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The molecule of the title compound, C15H24O2, lies across a mirror plane with the two tert-butyl substituents flanking the phenolic OH group in this hindered phenol. In the crystal structure, O—H...O hydrogen bonds between the benzyl OH group and the phenolic O atom link the mol­ecules into chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604791X/lh2244sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680604791X/lh2244Isup2.hkl
Contains datablock I

CCDC reference: 630164

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.064
  • wR factor = 0.201
  • Data-to-parameter ratio = 8.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT076_ALERT_1_C Occupancy 0.50 less than 1.0 for Sp.pos . H1 PLAT076_ALERT_1_C Occupancy 0.50 less than 1.0 for Sp.pos . H1A PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.31 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.92 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT415_ALERT_2_C Short Inter D-H..H-X H2A .. H6B .. 2.10 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H6B .. O2 .. 2.67 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H7B .. O2 .. 2.63 Ang. PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.27 Ratio
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.01 From the CIF: _reflns_number_total 740 Count of symmetry unique reflns 744 Completeness (_total/calc) 99.46% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

2,6-di-tert-butyl-4-(hydroxymethyl)phenol top
Crystal data top
C15H24O2Dx = 1.059 Mg m3
Mr = 236.34Melting point = 412–413 K
Orthorhombic, Pmn21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac -2Cell parameters from 2308 reflections
a = 18.901 (5) Åθ = 3.4–26.1°
b = 6.2580 (14) ŵ = 0.07 mm1
c = 6.2670 (19) ÅT = 294 K
V = 741.3 (3) Å3Block, colourless
Z = 20.32 × 0.28 × 0.24 mm
F(000) = 260
Data collection top
Bruker SMART CCD area-detector
diffractometer
740 independent reflections
Radiation source: fine-focus sealed tube685 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 25.0°, θmin = 3.4°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 2220
Tmin = 0.979, Tmax = 0.984k = 75
3466 measured reflectionsl = 76
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.1499P)2 + 0.1064P]
where P = (Fo2 + 2Fc2)/3
740 reflections(Δ/σ)max = 0.001
92 parametersΔρmax = 0.49 e Å3
2 restraintsΔρmin = 0.21 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.00000.5588 (7)0.5338 (8)0.0712 (13)
H10.00000.55700.66650.085*0.5
H1A0.00000.43310.47870.085*0.5
C10.00000.7185 (6)0.3821 (7)0.0342 (10)
C20.06634 (14)0.7979 (4)0.3063 (6)0.0344 (8)
C30.06387 (15)0.9599 (5)0.1500 (6)0.0400 (8)
H30.10611.01460.09720.048*
C40.00001.0411 (7)0.0715 (8)0.0453 (11)
C50.13906 (14)0.7111 (5)0.3912 (6)0.0425 (9)
C60.1469 (2)0.4730 (6)0.3333 (10)0.0659 (13)
H6A0.14180.45550.18190.099*
H6B0.11100.39180.40520.099*
H6C0.19270.42320.37670.099*
C70.14506 (18)0.7456 (8)0.6423 (9)0.0660 (12)
H7A0.10900.66410.71290.099*
H7B0.13910.89440.67490.099*
H7C0.19080.69920.69030.099*
C80.20304 (17)0.8268 (7)0.2866 (8)0.0599 (11)
H8A0.24620.76090.33310.090*
H8B0.20300.97450.32790.090*
H8C0.19950.81640.13410.090*
C90.00001.2170 (10)0.0980 (11)0.0708 (19)
H9A0.00971.34990.02740.085*0.50
H9B0.04711.22660.15480.085*0.50
O20.0467 (4)1.2023 (17)0.2662 (15)0.125 (4)0.50
H2A0.04031.30640.35100.188*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.077 (3)0.064 (3)0.072 (3)0.0000.0000.044 (2)
C10.040 (2)0.032 (2)0.030 (2)0.0000.0000.0099 (18)
C20.0378 (16)0.0289 (15)0.0366 (17)0.0022 (10)0.0007 (12)0.0006 (14)
C30.0436 (16)0.0348 (16)0.0415 (17)0.0066 (12)0.0053 (15)0.0062 (16)
C40.055 (2)0.037 (2)0.044 (2)0.0000.0000.011 (2)
C50.0323 (16)0.0475 (19)0.0476 (19)0.0056 (11)0.0009 (13)0.0017 (16)
C60.053 (2)0.047 (2)0.097 (4)0.0139 (15)0.003 (2)0.000 (2)
C70.052 (2)0.097 (3)0.049 (2)0.006 (2)0.0137 (19)0.001 (2)
C80.0363 (16)0.070 (2)0.073 (3)0.0003 (16)0.0013 (17)0.007 (2)
C90.066 (3)0.066 (4)0.081 (5)0.0000.0000.046 (4)
O20.141 (6)0.139 (8)0.096 (6)0.051 (6)0.040 (7)0.042 (6)
Geometric parameters (Å, º) top
O1—C11.379 (6)C6—H6B0.9600
O1—H10.8315C6—H6C0.9600
O1—H1A0.8592C7—H7A0.9600
C1—C21.430 (3)C7—H7B0.9600
C1—C2i1.430 (3)C7—H7C0.9600
C2—C31.411 (5)C8—H8A0.9600
C2—C51.570 (4)C8—H8B0.9600
C3—C41.399 (4)C8—H8C0.9600
C3—H30.9300C9—O2i1.378 (7)
C4—C3i1.399 (4)C9—O21.378 (7)
C4—C91.530 (7)C9—H9A0.9595
C5—C61.541 (5)C9—H9B0.9601
C5—C81.554 (5)O2—O2i1.766 (15)
C5—C71.592 (7)O2—H2A0.8498
C6—H6A0.9600
C1—O1—H1134.4H6A—C6—H6C109.5
C1—O1—H1A112.7H6B—C6—H6C109.5
H1—O1—H1A112.9C5—C7—H7A109.5
O1—C1—C2118.72 (17)C5—C7—H7B109.5
O1—C1—C2i118.72 (17)H7A—C7—H7B109.5
C2—C1—C2i122.6 (3)C5—C7—H7C109.5
C3—C2—C1116.8 (3)H7A—C7—H7C109.5
C3—C2—C5120.8 (3)H7B—C7—H7C109.5
C1—C2—C5122.3 (3)C5—C8—H8A109.5
C4—C3—C2122.3 (3)C5—C8—H8B109.5
C4—C3—H3118.9H8A—C8—H8B109.5
C2—C3—H3118.9C5—C8—H8C109.5
C3i—C4—C3119.3 (4)H8A—C8—H8C109.5
C3i—C4—C9120.4 (2)H8B—C8—H8C109.5
C3—C4—C9120.4 (2)O2i—C9—O279.7 (9)
C6—C5—C8106.1 (3)O2i—C9—C4118.9 (6)
C6—C5—C2109.8 (3)O2—C9—C4118.9 (6)
C8—C5—C2112.2 (3)O2i—C9—H9A122.2
C6—C5—C7110.9 (4)O2—C9—H9A106.8
C8—C5—C7107.3 (3)C4—C9—H9A107.7
C2—C5—C7110.5 (3)O2—C9—H9B108.3
C5—C6—H6A109.5C4—C9—H9B107.6
C5—C6—H6B109.5H9A—C9—H9B107.1
H6A—C6—H6B109.5C9—O2—H2A109.6
C5—C6—H6C109.5
O1—C1—C2—C3179.5 (4)C3—C2—C5—C81.1 (5)
C2i—C1—C2—C30.4 (6)C1—C2—C5—C8178.9 (3)
O1—C1—C2—C50.5 (6)C3—C2—C5—C7120.8 (4)
C2i—C1—C2—C5179.6 (2)C1—C2—C5—C759.2 (4)
C1—C2—C3—C40.2 (5)C3i—C4—C9—O2i43.0 (9)
C5—C2—C3—C4179.8 (4)C3—C4—C9—O2i137.1 (6)
C2—C3—C4—C3i0.0 (7)C3i—C4—C9—O2137.1 (6)
C2—C3—C4—C9179.9 (5)C3—C4—C9—O243.0 (9)
C3—C2—C5—C6116.6 (4)C4—C9—O2—O2i117.4 (9)
C1—C2—C5—C663.5 (5)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O1ii0.851.902.707 (10)159
C6—H6B···O2iii0.962.673.571 (10)157
C7—H7B···O2iv0.962.633.457 (11)145
Symmetry codes: (ii) x, y+1, z1; (iii) x, y1, z+1; (iv) x, y, z+1.
 

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