For the title compound, C
12H
16N
2O
3, 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
CCDC reference: 298410
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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
C12H16N2O3 | F(000) = 504 |
Mr = 236.27 | Dx = 1.314 Mg m−3 |
Monoclinic, P21/c | Melting point: 433 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 8.350 (6) Å | Cell parameters from 913 reflections |
b = 17.604 (9) Å | θ = 2.8–26.6° |
c = 8.197 (5) Å | µ = 0.10 mm−1 |
β = 97.549 (18)° | T = 298 K |
V = 1194.5 (13) Å3 | Block, colourless |
Z = 4 | 0.4 × 0.2 × 0.2 mm |
Data collection top
Bruker SMART CCD 1K diffractometer | 2563 independent reflections |
Radiation source: fine-focus sealed tube | 1492 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
ω scans | θmax = 26.5°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.913, Tmax = 0.998 | k = 0→22 |
14079 measured reflections | l = 0→10 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H 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 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
N1 | 0.3657 (2) | 0.38041 (9) | 0.3521 (2) | 0.0435 (5) | |
H1 | 0.453 (3) | 0.3669 (12) | 0.311 (3) | 0.056 (7)* | |
C1 | 0.3367 (2) | 0.45915 (11) | 0.3434 (2) | 0.0382 (5) | |
C2 | 0.2250 (2) | 0.49671 (11) | 0.4221 (2) | 0.0445 (5) | |
H2 | 0.1596 | 0.4693 | 0.4844 | 0.053* | |
C3 | 0.2084 (2) | 0.57483 (11) | 0.4100 (2) | 0.0455 (5) | |
H3 | 0.1312 | 0.5995 | 0.4628 | 0.055* | |
C4 | 0.3058 (2) | 0.61582 (10) | 0.3200 (2) | 0.0407 (5) | |
C5 | 0.4167 (3) | 0.57830 (11) | 0.2389 (3) | 0.0519 (6) | |
H5 | 0.4819 | 0.6056 | 0.1762 | 0.062* | |
C6 | 0.4313 (2) | 0.50113 (12) | 0.2504 (3) | 0.0485 (6) | |
H6 | 0.5062 | 0.4764 | 0.1946 | 0.058* | |
O1 | 0.30294 (18) | 0.69332 (7) | 0.29997 (18) | 0.0534 (4) | |
C7 | 0.1981 (2) | 0.73554 (10) | 0.3872 (3) | 0.0438 (5) | |
H7A | 0.2203 | 0.7250 | 0.5041 | 0.053* | |
H7B | 0.0865 | 0.7224 | 0.3497 | 0.053* | |
C8 | 0.2280 (2) | 0.81840 (11) | 0.3541 (2) | 0.0396 (5) | |
O2 | 0.34480 (18) | 0.83827 (8) | 0.28935 (19) | 0.0578 (5) | |
N2 | 0.12187 (19) | 0.86827 (9) | 0.3993 (2) | 0.0433 (4) | |
C9 | −0.0148 (3) | 0.84848 (12) | 0.4824 (3) | 0.0551 (6) | |
H9A | −0.0176 | 0.7944 | 0.4975 | 0.083* | |
H9B | −0.1128 | 0.8647 | 0.4172 | 0.083* | |
H9C | −0.0048 | 0.8732 | 0.5877 | 0.083* | |
C10 | 0.1417 (3) | 0.94843 (12) | 0.3675 (3) | 0.0584 (6) | |
H10A | 0.1891 | 0.9731 | 0.4667 | 0.088* | |
H10B | 0.0381 | 0.9706 | 0.3311 | 0.088* | |
H10C | 0.2109 | 0.9547 | 0.2838 | 0.088* | |
C11 | 0.2795 (3) | 0.32470 (12) | 0.4120 (3) | 0.0504 (6) | |
O3 | 0.1544 (2) | 0.33609 (9) | 0.4700 (2) | 0.0793 (6) | |
C12 | 0.3492 (3) | 0.24706 (11) | 0.3999 (3) | 0.0609 (7) | |
H12A | 0.3672 | 0.2245 | 0.5073 | 0.091* | |
H12B | 0.4499 | 0.2506 | 0.3558 | 0.091* | |
H12C | 0.2753 | 0.2162 | 0.3287 | 0.091* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0399 (10) | 0.0315 (10) | 0.0620 (12) | 0.0025 (8) | 0.0178 (9) | 0.0004 (8) |
C1 | 0.0348 (11) | 0.0342 (11) | 0.0459 (12) | 0.0006 (8) | 0.0060 (9) | −0.0018 (9) |
C2 | 0.0441 (12) | 0.0371 (12) | 0.0559 (13) | −0.0020 (9) | 0.0202 (10) | 0.0008 (10) |
C3 | 0.0459 (12) | 0.0370 (12) | 0.0567 (13) | 0.0030 (9) | 0.0187 (10) | −0.0040 (10) |
C4 | 0.0448 (12) | 0.0279 (11) | 0.0509 (12) | 0.0016 (9) | 0.0124 (10) | −0.0020 (9) |
C5 | 0.0568 (14) | 0.0352 (13) | 0.0698 (15) | −0.0005 (10) | 0.0313 (11) | 0.0030 (11) |
C6 | 0.0466 (13) | 0.0365 (12) | 0.0675 (14) | 0.0045 (9) | 0.0263 (11) | −0.0021 (11) |
O1 | 0.0652 (10) | 0.0312 (8) | 0.0710 (10) | 0.0036 (7) | 0.0354 (8) | −0.0007 (7) |
C7 | 0.0472 (12) | 0.0347 (12) | 0.0528 (13) | 0.0018 (9) | 0.0189 (10) | −0.0041 (9) |
C8 | 0.0408 (11) | 0.0344 (11) | 0.0451 (12) | 0.0015 (9) | 0.0111 (9) | −0.0007 (9) |
O2 | 0.0579 (10) | 0.0397 (9) | 0.0835 (11) | 0.0007 (7) | 0.0376 (9) | 0.0042 (7) |
N2 | 0.0424 (10) | 0.0324 (9) | 0.0581 (11) | 0.0028 (7) | 0.0176 (8) | 0.0012 (8) |
C9 | 0.0482 (13) | 0.0491 (14) | 0.0723 (15) | 0.0039 (10) | 0.0245 (12) | 0.0012 (11) |
C10 | 0.0636 (15) | 0.0357 (13) | 0.0790 (16) | 0.0069 (11) | 0.0211 (13) | 0.0039 (11) |
C11 | 0.0455 (12) | 0.0395 (12) | 0.0690 (15) | 0.0020 (10) | 0.0179 (11) | 0.0028 (11) |
O3 | 0.0682 (11) | 0.0429 (9) | 0.1397 (16) | 0.0055 (8) | 0.0613 (12) | 0.0109 (9) |
C12 | 0.0610 (14) | 0.0369 (13) | 0.0906 (18) | 0.0066 (11) | 0.0312 (13) | 0.0100 (12) |
Geometric parameters (Å, º) top
N1—C11 | 1.347 (3) | C7—H7B | 0.9700 |
N1—C1 | 1.407 (2) | C8—O2 | 1.221 (2) |
N1—H1 | 0.87 (2) | C8—N2 | 1.334 (2) |
C1—C2 | 1.371 (3) | N2—C9 | 1.447 (3) |
C1—C6 | 1.382 (3) | N2—C10 | 1.448 (3) |
C2—C3 | 1.385 (3) | C9—H9A | 0.9600 |
C2—H2 | 0.9300 | C9—H9B | 0.9600 |
C3—C4 | 1.373 (3) | C9—H9C | 0.9600 |
C3—H3 | 0.9300 | C10—H10A | 0.9600 |
C4—O1 | 1.374 (2) | C10—H10B | 0.9600 |
C4—C5 | 1.377 (3) | C10—H10C | 0.9600 |
C5—C6 | 1.366 (3) | C11—O3 | 1.220 (2) |
C5—H5 | 0.9300 | C11—C12 | 1.494 (3) |
C6—H6 | 0.9300 | C12—H12A | 0.9600 |
O1—C7 | 1.413 (2) | C12—H12B | 0.9600 |
C7—C8 | 1.510 (3) | C12—H12C | 0.9600 |
C7—H7A | 0.9700 | | |
| | | |
C11—N1—C1 | 129.72 (18) | O2—C8—N2 | 121.98 (19) |
C11—N1—H1 | 116.9 (14) | O2—C8—C7 | 121.02 (17) |
C1—N1—H1 | 113.3 (14) | N2—C8—C7 | 117.00 (17) |
C2—C1—C6 | 118.36 (19) | C8—N2—C9 | 124.49 (17) |
C2—C1—N1 | 125.05 (18) | C8—N2—C10 | 119.72 (17) |
C6—C1—N1 | 116.58 (17) | C9—N2—C10 | 115.78 (16) |
C1—C2—C3 | 120.89 (19) | N2—C9—H9A | 109.5 |
C1—C2—H2 | 119.6 | N2—C9—H9B | 109.5 |
C3—C2—H2 | 119.6 | H9A—C9—H9B | 109.5 |
C4—C3—C2 | 119.96 (18) | N2—C9—H9C | 109.5 |
C4—C3—H3 | 120.0 | H9A—C9—H9C | 109.5 |
C2—C3—H3 | 120.0 | H9B—C9—H9C | 109.5 |
C3—C4—O1 | 125.70 (17) | N2—C10—H10A | 109.5 |
C3—C4—C5 | 119.38 (19) | N2—C10—H10B | 109.5 |
O1—C4—C5 | 114.91 (17) | H10A—C10—H10B | 109.5 |
C6—C5—C4 | 120.22 (19) | N2—C10—H10C | 109.5 |
C6—C5—H5 | 119.9 | H10A—C10—H10C | 109.5 |
C4—C5—H5 | 119.9 | H10B—C10—H10C | 109.5 |
C5—C6—C1 | 121.17 (19) | O3—C11—N1 | 123.3 (2) |
C5—C6—H6 | 119.4 | O3—C11—C12 | 122.50 (19) |
C1—C6—H6 | 119.4 | N1—C11—C12 | 114.24 (18) |
C4—O1—C7 | 117.68 (15) | C11—C12—H12A | 109.5 |
O1—C7—C8 | 106.79 (15) | C11—C12—H12B | 109.5 |
O1—C7—H7A | 110.4 | H12A—C12—H12B | 109.5 |
C8—C7—H7A | 110.4 | C11—C12—H12C | 109.5 |
O1—C7—H7B | 110.4 | H12A—C12—H12C | 109.5 |
C8—C7—H7B | 110.4 | H12B—C12—H12C | 109.5 |
H7A—C7—H7B | 108.6 | | |
| | | |
C11—N1—C1—C2 | 11.9 (3) | C3—C4—O1—C7 | 4.2 (3) |
C11—N1—C1—C6 | −169.4 (2) | C5—C4—O1—C7 | −176.60 (18) |
C6—C1—C2—C3 | −0.6 (3) | C4—O1—C7—C8 | 175.65 (16) |
N1—C1—C2—C3 | 178.08 (19) | O1—C7—C8—O2 | −12.2 (3) |
C1—C2—C3—C4 | −0.8 (3) | O1—C7—C8—N2 | 167.96 (17) |
C2—C3—C4—O1 | −179.14 (19) | O2—C8—N2—C9 | −177.4 (2) |
C2—C3—C4—C5 | 1.7 (3) | C7—C8—N2—C9 | 2.5 (3) |
C3—C4—C5—C6 | −1.1 (3) | O2—C8—N2—C10 | 1.6 (3) |
O1—C4—C5—C6 | 179.6 (2) | C7—C8—N2—C10 | −178.58 (18) |
C4—C5—C6—C1 | −0.4 (3) | C1—N1—C11—O3 | 0.6 (4) |
C2—C1—C6—C5 | 1.2 (3) | C1—N1—C11—C12 | 180.0 (2) |
N1—C1—C6—C5 | −177.6 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O3 | 0.93 | 2.35 | 2.925 (3) | 120 |
N1—H1···O2i | 0.87 (2) | 2.04 (2) | 2.911 (3) | 178 (2) |
C9—H9A···O3ii | 0.96 | 2.60 | 3.491 (3) | 155 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, −y+1, −z+1. |