In the title compound, C20H24N2O5·H2O, the molecules are linked to each other by hydrogen bonds, and form a supramolecular chain structure. The organic and water molecules lie on crystallographic twofold rotation axes.
Supporting information
CCDC reference: 209925
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- H-atom completeness 93%
- R factor = 0.049
- wR factor = 0.124
- Data-to-parameter ratio = 13.6
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:C20 H26 N2 O6
Atom count from the _atom_site data: C20 H24 N2 O6
CELLZ_01
From the CIF: _cell_formula_units_Z 4
From the CIF: _chemical_formula_sum C20 H26 N2 O6
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 80.00 80.00 0.00
H 104.00 96.00 8.00
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?
The title compound was prepared by the direct reaction of chlorocarbonylmethoxyacetyl chloride with 4-ethoxyphenylamine in pyridine. The resulting mixture was separated by flash chromatography (ethyl acetate/benzene, 1:4). Suitable crystals were obtained by evaporation of an ethanol solution. Spectroscopic analysis, IR (KBr, ν, cm−1): 1666, 1117, 1235; 1H NMR (CDCl3, δ): 4.24 (s, 2H), 8.23 (s, 1H), 6.81–7.53 (d, 1H), 3.87–4.13 (d, 2H), 1.25–1.42 (d, 3H); analysis, calculated for C20H26N2O6: C 61.53, H 6.71, N 7.17%; found: C 61.94, H 6.44, N 7.06%.
All H atoms were positioned geometrically and refined with riding model constraints, except for those on the water molecule, which were not included.
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
N-(4-Ethoxyphenyl)-2-[(4-ethoxyphenylcarbamoyl)methoxy]acetamide monohydrate
top
Crystal data top
C20H24N2O5·H2O | F(000) = 832 |
Mr = 390.43 | Dx = 1.285 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 30.575 (5) Å | Cell parameters from 25 reflections |
b = 7.929 (1) Å | θ = 2.7–12.1° |
c = 8.356 (2) Å | µ = 0.10 mm−1 |
β = 95.09 (2)° | T = 294 K |
V = 2017.7 (6) Å3 | Rhomboidal plate, colourless |
Z = 4 | 0.70 × 0.52 × 0.06 mm |
Data collection top
Siemens P4 diffractometer | Rint = 0.034 |
Radiation source: normal-focus sealed tube | θmax = 25.0°, θmin = 2.7° |
Graphite monochromator | h = 0→36 |
ω scans | k = 0→9 |
2017 measured reflections | l = −9→9 |
1771 independent reflections | 3 standard reflections every 97 reflections |
880 reflections with I > 2σ(I) | intensity decay: 4.4% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.0559P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.84 | (Δ/σ)max < 0.001 |
1771 reflections | Δρmax = 0.15 e Å−3 |
130 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0027 (6) |
Crystal data top
C20H24N2O5·H2O | V = 2017.7 (6) Å3 |
Mr = 390.43 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 30.575 (5) Å | µ = 0.10 mm−1 |
b = 7.929 (1) Å | T = 294 K |
c = 8.356 (2) Å | 0.70 × 0.52 × 0.06 mm |
β = 95.09 (2)° | |
Data collection top
Siemens P4 diffractometer | Rint = 0.034 |
2017 measured reflections | 3 standard reflections every 97 reflections |
1771 independent reflections | intensity decay: 4.4% |
880 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 0.84 | Δρmax = 0.15 e Å−3 |
1771 reflections | Δρmin = −0.20 e Å−3 |
130 parameters | |
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 | |
O1 | 0.0000 | 0.1183 (3) | 1.2500 | 0.0469 (7) | |
O2 | 0.06068 (6) | 0.1831 (2) | 0.9153 (2) | 0.0536 (6) | |
O3 | 0.18409 (7) | −0.4539 (3) | 0.8299 (3) | 0.0700 (7) | |
N | 0.06454 (7) | −0.0315 (3) | 1.0971 (3) | 0.0458 (6) | |
H0N | 0.0543 | −0.0663 | 1.1838 | 0.055* | |
C1 | 0.02234 (9) | 0.2202 (3) | 1.1447 (3) | 0.0451 (7) | |
H1A | 0.0405 | 0.3010 | 1.2074 | 0.054* | |
H1B | 0.0010 | 0.2829 | 1.0756 | 0.054* | |
C2 | 0.05087 (8) | 0.1196 (3) | 1.0418 (3) | 0.0423 (7) | |
C3 | 0.09447 (9) | −0.1403 (3) | 1.0260 (3) | 0.0438 (7) | |
C4 | 0.09012 (9) | −0.3115 (3) | 1.0404 (3) | 0.0497 (8) | |
H4 | 0.0673 | −0.3546 | 1.0947 | 0.060* | |
C5 | 0.11898 (9) | −0.4216 (3) | 0.9759 (3) | 0.0531 (8) | |
H5 | 0.1155 | −0.5374 | 0.9869 | 0.064* | |
C6 | 0.15272 (9) | −0.3593 (4) | 0.8956 (3) | 0.0531 (8) | |
C7 | 0.15682 (10) | −0.1875 (4) | 0.8780 (4) | 0.0672 (10) | |
H7 | 0.1794 | −0.1448 | 0.8221 | 0.081* | |
C8 | 0.12789 (9) | −0.0774 (4) | 0.9423 (4) | 0.0620 (9) | |
H8 | 0.1309 | 0.0383 | 0.9292 | 0.074* | |
C9 | 0.18480 (10) | −0.6306 (4) | 0.8604 (4) | 0.0674 (10) | |
H9A | 0.1582 | −0.6831 | 0.8115 | 0.081* | |
H9B | 0.1868 | −0.6521 | 0.9751 | 0.081* | |
C10 | 0.22438 (11) | −0.7002 (4) | 0.7884 (4) | 0.0916 (12) | |
H10A | 0.2215 | −0.6816 | 0.6745 | 0.110* | |
H10B | 0.2266 | −0.8190 | 0.8097 | 0.110* | |
H10C | 0.2503 | −0.6444 | 0.8352 | 0.110* | |
O4 | 0.0000 | 0.4023 (4) | 0.7500 | 0.0973 (12) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0530 (16) | 0.0415 (15) | 0.0502 (16) | 0.000 | 0.0261 (14) | 0.000 |
O2 | 0.0674 (13) | 0.0465 (12) | 0.0507 (12) | 0.0014 (10) | 0.0269 (10) | 0.0053 (10) |
O3 | 0.0613 (14) | 0.0569 (14) | 0.0966 (17) | 0.0119 (11) | 0.0335 (12) | 0.0005 (12) |
N | 0.0504 (15) | 0.0452 (14) | 0.0445 (14) | 0.0027 (12) | 0.0184 (12) | 0.0052 (12) |
C1 | 0.0542 (17) | 0.0384 (16) | 0.0450 (15) | −0.0022 (14) | 0.0175 (14) | 0.0004 (14) |
C2 | 0.0394 (15) | 0.0439 (17) | 0.0442 (16) | −0.0052 (14) | 0.0081 (13) | −0.0038 (15) |
C3 | 0.0433 (16) | 0.0445 (17) | 0.0450 (16) | 0.0016 (14) | 0.0123 (13) | 0.0023 (14) |
C4 | 0.0441 (17) | 0.0450 (17) | 0.0623 (19) | −0.0005 (15) | 0.0175 (15) | 0.0075 (16) |
C5 | 0.0516 (18) | 0.0377 (17) | 0.072 (2) | 0.0021 (15) | 0.0134 (16) | 0.0011 (15) |
C6 | 0.0466 (17) | 0.0506 (19) | 0.0641 (19) | 0.0053 (16) | 0.0164 (15) | −0.0034 (16) |
C7 | 0.054 (2) | 0.061 (2) | 0.092 (2) | 0.0011 (18) | 0.0368 (18) | 0.009 (2) |
C8 | 0.0539 (19) | 0.0441 (18) | 0.092 (2) | 0.0013 (15) | 0.0295 (18) | 0.0070 (17) |
C9 | 0.059 (2) | 0.059 (2) | 0.085 (2) | 0.0143 (17) | 0.0084 (18) | −0.0059 (19) |
C10 | 0.086 (3) | 0.089 (3) | 0.102 (3) | 0.040 (2) | 0.024 (2) | −0.005 (2) |
O4 | 0.111 (3) | 0.077 (2) | 0.108 (3) | 0.000 | 0.033 (2) | 0.000 |
Geometric parameters (Å, º) top
O1—C1i | 1.414 (3) | C1—C2 | 1.506 (3) |
O1—C1 | 1.414 (3) | C3—C4 | 1.371 (3) |
O2—C2 | 1.232 (3) | C3—C8 | 1.381 (3) |
O2—O4 | 2.813 (3) | C4—C5 | 1.384 (3) |
O3—C6 | 1.370 (3) | C5—C6 | 1.371 (3) |
O3—C9 | 1.424 (3) | C6—C7 | 1.377 (4) |
N—C2 | 1.338 (3) | C7—C8 | 1.384 (4) |
N—C3 | 1.425 (3) | C9—C10 | 1.503 (4) |
| | | |
C1i—O1—C1 | 110.3 (3) | C8—C3—N | 121.6 (2) |
C2—O2—O4 | 118.28 (16) | C3—C4—C5 | 121.3 (3) |
C6—O3—C9 | 117.8 (2) | C6—C5—C4 | 119.8 (3) |
C2—N—C3 | 126.2 (2) | O3—C6—C5 | 125.6 (3) |
O1—C1—C2 | 112.9 (2) | O3—C6—C7 | 115.2 (3) |
O2—C2—N | 124.8 (2) | C5—C6—C7 | 119.2 (3) |
O2—C2—C1 | 118.1 (2) | C6—C7—C8 | 121.0 (3) |
N—C2—C1 | 117.1 (2) | C3—C8—C7 | 119.7 (3) |
C4—C3—C8 | 118.9 (3) | O3—C9—C10 | 106.8 (3) |
C4—C3—N | 119.5 (2) | | |
| | | |
C1i—O1—C1—C2 | 173.6 (3) | C3—C4—C5—C6 | 0.0 (5) |
O4—O2—C2—N | 149.7 (2) | C9—O3—C6—C5 | −6.7 (5) |
O4—O2—C2—C1 | −31.8 (3) | C9—O3—C6—C7 | 172.7 (3) |
C3—N—C2—O2 | 3.9 (4) | C4—C5—C6—O3 | 178.2 (3) |
C3—N—C2—C1 | −174.5 (2) | C4—C5—C6—C7 | −1.2 (5) |
O1—C1—C2—O2 | 157.7 (2) | O3—C6—C7—C8 | −178.4 (3) |
O1—C1—C2—N | −23.7 (3) | C5—C6—C7—C8 | 1.1 (5) |
C2—N—C3—C4 | −148.3 (3) | C4—C3—C8—C7 | −1.4 (5) |
C2—N—C3—C8 | 31.7 (4) | N—C3—C8—C7 | 178.6 (3) |
C8—C3—C4—C5 | 1.3 (5) | C6—C7—C8—C3 | 0.3 (5) |
N—C3—C4—C5 | −178.7 (3) | C6—O3—C9—C10 | −174.9 (3) |
Symmetry code: (i) −x, y, −z+5/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N—H0N···O2ii | 0.86 | 2.14 | 2.930 (3) | 153 |
C4—H4···O4iii | 0.93 | 2.56 | 3.469 (3) | 167 |
Symmetry codes: (ii) x, −y, z+1/2; (iii) −x, −y, −z+2. |
Experimental details
Crystal data |
Chemical formula | C20H24N2O5·H2O |
Mr | 390.43 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 294 |
a, b, c (Å) | 30.575 (5), 7.929 (1), 8.356 (2) |
β (°) | 95.09 (2) |
V (Å3) | 2017.7 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.70 × 0.52 × 0.06 |
|
Data collection |
Diffractometer | Siemens P4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2017, 1771, 880 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.594 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.124, 0.84 |
No. of reflections | 1771 |
No. of parameters | 130 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.20 |
Selected geometric parameters (Å, º) topO1—C1i | 1.414 (3) | O3—C9 | 1.424 (3) |
O1—C1 | 1.414 (3) | N—C2 | 1.338 (3) |
O2—C2 | 1.232 (3) | N—C3 | 1.425 (3) |
O2—O4 | 2.813 (3) | C1—C2 | 1.506 (3) |
O3—C6 | 1.370 (3) | C9—C10 | 1.503 (4) |
| | | |
C1i—O1—C1 | 110.3 (3) | N—C2—C1 | 117.1 (2) |
C2—O2—O4 | 118.28 (16) | C4—C3—C8 | 118.9 (3) |
C6—O3—C9 | 117.8 (2) | C4—C3—N | 119.5 (2) |
C2—N—C3 | 126.2 (2) | C8—C3—N | 121.6 (2) |
O1—C1—C2 | 112.9 (2) | O3—C6—C5 | 125.6 (3) |
O2—C2—N | 124.8 (2) | O3—C6—C7 | 115.2 (3) |
O2—C2—C1 | 118.1 (2) | O3—C9—C10 | 106.8 (3) |
Symmetry code: (i) −x, y, −z+5/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N—H0N···O2ii | 0.86 | 2.14 | 2.930 (3) | 153 |
C4—H4···O4iii | 0.93 | 2.56 | 3.469 (3) | 167 |
Symmetry codes: (ii) x, −y, z+1/2; (iii) −x, −y, −z+2. |
Hydrogen-bonding interactions are regarded as among the most important driving forces in crystal engineering (Ranganaham et al., 1999). Whitesides et al. (1995) have designed a family of self-assembled aggregates by hydrogen bonding between cyanuric acid and melamine. Recently, this method was also introduced for the construction of supramolecular nanostructures (Kosonen et al., 2000). In this work, hydrogen bonds between water and the O atoms of C20H24N2O5 were used to form a novel supramolecular cavity.
In the title compound, (I), the water molecule (O4) forms two hydrogen bonds with O2 and a symmetry-equivalent O2, the O4···O2 distance being 2.813 (3) Å, and the angle at O4 being 103.7 (2) Å. N—H forms a hydrogen bond with an O atom of another molecule (Table 2).
The molecules are linked by O···O and N···O hydrogen bonds and construct a one-dimensional supramolecular chain structure (Fig. 2). Adjacent molecules adopt opposite orientations due to the bulk of the benzene rings. A cavity formed by hydrogen bonds is observed (Fig. 3).