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In the title mol­ecule, C11H8O5, the non-H atoms of the coumarin unit are essentially coplanar; the meth­oxy and carboxyl­ate groups form dihedral angles of 6.5 (4) and 6.7 (4)°, respectively, with this group. In the crystal structure, weak inter­molecular C—H...O hydrogen bonds form chains of rings propagating in the [210] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807006241/lw2004sup1.cif
Contains datablocks global, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807006241/lw20043sup2.hkl
Contains datablock 3

CCDC reference: 640422

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.060
  • wR factor = 0.169
  • Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.794 0.998 Tmin(prime) and Tmax expected: 0.962 0.991 RR(prime) = 0.820 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT432_ALERT_2_C Short Inter X...Y Contact O3 .. C1 .. 2.98 Ang.
0 ALERT level A = In general: serious problem 0 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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 top

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.

7-methoxy-2-oxo-2H-chromene-3-carboxylic acid top
Crystal data top
C11H8O5F(000) = 456
Mr = 220.17Dx = 1.607 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4642 reflections
a = 5.1389 (5) Åθ = 3.1–25.1°
b = 8.8515 (10) ŵ = 0.13 mm1
c = 20.057 (2) ÅT = 150 K
β = 93.916 (6)°Needle, orange
V = 910.20 (16) Å30.30 × 0.10 × 0.07 mm
Z = 4
Data collection top
Bruker–Nonius KappaCCD
diffractometer
1591 independent reflections
Radiation source: fine-focus sealed tube871 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.080
Detector resolution: 9 pixels mm-1θmax = 25.1°, θmin = 3.1°
φ scans and ω scans with κ offsetsh = 66
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 910
Tmin = 0.794, Tmax = 0.998l = 2323
4642 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0808P)2]
where P = (Fo2 + 2Fc2)/3
1591 reflections(Δ/σ)max = 0.001
150 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.2619 (4)0.1322 (2)0.48998 (11)0.0332 (6)
O20.4059 (4)0.0820 (3)0.59329 (12)0.0394 (7)
O31.0339 (4)0.3722 (3)0.58492 (12)0.0397 (7)
O40.8184 (5)0.2178 (3)0.64796 (12)0.0439 (7)
O50.0826 (4)0.2309 (3)0.26752 (11)0.0400 (7)
C10.4372 (6)0.1564 (4)0.54327 (18)0.0315 (9)
C20.6430 (6)0.2654 (4)0.53550 (17)0.0291 (8)
C30.6483 (6)0.3457 (4)0.47818 (17)0.0306 (8)
H3A0.78210.41840.47370.037*
C40.4572 (6)0.3230 (4)0.42460 (16)0.0298 (8)
C50.4519 (6)0.4030 (4)0.36393 (18)0.0335 (9)
H5A0.57700.48000.35800.040*
C60.2692 (6)0.3709 (4)0.31364 (18)0.0344 (9)
H6A0.26580.42650.27310.041*
C70.0845 (6)0.2552 (4)0.32157 (17)0.0329 (9)
C80.0822 (6)0.1761 (4)0.38059 (18)0.0341 (9)
H8A0.04300.09910.38650.041*
C90.2699 (6)0.2129 (4)0.43134 (17)0.0302 (8)
C100.8483 (6)0.2900 (4)0.59059 (18)0.0332 (9)
C110.2633 (7)0.1066 (4)0.27053 (18)0.0399 (10)
H11A0.37150.10070.22840.060*
H11B0.37510.12270.30760.060*
H11C0.16600.01210.27760.060*
H4O0.668 (8)0.152 (5)0.643 (2)0.064 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0311 (13)0.0363 (13)0.0317 (15)0.0067 (11)0.0027 (11)0.0024 (11)
O20.0394 (14)0.0410 (15)0.0376 (15)0.0027 (12)0.0011 (12)0.0059 (12)
O30.0328 (14)0.0438 (15)0.0417 (16)0.0069 (12)0.0024 (11)0.0003 (12)
O40.0420 (15)0.0531 (17)0.0356 (17)0.0101 (14)0.0041 (12)0.0074 (13)
O50.0369 (14)0.0467 (16)0.0354 (16)0.0077 (12)0.0051 (11)0.0015 (12)
C10.0290 (19)0.032 (2)0.034 (2)0.0004 (16)0.0002 (16)0.0008 (17)
C20.0237 (17)0.0299 (19)0.034 (2)0.0032 (15)0.0030 (14)0.0021 (16)
C30.0268 (17)0.0296 (18)0.036 (2)0.0033 (15)0.0055 (16)0.0001 (17)
C40.0284 (18)0.0327 (19)0.029 (2)0.0002 (16)0.0035 (15)0.0008 (16)
C50.0301 (19)0.033 (2)0.038 (2)0.0020 (15)0.0081 (16)0.0006 (17)
C60.0328 (19)0.036 (2)0.035 (2)0.0021 (17)0.0034 (16)0.0024 (16)
C70.0279 (18)0.0353 (19)0.035 (2)0.0023 (17)0.0016 (16)0.0023 (17)
C80.0283 (18)0.038 (2)0.036 (2)0.0008 (16)0.0032 (16)0.0028 (17)
C90.0295 (19)0.0305 (19)0.031 (2)0.0036 (16)0.0048 (15)0.0013 (16)
C100.0278 (19)0.038 (2)0.034 (2)0.0001 (17)0.0005 (15)0.0009 (17)
C110.036 (2)0.046 (2)0.037 (2)0.0049 (18)0.0044 (17)0.0014 (18)
Geometric parameters (Å, º) top
O1—C11.367 (4)C4—C91.383 (5)
O1—C91.379 (4)C4—C51.406 (5)
O2—C11.220 (4)C5—C61.360 (5)
O3—C101.211 (4)C5—H5A0.9500
O4—C101.334 (4)C6—C71.413 (5)
O4—H4O0.97 (4)C6—H6A0.9500
O5—C71.353 (4)C7—C81.376 (5)
O5—C111.443 (4)C8—C91.392 (5)
C1—C21.448 (5)C8—H8A0.9500
C2—C31.354 (4)C11—H11A0.9800
C2—C101.491 (4)C11—H11B0.9800
C3—C41.420 (4)C11—H11C0.9800
C3—H3A0.9500
C1—O1—C9122.0 (2)C7—C6—H6A119.9
C10—O4—H4O110 (2)O5—C7—C8124.5 (3)
C7—O5—C11117.5 (3)O5—C7—C6114.8 (3)
O2—C1—O1116.2 (3)C8—C7—C6120.7 (3)
O2—C1—C2125.9 (3)C7—C8—C9117.6 (3)
O1—C1—C2117.9 (3)C7—C8—H8A121.2
C3—C2—C1119.9 (3)C9—C8—H8A121.2
C3—C2—C10119.9 (3)O1—C9—C4120.6 (3)
C1—C2—C10120.2 (3)O1—C9—C8116.3 (3)
C2—C3—C4121.0 (3)C4—C9—C8123.1 (3)
C2—C3—H3A119.5O3—C10—O4120.4 (3)
C4—C3—H3A119.5O3—C10—C2122.7 (3)
C9—C4—C5117.8 (3)O4—C10—C2116.9 (3)
C9—C4—C3118.4 (3)O5—C11—H11A109.5
C5—C4—C3123.7 (3)O5—C11—H11B109.5
C6—C5—C4120.6 (3)H11A—C11—H11B109.5
C6—C5—H5A119.7O5—C11—H11C109.5
C4—C5—H5A119.7H11A—C11—H11C109.5
C5—C6—C7120.2 (3)H11B—C11—H11C109.5
C5—C6—H6A119.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4O···O20.97 (4)1.74 (4)2.612 (3)149 (4)
C3—H3A···O3i0.952.423.284 (4)151
C5—H5A···O3i0.952.593.409 (4)145
C8—H8A···O2ii0.952.513.459 (4)174
Symmetry codes: (i) x+2, y+1, z+1; (ii) x, y, z+1.
 

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