N-(4-Chloro-phen-yl)-2-(8-quinol-yloxy)acetamide monohydrate.

In the title compound, C(17)H(13)ClN(2)O(2)·H(2)O, the dihedral angle between the quinoline ring system and the benzene ring is 13.0 (1)°. An intra-molecular N-H⋯O hydrogen bond may influence the mol-ecular conformation. In the crystal structure, acetamide mol-ecules are linked to water mol-ecules via inter-molecular O-H⋯ N and N-H⋯O hydrogen bonds and in turn linked into chains along [010] via O-H⋯O hydrogen bonds.

Related literature

For the synthesis of the title compound and its lanthanide complexes, see: Wu et al. (2008 ▶). For related structures, see: Zhang et al. (2006 ▶); Wu et al. (2010 ▶).

Experimental

Crystal data

C17H13ClN2O2·H2O

M = 330.76

Orthorhombic,

a = 19.4984 (19) Å

b = 5.2601 (6) Å

c = 29.851 (3) Å

V = 3061.7 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.32 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.929, T max = 0.948

15222 measured reflections

3622 independent reflections

1800 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.128

S = 1.00

3622 reflections

217 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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/S1600536810026206/lh5076sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026206/lh5076Isup2.hkl

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

C17H13ClN2O2·H2O	F(000) = 1376
Mr = 330.76	Dx = 1.435 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1957 reflections
a = 19.4984 (19) Å	θ = 2.5–19.9°
b = 5.2601 (6) Å	µ = 0.27 mm−1
c = 29.851 (3) Å	T = 296 K
V = 3061.7 (5) Å3	Block, colorless
Z = 8	0.32 × 0.23 × 0.20 mm

Bruker SMART CCD diffractometer	3622 independent reflections
Radiation source: sealed tube	1800 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ and ω scans	θmax = 28.1°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→25
Tmin = 0.929, Tmax = 0.948	k = −6→4
15222 measured reflections	l = −39→39

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0548P)2 + 0.0231P] where P = (Fo2 + 2Fc2)/3
3622 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.16 e Å−3
4 restraints	Δρmin = −0.21 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
Cl1	0.32260 (4)	0.36909 (15)	0.044180 (19)	0.0858 (3)
O2	0.40858 (7)	0.1726 (3)	0.32297 (4)	0.0532 (4)
N2	0.34502 (9)	0.5390 (3)	0.36817 (6)	0.0505 (5)
N1	0.38877 (10)	0.1567 (3)	0.23341 (6)	0.0524 (5)
C10	0.47572 (12)	0.0589 (4)	0.38814 (7)	0.0568 (6)
H10	0.4991	−0.0675	0.3726	0.068*
C17	0.39211 (11)	0.3959 (4)	0.39023 (6)	0.0454 (5)
C13	0.40699 (12)	0.4337 (4)	0.43606 (7)	0.0522 (6)
C7	0.42016 (11)	−0.0454 (4)	0.25142 (7)	0.0506 (6)
C9	0.42715 (11)	0.2012 (4)	0.36669 (6)	0.0470 (5)
C11	0.49027 (12)	0.1029 (5)	0.43328 (8)	0.0647 (7)
H11	0.5238	0.0060	0.4474	0.078*
C12	0.45676 (13)	0.2827 (4)	0.45688 (7)	0.0618 (7)
H12	0.4667	0.3065	0.4871	0.074*
C14	0.37041 (14)	0.6238 (5)	0.45851 (7)	0.0650 (7)
H14	0.3782	0.6522	0.4888	0.078*
O1	0.43645 (9)	−0.2349 (3)	0.23095 (5)	0.0771 (5)
C1	0.34138 (12)	0.3011 (5)	0.09954 (7)	0.0564 (6)
C8	0.43823 (12)	−0.0380 (4)	0.30005 (7)	0.0529 (6)
H8A	0.4228	−0.1942	0.3141	0.063*
H8B	0.4877	−0.0298	0.3030	0.063*
C4	0.37288 (11)	0.1944 (4)	0.18780 (7)	0.0480 (5)
C3	0.33244 (12)	0.3998 (4)	0.17682 (7)	0.0569 (6)
H3	0.3155	0.5039	0.1995	0.068*
C2	0.31662 (12)	0.4537 (5)	0.13280 (7)	0.0612 (6)
H2	0.2893	0.5930	0.1258	0.073*
C16	0.31355 (12)	0.7171 (5)	0.39060 (7)	0.0619 (6)
H16	0.2822	0.8181	0.3753	0.074*
C6	0.38144 (13)	0.0964 (5)	0.10979 (7)	0.0649 (7)
H6	0.3982	−0.0070	0.0870	0.078*
C5	0.39718 (13)	0.0424 (4)	0.15377 (7)	0.0629 (7)
H5	0.4244	−0.0977	0.1605	0.075*
C15	0.32395 (14)	0.7662 (5)	0.43632 (8)	0.0681 (7)
H15	0.2995	0.8934	0.4509	0.082*
O1W	0.28141 (9)	0.4811 (3)	0.28357 (5)	0.0696 (5)
H1A	0.3792 (14)	0.272 (4)	0.2514 (7)	0.104*
H1WA	0.2599 (13)	0.621 (3)	0.2800 (7)	0.104*
H1WB	0.3043 (12)	0.488 (5)	0.3078 (6)	0.104*

	U11	U22	U33	U12	U13	U23
Cl1	0.0970 (6)	0.1067 (6)	0.0538 (4)	−0.0048 (5)	−0.0072 (3)	0.0087 (4)
O2	0.0583 (10)	0.0571 (10)	0.0443 (8)	0.0109 (8)	−0.0004 (7)	−0.0023 (7)
N2	0.0479 (11)	0.0527 (11)	0.0509 (10)	0.0024 (10)	0.0006 (9)	−0.0023 (9)
N1	0.0637 (13)	0.0479 (12)	0.0455 (11)	0.0084 (10)	0.0035 (9)	−0.0050 (9)
C10	0.0559 (15)	0.0596 (15)	0.0548 (13)	0.0078 (13)	0.0008 (11)	0.0075 (11)
C17	0.0428 (13)	0.0474 (13)	0.0460 (12)	−0.0093 (11)	0.0013 (10)	0.0031 (10)
C13	0.0564 (16)	0.0522 (14)	0.0479 (13)	−0.0131 (12)	0.0007 (11)	0.0020 (11)
C7	0.0553 (15)	0.0433 (13)	0.0533 (13)	−0.0019 (12)	0.0051 (11)	−0.0029 (11)
C9	0.0467 (13)	0.0514 (14)	0.0431 (11)	−0.0045 (11)	0.0017 (10)	0.0048 (10)
C11	0.0607 (17)	0.0717 (17)	0.0618 (15)	0.0002 (14)	−0.0119 (13)	0.0128 (13)
C12	0.0712 (18)	0.0652 (17)	0.0490 (13)	−0.0091 (14)	−0.0092 (13)	0.0060 (12)
C14	0.080 (2)	0.0656 (17)	0.0492 (14)	−0.0122 (15)	0.0029 (13)	−0.0056 (12)
O1	0.1077 (15)	0.0544 (11)	0.0691 (10)	0.0222 (10)	−0.0111 (10)	−0.0142 (9)
C1	0.0581 (16)	0.0621 (16)	0.0490 (13)	−0.0105 (13)	0.0011 (11)	0.0007 (12)
C8	0.0611 (16)	0.0450 (13)	0.0525 (13)	0.0043 (12)	0.0072 (11)	0.0048 (11)
C4	0.0503 (15)	0.0452 (12)	0.0485 (12)	−0.0055 (11)	0.0031 (11)	−0.0035 (10)
C3	0.0629 (16)	0.0520 (14)	0.0558 (14)	0.0068 (13)	−0.0027 (12)	−0.0110 (11)
C2	0.0615 (15)	0.0600 (15)	0.0621 (15)	0.0043 (13)	−0.0094 (13)	−0.0010 (12)
C16	0.0584 (16)	0.0599 (15)	0.0673 (15)	0.0036 (13)	−0.0009 (13)	−0.0050 (13)
C6	0.0829 (19)	0.0631 (16)	0.0486 (14)	0.0028 (15)	0.0136 (13)	−0.0053 (12)
C5	0.0821 (18)	0.0527 (14)	0.0539 (14)	0.0125 (13)	0.0141 (13)	−0.0024 (11)
C15	0.0737 (19)	0.0673 (17)	0.0634 (16)	−0.0007 (15)	0.0090 (14)	−0.0175 (14)
O1W	0.0808 (14)	0.0720 (13)	0.0560 (10)	0.0091 (10)	−0.0059 (9)	−0.0056 (9)

Cl1—C1	1.730 (2)	C14—C15	1.349 (3)
O2—C9	1.363 (2)	C14—H14	0.9300
O2—C8	1.425 (2)	C1—C6	1.365 (3)
N2—C16	1.305 (3)	C1—C2	1.365 (3)
N2—C17	1.358 (2)	C8—H8A	0.9700
N1—C7	1.339 (3)	C8—H8B	0.9700
N1—C4	1.411 (3)	C4—C5	1.377 (3)
N1—H1A	0.832 (10)	C4—C3	1.377 (3)
C10—C9	1.366 (3)	C3—C2	1.379 (3)
C10—C11	1.396 (3)	C3—H3	0.9300
C10—H10	0.9300	C2—H2	0.9300
C17—C13	1.412 (3)	C16—C15	1.404 (3)
C17—C9	1.417 (3)	C16—H16	0.9300
C13—C12	1.400 (3)	C6—C5	1.378 (3)
C13—C14	1.399 (3)	C6—H6	0.9300
C7—O1	1.212 (2)	C5—H5	0.9300
C7—C8	1.494 (3)	C15—H15	0.9300
C11—C12	1.348 (3)	O1W—H1WA	0.854 (9)
C11—H11	0.9300	O1W—H1WB	0.851 (9)
C12—H12	0.9300
C9—O2—C8	115.98 (16)	C6—C1—Cl1	119.91 (18)
C16—N2—C17	117.87 (19)	C2—C1—Cl1	119.9 (2)
C7—N1—C4	126.84 (18)	O2—C8—C7	113.02 (17)
C7—N1—H1A	115.0 (19)	O2—C8—H8A	109.0
C4—N1—H1A	118.2 (19)	C7—C8—H8A	109.0
C9—C10—C11	120.1 (2)	O2—C8—H8B	109.0
C9—C10—H10	119.9	C7—C8—H8B	109.0
C11—C10—H10	119.9	H8A—C8—H8B	107.8
N2—C17—C13	122.04 (19)	C5—C4—C3	118.5 (2)
N2—C17—C9	119.08 (18)	C5—C4—N1	123.7 (2)
C13—C17—C9	118.88 (19)	C3—C4—N1	117.76 (19)
C12—C13—C14	123.1 (2)	C4—C3—C2	121.1 (2)
C12—C13—C17	119.5 (2)	C4—C3—H3	119.5
C14—C13—C17	117.4 (2)	C2—C3—H3	119.5
O1—C7—N1	124.8 (2)	C1—C2—C3	119.6 (2)
O1—C7—C8	116.7 (2)	C1—C2—H2	120.2
N1—C7—C8	118.50 (19)	C3—C2—H2	120.2
O2—C9—C10	124.9 (2)	N2—C16—C15	124.3 (2)
O2—C9—C17	115.25 (18)	N2—C16—H16	117.9
C10—C9—C17	119.84 (19)	C15—C16—H16	117.9
C12—C11—C10	121.5 (2)	C1—C6—C5	120.3 (2)
C12—C11—H11	119.3	C1—C6—H6	119.9
C10—C11—H11	119.3	C5—C6—H6	119.9
C11—C12—C13	120.1 (2)	C4—C5—C6	120.4 (2)
C11—C12—H12	119.9	C4—C5—H5	119.8
C13—C12—H12	119.9	C6—C5—H5	119.8
C15—C14—C13	120.3 (2)	C14—C15—C16	118.2 (2)
C15—C14—H14	119.9	C14—C15—H15	120.9
C13—C14—H14	119.9	C16—C15—H15	120.9
C6—C1—C2	120.2 (2)	H1WA—O1W—H1WB	109.2 (15)
C16—N2—C17—C13	0.5 (3)	C12—C13—C14—C15	178.8 (2)
C16—N2—C17—C9	−179.92 (19)	C17—C13—C14—C15	−1.2 (3)
N2—C17—C13—C12	−179.1 (2)	C9—O2—C8—C7	−175.30 (17)
C9—C17—C13—C12	1.3 (3)	O1—C7—C8—O2	−171.25 (19)
N2—C17—C13—C14	0.9 (3)	N1—C7—C8—O2	10.0 (3)
C9—C17—C13—C14	−178.67 (19)	C7—N1—C4—C5	−10.4 (4)
C4—N1—C7—O1	−4.3 (4)	C7—N1—C4—C3	171.6 (2)
C4—N1—C7—C8	174.31 (19)	C5—C4—C3—C2	−0.2 (3)
C8—O2—C9—C10	6.1 (3)	N1—C4—C3—C2	177.9 (2)
C8—O2—C9—C17	−174.00 (17)	C6—C1—C2—C3	0.1 (3)
C11—C10—C9—O2	−179.4 (2)	Cl1—C1—C2—C3	−179.29 (18)
C11—C10—C9—C17	0.8 (3)	C4—C3—C2—C1	0.0 (3)
N2—C17—C9—O2	−1.3 (3)	C17—N2—C16—C15	−1.7 (3)
C13—C17—C9—O2	178.33 (18)	C2—C1—C6—C5	0.0 (4)
N2—C17—C9—C10	178.64 (19)	Cl1—C1—C6—C5	179.38 (19)
C13—C17—C9—C10	−1.8 (3)	C3—C4—C5—C6	0.3 (3)
C9—C10—C11—C12	0.7 (4)	N1—C4—C5—C6	−177.6 (2)
C10—C11—C12—C13	−1.2 (4)	C1—C6—C5—C4	−0.2 (4)
C14—C13—C12—C11	−179.9 (2)	C13—C14—C15—C16	0.2 (4)
C17—C13—C12—C11	0.1 (3)	N2—C16—C15—C14	1.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1Wi	0.85 (1)	2.06 (1)	2.9014 (16)	168 (2)
N1—H1A···O2	0.83 (1)	2.27 (2)	2.702 (2)	113 (2)
N1—H1A···O1W	0.83 (1)	2.40 (2)	3.088 (2)	140 (2)
O1W—H1WB···N2	0.85 (1)	1.99 (1)	2.830 (2)	170 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O1Wi	0.85 (1)	2.06 (1)	2.9014 (16)	168 (2)
O1W—H1WB⋯N2	0.85 (1)	1.99 (1)	2.830 (2)	170 (2)
N1—H1A⋯O2	0.83 (1)	2.27 (2)	2.702 (2)	113 (2)
N1—H1A⋯O1W	0.83 (1)	2.40 (2)	3.088 (2)	140 (2)

Symmetry code: (i) .