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The title compound, C11H6O4, is a synthetic isocoumarin and is essentially planar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032399/ww2041sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032399/ww2041Isup2.hkl
Contains datablock I

CCDC reference: 621531

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.096
  • Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT031_ALERT_4_B Refined Extinction Parameter within Range ...... 2.00 Sigma PLAT230_ALERT_2_B Hirshfeld Test Diff for O3 - C10 .. 7.21 su
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.850 1.000 Tmin(prime) and Tmax expected: 0.962 0.976 RR(prime) = 0.863 Please check that your absorption correction is appropriate. REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 24.99 From the CIF: _diffrn_reflns_theta_full 27.99 From the CIF: _reflns_number_total 1396 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1529 Completeness (_total/calc) 91.30% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.91 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
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 2 ALERT level B = Potentially serious problem 5 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 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1999 or 2000); cell refinement: SAINT (Bruker, 1999 or 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

3H-furo[3,4-c]isochromene-1,5-dione top
Crystal data top
C11H6O4Z = 2
Mr = 202.16F(000) = 208
Triclinic, P1Dx = 1.552 Mg m3
Hall symbol: -P 1Melting point: 131 K
a = 7.9892 (13) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.0899 (13) ÅCell parameters from 1966 reflections
c = 8.2075 (13) Åθ = 2.7–28.0°
α = 67.089 (3)°µ = 0.12 mm1
β = 83.871 (3)°T = 293 K
γ = 62.738 (3)°Block, pale yellow
V = 432.68 (12) Å30.32 × 0.24 × 0.20 mm
Data collection top
Bruker SMART CCD
diffractometer
1396 independent reflections
Radiation source: fine-focus sealed tube1105 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
ω and φ scansθmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 59
Tmin = 0.850, Tmax = 1.000k = 99
1966 measured reflectionsl = 89
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0511P)2 + 0.0519P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1396 reflectionsΔρmax = 0.13 e Å3
137 parametersΔρmin = 0.13 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.010 (5)
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
C10.0669 (2)0.5585 (3)0.1830 (2)0.0475 (4)
H1A0.00410.61730.10910.057*
C20.2553 (3)0.6331 (3)0.1358 (2)0.0523 (4)
H2A0.31150.74250.02950.063*
C30.3619 (2)0.5468 (3)0.2451 (2)0.0500 (4)
H3A0.48930.59930.21160.060*
C40.2822 (2)0.3843 (3)0.4029 (2)0.0441 (4)
H4A0.35490.32680.47510.053*
C50.0901 (2)0.3059 (2)0.4539 (2)0.0381 (4)
C60.0168 (2)0.3949 (2)0.3418 (2)0.0413 (4)
C70.2199 (2)0.3161 (3)0.3874 (2)0.0485 (4)
C80.1921 (2)0.0762 (3)0.6536 (2)0.0450 (4)
C90.0101 (2)0.1379 (2)0.6160 (2)0.0410 (4)
C100.0490 (3)0.0089 (3)0.7637 (2)0.0474 (4)
C110.2657 (3)0.0938 (3)0.8286 (3)0.0565 (5)
H11A0.36930.21220.81680.068*
H11B0.30780.05760.91030.068*
O10.32400 (19)0.3771 (2)0.2990 (2)0.0691 (4)
O20.30184 (15)0.15428 (19)0.55065 (16)0.0529 (3)
O30.20040 (18)0.0079 (2)0.78669 (17)0.0627 (4)
O40.10321 (17)0.12689 (18)0.88611 (15)0.0589 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0603 (10)0.0516 (10)0.0432 (9)0.0369 (8)0.0171 (7)0.0197 (8)
C20.0621 (11)0.0491 (10)0.0450 (9)0.0290 (9)0.0041 (8)0.0127 (8)
C30.0446 (9)0.0522 (10)0.0522 (10)0.0228 (8)0.0027 (7)0.0179 (8)
C40.0436 (9)0.0485 (9)0.0479 (9)0.0274 (7)0.0129 (7)0.0201 (8)
C50.0451 (9)0.0391 (8)0.0380 (8)0.0232 (7)0.0111 (6)0.0195 (7)
C60.0471 (9)0.0482 (9)0.0450 (9)0.0302 (7)0.0158 (7)0.0263 (8)
C70.0504 (9)0.0591 (10)0.0531 (10)0.0349 (8)0.0163 (8)0.0289 (9)
C80.0455 (9)0.0486 (9)0.0477 (9)0.0228 (7)0.0095 (7)0.0248 (8)
C90.0452 (9)0.0422 (9)0.0424 (9)0.0235 (7)0.0125 (7)0.0206 (7)
C100.0584 (10)0.0404 (9)0.0421 (9)0.0226 (8)0.0123 (8)0.0164 (7)
C110.0546 (10)0.0530 (10)0.0537 (10)0.0176 (8)0.0004 (8)0.0198 (8)
O10.0581 (8)0.0907 (11)0.0776 (9)0.0539 (8)0.0258 (7)0.0314 (8)
O20.0422 (6)0.0641 (8)0.0582 (7)0.0280 (6)0.0077 (5)0.0253 (6)
O30.0628 (8)0.0639 (8)0.0607 (8)0.0396 (7)0.0217 (6)0.0142 (6)
O40.0642 (8)0.0511 (8)0.0483 (7)0.0240 (6)0.0077 (6)0.0101 (6)
Geometric parameters (Å, º) top
C1—C21.375 (3)C7—O11.196 (2)
C1—C61.389 (2)C7—O21.405 (2)
C1—H1A0.9300C8—C91.330 (2)
C2—C31.382 (2)C8—O21.348 (2)
C2—H2A0.9300C8—C111.484 (3)
C3—C41.376 (2)C9—C101.458 (2)
C3—H3A0.9300C10—O31.207 (2)
C4—C51.404 (2)C10—O41.369 (2)
C4—H4A0.9300C11—O41.438 (2)
C5—C61.405 (2)C11—H11A0.9700
C5—C91.443 (2)C11—H11B0.9700
C6—C71.476 (2)
C2—C1—C6119.60 (15)O1—C7—C6126.40 (18)
C2—C1—H1A120.2O2—C7—C6117.88 (14)
C6—C1—H1A120.2C9—C8—O2126.12 (16)
C1—C2—C3120.55 (16)C9—C8—C11111.79 (15)
C1—C2—H2A119.7O2—C8—C11122.09 (15)
C3—C2—H2A119.7C8—C9—C5120.58 (15)
C4—C3—C2120.93 (16)C8—C9—C10106.99 (15)
C4—C3—H3A119.5C5—C9—C10132.42 (14)
C2—C3—H3A119.5O3—C10—O4121.26 (16)
C3—C4—C5119.49 (15)O3—C10—C9130.45 (17)
C3—C4—H4A120.3O4—C10—C9108.29 (14)
C5—C4—H4A120.3O4—C11—C8102.36 (14)
C4—C5—C6119.07 (15)O4—C11—H11A111.3
C4—C5—C9125.06 (14)C8—C11—H11A111.3
C6—C5—C9115.88 (14)O4—C11—H11B111.3
C1—C6—C5120.36 (15)C8—C11—H11B111.3
C1—C6—C7118.36 (15)H11A—C11—H11B109.2
C5—C6—C7121.28 (16)C8—O2—C7118.22 (13)
O1—C7—O2115.72 (15)C10—O4—C11110.55 (13)
C6—C1—C2—C30.1 (3)C11—C8—C9—C101.10 (19)
C1—C2—C3—C40.3 (3)C4—C5—C9—C8179.15 (15)
C2—C3—C4—C50.4 (2)C6—C5—C9—C80.6 (2)
C3—C4—C5—C60.3 (2)C4—C5—C9—C100.0 (3)
C3—C4—C5—C9179.36 (15)C6—C5—C9—C10179.72 (15)
C2—C1—C6—C50.1 (2)C8—C9—C10—O3179.29 (18)
C2—C1—C6—C7179.00 (14)C5—C9—C10—O31.5 (3)
C4—C5—C6—C10.2 (2)C8—C9—C10—O40.20 (17)
C9—C5—C6—C1179.52 (14)C5—C9—C10—O4179.05 (15)
C4—C5—C6—C7178.86 (14)C9—C8—C11—O41.52 (19)
C9—C5—C6—C71.4 (2)O2—C8—C11—O4178.89 (13)
C1—C6—C7—O11.4 (3)C9—C8—O2—C70.1 (2)
C5—C6—C7—O1177.69 (16)C11—C8—O2—C7179.61 (15)
C1—C6—C7—O2178.18 (13)O1—C7—O2—C8178.34 (14)
C5—C6—C7—O22.7 (2)C6—C7—O2—C82.0 (2)
O2—C8—C9—C51.3 (2)O3—C10—O4—C11179.66 (16)
C11—C8—C9—C5178.26 (14)C9—C10—O4—C110.79 (17)
O2—C8—C9—C10179.34 (15)C8—C11—O4—C101.35 (17)
 

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