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

The title hydrate, C(26)H(21)NO·H(2)O, exhibits significant twists of the benzene ring [dihedral angle = 87.24 (6)°] and chalcone residue [C-C-C-C torsion angle = -94.46 (17)°] out of the plane through the quinoline ring system. The conformation about the C=C bond [1.341 (2) Å] is E. The solvent water mol-ecule forms hydrogen bonds to carbonyl O and quinoline N atoms derived from two mol-ecules and through the application of a centre of inversion, a 16-membered {⋯HOH⋯OC(3)N}(2) synthon is formed to stabilize the resulting tetra-meric (two organic mol-ecules plus two water mol-ecules) aggregate. These are connected into a two-dimensional array via two C-H⋯O contacts, also involving the water mol-ecule. The layers stack along the c axis, being linked by C-H⋯π inter-actions.

Related literature

For background to chalcones, see: Prasath et al. (2010 ▶); Roman (2004 ▶).

Experimental

Crystal data

C26H21NO·H2O

M = 381.45

Triclinic,

a = 8.2634 (7) Å

b = 9.0785 (7) Å

c = 14.1176 (12) Å

α = 91.137 (1)°

β = 101.537 (1)°

γ = 100.820 (1)°

V = 1017.43 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.794, T max = 0.862

9738 measured reflections

4647 independent reflections

3790 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.165

S = 1.01

4647 reflections

270 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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/S1600536810038791/hb5655sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038791/hb5655Isup2.hkl

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

C26H21NO·H2O	Z = 2
Mr = 381.45	F(000) = 404
Triclinic, P1	Dx = 1.245 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2634 (7) Å	Cell parameters from 4003 reflections
b = 9.0785 (7) Å	θ = 2.3–28.3°
c = 14.1176 (12) Å	µ = 0.08 mm−1
α = 91.137 (1)°	T = 100 K
β = 101.537 (1)°	Block, colourless
γ = 100.820 (1)°	0.30 × 0.25 × 0.20 mm
V = 1017.43 (15) Å3

Bruker SMART APEX CCD diffractometer	4647 independent reflections
Radiation source: fine-focus sealed tube	3790 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.794, Tmax = 0.862	k = −11→11
9738 measured reflections	l = −18→18

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.1041P)2 + 0.3702P] where P = (Fo2 + 2Fc2)/3
4647 reflections	(Δ/σ)max = 0.001
270 parameters	Δρmax = 0.35 e Å−3
3 restraints	Δρmin = −0.27 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	0.94050 (14)	0.59600 (13)	0.73474 (8)	0.0254 (3)
O1W	1.28132 (15)	0.67478 (13)	0.84124 (8)	0.0250 (3)
H1W	1.1758 (13)	0.660 (2)	0.8172 (15)	0.037*
H2W	1.280 (3)	0.623 (2)	0.8910 (11)	0.037*
N1	0.74421 (16)	0.53267 (14)	1.00612 (9)	0.0196 (3)
C1	0.71971 (18)	0.67293 (16)	1.03036 (10)	0.0177 (3)
C2	0.6977 (2)	0.70135 (18)	1.12519 (11)	0.0224 (3)
H2	0.6987	0.6239	1.1695	0.027*
C3	0.6751 (2)	0.83978 (18)	1.15372 (11)	0.0232 (3)
H3	0.6601	0.8577	1.2176	0.028*
C4	0.67398 (19)	0.95613 (17)	1.08882 (11)	0.0227 (3)
H4	0.6585	1.0519	1.1092	0.027*
C5	0.69517 (19)	0.93110 (17)	0.99649 (11)	0.0196 (3)
H5	0.6947	1.0101	0.9533	0.024*
C6	0.71780 (17)	0.78851 (16)	0.96457 (10)	0.0169 (3)
C7	0.73952 (17)	0.75512 (16)	0.86916 (10)	0.0166 (3)
C8	0.76569 (18)	0.61495 (16)	0.84716 (10)	0.0169 (3)
C9	0.76789 (18)	0.50488 (17)	0.91867 (11)	0.0190 (3)
C10	0.8000 (2)	0.35126 (17)	0.89604 (12)	0.0245 (3)
H10A	0.8047	0.2937	0.9542	0.037*
H10B	0.9073	0.3616	0.8749	0.037*
H10C	0.7087	0.2987	0.8443	0.037*
C11	0.73297 (18)	0.87247 (16)	0.79625 (10)	0.0173 (3)
C12	0.88036 (19)	0.96807 (17)	0.78550 (11)	0.0214 (3)
H12	0.9857	0.9572	0.8235	0.026*
C13	0.8738 (2)	1.07962 (17)	0.71923 (12)	0.0232 (3)
H13	0.9745	1.1449	0.7123	0.028*
C14	0.7202 (2)	1.09540 (17)	0.66338 (11)	0.0218 (3)
H14	0.7157	1.1709	0.6178	0.026*
C15	0.5731 (2)	1.00064 (17)	0.67422 (11)	0.0225 (3)
H15	0.4680	1.0117	0.6360	0.027*
C16	0.57866 (19)	0.88978 (17)	0.74058 (11)	0.0197 (3)
H16	0.4775	0.8258	0.7481	0.024*
C17	0.79675 (18)	0.57226 (16)	0.74902 (11)	0.0179 (3)
C18	0.65484 (19)	0.49748 (16)	0.67431 (10)	0.0189 (3)
H18	0.6776	0.4576	0.6167	0.023*
C19	0.49390 (19)	0.48223 (16)	0.68281 (10)	0.0181 (3)
H19	0.4744	0.5264	0.7400	0.022*
C20	0.34572 (18)	0.40472 (16)	0.61317 (10)	0.0177 (3)
C21	0.18670 (19)	0.42552 (17)	0.62322 (11)	0.0203 (3)
H21	0.1774	0.4912	0.6742	0.024*
C22	0.04245 (19)	0.35188 (17)	0.56003 (11)	0.0215 (3)
H22	−0.0642	0.3687	0.5680	0.026*
C23	0.0509 (2)	0.25349 (17)	0.48501 (11)	0.0221 (3)
C24	0.2101 (2)	0.23307 (18)	0.47450 (11)	0.0227 (3)
H24	0.2189	0.1672	0.4235	0.027*
C25	0.3546 (2)	0.30677 (17)	0.53679 (11)	0.0216 (3)
H25	0.4613	0.2912	0.5280	0.026*
C26	−0.1064 (2)	0.1710 (2)	0.41757 (12)	0.0291 (4)
H26A	−0.2011	0.2191	0.4232	0.044*
H26B	−0.1308	0.0663	0.4348	0.044*
H26C	−0.0898	0.1740	0.3508	0.044*

	U11	U22	U33	U12	U13	U23
O1	0.0202 (6)	0.0342 (6)	0.0227 (6)	0.0050 (5)	0.0068 (4)	0.0002 (5)
O1W	0.0252 (6)	0.0248 (6)	0.0232 (6)	0.0007 (5)	0.0042 (5)	0.0061 (5)
N1	0.0217 (6)	0.0181 (6)	0.0185 (6)	0.0030 (5)	0.0040 (5)	0.0034 (5)
C1	0.0155 (7)	0.0191 (7)	0.0176 (7)	0.0021 (5)	0.0027 (5)	0.0008 (5)
C2	0.0230 (8)	0.0263 (8)	0.0182 (7)	0.0046 (6)	0.0050 (6)	0.0045 (6)
C3	0.0219 (7)	0.0295 (8)	0.0183 (7)	0.0039 (6)	0.0058 (6)	−0.0025 (6)
C4	0.0209 (7)	0.0224 (7)	0.0238 (8)	0.0052 (6)	0.0022 (6)	−0.0046 (6)
C5	0.0190 (7)	0.0184 (7)	0.0209 (7)	0.0040 (5)	0.0027 (6)	0.0013 (6)
C6	0.0143 (6)	0.0183 (7)	0.0169 (7)	0.0021 (5)	0.0013 (5)	0.0006 (5)
C7	0.0120 (6)	0.0180 (7)	0.0184 (7)	0.0015 (5)	0.0013 (5)	0.0017 (5)
C8	0.0145 (6)	0.0191 (7)	0.0162 (7)	0.0020 (5)	0.0021 (5)	0.0007 (5)
C9	0.0187 (7)	0.0185 (7)	0.0184 (7)	0.0029 (5)	0.0015 (5)	0.0004 (5)
C10	0.0328 (9)	0.0195 (7)	0.0225 (8)	0.0081 (6)	0.0056 (6)	0.0026 (6)
C11	0.0203 (7)	0.0168 (7)	0.0150 (7)	0.0044 (5)	0.0039 (5)	0.0007 (5)
C12	0.0169 (7)	0.0242 (7)	0.0208 (7)	0.0013 (6)	0.0010 (6)	0.0024 (6)
C13	0.0230 (8)	0.0205 (7)	0.0245 (8)	−0.0021 (6)	0.0071 (6)	0.0021 (6)
C14	0.0287 (8)	0.0177 (7)	0.0204 (7)	0.0054 (6)	0.0072 (6)	0.0053 (6)
C15	0.0203 (7)	0.0243 (8)	0.0231 (8)	0.0069 (6)	0.0020 (6)	0.0039 (6)
C16	0.0166 (7)	0.0205 (7)	0.0217 (7)	0.0024 (5)	0.0042 (6)	0.0032 (6)
C17	0.0196 (7)	0.0165 (7)	0.0190 (7)	0.0055 (5)	0.0053 (6)	0.0027 (5)
C18	0.0230 (7)	0.0190 (7)	0.0156 (7)	0.0053 (6)	0.0047 (6)	0.0005 (5)
C19	0.0221 (7)	0.0184 (7)	0.0146 (7)	0.0054 (6)	0.0040 (6)	0.0008 (5)
C20	0.0204 (7)	0.0176 (7)	0.0157 (7)	0.0042 (5)	0.0042 (5)	0.0036 (5)
C21	0.0233 (8)	0.0210 (7)	0.0186 (7)	0.0054 (6)	0.0077 (6)	0.0021 (6)
C22	0.0207 (7)	0.0242 (7)	0.0213 (7)	0.0044 (6)	0.0077 (6)	0.0058 (6)
C23	0.0228 (8)	0.0212 (7)	0.0204 (7)	0.0007 (6)	0.0034 (6)	0.0047 (6)
C24	0.0250 (8)	0.0237 (7)	0.0186 (7)	0.0046 (6)	0.0035 (6)	−0.0024 (6)
C25	0.0211 (7)	0.0238 (7)	0.0211 (7)	0.0072 (6)	0.0047 (6)	−0.0005 (6)
C26	0.0249 (8)	0.0316 (9)	0.0265 (8)	−0.0012 (7)	0.0016 (7)	0.0009 (7)

O1—C17	1.2245 (18)	C12—H12	0.9500
O1W—H1W	0.854 (10)	C13—C14	1.388 (2)
O1W—H2W	0.852 (9)	C13—H13	0.9500
N1—C9	1.3149 (19)	C14—C15	1.389 (2)
N1—C1	1.3736 (18)	C14—H14	0.9500
C1—C2	1.412 (2)	C15—C16	1.389 (2)
C1—C6	1.415 (2)	C15—H15	0.9500
C2—C3	1.369 (2)	C16—H16	0.9500
C2—H2	0.9500	C17—C18	1.458 (2)
C3—C4	1.412 (2)	C18—C19	1.341 (2)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.370 (2)	C19—C20	1.459 (2)
C4—H4	0.9500	C19—H19	0.9500
C5—C6	1.4196 (19)	C20—C21	1.396 (2)
C5—H5	0.9500	C20—C25	1.406 (2)
C6—C7	1.428 (2)	C21—C22	1.384 (2)
C7—C8	1.370 (2)	C21—H21	0.9500
C7—C11	1.497 (2)	C22—C23	1.393 (2)
C8—C9	1.434 (2)	C22—H22	0.9500
C8—C17	1.5146 (19)	C23—C24	1.398 (2)
C9—C10	1.507 (2)	C23—C26	1.506 (2)
C10—H10A	0.9800	C24—C25	1.380 (2)
C10—H10B	0.9800	C24—H24	0.9500
C10—H10C	0.9800	C25—H25	0.9500
C11—C12	1.394 (2)	C26—H26A	0.9800
C11—C16	1.396 (2)	C26—H26B	0.9800
C12—C13	1.394 (2)	C26—H26C	0.9800
H1W—O1W—H2W	100 (2)	C12—C13—H13	120.0
C9—N1—C1	118.81 (13)	C13—C14—C15	119.89 (14)
N1—C1—C2	117.92 (13)	C13—C14—H14	120.1
N1—C1—C6	122.51 (13)	C15—C14—H14	120.1
C2—C1—C6	119.57 (13)	C14—C15—C16	120.39 (14)
C3—C2—C1	120.42 (15)	C14—C15—H15	119.8
C3—C2—H2	119.8	C16—C15—H15	119.8
C1—C2—H2	119.8	C15—C16—C11	119.95 (14)
C2—C3—C4	120.46 (14)	C15—C16—H16	120.0
C2—C3—H3	119.8	C11—C16—H16	120.0
C4—C3—H3	119.8	O1—C17—C18	121.12 (13)
C5—C4—C3	120.12 (14)	O1—C17—C8	119.76 (13)
C5—C4—H4	119.9	C18—C17—C8	119.07 (12)
C3—C4—H4	119.9	C19—C18—C17	123.29 (13)
C4—C5—C6	120.74 (14)	C19—C18—H18	118.4
C4—C5—H5	119.6	C17—C18—H18	118.4
C6—C5—H5	119.6	C18—C19—C20	126.63 (13)
C1—C6—C5	118.69 (13)	C18—C19—H19	116.7
C1—C6—C7	117.89 (13)	C20—C19—H19	116.7
C5—C6—C7	123.41 (13)	C21—C20—C25	117.89 (14)
C8—C7—C6	118.43 (13)	C21—C20—C19	119.03 (13)
C8—C7—C11	121.85 (13)	C25—C20—C19	123.06 (13)
C6—C7—C11	119.71 (12)	C22—C21—C20	121.01 (13)
C7—C8—C9	120.04 (13)	C22—C21—H21	119.5
C7—C8—C17	121.83 (13)	C20—C21—H21	119.5
C9—C8—C17	118.12 (12)	C21—C22—C23	121.16 (14)
N1—C9—C8	122.29 (13)	C21—C22—H22	119.4
N1—C9—C10	117.14 (13)	C23—C22—H22	119.4
C8—C9—C10	120.57 (13)	C22—C23—C24	117.93 (14)
C9—C10—H10A	109.5	C22—C23—C26	121.08 (14)
C9—C10—H10B	109.5	C24—C23—C26	120.99 (14)
H10A—C10—H10B	109.5	C25—C24—C23	121.28 (14)
C9—C10—H10C	109.5	C25—C24—H24	119.4
H10A—C10—H10C	109.5	C23—C24—H24	119.4
H10B—C10—H10C	109.5	C24—C25—C20	120.72 (14)
C12—C11—C16	119.54 (14)	C24—C25—H25	119.6
C12—C11—C7	120.23 (13)	C20—C25—H25	119.6
C16—C11—C7	120.21 (13)	C23—C26—H26A	109.5
C11—C12—C13	120.23 (14)	C23—C26—H26B	109.5
C11—C12—H12	119.9	H26A—C26—H26B	109.5
C13—C12—H12	119.9	C23—C26—H26C	109.5
C14—C13—C12	120.00 (14)	H26A—C26—H26C	109.5
C14—C13—H13	120.0	H26B—C26—H26C	109.5
C9—N1—C1—C2	−178.81 (14)	C8—C7—C11—C16	94.05 (17)
C9—N1—C1—C6	0.4 (2)	C6—C7—C11—C16	−85.84 (17)
N1—C1—C2—C3	179.12 (14)	C16—C11—C12—C13	−0.4 (2)
C6—C1—C2—C3	−0.2 (2)	C7—C11—C12—C13	−178.49 (13)
C1—C2—C3—C4	−0.2 (2)	C11—C12—C13—C14	−0.3 (2)
C2—C3—C4—C5	0.2 (2)	C12—C13—C14—C15	0.5 (2)
C3—C4—C5—C6	0.3 (2)	C13—C14—C15—C16	−0.1 (2)
N1—C1—C6—C5	−178.69 (13)	C14—C15—C16—C11	−0.5 (2)
C2—C1—C6—C5	0.6 (2)	C12—C11—C16—C15	0.7 (2)
N1—C1—C6—C7	1.1 (2)	C7—C11—C16—C15	178.87 (13)
C2—C1—C6—C7	−179.66 (13)	C7—C8—C17—O1	88.14 (18)
C4—C5—C6—C1	−0.6 (2)	C9—C8—C17—O1	−90.49 (17)
C4—C5—C6—C7	179.62 (14)	C7—C8—C17—C18	−94.46 (17)
C1—C6—C7—C8	−1.8 (2)	C9—C8—C17—C18	86.91 (17)
C5—C6—C7—C8	177.97 (13)	O1—C17—C18—C19	−173.19 (14)
C1—C6—C7—C11	178.09 (13)	C8—C17—C18—C19	9.4 (2)
C5—C6—C7—C11	−2.1 (2)	C17—C18—C19—C20	−177.71 (13)
C6—C7—C8—C9	1.1 (2)	C18—C19—C20—C21	−166.79 (15)
C11—C7—C8—C9	−178.82 (13)	C18—C19—C20—C25	14.5 (2)
C6—C7—C8—C17	−177.54 (13)	C25—C20—C21—C22	0.1 (2)
C11—C7—C8—C17	2.6 (2)	C19—C20—C21—C22	−178.68 (13)
C1—N1—C9—C8	−1.3 (2)	C20—C21—C22—C23	0.7 (2)
C1—N1—C9—C10	178.05 (13)	C21—C22—C23—C24	−1.0 (2)
C7—C8—C9—N1	0.5 (2)	C21—C22—C23—C26	178.73 (14)
C17—C8—C9—N1	179.17 (13)	C22—C23—C24—C25	0.6 (2)
C7—C8—C9—C10	−178.78 (14)	C26—C23—C24—C25	−179.16 (15)
C17—C8—C9—C10	−0.1 (2)	C23—C24—C25—C20	0.2 (2)
C8—C7—C11—C12	−87.84 (18)	C21—C20—C25—C24	−0.5 (2)
C6—C7—C11—C12	92.27 (17)	C19—C20—C25—C24	178.20 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···O1	0.854 (10)	2.029 (11)	2.8654 (17)	166 (2)
O1w—H2w···N1i	0.852 (9)	2.061 (10)	2.9032 (17)	170 (2)
C4—H4···O1wii	0.95	2.49	3.4055 (19)	161
C16—H16···O1wiii	0.95	2.52	3.402 (2)	155
C24—H24···Cg1iv	0.95	2.70	3.6414 (17)	171

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w⋯O1	0.85 (1)	2.03 (1)	2.8654 (17)	166 (2)
O1w—H2w⋯N1i	0.85 (1)	2.06 (1)	2.9032 (17)	170 (2)
C4—H4⋯O1wii	0.95	2.49	3.4055 (19)	161
C16—H16⋯O1wiii	0.95	2.52	3.402 (2)	155
C24—H24⋯Cg1iv	0.95	2.70	3.6414 (17)	171

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .