Download citation
Download citation
link to html
The structure determination of the title compound, C17H18O3, shows an E conformation about the C=C bond. Molecules associate via O—H...O interactions leading to the formation of chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680100602X/ya6019sup1.cif
Contains datablocks general, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680100602X/ya6019Isup2.hkl
Contains datablock I

CCDC reference: 165656

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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


Amber Alert 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

Comment top

The title compound, (I), was one of the isomers prepared from the reaction between the ylide Ph3PC(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.

Experimental top

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).

Refinement top

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.

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The mMolecular structure and crystallographic numbering scheme for (I). Displacement ellipsoids are shown at the 50% probability level (Johnson, 1976).
(I) top
Crystal data top
C17H18O3F(000) = 576
Mr = 270.33Dx = 1.243 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.273 (2) ÅCell parameters from 25 reflections
b = 4.877 (2) Åθ = 12.2–14.9°
c = 31.976 (5) ŵ = 0.08 mm1
β = 92.76 (2)°T = 173 K
V = 1444.5 (7) Å3Block, pale yellow
Z = 40.40 × 0.31 × 0.16 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.041
Radiation source: Rotating anodeθmax = 27.5°, θmin = 3.2°
Graphite monochromatorh = 012
ω scansk = 06
3930 measured reflectionsl = 4141
3318 independent reflections3 standard reflections every 400 reflections
2254 reflections with I > 2σ(I) intensity decay: 0.3%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-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 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C17H18O3V = 1444.5 (7) Å3
Mr = 270.33Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.273 (2) ŵ = 0.08 mm1
b = 4.877 (2) ÅT = 173 K
c = 31.976 (5) Å0.40 × 0.31 × 0.16 mm
β = 92.76 (2)°
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.041
3930 measured reflections3 standard reflections every 400 reflections
3318 independent reflections intensity decay: 0.3%
2254 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 0.82Δρmax = 0.21 e Å3
3318 reflectionsΔρmin = 0.17 e Å3
182 parameters
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
xyzUiso*/Ueq
O2'0.29394 (11)0.0748 (2)0.40820 (3)0.0417 (3)
H2'0.38620.02710.41690.0591 (14)*
O110.43518 (11)0.0624 (3)0.44042 (4)0.0548 (4)
O120.22437 (10)0.2413 (2)0.46249 (3)0.0396 (3)
C10.30511 (15)0.0794 (3)0.43740 (5)0.0370 (3)
C1'0.11484 (14)0.0342 (3)0.35626 (4)0.0299 (3)
C20.22441 (15)0.0738 (3)0.40595 (4)0.0338 (3)
C2'0.25083 (15)0.0786 (3)0.37425 (4)0.0334 (3)
C30.08172 (14)0.0449 (3)0.40487 (4)0.0311 (3)
H30.03740.07290.42530.0472 (11)*
C3'0.34337 (15)0.2797 (3)0.35833 (5)0.0399 (4)
H3'0.43660.30730.37130.0472 (11)*
C40.01702 (14)0.1776 (3)0.37494 (4)0.0321 (3)
H4A0.04120.26930.35220.0591 (14)*
H4B0.07640.31870.38990.0591 (14)*
C4'0.30000 (16)0.4337 (3)0.32467 (5)0.0405 (4)
H4'0.36330.56810.31430.0472 (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)
H5'0.17930.68680.25900.0472 (11)*
C6'0.01601 (19)0.5138 (4)0.25008 (5)0.0468 (4)
H6'0.04440.61830.22600.0472 (11)*
C7'0.11039 (18)0.3175 (3)0.26604 (6)0.0464 (4)
H7'0.20310.29100.25270.0472 (11)*
C8'0.07032 (16)0.1650 (3)0.30042 (5)0.0382 (3)
H8'0.13640.03590.31090.0472 (11)*
C8A'0.06803 (14)0.1951 (3)0.32097 (4)0.0315 (3)
C130.29989 (18)0.3956 (4)0.49385 (5)0.0486 (4)
H13A0.35040.26890.51240.0591 (14)*
H13B0.37220.51950.48010.0591 (14)*
C140.1892 (2)0.5577 (4)0.51862 (6)0.0578 (5)
H14A0.23640.66410.54010.0709 (16)*
H14B0.14020.68260.49990.0709 (16)*
H14C0.11840.43290.53210.0709 (16)*
C210.31546 (18)0.2557 (4)0.37736 (6)0.0505 (4)
H21A0.25270.36740.36040.0709 (16)*
H21B0.37840.14230.35890.0709 (16)*
H21C0.37470.37580.39410.0709 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O2'0.0331 (5)0.0517 (7)0.0400 (6)0.0048 (5)0.0028 (4)0.0024 (5)
O110.0250 (5)0.0894 (10)0.0502 (7)0.0053 (6)0.0039 (5)0.0033 (7)
O120.0295 (5)0.0520 (7)0.0378 (5)0.0007 (5)0.0069 (4)0.0077 (5)
C10.0269 (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)
C20.0291 (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)
C30.0301 (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)
C40.0290 (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)
C130.0446 (9)0.0621 (11)0.0405 (8)0.0091 (8)0.0145 (7)0.0031 (8)
C140.0631 (11)0.0666 (12)0.0445 (9)0.0059 (10)0.0086 (8)0.0167 (9)
C210.0355 (8)0.0610 (11)0.0550 (10)0.0166 (8)0.0003 (7)0.0096 (9)
Geometric parameters (Å, º) top
O2'—C2'1.3624 (18)C3—C41.5024 (19)
O11—C11.2175 (18)C3'—C4'1.357 (2)
O12—C11.3303 (18)C4'—C4A'1.415 (2)
O12—C131.4593 (18)C4A'—C5'1.407 (2)
C1—C21.484 (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'—C41.5164 (19)C7'—C8'1.364 (2)
C2—C31.3327 (19)C8'—C8A'1.421 (2)
C2—C211.504 (2)C13—C141.493 (3)
C2'—C3'1.414 (2)
C1—O12—C13116.47 (12)C4'—C3'—C2'120.50 (14)
O11—C1—O12121.58 (15)C3—C4—C1'110.60 (11)
O11—C1—C2123.57 (14)C3'—C4'—C4A'120.88 (14)
O12—C1—C2114.84 (12)C5'—C4A'—C4'121.40 (14)
C2'—C1'—C8A'118.83 (13)C5'—C4A'—C8A'119.92 (14)
C2'—C1'—C4119.68 (13)C4'—C4A'—C8A'118.68 (14)
C8A'—C1'—C4121.47 (12)C6'—C5'—C4A'121.34 (15)
C3—C2—C1119.87 (13)C5'—C6'—C7'119.34 (16)
C3—C2—C21125.14 (14)C8'—C7'—C6'120.83 (16)
C1—C2—C21114.99 (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—C4127.39 (13)O12—C13—C14107.30 (13)

Experimental details

Crystal data
Chemical formulaC17H18O3
Mr270.33
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)9.273 (2), 4.877 (2), 31.976 (5)
β (°) 92.76 (2)
V3)1444.5 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.40 × 0.31 × 0.16
Data collection
DiffractometerRigaku AFC-7R
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3930, 3318, 2254
Rint0.041
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.135, 0.82
No. of reflections3318
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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.

 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds