2,6-Di-tert-butyl-4-(3-chloro-2-hy-droxy-prop-yl)phenol.

In the title 2-propanol derivative, C(17)H(27)ClO(2), 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 hy-droxy O atom belonging to the alkyl substituent of an adjacent mol-ecule, 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 = 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) Å3

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

Δρmax = 0.59 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008592/xu5167sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008592/xu5167Isup2.hkl

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

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

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 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

	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*

	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)

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)

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

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) .