2,6-Di-tert-butyl-4-(hydroxy­meth­yl)phenol

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.

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

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Computing details

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

Crystal data

C15H24O2	Dx = 1.059 Mg m^−3
Mr = 236.34	Melting point = 412–413 K
Orthorhombic, Pmn21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac -2	Cell parameters from 2308 reflections
a = 18.901 (5) Å	θ = 3.4–26.1°
b = 6.2580 (14) Å	µ = 0.07 mm^−1
c = 6.2670 (19) Å	T = 294 K
V = 741.3 (3) Å^3	Block, colourless
Z = 2	0.32 × 0.28 × 0.24 mm
F(000) = 260

Data collection

Bruker SMART CCD area-detector diffractometer	740 independent reflections
Radiation source: fine-focus sealed tube	685 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 25.0°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −22→20
Tmin = 0.979, Tmax = 0.984	k = −7→5
3466 measured reflections	l = −7→6

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.201	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.1499P)^2 + 0.1064P] where P = (Fo^2 + 2Fc^2)/3
740 reflections	(Δ/σ)max = 0.001
92 parameters	Δρmax = 0.49 e Å^−3
2 restraints	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.0000	0.5588 (7)	0.5338 (8)	0.0712 (13)
H1	0.0000	0.5570	0.6665	0.085*	0.5
H1A	0.0000	0.4331	0.4787	0.085*	0.5
C1	0.0000	0.7185 (6)	0.3821 (7)	0.0342 (10)
C2	0.06634 (14)	0.7979 (4)	0.3063 (6)	0.0344 (8)
C3	0.06387 (15)	0.9599 (5)	0.1500 (6)	0.0400 (8)
H3	0.1061	1.0146	0.0972	0.048*
C4	0.0000	1.0411 (7)	0.0715 (8)	0.0453 (11)
C5	0.13906 (14)	0.7111 (5)	0.3912 (6)	0.0425 (9)
C6	0.1469 (2)	0.4730 (6)	0.3333 (10)	0.0659 (13)
H6A	0.1418	0.4555	0.1819	0.099*
H6B	0.1110	0.3918	0.4052	0.099*
H6C	0.1927	0.4232	0.3767	0.099*
C7	0.14506 (18)	0.7456 (8)	0.6423 (9)	0.0660 (12)
H7A	0.1090	0.6641	0.7129	0.099*
H7B	0.1391	0.8944	0.6749	0.099*
H7C	0.1908	0.6992	0.6903	0.099*
C8	0.20304 (17)	0.8268 (7)	0.2866 (8)	0.0599 (11)
H8A	0.2462	0.7609	0.3331	0.090*
H8B	0.2030	0.9745	0.3279	0.090*
H8C	0.1995	0.8164	0.1341	0.090*
C9	0.0000	1.2170 (10)	−0.0980 (11)	0.0708 (19)
H9A	0.0097	1.3499	−0.0274	0.085*	0.50
H9B	−0.0471	1.2266	−0.1548	0.085*	0.50
O2	0.0467 (4)	1.2023 (17)	−0.2662 (15)	0.125 (4)	0.50
H2A	0.0403	1.3064	−0.3510	0.188*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.077 (3)	0.064 (3)	0.072 (3)	0.000	0.000	0.044 (2)
C1	0.040 (2)	0.032 (2)	0.030 (2)	0.000	0.000	0.0099 (18)
C2	0.0378 (16)	0.0289 (15)	0.0366 (17)	0.0022 (10)	−0.0007 (12)	−0.0006 (14)
C3	0.0436 (16)	0.0348 (16)	0.0415 (17)	−0.0066 (12)	0.0053 (15)	0.0062 (16)
C4	0.055 (2)	0.037 (2)	0.044 (2)	0.000	0.000	0.011 (2)
C5	0.0323 (16)	0.0475 (19)	0.0476 (19)	0.0056 (11)	−0.0009 (13)	0.0017 (16)
C6	0.053 (2)	0.047 (2)	0.097 (4)	0.0139 (15)	−0.003 (2)	0.000 (2)
C7	0.052 (2)	0.097 (3)	0.049 (2)	0.006 (2)	−0.0137 (19)	0.001 (2)
C8	0.0363 (16)	0.070 (2)	0.073 (3)	−0.0003 (16)	0.0013 (17)	0.007 (2)
C9	0.066 (3)	0.066 (4)	0.081 (5)	0.000	0.000	0.046 (4)
O2	0.141 (6)	0.139 (8)	0.096 (6)	0.051 (6)	0.040 (7)	0.042 (6)

Geometric parameters (Å, º)

O1—C1	1.379 (6)	C6—H6B	0.9600
O1—H1	0.8315	C6—H6C	0.9600
O1—H1A	0.8592	C7—H7A	0.9600
C1—C2	1.430 (3)	C7—H7B	0.9600
C1—C2^i	1.430 (3)	C7—H7C	0.9600
C2—C3	1.411 (5)	C8—H8A	0.9600
C2—C5	1.570 (4)	C8—H8B	0.9600
C3—C4	1.399 (4)	C8—H8C	0.9600
C3—H3	0.9300	C9—O2^i	1.378 (7)
C4—C3^i	1.399 (4)	C9—O2	1.378 (7)
C4—C9	1.530 (7)	C9—H9A	0.9595
C5—C6	1.541 (5)	C9—H9B	0.9601
C5—C8	1.554 (5)	O2—O2^i	1.766 (15)
C5—C7	1.592 (7)	O2—H2A	0.8498
C6—H6A	0.9600
C1—O1—H1	134.4	H6A—C6—H6C	109.5
C1—O1—H1A	112.7	H6B—C6—H6C	109.5
H1—O1—H1A	112.9	C5—C7—H7A	109.5
O1—C1—C2	118.72 (17)	C5—C7—H7B	109.5
O1—C1—C2^i	118.72 (17)	H7A—C7—H7B	109.5
C2—C1—C2^i	122.6 (3)	C5—C7—H7C	109.5
C3—C2—C1	116.8 (3)	H7A—C7—H7C	109.5
C3—C2—C5	120.8 (3)	H7B—C7—H7C	109.5
C1—C2—C5	122.3 (3)	C5—C8—H8A	109.5
C4—C3—C2	122.3 (3)	C5—C8—H8B	109.5
C4—C3—H3	118.9	H8A—C8—H8B	109.5
C2—C3—H3	118.9	C5—C8—H8C	109.5
C3^i—C4—C3	119.3 (4)	H8A—C8—H8C	109.5
C3^i—C4—C9	120.4 (2)	H8B—C8—H8C	109.5
C3—C4—C9	120.4 (2)	O2^i—C9—O2	79.7 (9)
C6—C5—C8	106.1 (3)	O2^i—C9—C4	118.9 (6)
C6—C5—C2	109.8 (3)	O2—C9—C4	118.9 (6)
C8—C5—C2	112.2 (3)	O2^i—C9—H9A	122.2
C6—C5—C7	110.9 (4)	O2—C9—H9A	106.8
C8—C5—C7	107.3 (3)	C4—C9—H9A	107.7
C2—C5—C7	110.5 (3)	O2—C9—H9B	108.3
C5—C6—H6A	109.5	C4—C9—H9B	107.6
C5—C6—H6B	109.5	H9A—C9—H9B	107.1
H6A—C6—H6B	109.5	C9—O2—H2A	109.6
C5—C6—H6C	109.5
O1—C1—C2—C3	179.5 (4)	C3—C2—C5—C8	1.1 (5)
C2^i—C1—C2—C3	−0.4 (6)	C1—C2—C5—C8	−178.9 (3)
O1—C1—C2—C5	−0.5 (6)	C3—C2—C5—C7	120.8 (4)
C2^i—C1—C2—C5	179.6 (2)	C1—C2—C5—C7	−59.2 (4)
C1—C2—C3—C4	0.2 (5)	C3^i—C4—C9—O2^i	−43.0 (9)
C5—C2—C3—C4	−179.8 (4)	C3—C4—C9—O2^i	137.1 (6)
C2—C3—C4—C3^i	0.0 (7)	C3^i—C4—C9—O2	−137.1 (6)
C2—C3—C4—C9	179.9 (5)	C3—C4—C9—O2	43.0 (9)
C3—C2—C5—C6	−116.6 (4)	C4—C9—O2—O2^i	117.4 (9)
C1—C2—C5—C6	63.5 (5)

Symmetry code: (i) −x, y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1^ii	0.85	1.90	2.707 (10)	159
C6—H6B···O2^iii	0.96	2.67	3.571 (10)	157
C7—H7B···O2^iv	0.96	2.63	3.457 (11)	145

Symmetry codes: (ii) x, y+1, z−1; (iii) x, y−1, z+1; (iv) x, y, z+1.