N-[4-(2-Morpholino-eth-oxy)phen-yl]acetamide monohydrate.

In the title compound, C(14)H(20)N(2)O(3)·H(2)O, the geometry about the morpholine N atom implies sp(3) hybridization. In the crystal, symmetry-related mol-ecules are linked by inter-molecular N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds, forming infinite chains along the b axis. The chain structure is further stabilized by intra-molecular C-H⋯O inter-actions.

Related literature

For related structures, see: Ahmad et al. (2009 ▶); Fun et al. (2010 ▶); Gowda et al. (2009a ▶,b ▶); Ma et al. (2009 ▶).

Experimental

Crystal data

<span class="Chemical">C14H20N2O3·<span class="Chemical">H2O

M = 282.34

Triclinic,

a = 7.0560 (3) Å

b = 10.2859 (6) Å

c = 10.7234 (6) Å

α = 87.572 (3)°

β = 73.326 (3)°

γ = 79.876 (3)°

V = 733.92 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.603, T max = 0.705

17239 measured reflections

3723 independent reflections

2697 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.138

S = 1.05

3723 reflections

194 parameters

<span class="Disease">H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and ZORTEP (Zsolnai, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810053675/jh2248sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053675/jh2248Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H20N2O3·H2O	V = 733.92 (7) Å3
Mr = 282.34	Z = 2
Triclinic, P1	F(000) = 304
a = 7.0560 (3) Å	Dx = 1.278 Mg m−3
b = 10.2859 (6) Å	Mo Kα radiation, λ = 0.71073 Å
c = 10.7234 (6) Å	µ = 0.09 mm−1
α = 87.572 (3)°	T = 293 K
β = 73.326 (3)°	Block, colourless
γ = 79.876 (3)°	0.30 × 0.25 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	3723 independent reflections
Radiation source: fine-focus sealed tube	2697 reflections with I > 2σ(I)
graphite	Rint = 0.028
multi–scan	θmax = 28.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→9
Tmin = 0.603, Tmax = 0.705	k = −13→13
17239 measured reflections	l = −14→14

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0701P)2 + 0.1005P] where P = (Fo2 + 2Fc2)/3
3723 reflections	(Δ/σ)max < 0.001
194 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	−1.0978 (2)	0.87498 (15)	0.43055 (17)	0.0553 (4)
H1A	−1.1906	0.8271	0.4103	0.083*
H1B	−1.0726	0.9451	0.3692	0.083*
H1C	−1.1540	0.9115	0.5169	0.083*
C2	−0.9045 (2)	0.78313 (14)	0.42318 (14)	0.0469 (3)
C3	−0.54229 (18)	0.74747 (11)	0.30094 (12)	0.0375 (3)
C4	−0.47022 (19)	0.64413 (12)	0.37122 (13)	0.0424 (3)
H4	−0.5557	0.6167	0.4472	0.051*
C5	−0.27177 (19)	0.58104 (12)	0.32949 (13)	0.0429 (3)
H5	−0.2246	0.5123	0.3778	0.051*
C6	−0.14488 (19)	0.62023 (13)	0.21659 (14)	0.0455 (3)
C7	−0.2163 (2)	0.72379 (15)	0.14592 (15)	0.0541 (4)
H7	−0.1311	0.7506	0.0696	0.065*
C8	−0.4117 (2)	0.78676 (13)	0.18802 (14)	0.0465 (3)
H8	−0.4575	0.8567	0.1403	0.056*
C9	0.1304 (2)	0.45012 (14)	0.22585 (16)	0.0514 (4)
H9A	0.0572	0.3790	0.2243	0.062*
H9B	0.1241	0.4676	0.3152	0.062*
C10	0.3450 (2)	0.41666 (14)	0.14270 (15)	0.0492 (3)
H10A	0.3467	0.4195	0.0519	0.059*
H10B	0.4183	0.4836	0.1564	0.059*
C11	0.4840 (2)	0.28395 (14)	0.29775 (15)	0.0494 (3)
H11A	0.3564	0.2987	0.3649	0.059*
H11B	0.5564	0.3542	0.3040	0.059*
C12	0.6040 (2)	0.15244 (16)	0.31893 (16)	0.0588 (4)
H12A	0.6279	0.1526	0.4036	0.071*
H12B	0.5276	0.0829	0.3180	0.071*
C13	0.7573 (2)	0.12794 (15)	0.09625 (16)	0.0567 (4)
H13A	0.6811	0.0594	0.0917	0.068*
H13B	0.8851	0.1096	0.0296	0.068*
C14	0.6448 (2)	0.25923 (15)	0.07117 (15)	0.0516 (4)
H14A	0.7218	0.3279	0.0741	0.062*
H14B	0.6257	0.2590	−0.0149	0.062*
N1	−0.74111 (16)	0.81708 (11)	0.33615 (12)	0.0437 (3)
N2	0.44861 (14)	0.28678 (10)	0.16958 (11)	0.0406 (3)
O1	−0.89898 (17)	0.68586 (13)	0.49128 (14)	0.0801 (4)
O3	0.05217 (15)	0.56571 (11)	0.16672 (11)	0.0655 (3)
O5	0.79129 (15)	0.12632 (12)	0.22060 (12)	0.0651 (3)
O6	1.21505 (19)	0.07084 (12)	0.18771 (14)	0.0651 (3)
H1	−0.757 (2)	0.8870 (18)	0.2907 (16)	0.055 (4)*
H6A	1.095 (4)	0.100 (2)	0.202 (2)	0.081 (6)*
H6B	1.275 (4)	0.138 (2)	0.177 (2)	0.092 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0363 (7)	0.0512 (8)	0.0731 (10)	−0.0017 (6)	−0.0114 (6)	0.0060 (7)
C2	0.0388 (7)	0.0432 (7)	0.0555 (8)	−0.0029 (5)	−0.0119 (6)	0.0080 (6)
C3	0.0352 (6)	0.0306 (6)	0.0449 (7)	−0.0010 (5)	−0.0115 (5)	0.0012 (5)
C4	0.0393 (6)	0.0372 (6)	0.0455 (7)	−0.0012 (5)	−0.0082 (5)	0.0086 (5)
C5	0.0402 (6)	0.0348 (6)	0.0498 (7)	0.0009 (5)	−0.0123 (5)	0.0101 (5)
C6	0.0352 (6)	0.0399 (7)	0.0545 (8)	0.0027 (5)	−0.0085 (5)	0.0079 (6)
C7	0.0410 (7)	0.0529 (8)	0.0569 (9)	0.0004 (6)	−0.0037 (6)	0.0215 (7)
C8	0.0418 (7)	0.0398 (7)	0.0541 (8)	−0.0004 (5)	−0.0136 (6)	0.0156 (6)
C9	0.0386 (7)	0.0436 (7)	0.0610 (9)	0.0055 (5)	−0.0063 (6)	0.0141 (6)
C10	0.0376 (7)	0.0450 (7)	0.0563 (8)	0.0026 (5)	−0.0073 (6)	0.0121 (6)
C11	0.0454 (7)	0.0464 (7)	0.0543 (8)	0.0016 (6)	−0.0163 (6)	0.0011 (6)
C12	0.0510 (8)	0.0591 (9)	0.0628 (9)	0.0069 (7)	−0.0214 (7)	0.0086 (7)
C13	0.0365 (7)	0.0506 (8)	0.0714 (10)	0.0036 (6)	−0.0033 (6)	−0.0010 (7)
C14	0.0355 (7)	0.0531 (8)	0.0559 (8)	0.0011 (6)	−0.0027 (6)	0.0044 (6)
N1	0.0365 (5)	0.0343 (6)	0.0546 (7)	0.0021 (4)	−0.0099 (5)	0.0088 (5)
N2	0.0289 (5)	0.0398 (6)	0.0479 (6)	0.0017 (4)	−0.0076 (4)	0.0042 (4)
O1	0.0478 (6)	0.0771 (8)	0.0989 (10)	−0.0024 (6)	−0.0066 (6)	0.0474 (7)
O3	0.0381 (5)	0.0613 (7)	0.0755 (7)	0.0121 (5)	0.0012 (5)	0.0308 (6)
O5	0.0370 (5)	0.0686 (7)	0.0857 (8)	0.0073 (5)	−0.0218 (5)	0.0077 (6)
O6	0.0418 (6)	0.0487 (6)	0.1051 (10)	−0.0033 (5)	−0.0256 (6)	0.0132 (6)

C1—C2	1.5007 (19)	C9—H9B	0.9700
C1—H1A	0.9600	C10—N2	1.4655 (16)
C1—H1B	0.9600	C10—H10A	0.9700
C1—H1C	0.9600	C10—H10B	0.9700
C2—O1	1.2151 (17)	C11—N2	1.4638 (18)
C2—N1	1.3483 (17)	C11—C12	1.510 (2)
C3—C4	1.3851 (17)	C11—H11A	0.9700
C3—C8	1.3883 (18)	C11—H11B	0.9700
C3—N1	1.4103 (15)	C12—O5	1.4250 (19)
C4—C5	1.3884 (17)	C12—H12A	0.9700
C4—H4	0.9300	C12—H12B	0.9700
C5—C6	1.3760 (19)	C13—O5	1.420 (2)
C5—H5	0.9300	C13—C14	1.497 (2)
C6—O3	1.3632 (15)	C13—H13A	0.9700
C6—C7	1.3873 (18)	C13—H13B	0.9700
C7—C8	1.3707 (18)	C14—N2	1.4695 (16)
C7—H7	0.9300	C14—H14A	0.9700
C8—H8	0.9300	C14—H14B	0.9700
C9—O3	1.4236 (16)	N1—H1	0.860 (18)
C9—C10	1.5079 (18)	O6—H6A	0.82 (2)
C9—H9A	0.9700	O6—H6B	0.86 (3)
C2—C1—H1A	109.5	N2—C10—H10B	108.8
C2—C1—H1B	109.5	C9—C10—H10B	108.8
H1A—C1—H1B	109.5	H10A—C10—H10B	107.7
C2—C1—H1C	109.5	N2—C11—C12	110.39 (12)
H1A—C1—H1C	109.5	N2—C11—H11A	109.6
H1B—C1—H1C	109.5	C12—C11—H11A	109.6
O1—C2—N1	123.54 (13)	N2—C11—H11B	109.6
O1—C2—C1	121.51 (13)	C12—C11—H11B	109.6
N1—C2—C1	114.95 (12)	H11A—C11—H11B	108.1
C4—C3—C8	118.57 (11)	O5—C12—C11	111.16 (13)
C4—C3—N1	124.49 (12)	O5—C12—H12A	109.4
C8—C3—N1	116.94 (11)	C11—C12—H12A	109.4
C3—C4—C5	120.70 (12)	O5—C12—H12B	109.4
C3—C4—H4	119.6	C11—C12—H12B	109.4
C5—C4—H4	119.6	H12A—C12—H12B	108.0
C6—C5—C4	120.00 (12)	O5—C13—C14	110.89 (13)
C6—C5—H5	120.0	O5—C13—H13A	109.5
C4—C5—H5	120.0	C14—C13—H13A	109.5
O3—C6—C5	125.00 (12)	O5—C13—H13B	109.5
O3—C6—C7	115.48 (12)	C14—C13—H13B	109.5
C5—C6—C7	119.51 (12)	H13A—C13—H13B	108.0
C8—C7—C6	120.36 (12)	N2—C14—C13	110.03 (11)
C8—C7—H7	119.8	N2—C14—H14A	109.7
C6—C7—H7	119.8	C13—C14—H14A	109.7
C7—C8—C3	120.84 (12)	N2—C14—H14B	109.7
C7—C8—H8	119.6	C13—C14—H14B	109.7
C3—C8—H8	119.6	H14A—C14—H14B	108.2
O3—C9—C10	103.45 (11)	C2—N1—C3	128.45 (11)
O3—C9—H9A	111.1	C2—N1—H1	118.1 (11)
C10—C9—H9A	111.1	C3—N1—H1	113.3 (11)
O3—C9—H9B	111.1	C11—N2—C10	111.50 (11)
C10—C9—H9B	111.1	C11—N2—C14	107.90 (11)
H9A—C9—H9B	109.0	C10—N2—C14	108.26 (10)
N2—C10—C9	113.88 (11)	C6—O3—C9	118.64 (10)
N2—C10—H10A	108.8	C13—O5—C12	109.68 (11)
C9—C10—H10A	108.8	H6A—O6—H6B	106 (2)
C8—C3—C4—C5	−0.1 (2)	C9—C10—N2—C11	−68.97 (16)
N1—C3—C4—C5	−179.93 (12)	C9—C10—N2—C14	172.48 (13)
C3—C4—C5—C6	−0.6 (2)	C13—C14—N2—C11	58.35 (15)
C4—C5—C6—O3	179.86 (13)	C13—C14—N2—C10	179.16 (13)
C4—C5—C6—C7	0.7 (2)	C5—C6—O3—C9	7.5 (2)
O3—C6—C7—C8	−179.30 (14)	C7—C6—O3—C9	−173.29 (14)
C5—C6—C7—C8	0.0 (2)	C10—C9—O3—C6	177.79 (13)
C6—C7—C8—C3	−0.7 (2)	C14—C13—O5—C12	59.49 (16)
C4—C3—C8—C7	0.8 (2)	C11—C12—O5—C13	−58.19 (17)
N1—C3—C8—C7	−179.40 (13)	O1—C2—N1—C3	4.2 (3)
O3—C9—C10—N2	−169.50 (12)	C1—C2—N1—C3	−175.68 (13)
N2—C11—C12—O5	58.19 (16)	C2—N1—C3—C4	−15.1 (2)
O5—C13—C14—N2	−60.57 (16)	C2—N1—C3—C8	165.11 (14)
O1—C2—N1—C3	4.2 (3)	C7—C6—O3—C9	−173.29 (14)
C1—C2—N1—C3	−175.68 (13)	C5—C6—O3—C9	7.5 (2)
C4—C3—N1—C2	−15.1 (2)	C6—O3—C9—C10	177.79 (13)
C8—C3—N1—C2	165.11 (14)	O3—C9—C10—N2	−169.50 (12)
C12—C11—N2—C10	−175.90 (11)	C9—C10—N2—C11	−68.97 (16)
C12—C11—N2—C14	−57.14 (15)	C9—C10—N2—C14	172.48 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6i	0.860 (18)	2.157 (18)	3.0148 (17)	174.8 (14)
O6—H6A···O5	0.82 (2)	2.06 (3)	2.8640 (18)	165 (2)
O6—H6B···N2ii	0.86 (3)	2.11 (2)	2.9586 (17)	171 (2)
C4—H4···O1	0.93	2.32	2.8896 (19)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6i	0.860 (18)	2.157 (18)	3.0148 (17)	174.8 (14)
O6—H6A⋯O5	0.82 (2)	2.06 (3)	2.8640 (18)	165 (2)
O6—H6B⋯N2	0.86 (3)	2.11 (2)	2.9586 (17)	171 (2)
C4—H4⋯O1	0.93 (3)	2.32	2.890 (2)	120

Symmetry code: (i) .