journal menu
organic compounds
2-(1-Naphthyl)propionic acid, C13H12O2, is one of the chiral compounds which exhibit the highest difference (80 K) in melting points between the racemic and enantiomeric crystals. We report here the structure of the racemic compound.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805004125/er6003sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536805004125/er6003Isup2.hkl |
CCDC reference: 271866
Key indicators
- Single-crystal X-ray study
- T = 122 K
- Mean
![[sigma]](//journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.002 Å - R factor = 0.055
- wR factor = 0.161
- Data-to-parameter ratio = 14.2
![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C) = 0.002 ÅcheckCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.19 PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 .. O2 .. 2.64 Ang. PLAT707_ALERT_1_C D...A Calc 3.431(2), Rep 3.4331(18), Dev.. 1.05 Sigma C8 -O2 1.555 4.655
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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Alert level C
Computing details top
Data collection: KappaCCD; cell refinement: DIRAX/LSQ (Duisenberg et al., 2003); data reduction: EVALCCD (Duisenberg, 2003); program(s) used to solve structure: SIR97(Altomare et al., 1996); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
2-(1-naphtyl)propionic acid top
Crystal data top
| C13H12O2 | F(000) = 424 |
| Mr = 200.24 | Dx = 1.307 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 11792 reflections |
| a = 7.8089 (4) Å | θ = 1.4–37.0° |
| b = 8.8904 (5) Å | µ = 0.09 mm−1 |
| c = 14.7466 (12) Å | T = 122 K |
| β = 96.143 (7)° | Needle, colorless |
| V = 1017.89 (11) Å3 | 0.48 × 0.36 × 0.09 mm |
| Z = 4 |
Data collection top
| KappaCCD diffractometer | Rint = 0.046 |
| Radiation source: fine-focus sealed tube | θmax = 28.0°, θmin = 2.3° |
| area–detector scans to fill Ewald sphere. | h = −10→10 |
| 25823 measured reflections | k = −11→11 |
| 2456 independent reflections | l = −19→19 |
| 2071 reflections with I > 2σ(I) |
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)] = 0.055 | Only H-atom coordinates refined |
| wR(F2) = 0.161 | w = 1/[σ2(Fo2) + (0.0798P)2 + 0.705P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max = 0.005 |
| 2456 reflections | Δρmax = 0.54 e Å−3 |
| 173 parameters | Δρmin = −0.25 e Å−3 |
| 0 restraints |
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 | ||
| O2 | −0.12399 (15) | 0.14248 (13) | 0.02487 (8) | 0.0257 (3) | |
| O1 | 0.08662 (14) | 0.03349 (13) | 0.11681 (8) | 0.0243 (3) | |
| C5 | 0.21503 (17) | 0.34088 (16) | 0.27007 (10) | 0.0183 (3) | |
| C1 | −0.03778 (17) | 0.13286 (16) | 0.09869 (10) | 0.0187 (3) | |
| C4 | 0.09722 (18) | 0.33986 (16) | 0.18954 (9) | 0.0185 (3) | |
| C10 | 0.36082 (18) | 0.43767 (17) | 0.27460 (10) | 0.0204 (3) | |
| C13 | 0.1256 (2) | 0.43464 (18) | 0.11929 (10) | 0.0237 (3) | |
| C6 | 0.1943 (2) | 0.25099 (18) | 0.34812 (10) | 0.0227 (3) | |
| C2 | −0.06012 (18) | 0.23639 (17) | 0.17781 (10) | 0.0198 (3) | |
| C8 | 0.4576 (2) | 0.3505 (2) | 0.42651 (11) | 0.0281 (4) | |
| C12 | 0.2686 (2) | 0.53317 (18) | 0.12373 (11) | 0.0259 (3) | |
| C9 | 0.48078 (19) | 0.43895 (19) | 0.35368 (11) | 0.0258 (3) | |
| C11 | 0.3845 (2) | 0.53331 (19) | 0.19959 (11) | 0.0255 (3) | |
| C3 | −0.22741 (19) | 0.32487 (19) | 0.16441 (11) | 0.0239 (3) | |
| C7 | 0.3111 (2) | 0.2565 (2) | 0.42375 (11) | 0.0278 (3) | |
| H13 | 0.037 (3) | 0.435 (2) | 0.0645 (14) | 0.028* | |
| H6 | 0.096 (3) | 0.188 (3) | 0.3501 (14) | 0.027* | |
| H2 | −0.066 (3) | 0.172 (2) | 0.2287 (14) | 0.024* | |
| H8 | 0.540 (3) | 0.353 (2) | 0.4801 (15) | 0.034* | |
| H12 | 0.279 (3) | 0.600 (3) | 0.0735 (15) | 0.031* | |
| H9 | 0.588 (3) | 0.511 (3) | 0.3521 (15) | 0.031* | |
| H11 | 0.472 (3) | 0.596 (3) | 0.1996 (15) | 0.031* | |
| H3A | −0.227 (3) | 0.392 (2) | 0.1114 (15) | 0.029* | |
| H3B | −0.237 (3) | 0.391 (2) | 0.2183 (14) | 0.029* | |
| H3C | −0.324 (3) | 0.255 (2) | 0.1582 (14) | 0.029* | |
| H7 | 0.293 (3) | 0.192 (3) | 0.4768 (15) | 0.033* | |
| H1 | 0.094 (3) | −0.026 (3) | 0.067 (2) | 0.054 (7)* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O2 | 0.0243 (5) | 0.0257 (6) | 0.0251 (5) | 0.0065 (4) | −0.0058 (4) | −0.0060 (4) |
| O1 | 0.0232 (5) | 0.0231 (6) | 0.0251 (5) | 0.0063 (4) | −0.0043 (4) | −0.0043 (4) |
| C5 | 0.0168 (6) | 0.0170 (6) | 0.0213 (6) | −0.0002 (5) | 0.0028 (5) | −0.0025 (5) |
| C1 | 0.0159 (6) | 0.0158 (6) | 0.0242 (7) | −0.0020 (5) | 0.0007 (5) | −0.0018 (5) |
| C4 | 0.0187 (6) | 0.0184 (6) | 0.0184 (6) | −0.0020 (5) | 0.0012 (5) | −0.0011 (5) |
| C10 | 0.0166 (6) | 0.0202 (7) | 0.0243 (7) | −0.0001 (5) | 0.0018 (5) | −0.0057 (5) |
| C13 | 0.0279 (7) | 0.0241 (7) | 0.0194 (6) | −0.0035 (6) | 0.0034 (5) | 0.0010 (5) |
| C6 | 0.0232 (7) | 0.0227 (7) | 0.0220 (7) | 0.0002 (6) | 0.0009 (5) | 0.0028 (5) |
| C2 | 0.0173 (6) | 0.0200 (7) | 0.0218 (7) | −0.0023 (5) | −0.0001 (5) | −0.0020 (5) |
| C8 | 0.0258 (7) | 0.0300 (8) | 0.0262 (8) | 0.0052 (6) | −0.0073 (6) | −0.0048 (6) |
| C12 | 0.0322 (8) | 0.0235 (7) | 0.0229 (7) | −0.0063 (6) | 0.0071 (6) | 0.0017 (6) |
| C9 | 0.0188 (7) | 0.0264 (8) | 0.0314 (8) | −0.0007 (6) | −0.0010 (6) | −0.0069 (6) |
| C11 | 0.0243 (7) | 0.0233 (7) | 0.0295 (8) | −0.0058 (6) | 0.0058 (6) | −0.0028 (6) |
| C3 | 0.0183 (6) | 0.0244 (7) | 0.0289 (8) | 0.0001 (6) | 0.0032 (5) | −0.0033 (6) |
| C7 | 0.0329 (8) | 0.0271 (8) | 0.0227 (7) | 0.0023 (7) | −0.0005 (6) | 0.0032 (6) |
Geometric parameters (Å, º) top
| O2—C1 | 1.2201 (18) | C8—C7 | 1.414 (2) |
| O1—C1 | 1.3190 (17) | C12—C11 | 1.362 (2) |
| C5—C4 | 1.4223 (19) | O1—H1 | 0.92 (3) |
| C5—C10 | 1.4229 (19) | C13—H13 | 1.00 (2) |
| C5—C6 | 1.425 (2) | C6—H6 | 0.95 (2) |
| C1—C2 | 1.511 (2) | C2—H2 | 0.95 (2) |
| C4—C13 | 1.372 (2) | C8—H8 | 0.97 (2) |
| C4—C2 | 1.5298 (19) | C12—H12 | 0.96 (2) |
| C10—C9 | 1.416 (2) | C9—H9 | 1.06 (2) |
| C10—C11 | 1.423 (2) | C11—H11 | 0.88 (2) |
| C13—C12 | 1.415 (2) | C3—H3A | 0.98 (2) |
| C6—C7 | 1.364 (2) | C3—H3B | 1.00 (2) |
| C2—C3 | 1.520 (2) | C3—H3C | 0.98 (2) |
| C8—C9 | 1.359 (2) | C7—H7 | 0.99 (2) |
| C4—C5—C10 | 119.07 (13) | C4—C13—H13 | 117.4 (12) |
| C4—C5—C6 | 123.50 (13) | C12—C13—H13 | 120.2 (12) |
| C10—C5—C6 | 117.43 (13) | C7—C6—H6 | 117.8 (12) |
| O2—C1—O1 | 123.48 (13) | C5—C6—H6 | 121.0 (12) |
| O2—C1—C2 | 123.23 (13) | C1—C2—H2 | 105.3 (12) |
| O1—C1—C2 | 113.27 (12) | C3—C2—H2 | 107.6 (12) |
| C13—C4—C5 | 118.96 (13) | C4—C2—H2 | 112.1 (12) |
| C13—C4—C2 | 118.48 (13) | C9—C8—H8 | 120.1 (14) |
| C5—C4—C2 | 122.56 (12) | C7—C8—H8 | 120.2 (13) |
| C9—C10—C5 | 119.95 (14) | C11—C12—H12 | 122.1 (13) |
| C9—C10—C11 | 120.39 (14) | C13—C12—H12 | 118.5 (13) |
| C5—C10—C11 | 119.66 (13) | C8—C9—H9 | 122.7 (12) |
| C4—C13—C12 | 122.40 (14) | C10—C9—H9 | 116.3 (12) |
| C7—C6—C5 | 121.12 (15) | C12—C11—H11 | 116.6 (14) |
| C1—C2—C3 | 112.56 (12) | C10—C11—H11 | 122.9 (14) |
| C1—C2—C4 | 107.21 (11) | C2—C3—H3A | 109.8 (12) |
| C3—C2—C4 | 111.86 (12) | C2—C3—H3B | 109.9 (12) |
| C9—C8—C7 | 119.66 (14) | H3A—C3—H3B | 106.6 (17) |
| C11—C12—C13 | 119.37 (14) | C2—C3—H3C | 109.1 (13) |
| C8—C9—C10 | 120.96 (15) | H3A—C3—H3C | 112.6 (17) |
| C12—C11—C10 | 120.51 (14) | H3B—C3—H3C | 108.9 (17) |
| C6—C7—C8 | 120.86 (15) | C6—C7—H7 | 118.9 (13) |
| C1—O1—H1 | 109.5 (17) | C8—C7—H7 | 120.2 (13) |
| C10—C5—C4—C13 | −1.4 (2) | O1—C1—C2—C4 | 69.85 (15) |
| C6—C5—C4—C13 | 177.72 (14) | C13—C4—C2—C1 | 62.21 (17) |
| C10—C5—C4—C2 | 178.32 (13) | C5—C4—C2—C1 | −117.49 (15) |
| C6—C5—C4—C2 | −2.6 (2) | C13—C4—C2—C3 | −61.64 (18) |
| C4—C5—C10—C9 | −179.19 (14) | C5—C4—C2—C3 | 118.66 (15) |
| C6—C5—C10—C9 | 1.7 (2) | C4—C13—C12—C11 | 1.0 (3) |
| C4—C5—C10—C11 | 1.1 (2) | C7—C8—C9—C10 | −0.4 (2) |
| C6—C5—C10—C11 | −178.01 (14) | C5—C10—C9—C8 | −1.1 (2) |
| C5—C4—C13—C12 | 0.3 (2) | C11—C10—C9—C8 | 178.58 (15) |
| C2—C4—C13—C12 | −179.38 (14) | C13—C12—C11—C10 | −1.3 (2) |
| C4—C5—C6—C7 | −179.87 (15) | C9—C10—C11—C12 | −179.48 (15) |
| C10—C5—C6—C7 | −0.8 (2) | C5—C10—C11—C12 | 0.2 (2) |
| O2—C1—C2—C3 | 14.7 (2) | C5—C6—C7—C8 | −0.7 (2) |
| O1—C1—C2—C3 | −166.73 (13) | C9—C8—C7—C6 | 1.4 (3) |
| O2—C1—C2—C4 | −108.71 (15) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···O2i | 0.91 (3) | 1.74 (3) | 2.6511 (17) | 176 (2) |
| C9—H9···O1ii | 1.06 (2) | 2.54 (2) | 3.4631 (19) | 145 (2) |
| C8—H8···O2iii | 0.96 (3) | 2.64 (2) | 3.4331 (18) | 140 (2) |
| Symmetry codes: (i) −x, −y, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) x+1, −y+1/2, z+1/2. |
