4-Benz­yloxy-1-oxa­spiro­[4.6]undec-3-en-2-one

The title compound, C₁₇H₂₀O₃, the cyclo­heptane ring adopts a slightly distorted chair conformation. The planar five-membered ring is inclined at 57.13 (11)° to the phenyl ring of the benz­yloxy substituent. In the crystal structure, C—H...O and C—H...π hydrogen bonds generate layers in the ac plane.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.159
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C5     --  C6      ..        8.0 s.u.

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.25 Report
PLAT193_ALERT_1_C Cell and Diffraction Temperatures Differ by ....          5 Degree
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.737 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         34 Report

Alert level G
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          45 %
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           4 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          3 Note
PLAT933_ALERT_2_G Number of OMIT records in Embedded RES .........         10 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           4 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 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

---

Computing details

Data collection: CrystalClear-SM Expert (Rigaku, 2015); cell refinement: CrystalClear-SM Expert (Rigaku, 2015); data reduction: CrystalClear-SM Expert (Rigaku, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXL2014 (Sheldrick, 2015b); software used to prepare material for publication: PLATON (Spek, 2009).

4-Benzyloxy-1-oxaspiro[4.6]undec-3-en-2-one

Crystal data

C17H20O3	F(000) = 584
Mr = 272.33	Dx = 1.220 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2yn	Cell parameters from 75 reflections
a = 13.1661 (9) Å	θ = 6.6–68.3°
b = 5.9457 (4) Å	µ = 0.66 mm^−1
c = 19.6730 (13) Å	T = 298 K
β = 105.774 (3)°	Plate, colorless
V = 1482.04 (17) Å^3	0.26 × 0.17 × 0.08 mm
Z = 4

Data collection

Rigaku Pilatus 200K diffractometer	2663 independent reflections
Confocal monochromator	1961 reflections with I > 2σ(I)
Detector resolution: 5.8140 pixels mm^-1	Rint = 0.028
profile data from ω–scans	θmax = 68.0°, θmin = 7.0°
Absorption correction: analytical (Alcock, 1974)	h = −15→14
Tmin = 0.653, Tmax = 1.000	k = −7→6
10788 measured reflections	l = −23→23

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.047	W = 1/[Σ^2(FO^2) + (0.0944P)^2 + 0.0383P] WHERE P = (FO^2 + 2FC^2)/3
wR(F^2) = 0.159	(Δ/σ)max < 0.001
S = 1.12	Δρmax = 0.43 e Å^−3
2663 reflections	Δρmin = −0.19 e Å^−3
182 parameters	Extinction correction: shelxl-2014/7 (Sheldrick 2015a, FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
0 restraints	Extinction coefficient: 0.0055 (12)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.65557 (10)	0.7811 (2)	0.39735 (6)	0.0587 (4)
O2	0.51051 (14)	0.9560 (3)	0.40696 (9)	0.0926 (7)
O3	0.75329 (9)	0.4593 (2)	0.55237 (6)	0.0586 (4)
C1	0.73395 (13)	0.6282 (3)	0.43863 (9)	0.0466 (5)
C2	0.58293 (15)	0.8307 (3)	0.43300 (11)	0.0616 (7)
C3	0.60803 (14)	0.7127 (3)	0.49933 (10)	0.0572 (6)
C4	0.69565 (13)	0.5954 (3)	0.50349 (9)	0.0483 (5)
C5	0.84009 (14)	0.7456 (4)	0.45714 (10)	0.0615 (7)
C6	0.8889 (2)	0.7882 (5)	0.39683 (17)	0.0958 (11)
C7	0.9329 (2)	0.5925 (6)	0.36911 (17)	0.1085 (13)
C8	0.8603 (3)	0.4293 (5)	0.32391 (18)	0.1036 (12)
C9	0.7490 (2)	0.4241 (5)	0.32610 (13)	0.0845 (9)
C10	0.72762 (17)	0.4081 (3)	0.39760 (11)	0.0616 (7)
C11	0.71428 (15)	0.4155 (4)	0.61342 (10)	0.0626 (7)
C12	0.79198 (13)	0.2632 (3)	0.66139 (9)	0.0481 (5)
C13	0.81346 (15)	0.0543 (3)	0.63809 (10)	0.0573 (6)
C14	0.88756 (17)	−0.0856 (3)	0.68052 (12)	0.0673 (7)
C15	0.94012 (16)	−0.0186 (4)	0.74684 (12)	0.0668 (7)
C16	0.91935 (16)	0.1878 (4)	0.77136 (10)	0.0647 (7)
C17	0.84535 (15)	0.3281 (3)	0.72885 (9)	0.0555 (6)
H3	0.57020	0.71750	0.53290	0.0690*
H5A	0.88920	0.65620	0.49250	0.0740*
H5B	0.83240	0.88920	0.47860	0.0740*
H6A	0.83550	0.85530	0.35820	0.1150*
H6B	0.94480	0.89810	0.41250	0.1150*
H7A	0.97630	0.51050	0.40920	0.1300*
H7B	0.97960	0.64850	0.34240	0.1300*
H8A	0.88950	0.28020	0.33610	0.1240*
H8B	0.86070	0.45740	0.27540	0.1240*
H9A	0.71510	0.29710	0.29810	0.1010*
H9B	0.71490	0.55910	0.30310	0.1010*
H10A	0.77770	0.30310	0.42630	0.0740*
H10B	0.65770	0.34520	0.39110	0.0740*
H11A	0.64540	0.34440	0.59890	0.0750*
H11B	0.70780	0.55500	0.63740	0.0750*
H13	0.77730	0.00710	0.59290	0.0690*
H14	0.90160	−0.22540	0.66390	0.0810*
H15	0.99020	−0.11260	0.77560	0.0800*
H16	0.95530	0.23310	0.81680	0.0780*
H17	0.83140	0.46740	0.74580	0.0670*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0626 (8)	0.0623 (8)	0.0523 (7)	0.0119 (6)	0.0175 (6)	0.0119 (6)
O2	0.0841 (11)	0.1050 (13)	0.0885 (11)	0.0474 (10)	0.0234 (9)	0.0288 (10)
O3	0.0541 (7)	0.0765 (9)	0.0513 (7)	0.0182 (6)	0.0248 (6)	0.0183 (6)
C1	0.0483 (9)	0.0480 (10)	0.0446 (9)	0.0035 (7)	0.0146 (7)	0.0037 (7)
C2	0.0574 (11)	0.0630 (12)	0.0641 (12)	0.0134 (10)	0.0159 (9)	0.0070 (10)
C3	0.0516 (10)	0.0673 (13)	0.0567 (10)	0.0096 (9)	0.0215 (8)	0.0037 (9)
C4	0.0460 (9)	0.0526 (10)	0.0478 (9)	0.0035 (7)	0.0154 (7)	0.0037 (8)
C5	0.0572 (11)	0.0668 (12)	0.0639 (11)	−0.0080 (9)	0.0223 (9)	−0.0029 (10)
C6	0.0947 (18)	0.0952 (19)	0.112 (2)	−0.0267 (15)	0.0528 (16)	0.0020 (16)
C7	0.0777 (16)	0.158 (3)	0.108 (2)	0.0046 (18)	0.0564 (16)	−0.013 (2)
C8	0.113 (2)	0.102 (2)	0.120 (2)	0.0209 (18)	0.0730 (19)	−0.0032 (18)
C9	0.0960 (17)	0.0951 (17)	0.0661 (14)	0.0017 (14)	0.0285 (12)	−0.0249 (12)
C10	0.0660 (12)	0.0567 (12)	0.0653 (12)	−0.0034 (9)	0.0233 (9)	−0.0069 (9)
C11	0.0586 (11)	0.0801 (14)	0.0582 (11)	0.0134 (10)	0.0316 (9)	0.0172 (10)
C12	0.0488 (9)	0.0545 (10)	0.0464 (9)	−0.0010 (8)	0.0223 (7)	0.0063 (8)
C13	0.0629 (11)	0.0596 (12)	0.0493 (10)	−0.0065 (9)	0.0152 (8)	−0.0085 (9)
C14	0.0763 (13)	0.0526 (11)	0.0777 (14)	0.0053 (10)	0.0291 (11)	0.0011 (10)
C15	0.0568 (11)	0.0761 (14)	0.0664 (13)	0.0054 (10)	0.0150 (10)	0.0205 (11)
C16	0.0640 (12)	0.0853 (15)	0.0430 (9)	−0.0158 (11)	0.0115 (8)	0.0021 (10)
C17	0.0721 (12)	0.0531 (10)	0.0494 (10)	−0.0067 (9)	0.0303 (9)	−0.0041 (8)

Geometric parameters (Å, º)

O1—C1	1.448 (2)	C16—C17	1.379 (3)
O1—C2	1.363 (2)	C3—H3	0.9300
O2—C2	1.209 (3)	C5—H5A	0.9700
O3—C4	1.326 (2)	C5—H5B	0.9700
O3—C11	1.452 (2)	C6—H6A	0.9700
C1—C4	1.507 (2)	C6—H6B	0.9700
C1—C5	1.515 (3)	C7—H7A	0.9700
C1—C10	1.528 (3)	C7—H7B	0.9700
C2—C3	1.439 (3)	C8—H8A	0.9700
C3—C4	1.331 (3)	C8—H8B	0.9700
C5—C6	1.516 (4)	C9—H9A	0.9700
C6—C7	1.469 (4)	C9—H9B	0.9700
C7—C8	1.478 (5)	C10—H10A	0.9700
C8—C9	1.478 (5)	C10—H10B	0.9700
C9—C10	1.511 (3)	C11—H11A	0.9700
C11—C12	1.494 (3)	C11—H11B	0.9700
C12—C13	1.380 (3)	C13—H13	0.9300
C12—C17	1.377 (2)	C14—H14	0.9300
C13—C14	1.378 (3)	C15—H15	0.9300
C14—C15	1.360 (3)	C16—H16	0.9300
C15—C16	1.373 (3)	C17—H17	0.9300
C1—O1—C2	109.88 (13)	C7—C6—H6A	108.00
C4—O3—C11	116.60 (14)	C7—C6—H6B	108.00
O1—C1—C4	101.81 (14)	H6A—C6—H6B	107.00
O1—C1—C5	108.41 (15)	C6—C7—H7A	108.00
O1—C1—C10	108.26 (14)	C6—C7—H7B	108.00
C4—C1—C5	110.81 (15)	C8—C7—H7A	108.00
C4—C1—C10	110.72 (15)	C8—C7—H7B	108.00
C5—C1—C10	115.84 (16)	H7A—C7—H7B	107.00
O1—C2—O2	119.88 (19)	C7—C8—H8A	108.00
O1—C2—C3	109.93 (16)	C7—C8—H8B	108.00
O2—C2—C3	130.2 (2)	C9—C8—H8A	108.00
C2—C3—C4	107.02 (17)	C9—C8—H8B	108.00
O3—C4—C1	115.83 (15)	H8A—C8—H8B	107.00
O3—C4—C3	132.82 (17)	C8—C9—H9A	108.00
C1—C4—C3	111.35 (16)	C8—C9—H9B	108.00
C1—C5—C6	116.63 (18)	C10—C9—H9A	108.00
C5—C6—C7	116.9 (3)	C10—C9—H9B	108.00
C6—C7—C8	119.2 (3)	H9A—C9—H9B	107.00
C7—C8—C9	118.7 (3)	C1—C10—H10A	108.00
C8—C9—C10	117.8 (2)	C1—C10—H10B	108.00
C1—C10—C9	116.15 (18)	C9—C10—H10A	108.00
O3—C11—C12	107.20 (15)	C9—C10—H10B	108.00
C11—C12—C13	120.19 (16)	H10A—C10—H10B	107.00
C11—C12—C17	121.41 (17)	O3—C11—H11A	110.00
C13—C12—C17	118.39 (17)	O3—C11—H11B	110.00
C12—C13—C14	121.18 (18)	C12—C11—H11A	110.00
C13—C14—C15	119.76 (19)	C12—C11—H11B	110.00
C14—C15—C16	120.1 (2)	H11A—C11—H11B	108.00
C15—C16—C17	120.20 (18)	C12—C13—H13	119.00
C12—C17—C16	120.41 (17)	C14—C13—H13	119.00
C2—C3—H3	126.00	C13—C14—H14	120.00
C4—C3—H3	127.00	C15—C14—H14	120.00
C1—C5—H5A	108.00	C14—C15—H15	120.00
C1—C5—H5B	108.00	C16—C15—H15	120.00
C6—C5—H5A	108.00	C15—C16—H16	120.00
C6—C5—H5B	108.00	C17—C16—H16	120.00
H5A—C5—H5B	107.00	C12—C17—H17	120.00
C5—C6—H6A	108.00	C16—C17—H17	120.00
C5—C6—H6B	108.00
C2—O1—C1—C4	0.28 (18)	O1—C2—C3—C4	0.6 (2)
C2—O1—C1—C5	−116.60 (16)	O2—C2—C3—C4	179.7 (2)
C2—O1—C1—C10	117.00 (16)	C2—C3—C4—O3	179.77 (19)
C1—O1—C2—O2	−179.77 (18)	C2—C3—C4—C1	−0.4 (2)
C1—O1—C2—C3	−0.6 (2)	C1—C5—C6—C7	−73.6 (3)
C11—O3—C4—C1	−176.58 (15)	C5—C6—C7—C8	75.0 (4)
C11—O3—C4—C3	3.2 (3)	C6—C7—C8—C9	−19.3 (4)
C4—O3—C11—C12	−179.01 (15)	C7—C8—C9—C10	−51.0 (4)
O1—C1—C4—O3	179.95 (15)	C8—C9—C10—C1	81.3 (3)
O1—C1—C4—C3	0.11 (19)	O3—C11—C12—C13	−60.0 (2)
C5—C1—C4—O3	−64.9 (2)	O3—C11—C12—C17	118.58 (19)
C5—C1—C4—C3	115.24 (18)	C11—C12—C13—C14	177.65 (19)
C10—C1—C4—O3	65.0 (2)	C17—C12—C13—C14	−1.0 (3)
C10—C1—C4—C3	−114.81 (18)	C11—C12—C17—C16	−177.78 (19)
O1—C1—C5—C6	−69.6 (2)	C13—C12—C17—C16	0.9 (3)
C4—C1—C5—C6	179.51 (19)	C12—C13—C14—C15	0.6 (3)
C10—C1—C5—C6	52.3 (3)	C13—C14—C15—C16	0.0 (3)
O1—C1—C10—C9	60.9 (2)	C14—C15—C16—C17	−0.1 (3)
C4—C1—C10—C9	171.67 (18)	C15—C16—C17—C12	−0.3 (3)
C5—C1—C10—C9	−61.1 (2)

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O1	0.97	2.56	2.987 (3)	106
C16—H16···O2^i	0.93	2.53	3.362 (3)	149
C7—H7B···Cg2^ii	0.97	2.80	3.750 (3)	165

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+2, −y+1, −z+1.