3-Acet­yl-7-methoxy­coumarin

In the title mol­ecule, C₁₂H₁₀O₄, the lactone and benzene rings are coplanar, while the plane of the acet­yl substituent is rotated by 12.26 (9)° from the mol­ecular plane. The mol­ecules stack through π–π inter­actions along [100] and these stacks are laterally connected by C—H...O hydrogen bonds along the other two axial directions.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.118
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.61 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

   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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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


checkCIF publication errors

Alert level A
PUBL023_ALERT_1_A There is a mismatched ^ on line 103
              'De-Chun Zhang^'
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: CrystalClear (Rigaku, 1999; Pflugrath, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2000); 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: CrystalStructure.

3-acetyl-7-methoxy-2H-1-benzopyran-2-one

Crystal data

C12H10O4	Z = 2
Mr = 218.20	F(000) = 228
Triclinic, P1	Dx = 1.453 Mg m^−3
Hall symbol: -p 1	Melting point: 437 K
a = 7.1501 (6) Å	Mo Kα radiation, λ = 0.71070 Å
b = 8.0640 (8) Å	Cell parameters from 1600 reflections
c = 9.685 (1) Å	θ = 3.1–25.3°
α = 80.247 (13)°	µ = 0.11 mm^−1
β = 69.517 (10)°	T = 193 K
γ = 72.896 (11)°	Block, light yellow
V = 498.60 (9) Å^3	0.61 × 0.20 × 0.10 mm

Data collection

Rigaku Mercury diffractometer	1810 independent reflections
Radiation source: fine-focus sealed tube	1465 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 7.31 pixels mm^-1	θmax = 25.4°, θmin = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (Jacobson, 1998)	k = −9→9
Tmin = 0.936, Tmax = 0.989	l = −11→11
4889 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0649P)^2 + 0.0595P] where P = (Fo^2 + 2Fc^2)/3
1810 reflections	(Δ/σ)max < 0.001
148 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−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	0.68875 (15)	1.14036 (12)	0.39689 (10)	0.0304 (3)
O2	0.9504 (2)	0.53708 (14)	0.31940 (13)	0.0561 (4)
O3	0.55725 (17)	1.35242 (13)	0.86015 (11)	0.0396 (3)
O4	0.74037 (16)	1.05792 (13)	0.17913 (11)	0.0385 (3)
C1	0.7576 (2)	1.01039 (18)	0.29960 (15)	0.0283 (3)
C2	0.8383 (2)	0.83400 (17)	0.35612 (16)	0.0276 (3)
C3	0.8433 (2)	0.80464 (17)	0.49713 (15)	0.0285 (3)
H3	0.8966	0.6893	0.5325	0.034*
C4	0.7716 (2)	0.94054 (17)	0.59379 (15)	0.0263 (3)
C5	0.7725 (2)	0.91761 (18)	0.74105 (15)	0.0296 (3)
H5	0.8245	0.8047	0.7814	0.035*
C6	0.6992 (2)	1.05602 (18)	0.82680 (15)	0.0307 (4)
H6	0.6992	1.0386	0.9263	0.037*
C7	0.6240 (2)	1.22394 (18)	0.76750 (16)	0.0299 (3)
C8	0.6217 (2)	1.25148 (17)	0.62232 (15)	0.0295 (4)
H8	0.5712	1.3647	0.5816	0.035*
C9	0.6952 (2)	1.10880 (18)	0.53918 (14)	0.0261 (3)
C10	0.9169 (2)	0.68439 (18)	0.26165 (16)	0.0337 (4)
C11	0.9557 (3)	0.7126 (2)	0.09863 (17)	0.0417 (4)
H11A	1.0363	0.6035	0.0525	0.063*
H11B	1.0326	0.8018	0.0577	0.063*
H11C	0.8236	0.7510	0.0787	0.063*
C12	0.4877 (3)	1.52735 (19)	0.80305 (18)	0.0429 (4)
H12A	0.5990	1.5576	0.7178	0.064*
H12B	0.4486	1.6074	0.8800	0.064*
H12C	0.3679	1.5366	0.7724	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0364 (6)	0.0280 (5)	0.0253 (5)	−0.0019 (4)	−0.0138 (4)	−0.0003 (4)
O2	0.0903 (10)	0.0299 (6)	0.0497 (7)	−0.0016 (6)	−0.0352 (7)	−0.0036 (5)
O3	0.0521 (7)	0.0336 (6)	0.0339 (6)	−0.0035 (5)	−0.0189 (5)	−0.0069 (5)
O4	0.0483 (7)	0.0386 (6)	0.0274 (6)	−0.0045 (5)	−0.0177 (5)	0.0011 (4)
C1	0.0249 (7)	0.0337 (8)	0.0255 (7)	−0.0067 (6)	−0.0077 (6)	−0.0024 (6)
C2	0.0242 (7)	0.0302 (7)	0.0287 (7)	−0.0072 (6)	−0.0096 (6)	−0.0001 (6)
C3	0.0255 (7)	0.0270 (7)	0.0315 (8)	−0.0069 (6)	−0.0098 (6)	0.0033 (6)
C4	0.0225 (7)	0.0294 (7)	0.0271 (8)	−0.0082 (6)	−0.0083 (6)	0.0010 (6)
C5	0.0307 (8)	0.0292 (7)	0.0282 (7)	−0.0073 (6)	−0.0121 (6)	0.0047 (6)
C6	0.0328 (8)	0.0375 (8)	0.0234 (7)	−0.0106 (6)	−0.0117 (6)	0.0024 (6)
C7	0.0271 (8)	0.0346 (8)	0.0297 (8)	−0.0075 (6)	−0.0104 (6)	−0.0048 (6)
C8	0.0290 (8)	0.0271 (7)	0.0310 (8)	−0.0032 (6)	−0.0125 (6)	0.0010 (6)
C9	0.0226 (7)	0.0322 (7)	0.0239 (7)	−0.0072 (6)	−0.0094 (5)	0.0020 (6)
C10	0.0322 (8)	0.0330 (8)	0.0373 (9)	−0.0058 (6)	−0.0149 (6)	−0.0026 (7)
C11	0.0504 (10)	0.0399 (8)	0.0341 (9)	−0.0093 (7)	−0.0108 (7)	−0.0103 (7)
C12	0.0550 (10)	0.0311 (8)	0.0424 (9)	−0.0033 (7)	−0.0197 (8)	−0.0070 (7)

Geometric parameters (Å, º)

O1—C9	1.3729 (16)	C5—H5	0.9500
O1—C1	1.3911 (17)	C6—C7	1.406 (2)
O2—C10	1.2176 (18)	C6—H6	0.9500
O3—C7	1.3531 (17)	C7—C8	1.3911 (19)
O3—C12	1.4348 (17)	C8—C9	1.382 (2)
O4—C1	1.2019 (17)	C8—H8	0.9500
C1—C2	1.460 (2)	C10—C11	1.493 (2)
C2—C3	1.357 (2)	C11—H11A	0.9800
C2—C10	1.491 (2)	C11—H11B	0.9800
C3—C4	1.422 (2)	C11—H11C	0.9800
C3—H3	0.9500	C12—H12A	0.9800
C4—C9	1.394 (2)	C12—H12B	0.9800
C4—C5	1.4087 (19)	C12—H12C	0.9800
C5—C6	1.370 (2)
C9—O1—C1	123.06 (11)	C8—C7—C6	120.73 (13)
C7—O3—C12	117.84 (11)	C9—C8—C7	117.83 (13)
O4—C1—O1	115.36 (12)	C9—C8—H8	121.1
O4—C1—C2	128.03 (14)	C7—C8—H8	121.1
O1—C1—C2	116.60 (12)	O1—C9—C8	116.30 (12)
C3—C2—C1	119.70 (13)	O1—C9—C4	120.55 (13)
C3—C2—C10	118.98 (13)	C8—C9—C4	123.15 (13)
C1—C2—C10	121.32 (12)	O2—C10—C2	118.91 (13)
C2—C3—C4	122.28 (13)	O2—C10—C11	119.91 (14)
C2—C3—H3	118.9	C2—C10—C11	121.18 (13)
C4—C3—H3	118.9	C10—C11—H11A	109.5
C9—C4—C5	117.48 (13)	C10—C11—H11B	109.5
C9—C4—C3	117.80 (13)	H11A—C11—H11B	109.5
C5—C4—C3	124.72 (13)	C10—C11—H11C	109.5
C6—C5—C4	120.85 (13)	H11A—C11—H11C	109.5
C6—C5—H5	119.6	H11B—C11—H11C	109.5
C4—C5—H5	119.6	O3—C12—H12A	109.5
C5—C6—C7	119.96 (13)	O3—C12—H12B	109.5
C5—C6—H6	120.0	H12A—C12—H12B	109.5
C7—C6—H6	120.0	O3—C12—H12C	109.5
O3—C7—C8	123.66 (13)	H12A—C12—H12C	109.5
O3—C7—C6	115.61 (12)	H12B—C12—H12C	109.5
C9—O1—C1—O4	179.41 (11)	C5—C6—C7—C8	0.4 (2)
C9—O1—C1—C2	0.32 (19)	O3—C7—C8—C9	179.72 (12)
O4—C1—C2—C3	−179.12 (14)	C6—C7—C8—C9	0.1 (2)
O1—C1—C2—C3	−0.2 (2)	C1—O1—C9—C8	179.83 (11)
O4—C1—C2—C10	1.2 (2)	C1—O1—C9—C4	−0.5 (2)
O1—C1—C2—C10	−179.82 (11)	C7—C8—C9—O1	179.35 (11)
C1—C2—C3—C4	0.2 (2)	C7—C8—C9—C4	−0.3 (2)
C10—C2—C3—C4	179.87 (11)	C5—C4—C9—O1	−179.62 (11)
C2—C3—C4—C9	−0.4 (2)	C3—C4—C9—O1	0.5 (2)
C2—C3—C4—C5	179.77 (12)	C5—C4—C9—C8	0.0 (2)
C9—C4—C5—C6	0.5 (2)	C3—C4—C9—C8	−179.85 (12)
C3—C4—C5—C6	−179.65 (13)	C3—C2—C10—O2	12.4 (2)
C4—C5—C6—C7	−0.7 (2)	C1—C2—C10—O2	−167.91 (14)
C12—O3—C7—C8	−2.4 (2)	C3—C2—C10—C11	−167.29 (13)
C12—O3—C7—C6	177.23 (13)	C1—C2—C10—C11	12.4 (2)
C5—C6—C7—O3	−179.25 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···O3^i	0.98	2.58	3.4406 (19)	147
C3—H3···O2^ii	0.95	2.37	3.2726 (17)	158

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