Ethyl 2-acetonyl-3-(1H-isochromen-1-yl)acrylate

In the title compound, C₁₇H₁₈O₄, mol­ecules related by the 2₁ screw axis are linked by weak inter­molecular C—H...O hydrogen bonds, forming one-dimensional chains progagating along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.040
• wR factor = 0.099
• Data-to-parameter ratio = 8.8

checkCIF/PLATON results

No syntax errors found





Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       C16A

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.21 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.67 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Ethyl 2-acetonyl-3-(1H-isochromen-1-yl)acrylate

Crystal data

C17H18O4	F(000) = 608
Mr = 286.31	Dx = 1.235 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 17321 reflections
a = 9.6237 (7) Å	θ = 2.6–27.5°
b = 18.8830 (12) Å	µ = 0.09 mm^−1
c = 8.4729 (4) Å	T = 150 K
V = 1539.73 (17) Å^3	2.6, 27.5
Z = 4	0.45 × 0.22 × 0.16 mm

Data collection

Bruker–Nonius KappaCCD diffractometer	1857 independent reflections
Radiation source: fine-focus sealed tube	1567 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
φ scans and ω scans with κ offsets	h = −11→12
Absorption correction: multi-scan (SORTAV; Blessing 1995)	k = −20→24
Tmin = 0.882, Tmax = 0.986	l = −10→10
7737 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0434P)^2 + 0.2438P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
1857 reflections	Δρmax = 0.20 e Å^−3
211 parameters	Δρmin = −0.15 e Å^−3
3 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.070 (9)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.22103 (18)	0.67060 (8)	−0.1596 (2)	0.0515 (5)
O2	0.72362 (19)	0.65999 (11)	0.2194 (3)	0.0734 (7)
O3	0.5163 (2)	0.69790 (12)	0.3017 (3)	0.0682 (6)
O4	0.5694 (2)	0.49536 (9)	0.1604 (2)	0.0538 (5)
C1	0.1086 (3)	0.69576 (15)	−0.0767 (3)	0.0562 (7)
H1A	0.0770	0.7423	−0.0996	0.067*
C2	0.0416 (3)	0.65938 (14)	0.0330 (4)	0.0544 (7)
H2A	−0.0309	0.6811	0.0916	0.065*
C3	0.0790 (2)	0.58608 (13)	0.0637 (3)	0.0456 (6)
C4	−0.0049 (3)	0.53905 (16)	0.1480 (3)	0.0549 (7)
H4A	−0.0874	0.5557	0.1972	0.066*
C5	0.0317 (3)	0.46841 (16)	0.1602 (3)	0.0564 (7)
H5A	−0.0258	0.4368	0.2180	0.068*
C6	0.1516 (3)	0.44342 (14)	0.0886 (4)	0.0538 (6)
H6A	0.1756	0.3948	0.0967	0.065*
C7	0.2368 (2)	0.48968 (12)	0.0050 (3)	0.0441 (5)
H7A	0.3187	0.4726	−0.0449	0.053*
C8	0.2019 (2)	0.56074 (12)	−0.0054 (3)	0.0395 (5)
C9	0.2975 (2)	0.61428 (11)	−0.0811 (3)	0.0410 (5)
H9A	0.3572	0.5896	−0.1604	0.049*
C10	0.3892 (2)	0.64655 (11)	0.0437 (3)	0.0398 (5)
H10A	0.3477	0.6800	0.1128	0.048*
C11	0.5236 (2)	0.63228 (11)	0.0659 (3)	0.0400 (5)
C12	0.6098 (2)	0.58315 (11)	−0.0346 (3)	0.0422 (5)
H12A	0.7044	0.6031	−0.0459	0.051*
H12B	0.5681	0.5803	−0.1412	0.051*
C13	0.6203 (2)	0.50943 (11)	0.0337 (3)	0.0402 (5)
C14	0.6945 (3)	0.45530 (13)	−0.0636 (3)	0.0526 (6)
H14A	0.7019	0.4110	−0.0038	0.079*
H14B	0.7878	0.4726	−0.0895	0.079*
H14C	0.6425	0.4468	−0.1612	0.079*
C15	0.5995 (3)	0.66428 (13)	0.2008 (4)	0.0510 (6)
C16	0.5950 (6)	0.7384 (4)	0.4218 (7)	0.060 (2)	0.598 (10)
H16A	0.6481	0.7059	0.4909	0.072*	0.598 (10)
H16B	0.6609	0.7714	0.3704	0.072*	0.598 (10)
C17	0.4953 (8)	0.7761 (4)	0.5100 (8)	0.094 (3)	0.598 (10)
H17A	0.5423	0.8050	0.5899	0.141*	0.598 (10)
H17B	0.4324	0.7427	0.5619	0.141*	0.598 (10)
H17C	0.4420	0.8070	0.4394	0.141*	0.598 (10)
C16A	0.5572 (14)	0.7149 (6)	0.4663 (7)	0.125 (8)	0.402 (10)
H16C	0.4789	0.7106	0.5415	0.150*	0.402 (10)
H16D	0.6372	0.6865	0.5032	0.150*	0.402 (10)
C17A	0.5929 (14)	0.7858 (8)	0.4349 (16)	0.117 (5)	0.402 (10)
H17D	0.6261	0.8083	0.5321	0.176*	0.402 (10)
H17E	0.5111	0.8112	0.3957	0.176*	0.402 (10)
H17F	0.6666	0.7872	0.3550	0.176*	0.402 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0581 (11)	0.0507 (9)	0.0456 (9)	0.0108 (8)	−0.0073 (9)	0.0015 (8)
O2	0.0437 (11)	0.0828 (13)	0.0936 (16)	0.0035 (10)	−0.0195 (11)	−0.0247 (13)
O3	0.0574 (12)	0.0813 (14)	0.0660 (13)	0.0071 (10)	−0.0177 (10)	−0.0361 (11)
O3A	0.0574 (12)	0.0813 (14)	0.0660 (13)	0.0071 (10)	−0.0177 (10)	−0.0361 (11)
O4	0.0574 (10)	0.0595 (10)	0.0446 (10)	0.0131 (8)	0.0074 (8)	0.0117 (8)
C1	0.0548 (15)	0.0550 (14)	0.0588 (16)	0.0182 (12)	−0.0148 (14)	−0.0109 (13)
C2	0.0441 (13)	0.0617 (15)	0.0573 (16)	0.0133 (11)	−0.0066 (12)	−0.0182 (14)
C3	0.0342 (11)	0.0585 (13)	0.0441 (13)	0.0024 (10)	−0.0049 (10)	−0.0144 (11)
C4	0.0371 (12)	0.0792 (19)	0.0484 (14)	−0.0023 (12)	−0.0003 (11)	−0.0102 (14)
C5	0.0496 (15)	0.0701 (18)	0.0494 (15)	−0.0128 (12)	0.0033 (12)	0.0018 (13)
C6	0.0526 (14)	0.0511 (13)	0.0577 (15)	−0.0027 (11)	0.0002 (12)	0.0007 (12)
C7	0.0389 (11)	0.0481 (12)	0.0454 (13)	0.0007 (9)	−0.0028 (10)	−0.0029 (10)
C8	0.0344 (11)	0.0482 (12)	0.0359 (11)	0.0011 (9)	−0.0046 (9)	−0.0065 (9)
C9	0.0418 (12)	0.0414 (11)	0.0397 (12)	0.0052 (9)	−0.0033 (10)	−0.0022 (9)
C10	0.0411 (12)	0.0369 (10)	0.0414 (12)	−0.0002 (8)	0.0005 (10)	−0.0029 (9)
C11	0.0398 (12)	0.0392 (11)	0.0411 (12)	−0.0037 (9)	−0.0012 (10)	0.0016 (9)
C12	0.0384 (12)	0.0457 (12)	0.0427 (12)	0.0000 (9)	0.0037 (10)	0.0029 (10)
C13	0.0340 (10)	0.0460 (11)	0.0406 (12)	0.0000 (9)	−0.0051 (10)	−0.0007 (10)
C14	0.0545 (16)	0.0503 (13)	0.0530 (15)	0.0063 (11)	0.0009 (13)	−0.0053 (12)
C15	0.0474 (14)	0.0474 (13)	0.0581 (15)	0.0013 (11)	−0.0072 (12)	−0.0082 (12)
C16	0.068 (4)	0.042 (3)	0.071 (4)	−0.005 (3)	−0.030 (3)	−0.032 (3)
C17	0.094 (5)	0.112 (5)	0.076 (4)	0.035 (4)	−0.029 (4)	−0.053 (4)
C16A	0.067 (7)	0.053 (6)	0.26 (2)	−0.017 (5)	−0.036 (9)	0.000 (9)
C17A	0.106 (10)	0.171 (15)	0.075 (7)	0.015 (10)	0.033 (7)	0.027 (9)

Geometric parameters (Å, º)

C1—C2	1.323 (4)	C10—C11	1.335 (3)
C1—O1	1.375 (3)	C10—H10A	0.9500
C9—O1	1.454 (3)	C11—C15	1.484 (3)
O2—C15	1.208 (3)	C11—C12	1.508 (3)
O3—C15	1.332 (3)	C12—C13	1.511 (3)
O3—C16	1.481 (5)	C12—H12A	0.9900
O4—C13	1.209 (3)	C12—H12B	0.9900
C1—H1A	0.9500	C13—C14	1.495 (3)
C2—C3	1.454 (4)	C14—H14A	0.9800
C2—H2A	0.9500	C14—H14B	0.9800
C3—C4	1.397 (4)	C14—H14C	0.9800
C3—C8	1.403 (3)	C16—C17	1.409 (7)
C4—C5	1.383 (4)	C16—H16A	0.9900
C4—H4A	0.9500	C16—H16B	0.9900
C5—C6	1.387 (4)	C17—H17A	0.9800
C5—H5A	0.9500	C17—H17B	0.9800
C6—C7	1.392 (4)	C17—H17C	0.9800
C6—H6A	0.9500	C16A—C17A	1.408 (8)
C7—C8	1.386 (3)	C16A—H16C	0.9900
C7—H7A	0.9500	C16A—H16D	0.9900
C8—C9	1.510 (3)	C17A—H17D	0.9800
C9—C10	1.506 (3)	C17A—H17E	0.9800
C9—H9A	1.0000	C17A—H17F	0.9800
C1—O1—C9	114.6 (2)	C11—C12—H12A	109.0
C15—O3—C16	112.3 (3)	C13—C12—H12A	109.0
C2—C1—O1	124.3 (2)	C11—C12—H12B	109.0
C2—C1—H1A	117.9	C13—C12—H12B	109.0
O1—C1—H1A	117.9	H12A—C12—H12B	107.8
C1—C2—C3	119.9 (2)	O4—C13—C14	122.2 (2)
C1—C2—H2A	120.0	O4—C13—C12	121.0 (2)
C3—C2—H2A	120.0	C14—C13—C12	116.8 (2)
C4—C3—C8	118.9 (2)	C13—C14—H14A	109.5
C4—C3—C2	123.6 (2)	C13—C14—H14B	109.5
C8—C3—C2	117.3 (2)	H14A—C14—H14B	109.5
C5—C4—C3	120.2 (2)	C13—C14—H14C	109.5
C5—C4—H4A	119.9	H14A—C14—H14C	109.5
C3—C4—H4A	119.9	H14B—C14—H14C	109.5
C4—C5—C6	120.5 (2)	O2—C15—O3	122.8 (3)
C4—C5—H5A	119.8	O2—C15—C11	124.0 (3)
C6—C5—H5A	119.8	O3—C15—C11	113.1 (2)
C5—C6—C7	120.0 (2)	C17—C16—O3	106.1 (5)
C5—C6—H6A	120.0	C17—C16—H16A	110.5
C7—C6—H6A	120.0	O3—C16—H16A	110.5
C8—C7—C6	119.8 (2)	C17—C16—H16B	110.5
C8—C7—H7A	120.1	O3—C16—H16B	110.5
C6—C7—H7A	120.1	H16A—C16—H16B	108.7
C7—C8—C3	120.5 (2)	C16—C17—H17A	109.5
C7—C8—C9	121.83 (19)	C16—C17—H17B	109.5
C3—C8—C9	117.5 (2)	H17A—C17—H17B	109.5
O1—C9—C10	108.78 (17)	C16—C17—H17C	109.5
O1—C9—C8	112.08 (17)	H17A—C17—H17C	109.5
C10—C9—C8	109.26 (19)	H17B—C17—H17C	109.5
O1—C9—H9A	108.9	C17A—C16A—H16C	112.7
C10—C9—H9A	108.9	C17A—C16A—H16D	112.7
C8—C9—H9A	108.9	H16C—C16A—H16D	110.2
C11—C10—C9	125.8 (2)	C16A—C17A—H17D	109.5
C11—C10—H10A	117.1	C16A—C17A—H17E	109.5
C9—C10—H10A	117.1	H17D—C17A—H17E	109.5
C10—C11—C15	120.2 (2)	C16A—C17A—H17F	109.5
C10—C11—C12	125.3 (2)	H17D—C17A—H17F	109.5
C15—C11—C12	114.52 (19)	H17E—C17A—H17F	109.5
C11—C12—C13	112.76 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O4^i	1.00	2.32	3.275 (3)	160
C12—H12B···O4^i	0.99	2.57	3.442 (3)	147

Symmetry code: (i) −x+1, −y+1, z−1/2.