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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2310.
Published online 2008 November 13. doi:  10.1107/S1600536808036246
PMCID: PMC2959805

Redetermination of 1-naphthalene­acetic acid

Abstract

The crystal structure of the title compound, C12H10O2, was originally determined by Rajan [Acta Cryst. (1978). B34, 998–1000] using intensity data estimated from Weissenberg films. This redetermination provides a structure with significantly improved precision with respect to the geometric parameters. In the crystal structure, inter­molecular O—H(...)O hydrogen bonds, weak C—H(...)O hydrogen bonds and C—H(...)π inter­actions link the mol­ecules into a two-dimensional sheet lying parallel to (100).

Related literature

For the original structure determination, see: Rajan (1978 [triangle]). For a description of the Cambridge Structural Database, see: Allen (2002 [triangle]); Bruno et al. (2002 [triangle]).

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Object name is e-64-o2310-scheme1.jpg

Experimental

Crystal data

  • C12H10O2
  • M r = 186.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2310-efi1.jpg
  • a = 12.7079 (19) Å
  • b = 5.1464 (8) Å
  • c = 15.014 (2) Å
  • β = 91.987 (3)°
  • V = 981.3 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 200 (2) K
  • 0.20 × 0.04 × 0.02 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1997 [triangle]) T min = 0.973, T max = 0.993
  • 9953 measured reflections
  • 2025 independent reflections
  • 1416 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.148
  • S = 1.04
  • 2025 reflections
  • 130 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036246/lh2723sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036246/lh2723Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank Dr Gui-Huan Du for helpful discussions about the structure.

supplementary crystallographic information

Comment

A search of the Cambridge Structural Database (CONQUEST Version 1.10, CSD version 5.29, Allen, 2002, Bruno et al., 2002) reveals that the structure of the title compound (I) was first reported (Rajan, 1978) with R = 0.129 for 776 observed reflections. However, the published report did not identify any supramolecular aggregation beyond the formation of a hydrogen-bonded dimers. We have now taken the opportunity to redetermine the structure of the title compound using data collected at 200 K.

In (I), we find the same phase at 200 K as those previously reported at ambient temperature. During the refinement of (I), we have refined the structure without any constraints, and the current precision is significantly better than those reported previously. Thus, for example, the previously reported s.u. values for the C—O bonds are 0.01 (Rajan, 1978); whereas from the present refinement of (I), these s.u. values are only 0.002. In addition, the R value is very much lower for the present refinement (0.0488). The dihedral angles between the naphthalene-ring plane (C1 to C10) and the carboxyl plane (C11/C12/O1/O2) are 80.6 (1)° (Fig.1) for the title compound and 81.3 (1)° for the original detemination, respectively. No unusual molecular features are worthy of discussion.

In compound (I), the molecules are linked by a combination of O—H···O, weak C—H···O hydrogen bonds and C—H···π interaction, into a two-dimensional network. In more detail, the supramolecular aggregation can be analyzed in therms of three aspects. First, the O1 atom in the molecule at (x, y, z), act as the hydrogen-bonding donor, via H1 atom, to the O2 atom in the molecule at (-x, -y, 2 - z), forming a discrete hydrogen-bonding dimer (Fig.2). Secondly, atom C11 at (x, y, z) acts as hydrogen-bond donor (Table 1) to the C1/C6—C10 aryl ring at (x, y - 1,z), forming a C—H···π interaction, which linked the dimers into a one-dimensional chain running parallel to the [010] direction (Fig.2). Finally, these adjacent [010] chains are linked together by a weak C3—H3···O2 hydrogen bond [C···O=3.540 (2) Å, symmetry code: -x, -1/2 + y, 3/2 - z), forming the final two-dimensional sheet lying parallel to the (100) plane (Fig.3). No other direction-specific interactions are observed between the neighbouring sheets.

Experimental

1-Naphthalene-acetic acid (I), was obtained unexpectedly by reaction of mixing 2:1:1 equivalent molar amount of (I), 4,4'-bi-pyridine and Mn(ClO4)2.2(H2O) in 95% methanol (20 ml). The mixture was stirred for 30 minutes at 330 K and then filtered. Colorless needle crystals of (I) suitable for single-crystal X-ray diffraction analysis were grown at the bottom of the vessel in two weeks after slow evaporation of the solution.

Refinement

All H atoms bonded to C atoms were located in difference maps and then treated as ring with C–H = 0.93 Å(aromatic), 0.97 Å (methylene) and refined in a riding mode [Uiso(H) = 1.2Ueq(C)]. H1 atom was found in the difference map and the O—H distance was refined freely [the refined distances are given in Table 1; Uiso(H) = 1.5Ueq(O)].

Figures

Fig. 1.
Molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Part of the crystal structure of (I), showing the formation of the one-dimensional chain structure running parallel to the [010] direction formed by O—H···O and C—H···π interaction ...
Fig. 3.
Part of the crystal structure of (I), showing the formation of the two-dimensional sheet parallel to the (100) plane formed by O—H···O, weak C—H···O hydrogen bonds and C—H···π ...

Crystal data

C12H10O2F000 = 392
Mr = 186.20Dx = 1.260 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2268 reflections
a = 12.7079 (19) Åθ = 2.7–24.9º
b = 5.1464 (8) ŵ = 0.09 mm1
c = 15.014 (2) ÅT = 200 (2) K
β = 91.987 (3)ºNeedle, colorless
V = 981.3 (2) Å30.20 × 0.04 × 0.02 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer2025 independent reflections
Radiation source: fine focus sealed Siemens Mo tube1416 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.023
T = 200(2) Kθmax = 26.5º
0.3° wide ω exposures scansθmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1997)h = −15→15
Tmin = 0.973, Tmax = 0.993k = −6→6
9953 measured reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.148  w = 1/[σ2(Fo2) + (0.0798P)2 + 0.0818P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2025 reflectionsΔρmax = 0.19 e Å3
130 parametersΔρmin = −0.14 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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 (Å2)

xyzUiso*/Ueq
C10.27991 (11)0.1115 (3)0.80540 (10)0.0549 (4)
C20.19500 (12)−0.0420 (3)0.77187 (10)0.0579 (4)
C30.15963 (15)−0.0059 (4)0.68586 (12)0.0769 (5)
H30.1042−0.10730.66360.092*
C40.20412 (19)0.1783 (5)0.63049 (13)0.0905 (6)
H40.17870.19700.57200.109*
C50.28320 (17)0.3281 (4)0.66118 (13)0.0815 (6)
H50.31180.45160.62380.098*
C60.32383 (12)0.3020 (3)0.74899 (12)0.0649 (5)
C70.40692 (17)0.4581 (4)0.78251 (17)0.0924 (7)
H70.43550.58380.74600.111*
C80.44567 (19)0.4292 (6)0.8661 (2)0.1132 (9)
H80.50070.53450.88700.136*
C90.40414 (19)0.2431 (6)0.92165 (16)0.1053 (8)
H90.43190.22440.97940.126*
C100.32338 (15)0.0874 (4)0.89291 (12)0.0775 (5)
H100.2965−0.03610.93120.093*
C110.14486 (15)−0.2410 (3)0.82983 (12)0.0728 (5)
H11A0.0989−0.34940.79270.087*
H11B0.1997−0.35170.85560.087*
C120.08232 (12)−0.1303 (3)0.90375 (11)0.0604 (4)
O10.07037 (12)−0.2832 (3)0.96952 (10)0.0917 (5)
H10.023 (2)−0.225 (5)1.011 (2)0.138*
O20.04415 (11)0.0874 (2)0.90046 (8)0.0860 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0591 (8)0.0544 (9)0.0523 (9)0.0066 (7)0.0167 (7)−0.0096 (7)
C20.0627 (9)0.0566 (9)0.0557 (9)0.0027 (7)0.0183 (7)−0.0095 (7)
C30.0734 (11)0.0958 (14)0.0620 (12)−0.0017 (9)0.0076 (9)−0.0150 (9)
C40.0950 (14)0.1195 (17)0.0576 (11)0.0153 (14)0.0112 (10)0.0128 (11)
C50.0952 (14)0.0817 (13)0.0698 (13)0.0084 (11)0.0328 (11)0.0162 (10)
C60.0638 (9)0.0585 (9)0.0742 (11)0.0034 (7)0.0289 (8)−0.0099 (8)
C70.0866 (13)0.0785 (13)0.1152 (19)−0.0171 (11)0.0461 (13)−0.0290 (12)
C80.0819 (14)0.133 (2)0.126 (2)−0.0281 (14)0.0250 (14)−0.0627 (18)
C90.0887 (14)0.146 (2)0.0808 (15)−0.0005 (15)−0.0074 (12)−0.0414 (15)
C100.0830 (12)0.0901 (13)0.0600 (11)0.0066 (10)0.0102 (9)−0.0117 (10)
C110.0857 (11)0.0573 (10)0.0774 (12)−0.0064 (8)0.0317 (9)−0.0109 (8)
C120.0658 (9)0.0517 (9)0.0649 (10)−0.0026 (7)0.0202 (7)0.0001 (7)
O10.1183 (11)0.0755 (9)0.0845 (9)0.0278 (7)0.0501 (8)0.0218 (7)
O20.1095 (10)0.0677 (8)0.0838 (9)0.0248 (7)0.0461 (7)0.0141 (6)

Geometric parameters (Å, °)

C1—C101.413 (2)C7—H70.9300
C1—C21.416 (2)C8—C91.386 (4)
C1—C61.422 (2)C8—H80.9300
C2—C31.365 (3)C9—C101.360 (3)
C2—C111.500 (2)C9—H90.9300
C3—C41.394 (3)C10—H100.9300
C3—H30.9300C11—C121.500 (2)
C4—C51.336 (3)C11—H11A0.9700
C4—H40.9300C11—H11B0.9700
C5—C61.405 (3)C12—O21.2209 (19)
C5—H50.9300C12—O11.2759 (19)
C6—C71.406 (3)O1—H10.93 (3)
C7—C81.341 (4)
C10—C1—C2123.38 (16)C6—C7—H7119.4
C10—C1—C6117.74 (16)C7—C8—C9120.3 (2)
C2—C1—C6118.88 (15)C7—C8—H8119.8
C3—C2—C1118.83 (15)C9—C8—H8119.8
C3—C2—C11120.60 (16)C10—C9—C8121.0 (2)
C1—C2—C11120.57 (15)C10—C9—H9119.5
C2—C3—C4122.00 (19)C8—C9—H9119.5
C2—C3—H3119.0C9—C10—C1120.6 (2)
C4—C3—H3119.0C9—C10—H10119.7
C5—C4—C3120.17 (19)C1—C10—H10119.7
C5—C4—H4119.9C12—C11—C2114.62 (13)
C3—C4—H4119.9C12—C11—H11A108.6
C4—C5—C6121.07 (17)C2—C11—H11A108.6
C4—C5—H5119.5C12—C11—H11B108.6
C6—C5—H5119.5C2—C11—H11B108.6
C5—C6—C7121.88 (18)H11A—C11—H11B107.6
C5—C6—C1119.03 (16)O2—C12—O1122.64 (14)
C7—C6—C1119.08 (19)O2—C12—C11122.59 (15)
C8—C7—C6121.2 (2)O1—C12—C11114.75 (14)
C8—C7—H7119.4C12—O1—H1114.4 (17)
C10—C1—C2—C3−179.14 (15)C2—C1—C6—C7178.88 (14)
C6—C1—C2—C31.4 (2)C5—C6—C7—C8−179.27 (19)
C10—C1—C2—C110.8 (2)C1—C6—C7—C80.5 (3)
C6—C1—C2—C11−178.64 (12)C6—C7—C8—C90.0 (3)
C1—C2—C3—C4−0.4 (3)C7—C8—C9—C10−0.3 (4)
C11—C2—C3—C4179.63 (16)C8—C9—C10—C10.1 (3)
C2—C3—C4—C5−0.6 (3)C2—C1—C10—C9−179.13 (17)
C3—C4—C5—C60.7 (3)C6—C1—C10—C90.3 (2)
C4—C5—C6—C7−179.91 (18)C3—C2—C11—C12−110.23 (19)
C4—C5—C6—C10.4 (3)C1—C2—C11—C1269.8 (2)
C10—C1—C6—C5179.13 (15)C2—C11—C12—O224.3 (3)
C2—C1—C6—C5−1.4 (2)C2—C11—C12—O1−157.00 (17)
C10—C1—C6—C7−0.6 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.932.613.541 (2)177
O1—H1···O2ii0.93 (3)1.76 (3)2.6723 (17)168 (3)
C11—H11B···Cg1iii0.972.873.746 (2)151

Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) −x, −y, −z+2; (iii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2723).

References

  • Allen, F. H. (2002). Acta Cryst. B58, 380–388. [PubMed]
  • Bruker (2001). SAINT-Plus and SMART Bruker AXS, Inc., Madison, Wisconsin, USA.
  • Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389–397. [PubMed]
  • Rajan, S. S. (1978). Acta Cryst. B34, 998–1000.
  • Sheldrick, G. M. (1997). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography