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For the title compound, C12H16N2O3, a potential anti-­amnesic agent, the conformations of the mol­ecule in the crystal structure and that of the energy-minimized free mol­ecule do not differ significantly. Inter­molecular N—H...O and C—H...O hydrogen bonds stabilize the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805043023/cv6623sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805043023/cv6623Isup2.hkl
Contains datablock I

CCDC reference: 298410

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.050
  • wR factor = 0.127
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT021_ALERT_1_C Ratio Unique / Expected Reflections too High ... 1.03 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.17 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C9
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 1 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 0 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: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003) and Qmol (Gans & Shalloway, 2001); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

2-[4-(Acetamido)phenoxy]-N,N-dimethylacetamide: top
Crystal data top
C12H16N2O3F(000) = 504
Mr = 236.27Dx = 1.314 Mg m3
Monoclinic, P21/cMelting point: 433 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.350 (6) ÅCell parameters from 913 reflections
b = 17.604 (9) Åθ = 2.8–26.6°
c = 8.197 (5) ŵ = 0.10 mm1
β = 97.549 (18)°T = 298 K
V = 1194.5 (13) Å3Block, colourless
Z = 40.4 × 0.2 × 0.2 mm
Data collection top
Bruker SMART CCD 1K
diffractometer
2563 independent reflections
Radiation source: fine-focus sealed tube1492 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.068
ω scansθmax = 26.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.913, Tmax = 0.998k = 022
14079 measured reflectionsl = 010
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.057P)2 + 0.178P]
where P = (Fo2 + 2Fc2)/3
2468 reflections(Δ/σ)max < 0.001
161 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
N10.3657 (2)0.38041 (9)0.3521 (2)0.0435 (5)
H10.453 (3)0.3669 (12)0.311 (3)0.056 (7)*
C10.3367 (2)0.45915 (11)0.3434 (2)0.0382 (5)
C20.2250 (2)0.49671 (11)0.4221 (2)0.0445 (5)
H20.15960.46930.48440.053*
C30.2084 (2)0.57483 (11)0.4100 (2)0.0455 (5)
H30.13120.59950.46280.055*
C40.3058 (2)0.61582 (10)0.3200 (2)0.0407 (5)
C50.4167 (3)0.57830 (11)0.2389 (3)0.0519 (6)
H50.48190.60560.17620.062*
C60.4313 (2)0.50113 (12)0.2504 (3)0.0485 (6)
H60.50620.47640.19460.058*
O10.30294 (18)0.69332 (7)0.29997 (18)0.0534 (4)
C70.1981 (2)0.73554 (10)0.3872 (3)0.0438 (5)
H7A0.22030.72500.50410.053*
H7B0.08650.72240.34970.053*
C80.2280 (2)0.81840 (11)0.3541 (2)0.0396 (5)
O20.34480 (18)0.83827 (8)0.28935 (19)0.0578 (5)
N20.12187 (19)0.86827 (9)0.3993 (2)0.0433 (4)
C90.0148 (3)0.84848 (12)0.4824 (3)0.0551 (6)
H9A0.01760.79440.49750.083*
H9B0.11280.86470.41720.083*
H9C0.00480.87320.58770.083*
C100.1417 (3)0.94843 (12)0.3675 (3)0.0584 (6)
H10A0.18910.97310.46670.088*
H10B0.03810.97060.33110.088*
H10C0.21090.95470.28380.088*
C110.2795 (3)0.32470 (12)0.4120 (3)0.0504 (6)
O30.1544 (2)0.33609 (9)0.4700 (2)0.0793 (6)
C120.3492 (3)0.24706 (11)0.3999 (3)0.0609 (7)
H12A0.36720.22450.50730.091*
H12B0.44990.25060.35580.091*
H12C0.27530.21620.32870.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0399 (10)0.0315 (10)0.0620 (12)0.0025 (8)0.0178 (9)0.0004 (8)
C10.0348 (11)0.0342 (11)0.0459 (12)0.0006 (8)0.0060 (9)0.0018 (9)
C20.0441 (12)0.0371 (12)0.0559 (13)0.0020 (9)0.0202 (10)0.0008 (10)
C30.0459 (12)0.0370 (12)0.0567 (13)0.0030 (9)0.0187 (10)0.0040 (10)
C40.0448 (12)0.0279 (11)0.0509 (12)0.0016 (9)0.0124 (10)0.0020 (9)
C50.0568 (14)0.0352 (13)0.0698 (15)0.0005 (10)0.0313 (11)0.0030 (11)
C60.0466 (13)0.0365 (12)0.0675 (14)0.0045 (9)0.0263 (11)0.0021 (11)
O10.0652 (10)0.0312 (8)0.0710 (10)0.0036 (7)0.0354 (8)0.0007 (7)
C70.0472 (12)0.0347 (12)0.0528 (13)0.0018 (9)0.0189 (10)0.0041 (9)
C80.0408 (11)0.0344 (11)0.0451 (12)0.0015 (9)0.0111 (9)0.0007 (9)
O20.0579 (10)0.0397 (9)0.0835 (11)0.0007 (7)0.0376 (9)0.0042 (7)
N20.0424 (10)0.0324 (9)0.0581 (11)0.0028 (7)0.0176 (8)0.0012 (8)
C90.0482 (13)0.0491 (14)0.0723 (15)0.0039 (10)0.0245 (12)0.0012 (11)
C100.0636 (15)0.0357 (13)0.0790 (16)0.0069 (11)0.0211 (13)0.0039 (11)
C110.0455 (12)0.0395 (12)0.0690 (15)0.0020 (10)0.0179 (11)0.0028 (11)
O30.0682 (11)0.0429 (9)0.1397 (16)0.0055 (8)0.0613 (12)0.0109 (9)
C120.0610 (14)0.0369 (13)0.0906 (18)0.0066 (11)0.0312 (13)0.0100 (12)
Geometric parameters (Å, º) top
N1—C111.347 (3)C7—H7B0.9700
N1—C11.407 (2)C8—O21.221 (2)
N1—H10.87 (2)C8—N21.334 (2)
C1—C21.371 (3)N2—C91.447 (3)
C1—C61.382 (3)N2—C101.448 (3)
C2—C31.385 (3)C9—H9A0.9600
C2—H20.9300C9—H9B0.9600
C3—C41.373 (3)C9—H9C0.9600
C3—H30.9300C10—H10A0.9600
C4—O11.374 (2)C10—H10B0.9600
C4—C51.377 (3)C10—H10C0.9600
C5—C61.366 (3)C11—O31.220 (2)
C5—H50.9300C11—C121.494 (3)
C6—H60.9300C12—H12A0.9600
O1—C71.413 (2)C12—H12B0.9600
C7—C81.510 (3)C12—H12C0.9600
C7—H7A0.9700
C11—N1—C1129.72 (18)O2—C8—N2121.98 (19)
C11—N1—H1116.9 (14)O2—C8—C7121.02 (17)
C1—N1—H1113.3 (14)N2—C8—C7117.00 (17)
C2—C1—C6118.36 (19)C8—N2—C9124.49 (17)
C2—C1—N1125.05 (18)C8—N2—C10119.72 (17)
C6—C1—N1116.58 (17)C9—N2—C10115.78 (16)
C1—C2—C3120.89 (19)N2—C9—H9A109.5
C1—C2—H2119.6N2—C9—H9B109.5
C3—C2—H2119.6H9A—C9—H9B109.5
C4—C3—C2119.96 (18)N2—C9—H9C109.5
C4—C3—H3120.0H9A—C9—H9C109.5
C2—C3—H3120.0H9B—C9—H9C109.5
C3—C4—O1125.70 (17)N2—C10—H10A109.5
C3—C4—C5119.38 (19)N2—C10—H10B109.5
O1—C4—C5114.91 (17)H10A—C10—H10B109.5
C6—C5—C4120.22 (19)N2—C10—H10C109.5
C6—C5—H5119.9H10A—C10—H10C109.5
C4—C5—H5119.9H10B—C10—H10C109.5
C5—C6—C1121.17 (19)O3—C11—N1123.3 (2)
C5—C6—H6119.4O3—C11—C12122.50 (19)
C1—C6—H6119.4N1—C11—C12114.24 (18)
C4—O1—C7117.68 (15)C11—C12—H12A109.5
O1—C7—C8106.79 (15)C11—C12—H12B109.5
O1—C7—H7A110.4H12A—C12—H12B109.5
C8—C7—H7A110.4C11—C12—H12C109.5
O1—C7—H7B110.4H12A—C12—H12C109.5
C8—C7—H7B110.4H12B—C12—H12C109.5
H7A—C7—H7B108.6
C11—N1—C1—C211.9 (3)C3—C4—O1—C74.2 (3)
C11—N1—C1—C6169.4 (2)C5—C4—O1—C7176.60 (18)
C6—C1—C2—C30.6 (3)C4—O1—C7—C8175.65 (16)
N1—C1—C2—C3178.08 (19)O1—C7—C8—O212.2 (3)
C1—C2—C3—C40.8 (3)O1—C7—C8—N2167.96 (17)
C2—C3—C4—O1179.14 (19)O2—C8—N2—C9177.4 (2)
C2—C3—C4—C51.7 (3)C7—C8—N2—C92.5 (3)
C3—C4—C5—C61.1 (3)O2—C8—N2—C101.6 (3)
O1—C4—C5—C6179.6 (2)C7—C8—N2—C10178.58 (18)
C4—C5—C6—C10.4 (3)C1—N1—C11—O30.6 (4)
C2—C1—C6—C51.2 (3)C1—N1—C11—C12180.0 (2)
N1—C1—C6—C5177.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O30.932.352.925 (3)120
N1—H1···O2i0.87 (2)2.04 (2)2.911 (3)178 (2)
C9—H9A···O3ii0.962.603.491 (3)155
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y+1, z+1.
 

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