Methyl 2-(2-hydr­oxy-1,3-dioxoinden-2-yl)acrylate

In the title compound, C₁₃H₁₀O₅, the five-membered ring adopts an envelope conformation. The crystal structure is stabilized by inter­molecular C—H...O and O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.114
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.66 Ratio

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Methyl 2-(2-hydroxy-1,3-dioxoinden-2-yl)acrylate

Crystal data

C13H10O5	Z = 2
Mr = 246.21	F(000) = 256
Triclinic, P1	Dx = 1.413 Mg m^−3
a = 7.1194 (5) Å	Cu Kα radiation, λ = 1.54180 Å
b = 8.7236 (4) Å	Cell parameters from 25 reflections
c = 9.7519 (11) Å	θ = 5–20°
α = 83.838 (8)°	µ = 0.93 mm^−1
β = 88.921 (8)°	T = 293 K
γ = 74.015 (6)°	Block, colourless
V = 578.84 (8) Å^3	0.26 × 0.21 × 0.18 mm

Data collection

Fine-focus sealed tube diffractometer	Rint = 0.015
Radiation source: fine-focus sealed tube	θmax = 67.9°, θmin = 4.6°
Graphite monochromator	h = 0→8
ω/2θ scans	k = −10→10
2239 measured reflections	l = −11→11
2054 independent reflections	2 standard reflections every 60 min
1917 reflections with I > 2σ(I)	intensity decay: 4%

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)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0603P)^2 + 0.1803P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.022
2054 reflections	Δρmax = 0.28 e Å^−3
164 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.052 (3)

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
O1	0.23054 (17)	0.49660 (13)	0.50353 (11)	0.0503 (3)
O2	0.02397 (16)	0.27200 (13)	0.67980 (12)	0.0459 (3)
H2	−0.0583	0.3334	0.6273	0.069*
O3	0.29344 (19)	0.17790 (14)	0.92888 (11)	0.0541 (4)
O4	0.38264 (18)	0.52769 (16)	0.81921 (14)	0.0594 (4)
O5	0.1272 (2)	0.71715 (16)	0.88537 (16)	0.0673 (4)
C1	0.2782 (2)	0.38290 (17)	0.59118 (15)	0.0375 (4)
C2	0.1590 (2)	0.35257 (17)	0.71973 (15)	0.0362 (4)
C3	0.3123 (2)	0.22025 (17)	0.80899 (15)	0.0376 (4)
C3A	0.4766 (2)	0.15419 (17)	0.71833 (15)	0.0381 (4)
C4	0.6330 (2)	0.01820 (19)	0.74407 (18)	0.0461 (4)
H4	0.6512	−0.0417	0.8300	0.055*
C5	0.7603 (2)	−0.0247 (2)	0.6375 (2)	0.0531 (5)
H5	0.8647	−0.1166	0.6515	0.064*
C6	0.7363 (3)	0.0659 (2)	0.5101 (2)	0.0532 (5)
H6	0.8238	0.0328	0.4401	0.064*
C7	0.5849 (2)	0.2043 (2)	0.48497 (17)	0.0460 (4)
H7	0.5709	0.2666	0.4002	0.055*
C7A	0.4545 (2)	0.24673 (18)	0.59135 (15)	0.0382 (4)
C8	0.0664 (2)	0.49843 (17)	0.79210 (15)	0.0385 (4)
C9	0.2094 (2)	0.58099 (18)	0.83307 (16)	0.0431 (4)
C10	0.2577 (5)	0.7968 (3)	0.9401 (3)	0.0964 (9)
H10A	0.1828	0.8936	0.9751	0.145*
H10B	0.3415	0.8226	0.8682	0.145*
H10C	0.3357	0.7273	1.0132	0.145*
C11	−0.1205 (3)	0.5456 (2)	0.82124 (19)	0.0514 (4)
H11A	−0.1680	0.6344	0.8696	0.062*
H11B	−0.2052	0.4902	0.7935	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0581 (7)	0.0454 (7)	0.0432 (7)	−0.0126 (5)	−0.0099 (5)	0.0112 (5)
O2	0.0482 (6)	0.0383 (6)	0.0530 (7)	−0.0155 (5)	−0.0113 (5)	−0.0011 (5)
O3	0.0678 (8)	0.0486 (7)	0.0355 (7)	−0.0023 (6)	0.0011 (5)	0.0052 (5)
O4	0.0509 (7)	0.0627 (8)	0.0701 (9)	−0.0205 (6)	−0.0019 (6)	−0.0180 (6)
O5	0.0747 (9)	0.0474 (7)	0.0864 (10)	−0.0198 (6)	0.0059 (7)	−0.0292 (7)
C1	0.0440 (8)	0.0361 (7)	0.0332 (8)	−0.0128 (6)	−0.0090 (6)	−0.0007 (6)
C2	0.0402 (8)	0.0322 (7)	0.0358 (8)	−0.0098 (6)	−0.0049 (6)	−0.0017 (6)
C3	0.0465 (8)	0.0312 (7)	0.0339 (8)	−0.0094 (6)	−0.0045 (6)	−0.0005 (6)
C3A	0.0424 (8)	0.0354 (7)	0.0366 (8)	−0.0105 (6)	−0.0059 (6)	−0.0030 (6)
C4	0.0451 (9)	0.0403 (8)	0.0495 (9)	−0.0079 (7)	−0.0071 (7)	0.0011 (7)
C5	0.0404 (9)	0.0466 (9)	0.0678 (12)	−0.0045 (7)	0.0000 (8)	−0.0060 (8)
C6	0.0438 (9)	0.0576 (10)	0.0601 (11)	−0.0148 (8)	0.0103 (8)	−0.0141 (9)
C7	0.0494 (9)	0.0519 (9)	0.0403 (9)	−0.0206 (7)	0.0035 (7)	−0.0043 (7)
C7A	0.0420 (8)	0.0368 (8)	0.0368 (8)	−0.0124 (6)	−0.0041 (6)	−0.0037 (6)
C8	0.0445 (8)	0.0322 (7)	0.0360 (8)	−0.0069 (6)	−0.0039 (6)	0.0004 (6)
C9	0.0542 (10)	0.0372 (8)	0.0386 (8)	−0.0140 (7)	−0.0017 (7)	−0.0032 (6)
C10	0.121 (2)	0.0792 (16)	0.114 (2)	−0.0557 (16)	0.0068 (17)	−0.0475 (16)
C11	0.0485 (9)	0.0495 (9)	0.0537 (10)	−0.0081 (7)	0.0007 (7)	−0.0082 (8)

Geometric parameters (Å, º)

O1—C1	1.2137 (18)	C4—H4	0.9300
O2—C2	1.4194 (17)	C5—C6	1.386 (3)
O2—H2	0.8200	C5—H5	0.9300
O3—C3	1.2042 (19)	C6—C7	1.382 (3)
O4—C9	1.203 (2)	C6—H6	0.9300
O5—C9	1.323 (2)	C7—C7A	1.390 (2)
O5—C10	1.444 (3)	C7—H7	0.9300
C1—C7A	1.471 (2)	C8—C11	1.315 (2)
C1—C2	1.541 (2)	C8—C9	1.482 (2)
C2—C8	1.505 (2)	C10—H10A	0.9600
C2—C3	1.5517 (19)	C10—H10B	0.9600
C3—C3A	1.477 (2)	C10—H10C	0.9600
C3A—C4	1.389 (2)	C11—H11A	0.9300
C3A—C7A	1.390 (2)	C11—H11B	0.9300
C4—C5	1.379 (3)
C2—O2—H2	109.5	C7—C6—H6	119.3
C9—O5—C10	116.62 (18)	C5—C6—H6	119.3
O1—C1—C7A	126.51 (15)	C6—C7—C7A	117.36 (16)
O1—C1—C2	125.65 (14)	C6—C7—H7	121.3
C7A—C1—C2	107.79 (12)	C7A—C7—H7	121.3
O2—C2—C8	113.71 (12)	C7—C7A—C3A	121.25 (14)
O2—C2—C1	107.23 (11)	C7—C7A—C1	128.73 (14)
C8—C2—C1	115.07 (12)	C3A—C7A—C1	109.99 (14)
O2—C2—C3	103.76 (11)	C11—C8—C9	122.87 (15)
C8—C2—C3	113.91 (12)	C11—C8—C2	124.08 (15)
C1—C2—C3	101.89 (12)	C9—C8—C2	113.00 (13)
O3—C3—C3A	127.59 (14)	O4—C9—O5	124.16 (16)
O3—C3—C2	124.99 (14)	O4—C9—C8	122.48 (15)
C3A—C3—C2	107.36 (12)	O5—C9—C8	113.35 (15)
C4—C3A—C7A	120.91 (15)	O5—C10—H10A	109.5
C4—C3A—C3	128.95 (14)	O5—C10—H10B	109.5
C7A—C3A—C3	110.11 (13)	H10A—C10—H10B	109.5
C5—C4—C3A	117.58 (16)	O5—C10—H10C	109.5
C5—C4—H4	121.2	H10A—C10—H10C	109.5
C3A—C4—H4	121.2	H10B—C10—H10C	109.5
C4—C5—C6	121.49 (16)	C8—C11—H11A	120.0
C4—C5—H5	119.3	C8—C11—H11B	120.0
C6—C5—H5	119.3	H11A—C11—H11B	120.0
C7—C6—C5	121.35 (16)
O1—C1—C2—O2	85.58 (17)	C6—C7—C7A—C1	−177.51 (15)
C7A—C1—C2—O2	−92.16 (13)	C4—C3A—C7A—C7	1.6 (2)
O1—C1—C2—C8	−42.0 (2)	C3—C3A—C7A—C7	−176.48 (13)
C7A—C1—C2—C8	140.26 (12)	C4—C3A—C7A—C1	−179.99 (14)
O1—C1—C2—C3	−165.77 (14)	C3—C3A—C7A—C1	1.90 (17)
C7A—C1—C2—C3	16.49 (14)	O1—C1—C7A—C7	−11.7 (3)
O2—C2—C3—O3	−81.64 (18)	C2—C1—C7A—C7	166.05 (15)
C8—C2—C3—O3	42.5 (2)	O1—C1—C7A—C3A	170.11 (14)
C1—C2—C3—O3	167.07 (15)	C2—C1—C7A—C3A	−12.18 (16)
O2—C2—C3—C3A	95.96 (13)	O2—C2—C8—C11	2.4 (2)
C8—C2—C3—C3A	−139.88 (13)	C1—C2—C8—C11	126.64 (16)
C1—C2—C3—C3A	−15.34 (14)	C3—C2—C8—C11	−116.22 (17)
O3—C3—C3A—C4	8.6 (3)	O2—C2—C8—C9	179.98 (12)
C2—C3—C3A—C4	−168.88 (15)	C1—C2—C8—C9	−55.78 (16)
O3—C3—C3A—C7A	−173.46 (15)	C3—C2—C8—C9	61.36 (17)
C2—C3—C3A—C7A	9.03 (16)	C10—O5—C9—O4	−5.9 (3)
C7A—C3A—C4—C5	−2.5 (2)	C10—O5—C9—C8	174.18 (18)
C3—C3A—C4—C5	175.18 (15)	C11—C8—C9—O4	171.90 (16)
C3A—C4—C5—C6	1.3 (3)	C2—C8—C9—O4	−5.7 (2)
C4—C5—C6—C7	0.8 (3)	C11—C8—C9—O5	−8.2 (2)
C5—C6—C7—C7A	−1.7 (3)	C2—C8—C9—O5	174.20 (13)
C6—C7—C7A—C3A	0.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3^i	0.93	2.50	3.431 (2)	174
O2—H2···O1^ii	0.82	2.00	2.808 (2)	171

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