5,7-Dimeth­oxy-2H-chromen-2-one

The mol­ecular structure of the title compound, C₁₁H₁₀O₄, contains two fused six-membered rings. All non-H atoms are constrained to be coplanar by symmetry, the mol­ecule lying in a mirror plane.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.032
• wR factor = 0.090
• Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       8.53
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C10     ..       3.00 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   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
   0 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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

5,7-Dimethoxy-2H-chromen-2-one

Crystal data

C11H10O4	Dx = 1.422 Mg m^−3
Mr = 206.19	Melting point = 421–423 K
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 25 reflections
a = 10.518 (3) Å	θ = 3.0–27.5°
b = 6.706 (2) Å	µ = 0.11 mm^−1
c = 13.652 (6) Å	T = 298 K
V = 962.9 (6) Å^3	Chunk, colourless
Z = 4	0.26 × 0.21 × 0.14 mm
F(000) = 432

Data collection

Enraf–Nonius CAD-4 diffractometer	704 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 25.2°, θmin = 3.0°
ω/2θ scans	h = −12→0
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = 0→8
Tmin = 0.928, Tmax = 0.979	l = −1→16
1021 measured reflections	3 standard reflections every 60 min
938 independent reflections	intensity decay: 0.3%

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)] = 0.032	Only H-atom coordinates refined
wR(F^2) = 0.090	w = 1/[σ^2(Fo^2) + (0.0424P)^2 + 0.1836P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
938 reflections	Δρmax = 0.19 e Å^−3
110 parameters	Δρmin = −0.12 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: 0.038 (6)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.77824 (12)	0.2500	0.50449 (10)	0.0460 (4)
O2	0.62281 (14)	0.2500	0.39770 (13)	0.0763 (7)
O3	1.21138 (13)	0.2500	0.41131 (10)	0.0529 (5)
O4	1.10359 (14)	0.2500	0.74683 (11)	0.0532 (5)
C1	1.0597 (2)	0.2500	0.65329 (16)	0.0411 (5)
C2	1.15577 (19)	0.2500	0.58222 (15)	0.0417 (5)
C3	1.12518 (19)	0.2500	0.48502 (15)	0.0386 (5)
C4	0.9553 (2)	0.2500	0.35510 (16)	0.0426 (5)
C5	0.8312 (2)	0.2500	0.33380 (17)	0.0492 (6)
C6	0.7368 (2)	0.2500	0.40872 (17)	0.0488 (6)
C7	0.9331 (2)	0.2500	0.62717 (15)	0.0414 (5)
C8	0.90584 (18)	0.2500	0.52798 (15)	0.0374 (5)
C9	0.99642 (17)	0.2500	0.45456 (15)	0.0366 (5)
C10	1.3428 (2)	0.2500	0.4386 (2)	0.0632 (8)
C11	1.0121 (3)	0.2500	0.82405 (19)	0.0620 (7)
H2	1.241 (3)	0.2500	0.606 (2)	0.074*
H4	1.018 (3)	0.2500	0.304 (2)	0.074*
H5	0.802 (2)	0.2500	0.268 (2)	0.074*
H7	0.866 (2)	0.2500	0.675 (2)	0.074*
H10A	1.3617 (16)	0.134 (3)	0.4793 (13)	0.074*
H10B	1.389 (2)	0.2500	0.378 (2)	0.074*
H11A	0.9542 (16)	0.131 (3)	0.8169 (13)	0.074*
H11B	1.063 (3)	0.2500	0.883 (2)	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0253 (8)	0.0620 (10)	0.0507 (9)	0.000	−0.0001 (6)	0.000
O2	0.0283 (9)	0.1245 (17)	0.0762 (12)	0.000	−0.0114 (8)	0.000
O3	0.0260 (7)	0.0894 (12)	0.0435 (9)	0.000	0.0044 (6)	0.000
O4	0.0468 (9)	0.0753 (11)	0.0374 (8)	0.000	−0.0038 (7)	0.000
C1	0.0400 (12)	0.0441 (12)	0.0392 (11)	0.000	−0.0020 (9)	0.000
C2	0.0279 (11)	0.0502 (13)	0.0469 (12)	0.000	−0.0028 (10)	0.000
C3	0.0293 (11)	0.0445 (12)	0.0421 (11)	0.000	0.0031 (9)	0.000
C4	0.0354 (12)	0.0502 (13)	0.0421 (12)	0.000	0.0019 (10)	0.000
C5	0.0419 (13)	0.0602 (15)	0.0456 (12)	0.000	−0.0078 (10)	0.000
C6	0.0323 (11)	0.0583 (14)	0.0558 (14)	0.000	−0.0074 (10)	0.000
C7	0.0345 (11)	0.0470 (13)	0.0426 (12)	0.000	0.0056 (9)	0.000
C8	0.0249 (10)	0.0404 (12)	0.0469 (12)	0.000	0.0005 (9)	0.000
C9	0.0292 (11)	0.0379 (11)	0.0425 (11)	0.000	−0.0012 (8)	0.000
C10	0.0282 (12)	0.109 (2)	0.0527 (15)	0.000	0.0041 (10)	0.000
C11	0.0597 (17)	0.087 (2)	0.0392 (13)	0.000	0.0024 (12)	0.000

Geometric parameters (Å, º)

O1—C6	1.378 (3)	C4—C5	1.338 (3)
O1—C8	1.380 (2)	C4—C9	1.425 (3)
O2—C6	1.208 (3)	C4—H4	0.96 (3)
O3—C3	1.354 (2)	C5—C6	1.426 (3)
O3—C10	1.432 (3)	C5—H5	0.95 (3)
O4—C1	1.358 (3)	C7—C8	1.384 (3)
O4—C11	1.427 (3)	C7—H7	0.96 (3)
C1—C7	1.379 (3)	C8—C9	1.383 (3)
C1—C2	1.401 (3)	C10—H10A	0.977 (18)
C2—C3	1.366 (3)	C10—H10B	0.96 (3)
C2—H2	0.95 (3)	C11—H11A	1.010 (18)
C3—C9	1.417 (3)	C11—H11B	0.97 (3)
C6—O1—C8	121.89 (16)	O2—C6—O1	115.6 (2)
C3—O3—C10	116.94 (17)	O2—C6—C5	127.0 (2)
C1—O4—C11	117.74 (18)	O1—C6—C5	117.39 (19)
O4—C1—C7	124.9 (2)	C1—C7—C8	116.9 (2)
O4—C1—C2	113.95 (18)	C1—C7—H7	122.6 (16)
C7—C1—C2	121.2 (2)	C8—C7—H7	120.5 (16)
C3—C2—C1	120.20 (19)	O1—C8—C9	120.10 (18)
C3—C2—H2	123.3 (17)	O1—C8—C7	115.39 (18)
C1—C2—H2	116.5 (17)	C9—C8—C7	124.51 (19)
O3—C3—C2	124.35 (19)	C8—C9—C3	116.48 (19)
O3—C3—C9	114.95 (18)	C8—C9—C4	118.80 (19)
C2—C3—C9	120.70 (19)	C3—C9—C4	124.72 (19)
C5—C4—C9	120.2 (2)	O3—C10—H10A	110.1 (11)
C5—C4—H4	121.1 (16)	O3—C10—H10B	105.1 (15)
C9—C4—H4	118.7 (16)	H10A—C10—H10B	112.9 (13)
C4—C5—C6	121.6 (2)	O4—C11—H11A	109.6 (10)
C4—C5—H5	121.2 (16)	O4—C11—H11B	104.3 (17)
C6—C5—H5	117.2 (16)	H11A—C11—H11B	114.3 (13)
C11—O4—C1—C7	0.0	C6—O1—C8—C9	0.0
C11—O4—C1—C2	180.0	C6—O1—C8—C7	180.0
O4—C1—C2—C3	180.0	C1—C7—C8—O1	180.0
C7—C1—C2—C3	0.0	C1—C7—C8—C9	0.0
C10—O3—C3—C2	0.0	O1—C8—C9—C3	180.0
C10—O3—C3—C9	180.0	C7—C8—C9—C3	0.0
C1—C2—C3—O3	180.0	O1—C8—C9—C4	0.0
C1—C2—C3—C9	0.0	C7—C8—C9—C4	180.0
C9—C4—C5—C6	0.0	O3—C3—C9—C8	180.0
C8—O1—C6—O2	180.0	C2—C3—C9—C8	0.0
C8—O1—C6—C5	0.0	O3—C3—C9—C4	0.0
C4—C5—C6—O2	180.0	C2—C3—C9—C4	180.0
C4—C5—C6—O1	0.0	C5—C4—C9—C8	0.0
O4—C1—C7—C8	180.0	C5—C4—C9—C3	180.0
C2—C1—C7—C8	0.0