The title compound, C
14H
15NO
2·H
2O, is a potential antiamnesic agent. One methyl group of the dimethyl-substituted N atom appears to be disordered over two sites. In the crystal structure, the water molecule is involved in intermolecular hydrogen bonds with two neighbouring water molecules, as well as with the O atom of the amide group. The water
water interactions form extended chains which run parallel to the
c axis. Intermolecular C—H
O and C—H
π interactions are also observed.
Supporting information
CCDC reference: 221679
Key indicators
- Single-crystal X-ray study
- T = 160 K
- Mean (C-C) = 0.003 Å
- H-atom completeness 89%
- R factor = 0.066
- wR factor = 0.213
- Data-to-parameter ratio = 16.5
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
FORMU_01 There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C14 H17 N1 O3
Atom count from the _atom_site data: C14 H15 N1 O3
CELLZ_01
From the CIF: _cell_formula_units_Z 8
From the CIF: _chemical_formula_sum C14 H17 N O3
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 112.00 112.00 0.00
H 136.00 120.00 16.00
N 8.00 8.00 0.00
O 24.00 24.00 0.00
Difference between formula and atom_site contents detected.
WARNING: H atoms missing from atom site list. Is this intentional?
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Version 1.07; Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
N,
N-dimethyl-2-(2-naphthyloxy)acetamide monohydrate
top
Crystal data top
C14H15NO2·H2O | F(000) = 1056 |
Mr = 247.29 | Dx = 1.300 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 3163 reflections |
a = 51.8464 (6) Å | θ = 2.0–27.5° |
b = 5.9134 (1) Å | µ = 0.09 mm−1 |
c = 8.3112 (1) Å | T = 160 K |
β = 97.4569 (5)° | Plate, colourless |
V = 2526.57 (6) Å3 | 0.25 × 0.23 × 0.05 mm |
Z = 8 | |
Data collection top
Nonius KappaCCD diffractometer | 2033 reflections with I > 2σ(I) |
Radiation source: Nonius FR591 sealed tube generator | Rint = 0.056 |
Horizontally mounted graphite crystal monochromator | θmax = 27.5°, θmin = 2.4° |
Detector resolution: 9 pixels mm-1 | h = 0→66 |
φ and ω scans with κ offsets | k = 0→7 |
26182 measured reflections | l = −10→10 |
2900 independent reflections | |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.213 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.1228P)2 + 1.8212P] where P = (Fo2 + 2Fc2)/3 |
2900 reflections | (Δ/σ)max < 0.001 |
176 parameters | Δρmax = 0.32 e Å−3 |
9 restraints | Δρmin = −0.51 e Å−3 |
Special details top
Experimental. Solvent used: acetone Cooling Device: Oxford Cryosystems Cryostream 700 Crystal
mount: glued on a glass fibre Mosaicity (°.): 0.478 (1) Frames collected: 1394
Seconds exposure per frame: 54 Degrees rotation per frame: 0.6
Crystal-Detector distance (mm): 39.0 |
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 | Occ. (<1) |
O1W | 0.01238 (5) | 0.3550 (6) | 0.4068 (3) | 0.1117 (10) | |
O11 | 0.11030 (3) | 0.3794 (2) | 0.34226 (17) | 0.0376 (4) | |
O13 | 0.06324 (3) | 0.4884 (4) | 0.3929 (2) | 0.0696 (7) | |
N14 | 0.06121 (3) | 0.8063 (4) | 0.2406 (2) | 0.0471 (5) | |
C1 | 0.15052 (4) | 0.4398 (3) | 0.2256 (2) | 0.0294 (4) | |
H1 | 0.1444 | 0.5782 | 0.1764 | 0.035* | |
C2 | 0.13482 (4) | 0.3167 (3) | 0.3140 (2) | 0.0314 (5) | |
C3 | 0.14362 (4) | 0.1083 (3) | 0.3847 (2) | 0.0346 (5) | |
H3 | 0.1327 | 0.0246 | 0.4461 | 0.042* | |
C4 | 0.16753 (4) | 0.0264 (3) | 0.3656 (2) | 0.0346 (5) | |
H4 | 0.1730 | −0.1152 | 0.4123 | 0.042* | |
C5 | 0.20995 (4) | 0.0742 (4) | 0.2571 (2) | 0.0368 (5) | |
H5 | 0.2160 | −0.0666 | 0.3023 | 0.044* | |
C6 | 0.22581 (4) | 0.2012 (4) | 0.1739 (3) | 0.0397 (5) | |
H6 | 0.2428 | 0.1484 | 0.1622 | 0.048* | |
C7 | 0.21721 (4) | 0.4089 (4) | 0.1058 (2) | 0.0365 (5) | |
H7 | 0.2284 | 0.4960 | 0.0481 | 0.044* | |
C8 | 0.19275 (4) | 0.4874 (3) | 0.1219 (2) | 0.0321 (5) | |
H8 | 0.1871 | 0.6284 | 0.0750 | 0.038* | |
C9 | 0.17580 (4) | 0.3604 (3) | 0.2079 (2) | 0.0286 (4) | |
C10 | 0.18455 (4) | 0.1495 (3) | 0.2768 (2) | 0.0306 (5) | |
C12 | 0.10027 (4) | 0.5807 (4) | 0.2638 (3) | 0.0367 (5) | |
H121 | 0.0999 | 0.5655 | 0.1449 | 0.044* | |
H122 | 0.1116 | 0.7105 | 0.3008 | 0.044* | |
C13 | 0.07297 (4) | 0.6209 (4) | 0.3045 (3) | 0.0444 (6) | |
C15 | 0.07305 (5) | 0.9577 (4) | 0.1321 (3) | 0.0522 (6) | |
H151 | 0.0902 | 1.0052 | 0.1842 | 0.078* | |
H152 | 0.0620 | 1.0910 | 0.1086 | 0.078* | |
H153 | 0.0749 | 0.8785 | 0.0306 | 0.078* | |
C16A | 0.03528 (12) | 0.884 (2) | 0.2714 (10) | 0.054 (2) | 0.67 (3) |
H161 | 0.0230 | 0.8702 | 0.1718 | 0.081* | 0.67 (3) |
H162 | 0.0363 | 1.0426 | 0.3061 | 0.081* | 0.67 (3) |
H163 | 0.0293 | 0.7911 | 0.3569 | 0.081* | 0.67 (3) |
C16B | 0.03275 (10) | 0.793 (5) | 0.238 (3) | 0.059 (4) | 0.33 (3) |
H164 | 0.0249 | 0.7330 | 0.1327 | 0.089* | 0.33 (3) |
H165 | 0.0258 | 0.9438 | 0.2540 | 0.089* | 0.33 (3) |
H166 | 0.0287 | 0.6920 | 0.3246 | 0.089* | 0.33 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1W | 0.0858 (18) | 0.153 (3) | 0.097 (2) | −0.0053 (17) | 0.0133 (15) | 0.0178 (18) |
O11 | 0.0360 (8) | 0.0416 (9) | 0.0363 (8) | −0.0037 (6) | 0.0087 (6) | 0.0023 (6) |
O13 | 0.0365 (9) | 0.1130 (17) | 0.0610 (12) | 0.0070 (9) | 0.0131 (8) | 0.0377 (12) |
N14 | 0.0368 (10) | 0.0627 (13) | 0.0410 (11) | 0.0096 (9) | 0.0020 (8) | −0.0052 (9) |
C1 | 0.0357 (10) | 0.0261 (9) | 0.0258 (9) | −0.0014 (8) | 0.0021 (8) | 0.0005 (7) |
C2 | 0.0357 (10) | 0.0319 (10) | 0.0263 (9) | −0.0045 (8) | 0.0027 (8) | −0.0040 (8) |
C3 | 0.0446 (12) | 0.0320 (11) | 0.0273 (10) | −0.0106 (9) | 0.0046 (8) | 0.0012 (8) |
C4 | 0.0506 (12) | 0.0262 (10) | 0.0256 (9) | −0.0026 (9) | −0.0006 (9) | 0.0005 (8) |
C5 | 0.0448 (12) | 0.0322 (11) | 0.0314 (10) | 0.0073 (9) | −0.0026 (9) | −0.0024 (8) |
C6 | 0.0363 (11) | 0.0457 (13) | 0.0366 (11) | 0.0069 (9) | 0.0026 (9) | −0.0055 (9) |
C7 | 0.0371 (11) | 0.0414 (12) | 0.0315 (10) | −0.0034 (9) | 0.0065 (8) | −0.0023 (9) |
C8 | 0.0396 (11) | 0.0297 (10) | 0.0265 (9) | 0.0005 (8) | 0.0029 (8) | 0.0014 (8) |
C9 | 0.0361 (10) | 0.0270 (10) | 0.0222 (9) | −0.0010 (8) | 0.0022 (7) | −0.0026 (7) |
C10 | 0.0411 (11) | 0.0269 (10) | 0.0228 (9) | −0.0004 (8) | 0.0002 (8) | −0.0034 (7) |
C12 | 0.0365 (11) | 0.0384 (12) | 0.0355 (11) | −0.0029 (9) | 0.0061 (9) | −0.0033 (9) |
C13 | 0.0336 (11) | 0.0680 (16) | 0.0310 (11) | −0.0012 (11) | 0.0015 (9) | −0.0023 (11) |
C15 | 0.0491 (14) | 0.0439 (14) | 0.0619 (16) | 0.0024 (11) | 0.0003 (12) | −0.0028 (12) |
C16A | 0.037 (2) | 0.074 (5) | 0.049 (3) | 0.011 (2) | 0.002 (2) | −0.008 (3) |
C16B | 0.046 (5) | 0.060 (10) | 0.071 (8) | 0.010 (4) | 0.003 (5) | −0.008 (6) |
Geometric parameters (Å, º) top
O11—C2 | 1.373 (2) | C6—H6 | 0.9500 |
O11—C12 | 1.423 (3) | C7—C8 | 1.373 (3) |
O13—C13 | 1.227 (3) | C7—H7 | 0.9500 |
N14—C13 | 1.331 (3) | C8—C9 | 1.418 (3) |
N14—C15 | 1.461 (3) | C8—H8 | 0.9500 |
N14—C16A | 1.474 (3) | C9—C10 | 1.422 (3) |
N14—C16B | 1.475 (4) | C12—C13 | 1.516 (3) |
C1—C2 | 1.374 (3) | C12—H121 | 0.9900 |
C1—C9 | 1.418 (3) | C12—H122 | 0.9900 |
C1—H1 | 0.9500 | C15—H151 | 0.9800 |
C2—C3 | 1.415 (3) | C15—H152 | 0.9800 |
C3—C4 | 1.359 (3) | C15—H153 | 0.9800 |
C3—H3 | 0.9500 | C16A—H161 | 0.9800 |
C4—C10 | 1.422 (3) | C16A—H162 | 0.9800 |
C4—H4 | 0.9500 | C16A—H163 | 0.9800 |
C5—C6 | 1.366 (3) | C16B—H164 | 0.9800 |
C5—C10 | 1.420 (3) | C16B—H165 | 0.9800 |
C5—H5 | 0.9500 | C16B—H166 | 0.9800 |
C6—C7 | 1.401 (3) | | |
| | | |
C2—O11—C12 | 116.03 (15) | C1—C9—C8 | 121.24 (17) |
C13—N14—C15 | 122.93 (19) | C1—C9—C10 | 119.98 (17) |
C13—N14—C16A | 124.6 (5) | C8—C9—C10 | 118.77 (18) |
C15—N14—C16A | 112.4 (5) | C5—C10—C9 | 118.75 (18) |
C13—N14—C16B | 111.5 (9) | C5—C10—C4 | 123.14 (18) |
C15—N14—C16B | 121.6 (7) | C9—C10—C4 | 118.09 (18) |
C2—C1—C9 | 119.99 (18) | O11—C12—C13 | 108.97 (17) |
C2—C1—H1 | 120.0 | O11—C12—H121 | 109.9 |
C9—C1—H1 | 120.0 | C13—C12—H121 | 109.9 |
O11—C2—C1 | 125.04 (18) | O11—C12—H122 | 109.9 |
O11—C2—C3 | 114.84 (17) | C13—C12—H122 | 109.9 |
C1—C2—C3 | 120.12 (18) | H121—C12—H122 | 108.3 |
C4—C3—C2 | 120.79 (18) | O13—C13—N14 | 124.2 (2) |
C4—C3—H3 | 119.6 | O13—C13—C12 | 120.1 (2) |
C2—C3—H3 | 119.6 | N14—C13—C12 | 115.6 (2) |
C3—C4—C10 | 120.99 (18) | N14—C15—H151 | 109.5 |
C3—C4—H4 | 119.5 | N14—C15—H152 | 109.5 |
C10—C4—H4 | 119.5 | H151—C15—H152 | 109.5 |
C6—C5—C10 | 120.95 (19) | N14—C15—H153 | 109.5 |
C6—C5—H5 | 119.5 | H151—C15—H153 | 109.5 |
C10—C5—H5 | 119.5 | H152—C15—H153 | 109.5 |
C5—C6—C7 | 120.38 (19) | N14—C16A—H161 | 109.5 |
C5—C6—H6 | 119.8 | N14—C16A—H162 | 109.5 |
C7—C6—H6 | 119.8 | N14—C16A—H163 | 109.5 |
C8—C7—C6 | 120.44 (19) | N14—C16B—H164 | 109.5 |
C8—C7—H7 | 119.8 | N14—C16B—H165 | 109.5 |
C6—C7—H7 | 119.8 | H164—C16B—H165 | 109.5 |
C7—C8—C9 | 120.70 (18) | N14—C16B—H166 | 109.5 |
C7—C8—H8 | 119.7 | H164—C16B—H166 | 109.5 |
C9—C8—H8 | 119.7 | H165—C16B—H166 | 109.5 |
| | | |
C12—O11—C2—C1 | 4.2 (3) | C1—C9—C10—C5 | 179.98 (17) |
C12—O11—C2—C3 | −175.98 (16) | C8—C9—C10—C5 | 0.0 (3) |
C9—C1—C2—O11 | 178.49 (17) | C1—C9—C10—C4 | −1.4 (3) |
C9—C1—C2—C3 | −1.3 (3) | C8—C9—C10—C4 | 178.67 (16) |
O11—C2—C3—C4 | 179.83 (17) | C3—C4—C10—C5 | 178.31 (18) |
C1—C2—C3—C4 | −0.4 (3) | C3—C4—C10—C9 | −0.3 (3) |
C2—C3—C4—C10 | 1.2 (3) | C2—O11—C12—C13 | 178.56 (16) |
C10—C5—C6—C7 | −0.2 (3) | C15—N14—C13—O13 | −178.3 (2) |
C5—C6—C7—C8 | 0.0 (3) | C16A—N14—C13—O13 | 2.5 (7) |
C6—C7—C8—C9 | 0.1 (3) | C16B—N14—C13—O13 | −20.6 (12) |
C2—C1—C9—C8 | −177.87 (17) | C15—N14—C13—C12 | 2.6 (3) |
C2—C1—C9—C10 | 2.2 (3) | C16A—N14—C13—C12 | −176.6 (6) |
C7—C8—C9—C1 | 179.87 (18) | C16B—N14—C13—C12 | 160.4 (12) |
C7—C8—C9—C10 | −0.2 (3) | O11—C12—C13—O13 | 0.1 (3) |
C6—C5—C10—C9 | 0.2 (3) | O11—C12—C13—N14 | 179.19 (18) |
C6—C5—C10—C4 | −178.42 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H153···O13i | 0.98 | 2.49 | 3.302 (3) | 140 |
C16A—H161···O1Wi | 0.98 | 2.57 | 3.414 (12) | 144 |
C16A—H162···O1Wii | 0.98 | 2.43 | 3.283 (12) | 145 |
C16B—H164···O1Wi | 0.98 | 1.98 | 2.95 (2) | 172 |
C4—H4···Cg2iii | 0.95 | 2.75 | 3.519 (2) | 139 |
C8—H8···Cg1i | 0.95 | 2.70 | 3.440 (2) | 136 |
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, y+1, z; (iii) x, −y, z+1/2. |