The crystal structure of the title compound, C10H10O3, has two independent molecules in the asymmetric unit. In one of these molecules, the allyl group is disordered as a consequence of a degree of free rotation of ca 15° around the C—C σ bond of the allyl group.
Supporting information
CCDC reference: 225775
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.052
- wR factor = 0.151
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.55
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.17
PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc.
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
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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: XSCANS 2.21 (Siemens, 1996); cell refinement: XSCANS 2.21 (Siemens, 1996); data reduction: XSCANS 2.21 (Siemens, 1996); program(s) used to solve structure: SHELXTL-Plus 5.10 (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus 5.10 (Sheldrick, 1998); molecular graphics: SHELXTL-Plus 5.10 (Sheldrick, 1998); software used to prepare material for publication: SHELXTL-Plus 5.10 (Sheldrick, 1998).
4-Hydroxy-benzoic acid allyl ester
top
Crystal data top
C10H10O3 | F(000) = 752 |
Mr = 178.18 | Dx = 1.287 Mg m−3 |
Monoclinic, P21/c | Melting point: 370 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 12.6682 (12) Å | Cell parameters from 78 reflections |
b = 13.2891 (10) Å | θ = 4.7–12.4° |
c = 11.5196 (10) Å | µ = 0.10 mm−1 |
β = 108.450 (7)° | T = 296 K |
V = 1839.6 (3) Å3 | Irregular, colorless |
Z = 8 | 0.40 × 0.40 × 0.22 mm |
Data collection top
Bruker P4 diffractometer | Rint = 0.023 |
Radiation source: fine-focus sealed tube, FN4 | θmax = 25.0°, θmin = 2.3° |
Graphite monochromator | h = −14→15 |
ω scans | k = −15→1 |
5486 measured reflections | l = −13→5 |
3231 independent reflections | 3 standard reflections every 97 reflections |
1854 reflections with I > 2σ(I) | intensity decay: 1% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.151 | w = 1/[σ2(Fo2) + (0.0739P)2 + 0.089P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3231 reflections | Δρmax = 0.44 e Å−3 |
255 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXTL-Plus, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0063 (14) |
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. H3 and H13 atoms (hydroxyl groups) found on difference maps,
remaining H atoms placed on idealized positions. Riding refinement for all H
atoms with fixed U isotropic parameters. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.32422 (13) | 0.05911 (11) | 0.46645 (15) | 0.0610 (5) | |
O2 | 0.40633 (15) | 0.00156 (12) | 0.33572 (18) | 0.0784 (6) | |
O3 | 0.47553 (15) | 0.47624 (11) | 0.32206 (17) | 0.0774 (6) | |
H3 | 0.5125 | 0.4768 | 0.2729 | 0.116* | |
C1 | 0.1287 (3) | −0.0816 (2) | 0.5377 (3) | 0.0960 (10) | |
H1A | 0.0950 | −0.1127 | 0.4628 | 0.115* | |
H1B | 0.0911 | −0.0771 | 0.5950 | 0.115* | |
C2 | 0.2267 (3) | −0.0449 (2) | 0.5619 (3) | 0.0883 (9) | |
H2A | 0.2560 | −0.0147 | 0.6382 | 0.106* | |
C3 | 0.2962 (2) | −0.04468 (18) | 0.4864 (3) | 0.0746 (8) | |
H3B | 0.2579 | −0.0763 | 0.4085 | 0.089* | |
H3C | 0.3636 | −0.0825 | 0.5255 | 0.089* | |
C4 | 0.37965 (19) | 0.07218 (18) | 0.3871 (2) | 0.0534 (6) | |
C5 | 0.40404 (18) | 0.17856 (16) | 0.3702 (2) | 0.0479 (6) | |
C6 | 0.4572 (2) | 0.20433 (17) | 0.2854 (2) | 0.0571 (6) | |
H6A | 0.4768 | 0.1539 | 0.2401 | 0.069* | |
C7 | 0.4810 (2) | 0.30260 (17) | 0.2674 (2) | 0.0584 (6) | |
H7A | 0.5163 | 0.3185 | 0.2102 | 0.070* | |
C8 | 0.45222 (19) | 0.37780 (16) | 0.3343 (2) | 0.0545 (6) | |
C9 | 0.3985 (2) | 0.35411 (17) | 0.4183 (2) | 0.0629 (7) | |
H9A | 0.3787 | 0.4048 | 0.4631 | 0.075* | |
C10 | 0.37458 (19) | 0.25534 (17) | 0.4353 (2) | 0.0557 (6) | |
H10A | 0.3380 | 0.2398 | 0.4915 | 0.067* | |
O11 | 0.18660 (14) | −0.03213 (12) | 0.05024 (16) | 0.0666 (5) | |
O12 | 0.08184 (16) | −0.08648 (13) | 0.15985 (17) | 0.0767 (6) | |
O13 | 0.09097 (15) | 0.38797 (12) | 0.24491 (17) | 0.0760 (6) | |
H13 | 0.0455 | 0.3917 | 0.2758 | 0.114* | |
C111 | 0.2611 (18) | −0.1938 (10) | −0.1544 (13) | 0.084 (3) | 0.50 (3) |
H11A | 0.1966 | −0.2320 | −0.1833 | 0.100* | 0.50 (3) |
H11B | 0.3130 | −0.1938 | −0.1962 | 0.100* | 0.50 (3) |
C121 | 0.2790 (14) | −0.1397 (11) | −0.0542 (17) | 0.070 (3) | 0.50 (3) |
H12A | 0.3442 | −0.1021 | −0.0271 | 0.084* | 0.50 (3) |
C112 | 0.3158 (17) | −0.1815 (10) | −0.106 (2) | 0.086 (4) | 0.50 (3) |
H11C | 0.3508 | −0.2269 | −0.0445 | 0.103* | 0.50 (3) |
H11D | 0.3383 | −0.1763 | −0.1753 | 0.103* | 0.50 (3) |
C122 | 0.2365 (16) | −0.1261 (10) | −0.0958 (16) | 0.070 (3) | 0.50 (3) |
H12B | 0.2011 | −0.0806 | −0.1571 | 0.084* | 0.50 (3) |
C13 | 0.2011 (2) | −0.13569 (19) | 0.0169 (3) | 0.0751 (8) | |
H13A | 0.1299 | −0.1633 | −0.0312 | 0.090* | |
H13B | 0.2297 | −0.1760 | 0.0904 | 0.090* | |
C14 | 0.12521 (19) | −0.01688 (18) | 0.1237 (2) | 0.0559 (6) | |
C15 | 0.11766 (18) | 0.08936 (16) | 0.1549 (2) | 0.0492 (6) | |
C16 | 0.15849 (19) | 0.16667 (18) | 0.1001 (2) | 0.0578 (6) | |
H16A | 0.1927 | 0.1515 | 0.0417 | 0.069* | |
C17 | 0.1490 (2) | 0.26523 (19) | 0.1312 (2) | 0.0635 (7) | |
H17A | 0.1770 | 0.3162 | 0.0940 | 0.076* | |
C18 | 0.09785 (19) | 0.28909 (18) | 0.2178 (2) | 0.0558 (6) | |
C19 | 0.0574 (2) | 0.21316 (18) | 0.2729 (2) | 0.0601 (7) | |
H19A | 0.0234 | 0.2286 | 0.3314 | 0.072* | |
C20 | 0.0672 (2) | 0.11486 (18) | 0.2420 (2) | 0.0594 (7) | |
H20A | 0.0395 | 0.0642 | 0.2800 | 0.071* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0747 (11) | 0.0414 (9) | 0.0810 (12) | −0.0004 (8) | 0.0445 (10) | 0.0085 (8) |
O2 | 0.1058 (14) | 0.0419 (10) | 0.1120 (15) | 0.0006 (9) | 0.0695 (12) | −0.0066 (10) |
O3 | 0.1151 (15) | 0.0384 (9) | 0.1020 (14) | −0.0048 (9) | 0.0674 (12) | 0.0006 (9) |
C1 | 0.100 (2) | 0.090 (2) | 0.119 (3) | −0.0136 (19) | 0.064 (2) | 0.0112 (19) |
C2 | 0.105 (2) | 0.0689 (19) | 0.106 (2) | −0.0103 (17) | 0.056 (2) | 0.0147 (17) |
C3 | 0.0811 (18) | 0.0461 (15) | 0.112 (2) | −0.0014 (13) | 0.0530 (17) | 0.0146 (15) |
C4 | 0.0557 (14) | 0.0453 (14) | 0.0666 (16) | 0.0003 (11) | 0.0300 (13) | 0.0007 (12) |
C5 | 0.0531 (13) | 0.0395 (13) | 0.0567 (14) | 0.0028 (10) | 0.0254 (11) | 0.0009 (11) |
C6 | 0.0774 (16) | 0.0429 (13) | 0.0655 (16) | 0.0020 (12) | 0.0431 (14) | −0.0023 (11) |
C7 | 0.0803 (17) | 0.0443 (14) | 0.0650 (16) | −0.0006 (11) | 0.0434 (14) | 0.0026 (12) |
C8 | 0.0663 (14) | 0.0387 (13) | 0.0656 (16) | −0.0004 (11) | 0.0309 (13) | 0.0028 (12) |
C9 | 0.0849 (17) | 0.0423 (14) | 0.0777 (17) | 0.0018 (12) | 0.0488 (15) | −0.0073 (12) |
C10 | 0.0668 (15) | 0.0479 (15) | 0.0644 (16) | 0.0004 (11) | 0.0379 (13) | 0.0017 (12) |
O11 | 0.0871 (12) | 0.0488 (10) | 0.0803 (12) | 0.0008 (8) | 0.0500 (10) | −0.0049 (9) |
O12 | 0.1037 (14) | 0.0513 (10) | 0.0968 (14) | −0.0101 (9) | 0.0627 (12) | −0.0008 (10) |
O13 | 0.0985 (13) | 0.0476 (10) | 0.1002 (14) | 0.0037 (9) | 0.0575 (11) | −0.0039 (9) |
C111 | 0.090 (8) | 0.079 (6) | 0.085 (8) | 0.011 (6) | 0.032 (6) | −0.008 (5) |
C121 | 0.062 (7) | 0.065 (5) | 0.083 (9) | 0.021 (5) | 0.023 (6) | −0.008 (5) |
C112 | 0.092 (10) | 0.078 (6) | 0.103 (10) | 0.012 (6) | 0.053 (8) | 0.000 (6) |
C122 | 0.078 (8) | 0.059 (5) | 0.076 (8) | 0.025 (5) | 0.028 (6) | 0.003 (5) |
C13 | 0.101 (2) | 0.0528 (16) | 0.082 (2) | 0.0042 (14) | 0.0445 (17) | −0.0060 (14) |
C14 | 0.0618 (14) | 0.0553 (16) | 0.0562 (15) | 0.0002 (12) | 0.0266 (13) | 0.0017 (12) |
C15 | 0.0511 (13) | 0.0478 (14) | 0.0538 (14) | 0.0004 (10) | 0.0238 (11) | 0.0020 (11) |
C16 | 0.0663 (15) | 0.0523 (15) | 0.0667 (16) | 0.0014 (12) | 0.0380 (13) | 0.0018 (12) |
C17 | 0.0757 (17) | 0.0506 (15) | 0.0793 (18) | −0.0015 (12) | 0.0462 (15) | 0.0060 (13) |
C18 | 0.0576 (14) | 0.0490 (14) | 0.0649 (16) | 0.0040 (11) | 0.0250 (13) | −0.0004 (12) |
C19 | 0.0717 (16) | 0.0558 (15) | 0.0642 (16) | 0.0038 (12) | 0.0377 (13) | 0.0014 (13) |
C20 | 0.0726 (16) | 0.0492 (15) | 0.0672 (16) | −0.0017 (12) | 0.0374 (14) | 0.0054 (12) |
Geometric parameters (Å, º) top
O1—C4 | 1.328 (3) | O13—C18 | 1.360 (3) |
O1—C3 | 1.460 (3) | O13—H13 | 0.7680 |
O2—C4 | 1.214 (3) | C111—C121 | 1.32 (3) |
O3—C8 | 1.358 (3) | C111—H11A | 0.9300 |
O3—H3 | 0.8414 | C111—H11B | 0.9300 |
C1—C2 | 1.280 (4) | C121—C13 | 1.469 (15) |
C1—H1A | 0.9300 | C121—H12A | 0.9300 |
C1—H1B | 0.9300 | C112—C122 | 1.28 (3) |
C2—C3 | 1.420 (4) | C112—H11C | 0.9300 |
C2—H2A | 0.9300 | C112—H11D | 0.9300 |
C3—H3B | 0.9700 | C122—C13 | 1.506 (15) |
C3—H3C | 0.9700 | C122—H12B | 0.9300 |
C4—C5 | 1.473 (3) | C13—H13A | 0.9700 |
C5—C10 | 1.386 (3) | C13—H13B | 0.9700 |
C5—C6 | 1.393 (3) | C14—C15 | 1.467 (3) |
C6—C7 | 1.371 (3) | C15—C16 | 1.388 (3) |
C6—H6A | 0.9300 | C15—C20 | 1.392 (3) |
C7—C8 | 1.380 (3) | C16—C17 | 1.373 (3) |
C7—H7A | 0.9300 | C16—H16A | 0.9300 |
C8—C9 | 1.383 (3) | C17—C18 | 1.387 (3) |
C9—C10 | 1.375 (3) | C17—H17A | 0.9300 |
C9—H9A | 0.9300 | C18—C19 | 1.375 (3) |
C10—H10A | 0.9300 | C19—C20 | 1.370 (3) |
O11—C14 | 1.334 (3) | C19—H19A | 0.9300 |
O11—C13 | 1.456 (3) | C20—H20A | 0.9300 |
O12—C14 | 1.215 (3) | | |
| | | |
C4—O1—C3 | 116.07 (19) | C111—C121—C13 | 123.3 (16) |
C8—O3—H3 | 105.3 | C111—C121—H12A | 118.4 |
C2—C1—H1A | 120.0 | C13—C121—H12A | 118.4 |
C2—C1—H1B | 120.0 | C122—C112—H11C | 120.0 |
H1A—C1—H1B | 120.0 | C122—C112—H11D | 120.0 |
C1—C2—C3 | 127.9 (3) | H11C—C112—H11D | 120.0 |
C1—C2—H2A | 116.1 | C112—C122—C13 | 119.2 (18) |
C3—C2—H2A | 116.1 | C112—C122—H12B | 120.4 |
C2—C3—O1 | 109.1 (2) | C13—C122—H12B | 120.4 |
C2—C3—H3B | 109.9 | O11—C13—C121 | 110.2 (6) |
O1—C3—H3B | 109.9 | O11—C13—C122 | 104.2 (5) |
C2—C3—H3C | 109.9 | O11—C13—H13A | 109.6 |
O1—C3—H3C | 109.9 | C121—C13—H13A | 109.6 |
H3B—C3—H3C | 108.3 | C122—C13—H13A | 90.9 |
O2—C4—O1 | 121.6 (2) | O11—C13—H13B | 109.6 |
O2—C4—C5 | 125.1 (2) | C121—C13—H13B | 109.6 |
O1—C4—C5 | 113.3 (2) | C122—C13—H13B | 131.9 |
C10—C5—C6 | 118.1 (2) | H13A—C13—H13B | 108.1 |
C10—C5—C4 | 122.1 (2) | O12—C14—O11 | 121.3 (2) |
C6—C5—C4 | 119.8 (2) | O12—C14—C15 | 125.3 (2) |
C7—C6—C5 | 121.2 (2) | O11—C14—C15 | 113.4 (2) |
C7—C6—H6A | 119.4 | C16—C15—C20 | 118.0 (2) |
C5—C6—H6A | 119.4 | C16—C15—C14 | 122.6 (2) |
C6—C7—C8 | 119.7 (2) | C20—C15—C14 | 119.4 (2) |
C6—C7—H7A | 120.1 | C17—C16—C15 | 120.8 (2) |
C8—C7—H7A | 120.1 | C17—C16—H16A | 119.6 |
O3—C8—C7 | 122.3 (2) | C15—C16—H16A | 119.6 |
O3—C8—C9 | 117.6 (2) | C16—C17—C18 | 120.3 (2) |
C7—C8—C9 | 120.1 (2) | C16—C17—H17A | 119.8 |
C10—C9—C8 | 119.8 (2) | C18—C17—H17A | 119.8 |
C10—C9—H9A | 120.1 | O13—C18—C19 | 122.9 (2) |
C8—C9—H9A | 120.1 | O13—C18—C17 | 117.7 (2) |
C9—C10—C5 | 121.1 (2) | C19—C18—C17 | 119.4 (2) |
C9—C10—H10A | 119.5 | C20—C19—C18 | 120.2 (2) |
C5—C10—H10A | 119.5 | C20—C19—H19A | 119.9 |
C14—O11—C13 | 117.31 (19) | C18—C19—H19A | 119.9 |
C18—O13—H13 | 106.3 | C19—C20—C15 | 121.3 (2) |
C121—C111—H11A | 120.0 | C19—C20—H20A | 119.4 |
C121—C111—H11B | 120.0 | C15—C20—H20A | 119.4 |
H11A—C111—H11B | 120.0 | | |
| | | |
C1—C2—C3—O1 | 121.8 (3) | C111—C121—C13—O11 | −135.2 (16) |
C4—O1—C3—C2 | −173.4 (2) | C111—C121—C13—C122 | −56 (2) |
C3—O1—C4—O2 | −0.9 (3) | C112—C122—C13—O11 | 136.7 (18) |
C3—O1—C4—C5 | 179.3 (2) | C112—C122—C13—C121 | 29 (2) |
O2—C4—C5—C10 | −177.6 (2) | C13—O11—C14—O12 | −1.1 (4) |
O1—C4—C5—C10 | 2.2 (3) | C13—O11—C14—C15 | 178.5 (2) |
O2—C4—C5—C6 | 3.2 (4) | O12—C14—C15—C16 | −172.6 (2) |
O1—C4—C5—C6 | −177.0 (2) | O11—C14—C15—C16 | 7.9 (3) |
C10—C5—C6—C7 | 0.7 (4) | O12—C14—C15—C20 | 7.0 (4) |
C4—C5—C6—C7 | 179.9 (2) | O11—C14—C15—C20 | −172.6 (2) |
C5—C6—C7—C8 | 0.1 (4) | C20—C15—C16—C17 | −0.1 (3) |
C6—C7—C8—O3 | 178.7 (2) | C14—C15—C16—C17 | 179.5 (2) |
C6—C7—C8—C9 | −0.7 (4) | C15—C16—C17—C18 | −0.3 (4) |
O3—C8—C9—C10 | −179.0 (2) | C16—C17—C18—O13 | 179.9 (2) |
C7—C8—C9—C10 | 0.4 (4) | C16—C17—C18—C19 | 0.5 (4) |
C8—C9—C10—C5 | 0.4 (4) | O13—C18—C19—C20 | −179.8 (2) |
C6—C5—C10—C9 | −1.0 (3) | C17—C18—C19—C20 | −0.3 (4) |
C4—C5—C10—C9 | 179.8 (2) | C18—C19—C20—C15 | 0.0 (4) |
C14—O11—C13—C121 | −174.6 (8) | C16—C15—C20—C19 | 0.2 (4) |
C14—O11—C13—C122 | 160.8 (8) | C14—C15—C20—C19 | −179.4 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2i | 0.84 | 1.88 | 2.716 (2) | 171 |
O13—H13···O12ii | 0.77 | 2.00 | 2.763 (2) | 173 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2. |