Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680100602X/ya6019sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680100602X/ya6019Isup2.hkl |
CCDC reference: 165656
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.037
- wR factor = 0.135
- Data-to-parameter ratio = 18.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level B:
ABSMU_01 Alert B The ratio of given/expected absorption coefficient lies outside the range 0.95 <> 1.05 Calculated value of mu = 0.084 Value of mu given = 0.080
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check
The title compound was prepared according to the literature procedure of Haselgrove et al. (1999). Crystals were obtained from the slow evaporation of a dichloromethane solution of the compound (m.p. 369–370 K).
The C-bound H atoms were placed in their geometrically calculated positions and included in the final refinement in the riding model approximation with an overall displacement parameter. The O—H atom was located from a difference map but was not refined.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The mMolecular structure and crystallographic numbering scheme for (I). Displacement ellipsoids are shown at the 50% probability level (Johnson, 1976). |
C17H18O3 | F(000) = 576 |
Mr = 270.33 | Dx = 1.243 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.273 (2) Å | Cell parameters from 25 reflections |
b = 4.877 (2) Å | θ = 12.2–14.9° |
c = 31.976 (5) Å | µ = 0.08 mm−1 |
β = 92.76 (2)° | T = 173 K |
V = 1444.5 (7) Å3 | Block, pale yellow |
Z = 4 | 0.40 × 0.31 × 0.16 mm |
Rigaku AFC-7R diffractometer | Rint = 0.041 |
Radiation source: Rotating anode | θmax = 27.5°, θmin = 3.2° |
Graphite monochromator | h = 0→12 |
ω scans | k = 0→6 |
3930 measured reflections | l = −41→41 |
3318 independent reflections | 3 standard reflections every 400 reflections |
2254 reflections with I > 2σ(I) | intensity decay: −0.3% |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 0.82 | w = 1/[σ2(Fo2) + (0.0918P)2 + 0.5393P] where P = (Fo2 + 2Fc2)/3 |
3318 reflections | (Δ/σ)max < 0.001 |
182 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C17H18O3 | V = 1444.5 (7) Å3 |
Mr = 270.33 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.273 (2) Å | µ = 0.08 mm−1 |
b = 4.877 (2) Å | T = 173 K |
c = 31.976 (5) Å | 0.40 × 0.31 × 0.16 mm |
β = 92.76 (2)° |
Rigaku AFC-7R diffractometer | Rint = 0.041 |
3930 measured reflections | 3 standard reflections every 400 reflections |
3318 independent reflections | intensity decay: −0.3% |
2254 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 0.82 | Δρmax = 0.21 e Å−3 |
3318 reflections | Δρmin = −0.17 e Å−3 |
182 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 | ||
O2' | 0.29394 (11) | −0.0748 (2) | 0.40820 (3) | 0.0417 (3) | |
H2' | 0.3862 | −0.0271 | 0.4169 | 0.0591 (14)* | |
O11 | −0.43518 (11) | 0.0624 (3) | 0.44042 (4) | 0.0548 (4) | |
O12 | −0.22437 (10) | 0.2413 (2) | 0.46249 (3) | 0.0396 (3) | |
C1 | −0.30511 (15) | 0.0794 (3) | 0.43740 (5) | 0.0370 (3) | |
C1' | 0.11484 (14) | 0.0342 (3) | 0.35626 (4) | 0.0299 (3) | |
C2 | −0.22441 (15) | −0.0738 (3) | 0.40595 (4) | 0.0338 (3) | |
C2' | 0.25083 (15) | 0.0786 (3) | 0.37425 (4) | 0.0334 (3) | |
C3 | −0.08172 (14) | −0.0449 (3) | 0.40487 (4) | 0.0311 (3) | |
H3 | −0.0374 | 0.0729 | 0.4253 | 0.0472 (11)* | |
C3' | 0.34337 (15) | 0.2797 (3) | 0.35833 (5) | 0.0399 (4) | |
H3' | 0.4366 | 0.3073 | 0.3713 | 0.0472 (11)* | |
C4 | 0.01702 (14) | −0.1776 (3) | 0.37494 (4) | 0.0321 (3) | |
H4A | −0.0412 | −0.2693 | 0.3522 | 0.0591 (14)* | |
H4B | 0.0764 | −0.3187 | 0.3899 | 0.0591 (14)* | |
C4' | 0.30000 (16) | 0.4337 (3) | 0.32467 (5) | 0.0405 (4) | |
H4' | 0.3633 | 0.5681 | 0.3143 | 0.0472 (11)* | |
C4A' | 0.16174 (15) | 0.3966 (3) | 0.30478 (5) | 0.0343 (3) | |
C5' | 0.11631 (18) | 0.5522 (3) | 0.26951 (5) | 0.0427 (4) | |
H5' | 0.1793 | 0.6868 | 0.2590 | 0.0472 (11)* | |
C6' | −0.01601 (19) | 0.5138 (4) | 0.25008 (5) | 0.0468 (4) | |
H6' | −0.0444 | 0.6183 | 0.2260 | 0.0472 (11)* | |
C7' | −0.11039 (18) | 0.3175 (3) | 0.26604 (6) | 0.0464 (4) | |
H7' | −0.2031 | 0.2910 | 0.2527 | 0.0472 (11)* | |
C8' | −0.07032 (16) | 0.1650 (3) | 0.30042 (5) | 0.0382 (3) | |
H8' | −0.1364 | 0.0359 | 0.3109 | 0.0472 (11)* | |
C8A' | 0.06803 (14) | 0.1951 (3) | 0.32097 (4) | 0.0315 (3) | |
C13 | −0.29989 (18) | 0.3956 (4) | 0.49385 (5) | 0.0486 (4) | |
H13A | −0.3504 | 0.2689 | 0.5124 | 0.0591 (14)* | |
H13B | −0.3722 | 0.5195 | 0.4801 | 0.0591 (14)* | |
C14 | −0.1892 (2) | 0.5577 (4) | 0.51862 (6) | 0.0578 (5) | |
H14A | −0.2364 | 0.6641 | 0.5401 | 0.0709 (16)* | |
H14B | −0.1402 | 0.6826 | 0.4999 | 0.0709 (16)* | |
H14C | −0.1184 | 0.4329 | 0.5321 | 0.0709 (16)* | |
C21 | −0.31546 (18) | −0.2557 (4) | 0.37736 (6) | 0.0505 (4) | |
H21A | −0.2527 | −0.3674 | 0.3604 | 0.0709 (16)* | |
H21B | −0.3784 | −0.1423 | 0.3589 | 0.0709 (16)* | |
H21C | −0.3747 | −0.3758 | 0.3941 | 0.0709 (16)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2' | 0.0331 (5) | 0.0517 (7) | 0.0400 (6) | −0.0048 (5) | −0.0028 (4) | −0.0024 (5) |
O11 | 0.0250 (5) | 0.0894 (10) | 0.0502 (7) | −0.0053 (6) | 0.0039 (5) | −0.0033 (7) |
O12 | 0.0295 (5) | 0.0520 (7) | 0.0378 (5) | −0.0007 (5) | 0.0069 (4) | −0.0077 (5) |
C1 | 0.0269 (6) | 0.0491 (9) | 0.0350 (7) | −0.0030 (6) | 0.0009 (5) | 0.0066 (7) |
C1' | 0.0275 (6) | 0.0284 (6) | 0.0344 (7) | −0.0023 (5) | 0.0065 (5) | −0.0082 (6) |
C2 | 0.0291 (6) | 0.0380 (7) | 0.0342 (7) | −0.0064 (6) | 0.0008 (5) | 0.0022 (6) |
C2' | 0.0297 (6) | 0.0359 (7) | 0.0349 (7) | −0.0022 (6) | 0.0059 (5) | −0.0100 (6) |
C3 | 0.0301 (6) | 0.0320 (7) | 0.0312 (6) | −0.0057 (5) | 0.0011 (5) | −0.0002 (6) |
C3' | 0.0282 (7) | 0.0469 (9) | 0.0450 (8) | −0.0089 (6) | 0.0060 (6) | −0.0124 (7) |
C4 | 0.0290 (6) | 0.0302 (7) | 0.0370 (7) | −0.0037 (5) | 0.0027 (5) | −0.0030 (6) |
C4' | 0.0348 (7) | 0.0392 (8) | 0.0490 (9) | −0.0098 (6) | 0.0164 (6) | −0.0082 (7) |
C4A' | 0.0351 (7) | 0.0312 (7) | 0.0377 (7) | −0.0014 (6) | 0.0133 (6) | −0.0077 (6) |
C5' | 0.0468 (9) | 0.0352 (8) | 0.0477 (9) | 0.0006 (7) | 0.0193 (7) | 0.0016 (7) |
C6' | 0.0504 (9) | 0.0421 (9) | 0.0482 (9) | 0.0079 (7) | 0.0067 (7) | 0.0083 (7) |
C7' | 0.0417 (8) | 0.0430 (9) | 0.0539 (10) | 0.0016 (7) | −0.0043 (7) | 0.0026 (8) |
C8' | 0.0337 (7) | 0.0328 (7) | 0.0481 (8) | −0.0031 (6) | 0.0016 (6) | −0.0016 (7) |
C8A' | 0.0313 (6) | 0.0275 (6) | 0.0364 (7) | −0.0007 (5) | 0.0082 (5) | −0.0078 (6) |
C13 | 0.0446 (9) | 0.0621 (11) | 0.0405 (8) | 0.0091 (8) | 0.0145 (7) | −0.0031 (8) |
C14 | 0.0631 (11) | 0.0666 (12) | 0.0445 (9) | 0.0059 (10) | 0.0086 (8) | −0.0167 (9) |
C21 | 0.0355 (8) | 0.0610 (11) | 0.0550 (10) | −0.0166 (8) | 0.0003 (7) | −0.0096 (9) |
O2'—C2' | 1.3624 (18) | C3—C4 | 1.5024 (19) |
O11—C1 | 1.2175 (18) | C3'—C4' | 1.357 (2) |
O12—C1 | 1.3303 (18) | C4'—C4A' | 1.415 (2) |
O12—C13 | 1.4593 (18) | C4A'—C5' | 1.407 (2) |
C1—C2 | 1.484 (2) | C4A'—C8A' | 1.425 (2) |
C1'—C2' | 1.3778 (19) | C5'—C6' | 1.361 (3) |
C1'—C8A' | 1.425 (2) | C6'—C7' | 1.409 (2) |
C1'—C4 | 1.5164 (19) | C7'—C8' | 1.364 (2) |
C2—C3 | 1.3327 (19) | C8'—C8A' | 1.421 (2) |
C2—C21 | 1.504 (2) | C13—C14 | 1.493 (3) |
C2'—C3' | 1.414 (2) | ||
C1—O12—C13 | 116.47 (12) | C4'—C3'—C2' | 120.50 (14) |
O11—C1—O12 | 121.58 (15) | C3—C4—C1' | 110.60 (11) |
O11—C1—C2 | 123.57 (14) | C3'—C4'—C4A' | 120.88 (14) |
O12—C1—C2 | 114.84 (12) | C5'—C4A'—C4' | 121.40 (14) |
C2'—C1'—C8A' | 118.83 (13) | C5'—C4A'—C8A' | 119.92 (14) |
C2'—C1'—C4 | 119.68 (13) | C4'—C4A'—C8A' | 118.68 (14) |
C8A'—C1'—C4 | 121.47 (12) | C6'—C5'—C4A' | 121.34 (15) |
C3—C2—C1 | 119.87 (13) | C5'—C6'—C7' | 119.34 (16) |
C3—C2—C21 | 125.14 (14) | C8'—C7'—C6' | 120.83 (16) |
C1—C2—C21 | 114.99 (12) | C7'—C8'—C8A' | 121.41 (14) |
O2'—C2'—C1' | 118.31 (13) | C8'—C8A'—C4A' | 117.14 (14) |
O2'—C2'—C3' | 120.53 (13) | C8'—C8A'—C1' | 122.90 (13) |
C1'—C2'—C3' | 121.16 (14) | C4A'—C8A'—C1' | 119.96 (13) |
C2—C3—C4 | 127.39 (13) | O12—C13—C14 | 107.30 (13) |
Experimental details
Crystal data | |
Chemical formula | C17H18O3 |
Mr | 270.33 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 9.273 (2), 4.877 (2), 31.976 (5) |
β (°) | 92.76 (2) |
V (Å3) | 1444.5 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.40 × 0.31 × 0.16 |
Data collection | |
Diffractometer | Rigaku AFC-7R diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3930, 3318, 2254 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.135, 0.82 |
No. of reflections | 3318 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.17 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1997), SIR97 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), SHELXL97.
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The title compound, (I), was one of the isomers prepared from the reaction between the ylide Ph3P═C(Me)C(O)OEt and 2-(2'-hydroxy-1'-naphthyl)acetaldehyde (Haselgrove et al., 1999). The structure analysis shows (I) to be the uncyclized (E)-butenoate (Fig. 1). The side chain, while not coplanar with the aromatic portion of the molecule, is effectively planar as seen in the sequence of torsion angles of -178.6 (1), 0.8 (1), 179.97 (8) and 179.10 (8)° for C4—C3—C2—C1, C3—C2—C1—O12, C2—C1—O12—C13 and C1—O12—C13—C14, respectively. The only two torsion angles in the molecule with `non-trivial' values are those describing the overall conformation of ethylbutenoate group relative to the naphthalene moiety, namely C2'—C1'—C4—C3 and C1'—C4—C3—C2, which are 94.6 (1) and 130.4 (1)°, respectively.
The major intermolecular interaction in the lattice occurs between the O—H2' and translationally related carbonyl O11 atoms, such that O—H2' is 0.92 Å, H2'···O11i is 1.84 Å, O2'···O11i is 2.751 (2) Å and the angle at H2' is 174°; symmetry code: (i) 1 + x, y, z. This association leads to the formation of chains along the a axis.