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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 12| December 2008| Page o2310
doi:10.1107/S1600536808036246

Redetermination of 1-naphthalene­acetic acid

Zhi-An Li,a,b* Dao-Yong Chenb and Li-Jian Liub

aKey Laboratory of Oral Biomedical Engineering, Ministry of Education, School & Hospital of Stomatology, Wuhan University, Wuhan 430079, People's Republic of China, and bCollege of Chemistry and Molecular Science, Wuhan University, Wuhan 430072, People's Republic of China
*Correspondence e-mail: lizhian2001@126.com

(Received 28 October 2008; accepted 6 November 2008; online 13 November 2008)

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[Rajan, S. S. (1978). Acta Cryst. B34, 998-1000.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]); Bruno et al. (2002[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.]).

[Scheme 1]

Experimental

Crystal data

  • C12H10O2

  • Mr = 186.20

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1997). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.993

  • 9953 measured reflections

  • 2025 independent reflections

  • 1416 reflections with I > 2σ(I)

  • Rint = 0.023
Refinement

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C3—H3⋯O2i 0.93 2.61 3.541 (2) 177
O1—H1⋯O2ii 0.93 (3) 1.76 (3) 2.6723 (17) 168 (3)
C11—H11B⋯Cg1iii 0.97 2.87 3.746 (2) 151
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x, -y, -z+2; (iii) x, y-1, z. Cg1 is the centroid of ring C1/C6–C10.

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT-Plus and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: PLATON.

Supporting information

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

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

checkCIF report


Comment top

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.

Related literature top

For the original structure determination, see: Rajan (1978). Cg1 is the centroid of ring C1/C6–C10. For a description of the Cambridge Structural Database, see: Allen (2002); Bruno et al. (2002).

Experimental top

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 top

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)].

Computing details top

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

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] 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 shown as dashed lines. For the sake of clarity, H atoms not involved in the motif have been omitted from the drawing.
[Figure 3] 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 interaction shown as dashed lines.
1-naphthaleneacetic acid top
Crystal data top
C12H10O2F(000) = 392
Mr = 186.20Dx = 1.260 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2268 reflections
a = 12.7079 (19) Åθ = 2.7–24.9°
b = 5.1464 (8) ŵ = 0.09 mm−1
c = 15.014 (2) ÅT = 200 K
β = 91.987 (3)°Needle, colorless
V = 981.3 (2) Å30.20 × 0.04 × 0.02 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2025 independent reflections
Radiation source: fine focus sealed Siemens Mo tube1416 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
0.3° wide ω exposures scansθmax = 26.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)		h = −15→15
Tmin = 0.973, Tmax = 0.993k = −6→6
9953 measured reflectionsl = −18→18
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0798P)2 + 0.0818P]
where P = (Fo2 + 2Fc2)/3
2025 reflections(Δ/σ)max < 0.001
130 parametersΔρmax = 0.19 e Å−3
0 restraintsΔρmin = −0.14 e Å−3
Crystal data top
C12H10O2V = 981.3 (2) Å3
Mr = 186.20Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.7079 (19) ŵ = 0.09 mm−1
b = 5.1464 (8) ÅT = 200 K
c = 15.014 (2) Å0.20 × 0.04 × 0.02 mm
β = 91.987 (3)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2025 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)		1416 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.993Rint = 0.023
9953 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.19 e Å−3
2025 reflectionsΔρmin = −0.14 e Å−3
130 parameters
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
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) top
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, º) top
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, º) top
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.

Experimental details

Crystal data
Chemical formulaC12H10O2
Mr186.20
Crystal system, space groupMonoclinic, P21/c
Temperature (K)200
a, b, c (Å)12.7079 (19), 5.1464 (8), 15.014 (2)
β (°) 91.987 (3)
V (Å3)981.3 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.20 × 0.04 × 0.02
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1997)
Tmin, Tmax0.973, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections		9953, 2025, 1416
Rint0.023
(sin θ/λ)max (Å−1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.148, 1.04
No. of reflections2025
No. of parameters130
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.19, −0.14

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.932.613.541 (2)176.8
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.
 

Acknowledgements

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

References

First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationBruker (2001). SAINT-Plus and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruno, 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.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationRajan, S. S. (1978). Acta Cryst. B34, 998–1000.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
 First citationSheldrick, G. M. (1997). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 12| December 2008| Page o2310
doi:10.1107/S1600536808036246
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