Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030838/hg2238sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030838/hg2238Isup2.hkl |
CCDC reference: 655061
Key indicators
- Single-crystal X-ray study
- T = 223 K
- Mean (C-C) = 0.003 Å
- R factor = 0.048
- wR factor = 0.149
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C1 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C2 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C3 = ... R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 0 ALERT type 5 Informative message, check
To a solution of potassium carbonate (335 mg, 1.31 mmol) in water (10 ml) was added a solution of ±(1R,2S,3R)-phenyl 2-(2-(benzyloxy)-2-oxoethyl)-3- phenylcyclopropanecarboxylate (950 mg, 2.46 mmol) in acetone (10 ml). The mixture was allowed to stir overnight after which time the acetone was removed in vacuo and the aqueous solution acidified (conc. HCl). The solution was then extracted with ethyl acetate (3 x 20 ml), dried (MgSO4), filtered and the volatiles removed in vacuo to give a crude solid consisting of (I) and phenol. Phenol was removed by sublimation and the crude acid recrystallized (dichloromethane/hexanes) to give (I) (701 mg, 92%) as a colourless solid. M.p 409–411 K. Elemental analysis found: C 73.50, H, 5.97%; C19H18O4 requires: C 73.53, H, 5.85%. IR: 2538, 1732, 1682, 1603, 1449, 1240, 1170, 961 cm-1. 1H NMR (CDCl3, 300 MHz) δ 2.03 (t, J = 3.9 Hz, 1H), 2.15–2.26 (m, 3H), 2.91–3.00 (m, 1H), 5.03–5.12 (m, 2H), 7.15–7.34 (m, 10H), 12.20 (bs, 1H). 13C NMR (CDCl3, 75 MHz) δ 24.5, 24.6, 31.3, 32.7, 66.4, 127.0, 128.2, 128.2, 128.4, 128.5, 128.8, 134.8, 135.6, 171.5, 179.6.
All C-bound H atoms were included in the riding-model approximation, with C—H = 0.94 to 0.99 Å, and with Uiso(H) = 1.5Ueq(methyl-C) or 1.2Ueq(remaining-C). The hydroxyl-H atoms were located from a difference map and included so that O—H = 0.84 Å and Uiso(H) = 1.5Ueq(O).
The title compound (I) was synthesized in the course of an investigation of selective deprotections of cyclopropanes generated through the reaction of 1,2-dioxines and stabilized phosphorus ylides (Avery et al., 2000, 2001). The molecular structure (Fig. 1) shows the carboxylic acid functional group at the C1 atom to lie to the opposite side of the cyclopropane ring to the substituents at the C2 and C3 atoms. Centrosymmetrically related molecules are connected by the familiar {···HOC=O}2 synthon and these are connected into a double layer via C—H···O contacts (Table 1). The double layers thus formed stack along the c-direction, being separated by hydrophobic interactions (Fig. 2).
For related literature, see: Avery et al. (2000, 2001).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97.
C19H18O4 | Z = 2 |
Mr = 310.33 | F(000) = 328 |
Triclinic, P1 | Dx = 1.288 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 5.5550 (5) Å | Cell parameters from 1829 reflections |
b = 8.9606 (8) Å | θ = 2.5–29.3° |
c = 16.6586 (16) Å | µ = 0.09 mm−1 |
α = 101.698 (2)° | T = 223 K |
β = 98.907 (2)° | Prism, colourless |
γ = 92.186 (2)° | 0.39 × 0.09 × 0.08 mm |
V = 800.11 (13) Å3 |
Bruker SMART CCD area-detector diffractometer | 2831 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.015 |
Graphite monochromator | θmax = 27.5°, θmin = 1.3° |
ω and φ scans | h = −6→7 |
5723 measured reflections | k = −11→11 |
3668 independent reflections | l = −16→21 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0829P)2 + 0.0916P] where P = (Fo2 + 2Fc2)/3 |
3668 reflections | (Δ/σ)max < 0.001 |
211 parameters | Δρmax = 0.28 e Å−3 |
1 restraint | Δρmin = −0.25 e Å−3 |
C19H18O4 | γ = 92.186 (2)° |
Mr = 310.33 | V = 800.11 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.5550 (5) Å | Mo Kα radiation |
b = 8.9606 (8) Å | µ = 0.09 mm−1 |
c = 16.6586 (16) Å | T = 223 K |
α = 101.698 (2)° | 0.39 × 0.09 × 0.08 mm |
β = 98.907 (2)° |
Bruker SMART CCD area-detector diffractometer | 2831 reflections with I > 2σ(I) |
5723 measured reflections | Rint = 0.015 |
3668 independent reflections |
R[F2 > 2σ(F2)] = 0.048 | 1 restraint |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.28 e Å−3 |
3668 reflections | Δρmin = −0.25 e Å−3 |
211 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.6349 (2) | 0.36870 (14) | 0.37643 (10) | 0.0613 (4) | |
O2 | 0.3799 (2) | 0.16367 (12) | 0.36059 (7) | 0.0399 (3) | |
O3 | −0.1845 (2) | 0.82536 (12) | 0.46136 (7) | 0.0394 (3) | |
H3O | −0.1801 | 0.9142 | 0.4903 | 0.059* | |
O4 | 0.1916 (2) | 0.90033 (12) | 0.44703 (8) | 0.0452 (3) | |
C1 | 0.0252 (3) | 0.65051 (15) | 0.38033 (9) | 0.0302 (3) | |
H1 | −0.1308 | 0.5863 | 0.3652 | 0.036* | |
C2 | 0.2544 (3) | 0.56716 (15) | 0.39526 (9) | 0.0303 (3) | |
H2 | 0.3883 | 0.6259 | 0.4373 | 0.036* | |
C3 | 0.1967 (3) | 0.62665 (16) | 0.31702 (9) | 0.0310 (3) | |
H3 | 0.2983 | 0.7201 | 0.3174 | 0.037* | |
C4 | 0.0177 (3) | 0.80346 (16) | 0.43215 (9) | 0.0304 (3) | |
C5 | 0.2214 (3) | 0.40048 (16) | 0.39673 (10) | 0.0329 (3) | |
H5A | 0.1921 | 0.3908 | 0.4520 | 0.040* | |
H5B | 0.0766 | 0.3547 | 0.3565 | 0.040* | |
C6 | 0.4366 (3) | 0.31359 (16) | 0.37669 (9) | 0.0311 (3) | |
C7 | 0.5724 (3) | 0.06418 (18) | 0.34375 (11) | 0.0406 (4) | |
H7A | 0.5573 | −0.0223 | 0.3709 | 0.049* | |
H7B | 0.7306 | 0.1202 | 0.3678 | 0.049* | |
C8 | 0.5662 (3) | 0.00447 (18) | 0.25231 (10) | 0.0383 (4) | |
C9 | 0.3839 (4) | 0.0327 (2) | 0.19188 (12) | 0.0541 (5) | |
H9 | 0.2593 | 0.0952 | 0.2071 | 0.065* | |
C10 | 0.3848 (4) | −0.0311 (3) | 0.10899 (13) | 0.0675 (6) | |
H10 | 0.2614 | −0.0104 | 0.0682 | 0.081* | |
C11 | 0.5631 (4) | −0.1240 (3) | 0.08567 (13) | 0.0633 (6) | |
H11 | 0.5609 | −0.1678 | 0.0293 | 0.076* | |
C12 | 0.7448 (4) | −0.1528 (3) | 0.14513 (14) | 0.0658 (6) | |
H12 | 0.8676 | −0.2164 | 0.1295 | 0.079* | |
C13 | 0.7477 (4) | −0.0882 (2) | 0.22818 (12) | 0.0528 (5) | |
H13 | 0.8740 | −0.1073 | 0.2686 | 0.063* | |
C14 | 0.1254 (3) | 0.52696 (17) | 0.23264 (9) | 0.0353 (3) | |
C15 | 0.2719 (4) | 0.5390 (2) | 0.17366 (11) | 0.0518 (5) | |
H15 | 0.4093 | 0.6094 | 0.1877 | 0.062* | |
C16 | 0.2179 (4) | 0.4483 (3) | 0.09420 (12) | 0.0691 (6) | |
H16 | 0.3182 | 0.4582 | 0.0547 | 0.083* | |
C17 | 0.0195 (4) | 0.3443 (3) | 0.07291 (12) | 0.0686 (6) | |
H17 | −0.0164 | 0.2829 | 0.0191 | 0.082* | |
C18 | −0.1257 (4) | 0.3304 (3) | 0.13032 (13) | 0.0642 (6) | |
H18 | −0.2607 | 0.2582 | 0.1160 | 0.077* | |
C19 | −0.0758 (3) | 0.4221 (2) | 0.20976 (11) | 0.0493 (4) | |
H19 | −0.1794 | 0.4128 | 0.2483 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0349 (7) | 0.0366 (7) | 0.1152 (12) | 0.0015 (5) | 0.0257 (7) | 0.0124 (7) |
O2 | 0.0382 (6) | 0.0256 (5) | 0.0574 (7) | 0.0056 (4) | 0.0150 (5) | 0.0061 (5) |
O3 | 0.0428 (6) | 0.0286 (5) | 0.0475 (7) | 0.0068 (5) | 0.0182 (5) | 0.0005 (5) |
O4 | 0.0479 (7) | 0.0284 (6) | 0.0572 (7) | −0.0027 (5) | 0.0216 (5) | −0.0047 (5) |
C1 | 0.0340 (7) | 0.0239 (7) | 0.0332 (7) | 0.0029 (5) | 0.0096 (6) | 0.0038 (5) |
C2 | 0.0310 (7) | 0.0268 (7) | 0.0324 (7) | 0.0032 (5) | 0.0071 (5) | 0.0033 (5) |
C3 | 0.0358 (7) | 0.0248 (7) | 0.0330 (7) | 0.0025 (6) | 0.0103 (6) | 0.0042 (5) |
C4 | 0.0380 (8) | 0.0259 (7) | 0.0298 (7) | 0.0062 (6) | 0.0101 (6) | 0.0074 (5) |
C5 | 0.0323 (7) | 0.0287 (7) | 0.0406 (8) | 0.0048 (6) | 0.0107 (6) | 0.0096 (6) |
C6 | 0.0326 (7) | 0.0279 (7) | 0.0339 (7) | 0.0036 (6) | 0.0069 (6) | 0.0082 (6) |
C7 | 0.0439 (9) | 0.0315 (8) | 0.0479 (9) | 0.0129 (7) | 0.0101 (7) | 0.0084 (7) |
C8 | 0.0393 (8) | 0.0319 (8) | 0.0453 (9) | 0.0024 (6) | 0.0102 (7) | 0.0093 (6) |
C9 | 0.0476 (10) | 0.0559 (11) | 0.0556 (11) | 0.0108 (9) | 0.0034 (8) | 0.0068 (9) |
C10 | 0.0643 (13) | 0.0805 (15) | 0.0504 (11) | 0.0058 (11) | −0.0047 (10) | 0.0078 (10) |
C11 | 0.0728 (14) | 0.0686 (14) | 0.0447 (11) | −0.0010 (11) | 0.0141 (10) | 0.0006 (9) |
C12 | 0.0713 (14) | 0.0698 (14) | 0.0608 (12) | 0.0204 (11) | 0.0308 (11) | 0.0066 (10) |
C13 | 0.0532 (11) | 0.0608 (12) | 0.0489 (10) | 0.0212 (9) | 0.0154 (8) | 0.0132 (9) |
C14 | 0.0412 (8) | 0.0342 (8) | 0.0311 (7) | 0.0082 (6) | 0.0088 (6) | 0.0052 (6) |
C15 | 0.0569 (11) | 0.0581 (11) | 0.0412 (9) | 0.0003 (9) | 0.0191 (8) | 0.0048 (8) |
C16 | 0.0796 (15) | 0.0891 (16) | 0.0400 (10) | 0.0082 (13) | 0.0283 (10) | 0.0025 (10) |
C17 | 0.0748 (14) | 0.0848 (16) | 0.0350 (10) | 0.0105 (12) | 0.0057 (9) | −0.0112 (10) |
C18 | 0.0590 (12) | 0.0728 (14) | 0.0472 (11) | −0.0076 (10) | −0.0005 (9) | −0.0099 (9) |
C19 | 0.0467 (9) | 0.0589 (11) | 0.0369 (9) | −0.0040 (8) | 0.0085 (7) | −0.0018 (8) |
O1—C6 | 1.1910 (18) | C8—C9 | 1.382 (3) |
O2—C6 | 1.3309 (18) | C9—C10 | 1.384 (3) |
O2—C7 | 1.4424 (18) | C9—H9 | 0.9400 |
O3—C4 | 1.2978 (18) | C10—C11 | 1.369 (3) |
O3—H3O | 0.8401 | C10—H10 | 0.9400 |
O4—C4 | 1.2338 (18) | C11—C12 | 1.371 (3) |
C1—C4 | 1.4701 (19) | C11—H11 | 0.9400 |
C1—C2 | 1.514 (2) | C12—C13 | 1.385 (3) |
C1—C3 | 1.5168 (19) | C12—H12 | 0.9400 |
C1—H1 | 0.9900 | C13—H13 | 0.9400 |
C2—C3 | 1.500 (2) | C14—C19 | 1.386 (2) |
C2—C5 | 1.5035 (19) | C14—C15 | 1.387 (2) |
C2—H2 | 0.9900 | C15—C16 | 1.387 (3) |
C3—C14 | 1.491 (2) | C15—H15 | 0.9400 |
C3—H3 | 0.9900 | C16—C17 | 1.369 (3) |
C5—C6 | 1.495 (2) | C16—H16 | 0.9400 |
C5—H5A | 0.9800 | C17—C18 | 1.364 (3) |
C5—H5B | 0.9800 | C17—H17 | 0.9400 |
C7—C8 | 1.503 (2) | C18—C19 | 1.390 (2) |
C7—H7A | 0.9800 | C18—H18 | 0.9400 |
C7—H7B | 0.9800 | C19—H19 | 0.9400 |
C8—C13 | 1.386 (2) | ||
C6—O2—C7 | 117.49 (12) | H7A—C7—H7B | 107.8 |
C4—O3—H3O | 110.5 | C13—C8—C9 | 118.80 (17) |
C4—C1—C2 | 117.76 (12) | C13—C8—C7 | 117.95 (15) |
C4—C1—C3 | 119.46 (12) | C9—C8—C7 | 123.20 (15) |
C2—C1—C3 | 59.35 (9) | C10—C9—C8 | 120.03 (18) |
C4—C1—H1 | 116.1 | C10—C9—H9 | 120.0 |
C2—C1—H1 | 116.1 | C8—C9—H9 | 120.0 |
C3—C1—H1 | 116.1 | C11—C10—C9 | 120.9 (2) |
C3—C2—C5 | 122.65 (12) | C11—C10—H10 | 119.6 |
C3—C2—C1 | 60.43 (9) | C9—C10—H10 | 119.6 |
C5—C2—C1 | 117.10 (12) | C10—C11—C12 | 119.57 (19) |
C3—C2—H2 | 115.2 | C10—C11—H11 | 120.2 |
C5—C2—H2 | 115.2 | C12—C11—H11 | 120.2 |
C1—C2—H2 | 115.2 | C11—C12—C13 | 120.13 (19) |
C14—C3—C2 | 123.86 (12) | C11—C12—H12 | 119.9 |
C14—C3—C1 | 122.54 (13) | C13—C12—H12 | 119.9 |
C2—C3—C1 | 60.22 (9) | C8—C13—C12 | 120.59 (18) |
C14—C3—H3 | 113.4 | C8—C13—H13 | 119.7 |
C2—C3—H3 | 113.4 | C12—C13—H13 | 119.7 |
C1—C3—H3 | 113.4 | C19—C14—C15 | 118.04 (15) |
O4—C4—O3 | 123.72 (13) | C19—C14—C3 | 124.23 (14) |
O4—C4—C1 | 122.19 (13) | C15—C14—C3 | 117.73 (15) |
O3—C4—C1 | 114.08 (13) | C14—C15—C16 | 120.75 (19) |
C6—C5—C2 | 113.23 (12) | C14—C15—H15 | 119.6 |
C6—C5—H5A | 108.9 | C16—C15—H15 | 119.6 |
C2—C5—H5A | 108.9 | C17—C16—C15 | 120.40 (19) |
C6—C5—H5B | 108.9 | C17—C16—H16 | 119.8 |
C2—C5—H5B | 108.9 | C15—C16—H16 | 119.8 |
H5A—C5—H5B | 107.7 | C18—C17—C16 | 119.61 (18) |
O1—C6—O2 | 123.53 (14) | C18—C17—H17 | 120.2 |
O1—C6—C5 | 125.52 (14) | C16—C17—H17 | 120.2 |
O2—C6—C5 | 110.94 (12) | C17—C18—C19 | 120.6 (2) |
O2—C7—C8 | 112.59 (13) | C17—C18—H18 | 119.7 |
O2—C7—H7A | 109.1 | C19—C18—H18 | 119.7 |
C8—C7—H7A | 109.1 | C14—C19—C18 | 120.60 (17) |
O2—C7—H7B | 109.1 | C14—C19—H19 | 119.7 |
C8—C7—H7B | 109.1 | C18—C19—H19 | 119.7 |
C4—C1—C2—C3 | −109.52 (14) | O2—C7—C8—C9 | −4.8 (2) |
C4—C1—C2—C5 | 136.49 (13) | C13—C8—C9—C10 | 0.0 (3) |
C3—C1—C2—C5 | −113.99 (14) | C7—C8—C9—C10 | −177.41 (18) |
C5—C2—C3—C14 | −6.3 (2) | C8—C9—C10—C11 | 0.8 (3) |
C1—C2—C3—C14 | −111.25 (16) | C9—C10—C11—C12 | −0.8 (4) |
C5—C2—C3—C1 | 104.97 (15) | C10—C11—C12—C13 | 0.0 (4) |
C4—C1—C3—C14 | −139.96 (14) | C9—C8—C13—C12 | −0.8 (3) |
C2—C1—C3—C14 | 113.35 (15) | C7—C8—C13—C12 | 176.76 (18) |
C4—C1—C3—C2 | 106.68 (15) | C11—C12—C13—C8 | 0.8 (3) |
C2—C1—C4—O4 | 44.4 (2) | C2—C3—C14—C19 | 58.9 (2) |
C3—C1—C4—O4 | −24.3 (2) | C1—C3—C14—C19 | −14.8 (2) |
C2—C1—C4—O3 | −134.54 (13) | C2—C3—C14—C15 | −120.33 (17) |
C3—C1—C4—O3 | 156.83 (13) | C1—C3—C14—C15 | 166.00 (15) |
C3—C2—C5—C6 | 85.53 (17) | C19—C14—C15—C16 | −0.1 (3) |
C1—C2—C5—C6 | 156.23 (12) | C3—C14—C15—C16 | 179.20 (18) |
C7—O2—C6—O1 | 1.3 (2) | C14—C15—C16—C17 | −0.5 (4) |
C7—O2—C6—C5 | −177.29 (13) | C15—C16—C17—C18 | 0.1 (4) |
C2—C5—C6—O1 | 15.3 (2) | C16—C17—C18—C19 | 0.8 (4) |
C2—C5—C6—O2 | −166.14 (12) | C15—C14—C19—C18 | 1.0 (3) |
C6—O2—C7—C8 | −98.97 (16) | C3—C14—C19—C18 | −178.22 (18) |
O2—C7—C8—C13 | 177.73 (15) | C17—C18—C19—C14 | −1.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···O4i | 0.84 | 1.78 | 2.6224 (16) | 176 |
C1—H1···O1ii | 0.99 | 2.36 | 3.249 (2) | 149 |
C5—H5B···O1ii | 0.98 | 2.53 | 3.219 (2) | 127 |
C7—H7A···O3iii | 0.98 | 2.55 | 3.368 (2) | 141 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x−1, y, z; (iii) x+1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C19H18O4 |
Mr | 310.33 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 223 |
a, b, c (Å) | 5.5550 (5), 8.9606 (8), 16.6586 (16) |
α, β, γ (°) | 101.698 (2), 98.907 (2), 92.186 (2) |
V (Å3) | 800.11 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.39 × 0.09 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5723, 3668, 2831 |
Rint | 0.015 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.149, 1.06 |
No. of reflections | 3668 |
No. of parameters | 211 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.25 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···O4i | 0.84 | 1.78 | 2.6224 (16) | 176 |
C1—H1···O1ii | 0.99 | 2.36 | 3.249 (2) | 149 |
C5—H5B···O1ii | 0.98 | 2.53 | 3.219 (2) | 127 |
C7—H7A···O3iii | 0.98 | 2.55 | 3.368 (2) | 141 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x−1, y, z; (iii) x+1, y−1, z. |
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The title compound (I) was synthesized in the course of an investigation of selective deprotections of cyclopropanes generated through the reaction of 1,2-dioxines and stabilized phosphorus ylides (Avery et al., 2000, 2001). The molecular structure (Fig. 1) shows the carboxylic acid functional group at the C1 atom to lie to the opposite side of the cyclopropane ring to the substituents at the C2 and C3 atoms. Centrosymmetrically related molecules are connected by the familiar {···HOC=O}2 synthon and these are connected into a double layer via C—H···O contacts (Table 1). The double layers thus formed stack along the c-direction, being separated by hydrophobic interactions (Fig. 2).