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The O atom of the distal carbonyl group in 1-(3,4-di­methoxy­phenyl)­propane-1,2-dione, C11H12O4, is displaced from the plane that is defined by the proximal C=O double bond and the aromatic entity of the mol­ecule. This arrangement gives rise to a stereogenic C-C axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804007755/fl6091sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804007755/fl6091Isup2.hkl
Contains datablock I

CCDC reference: 239136

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.134
  • Data-to-parameter ratio = 15.1

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 ....... ? PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C9 .. 5.12 su PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 ... 1.53 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis RED (Oxford Diffraction, 2001); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON2002 (Spek, 2002); software used to prepare material for publication: SHELXL97.

1-(3,4-dimethoxyphenyl)propane-1,2-dione top
Crystal data top
C11H12O4F(000) = 220
Mr = 208.21Dx = 1.333 Mg m3
Triclinic, P1Melting point: not measured K
a = 7.927 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.185 (2) ÅCell parameters from 1238 reflections
c = 10.018 (2) Åθ = 2.3–22.1°
α = 65.00 (2)°µ = 0.10 mm1
β = 72.01 (2)°T = 298 K
γ = 62.82 (2)°Prism, yellow
V = 518.6 (2) Å30.52 × 0.34 × 0.06 mm
Z = 2
Data collection top
Oxford Diffraction Xcalibur CCD
diffractometer
1102 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 26.4°, θmin = 4.3°
Detector resolution: Sapphire CCD detector pixels mm-1h = 99
Rotation method data acquisition using ω scansk = 1010
4883 measured reflectionsl = 1212
2054 independent 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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 0.84 w = 1/[σ2(Fo2) + (0.0801P)2]
where P = (Fo2 + 2Fc2)/3
2054 reflections(Δ/σ)max = 0.010
136 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.18 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
C10.3648 (3)1.1266 (3)0.3107 (2)0.0471 (5)
C20.3313 (3)1.3399 (3)0.2203 (2)0.0521 (6)
C30.2852 (4)1.4119 (4)0.0689 (3)0.0784 (8)
H3A0.16951.39760.07420.094*
H3B0.38831.33810.01100.094*
H3C0.26791.54680.02300.094*
C40.2565 (3)1.0729 (3)0.4595 (2)0.0407 (5)
C50.1324 (3)1.2075 (3)0.5290 (2)0.0480 (5)
H50.12141.33660.48380.058*
C60.0245 (3)1.1526 (3)0.6649 (2)0.0511 (6)
H60.05741.24420.71150.061*
C70.0378 (3)0.9625 (3)0.7319 (2)0.0451 (5)
C80.1632 (3)0.8237 (3)0.6619 (2)0.0430 (5)
C90.2711 (3)0.8791 (3)0.5290 (2)0.0436 (5)
H90.35570.78700.48350.052*
C100.2136 (3)1.0335 (4)0.9293 (3)0.0739 (7)
H10A0.30621.12320.86260.089*
H10B0.15931.10350.94870.089*
H10C0.27490.96681.02110.089*
C110.2866 (3)0.4928 (3)0.6726 (2)0.0634 (7)
H11A0.41660.47710.66490.076*
H11B0.25760.52930.57530.076*
H11C0.27080.37230.73470.076*
O10.4823 (2)1.0083 (2)0.25114 (16)0.0686 (5)
O20.3489 (2)1.4407 (2)0.27208 (18)0.0746 (5)
O30.0651 (2)0.8949 (2)0.86332 (15)0.0626 (5)
O40.1604 (2)0.64078 (19)0.73622 (15)0.0582 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0436 (12)0.0465 (11)0.0476 (12)0.0126 (10)0.0060 (10)0.0178 (10)
C20.0449 (13)0.0513 (13)0.0521 (13)0.0186 (10)0.0008 (10)0.0139 (11)
C30.098 (2)0.0688 (16)0.0591 (15)0.0383 (15)0.0159 (14)0.0019 (13)
C40.0409 (11)0.0358 (10)0.0444 (11)0.0108 (9)0.0102 (9)0.0139 (9)
C50.0496 (13)0.0384 (10)0.0548 (13)0.0144 (10)0.0056 (10)0.0183 (10)
C60.0519 (13)0.0438 (11)0.0565 (13)0.0111 (10)0.0001 (11)0.0289 (11)
C70.0443 (12)0.0472 (12)0.0405 (11)0.0137 (9)0.0049 (9)0.0165 (10)
C80.0471 (12)0.0357 (10)0.0417 (11)0.0111 (9)0.0089 (9)0.0120 (9)
C90.0422 (12)0.0395 (10)0.0444 (12)0.0057 (9)0.0067 (9)0.0200 (9)
C100.0673 (16)0.0789 (16)0.0644 (15)0.0232 (13)0.0176 (13)0.0378 (14)
C110.0787 (16)0.0373 (11)0.0654 (15)0.0163 (11)0.0081 (13)0.0171 (11)
O10.0708 (11)0.0564 (9)0.0574 (10)0.0141 (8)0.0084 (8)0.0235 (8)
O20.0878 (13)0.0578 (10)0.0826 (12)0.0322 (9)0.0140 (9)0.0208 (9)
O30.0659 (10)0.0565 (9)0.0525 (9)0.0211 (8)0.0113 (8)0.0227 (8)
O40.0716 (11)0.0393 (8)0.0507 (9)0.0173 (7)0.0013 (7)0.0144 (7)
Geometric parameters (Å, º) top
C1—O11.218 (2)C7—O31.356 (2)
C1—C41.467 (3)C7—C81.408 (3)
C1—C21.526 (3)C8—C91.360 (3)
C2—O21.217 (2)C8—O41.369 (2)
C2—C31.473 (3)C9—H90.9300
C3—H3A0.9600C10—O31.429 (2)
C3—H3B0.9600C10—H10A0.9600
C3—H3C0.9600C10—H10B0.9600
C4—C51.380 (2)C10—H10C0.9600
C4—C91.401 (3)C11—O41.423 (2)
C5—C61.379 (3)C11—H11A0.9600
C5—H50.9300C11—H11B0.9600
C6—C71.376 (3)C11—H11C0.9600
C6—H60.9300
O1—C1—C4123.4 (2)O3—C7—C8115.4 (2)
O1—C1—C2116.1 (2)C6—C7—C8119.80 (18)
C4—C1—C2120.5 (2)C9—C8—O4125.8 (2)
O2—C2—C3122.9 (2)C9—C8—C7119.45 (18)
O2—C2—C1120.1 (2)O4—C8—C7114.8 (2)
C3—C2—C1117.0 (2)C8—C9—C4121.0 (2)
C2—C3—H3A109.5C8—C9—H9119.5
C2—C3—H3B109.5C4—C9—H9119.5
H3A—C3—H3B109.5O3—C10—H10A109.5
C2—C3—H3C109.5O3—C10—H10B109.5
H3A—C3—H3C109.5H10A—C10—H10B109.5
H3B—C3—H3C109.5O3—C10—H10C109.5
C5—C4—C9118.95 (18)H10A—C10—H10C109.5
C5—C4—C1122.61 (17)H10B—C10—H10C109.5
C9—C4—C1118.31 (16)O4—C11—H11A109.5
C6—C5—C4120.65 (18)O4—C11—H11B109.5
C6—C5—H5119.7H11A—C11—H11B109.5
C4—C5—H5119.7O4—C11—H11C109.5
C7—C6—C5120.17 (18)H11A—C11—H11C109.5
C7—C6—H6119.9H11B—C11—H11C109.5
C5—C6—H6119.9C7—O3—C10118.0 (2)
O3—C7—C6124.7 (2)C8—O4—C11117.5 (2)
O1—C1—C2—O2125.0 (2)O3—C7—C8—C9179.5 (2)
C4—C1—C2—O256.1 (3)C6—C7—C8—C90.5 (3)
O1—C1—C2—C352.8 (3)O3—C7—C8—O40.9 (3)
C4—C1—C2—C3126.2 (2)C6—C7—C8—O4178.1 (2)
O1—C1—C4—C5176.0 (2)O4—C8—C9—C4177.18 (18)
C2—C1—C4—C55.1 (3)C7—C8—C9—C41.2 (3)
O1—C1—C4—C98.2 (3)C5—C4—C9—C80.9 (3)
C2—C1—C4—C9170.68 (19)C1—C4—C9—C8175.04 (18)
C9—C4—C5—C60.2 (3)C6—C7—O3—C107.5 (3)
C1—C4—C5—C6175.92 (19)C8—C7—O3—C10171.4 (2)
C4—C5—C6—C70.9 (3)C9—C8—O4—C112.7 (3)
C5—C6—C7—O3178.38 (19)C7—C8—O4—C11178.84 (17)
C5—C6—C7—C80.6 (3)
 

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