(2E)-3-(4-Eth-oxy-phen-yl)-1-(2-methyl-4-phenyl-quinolin-3-yl)prop-2-en-1-one monohydrate.

The title hydrate, C(27)H(23)NO(2)·H(2)O, features an almost planar quinoline residue (r.m.s. deviation = 0.015 Å) with the benzene [dihedral angle = 63.80 (7) °] and chalcone [C-C-C-O torsion angle = -103.38 (18)°] substituents twisted significantly out of its plane. The configuration about the C=C bond [1.340 (2) Å] is E. In the crystal, mol-ecules related by the 2(1) symmetry operation are linked along the b axis via water mol-ecules that form O-H⋯O(c) and O-H⋯N(q) hydrogen bonds (c = carbonyl and q = quinoline). A C-H⋯O inter-action also occurs.

Related literature

For background to chalcones, see: Schröder et al. (1988 ▶); Schröder & Schröder (1990 ▶). For a related structure, see: Prasath et al. (2010 ▶).

Experimental

Crystal data

C27H23NO2·H2O

M = 411.48

Monoclinic,

a = 17.4256 (4) Å

b = 7.6240 (2) Å

c = 18.4117 (4) Å

β = 116.957 (1)°

V = 2180.27 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.37 × 0.24 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.977, T max = 0.988

29183 measured reflections

4993 independent reflections

3568 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.146

S = 1.05

4993 reflections

288 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048026/hb5746sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048026/hb5746Isup2.hkl

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

C27H23NO2·H2O	F(000) = 872
Mr = 411.48	Dx = 1.254 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9513 reflections
a = 17.4256 (4) Å	θ = 2.2–29.5°
b = 7.6240 (2) Å	µ = 0.08 mm−1
c = 18.4117 (4) Å	T = 293 K
β = 116.957 (1)°	Block, colourless
V = 2180.27 (9) Å3	0.37 × 0.24 × 0.15 mm
Z = 4

Bruker SMART APEX CCD diffractometer	4993 independent reflections
Radiation source: fine-focus sealed tube	3568 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −22→22
Tmin = 0.977, Tmax = 0.988	k = −9→8
29183 measured reflections	l = −18→23

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.065P)2 + 0.6319P] where P = (Fo2 + 2Fc2)/3
4993 reflections	(Δ/σ)max = 0.001
288 parameters	Δρmax = 0.25 e Å−3
3 restraints	Δρmin = −0.19 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.25716 (8)	0.36751 (17)	0.84346 (7)	0.0543 (3)
O2	0.50345 (8)	−0.52976 (18)	1.12587 (8)	0.0590 (4)
N1	−0.02026 (8)	0.1867 (2)	0.72578 (8)	0.0466 (4)
C1	0.06079 (10)	0.1951 (2)	0.78155 (10)	0.0414 (4)
C2	0.12999 (10)	0.2106 (2)	0.76061 (9)	0.0366 (3)
C3	0.11343 (10)	0.2195 (2)	0.67992 (9)	0.0362 (3)
C4	0.02593 (10)	0.2109 (2)	0.61876 (9)	0.0392 (4)
C5	0.00012 (12)	0.2155 (2)	0.53384 (10)	0.0500 (4)
H5	0.0416	0.2274	0.5155	0.060*
C6	−0.08461 (13)	0.2026 (3)	0.47860 (11)	0.0593 (5)
H6	−0.1004	0.2067	0.4231	0.071*
C7	−0.14798 (13)	0.1831 (3)	0.50494 (12)	0.0631 (6)
H7	−0.2055	0.1736	0.4668	0.076*
C8	−0.12593 (12)	0.1781 (3)	0.58612 (12)	0.0574 (5)
H8	−0.1685	0.1649	0.6030	0.069*
C9	−0.03862 (10)	0.1928 (2)	0.64478 (10)	0.0431 (4)
C10	0.07655 (12)	0.1904 (3)	0.86890 (11)	0.0568 (5)
H10A	0.0225	0.1970	0.8709	0.085*
H10B	0.1120	0.2881	0.8978	0.085*
H10C	0.1052	0.0830	0.8937	0.085*
C11	0.18529 (10)	0.2312 (2)	0.65688 (9)	0.0377 (4)
C12	0.19313 (12)	0.3754 (3)	0.61469 (10)	0.0498 (4)
H12	0.1537	0.4668	0.6010	0.060*
C13	0.25941 (13)	0.3837 (3)	0.59282 (12)	0.0581 (5)
H13	0.2642	0.4809	0.5646	0.070*
C14	0.31808 (12)	0.2493 (3)	0.61263 (11)	0.0546 (5)
H14	0.3622	0.2550	0.5975	0.066*
C15	0.31119 (12)	0.1063 (3)	0.65488 (11)	0.0526 (5)
H15	0.3512	0.0160	0.6688	0.063*
C16	0.24500 (11)	0.0957 (2)	0.67697 (10)	0.0449 (4)
H16	0.2406	−0.0018	0.7052	0.054*
C17	0.22121 (10)	0.2250 (2)	0.82790 (9)	0.0378 (4)
C18	0.26143 (10)	0.0642 (2)	0.87161 (9)	0.0434 (4)
H18	0.2325	−0.0415	0.8527	0.052*
C19	0.33811 (10)	0.0620 (2)	0.93782 (9)	0.0401 (4)
H19	0.3659	0.1694	0.9546	0.048*
C20	0.38267 (9)	−0.0908 (2)	0.98645 (9)	0.0375 (4)
C21	0.45460 (10)	−0.0704 (2)	1.06181 (10)	0.0460 (4)
H21	0.4748	0.0422	1.0799	0.055*
C22	0.49672 (11)	−0.2115 (2)	1.11034 (10)	0.0481 (4)
H22	0.5440	−0.1938	1.1607	0.058*
C23	0.46812 (10)	−0.3798 (2)	1.08362 (10)	0.0449 (4)
C24	0.39746 (11)	−0.4039 (3)	1.00726 (11)	0.0519 (4)
H24	0.3786	−0.5167	0.9885	0.062*
C25	0.35586 (10)	−0.2621 (2)	0.95986 (10)	0.0452 (4)
H25	0.3090	−0.2801	0.9092	0.054*
C26	0.57919 (12)	−0.5162 (3)	1.20221 (12)	0.0619 (5)
H26A	0.5673	−0.4477	1.2403	0.074*
H26B	0.6249	−0.4589	1.1948	0.074*
C27	0.60576 (15)	−0.6989 (3)	1.23413 (14)	0.0752 (7)
H27A	0.5606	−0.7532	1.2424	0.113*
H27B	0.6573	−0.6941	1.2850	0.113*
H27C	0.6163	−0.7660	1.1955	0.113*
O1W	0.17008 (10)	0.6955 (2)	0.74149 (10)	0.0673 (4)
H1W	0.1271 (11)	0.701 (3)	0.7493 (17)	0.101*
H2W	0.1963 (15)	0.603 (2)	0.7613 (16)	0.101*

	U11	U22	U33	U12	U13	U23
O1	0.0495 (7)	0.0459 (8)	0.0520 (7)	−0.0053 (6)	0.0095 (6)	0.0020 (6)
O2	0.0491 (7)	0.0527 (8)	0.0566 (8)	0.0010 (6)	0.0077 (6)	0.0129 (6)
N1	0.0380 (7)	0.0570 (10)	0.0438 (8)	0.0002 (7)	0.0177 (6)	−0.0018 (6)
C1	0.0407 (9)	0.0450 (10)	0.0373 (8)	0.0005 (7)	0.0166 (7)	0.0011 (7)
C2	0.0360 (8)	0.0368 (9)	0.0333 (7)	0.0022 (7)	0.0123 (6)	0.0023 (6)
C3	0.0364 (8)	0.0338 (8)	0.0340 (7)	0.0034 (7)	0.0120 (6)	0.0023 (6)
C4	0.0394 (8)	0.0370 (9)	0.0350 (8)	0.0070 (7)	0.0114 (6)	0.0013 (6)
C5	0.0513 (10)	0.0555 (11)	0.0359 (8)	0.0077 (9)	0.0133 (7)	0.0014 (8)
C6	0.0595 (12)	0.0641 (13)	0.0357 (9)	0.0115 (10)	0.0053 (8)	−0.0015 (8)
C7	0.0447 (10)	0.0689 (14)	0.0505 (11)	0.0075 (10)	−0.0003 (8)	−0.0081 (10)
C8	0.0376 (9)	0.0669 (13)	0.0578 (11)	0.0040 (9)	0.0131 (8)	−0.0063 (9)
C9	0.0373 (8)	0.0435 (10)	0.0411 (8)	0.0036 (7)	0.0113 (7)	−0.0020 (7)
C10	0.0536 (11)	0.0788 (14)	0.0414 (9)	−0.0015 (10)	0.0247 (8)	0.0011 (9)
C11	0.0375 (8)	0.0431 (9)	0.0300 (7)	0.0014 (7)	0.0131 (6)	−0.0005 (6)
C12	0.0551 (10)	0.0485 (11)	0.0487 (9)	0.0076 (9)	0.0260 (8)	0.0079 (8)
C13	0.0704 (13)	0.0584 (12)	0.0568 (11)	−0.0030 (10)	0.0385 (10)	0.0072 (9)
C14	0.0504 (10)	0.0673 (13)	0.0540 (10)	−0.0019 (9)	0.0305 (9)	−0.0012 (9)
C15	0.0483 (10)	0.0583 (12)	0.0533 (10)	0.0091 (9)	0.0249 (8)	0.0023 (9)
C16	0.0473 (9)	0.0460 (10)	0.0414 (8)	0.0039 (8)	0.0201 (7)	0.0030 (7)
C17	0.0365 (8)	0.0434 (10)	0.0315 (7)	−0.0022 (7)	0.0137 (6)	0.0000 (6)
C18	0.0396 (9)	0.0433 (10)	0.0401 (8)	−0.0018 (7)	0.0117 (7)	0.0023 (7)
C19	0.0386 (8)	0.0429 (9)	0.0374 (8)	−0.0005 (7)	0.0162 (7)	−0.0025 (7)
C20	0.0315 (7)	0.0447 (9)	0.0347 (7)	0.0003 (7)	0.0135 (6)	−0.0008 (6)
C21	0.0390 (9)	0.0470 (10)	0.0422 (9)	−0.0037 (8)	0.0097 (7)	−0.0062 (7)
C22	0.0356 (8)	0.0574 (12)	0.0385 (8)	−0.0015 (8)	0.0056 (7)	−0.0011 (8)
C23	0.0363 (8)	0.0500 (11)	0.0446 (9)	0.0040 (8)	0.0151 (7)	0.0097 (8)
C24	0.0460 (10)	0.0439 (10)	0.0512 (10)	−0.0048 (8)	0.0093 (8)	0.0008 (8)
C25	0.0350 (8)	0.0509 (11)	0.0384 (8)	−0.0032 (7)	0.0067 (7)	−0.0016 (7)
C26	0.0471 (10)	0.0639 (13)	0.0558 (11)	0.0048 (10)	0.0067 (8)	0.0130 (10)
C27	0.0647 (13)	0.0706 (16)	0.0712 (14)	0.0141 (12)	0.0139 (11)	0.0229 (12)
O1W	0.0615 (9)	0.0736 (11)	0.0734 (10)	−0.0010 (8)	0.0363 (8)	0.0040 (8)

O1—C17	1.222 (2)	C13—H13	0.9300
O2—C23	1.363 (2)	C14—C15	1.375 (3)
O2—C26	1.430 (2)	C14—H14	0.9300
N1—C1	1.318 (2)	C15—C16	1.388 (2)
N1—C9	1.377 (2)	C15—H15	0.9300
C1—C2	1.428 (2)	C16—H16	0.9300
C1—C10	1.504 (2)	C17—C18	1.460 (2)
C2—C3	1.381 (2)	C18—C19	1.340 (2)
C2—C17	1.513 (2)	C18—H18	0.9300
C3—C4	1.428 (2)	C19—C20	1.460 (2)
C3—C11	1.496 (2)	C19—H19	0.9300
C4—C9	1.415 (2)	C20—C21	1.394 (2)
C4—C5	1.418 (2)	C20—C25	1.398 (2)
C5—C6	1.365 (3)	C21—C22	1.379 (2)
C5—H5	0.9300	C21—H21	0.9300
C6—C7	1.401 (3)	C22—C23	1.383 (3)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.365 (3)	C23—C24	1.399 (2)
C7—H7	0.9300	C24—C25	1.372 (2)
C8—C9	1.416 (2)	C24—H24	0.9300
C8—H8	0.9300	C25—H25	0.9300
C10—H10A	0.9600	C26—C27	1.501 (3)
C10—H10B	0.9600	C26—H26A	0.9700
C10—H10C	0.9600	C26—H26B	0.9700
C11—C12	1.388 (2)	C27—H27A	0.9600
C11—C16	1.392 (2)	C27—H27B	0.9600
C12—C13	1.386 (3)	C27—H27C	0.9600
C12—H12	0.9300	O1W—H1W	0.83 (2)
C13—C14	1.375 (3)	O1W—H2W	0.83 (2)
C23—O2—C26	118.49 (15)	C14—C15—C16	120.59 (17)
C1—N1—C9	118.87 (14)	C14—C15—H15	119.7
N1—C1—C2	122.10 (14)	C16—C15—H15	119.7
N1—C1—C10	116.33 (15)	C15—C16—C11	119.96 (16)
C2—C1—C10	121.56 (14)	C15—C16—H16	120.0
C3—C2—C1	120.30 (14)	C11—C16—H16	120.0
C3—C2—C17	120.48 (14)	O1—C17—C18	123.42 (14)
C1—C2—C17	119.18 (13)	O1—C17—C2	119.56 (14)
C2—C3—C4	118.28 (14)	C18—C17—C2	117.02 (14)
C2—C3—C11	120.97 (13)	C19—C18—C17	122.91 (16)
C4—C3—C11	120.72 (13)	C19—C18—H18	118.5
C9—C4—C5	118.18 (15)	C17—C18—H18	118.5
C9—C4—C3	117.77 (14)	C18—C19—C20	126.98 (16)
C5—C4—C3	124.04 (15)	C18—C19—H19	116.5
C6—C5—C4	121.01 (18)	C20—C19—H19	116.5
C6—C5—H5	119.5	C21—C20—C25	117.36 (15)
C4—C5—H5	119.5	C21—C20—C19	120.63 (15)
C5—C6—C7	120.40 (17)	C25—C20—C19	122.01 (14)
C5—C6—H6	119.8	C22—C21—C20	122.15 (16)
C7—C6—H6	119.8	C22—C21—H21	118.9
C8—C7—C6	120.50 (17)	C20—C21—H21	118.9
C8—C7—H7	119.8	C21—C22—C23	119.56 (15)
C6—C7—H7	119.8	C21—C22—H22	120.2
C7—C8—C9	120.31 (18)	C23—C22—H22	120.2
C7—C8—H8	119.8	O2—C23—C22	125.33 (15)
C9—C8—H8	119.8	O2—C23—C24	115.31 (16)
N1—C9—C4	122.67 (14)	C22—C23—C24	119.35 (15)
N1—C9—C8	117.72 (16)	C25—C24—C23	120.42 (17)
C4—C9—C8	119.60 (16)	C25—C24—H24	119.8
C1—C10—H10A	109.5	C23—C24—H24	119.8
C1—C10—H10B	109.5	C24—C25—C20	121.12 (15)
H10A—C10—H10B	109.5	C24—C25—H25	119.4
C1—C10—H10C	109.5	C20—C25—H25	119.4
H10A—C10—H10C	109.5	O2—C26—C27	107.53 (18)
H10B—C10—H10C	109.5	O2—C26—H26A	110.2
C12—C11—C16	119.01 (15)	C27—C26—H26A	110.2
C12—C11—C3	120.88 (15)	O2—C26—H26B	110.2
C16—C11—C3	120.11 (14)	C27—C26—H26B	110.2
C13—C12—C11	120.36 (17)	H26A—C26—H26B	108.5
C13—C12—H12	119.8	C26—C27—H27A	109.5
C11—C12—H12	119.8	C26—C27—H27B	109.5
C14—C13—C12	120.38 (18)	H27A—C27—H27B	109.5
C14—C13—H13	119.8	C26—C27—H27C	109.5
C12—C13—H13	119.8	H27A—C27—H27C	109.5
C13—C14—C15	119.71 (17)	H27B—C27—H27C	109.5
C13—C14—H14	120.1	H1W—O1W—H2W	109.0 (18)
C15—C14—H14	120.1
C9—N1—C1—C2	0.1 (3)	C16—C11—C12—C13	0.1 (3)
C9—N1—C1—C10	179.15 (16)	C3—C11—C12—C13	−179.23 (16)
N1—C1—C2—C3	0.8 (3)	C11—C12—C13—C14	0.0 (3)
C10—C1—C2—C3	−178.20 (17)	C12—C13—C14—C15	−0.5 (3)
N1—C1—C2—C17	178.19 (15)	C13—C14—C15—C16	0.7 (3)
C10—C1—C2—C17	−0.8 (2)	C14—C15—C16—C11	−0.5 (3)
C1—C2—C3—C4	−0.7 (2)	C12—C11—C16—C15	0.1 (2)
C17—C2—C3—C4	−178.00 (14)	C3—C11—C16—C15	179.46 (15)
C1—C2—C3—C11	−178.44 (15)	C3—C2—C17—O1	74.0 (2)
C17—C2—C3—C11	4.2 (2)	C1—C2—C17—O1	−103.38 (18)
C2—C3—C4—C9	−0.3 (2)	C3—C2—C17—C18	−106.50 (18)
C11—C3—C4—C9	177.47 (15)	C1—C2—C17—C18	76.12 (19)
C2—C3—C4—C5	−178.84 (16)	O1—C17—C18—C19	6.8 (3)
C11—C3—C4—C5	−1.1 (2)	C2—C17—C18—C19	−172.70 (15)
C9—C4—C5—C6	−0.1 (3)	C17—C18—C19—C20	178.70 (15)
C3—C4—C5—C6	178.44 (17)	C18—C19—C20—C21	−168.50 (16)
C4—C5—C6—C7	−0.5 (3)	C18—C19—C20—C25	11.8 (3)
C5—C6—C7—C8	0.5 (3)	C25—C20—C21—C22	−2.2 (3)
C6—C7—C8—C9	0.1 (3)	C19—C20—C21—C22	178.11 (16)
C1—N1—C9—C4	−1.1 (3)	C20—C21—C22—C23	1.0 (3)
C1—N1—C9—C8	178.07 (17)	C26—O2—C23—C22	−3.7 (3)
C5—C4—C9—N1	179.87 (16)	C26—O2—C23—C24	176.17 (16)
C3—C4—C9—N1	1.3 (2)	C21—C22—C23—O2	−179.40 (17)
C5—C4—C9—C8	0.7 (2)	C21—C22—C23—C24	0.8 (3)
C3—C4—C9—C8	−177.95 (16)	O2—C23—C24—C25	178.97 (16)
C7—C8—C9—N1	−179.94 (19)	C22—C23—C24—C25	−1.2 (3)
C7—C8—C9—C4	−0.7 (3)	C23—C24—C25—C20	−0.1 (3)
C2—C3—C11—C12	−118.53 (18)	C21—C20—C25—C24	1.7 (3)
C4—C3—C11—C12	63.7 (2)	C19—C20—C25—C24	−178.55 (16)
C2—C3—C11—C16	62.1 (2)	C23—O2—C26—C27	−178.30 (17)
C4—C3—C11—C16	−115.62 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···N1i	0.83 (2)	2.11 (2)	2.934 (2)	174 (2)
O1w—H2w···O1	0.83 (2)	2.28 (2)	3.082 (2)	164 (3)
C26—H26b···O1ii	0.97	2.55	3.507 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w⋯N1i	0.83 (2)	2.11 (2)	2.934 (2)	174 (2)
O1w—H2w⋯O1	0.83 (2)	2.28 (2)	3.082 (2)	164 (3)
C26—H26b⋯O1ii	0.97	2.55	3.507 (3)	167

Symmetry codes: (i) ; (ii) .