2-(3,5-Di-tert-butyl-4-hydroxy-benzyl-sulfan-yl)nicotinic acid.

Two mol-ecules of the title compound, C(21)H(27)NO(3)S, are disposed about a center of inversion, generating an O-H⋯O hydrogen-bonded dimer.

Related literature

For the applications of hindered phenol-based anti­oxidants, see: Kim & Lee (2003 ▶); Um & Lee (2005 ▶).

Experimental

Crystal data

C21H27NO3S

M = 373.50

Triclinic,

a = 5.6305 (1) Å

b = 9.3489 (2) Å

c = 18.8749 (3) Å

α = 85.505 (1)°

β = 89.453 (1)°

γ = 87.834 (1)°

V = 989.77 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 100 (2) K

0.25 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.956, T max = 0.991

12688 measured reflections

4507 independent reflections

3746 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.127

S = 1.18

4507 reflections

239 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.75 e Å−3

Δρmin = −0.71 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: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026056/tk2295sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026056/tk2295Isup2.hkl

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

C21H27NO3S	Z = 2
Mr = 373.50	F000 = 400
Triclinic, P1	Dx = 1.253 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.6305 (1) Å	Cell parameters from 3920 reflections
b = 9.3489 (2) Å	θ = 2.2–28.4º
c = 18.8749 (3) Å	µ = 0.18 mm−1
α = 85.505 (1)º	T = 100 (2) K
β = 89.453 (1)º	Prism, colorless
γ = 87.834 (1)º	0.25 × 0.15 × 0.05 mm
V = 989.77 (3) Å3

Bruker SMART APEX diffractometer	4507 independent reflections
Radiation source: fine-focus sealed tube	3746 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
T = 100(2) K	θmax = 27.5º
ω scans	θmin = 1.1º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.956, Tmax = 0.991	k = −9→12
12688 measured reflections	l = −24→24

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0642P)2 + 0.2102P] where P = (Fo2 + 2Fc2)/3
S = 1.18	(Δ/σ)max = 0.001
4507 reflections	Δρmax = 0.75 e Å−3
239 parameters	Δρmin = −0.71 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
S1	0.58009 (7)	0.68988 (5)	0.60316 (2)	0.01722 (13)
O1	0.0857 (2)	0.63037 (14)	0.42620 (6)	0.0211 (3)
H1O	−0.014 (4)	0.566 (2)	0.4379 (14)	0.053 (8)*
O2	0.2215 (2)	0.56848 (14)	0.53598 (6)	0.0222 (3)
O3	0.8816 (2)	0.54828 (13)	0.92906 (6)	0.0161 (3)
H3O	0.7848	0.4934	0.9503	0.024*
N1	0.7549 (3)	0.87163 (16)	0.50351 (7)	0.0177 (3)
C1	0.2358 (3)	0.64038 (19)	0.47879 (9)	0.0184 (4)
C2	0.4212 (3)	0.74553 (19)	0.46400 (8)	0.0176 (4)
C3	0.4393 (3)	0.8192 (2)	0.39715 (9)	0.0203 (4)
H3	0.3316	0.8015	0.3607	0.024*
C4	0.6135 (3)	0.9179 (2)	0.38393 (9)	0.0214 (4)
H4	0.6284	0.9689	0.3386	0.026*
C5	0.7661 (3)	0.9404 (2)	0.43878 (9)	0.0203 (4)
H5	0.8856	1.0087	0.4299	0.024*
C6	0.5857 (3)	0.77544 (19)	0.51655 (8)	0.0165 (3)
C7	0.8320 (3)	0.7718 (2)	0.64204 (8)	0.0171 (3)
H7A	0.9800	0.7489	0.6159	0.021*
H7B	0.8070	0.8775	0.6397	0.021*
C8	0.8498 (3)	0.71171 (19)	0.71821 (8)	0.0149 (3)
C9	0.9743 (3)	0.58333 (19)	0.73576 (8)	0.0152 (3)
H9	1.0514	0.5350	0.6990	0.018*
C10	0.9903 (3)	0.52279 (18)	0.80543 (8)	0.0131 (3)
C11	0.8749 (3)	0.59945 (18)	0.85839 (8)	0.0126 (3)
C12	0.7483 (3)	0.73030 (18)	0.84288 (8)	0.0126 (3)
C13	0.7379 (3)	0.78302 (18)	0.77173 (8)	0.0148 (3)
H13	0.6514	0.8706	0.7595	0.018*
C14	1.1234 (3)	0.37706 (18)	0.82171 (8)	0.0151 (3)
C15	1.3288 (3)	0.38746 (19)	0.87432 (9)	0.0184 (4)
H15A	1.4089	0.2930	0.8832	0.028*
H15B	1.2653	0.4196	0.9192	0.028*
H15C	1.4426	0.4564	0.8541	0.028*
C16	0.9495 (3)	0.2627 (2)	0.85004 (10)	0.0213 (4)
H16A	0.8223	0.2563	0.8155	0.032*
H16B	0.8807	0.2896	0.8952	0.032*
H16C	1.0347	0.1695	0.8575	0.032*
C17	1.2390 (3)	0.3219 (2)	0.75437 (9)	0.0233 (4)
H17A	1.1158	0.3097	0.7193	0.035*
H17B	1.3224	0.2295	0.7665	0.035*
H17C	1.3525	0.3914	0.7345	0.035*
C18	0.6287 (3)	0.81640 (18)	0.90074 (8)	0.0141 (3)
C19	0.8187 (3)	0.8637 (2)	0.95129 (9)	0.0188 (4)
H19A	0.9064	0.7789	0.9727	0.028*
H19B	0.7415	0.9159	0.9888	0.028*
H19C	0.9291	0.9265	0.9245	0.028*
C20	0.4410 (3)	0.72805 (19)	0.94254 (8)	0.0164 (3)
H20A	0.3226	0.6979	0.9096	0.025*
H20B	0.3625	0.7869	0.9773	0.025*
H20C	0.5184	0.6431	0.9674	0.025*
C21	0.4985 (3)	0.95322 (19)	0.86854 (9)	0.0197 (4)
H21A	0.3753	0.9272	0.8361	0.029*
H21B	0.6123	1.0145	0.8423	0.029*
H21C	0.4250	1.0053	0.9067	0.029*

	U11	U22	U33	U12	U13	U23
S1	0.0224 (2)	0.0166 (2)	0.0123 (2)	−0.00013 (16)	−0.00189 (15)	0.00089 (15)
O1	0.0269 (7)	0.0187 (7)	0.0178 (6)	−0.0001 (5)	−0.0059 (5)	−0.0022 (5)
O2	0.0291 (7)	0.0214 (7)	0.0161 (6)	−0.0030 (5)	−0.0045 (5)	−0.0001 (5)
O3	0.0184 (6)	0.0173 (6)	0.0118 (5)	0.0002 (5)	0.0019 (4)	0.0032 (5)
N1	0.0214 (7)	0.0164 (8)	0.0147 (6)	0.0038 (6)	0.0009 (5)	0.0005 (6)
C1	0.0240 (8)	0.0151 (9)	0.0164 (8)	0.0056 (7)	−0.0031 (6)	−0.0053 (7)
C2	0.0233 (8)	0.0145 (9)	0.0149 (8)	0.0050 (7)	−0.0009 (6)	−0.0034 (6)
C3	0.0278 (9)	0.0192 (10)	0.0135 (8)	0.0066 (7)	−0.0025 (6)	−0.0030 (7)
C4	0.0301 (9)	0.0202 (10)	0.0131 (7)	0.0047 (7)	0.0015 (7)	0.0012 (7)
C5	0.0236 (9)	0.0190 (9)	0.0176 (8)	0.0021 (7)	0.0029 (7)	0.0012 (7)
C6	0.0217 (8)	0.0140 (9)	0.0134 (7)	0.0051 (7)	0.0010 (6)	−0.0015 (6)
C7	0.0193 (8)	0.0175 (9)	0.0143 (7)	0.0010 (7)	−0.0013 (6)	0.0004 (6)
C8	0.0156 (7)	0.0154 (9)	0.0135 (7)	−0.0001 (6)	−0.0003 (6)	−0.0001 (6)
C9	0.0154 (7)	0.0163 (9)	0.0143 (7)	0.0008 (6)	0.0003 (6)	−0.0035 (6)
C10	0.0129 (7)	0.0115 (8)	0.0153 (7)	−0.0007 (6)	−0.0012 (6)	−0.0017 (6)
C11	0.0123 (7)	0.0132 (8)	0.0122 (7)	−0.0018 (6)	−0.0013 (5)	0.0000 (6)
C12	0.0121 (7)	0.0125 (8)	0.0135 (7)	−0.0013 (6)	−0.0003 (5)	−0.0020 (6)
C13	0.0152 (7)	0.0126 (8)	0.0162 (8)	0.0014 (6)	−0.0009 (6)	0.0004 (6)
C14	0.0154 (7)	0.0125 (8)	0.0172 (8)	0.0013 (6)	−0.0008 (6)	−0.0016 (6)
C15	0.0145 (8)	0.0162 (9)	0.0242 (9)	0.0035 (7)	−0.0031 (6)	−0.0011 (7)
C16	0.0190 (8)	0.0137 (9)	0.0312 (9)	−0.0008 (7)	−0.0021 (7)	0.0000 (7)
C17	0.0285 (9)	0.0186 (10)	0.0224 (9)	0.0108 (8)	−0.0003 (7)	−0.0045 (7)
C18	0.0155 (7)	0.0120 (8)	0.0147 (7)	0.0009 (6)	0.0011 (6)	−0.0014 (6)
C19	0.0186 (8)	0.0194 (9)	0.0191 (8)	−0.0016 (7)	0.0014 (6)	−0.0061 (7)
C20	0.0141 (7)	0.0173 (9)	0.0180 (8)	−0.0001 (6)	0.0020 (6)	−0.0027 (7)
C21	0.0238 (9)	0.0144 (9)	0.0202 (8)	0.0068 (7)	0.0032 (7)	−0.0017 (7)

S1—C6	1.7634 (16)	C12—C13	1.395 (2)
S1—C7	1.8239 (17)	C12—C18	1.542 (2)
O1—C1	1.321 (2)	C13—H13	0.9500
O1—H1O	0.850 (10)	C14—C17	1.538 (2)
O2—C1	1.230 (2)	C14—C16	1.538 (2)
O3—C11	1.3817 (18)	C14—C15	1.542 (2)
O3—H3O	0.8400	C15—H15A	0.9800
N1—C5	1.337 (2)	C15—H15B	0.9800
N1—C6	1.342 (2)	C15—H15C	0.9800
C1—C2	1.471 (3)	C16—H16A	0.9800
C2—C3	1.394 (2)	C16—H16B	0.9800
C2—C6	1.415 (2)	C16—H16C	0.9800
C3—C4	1.380 (3)	C17—H17A	0.9800
C3—H3	0.9500	C17—H17B	0.9800
C4—C5	1.385 (2)	C17—H17C	0.9800
C4—H4	0.9500	C18—C21	1.536 (2)
C5—H5	0.9500	C18—C19	1.540 (2)
C7—C8	1.505 (2)	C18—C20	1.539 (2)
C7—H7A	0.9900	C19—H19A	0.9800
C7—H7B	0.9900	C19—H19B	0.9800
C8—C9	1.386 (2)	C19—H19C	0.9800
C8—C13	1.387 (2)	C20—H20A	0.9800
C9—C10	1.393 (2)	C20—H20B	0.9800
C9—H9	0.9500	C20—H20C	0.9800
C10—C11	1.414 (2)	C21—H21A	0.9800
C10—C14	1.541 (2)	C21—H21B	0.9800
C11—C12	1.405 (2)	C21—H21C	0.9800
C6—S1—C7	100.24 (8)	C17—C14—C10	111.47 (13)
C1—O1—H1O	109.8 (18)	C16—C14—C10	110.37 (13)
C11—O3—H3O	126.6	C17—C14—C15	105.58 (13)
C5—N1—C6	118.43 (15)	C16—C14—C15	110.68 (14)
O2—C1—O1	122.91 (17)	C10—C14—C15	111.98 (14)
O2—C1—C2	122.32 (15)	C14—C15—H15A	109.5
O1—C1—C2	114.77 (15)	C14—C15—H15B	109.5
C3—C2—C6	117.92 (17)	H15A—C15—H15B	109.5
C3—C2—C1	120.55 (15)	C14—C15—H15C	109.5
C6—C2—C1	121.54 (15)	H15A—C15—H15C	109.5
C4—C3—C2	120.04 (16)	H15B—C15—H15C	109.5
C4—C3—H3	120.0	C14—C16—H16A	109.5
C2—C3—H3	120.0	C14—C16—H16B	109.5
C3—C4—C5	117.91 (16)	H16A—C16—H16B	109.5
C3—C4—H4	121.0	C14—C16—H16C	109.5
C5—C4—H4	121.0	H16A—C16—H16C	109.5
N1—C5—C4	123.84 (17)	H16B—C16—H16C	109.5
N1—C5—H5	118.1	C14—C17—H17A	109.5
C4—C5—H5	118.1	C14—C17—H17B	109.5
N1—C6—C2	121.87 (15)	H17A—C17—H17B	109.5
N1—C6—S1	115.97 (12)	C14—C17—H17C	109.5
C2—C6—S1	122.16 (14)	H17A—C17—H17C	109.5
C8—C7—S1	107.24 (11)	H17B—C17—H17C	109.5
C8—C7—H7A	110.3	C21—C18—C19	107.13 (14)
S1—C7—H7A	110.3	C21—C18—C20	106.49 (13)
C8—C7—H7B	110.3	C19—C18—C20	110.50 (13)
S1—C7—H7B	110.3	C21—C18—C12	111.61 (13)
H7A—C7—H7B	108.5	C19—C18—C12	109.74 (13)
C9—C8—C13	119.07 (14)	C20—C18—C12	111.26 (14)
C9—C8—C7	120.60 (15)	C18—C19—H19A	109.5
C13—C8—C7	120.31 (15)	C18—C19—H19B	109.5
C8—C9—C10	122.24 (15)	H19A—C19—H19B	109.5
C8—C9—H9	118.9	C18—C19—H19C	109.5
C10—C9—H9	118.9	H19A—C19—H19C	109.5
C9—C10—C11	116.84 (15)	H19B—C19—H19C	109.5
C9—C10—C14	120.15 (14)	C18—C20—H20A	109.5
C11—C10—C14	122.99 (14)	C18—C20—H20B	109.5
O3—C11—C12	116.25 (13)	H20A—C20—H20B	109.5
O3—C11—C10	121.08 (14)	C18—C20—H20C	109.5
C12—C11—C10	122.67 (14)	H20A—C20—H20C	109.5
C13—C12—C11	117.06 (14)	H20B—C20—H20C	109.5
C13—C12—C18	120.13 (14)	C18—C21—H21A	109.5
C11—C12—C18	122.80 (14)	C18—C21—H21B	109.5
C8—C13—C12	122.10 (15)	H21A—C21—H21B	109.5
C8—C13—H13	118.9	C18—C21—H21C	109.5
C12—C13—H13	118.9	H21A—C21—H21C	109.5
C17—C14—C16	106.52 (15)	H21B—C21—H21C	109.5
O2—C1—C2—C3	176.46 (16)	C9—C10—C11—O3	−179.75 (14)
O1—C1—C2—C3	−4.1 (2)	C14—C10—C11—O3	1.8 (2)
O2—C1—C2—C6	−3.6 (3)	C9—C10—C11—C12	0.3 (2)
O1—C1—C2—C6	175.85 (15)	C14—C10—C11—C12	−178.16 (15)
C6—C2—C3—C4	−0.1 (2)	O3—C11—C12—C13	−179.46 (13)
C1—C2—C3—C4	179.83 (16)	C10—C11—C12—C13	0.5 (2)
C2—C3—C4—C5	−0.1 (3)	O3—C11—C12—C18	1.9 (2)
C6—N1—C5—C4	−0.3 (3)	C10—C11—C12—C18	−178.11 (14)
C3—C4—C5—N1	0.3 (3)	C9—C8—C13—C12	0.6 (2)
C5—N1—C6—C2	0.0 (2)	C7—C8—C13—C12	179.43 (15)
C5—N1—C6—S1	−179.54 (12)	C11—C12—C13—C8	−1.0 (2)
C3—C2—C6—N1	0.2 (3)	C18—C12—C13—C8	177.73 (15)
C1—C2—C6—N1	−179.77 (15)	C9—C10—C14—C17	3.8 (2)
C3—C2—C6—S1	179.70 (12)	C11—C10—C14—C17	−177.85 (15)
C1—C2—C6—S1	−0.2 (2)	C9—C10—C14—C16	−114.38 (17)
C7—S1—C6—N1	−1.21 (15)	C11—C10—C14—C16	64.0 (2)
C7—S1—C6—C2	179.23 (14)	C9—C10—C14—C15	121.83 (16)
C6—S1—C7—C8	178.80 (11)	C11—C10—C14—C15	−59.8 (2)
S1—C7—C8—C9	85.94 (17)	C13—C12—C18—C21	2.6 (2)
S1—C7—C8—C13	−92.91 (16)	C11—C12—C18—C21	−178.80 (15)
C13—C8—C9—C10	0.3 (2)	C13—C12—C18—C19	−116.01 (16)
C7—C8—C9—C10	−178.57 (15)	C11—C12—C18—C19	62.6 (2)
C8—C9—C10—C11	−0.7 (2)	C13—C12—C18—C20	121.40 (16)
C8—C9—C10—C14	177.77 (15)	C11—C12—C18—C20	−60.00 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2i	0.85 (1)	1.79 (1)	2.640 (2)	179 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2i	0.85 (1)	1.79 (1)	2.640 (2)	179 (3)

Symmetry code: (i) .