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In the title compound, C12H15NO4, the mol­ecular packing is influenced by inter- and intra­molecular C—H...O hydrogen bonds. The two meth­oxy groups are almost in the same plane, and the acetamide group is somewhat twisted out of the benzene ring plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701625X/at2256sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680701625X/at2256Isup2.hkl
Contains datablock I

CCDC reference: 646706

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.056
  • wR factor = 0.095
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N-(2-Acetyl-3,5-dimethoxyphenyl)acetamide top
Crystal data top
C12H15NO4F(000) = 504
Mr = 237.25Dx = 1.317 Mg m3
Monoclinic, P21/cMelting point: 382 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.166 (3) ÅCell parameters from 2947 reflections
b = 17.156 (8) Åθ = 2.4–27.8°
c = 10.181 (5) ŵ = 0.10 mm1
β = 107.059 (6)°T = 291 K
V = 1196.6 (10) Å3Block, colourless
Z = 40.30 × 0.26 × 0.24 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2347 independent reflections
Radiation source: sealed tube1406 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
φ and ω scansθmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 86
Tmin = 0.97, Tmax = 0.98k = 2120
6381 measured reflectionsl = 1212
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)] = 0.056H-atom parameters constrained
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.03P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
2347 reflectionsΔρmax = 0.15 e Å3
159 parametersΔρmin = 0.13 e Å3
0 restraintsExtinction correction: SHELXL97 (Bruker, 2000), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0031 (7)
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
C10.2768 (3)0.27293 (11)0.68533 (18)0.0397 (4)
C20.2541 (3)0.19042 (10)0.69117 (19)0.0405 (4)
C30.1213 (3)0.16313 (11)0.7570 (2)0.0464 (5)
C40.0112 (3)0.21267 (12)0.8131 (2)0.0484 (5)
H40.07590.19280.85660.058*
C50.0343 (3)0.29190 (12)0.80264 (19)0.0459 (5)
C60.1656 (3)0.32162 (12)0.7399 (2)0.0487 (5)
H60.17920.37530.73430.058*
C70.3663 (3)0.13755 (12)0.6288 (2)0.0547 (6)
C80.3054 (3)0.05472 (11)0.5896 (2)0.0516 (5)
H8A0.35290.03890.51480.077*
H8B0.16550.05120.56210.077*
H8C0.35880.02120.66710.077*
C90.0373 (3)0.05275 (12)0.8220 (2)0.0560 (6)
H9A0.01970.07210.91330.084*
H9B0.02700.00310.82440.084*
H9C0.16390.06770.76420.084*
C100.1995 (3)0.32169 (14)0.9225 (2)0.0605 (6)
H10A0.30130.29130.86170.091*
H10B0.25540.36660.95290.091*
H10C0.13260.29061.00050.091*
C110.4463 (3)0.37830 (13)0.5954 (2)0.0531 (6)
C120.6021 (3)0.38694 (12)0.5251 (2)0.0550 (6)
H12A0.59970.43900.49020.082*
H12B0.57880.35050.45040.082*
H12C0.72740.37680.58950.082*
N10.4100 (2)0.30323 (9)0.62187 (17)0.0452 (4)
H10.47930.26910.59570.054*
O10.5164 (2)0.15906 (9)0.60292 (15)0.0558 (4)
O20.1097 (2)0.08475 (8)0.76861 (15)0.0523 (4)
O30.0655 (2)0.34612 (9)0.85233 (15)0.0585 (4)
O40.3645 (2)0.43319 (8)0.62599 (16)0.0575 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0374 (10)0.0417 (10)0.0425 (10)0.0032 (8)0.0155 (9)0.0064 (8)
C20.0409 (10)0.0344 (10)0.0476 (11)0.0008 (8)0.0151 (9)0.0045 (8)
C30.0453 (11)0.0410 (11)0.0553 (11)0.0025 (9)0.0185 (9)0.0110 (9)
C40.0483 (11)0.0552 (13)0.0474 (12)0.0037 (10)0.0231 (10)0.0099 (10)
C50.0494 (12)0.0506 (12)0.0410 (11)0.0018 (10)0.0185 (9)0.0005 (9)
C60.0608 (12)0.0424 (11)0.0506 (12)0.0006 (10)0.0284 (10)0.0020 (9)
C70.0629 (14)0.0398 (11)0.0638 (14)0.0138 (11)0.0224 (12)0.0114 (10)
C80.0606 (14)0.0447 (12)0.0544 (13)0.0114 (10)0.0246 (11)0.0033 (10)
C90.0641 (13)0.0521 (13)0.0548 (12)0.0133 (10)0.0220 (11)0.0208 (10)
C100.0575 (14)0.0631 (15)0.0626 (14)0.0068 (11)0.0200 (12)0.0007 (11)
C110.0571 (14)0.0428 (12)0.0672 (15)0.0046 (11)0.0305 (12)0.0116 (10)
C120.0626 (14)0.0510 (12)0.0613 (13)0.0001 (11)0.0338 (12)0.0153 (10)
N10.0516 (10)0.0370 (9)0.0537 (9)0.0027 (7)0.0261 (8)0.0049 (7)
O10.0682 (10)0.0580 (9)0.0490 (8)0.0058 (8)0.0297 (7)0.0044 (7)
O20.0463 (8)0.0407 (7)0.0685 (9)0.0018 (6)0.0148 (7)0.0241 (7)
O30.0680 (10)0.0539 (9)0.0590 (9)0.0033 (7)0.0269 (8)0.0045 (7)
O40.0633 (9)0.0430 (9)0.0726 (10)0.0050 (7)0.0298 (8)0.0190 (7)
Geometric parameters (Å, º) top
C1—C61.379 (3)C8—H8C0.9600
C1—N11.400 (2)C9—O21.429 (2)
C1—C21.428 (3)C9—H9A0.9600
C2—C31.396 (3)C9—H9B0.9600
C2—C71.474 (3)C9—H9C0.9600
C3—O21.355 (2)C10—O31.418 (3)
C3—C41.391 (3)C10—H10A0.9600
C4—C51.377 (3)C10—H10B0.9600
C4—H40.9300C10—H10C0.9600
C5—O31.358 (2)C11—O41.198 (3)
C5—C61.381 (3)C11—N11.356 (3)
C6—H60.9300C11—C121.500 (3)
C7—O11.236 (3)C12—H12A0.9600
C7—C81.505 (3)C12—H12B0.9600
C8—H8A0.9600C12—H12C0.9600
C8—H8B0.9600N1—H10.8600
C6—C1—N1120.91 (17)O2—C9—H9A109.5
C6—C1—C2119.82 (17)O2—C9—H9B109.5
N1—C1—C2119.26 (17)H9A—C9—H9B109.5
C3—C2—C1117.03 (17)O2—C9—H9C109.5
C3—C2—C7122.39 (17)H9A—C9—H9C109.5
C1—C2—C7120.58 (18)H9B—C9—H9C109.5
O2—C3—C4120.93 (18)O3—C10—H10A109.5
O2—C3—C2116.28 (17)O3—C10—H10B109.5
C4—C3—C2122.74 (18)H10A—C10—H10B109.5
C5—C4—C3118.43 (18)O3—C10—H10C109.5
C5—C4—H4120.8H10A—C10—H10C109.5
C3—C4—H4120.8H10B—C10—H10C109.5
O3—C5—C4123.98 (18)O4—C11—N1123.93 (19)
O3—C5—C6115.10 (17)O4—C11—C12122.40 (19)
C4—C5—C6120.91 (19)N1—C11—C12113.66 (19)
C1—C6—C5121.04 (18)C11—C12—H12A109.5
C1—C6—H6119.5C11—C12—H12B109.5
C5—C6—H6119.5H12A—C12—H12B109.5
O1—C7—C2121.8 (2)C11—C12—H12C109.5
O1—C7—C8115.37 (18)H12A—C12—H12C109.5
C2—C7—C8122.8 (2)H12B—C12—H12C109.5
C7—C8—H8A109.5C11—N1—C1129.83 (17)
C7—C8—H8B109.5C11—N1—H1115.1
H8A—C8—H8B109.5C1—N1—H1115.1
C7—C8—H8C109.5C3—O2—C9119.05 (17)
H8A—C8—H8C109.5C5—O3—C10119.58 (17)
H8B—C8—H8C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.861.92.612 (3)139
C6—H6···O40.932.202.830 (3)125
C12—H12A···O4i0.962.543.487 (3)169
Symmetry code: (i) x+1, y+1, z+1.
 

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