N-Methyl-N-phenyl-2-(quinolin-8-yl-oxy)acetamide monohydrate.

In the title compound, C(18)H(16)N(2)O(2)·H(2)O, the dihedral angle between the quinoline ring system and the benzene ring is 87.19 (8)°. In the crystal, water mol-ecules are linked to acetamide mol-ecules via inter-molecular O-H⋯N and O-H⋯O hydrogen bonds.

Related literature

For the luminescent properties of lanthanide complexes with amide-type ligands, see: Li et al. (2003 ▶); Wu et al. (2008 ▶). For the synthesis of 2-chloro-N-methyl-N-phenyl­acetamide, see: Zhi et al. (2011 ▶). For the similar structure of N-phenyl-2-(quinolin-8-yl­oxy)acetamide hemihydrate, see: Li et al. (2005 ▶).

Experimental

Crystal data

C18H16N2O2·H2O

M = 310.34

Orthorhombic,

a = 6.6028 (8) Å

b = 14.9207 (18) Å

c = 16.3505 (19) Å

V = 1610.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.16 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.986, T max = 0.991

10373 measured reflections

3911 independent reflections

3113 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.101

S = 1.05

3911 reflections

217 parameters

125 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017181/vm2091sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017181/vm2091Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811017181/vm2091Isup3.cml

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

C18H16N2O2·H2O	F(000) = 656
Mr = 310.34	Dx = 1.280 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	θ = 1.9–28.2°
a = 6.6028 (8) Å	µ = 0.09 mm−1
b = 14.9207 (18) Å	T = 296 K
c = 16.3505 (19) Å	Block, colorless
V = 1610.8 (3) Å3	0.16 × 0.15 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	3911 independent reflections
Radiation source: fine-focus sealed tube	3113 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 28.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→8
Tmin = 0.986, Tmax = 0.991	k = −19→18
10373 measured reflections	l = −21→18

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.0847P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.005
3911 reflections	Δρmax = 0.12 e Å−3
217 parameters	Δρmin = −0.14 e Å−3
125 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0132 (19)

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
O1	0.80212 (17)	0.10711 (7)	0.15970 (6)	0.0452 (3)
O2	0.8822 (2)	0.06977 (8)	0.31349 (8)	0.0583 (4)
C8	0.7564 (3)	0.12177 (10)	0.07926 (9)	0.0420 (4)
N2	0.6671 (2)	0.17225 (9)	0.36347 (8)	0.0471 (3)
N1	1.0695 (2)	0.04605 (10)	0.05053 (9)	0.0510 (4)
C10	0.6699 (3)	0.14635 (11)	0.21760 (9)	0.0440 (4)
H10A	0.5345	0.1221	0.2113	0.053*
H10B	0.6637	0.2107	0.2095	0.053*
C11	0.7500 (2)	0.12557 (10)	0.30174 (10)	0.0419 (3)
C9	0.9020 (3)	0.08886 (10)	0.02220 (10)	0.0437 (4)
C13	0.5129 (2)	0.23910 (10)	0.35189 (9)	0.0415 (4)
C7	0.5874 (3)	0.16515 (12)	0.05232 (12)	0.0552 (5)
H7	0.4921	0.1860	0.0896	0.066*
C18	0.5634 (3)	0.32878 (11)	0.35671 (12)	0.0525 (4)
H18	0.6969	0.3456	0.3665	0.063*
C4	0.8680 (3)	0.10316 (12)	−0.06202 (11)	0.0574 (5)
C14	0.3166 (3)	0.21536 (12)	0.33744 (12)	0.0560 (5)
H14	0.2810	0.1551	0.3349	0.067*
C17	0.4168 (3)	0.39294 (12)	0.34698 (13)	0.0596 (5)
H17	0.4515	0.4532	0.3504	0.072*
C2	1.1823 (4)	0.02794 (15)	−0.08759 (13)	0.0711 (5)
H2	1.2811	0.0065	−0.1230	0.085*
C3	1.0166 (4)	0.07026 (13)	−0.11641 (12)	0.0676 (5)
H3	1.0001	0.0778	−0.1725	0.081*
C12	0.7333 (4)	0.15493 (14)	0.44699 (11)	0.0660 (5)
H12A	0.8400	0.1112	0.4465	0.099*
H12B	0.6214	0.1326	0.4785	0.099*
H12C	0.7821	0.2095	0.4710	0.099*
C1	1.2014 (3)	0.01726 (14)	−0.00346 (12)	0.0651 (5)
H1	1.3157	−0.0124	0.0159	0.078*
C15	0.1708 (3)	0.28045 (14)	0.32658 (14)	0.0636 (5)
H15	0.0379	0.2638	0.3153	0.076*
C16	0.2201 (3)	0.36932 (13)	0.33224 (11)	0.0572 (5)
H16	0.1210	0.4131	0.3261	0.069*
C6	0.5576 (4)	0.17827 (13)	−0.03189 (14)	0.0698 (6)
H6	0.4425	0.2084	−0.0497	0.084*
C5	0.6923 (4)	0.14804 (14)	−0.08755 (13)	0.0716 (6)
H5	0.6686	0.1570	−0.1430	0.086*
O1W	1.2156 (2)	0.02723 (13)	0.21238 (9)	0.0780 (5)
H1WA	1.116 (3)	0.039 (2)	0.2438 (12)	0.117*
H1WB	1.175 (4)	0.035 (2)	0.1629 (7)	0.117*

	U11	U22	U33	U12	U13	U23
O1	0.0470 (6)	0.0525 (6)	0.0361 (6)	0.0104 (5)	0.0031 (5)	−0.0040 (5)
O2	0.0599 (8)	0.0629 (7)	0.0521 (7)	0.0214 (7)	0.0033 (6)	0.0043 (6)
C8	0.0488 (9)	0.0365 (7)	0.0408 (8)	−0.0012 (7)	−0.0025 (7)	−0.0026 (6)
N2	0.0526 (8)	0.0498 (7)	0.0388 (7)	0.0069 (7)	−0.0004 (6)	−0.0044 (6)
N1	0.0518 (8)	0.0548 (8)	0.0464 (8)	0.0031 (7)	0.0078 (7)	−0.0076 (7)
C10	0.0421 (8)	0.0464 (8)	0.0434 (9)	0.0066 (7)	0.0034 (7)	−0.0065 (6)
C11	0.0407 (8)	0.0403 (7)	0.0447 (8)	−0.0014 (7)	0.0044 (7)	0.0006 (6)
C9	0.0550 (10)	0.0375 (8)	0.0387 (8)	−0.0057 (7)	0.0012 (7)	−0.0039 (6)
C13	0.0455 (9)	0.0432 (8)	0.0359 (8)	0.0022 (7)	0.0068 (7)	−0.0048 (6)
C7	0.0585 (11)	0.0503 (9)	0.0567 (11)	0.0080 (9)	−0.0105 (9)	−0.0038 (8)
C18	0.0482 (9)	0.0485 (9)	0.0609 (11)	−0.0033 (9)	0.0073 (8)	−0.0083 (8)
C4	0.0805 (12)	0.0517 (9)	0.0399 (9)	−0.0131 (9)	0.0012 (8)	−0.0027 (7)
C14	0.0520 (10)	0.0456 (9)	0.0702 (12)	−0.0054 (8)	0.0062 (9)	−0.0068 (8)
C17	0.0673 (12)	0.0426 (9)	0.0688 (12)	−0.0005 (9)	0.0122 (10)	−0.0021 (8)
C2	0.0772 (12)	0.0777 (11)	0.0583 (10)	−0.0052 (11)	0.0226 (10)	−0.0194 (9)
C3	0.0946 (13)	0.0671 (10)	0.0410 (9)	−0.0168 (10)	0.0102 (9)	−0.0082 (8)
C12	0.0814 (14)	0.0756 (12)	0.0409 (9)	0.0124 (11)	−0.0048 (10)	−0.0004 (8)
C1	0.0650 (11)	0.0710 (10)	0.0594 (10)	0.0011 (10)	0.0170 (9)	−0.0157 (8)
C15	0.0460 (10)	0.0669 (12)	0.0779 (13)	0.0010 (9)	0.0040 (10)	−0.0074 (10)
C16	0.0607 (12)	0.0571 (10)	0.0538 (10)	0.0140 (9)	0.0081 (9)	0.0007 (8)
C6	0.0790 (14)	0.0625 (11)	0.0680 (13)	0.0115 (11)	−0.0239 (11)	0.0068 (10)
C5	0.1004 (17)	0.0673 (12)	0.0472 (11)	−0.0026 (12)	−0.0181 (12)	0.0063 (9)
O1W	0.0531 (8)	0.1216 (12)	0.0594 (8)	0.0265 (9)	−0.0078 (7)	−0.0196 (9)

O1—C8	1.3670 (19)	C4—C3	1.412 (3)
O1—C10	1.4148 (19)	C14—C15	1.379 (3)
O2—C11	1.2217 (19)	C14—H14	0.9300
C8—C7	1.363 (2)	C17—C16	1.367 (3)
C8—C9	1.427 (2)	C17—H17	0.9300
N2—C11	1.343 (2)	C2—C3	1.348 (3)
N2—C13	1.438 (2)	C2—C1	1.391 (3)
N2—C12	1.457 (2)	C2—H2	0.9300
N1—C1	1.312 (2)	C3—H3	0.9300
N1—C9	1.358 (2)	C12—H12A	0.9600
C10—C11	1.506 (2)	C12—H12B	0.9600
C10—H10A	0.9700	C12—H12C	0.9600
C10—H10B	0.9700	C1—H1	0.9300
C9—C4	1.412 (2)	C15—C16	1.368 (3)
C13—C14	1.364 (3)	C15—H15	0.9300
C13—C18	1.381 (2)	C16—H16	0.9300
C7—C6	1.405 (3)	C6—C5	1.350 (3)
C7—H7	0.9300	C6—H6	0.9300
C18—C17	1.371 (3)	C5—H5	0.9300
C18—H18	0.9300	O1W—H1WA	0.855 (10)
C4—C5	1.403 (3)	O1W—H1WB	0.860 (10)
C8—O1—C10	116.19 (12)	C13—C14—H14	119.9
C7—C8—O1	124.58 (15)	C15—C14—H14	119.9
C7—C8—C9	120.25 (15)	C16—C17—C18	120.76 (17)
O1—C8—C9	115.17 (14)	C16—C17—H17	119.6
C11—N2—C13	123.34 (13)	C18—C17—H17	119.6
C11—N2—C12	119.34 (15)	C3—C2—C1	118.3 (2)
C13—N2—C12	117.32 (14)	C3—C2—H2	120.9
C1—N1—C9	117.70 (16)	C1—C2—H2	120.9
O1—C10—C11	108.01 (13)	C2—C3—C4	120.4 (2)
O1—C10—H10A	110.1	C2—C3—H3	119.8
C11—C10—H10A	110.1	C4—C3—H3	119.8
O1—C10—H10B	110.1	N2—C12—H12A	109.5
C11—C10—H10B	110.1	N2—C12—H12B	109.5
H10A—C10—H10B	108.4	H12A—C12—H12B	109.5
O2—C11—N2	121.78 (15)	N2—C12—H12C	109.5
O2—C11—C10	122.34 (14)	H12A—C12—H12C	109.5
N2—C11—C10	115.88 (14)	H12B—C12—H12C	109.5
N1—C9—C4	122.23 (16)	N1—C1—C2	124.6 (2)
N1—C9—C8	119.17 (14)	N1—C1—H1	117.7
C4—C9—C8	118.59 (17)	C2—C1—H1	117.7
C14—C13—C18	119.42 (16)	C16—C15—C14	120.51 (19)
C14—C13—N2	121.02 (15)	C16—C15—H15	119.7
C18—C13—N2	119.55 (15)	C14—C15—H15	119.7
C8—C7—C6	119.84 (19)	C17—C16—C15	119.19 (19)
C8—C7—H7	120.1	C17—C16—H16	120.4
C6—C7—H7	120.1	C15—C16—H16	120.4
C17—C18—C13	119.93 (17)	C5—C6—C7	121.5 (2)
C17—C18—H18	120.0	C5—C6—H6	119.3
C13—C18—H18	120.0	C7—C6—H6	119.3
C5—C4—C9	119.61 (18)	C6—C5—C4	120.24 (19)
C5—C4—C3	123.58 (19)	C6—C5—H5	119.9
C9—C4—C3	116.8 (2)	C4—C5—H5	119.9
C13—C14—C15	120.17 (17)	H1WA—O1W—H1WB	107.3 (16)
C10—O1—C8—C7	−5.0 (2)	C14—C13—C18—C17	0.0 (3)
C10—O1—C8—C9	174.32 (13)	N2—C13—C18—C17	−179.02 (16)
C8—O1—C10—C11	−177.88 (13)	N1—C9—C4—C5	−179.83 (17)
C13—N2—C11—O2	179.28 (15)	C8—C9—C4—C5	−0.7 (2)
C12—N2—C11—O2	−1.2 (2)	N1—C9—C4—C3	0.3 (2)
C13—N2—C11—C10	−0.7 (2)	C8—C9—C4—C3	179.43 (15)
C12—N2—C11—C10	178.81 (16)	C18—C13—C14—C15	0.9 (3)
O1—C10—C11—O2	−12.8 (2)	N2—C13—C14—C15	179.93 (17)
O1—C10—C11—N2	167.15 (14)	C13—C18—C17—C16	−0.2 (3)
C1—N1—C9—C4	−0.3 (2)	C1—C2—C3—C4	0.4 (3)
C1—N1—C9—C8	−179.41 (16)	C5—C4—C3—C2	179.79 (19)
C7—C8—C9—N1	179.84 (15)	C9—C4—C3—C2	−0.4 (3)
O1—C8—C9—N1	0.5 (2)	C9—N1—C1—C2	0.4 (3)
C7—C8—C9—C4	0.7 (2)	C3—C2—C1—N1	−0.4 (3)
O1—C8—C9—C4	−178.61 (14)	C13—C14—C15—C16	−1.7 (3)
C11—N2—C13—C14	77.0 (2)	C18—C17—C16—C15	−0.5 (3)
C12—N2—C13—C14	−102.5 (2)	C14—C15—C16—C17	1.5 (3)
C11—N2—C13—C18	−103.99 (19)	C8—C7—C6—C5	0.6 (3)
C12—N2—C13—C18	76.5 (2)	C7—C6—C5—C4	−0.7 (3)
O1—C8—C7—C6	178.61 (17)	C9—C4—C5—C6	0.7 (3)
C9—C8—C7—C6	−0.7 (3)	C3—C4—C5—C6	−179.47 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2	0.86 (1)	1.97 (1)	2.8249 (19)	178 (3)
O1W—H1WB···N1	0.86 (1)	1.97 (1)	2.831 (2)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O2	0.86 (1)	1.97 (1)	2.8249 (19)	178 (3)
O1W—H1WB⋯N1	0.86 (1)	1.97 (1)	2.831 (2)	176 (3)