N,N-Di­methyl-2-(2-naphthyl­oxy)­acet­amide monohydrate

The title compound, C₁₄H₁₅NO₂·H₂O, 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.

Key indicators

• Single-crystal X-ray study
• T = 160 K
• Mean [sigma](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?

---

Computing details

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

Crystal data

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) Å^3	0.25 × 0.23 × 0.05 mm
Z = 8

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.213	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.1228P)^2 + 1.8212P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H153···O13^i	0.98	2.49	3.302 (3)	140
C16A—H161···O1W^i	0.98	2.57	3.414 (12)	144
C16A—H162···O1W^ii	0.98	2.43	3.283 (12)	145
C16B—H164···O1W^i	0.98	1.98	2.95 (2)	172
C4—H4···Cg2^iii	0.95	2.75	3.519 (2)	139
C8—H8···Cg1^i	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.