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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019962/dn6090sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019962/dn6090Isup2.hkl
Contains datablock I

CCDC reference: 225775

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.052
  • wR factor = 0.151
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

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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

Computing details top

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
C10H10O3F(000) = 752
Mr = 178.18Dx = 1.287 Mg m3
Monoclinic, P21/cMelting point: 370 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 12.6682 (12) ÅCell parameters from 78 reflections
b = 13.2891 (10) Åθ = 4.7–12.4°
c = 11.5196 (10) ŵ = 0.10 mm1
β = 108.450 (7)°T = 296 K
V = 1839.6 (3) Å3Irregular, colorless
Z = 80.40 × 0.40 × 0.22 mm
Data collection top
Bruker P4
diffractometer
Rint = 0.023
Radiation source: fine-focus sealed tube, FN4θmax = 25.0°, θmin = 2.3°
Graphite monochromatorh = 1415
ω scansk = 151
5486 measured reflectionsl = 135
3231 independent reflections3 standard reflections every 97 reflections
1854 reflections with I > 2σ(I) intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052H-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 reflectionsΔρmax = 0.44 e Å3
255 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXTL-Plus, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/UeqOcc. (<1)
O10.32422 (13)0.05911 (11)0.46645 (15)0.0610 (5)
O20.40633 (15)0.00156 (12)0.33572 (18)0.0784 (6)
O30.47553 (15)0.47624 (11)0.32206 (17)0.0774 (6)
H30.51250.47680.27290.116*
C10.1287 (3)0.0816 (2)0.5377 (3)0.0960 (10)
H1A0.09500.11270.46280.115*
H1B0.09110.07710.59500.115*
C20.2267 (3)0.0449 (2)0.5619 (3)0.0883 (9)
H2A0.25600.01470.63820.106*
C30.2962 (2)0.04468 (18)0.4864 (3)0.0746 (8)
H3B0.25790.07630.40850.089*
H3C0.36360.08250.52550.089*
C40.37965 (19)0.07218 (18)0.3871 (2)0.0534 (6)
C50.40404 (18)0.17856 (16)0.3702 (2)0.0479 (6)
C60.4572 (2)0.20433 (17)0.2854 (2)0.0571 (6)
H6A0.47680.15390.24010.069*
C70.4810 (2)0.30260 (17)0.2674 (2)0.0584 (6)
H7A0.51630.31850.21020.070*
C80.45222 (19)0.37780 (16)0.3343 (2)0.0545 (6)
C90.3985 (2)0.35411 (17)0.4183 (2)0.0629 (7)
H9A0.37870.40480.46310.075*
C100.37458 (19)0.25534 (17)0.4353 (2)0.0557 (6)
H10A0.33800.23980.49150.067*
O110.18660 (14)0.03213 (12)0.05024 (16)0.0666 (5)
O120.08184 (16)0.08648 (13)0.15985 (17)0.0767 (6)
O130.09097 (15)0.38797 (12)0.24491 (17)0.0760 (6)
H130.04550.39170.27580.114*
C1110.2611 (18)0.1938 (10)0.1544 (13)0.084 (3)0.50 (3)
H11A0.19660.23200.18330.100*0.50 (3)
H11B0.31300.19380.19620.100*0.50 (3)
C1210.2790 (14)0.1397 (11)0.0542 (17)0.070 (3)0.50 (3)
H12A0.34420.10210.02710.084*0.50 (3)
C1120.3158 (17)0.1815 (10)0.106 (2)0.086 (4)0.50 (3)
H11C0.35080.22690.04450.103*0.50 (3)
H11D0.33830.17630.17530.103*0.50 (3)
C1220.2365 (16)0.1261 (10)0.0958 (16)0.070 (3)0.50 (3)
H12B0.20110.08060.15710.084*0.50 (3)
C130.2011 (2)0.13569 (19)0.0169 (3)0.0751 (8)
H13A0.12990.16330.03120.090*
H13B0.22970.17600.09040.090*
C140.12521 (19)0.01688 (18)0.1237 (2)0.0559 (6)
C150.11766 (18)0.08936 (16)0.1549 (2)0.0492 (6)
C160.15849 (19)0.16667 (18)0.1001 (2)0.0578 (6)
H16A0.19270.15150.04170.069*
C170.1490 (2)0.26523 (19)0.1312 (2)0.0635 (7)
H17A0.17700.31620.09400.076*
C180.09785 (19)0.28909 (18)0.2178 (2)0.0558 (6)
C190.0574 (2)0.21316 (18)0.2729 (2)0.0601 (7)
H19A0.02340.22860.33140.072*
C200.0672 (2)0.11486 (18)0.2420 (2)0.0594 (7)
H20A0.03950.06420.28000.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0747 (11)0.0414 (9)0.0810 (12)0.0004 (8)0.0445 (10)0.0085 (8)
O20.1058 (14)0.0419 (10)0.1120 (15)0.0006 (9)0.0695 (12)0.0066 (10)
O30.1151 (15)0.0384 (9)0.1020 (14)0.0048 (9)0.0674 (12)0.0006 (9)
C10.100 (2)0.090 (2)0.119 (3)0.0136 (19)0.064 (2)0.0112 (19)
C20.105 (2)0.0689 (19)0.106 (2)0.0103 (17)0.056 (2)0.0147 (17)
C30.0811 (18)0.0461 (15)0.112 (2)0.0014 (13)0.0530 (17)0.0146 (15)
C40.0557 (14)0.0453 (14)0.0666 (16)0.0003 (11)0.0300 (13)0.0007 (12)
C50.0531 (13)0.0395 (13)0.0567 (14)0.0028 (10)0.0254 (11)0.0009 (11)
C60.0774 (16)0.0429 (13)0.0655 (16)0.0020 (12)0.0431 (14)0.0023 (11)
C70.0803 (17)0.0443 (14)0.0650 (16)0.0006 (11)0.0434 (14)0.0026 (12)
C80.0663 (14)0.0387 (13)0.0656 (16)0.0004 (11)0.0309 (13)0.0028 (12)
C90.0849 (17)0.0423 (14)0.0777 (17)0.0018 (12)0.0488 (15)0.0073 (12)
C100.0668 (15)0.0479 (15)0.0644 (16)0.0004 (11)0.0379 (13)0.0017 (12)
O110.0871 (12)0.0488 (10)0.0803 (12)0.0008 (8)0.0500 (10)0.0049 (9)
O120.1037 (14)0.0513 (10)0.0968 (14)0.0101 (9)0.0627 (12)0.0008 (10)
O130.0985 (13)0.0476 (10)0.1002 (14)0.0037 (9)0.0575 (11)0.0039 (9)
C1110.090 (8)0.079 (6)0.085 (8)0.011 (6)0.032 (6)0.008 (5)
C1210.062 (7)0.065 (5)0.083 (9)0.021 (5)0.023 (6)0.008 (5)
C1120.092 (10)0.078 (6)0.103 (10)0.012 (6)0.053 (8)0.000 (6)
C1220.078 (8)0.059 (5)0.076 (8)0.025 (5)0.028 (6)0.003 (5)
C130.101 (2)0.0528 (16)0.082 (2)0.0042 (14)0.0445 (17)0.0060 (14)
C140.0618 (14)0.0553 (16)0.0562 (15)0.0002 (12)0.0266 (13)0.0017 (12)
C150.0511 (13)0.0478 (14)0.0538 (14)0.0004 (10)0.0238 (11)0.0020 (11)
C160.0663 (15)0.0523 (15)0.0667 (16)0.0014 (12)0.0380 (13)0.0018 (12)
C170.0757 (17)0.0506 (15)0.0793 (18)0.0015 (12)0.0462 (15)0.0060 (13)
C180.0576 (14)0.0490 (14)0.0649 (16)0.0040 (11)0.0250 (13)0.0004 (12)
C190.0717 (16)0.0558 (15)0.0642 (16)0.0038 (12)0.0377 (13)0.0014 (13)
C200.0726 (16)0.0492 (15)0.0672 (16)0.0017 (12)0.0374 (14)0.0054 (12)
Geometric parameters (Å, º) top
O1—C41.328 (3)O13—C181.360 (3)
O1—C31.460 (3)O13—H130.7680
O2—C41.214 (3)C111—C1211.32 (3)
O3—C81.358 (3)C111—H11A0.9300
O3—H30.8414C111—H11B0.9300
C1—C21.280 (4)C121—C131.469 (15)
C1—H1A0.9300C121—H12A0.9300
C1—H1B0.9300C112—C1221.28 (3)
C2—C31.420 (4)C112—H11C0.9300
C2—H2A0.9300C112—H11D0.9300
C3—H3B0.9700C122—C131.506 (15)
C3—H3C0.9700C122—H12B0.9300
C4—C51.473 (3)C13—H13A0.9700
C5—C101.386 (3)C13—H13B0.9700
C5—C61.393 (3)C14—C151.467 (3)
C6—C71.371 (3)C15—C161.388 (3)
C6—H6A0.9300C15—C201.392 (3)
C7—C81.380 (3)C16—C171.373 (3)
C7—H7A0.9300C16—H16A0.9300
C8—C91.383 (3)C17—C181.387 (3)
C9—C101.375 (3)C17—H17A0.9300
C9—H9A0.9300C18—C191.375 (3)
C10—H10A0.9300C19—C201.370 (3)
O11—C141.334 (3)C19—H19A0.9300
O11—C131.456 (3)C20—H20A0.9300
O12—C141.215 (3)
C4—O1—C3116.07 (19)C111—C121—C13123.3 (16)
C8—O3—H3105.3C111—C121—H12A118.4
C2—C1—H1A120.0C13—C121—H12A118.4
C2—C1—H1B120.0C122—C112—H11C120.0
H1A—C1—H1B120.0C122—C112—H11D120.0
C1—C2—C3127.9 (3)H11C—C112—H11D120.0
C1—C2—H2A116.1C112—C122—C13119.2 (18)
C3—C2—H2A116.1C112—C122—H12B120.4
C2—C3—O1109.1 (2)C13—C122—H12B120.4
C2—C3—H3B109.9O11—C13—C121110.2 (6)
O1—C3—H3B109.9O11—C13—C122104.2 (5)
C2—C3—H3C109.9O11—C13—H13A109.6
O1—C3—H3C109.9C121—C13—H13A109.6
H3B—C3—H3C108.3C122—C13—H13A90.9
O2—C4—O1121.6 (2)O11—C13—H13B109.6
O2—C4—C5125.1 (2)C121—C13—H13B109.6
O1—C4—C5113.3 (2)C122—C13—H13B131.9
C10—C5—C6118.1 (2)H13A—C13—H13B108.1
C10—C5—C4122.1 (2)O12—C14—O11121.3 (2)
C6—C5—C4119.8 (2)O12—C14—C15125.3 (2)
C7—C6—C5121.2 (2)O11—C14—C15113.4 (2)
C7—C6—H6A119.4C16—C15—C20118.0 (2)
C5—C6—H6A119.4C16—C15—C14122.6 (2)
C6—C7—C8119.7 (2)C20—C15—C14119.4 (2)
C6—C7—H7A120.1C17—C16—C15120.8 (2)
C8—C7—H7A120.1C17—C16—H16A119.6
O3—C8—C7122.3 (2)C15—C16—H16A119.6
O3—C8—C9117.6 (2)C16—C17—C18120.3 (2)
C7—C8—C9120.1 (2)C16—C17—H17A119.8
C10—C9—C8119.8 (2)C18—C17—H17A119.8
C10—C9—H9A120.1O13—C18—C19122.9 (2)
C8—C9—H9A120.1O13—C18—C17117.7 (2)
C9—C10—C5121.1 (2)C19—C18—C17119.4 (2)
C9—C10—H10A119.5C20—C19—C18120.2 (2)
C5—C10—H10A119.5C20—C19—H19A119.9
C14—O11—C13117.31 (19)C18—C19—H19A119.9
C18—O13—H13106.3C19—C20—C15121.3 (2)
C121—C111—H11A120.0C19—C20—H20A119.4
C121—C111—H11B120.0C15—C20—H20A119.4
H11A—C111—H11B120.0
C1—C2—C3—O1121.8 (3)C111—C121—C13—O11135.2 (16)
C4—O1—C3—C2173.4 (2)C111—C121—C13—C12256 (2)
C3—O1—C4—O20.9 (3)C112—C122—C13—O11136.7 (18)
C3—O1—C4—C5179.3 (2)C112—C122—C13—C12129 (2)
O2—C4—C5—C10177.6 (2)C13—O11—C14—O121.1 (4)
O1—C4—C5—C102.2 (3)C13—O11—C14—C15178.5 (2)
O2—C4—C5—C63.2 (4)O12—C14—C15—C16172.6 (2)
O1—C4—C5—C6177.0 (2)O11—C14—C15—C167.9 (3)
C10—C5—C6—C70.7 (4)O12—C14—C15—C207.0 (4)
C4—C5—C6—C7179.9 (2)O11—C14—C15—C20172.6 (2)
C5—C6—C7—C80.1 (4)C20—C15—C16—C170.1 (3)
C6—C7—C8—O3178.7 (2)C14—C15—C16—C17179.5 (2)
C6—C7—C8—C90.7 (4)C15—C16—C17—C180.3 (4)
O3—C8—C9—C10179.0 (2)C16—C17—C18—O13179.9 (2)
C7—C8—C9—C100.4 (4)C16—C17—C18—C190.5 (4)
C8—C9—C10—C50.4 (4)O13—C18—C19—C20179.8 (2)
C6—C5—C10—C91.0 (3)C17—C18—C19—C200.3 (4)
C4—C5—C10—C9179.8 (2)C18—C19—C20—C150.0 (4)
C14—O11—C13—C121174.6 (8)C16—C15—C20—C190.2 (4)
C14—O11—C13—C122160.8 (8)C14—C15—C20—C19179.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.841.882.716 (2)171
O13—H13···O12ii0.772.002.763 (2)173
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y+1/2, z+1/2.
 

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