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organic compounds
The molecule of the title compound, C13H9NO2, is planar, and is disordered so that there are two conformations (1:1) of the phenol ring with respect to the benzoxazole group. Strong intermolecular π–π interactions are noted in the crystal structure.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027066/tk6249sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027066/tk6249Isup2.hkl |
CCDC reference: 285522
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
![[sigma]](//journals.iucr.org/logos/entities/sigma_rmgif.gif)
(N-C) = 0.005 Å - Disorder in main residue
- R factor = 0.059
- wR factor = 0.170
- Data-to-parameter ratio = 9.4
![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(N-C) = 0.005 ÅcheckCIF/PLATON results
No syntax errors found
Alert level B PLAT301_ALERT_3_B Main Residue Disorder ......................... 30.00 Perc.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1' PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.20 From the CIF: _reflns_number_total 1272 Count of symmetry unique reflns 1287 Completeness (_total/calc) 98.83% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Alert level B
Alert level C
Alert level G
Computing details top
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXL97.
2-(2-Hydroxyphenyl)-1,3-benzoxazole top
Crystal data top
| C13H9NO2 | F(000) = 440 |
| Mr = 211.21 | Dx = 1.404 Mg m−3 |
| Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2c -2n | Cell parameters from 1095 reflections |
| a = 22.446 (3) Å | θ = 2.5–23.7° |
| b = 3.8547 (5) Å | µ = 0.10 mm−1 |
| c = 11.5504 (15) Å | T = 293 K |
| V = 999.4 (2) Å3 | Block, colourless |
| Z = 4 | 0.40 × 0.23 × 0.18 mm |
Data collection top
| Bruker APEX CCD area-detector diffractometer | 1272 independent reflections |
| Radiation source: fine-focus sealed tube | 935 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.024 |
| φ and ω scans | θmax = 28.2°, θmin = 1.8° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −26→29 |
| Tmin = 0.963, Tmax = 0.983 | k = −5→4 |
| 5770 measured reflections | l = −14→15 |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
| wR(F2) = 0.170 | w = 1/[σ2(Fo2) + (0.079P)2 + 0.2556P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.08 | (Δ/σ)max = 0.001 |
| 1272 reflections | Δρmax = 0.23 e Å−3 |
| 136 parameters | Δρmin = −0.24 e Å−3 |
| 3 restraints | Absolute structure: Flack (1983), with 1079 Friedel pairs |
| Primary atom site location: structure-invariant direct methods |
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) | |
| O1 | 0.3440 (3) | 0.619 (3) | 0.4371 (5) | 0.081 (3) | 0.50 |
| H1 | 0.3797 | 0.5766 | 0.4315 | 0.121* | 0.50 |
| C1 | 0.3219 (4) | 0.689 (3) | 0.3333 (8) | 0.0546 (15) | 0.50 |
| C2 | 0.2661 (3) | 0.839 (3) | 0.3197 (7) | 0.0636 (17) | 0.50 |
| H2 | 0.2435 | 0.8972 | 0.3845 | 0.076* | 0.50 |
| C3 | 0.2440 (4) | 0.904 (4) | 0.2094 (8) | 0.070 (3) | 0.50 |
| H3 | 0.2066 | 1.0043 | 0.2003 | 0.083* | 0.50 |
| C4 | 0.2777 (4) | 0.817 (4) | 0.1126 (7) | 0.078 (2) | 0.50 |
| H4 | 0.2628 | 0.8602 | 0.0388 | 0.094* | 0.50 |
| C5 | 0.3335 (4) | 0.667 (4) | 0.1262 (9) | 0.070 (2) | 0.50 |
| H5 | 0.3560 | 0.6088 | 0.0615 | 0.085* | 0.50 |
| C6 | 0.3556 (3) | 0.602 (4) | 0.2365 (11) | 0.0537 (8) | 0.50 |
| O1' | 0.3434 (4) | 0.613 (3) | 0.0340 (4) | 0.083 (3) | 0.50 |
| H1' | 0.3770 | 0.5315 | 0.0404 | 0.124* | 0.50 |
| C6' | 0.3558 (4) | 0.604 (4) | 0.2347 (10) | 0.0537 (8) | 0.50 |
| C5' | 0.3331 (4) | 0.665 (4) | 0.3449 (8) | 0.070 (2) | 0.50 |
| H5' | 0.3553 | 0.6042 | 0.4098 | 0.085* | 0.50 |
| C4' | 0.2773 (4) | 0.817 (3) | 0.3580 (7) | 0.078 (2) | 0.50 |
| H4' | 0.2622 | 0.8573 | 0.4316 | 0.094* | 0.50 |
| C3' | 0.2442 (4) | 0.907 (4) | 0.2609 (9) | 0.070 (3) | 0.50 |
| H3' | 0.2069 | 1.0087 | 0.2696 | 0.083* | 0.50 |
| C2' | 0.2668 (4) | 0.846 (3) | 0.1507 (7) | 0.0636 (17) | 0.50 |
| H2' | 0.2447 | 0.9070 | 0.0858 | 0.076* | 0.50 |
| C1' | 0.3226 (3) | 0.695 (3) | 0.1377 (8) | 0.0546 (15) | 0.50 |
| C7 | 0.41492 (13) | 0.4537 (7) | 0.2418 (5) | 0.0528 (8) | |
| C8 | 0.49790 (10) | 0.2516 (7) | 0.2951 (4) | 0.0501 (11) | |
| C9 | 0.54814 (17) | 0.1364 (11) | 0.3540 (3) | 0.089 (2) | |
| H9 | 0.5486 | 0.1348 | 0.4345 | 0.107* | |
| C10 | 0.59777 (11) | 0.0238 (7) | 0.2926 (4) | 0.0695 (16) | |
| H10 | 0.6314 | −0.0532 | 0.3320 | 0.083* | |
| C11 | 0.59714 (8) | 0.0264 (7) | 0.1722 (4) | 0.0757 (18) | |
| H11 | 0.6303 | −0.0490 | 0.1311 | 0.091* | |
| C12 | 0.54689 (14) | 0.1415 (11) | 0.1133 (3) | 0.0552 (12) | |
| H12 | 0.5465 | 0.1431 | 0.0328 | 0.066* | |
| C13 | 0.49727 (8) | 0.2541 (7) | 0.1747 (4) | 0.0640 (15) | |
| N1 | 0.44325 (15) | 0.3831 (10) | 0.3339 (3) | 0.0444 (8) | |
| O2 | 0.44484 (15) | 0.3769 (11) | 0.1404 (3) | 0.0713 (12) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.041 (4) | 0.109 (9) | 0.092 (5) | 0.005 (5) | 0.020 (3) | −0.009 (5) |
| C1 | 0.039 (2) | 0.046 (3) | 0.078 (4) | −0.002 (2) | −0.012 (4) | −0.001 (6) |
| C2 | 0.039 (2) | 0.052 (3) | 0.100 (5) | 0.001 (2) | −0.024 (5) | −0.001 (6) |
| C3 | 0.055 (2) | 0.047 (2) | 0.106 (9) | 0.0031 (15) | 0.002 (8) | −0.010 (9) |
| C4 | 0.066 (4) | 0.058 (3) | 0.110 (6) | 0.005 (3) | −0.031 (6) | 0.003 (7) |
| C5 | 0.056 (4) | 0.059 (4) | 0.097 (6) | 0.003 (3) | 0.012 (6) | 0.020 (8) |
| C6 | 0.0465 (15) | 0.0436 (15) | 0.071 (2) | −0.0105 (11) | −0.005 (3) | 0.014 (3) |
| O1' | 0.081 (6) | 0.123 (9) | 0.045 (4) | 0.001 (6) | 0.008 (3) | 0.009 (5) |
| C6' | 0.0465 (15) | 0.0436 (15) | 0.071 (2) | −0.0105 (11) | −0.005 (3) | 0.014 (3) |
| C5' | 0.056 (4) | 0.059 (4) | 0.097 (6) | 0.003 (3) | 0.012 (6) | 0.020 (8) |
| C4' | 0.066 (4) | 0.058 (3) | 0.110 (6) | 0.005 (3) | −0.031 (6) | 0.003 (7) |
| C3' | 0.055 (2) | 0.047 (2) | 0.106 (9) | 0.0031 (15) | 0.002 (8) | −0.010 (9) |
| C2' | 0.039 (2) | 0.052 (3) | 0.100 (5) | 0.001 (2) | −0.024 (5) | −0.001 (6) |
| C1' | 0.039 (2) | 0.046 (3) | 0.078 (4) | −0.002 (2) | −0.012 (4) | −0.001 (6) |
| C7 | 0.0524 (16) | 0.0440 (15) | 0.062 (2) | −0.0115 (12) | 0.016 (3) | 0.012 (3) |
| C8 | 0.037 (2) | 0.043 (3) | 0.070 (3) | 0.0028 (18) | 0.0074 (18) | −0.007 (2) |
| C9 | 0.096 (5) | 0.070 (4) | 0.102 (5) | −0.027 (4) | −0.017 (4) | 0.013 (4) |
| C10 | 0.045 (3) | 0.059 (4) | 0.104 (4) | 0.007 (2) | −0.016 (3) | 0.002 (3) |
| C11 | 0.059 (4) | 0.059 (4) | 0.109 (5) | −0.009 (3) | −0.011 (3) | −0.010 (4) |
| C12 | 0.038 (2) | 0.066 (3) | 0.062 (3) | 0.003 (2) | 0.001 (2) | −0.011 (3) |
| C13 | 0.066 (3) | 0.056 (3) | 0.070 (3) | −0.025 (3) | 0.017 (2) | −0.016 (2) |
| N1 | 0.0410 (18) | 0.047 (2) | 0.0454 (15) | −0.0017 (19) | −0.0009 (15) | 0.0050 (18) |
| O2 | 0.0500 (19) | 0.081 (3) | 0.083 (2) | −0.005 (2) | 0.0015 (17) | 0.001 (2) |
Geometric parameters (Å, º) top
| O1—C1 | 1.325 (8) | C4'—C3' | 1.3900 |
| O1—H1 | 0.8200 | C4'—H4' | 0.9300 |
| C1—C2 | 1.3900 | C3'—C2' | 1.3900 |
| C1—C6 | 1.3900 | C3'—H3' | 0.9300 |
| C2—C3 | 1.3900 | C2'—C1' | 1.3900 |
| C2—H2 | 0.9300 | C2'—H2' | 0.9300 |
| C3—C4 | 1.3900 | C7—N1 | 1.269 (6) |
| C3—H3 | 0.9300 | C7—O2 | 1.383 (6) |
| C4—C5 | 1.3900 | C8—C9 | 1.3900 |
| C4—H4 | 0.9300 | C8—C13 | 1.3900 |
| C5—C6 | 1.3900 | C8—N1 | 1.401 (4) |
| C5—H5 | 0.9300 | C9—C10 | 1.3900 |
| C6—C7 | 1.450 (4) | C9—H9 | 0.9300 |
| O1'—C1' | 1.323 (8) | C10—C11 | 1.3900 |
| O1'—H1' | 0.8200 | C10—H10 | 0.9300 |
| C6'—C5' | 1.3900 | C11—C12 | 1.3900 |
| C6'—C1' | 1.3900 | C11—H11 | 0.9300 |
| C6'—C7 | 1.451 (4) | C12—C13 | 1.3900 |
| C5'—C4' | 1.3900 | C12—H12 | 0.9300 |
| C5'—H5' | 0.9300 | C13—O2 | 1.329 (4) |
| C1—O1—H1 | 109.5 | C3'—C2'—C1' | 120.0 |
| O1—C1—C2 | 121.6 (8) | C3'—C2'—H2' | 120.0 |
| O1—C1—C6 | 118.4 (8) | C1'—C2'—H2' | 120.0 |
| C2—C1—C6 | 120.0 | O1'—C1'—C2' | 121.0 (7) |
| C3—C2—C1 | 120.0 | O1'—C1'—C6' | 118.8 (7) |
| C3—C2—H2 | 120.0 | C2'—C1'—C6' | 120.0 |
| C1—C2—H2 | 120.0 | N1—C7—O2 | 114.9 (3) |
| C4—C3—C2 | 120.0 | N1—C7—C6 | 125.5 (6) |
| C4—C3—H3 | 120.0 | O2—C7—C6 | 119.7 (6) |
| C2—C3—H3 | 120.0 | N1—C7—C6' | 126.3 (6) |
| C3—C4—C5 | 120.0 | O2—C7—C6' | 118.8 (6) |
| C3—C4—H4 | 120.0 | C9—C8—C13 | 120.0 |
| C5—C4—H4 | 120.0 | C9—C8—N1 | 132.0 (3) |
| C6—C5—C4 | 120.0 | C13—C8—N1 | 108.0 (3) |
| C6—C5—H5 | 120.0 | C8—C9—C10 | 120.0 |
| C4—C5—H5 | 120.0 | C8—C9—H9 | 120.0 |
| C5—C6—C1 | 120.0 | C10—C9—H9 | 120.0 |
| C5—C6—C7 | 115.9 (8) | C11—C10—C9 | 120.0 |
| C1—C6—C7 | 124.1 (8) | C11—C10—H10 | 120.0 |
| C1'—O1'—H1' | 109.5 | C9—C10—H10 | 120.0 |
| C5'—C6'—C1' | 120.0 | C12—C11—C10 | 120.0 |
| C5'—C6'—C7 | 110.5 (7) | C12—C11—H11 | 120.0 |
| C1'—C6'—C7 | 129.4 (7) | C10—C11—H11 | 120.0 |
| C6'—C5'—C4' | 120.0 | C11—C12—C13 | 120.0 |
| C6'—C5'—H5' | 120.0 | C11—C12—H12 | 120.0 |
| C4'—C5'—H5' | 120.0 | C13—C12—H12 | 120.0 |
| C3'—C4'—C5' | 120.0 | O2—C13—C12 | 131.9 (3) |
| C3'—C4'—H4' | 120.0 | O2—C13—C8 | 108.1 (3) |
| C5'—C4'—H4' | 120.0 | C12—C13—C8 | 120.0 |
| C2'—C3'—C4' | 120.0 | C7—N1—C8 | 104.4 (3) |
| C2'—C3'—H3' | 120.0 | C13—O2—C7 | 104.7 (4) |
| C4'—C3'—H3' | 120.0 |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1′—H1′···O2 | 0.82 | 2.00 | 2.743 (9) | 150 |
| O1—H1···N1 | 0.82 | 1.97 | 2.686 (8) | 146 |
