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The molecule of the title compound, C
12H
10O
2, is planar, with an intramolecular O—H
O hydrogen bond between the hydroxy group and the carbonyl O atom. The structure is stabilized by intermolecular C—H
π and offset π–π stacking interactions.
Supporting information
CCDC reference: 601160
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.060
- wR factor = 0.171
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.72 mm
PLAT074_ALERT_1_C Occupancy Parameter = 0.0 for .................. CG1
PLAT074_ALERT_1_C Occupancy Parameter = 0.0 for .................. CG2
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
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
1-(1-Hydroxy-2-naphthyl)ethanone
top
Crystal data top
C12H10O2 | F(000) = 392 |
Mr = 186.20 | Dx = 1.321 Mg m−3 |
Monoclinic, P21/c | Melting point: 372 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.6259 (10) Å | Cell parameters from 10250 reflections |
b = 7.0348 (7) Å | θ = 2.3–27.1° |
c = 18.755 (3) Å | µ = 0.09 mm−1 |
β = 111.502 (10)° | T = 296 K |
V = 936.1 (2) Å3 | Prismatic stick, pale yellow |
Z = 4 | 0.72 × 0.34 × 0.14 mm |
Data collection top
Stoe IPDS-2 diffractometer | 1692 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1015 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.100 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.3°, θmin = 2.3° |
ω scan rotation method | h = −9→9 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −8→8 |
Tmin = 0.548, Tmax = 0.946 | l = −22→22 |
10250 measured reflections | |
Refinement top
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0964P)2] where P = (Fo2 + 2Fc2)/3 |
1692 reflections | (Δ/σ)max < 0.001 |
129 parameters | Δρmax = 0.11 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 1.0794 (4) | 0.2215 (5) | 0.66670 (16) | 0.1110 (11) | |
H1A | 1.1682 | 0.1914 | 0.6430 | 0.166* | |
H1B | 0.9827 | 0.1262 | 0.6536 | 0.166* | |
H1C | 1.1430 | 0.2254 | 0.7213 | 0.166* | |
C2 | 0.9926 (4) | 0.4108 (5) | 0.63892 (14) | 0.0862 (8) | |
C3 | 0.8637 (3) | 0.4367 (3) | 0.55939 (12) | 0.0698 (6) | |
C4 | 0.8234 (3) | 0.2867 (3) | 0.50551 (13) | 0.0738 (7) | |
H4 | 0.8807 | 0.1692 | 0.5209 | 0.089* | |
C5 | 0.7040 (3) | 0.3096 (3) | 0.43245 (13) | 0.0742 (7) | |
H5 | 0.6818 | 0.2086 | 0.3982 | 0.089* | |
C6 | 0.6120 (3) | 0.4859 (3) | 0.40719 (12) | 0.0656 (6) | |
C7 | 0.4825 (3) | 0.5147 (4) | 0.33177 (13) | 0.0818 (8) | |
H7 | 0.4567 | 0.4152 | 0.2968 | 0.098* | |
C8 | 0.3950 (4) | 0.6839 (5) | 0.30924 (15) | 0.0916 (8) | |
H8 | 0.3091 | 0.6988 | 0.2594 | 0.110* | |
C9 | 0.4328 (4) | 0.8346 (5) | 0.35991 (19) | 0.0940 (9) | |
H9 | 0.3725 | 0.9505 | 0.3439 | 0.113* | |
C10 | 0.5580 (4) | 0.8144 (4) | 0.43324 (16) | 0.0826 (7) | |
H10 | 0.5835 | 0.9173 | 0.4667 | 0.099* | |
C11 | 0.6491 (3) | 0.6394 (3) | 0.45884 (12) | 0.0667 (6) | |
C12 | 0.7788 (3) | 0.6115 (3) | 0.53556 (13) | 0.0701 (6) | |
O1 | 1.0298 (3) | 0.5474 (4) | 0.68427 (10) | 0.1133 (8) | |
O2 | 0.8105 (3) | 0.7617 (3) | 0.58252 (10) | 0.0964 (6) | |
H2 | 0.8881 | 0.7332 | 0.6247 | 0.145* | |
CG1 | 0.7385 | 0.4616 | 0.4832 | 0.010* | 0.00 |
CG2 | 0.5216 | 0.6622 | 0.3834 | 0.010* | 0.00 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0816 (18) | 0.159 (3) | 0.0863 (18) | 0.0089 (19) | 0.0239 (14) | 0.042 (2) |
C2 | 0.0681 (15) | 0.129 (2) | 0.0652 (15) | −0.0139 (15) | 0.0291 (13) | 0.0039 (16) |
C3 | 0.0700 (14) | 0.0809 (16) | 0.0619 (13) | −0.0104 (12) | 0.0281 (11) | 0.0002 (11) |
C4 | 0.0790 (15) | 0.0688 (14) | 0.0749 (15) | −0.0012 (11) | 0.0298 (13) | 0.0032 (11) |
C5 | 0.0864 (16) | 0.0660 (14) | 0.0728 (14) | −0.0072 (12) | 0.0322 (13) | −0.0105 (12) |
C6 | 0.0676 (14) | 0.0705 (14) | 0.0621 (13) | −0.0062 (11) | 0.0279 (11) | −0.0006 (10) |
C7 | 0.0787 (17) | 0.0988 (19) | 0.0683 (15) | −0.0092 (14) | 0.0273 (13) | −0.0011 (13) |
C8 | 0.0753 (17) | 0.116 (2) | 0.0814 (17) | 0.0006 (16) | 0.0266 (14) | 0.0249 (17) |
C9 | 0.0812 (17) | 0.093 (2) | 0.114 (2) | 0.0124 (14) | 0.0430 (17) | 0.0283 (17) |
C10 | 0.0855 (17) | 0.0684 (15) | 0.1061 (19) | −0.0025 (13) | 0.0495 (16) | −0.0013 (14) |
C11 | 0.0695 (14) | 0.0662 (14) | 0.0734 (14) | −0.0078 (11) | 0.0368 (12) | −0.0027 (11) |
C12 | 0.0753 (15) | 0.0734 (15) | 0.0695 (14) | −0.0160 (12) | 0.0358 (12) | −0.0170 (12) |
O1 | 0.0957 (14) | 0.169 (2) | 0.0707 (11) | −0.0252 (14) | 0.0258 (10) | −0.0246 (13) |
O2 | 0.1047 (14) | 0.0965 (13) | 0.0905 (12) | −0.0169 (10) | 0.0388 (10) | −0.0369 (10) |
Geometric parameters (Å, º) top
C1—C2 | 1.493 (4) | C6—C7 | 1.412 (3) |
C1—H1A | 0.9600 | C7—C8 | 1.355 (4) |
C1—H1B | 0.9600 | C7—H7 | 0.9300 |
C1—H1C | 0.9600 | C8—C9 | 1.382 (4) |
C2—O1 | 1.245 (3) | C8—H8 | 0.9300 |
C2—C3 | 1.466 (3) | C9—C10 | 1.364 (4) |
C3—C12 | 1.385 (3) | C9—H9 | 0.9300 |
C3—C4 | 1.415 (3) | C10—C11 | 1.409 (3) |
C4—C5 | 1.348 (3) | C10—H10 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.430 (3) |
C5—C6 | 1.418 (3) | C12—O2 | 1.340 (3) |
C5—H5 | 0.9300 | O2—H2 | 0.8200 |
C6—C11 | 1.409 (3) | | |
| | | |
C2—C1—H1A | 109.5 | C7—C6—C5 | 122.6 (2) |
C2—C1—H1B | 109.5 | C8—C7—C6 | 121.5 (3) |
H1A—C1—H1B | 109.5 | C8—C7—H7 | 119.3 |
C2—C1—H1C | 109.5 | C6—C7—H7 | 119.3 |
H1A—C1—H1C | 109.5 | C7—C8—C9 | 120.3 (3) |
H1B—C1—H1C | 109.5 | C7—C8—H8 | 119.8 |
O1—C2—C3 | 119.9 (3) | C9—C8—H8 | 119.8 |
O1—C2—C1 | 119.3 (2) | C10—C9—C8 | 120.4 (3) |
C3—C2—C1 | 120.8 (3) | C10—C9—H9 | 119.8 |
C12—C3—C4 | 118.6 (2) | C8—C9—H9 | 119.8 |
C12—C3—C2 | 119.9 (2) | C9—C10—C11 | 120.7 (3) |
C4—C3—C2 | 121.5 (2) | C9—C10—H10 | 119.7 |
C5—C4—C3 | 121.7 (2) | C11—C10—H10 | 119.7 |
C5—C4—H4 | 119.1 | C10—C11—C6 | 119.1 (2) |
C3—C4—H4 | 119.1 | C10—C11—C12 | 122.4 (2) |
C4—C5—C6 | 120.7 (2) | C6—C11—C12 | 118.5 (2) |
C4—C5—H5 | 119.6 | O2—C12—C3 | 122.5 (2) |
C6—C5—H5 | 119.6 | O2—C12—C11 | 116.4 (2) |
C11—C6—C7 | 118.0 (2) | C3—C12—C11 | 121.1 (2) |
C11—C6—C5 | 119.4 (2) | C12—O2—H2 | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···Cg2i | 0.96 | 2.79 | 3.593 (3) | 142 |
O2—H2···O1 | 0.82 | 1.80 | 2.524 (3) | 146 |
Symmetry code: (i) −x+2, −y+1, −z+1. |
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