0.0565 (15)	0.0455 (14)	−0.0068 (12)	0.0235 (12)	−0.0099 (12)
C16	0.088 (2)	0.158 (4)	0.105 (3)	−0.013 (2)	0.047 (2)	−0.074 (3)
C17	0.128 (3)	0.094 (2)	0.0485 (17)	−0.005 (2)	0.0170 (18)	−0.0055 (16)
C18	0.106 (3)	0.071 (2)	0.076 (2)	−0.0196 (17)	0.0289 (18)	−0.0233 (16)
C19	0.0579 (15)	0.0574 (15)	0.0440 (14)	0.0023 (12)	0.0197 (11)	−0.0077 (12)
C20	0.084 (2)	0.114 (3)	0.0609 (18)	0.0135 (18)	0.0185 (16)	−0.0377 (18)
C21	0.101 (2)	0.080 (2)	0.086 (2)	0.0036 (17)	0.0625 (19)	0.0039 (17)
C22	0.0738 (19)	0.0719 (19)	0.0671 (18)	0.0182 (15)	0.0205 (15)	−0.0081 (14)

S1—C7	1.767 (2)	C13—C14	1.385 (3)
S1—C8	1.819 (2)	C13—C15	1.537 (3)
O1—C1	1.311 (3)	C14—H14	0.9300
O1—H1	0.837 (18)	C15—C16	1.527 (4)
O2—C1	1.215 (3)	C15—C18	1.535 (4)
O3—C12	1.378 (3)	C15—C17	1.541 (4)
O3—H3	0.75 (3)	C16—H16A	0.9600
C1—C2	1.474 (3)	C16—H16B	0.9600
C2—C3	1.396 (3)	C16—H16C	0.9600
C2—C7	1.409 (3)	C17—H17A	0.9600
C3—C4	1.368 (3)	C17—H17B	0.9600
C3—H3A	0.9300	C17—H17C	0.9600
C4—C5	1.377 (4)	C18—H18A	0.9600
C4—H4	0.9300	C18—H18B	0.9600
C5—C6	1.368 (3)	C18—H18C	0.9600
C5—H5	0.9300	C19—C22	1.528 (3)
C6—C7	1.402 (3)	C19—C21	1.529 (4)
C6—H6	0.9300	C19—C20	1.532 (4)
C8—C9	1.500 (3)	C20—H20A	0.9600
C8—H8A	0.9700	C20—H20B	0.9600
C8—H8B	0.9700	C20—H20C	0.9600
C9—C14	1.381 (3)	C21—H21A	0.9600
C9—C10	1.382 (3)	C21—H21B	0.9600
C10—C11	1.386 (3)	C21—H21C	0.9600
C10—H10	0.9300	C22—H22A	0.9600
C11—C12	1.403 (3)	C22—H22B	0.9600
C11—C19	1.546 (3)	C22—H22C	0.9600
C12—C13	1.406 (3)
C7—S1—C8	102.81 (11)	C16—C15—C18	105.9 (3)
C1—O1—H1	113 (2)	C16—C15—C13	112.7 (2)
C12—O3—H3	115 (3)	C18—C15—C13	112.0 (2)
O2—C1—O1	121.9 (2)	C16—C15—C17	107.0 (3)
O2—C1—C2	123.7 (2)	C18—C15—C17	108.2 (2)
O1—C1—C2	114.4 (2)	C13—C15—C17	110.7 (2)
C3—C2—C7	119.6 (2)	C15—C16—H16A	109.5
C3—C2—C1	118.5 (2)	C15—C16—H16B	109.5
C7—C2—C1	121.9 (2)	H16A—C16—H16B	109.5
C4—C3—C2	121.7 (2)	C15—C16—H16C	109.5
C4—C3—H3A	119.2	H16A—C16—H16C	109.5
C2—C3—H3A	119.2	H16B—C16—H16C	109.5
C3—C4—C5	119.0 (2)	C15—C17—H17A	109.5
C3—C4—H4	120.5	C15—C17—H17B	109.5
C5—C4—H4	120.5	H17A—C17—H17B	109.5
C6—C5—C4	120.7 (2)	C15—C17—H17C	109.5
C6—C5—H5	119.7	H17A—C17—H17C	109.5
C4—C5—H5	119.7	H17B—C17—H17C	109.5
C5—C6—C7	121.9 (2)	C15—C18—H18A	109.5
C5—C6—H6	119.1	C15—C18—H18B	109.5
C7—C6—H6	119.1	H18A—C18—H18B	109.5
C6—C7—C2	117.2 (2)	C15—C18—H18C	109.5
C6—C7—S1	121.41 (18)	H18A—C18—H18C	109.5
C2—C7—S1	121.41 (18)	H18B—C18—H18C	109.5
C9—C8—S1	108.23 (17)	C22—C19—C21	110.1 (2)
C9—C8—H8A	110.1	C22—C19—C20	105.9 (2)
S1—C8—H8A	110.1	C21—C19—C20	107.8 (2)
C9—C8—H8B	110.1	C22—C19—C11	111.29 (19)
S1—C8—H8B	110.1	C21—C19—C11	110.3 (2)
H8A—C8—H8B	108.4	C20—C19—C11	111.3 (2)
C14—C9—C10	118.3 (2)	C19—C20—H20A	109.5
C14—C9—C8	120.6 (2)	C19—C20—H20B	109.5
C10—C9—C8	121.1 (2)	H20A—C20—H20B	109.5
C9—C10—C11	123.0 (2)	C19—C20—H20C	109.5
C9—C10—H10	118.5	H20A—C20—H20C	109.5
C11—C10—H10	118.5	H20B—C20—H20C	109.5
C10—C11—C12	116.5 (2)	C19—C21—H21A	109.5
C10—C11—C19	120.7 (2)	C19—C21—H21B	109.5
C12—C11—C19	122.8 (2)	H21A—C21—H21B	109.5
O3—C12—C11	116.68 (19)	C19—C21—H21C	109.5
O3—C12—C13	120.53 (19)	H21A—C21—H21C	109.5
C11—C12—C13	122.8 (2)	H21B—C21—H21C	109.5
C14—C13—C12	116.9 (2)	C19—C22—H22A	109.5
C14—C13—C15	120.2 (2)	C19—C22—H22B	109.5
C12—C13—C15	122.9 (2)	H22A—C22—H22B	109.5
C9—C14—C13	122.5 (2)	C19—C22—H22C	109.5
C9—C14—H14	118.7	H22A—C22—H22C	109.5
C13—C14—H14	118.7	H22B—C22—H22C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.84 (2)	1.83 (2)	2.661 (2)	178 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.84 (2)	1.83 (2)	2.661 (2)	178 (4)

Symmetry code: (i) .