Redetermination of 1-acenaphthenol

The crystal structure determination of the title compound, C₁₂H₁₀O, has been reported previously [Gupta & Gupta (1975). Acta Cryst. B31, 7–9], with an R value of 0.078. The results reported here are in agreement with the literature data but a more precise mol­ecular geometry is obtained (σ on C—C = 0.002 Å). Inter­molecular O—H...O hydrogen bonds connect mol­ecules into a chain running parallel to the [010] direction. This chain is reinforced by two C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 290 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.100
• Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C7     -   C8      ..       6.81 su

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

   0 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and DIAMOND (Crystal Impact, 2001); software used to prepare material for publication: SHELXL97.

1-acenaphthenol

Crystal data

C12H10O	F(000) = 360
Mr = 170.20	Dx = 1.295 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4587 reflections
a = 12.9585 (11) Å	θ = 4.2–25.0°
b = 4.9326 (5) Å	µ = 0.08 mm^−1
c = 15.6749 (19) Å	T = 290 K
β = 119.398 (9)°	Plate, translucent white
V = 872.91 (16) Å^3	0.49 × 0.28 × 0.09 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur3 CCD diffractometer	1501 independent reflections
Radiation source: fine-focus sealed tube	1267 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
ω scans	θmax = 25.0°, θmin = 4.2°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2005)	h = −15→14
Tmin = 0.968, Tmax = 0.991	k = −5→2
4587 measured reflections	l = −18→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0542P)^2 + 0.1377P] where P = (Fo^2 + 2Fc^2)/3
1501 reflections	(Δ/σ)max = 0.002
130 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.13 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
O1	0.05537 (9)	0.7036 (2)	0.26686 (8)	0.0458 (3)
C1	0.24939 (11)	0.9417 (2)	0.19722 (10)	0.0364 (3)
C2	0.23950 (11)	0.8436 (3)	0.27663 (9)	0.0369 (3)
C3	0.31334 (13)	0.9457 (3)	0.36760 (11)	0.0477 (4)
H3	0.3091	0.8845	0.4219	0.057*
C4	0.39686 (12)	1.1477 (3)	0.37760 (12)	0.0536 (4)
H4	0.4468	1.2185	0.4395	0.064*
C5	0.40664 (13)	1.2417 (3)	0.30015 (13)	0.0554 (4)
H5	0.4628	1.3733	0.3099	0.066*
C6	0.33102 (12)	1.1391 (3)	0.20415 (12)	0.0452 (4)
C7	0.32811 (15)	1.2141 (3)	0.11561 (14)	0.0602 (5)
H7	0.3802	1.3446	0.1160	0.072*
C8	0.24848 (17)	1.0938 (4)	0.02979 (14)	0.0630 (5)
H8	0.2480	1.1448	−0.0275	0.076*
C9	0.16691 (15)	0.8957 (3)	0.02410 (11)	0.0536 (4)
H9	0.1140	0.8184	−0.0358	0.064*
C10	0.16669 (12)	0.8192 (3)	0.10747 (10)	0.0405 (3)
C11	0.09385 (13)	0.6190 (3)	0.12812 (10)	0.0432 (4)
C12	0.14355 (11)	0.6304 (3)	0.24107 (10)	0.0368 (3)
H12A	0.1759 (14)	0.451 (3)	0.2702 (12)	0.055*
H11A	0.1008 (14)	0.432 (3)	0.1063 (12)	0.055*
H11B	0.0064 (15)	0.666 (3)	0.0963 (12)	0.055*
H1A	0.0164 (16)	0.566 (4)	0.2570 (12)	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0483 (6)	0.0379 (5)	0.0658 (7)	−0.0024 (4)	0.0393 (5)	−0.0036 (5)
C1	0.0346 (6)	0.0296 (6)	0.0496 (8)	0.0059 (5)	0.0243 (6)	0.0038 (6)
C2	0.0356 (7)	0.0326 (7)	0.0429 (7)	0.0066 (5)	0.0197 (6)	0.0025 (5)
C3	0.0457 (8)	0.0464 (8)	0.0448 (8)	0.0060 (6)	0.0175 (6)	−0.0018 (6)
C4	0.0380 (8)	0.0510 (9)	0.0543 (9)	−0.0002 (6)	0.0092 (7)	−0.0112 (7)
C5	0.0369 (8)	0.0451 (8)	0.0802 (12)	−0.0035 (6)	0.0256 (8)	−0.0040 (8)
C6	0.0393 (7)	0.0369 (7)	0.0667 (9)	0.0046 (6)	0.0316 (7)	0.0049 (7)
C7	0.0629 (10)	0.0483 (9)	0.0910 (13)	0.0014 (8)	0.0545 (10)	0.0139 (9)
C8	0.0819 (12)	0.0590 (10)	0.0669 (11)	0.0048 (9)	0.0511 (10)	0.0114 (9)
C9	0.0684 (10)	0.0533 (9)	0.0449 (8)	0.0035 (8)	0.0325 (8)	0.0028 (7)
C10	0.0447 (8)	0.0371 (7)	0.0432 (7)	0.0065 (6)	0.0242 (6)	0.0023 (6)
C11	0.0441 (8)	0.0398 (7)	0.0442 (8)	−0.0034 (6)	0.0205 (6)	−0.0040 (6)
C12	0.0393 (7)	0.0293 (7)	0.0480 (8)	0.0045 (5)	0.0262 (6)	0.0044 (6)

Geometric parameters (Å, º)

O1—C12	1.4328 (15)	C6—C7	1.419 (2)
O1—H1A	0.813 (18)	C7—C8	1.365 (3)
C1—C2	1.3989 (19)	C7—H7	0.9300
C1—C6	1.4020 (19)	C8—C9	1.410 (2)
C1—C10	1.4187 (19)	C8—H8	0.9300
C2—C3	1.365 (2)	C9—C10	1.362 (2)
C2—C12	1.5107 (18)	C9—H9	0.9300
C3—C4	1.422 (2)	C10—C11	1.5070 (19)
C3—H3	0.9300	C11—C12	1.560 (2)
C4—C5	1.362 (2)	C11—H11A	1.002 (17)
C4—H4	0.9300	C11—H11B	1.017 (16)
C5—C6	1.426 (2)	C12—H12A	0.988 (17)
C5—H5	0.9300
C12—O1—H1A	104.0 (12)	C7—C8—C9	122.98 (15)
C2—C1—C6	124.51 (13)	C7—C8—H8	118.5
C2—C1—C10	112.36 (12)	C9—C8—H8	118.5
C6—C1—C10	123.13 (13)	C10—C9—C8	119.09 (15)
C3—C2—C1	118.59 (13)	C10—C9—H9	120.5
C3—C2—C12	132.09 (13)	C8—C9—H9	120.5
C1—C2—C12	109.32 (11)	C9—C10—C1	118.50 (13)
C2—C3—C4	118.62 (14)	C9—C10—C11	133.19 (14)
C2—C3—H3	120.7	C1—C10—C11	108.30 (12)
C4—C3—H3	120.7	C10—C11—C12	105.48 (11)
C5—C4—C3	122.61 (14)	C10—C11—H11A	111.0 (9)
C5—C4—H4	118.7	C12—C11—H11A	111.4 (9)
C3—C4—H4	118.7	C10—C11—H11B	114.2 (9)
C4—C5—C6	120.21 (14)	C12—C11—H11B	106.7 (9)
C4—C5—H5	119.9	H11A—C11—H11B	108.1 (13)
C6—C5—H5	119.9	O1—C12—C2	110.26 (10)
C1—C6—C7	116.65 (14)	O1—C12—C11	112.78 (11)
C1—C6—C5	115.46 (14)	C2—C12—C11	104.50 (10)
C7—C6—C5	127.89 (14)	O1—C12—H12A	108.1 (9)
C8—C7—C6	119.65 (15)	C2—C12—H12A	111.5 (10)
C8—C7—H7	120.2	C11—C12—H12A	109.8 (9)
C6—C7—H7	120.2
C6—C1—C2—C3	0.31 (19)	C6—C7—C8—C9	0.3 (3)
C10—C1—C2—C3	−179.54 (11)	C7—C8—C9—C10	0.0 (3)
C6—C1—C2—C12	−179.06 (11)	C8—C9—C10—C1	−0.3 (2)
C10—C1—C2—C12	1.09 (14)	C8—C9—C10—C11	179.99 (15)
C1—C2—C3—C4	0.15 (19)	C2—C1—C10—C9	−179.79 (12)
C12—C2—C3—C4	179.35 (13)	C6—C1—C10—C9	0.4 (2)
C2—C3—C4—C5	−0.5 (2)	C2—C1—C10—C11	−0.01 (15)
C3—C4—C5—C6	0.4 (2)	C6—C1—C10—C11	−179.86 (12)
C2—C1—C6—C7	−179.93 (12)	C9—C10—C11—C12	178.72 (15)
C10—C1—C6—C7	−0.09 (19)	C1—C10—C11—C12	−1.02 (14)
C2—C1—C6—C5	−0.41 (19)	C3—C2—C12—O1	57.64 (19)
C10—C1—C6—C5	179.42 (12)	C1—C2—C12—O1	−123.10 (11)
C4—C5—C6—C1	0.0 (2)	C3—C2—C12—C11	179.09 (14)
C4—C5—C6—C7	179.50 (14)	C1—C2—C12—C11	−1.65 (13)
C1—C6—C7—C8	−0.2 (2)	C10—C11—C12—O1	121.36 (12)
C5—C6—C7—C8	−179.67 (15)	C10—C11—C12—C2	1.59 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O1^i	0.82 (2)	1.97 (2)	2.771 (1)	170 (2)
C11—H11A···Cg3^ii	1.00 (2)	2.77 (2)	3.653 (2)	147 (1)
C12—H12A···Cg2^ii	0.99 (2)	2.69 (2)	3.558 (2)	146 (2)

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