2,6-Di-tert-butyl-4-(3-chloro-2-hy­droxy­prop­yl)phenol

Abstract

In the title 2-propanol derivative, C₁₇H₂₇ClO₂, the two tert-butyl groups both have one methyl C atom lying in the plane of the aromatic ring. In the crystal, the phenol group forms a hydrogen bond to the hy­droxy O atom belonging to the alkyl substituent of an adjacent mol­ecule, forming a chain along the ac diagonal. The Cl atom is disordered over two positions in a 0.73 (4):0.27 (4) ratio.

Related literature

For the synthesis: see: Krysin et al. (2010 ▶).

Experimental

Crystal data

• C₁₇H₂₇ClO₂

• M _r = 298.84

• Monoclinic,

• a = 5.9536 (3) Å

• b = 19.4819 (9) Å

• c = 14.4310 (7) Å

• β = 96.798 (1)°

• V = 1662.05 (14) ų

• Z = 4

• Mo Kα radiation

• μ = 0.23 mm⁻¹

• T = 100 K

• 0.30 × 0.30 × 0.30 mm

Data collection

• Bruker APEXII diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.934, T _max = 0.934

• 17600 measured reflections

• 3819 independent reflections

• 3374 reflections with I > 2σ(I)

• R _int = 0.035

Refinement

• R[F ² > 2σ(F ²)] = 0.049

• wR(F ²) = 0.131

• S = 1.12

• 3819 reflections

• 193 parameters

• 1 restraint

• H-atom parameters constrained

• Δρ_max = 0.59 e Å⁻³

• Δρ_min = −0.36 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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, 2010 ▶).

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.84	2.31	2.956 (2)	134

Symmetry code: (i) .

supplementary crystallographic information

Comment

The chlorohydrin unit (i.e., an alkyl chain having a chlorine atom and a hydroxy group on adjacent carbons) is an important unit in compounds used for the treatment of protozoal and bacterial infections; and chlorohydrin-based compounds are important intermediates in the synthesis of some HIV protease inhibitors. The di-tert-butyl phenol unit is also an important component of medicinal compounds. The two units are assembled in the title compound (Scheme I).

The compound can be further transformed; in fact, replacing the chlorine atom by a diisopropylamino group furnishes a 2:1 co-crystal with succinic acid that has been patented for its antiarrhythmic and antihypertensive activities (Krysin et al., 2010).

The two tert-butyl groups of C₁₇H₂₇ClO₂ both have one methyl C lying in the plane of the aromatic ring (Fig. 1). The phenolic group forms a hydrogen bond to the hydroxy O atom belonging to the alkyl substituent of an adjacent molecule to form a chain along the a–c diagonal of the monoclinic unit cell (Fig. 2).

Experimental

The compound was prepared by using a procedure reported in the patent literature (Krysin et al., 2010), and colorless crystals was obtained upon recrystallization from ethanol.

Refinement

Carbon-bound H-atoms were placed in calculated positions [C–H 0.93 to 0.97 Å; U(H) 1.2 to 1.5U(C)] and were included in the refinement in the riding model approximation. The hydroxy H-atoms were similarly treated (O–H 0.84 Å) and their temperature factors tied by a factor of 1.5.

The chlorine atom is disordered over two positions; the C–Cl pair of distances were restrained to within Å of each other. The disordered refined to a 73 (4): 27 ratio. The thermal ellipsoid of the minor component is somewhat elongated; however, no restraints were imposed to render it to be less elongated.

Figures

Fig. 1.

Thermal ellipsoid plot (Barbour, 2001) of C17H27ClO2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the chlorine atom is not shown.

Fig. 2.

Hydrogen-bonded chain motif.

Crystal data

C17H27ClO2	F(000) = 648
Mr = 298.84	Dx = 1.194 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6280 reflections
a = 5.9536 (3) Å	θ = 2.5–28.3°
b = 19.4819 (9) Å	µ = 0.23 mm−1
c = 14.4310 (7) Å	T = 100 K
β = 96.798 (1)°	Prism, colorless
V = 1662.05 (14) Å3	0.30 × 0.30 × 0.30 mm
Z = 4

Data collection

Bruker APEXII diffractometer	3819 independent reflections
Radiation source: fine-focus sealed tube	3374 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.934, Tmax = 0.934	k = −25→25
17600 measured reflections	l = −18→18

Refinement

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.057P)2 + 1.2061P] where P = (Fo2 + 2Fc2)/3
3819 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.59 e Å−3
1 restraint	Δρmin = −0.36 e Å−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	1.2917 (5)	0.47575 (14)	0.5791 (3)	0.0266 (6)	0.73 (4)
Cl1'	1.311 (2)	0.4728 (6)	0.5926 (16)	0.048 (2)	0.27 (4)
O1	1.1454 (2)	0.31683 (6)	0.56395 (9)	0.0212 (3)
H1	1.2420	0.3195	0.5261	0.032*
O2	0.3696 (2)	0.18279 (6)	0.25797 (9)	0.0199 (3)
H2	0.3138	0.2071	0.2130	0.030*
C1	1.0528 (3)	0.43104 (10)	0.61378 (14)	0.0235 (4)
H1A	1.0903	0.4130	0.6779	0.028*	0.73 (4)
H1B	0.9240	0.4631	0.6139	0.028*	0.73 (4)
H1'A	1.0701	0.4134	0.6786	0.028*	0.27 (4)
H1'B	0.9292	0.4653	0.6082	0.028*	0.27 (4)
C2	0.9867 (3)	0.37230 (9)	0.54759 (13)	0.0202 (4)
H2A	0.9834	0.3886	0.4817	0.024*
C3	0.7524 (3)	0.34483 (9)	0.56317 (12)	0.0190 (4)
H3A	0.7664	0.3169	0.6209	0.023*
H3B	0.6514	0.3840	0.5721	0.023*
C4	0.6473 (3)	0.30175 (9)	0.48281 (12)	0.0159 (3)
C5	0.5064 (3)	0.33223 (9)	0.41043 (12)	0.0159 (3)
H5	0.4776	0.3801	0.4134	0.019*
C6	0.4059 (3)	0.29514 (8)	0.33367 (11)	0.0144 (3)
C7	0.4559 (3)	0.22451 (9)	0.33061 (11)	0.0146 (3)
C8	0.5969 (3)	0.19141 (8)	0.40264 (11)	0.0145 (3)
C9	0.6889 (3)	0.23165 (9)	0.47749 (12)	0.0155 (3)
H9	0.7837	0.2104	0.5268	0.019*
C10	0.2464 (3)	0.33124 (9)	0.25678 (12)	0.0169 (3)
C11	0.2100 (3)	0.40719 (9)	0.27950 (14)	0.0244 (4)
H11A	0.3558	0.4311	0.2862	0.037*
H11B	0.1420	0.4107	0.3379	0.037*
H11C	0.1089	0.4282	0.2289	0.037*
C12	0.3501 (3)	0.33046 (10)	0.16400 (13)	0.0225 (4)
H12A	0.4996	0.3522	0.1729	0.034*
H12B	0.2516	0.3558	0.1166	0.034*
H12C	0.3653	0.2829	0.1434	0.034*
C13	0.0101 (3)	0.29757 (10)	0.24768 (13)	0.0211 (4)
H13A	−0.0494	0.2991	0.3081	0.032*
H13B	0.0218	0.2497	0.2279	0.032*
H13C	−0.0922	0.3226	0.2013	0.032*
C14	0.6512 (3)	0.11431 (8)	0.39914 (12)	0.0158 (3)
C15	0.8079 (3)	0.09121 (9)	0.48583 (13)	0.0215 (4)
H15A	0.9483	0.1179	0.4907	0.032*
H15B	0.8430	0.0423	0.4803	0.032*
H15C	0.7324	0.0986	0.5417	0.032*
C16	0.4356 (3)	0.07064 (9)	0.39586 (14)	0.0234 (4)
H16A	0.3307	0.0835	0.3411	0.035*
H16B	0.3637	0.0785	0.4526	0.035*
H16C	0.4749	0.0220	0.3917	0.035*
C17	0.7752 (3)	0.09881 (9)	0.31401 (13)	0.0216 (4)
H17A	0.6804	0.1128	0.2570	0.032*
H17B	0.8062	0.0495	0.3114	0.032*
H17C	0.9182	0.1242	0.3193	0.032*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Cl1	0.0251 (8)	0.0174 (9)	0.0380 (11)	−0.0002 (7)	0.0068 (6)	0.0062 (11)
Cl1'	0.022 (2)	0.042 (4)	0.078 (5)	−0.016 (2)	0.001 (3)	−0.034 (3)
O1	0.0165 (6)	0.0191 (6)	0.0277 (7)	0.0035 (5)	0.0020 (5)	−0.0010 (5)
O2	0.0264 (7)	0.0159 (6)	0.0154 (6)	0.0009 (5)	−0.0061 (5)	−0.0014 (5)
C1	0.0196 (9)	0.0227 (9)	0.0280 (10)	−0.0023 (7)	0.0022 (7)	−0.0025 (7)
C2	0.0180 (8)	0.0182 (8)	0.0238 (9)	0.0019 (7)	−0.0002 (7)	−0.0011 (7)
C3	0.0171 (8)	0.0202 (8)	0.0186 (8)	0.0021 (7)	−0.0020 (6)	−0.0044 (7)
C4	0.0122 (7)	0.0189 (8)	0.0167 (8)	−0.0006 (6)	0.0022 (6)	−0.0027 (6)
C5	0.0154 (8)	0.0137 (7)	0.0189 (8)	0.0005 (6)	0.0029 (6)	−0.0001 (6)
C6	0.0128 (7)	0.0158 (8)	0.0145 (8)	0.0002 (6)	0.0017 (6)	0.0022 (6)
C7	0.0139 (7)	0.0165 (8)	0.0133 (8)	−0.0011 (6)	0.0015 (6)	−0.0016 (6)
C8	0.0132 (7)	0.0146 (8)	0.0160 (8)	0.0012 (6)	0.0030 (6)	0.0009 (6)
C9	0.0132 (7)	0.0189 (8)	0.0141 (8)	0.0013 (6)	0.0008 (6)	0.0012 (6)
C10	0.0157 (8)	0.0163 (8)	0.0180 (8)	0.0003 (6)	−0.0011 (6)	0.0022 (6)
C11	0.0277 (10)	0.0159 (8)	0.0276 (10)	0.0041 (7)	−0.0051 (8)	0.0024 (7)
C12	0.0237 (9)	0.0257 (9)	0.0176 (9)	−0.0010 (7)	0.0007 (7)	0.0059 (7)
C13	0.0142 (8)	0.0238 (9)	0.0242 (9)	0.0003 (7)	−0.0018 (7)	0.0020 (7)
C14	0.0171 (8)	0.0138 (8)	0.0162 (8)	0.0014 (6)	0.0006 (6)	0.0013 (6)
C15	0.0228 (9)	0.0182 (8)	0.0222 (9)	0.0051 (7)	−0.0023 (7)	0.0027 (7)
C16	0.0205 (9)	0.0191 (9)	0.0298 (10)	−0.0025 (7)	0.0001 (7)	0.0053 (7)
C17	0.0256 (9)	0.0173 (8)	0.0226 (9)	0.0044 (7)	0.0058 (7)	−0.0006 (7)

Geometric parameters (Å, °)

Cl1—C1	1.788 (3)	C9—H9	0.9500
Cl1'—C1	1.795 (6)	C10—C11	1.537 (2)
O1—C2	1.437 (2)	C10—C12	1.539 (3)
O1—H1	0.8400	C10—C13	1.544 (2)
O2—C7	1.377 (2)	C11—H11A	0.9800
O2—H2	0.8400	C11—H11B	0.9800
C1—C2	1.513 (3)	C11—H11C	0.9800
C1—H1A	0.9900	C12—H12A	0.9800
C1—H1B	0.9900	C12—H12B	0.9800
C1—H1'A	0.9900	C12—H12C	0.9800
C1—H1'B	0.9900	C13—H13A	0.9800
C2—C3	1.535 (2)	C13—H13B	0.9800
C2—H2A	1.0000	C13—H13C	0.9800
C3—C4	1.506 (2)	C14—C17	1.536 (2)
C3—H3A	0.9900	C14—C16	1.536 (2)
C3—H3B	0.9900	C14—C15	1.537 (2)
C4—C9	1.392 (2)	C15—H15A	0.9800
C4—C5	1.393 (2)	C15—H15B	0.9800
C5—C6	1.396 (2)	C15—H15C	0.9800
C5—H5	0.9500	C16—H16A	0.9800
C6—C7	1.410 (2)	C16—H16B	0.9800
C6—C10	1.542 (2)	C16—H16C	0.9800
C7—C8	1.412 (2)	C17—H17A	0.9800
C8—C9	1.393 (2)	C17—H17B	0.9800
C8—C14	1.539 (2)	C17—H17C	0.9800
C2—O1—H1	109.5	C11—C10—C6	112.10 (14)
C7—O2—H2	109.5	C12—C10—C6	110.19 (14)
C2—C1—Cl1	110.38 (18)	C11—C10—C13	106.08 (14)
C2—C1—Cl1'	113.5 (5)	C12—C10—C13	112.16 (15)
C2—C1—H1A	109.6	C6—C10—C13	110.17 (14)
Cl1—C1—H1A	109.6	C10—C11—H11A	109.5
Cl1'—C1—H1A	102.5	C10—C11—H11B	109.5
C2—C1—H1B	109.6	H11A—C11—H11B	109.5
Cl1—C1—H1B	109.6	C10—C11—H11C	109.5
Cl1'—C1—H1B	113.1	H11A—C11—H11C	109.5
H1A—C1—H1B	108.1	H11B—C11—H11C	109.5
C2—C1—H1'A	108.9	C10—C12—H12A	109.5
Cl1—C1—H1'A	115.9	C10—C12—H12B	109.5
Cl1'—C1—H1'A	108.9	H12A—C12—H12B	109.5
C2—C1—H1'B	108.9	C10—C12—H12C	109.5
Cl1'—C1—H1'B	108.9	H12A—C12—H12C	109.5
H1'A—C1—H1'B	107.7	H12B—C12—H12C	109.5
O1—C2—C1	110.37 (15)	C10—C13—H13A	109.5
O1—C2—C3	107.78 (14)	C10—C13—H13B	109.5
C1—C2—C3	110.14 (15)	H13A—C13—H13B	109.5
O1—C2—H2A	109.5	C10—C13—H13C	109.5
C1—C2—H2A	109.5	H13A—C13—H13C	109.5
C3—C2—H2A	109.5	H13B—C13—H13C	109.5
C4—C3—C2	112.54 (14)	C17—C14—C16	110.21 (15)
C4—C3—H3A	109.1	C17—C14—C8	109.93 (13)
C2—C3—H3A	109.1	C16—C14—C8	111.33 (14)
C4—C3—H3B	109.1	C17—C14—C15	106.87 (14)
C2—C3—H3B	109.1	C16—C14—C15	106.72 (14)
H3A—C3—H3B	107.8	C8—C14—C15	111.65 (14)
C9—C4—C5	118.18 (15)	C14—C15—H15A	109.5
C9—C4—C3	121.94 (15)	C14—C15—H15B	109.5
C5—C4—C3	119.88 (15)	H15A—C15—H15B	109.5
C6—C5—C4	122.53 (15)	C14—C15—H15C	109.5
C6—C5—H5	118.7	H15A—C15—H15C	109.5
C4—C5—H5	118.7	H15B—C15—H15C	109.5
C5—C6—C7	117.23 (15)	C14—C16—H16A	109.5
C5—C6—C10	120.29 (15)	C14—C16—H16B	109.5
C7—C6—C10	122.48 (15)	H16A—C16—H16B	109.5
O2—C7—C6	122.59 (15)	C14—C16—H16C	109.5
O2—C7—C8	115.26 (14)	H16A—C16—H16C	109.5
C6—C7—C8	122.14 (15)	H16B—C16—H16C	109.5
C9—C8—C7	117.30 (15)	C14—C17—H17A	109.5
C9—C8—C14	120.65 (14)	C14—C17—H17B	109.5
C7—C8—C14	122.04 (15)	H17A—C17—H17B	109.5
C4—C9—C8	122.60 (15)	C14—C17—H17C	109.5
C4—C9—H9	118.7	H17A—C17—H17C	109.5
C8—C9—H9	118.7	H17B—C17—H17C	109.5
C11—C10—C12	106.04 (15)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.84	2.31	2.956 (2)	134

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