1-(2-Hydroxy­phen­yl)octan-1-one

The title compound, C₁₄H₂₀O₂, was synthesized by the reaction of phenol and octa­noyl chloride. All non-H atoms are coplanar, with an r.m.s. deviation of 0.031 Å. In the crystal structure, mol­ecules are linked into chains along the a axis by inter­molecular C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 288 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.060
• wR factor = 0.170
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         48 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C8     -   C9      ..       5.43 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

1-(2-hydroxyphenyl)octanone

Crystal data

C14H20O2	Z = 2
Mr = 220.30	F(000) = 240
Triclinic, P1	Dx = 1.124 Mg m^−3
Hall symbol: -P 1	Melting point: 294 K K
a = 6.8560 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4850 (17) Å	Cell parameters from 25 reflections
c = 11.547 (2) Å	θ = 10–13°
α = 95.20 (3)°	µ = 0.07 mm^−1
β = 102.54 (3)°	T = 288 K
γ = 93.15 (3)°	Block, light yellow
V = 651.1 (2) Å^3	0.40 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	1229 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 26.0°, θmin = 1.8°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
Tmin = 0.971, Tmax = 0.986	l = −14→13
2781 measured reflections	3 standard reflections every 200 reflections
2555 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.170	w = 1/[σ^2(Fo^2) + (0.07P)^2 + 0.02P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2555 reflections	Δρmax = 0.14 e Å^−3
146 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (6)

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
O1	0.2599 (2)	1.1164 (2)	0.79697 (16)	0.0762 (6)
O2	0.4406 (2)	0.9798 (2)	0.65026 (16)	0.0860 (7)
H2A	0.4278	1.0419	0.7063	0.129*
C1	−0.5829 (5)	1.4578 (4)	1.2579 (3)	0.0980 (11)
H1A	−0.5637	1.5403	1.3228	0.147*
H1B	−0.6134	1.3578	1.2853	0.147*
H1C	−0.6917	1.4799	1.1952	0.147*
C2	−0.3931 (4)	1.4505 (3)	1.2111 (2)	0.0716 (8)
H2B	−0.3609	1.5531	1.1862	0.086*
H2C	−0.2836	1.4298	1.2753	0.086*
C3	−0.4086 (4)	1.3258 (3)	1.1082 (2)	0.0610 (7)
H3A	−0.5194	1.3457	1.0445	0.073*
H3B	−0.4392	1.2231	1.1335	0.073*
C4	−0.2205 (4)	1.3190 (3)	1.0597 (2)	0.0608 (7)
H4A	−0.1896	1.4217	1.0345	0.073*
H4B	−0.1097	1.2986	1.1232	0.073*
C5	−0.2382 (4)	1.1932 (3)	0.9558 (2)	0.0598 (7)
H5A	−0.3498	1.2136	0.8928	0.072*
H5B	−0.2692	1.0908	0.9814	0.072*
C6	−0.0522 (4)	1.1842 (3)	0.9051 (2)	0.0585 (7)
H6A	−0.0211	1.2858	0.8783	0.070*
H6B	0.0601	1.1632	0.9675	0.070*
C7	−0.0786 (3)	1.0561 (3)	0.8020 (2)	0.0542 (7)
H7A	−0.1171	0.9561	0.8285	0.065*
H7B	−0.1882	1.0802	0.7390	0.065*
C8	0.1032 (3)	1.0353 (3)	0.7505 (2)	0.0518 (6)
C9	0.0935 (3)	0.9179 (3)	0.6472 (2)	0.0464 (6)
C10	−0.0825 (4)	0.8275 (3)	0.5918 (2)	0.0550 (7)
H10A	−0.1980	0.8414	0.6203	0.066*
C11	−0.0892 (4)	0.7179 (3)	0.4954 (2)	0.0670 (8)
H11A	−0.2081	0.6581	0.4590	0.080*
C12	0.0832 (4)	0.6972 (3)	0.4529 (2)	0.0685 (8)
H12A	0.0803	0.6224	0.3884	0.082*
C13	0.2568 (4)	0.7863 (3)	0.5056 (2)	0.0682 (8)
H13A	0.3712	0.7729	0.4760	0.082*
C14	0.2643 (4)	0.8959 (3)	0.6022 (2)	0.0569 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0440 (11)	0.0953 (15)	0.0809 (13)	−0.0105 (10)	0.0136 (9)	−0.0248 (11)
O2	0.0407 (11)	0.1209 (17)	0.0946 (15)	−0.0048 (11)	0.0255 (10)	−0.0173 (12)
C1	0.090 (2)	0.114 (3)	0.101 (2)	0.020 (2)	0.051 (2)	−0.009 (2)
C2	0.0758 (19)	0.0687 (19)	0.0745 (18)	0.0101 (15)	0.0317 (15)	−0.0087 (15)
C3	0.0563 (16)	0.0619 (17)	0.0656 (16)	0.0073 (13)	0.0193 (13)	−0.0037 (13)
C4	0.0537 (16)	0.0654 (17)	0.0627 (16)	0.0074 (13)	0.0173 (13)	−0.0089 (13)
C5	0.0503 (15)	0.0659 (17)	0.0626 (17)	0.0052 (13)	0.0158 (13)	−0.0053 (13)
C6	0.0507 (15)	0.0644 (17)	0.0593 (15)	0.0077 (13)	0.0146 (12)	−0.0070 (13)
C7	0.0449 (14)	0.0622 (17)	0.0551 (15)	0.0039 (12)	0.0144 (12)	−0.0028 (12)
C8	0.0397 (14)	0.0585 (16)	0.0567 (15)	0.0053 (12)	0.0094 (12)	0.0059 (13)
C9	0.0405 (13)	0.0513 (15)	0.0489 (14)	0.0047 (11)	0.0141 (11)	0.0025 (11)
C10	0.0489 (15)	0.0561 (16)	0.0620 (16)	0.0013 (12)	0.0202 (12)	−0.0007 (13)
C11	0.0633 (18)	0.0629 (18)	0.0717 (18)	−0.0049 (14)	0.0176 (15)	−0.0091 (14)
C12	0.084 (2)	0.0586 (18)	0.0676 (18)	0.0177 (16)	0.0283 (16)	−0.0019 (14)
C13	0.0614 (19)	0.079 (2)	0.0718 (19)	0.0223 (16)	0.0283 (15)	0.0075 (16)
C14	0.0430 (15)	0.0684 (18)	0.0615 (16)	0.0067 (13)	0.0171 (13)	0.0042 (14)

Geometric parameters (Å, º)

O1—C8	1.232 (3)	C5—H5B	0.97
O2—C14	1.348 (3)	C6—C7	1.510 (3)
O2—H2A	0.82	C6—H6A	0.97
C1—C2	1.516 (3)	C6—H6B	0.97
C1—H1A	0.96	C7—C8	1.505 (3)
C1—H1B	0.96	C7—H7A	0.97
C1—H1C	0.96	C7—H7B	0.97
C2—C3	1.499 (3)	C8—C9	1.470 (3)
C2—H2B	0.97	C9—C10	1.388 (3)
C2—H2C	0.97	C9—C14	1.395 (3)
C3—C4	1.516 (3)	C10—C11	1.375 (3)
C3—H3A	0.97	C10—H10A	0.93
C3—H3B	0.97	C11—C12	1.388 (3)
C4—C5	1.511 (3)	C11—H11A	0.93
C4—H4A	0.97	C12—C13	1.365 (4)
C4—H4B	0.97	C12—H12A	0.93
C5—C6	1.517 (3)	C13—C14	1.376 (3)
C5—H5A	0.97	C13—H13A	0.93
C14—O2—H2A	109.5	C7—C6—H6A	109.2
C2—C1—H1A	109.5	C5—C6—H6A	109.2
C2—C1—H1B	109.5	C7—C6—H6B	109.2
H1A—C1—H1B	109.5	C5—C6—H6B	109.2
C2—C1—H1C	109.5	H6A—C6—H6B	107.9
H1A—C1—H1C	109.5	C8—C7—C6	115.2 (2)
H1B—C1—H1C	109.5	C8—C7—H7A	108.5
C3—C2—C1	113.6 (2)	C6—C7—H7A	108.5
C3—C2—H2B	108.9	C8—C7—H7B	108.5
C1—C2—H2B	108.9	C6—C7—H7B	108.5
C3—C2—H2C	108.9	H7A—C7—H7B	107.5
C1—C2—H2C	108.9	O1—C8—C9	120.8 (2)
H2B—C2—H2C	107.7	O1—C8—C7	119.0 (2)
C2—C3—C4	114.0 (2)	C9—C8—C7	120.1 (2)
C2—C3—H3A	108.8	C10—C9—C14	118.4 (2)
C4—C3—H3A	108.8	C10—C9—C8	121.8 (2)
C2—C3—H3B	108.8	C14—C9—C8	119.8 (2)
C4—C3—H3B	108.8	C11—C10—C9	121.2 (2)
H3A—C3—H3B	107.7	C11—C10—H10A	119.4
C5—C4—C3	113.5 (2)	C9—C10—H10A	119.4
C5—C4—H4A	108.9	C10—C11—C12	119.4 (3)
C3—C4—H4A	108.9	C10—C11—H11A	120.3
C5—C4—H4B	108.9	C12—C11—H11A	120.3
C3—C4—H4B	108.9	C13—C12—C11	120.2 (3)
H4A—C4—H4B	107.7	C13—C12—H12A	119.9
C4—C5—C6	114.6 (2)	C11—C12—H12A	119.9
C4—C5—H5A	108.6	C12—C13—C14	120.6 (3)
C6—C5—H5A	108.6	C12—C13—H13A	119.7
C4—C5—H5B	108.6	C14—C13—H13A	119.7
C6—C5—H5B	108.6	O2—C14—C13	117.7 (2)
H5A—C5—H5B	107.6	O2—C14—C9	122.1 (2)
C7—C6—C5	112.2 (2)	C13—C14—C9	120.2 (2)
C1—C2—C3—C4	179.2 (2)	C14—C9—C10—C11	0.5 (4)
C2—C3—C4—C5	−179.8 (2)	C8—C9—C10—C11	−179.9 (2)
C3—C4—C5—C6	179.8 (2)	C9—C10—C11—C12	0.0 (4)
C4—C5—C6—C7	179.8 (2)	C10—C11—C12—C13	−0.8 (4)
C5—C6—C7—C8	−177.4 (2)	C11—C12—C13—C14	0.9 (4)
C6—C7—C8—O1	2.9 (3)	C12—C13—C14—O2	179.9 (2)
C6—C7—C8—C9	−178.0 (2)	C12—C13—C14—C9	−0.3 (4)
O1—C8—C9—C10	−178.6 (2)	C10—C9—C14—O2	179.4 (2)
C7—C8—C9—C10	2.3 (3)	C8—C9—C14—O2	−0.2 (4)
O1—C8—C9—C14	1.0 (4)	C10—C9—C14—C13	−0.4 (4)
C7—C8—C9—C14	−178.1 (2)	C8—C9—C14—C13	180.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	1.82	2.542 (2)	146
C7—H7B···O2^i	0.97	2.59	3.377 (3)	138

Symmetry code: (i) x−1, y, z.