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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Pages o2710-o2711
https://doi.org/10.1107/S1600536810038791

(2E)-3-(4-Methyl­phen­yl)-1-(2-methyl-4-phenyl­quinolin-3-yl)prop-2-en-1-one monohydrate

R. Prasath,a S. Sarveswari,a V. Vijayakumar,a‡ Seik Weng Ngb and Edward R. T. Tiekinkb*

aOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com

(Received 27 September 2010; accepted 28 September 2010; online 2 October 2010)

The title hydrate, C26H21NO·H2O, 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 mol­ecule forms hydrogen bonds to carbonyl O and quinoline N atoms derived from two mol­ecules and through the application of a centre of inversion, a 16-membered {⋯HOH⋯OC3N}2 synthon is formed to stabilize the resulting tetra­meric (two organic mol­ecules plus two water mol­ecules) aggregate. These are connected into a two-dimensional array via two C—H⋯O contacts, also involving the water mol­ecule. The layers stack along the c axis, being linked by C—H⋯π inter­actions.

Related literature

For background to chalcones, see: Prasath et al. (2010[Prasath, R., Sarveswari, S., Vijayakumar, V., Narasimhamurthy, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1110.]); Roman (2004[Roman, G. (2004). Acta Chim. Slov. 51, 537-544.]).

[Scheme 1]

Experimental

Crystal data

  • C26H21NO·H2O

  • Mr = 381.45

  • Triclinic, [P \overline 1]

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.794, Tmax = 0.862

  • 9738 measured reflections

  • 4647 independent reflections

  • 3790 reflections with I > 2σ(I)

  • Rint = 0.023
Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 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

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) -x+2, -y+1, -z+2; (ii) -x+2, -y+2, -z+2; (iii) x-1, y, z; (iv) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810038791/hb5655sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810038791/hb5655Isup2.hkl

checkCIF report


Comment top

Chalcones and their corresponding heterocyclic analogues are valuable intermediates in organic synthesis and exhibit a multitude of biological activities. From a chemical point of view, an important feature of chalcones and their analogues is their ability to act as activated unsaturated systems in conjugated addition reactions of carbanions in the presence of basic catalysts (Roman, 2004). In continuation of our interest in the synthesis and crystallographic analysis of chalcones (Prasath et al., 2010), herein we report the structure of a new chalcone derivative isolated as an hydrate, (I).

With reference to the quinolinyl residue (r.m.s. deviation = 0.014 Å), the benzene ring is almost normal, forming a dihedral angle of 87.24 (6) °. The chalcone residue also occupies a position normal to the quinolinyl group as seen in the value of the C7—C8—C17—C18 torsion angle of -94.46 (17) °. The conformation about the C18═C19 double bond [1.341 (2) Å] is E. Small twists are seen in the 4-methylphenyl)prop-2-en-1-one group so that while the expected planar arrangement is seen around the double bond [C17—C18—C19—C20 = -177.71 (13) °], the terminal benzene ring is twisted out of the plane [C18—C19—C20—C21 = -166.79 (15) °].

As anticipated, the water molecule plays a pivotal role in arranging molecules in the crystal packing. Two centrosymmetrically related water molecules link two organic molecules by forming hydrogen bonds to carbonyl-O and quinolinyl-N atoms, Table 1. In this way a 16-membered {···HOH···OC3N}2 synthon is formed, Fig. 2. These are connected into a supramolecular layer in the ab plane via two C—H···O contacts where the water-O accepts these interactions, Fig. 3 and Table 1. Layers stack along the c axis, being connected by C—H···π interactions, Fig. 4 and Table 1.

Related literature top

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

Experimental top

A mixture of 3-acetyl-2-methyl-4-phenylquinoline (2.6 g, 0.01 mmol), 4-methylbenzaldehyde (1.2 g, 0.01 mmol) and a catalytic amount of KOH was stirred in distilled ethanol (25 ml) for about 12 h. The resulting mixture was concentrated to remove ethanol, then poured on to ice and neutralized with dilute acetic acid. The resultant solid was filtered, dried and purified by column chromatography using an 1:1 mixture of ethyl acetate and petroleum ether. Re-crystallization was by slow evaporation of an acetone solution of (I) which yielded colourless crystals; Yield: 64%, M.pt. 412–414 K.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 to 1.5Uequiv(C). The O-bound H atoms were refined with the distance restraint O—H = 0.84±0.1 Å, and with Uiso(H) = 1.5Uequiv(O). In the final refinement a low angle reflection evidently effected by the beam stop was omitted, i.e. (0 0 1).

Structure description top

Chalcones and their corresponding heterocyclic analogues are valuable intermediates in organic synthesis and exhibit a multitude of biological activities. From a chemical point of view, an important feature of chalcones and their analogues is their ability to act as activated unsaturated systems in conjugated addition reactions of carbanions in the presence of basic catalysts (Roman, 2004). In continuation of our interest in the synthesis and crystallographic analysis of chalcones (Prasath et al., 2010), herein we report the structure of a new chalcone derivative isolated as an hydrate, (I).

With reference to the quinolinyl residue (r.m.s. deviation = 0.014 Å), the benzene ring is almost normal, forming a dihedral angle of 87.24 (6) °. The chalcone residue also occupies a position normal to the quinolinyl group as seen in the value of the C7—C8—C17—C18 torsion angle of -94.46 (17) °. The conformation about the C18═C19 double bond [1.341 (2) Å] is E. Small twists are seen in the 4-methylphenyl)prop-2-en-1-one group so that while the expected planar arrangement is seen around the double bond [C17—C18—C19—C20 = -177.71 (13) °], the terminal benzene ring is twisted out of the plane [C18—C19—C20—C21 = -166.79 (15) °].

As anticipated, the water molecule plays a pivotal role in arranging molecules in the crystal packing. Two centrosymmetrically related water molecules link two organic molecules by forming hydrogen bonds to carbonyl-O and quinolinyl-N atoms, Table 1. In this way a 16-membered {···HOH···OC3N}2 synthon is formed, Fig. 2. These are connected into a supramolecular layer in the ab plane via two C—H···O contacts where the water-O accepts these interactions, Fig. 3 and Table 1. Layers stack along the c axis, being connected by C—H···π interactions, Fig. 4 and Table 1.

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

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) showing displacement ellipsoids at the 50% probability level. The O—H···O hydrogen bond is shown as a dashed line.
[Figure 2] Fig. 2. Tetrameric aggregate in (I) sustained by O—H···O, N hydrogen bonds shown as orange dashed lines.
[Figure 3] Fig. 3. Supramolecular array in the ab plane. The O—H···O, N hydrogen bonds and C—H···O interactions are shown as orange and blue dashed lines, respectively. Hydrogen atoms not participating in interactions to stabilize the array have been omitted for clarity.
[Figure 4] Fig. 4. Unit-cell contents for (I) viewed in projection along the a axis showing the stacking of layers along the c axis. The O—H···O, N hydrogen bonds and C—H···O and C—H···π contacts are shown as orange, blue and purple dashed lines, respectively.
(2E)-3-(4-Methylphenyl)-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one monohydrate top
Crystal data top
C26H21NO·H2OZ = 2
Mr = 381.45F(000) = 404
Triclinic, P1Dx = 1.245 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2634 (7) ÅCell parameters from 4003 reflections
b = 9.0785 (7) Åθ = 2.3–28.3°
c = 14.1176 (12) ŵ = 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
Data collection top
Bruker SMART APEX CCD
diffractometer		4647 independent reflections
Radiation source: fine-focus sealed tube3790 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −10→10
Tmin = 0.794, Tmax = 0.862k = −11→11
9738 measured reflectionsl = −18→18
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165H 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 parametersΔρmax = 0.35 e Å−3
3 restraintsΔρmin = −0.27 e Å−3
Crystal data top
C26H21NO·H2Oγ = 100.820 (1)°
Mr = 381.45V = 1017.43 (15) Å3
Triclinic, P1Z = 2
a = 8.2634 (7) ÅMo Kα radiation
b = 9.0785 (7) ŵ = 0.08 mm−1
c = 14.1176 (12) ÅT = 100 K
α = 91.137 (1)°0.30 × 0.25 × 0.20 mm
β = 101.537 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer		4647 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3790 reflections with I > 2σ(I)
Tmin = 0.794, Tmax = 0.862Rint = 0.023
9738 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0463 restraints
wR(F2) = 0.165H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.35 e Å−3
4647 reflectionsΔρmin = −0.27 e Å−3
270 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.94050 (14)0.59600 (13)0.73474 (8)0.0254 (3)
O1W1.28132 (15)0.67478 (13)0.84124 (8)0.0250 (3)
H1W1.1758 (13)0.660 (2)0.8172 (15)0.037*
H2W1.280 (3)0.623 (2)0.8910 (11)0.037*
N10.74421 (16)0.53267 (14)1.00612 (9)0.0196 (3)
C10.71971 (18)0.67293 (16)1.03036 (10)0.0177 (3)
C20.6977 (2)0.70135 (18)1.12519 (11)0.0224 (3)
H20.69870.62391.16950.027*
C30.6751 (2)0.83978 (18)1.15372 (11)0.0232 (3)
H30.66010.85771.21760.028*
C40.67398 (19)0.95613 (17)1.08882 (11)0.0227 (3)
H40.65851.05191.10920.027*
C50.69517 (19)0.93110 (17)0.99649 (11)0.0196 (3)
H50.69471.01010.95330.024*
C60.71780 (17)0.78851 (16)0.96457 (10)0.0169 (3)
C70.73952 (17)0.75512 (16)0.86916 (10)0.0166 (3)
C80.76569 (18)0.61495 (16)0.84716 (10)0.0169 (3)
C90.76789 (18)0.50488 (17)0.91867 (11)0.0190 (3)
C100.8000 (2)0.35126 (17)0.89604 (12)0.0245 (3)
H10A0.80470.29370.95420.037*
H10B0.90730.36160.87490.037*
H10C0.70870.29870.84430.037*
C110.73297 (18)0.87247 (16)0.79625 (10)0.0173 (3)
C120.88036 (19)0.96807 (17)0.78550 (11)0.0214 (3)
H120.98570.95720.82350.026*
C130.8738 (2)1.07962 (17)0.71923 (12)0.0232 (3)
H130.97451.14490.71230.028*
C140.7202 (2)1.09540 (17)0.66338 (11)0.0218 (3)
H140.71571.17090.61780.026*
C150.5731 (2)1.00064 (17)0.67422 (11)0.0225 (3)
H150.46801.01170.63600.027*
C160.57866 (19)0.88978 (17)0.74058 (11)0.0197 (3)
H160.47750.82580.74810.024*
C170.79675 (18)0.57226 (16)0.74902 (11)0.0179 (3)
C180.65484 (19)0.49748 (16)0.67431 (10)0.0189 (3)
H180.67760.45760.61670.023*
C190.49390 (19)0.48223 (16)0.68281 (10)0.0181 (3)
H190.47440.52640.74000.022*
C200.34572 (18)0.40472 (16)0.61317 (10)0.0177 (3)
C210.18670 (19)0.42552 (17)0.62322 (11)0.0203 (3)
H210.17740.49120.67420.024*
C220.04245 (19)0.35188 (17)0.56003 (11)0.0215 (3)
H22−0.06420.36870.56800.026*
C230.0509 (2)0.25349 (17)0.48501 (11)0.0221 (3)
C240.2101 (2)0.23307 (18)0.47450 (11)0.0227 (3)
H240.21890.16720.42350.027*
C250.3546 (2)0.30677 (17)0.53679 (11)0.0216 (3)
H250.46130.29120.52800.026*
C26−0.1064 (2)0.1710 (2)0.41757 (12)0.0291 (4)
H26A−0.20110.21910.42320.044*
H26B−0.13080.06630.43480.044*
H26C−0.08980.17400.35080.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0202 (6)0.0342 (6)0.0227 (6)0.0050 (5)0.0068 (4)0.0002 (5)
O1W0.0252 (6)0.0248 (6)0.0232 (6)0.0007 (5)0.0042 (5)0.0061 (5)
N10.0217 (6)0.0181 (6)0.0185 (6)0.0030 (5)0.0040 (5)0.0034 (5)
C10.0155 (7)0.0191 (7)0.0176 (7)0.0021 (5)0.0027 (5)0.0008 (5)
C20.0230 (8)0.0263 (8)0.0182 (7)0.0046 (6)0.0050 (6)0.0045 (6)
C30.0219 (7)0.0295 (8)0.0183 (7)0.0039 (6)0.0058 (6)−0.0025 (6)
C40.0209 (7)0.0224 (7)0.0238 (8)0.0052 (6)0.0022 (6)−0.0046 (6)
C50.0190 (7)0.0184 (7)0.0209 (7)0.0040 (5)0.0027 (6)0.0013 (6)
C60.0143 (6)0.0183 (7)0.0169 (7)0.0021 (5)0.0013 (5)0.0006 (5)
C70.0120 (6)0.0180 (7)0.0184 (7)0.0015 (5)0.0013 (5)0.0017 (5)
C80.0145 (6)0.0191 (7)0.0162 (7)0.0020 (5)0.0021 (5)0.0007 (5)
C90.0187 (7)0.0185 (7)0.0184 (7)0.0029 (5)0.0015 (5)0.0004 (5)
C100.0328 (9)0.0195 (7)0.0225 (8)0.0081 (6)0.0056 (6)0.0026 (6)
C110.0203 (7)0.0168 (7)0.0150 (7)0.0044 (5)0.0039 (5)0.0007 (5)
C120.0169 (7)0.0242 (7)0.0208 (7)0.0013 (6)0.0010 (6)0.0024 (6)
C130.0230 (8)0.0205 (7)0.0245 (8)−0.0021 (6)0.0071 (6)0.0021 (6)
C140.0287 (8)0.0177 (7)0.0204 (7)0.0054 (6)0.0072 (6)0.0053 (6)
C150.0203 (7)0.0243 (8)0.0231 (8)0.0069 (6)0.0020 (6)0.0039 (6)
C160.0166 (7)0.0205 (7)0.0217 (7)0.0024 (5)0.0042 (6)0.0032 (6)
C170.0196 (7)0.0165 (7)0.0190 (7)0.0055 (5)0.0053 (6)0.0027 (5)
C180.0230 (7)0.0190 (7)0.0156 (7)0.0053 (6)0.0047 (6)0.0005 (5)
C190.0221 (7)0.0184 (7)0.0146 (7)0.0054 (6)0.0040 (6)0.0008 (5)
C200.0204 (7)0.0176 (7)0.0157 (7)0.0042 (5)0.0042 (5)0.0036 (5)
C210.0233 (8)0.0210 (7)0.0186 (7)0.0054 (6)0.0077 (6)0.0021 (6)
C220.0207 (7)0.0242 (7)0.0213 (7)0.0044 (6)0.0077 (6)0.0058 (6)
C230.0228 (8)0.0212 (7)0.0204 (7)0.0007 (6)0.0034 (6)0.0047 (6)
C240.0250 (8)0.0237 (7)0.0186 (7)0.0046 (6)0.0035 (6)−0.0024 (6)
C250.0211 (7)0.0238 (7)0.0211 (7)0.0072 (6)0.0047 (6)−0.0005 (6)
C260.0249 (8)0.0316 (9)0.0265 (8)−0.0012 (7)0.0016 (7)0.0009 (7)
Geometric parameters (Å, º) top
O1—C171.2245 (18)C12—H120.9500
O1W—H1W0.854 (10)C13—C141.388 (2)
O1W—H2W0.852 (9)C13—H130.9500
N1—C91.3149 (19)C14—C151.389 (2)
N1—C11.3736 (18)C14—H140.9500
C1—C21.412 (2)C15—C161.389 (2)
C1—C61.415 (2)C15—H150.9500
C2—C31.369 (2)C16—H160.9500
C2—H20.9500C17—C181.458 (2)
C3—C41.412 (2)C18—C191.341 (2)
C3—H30.9500C18—H180.9500
C4—C51.370 (2)C19—C201.459 (2)
C4—H40.9500C19—H190.9500
C5—C61.4196 (19)C20—C211.396 (2)
C5—H50.9500C20—C251.406 (2)
C6—C71.428 (2)C21—C221.384 (2)
C7—C81.370 (2)C21—H210.9500
C7—C111.497 (2)C22—C231.393 (2)
C8—C91.434 (2)C22—H220.9500
C8—C171.5146 (19)C23—C241.398 (2)
C9—C101.507 (2)C23—C261.506 (2)
C10—H10A0.9800C24—C251.380 (2)
C10—H10B0.9800C24—H240.9500
C10—H10C0.9800C25—H250.9500
C11—C121.394 (2)C26—H26A0.9800
C11—C161.396 (2)C26—H26B0.9800
C12—C131.394 (2)C26—H26C0.9800
H1W—O1W—H2W100 (2)C12—C13—H13120.0
C9—N1—C1118.81 (13)C13—C14—C15119.89 (14)
N1—C1—C2117.92 (13)C13—C14—H14120.1
N1—C1—C6122.51 (13)C15—C14—H14120.1
C2—C1—C6119.57 (13)C14—C15—C16120.39 (14)
C3—C2—C1120.42 (15)C14—C15—H15119.8
C3—C2—H2119.8C16—C15—H15119.8
C1—C2—H2119.8C15—C16—C11119.95 (14)
C2—C3—C4120.46 (14)C15—C16—H16120.0
C2—C3—H3119.8C11—C16—H16120.0
C4—C3—H3119.8O1—C17—C18121.12 (13)
C5—C4—C3120.12 (14)O1—C17—C8119.76 (13)
C5—C4—H4119.9C18—C17—C8119.07 (12)
C3—C4—H4119.9C19—C18—C17123.29 (13)
C4—C5—C6120.74 (14)C19—C18—H18118.4
C4—C5—H5119.6C17—C18—H18118.4
C6—C5—H5119.6C18—C19—C20126.63 (13)
C1—C6—C5118.69 (13)C18—C19—H19116.7
C1—C6—C7117.89 (13)C20—C19—H19116.7
C5—C6—C7123.41 (13)C21—C20—C25117.89 (14)
C8—C7—C6118.43 (13)C21—C20—C19119.03 (13)
C8—C7—C11121.85 (13)C25—C20—C19123.06 (13)
C6—C7—C11119.71 (12)C22—C21—C20121.01 (13)
C7—C8—C9120.04 (13)C22—C21—H21119.5
C7—C8—C17121.83 (13)C20—C21—H21119.5
C9—C8—C17118.12 (12)C21—C22—C23121.16 (14)
N1—C9—C8122.29 (13)C21—C22—H22119.4
N1—C9—C10117.14 (13)C23—C22—H22119.4
C8—C9—C10120.57 (13)C22—C23—C24117.93 (14)
C9—C10—H10A109.5C22—C23—C26121.08 (14)
C9—C10—H10B109.5C24—C23—C26120.99 (14)
H10A—C10—H10B109.5C25—C24—C23121.28 (14)
C9—C10—H10C109.5C25—C24—H24119.4
H10A—C10—H10C109.5C23—C24—H24119.4
H10B—C10—H10C109.5C24—C25—C20120.72 (14)
C12—C11—C16119.54 (14)C24—C25—H25119.6
C12—C11—C7120.23 (13)C20—C25—H25119.6
C16—C11—C7120.21 (13)C23—C26—H26A109.5
C11—C12—C13120.23 (14)C23—C26—H26B109.5
C11—C12—H12119.9H26A—C26—H26B109.5
C13—C12—H12119.9C23—C26—H26C109.5
C14—C13—C12120.00 (14)H26A—C26—H26C109.5
C14—C13—H13120.0H26B—C26—H26C109.5
C9—N1—C1—C2−178.81 (14)C8—C7—C11—C1694.05 (17)
C9—N1—C1—C60.4 (2)C6—C7—C11—C16−85.84 (17)
N1—C1—C2—C3179.12 (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—C50.2 (2)C12—C13—C14—C150.5 (2)
C3—C4—C5—C60.3 (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—C50.6 (2)C12—C11—C16—C150.7 (2)
N1—C1—C6—C71.1 (2)C7—C11—C16—C15178.87 (13)
C2—C1—C6—C7−179.66 (13)C7—C8—C17—O188.14 (18)
C4—C5—C6—C1−0.6 (2)C9—C8—C17—O1−90.49 (17)
C4—C5—C6—C7179.62 (14)C7—C8—C17—C18−94.46 (17)
C1—C6—C7—C8−1.8 (2)C9—C8—C17—C1886.91 (17)
C5—C6—C7—C8177.97 (13)O1—C17—C18—C19−173.19 (14)
C1—C6—C7—C11178.09 (13)C8—C17—C18—C199.4 (2)
C5—C6—C7—C11−2.1 (2)C17—C18—C19—C20−177.71 (13)
C6—C7—C8—C91.1 (2)C18—C19—C20—C21−166.79 (15)
C11—C7—C8—C9−178.82 (13)C18—C19—C20—C2514.5 (2)
C6—C7—C8—C17−177.54 (13)C25—C20—C21—C220.1 (2)
C11—C7—C8—C172.6 (2)C19—C20—C21—C22−178.68 (13)
C1—N1—C9—C8−1.3 (2)C20—C21—C22—C230.7 (2)
C1—N1—C9—C10178.05 (13)C21—C22—C23—C24−1.0 (2)
C7—C8—C9—N10.5 (2)C21—C22—C23—C26178.73 (14)
C17—C8—C9—N1179.17 (13)C22—C23—C24—C250.6 (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—C200.2 (2)
C8—C7—C11—C12−87.84 (18)C21—C20—C25—C24−0.5 (2)
C6—C7—C11—C1292.27 (17)C19—C20—C25—C24178.20 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w···O10.85 (1)2.03 (1)2.8654 (17)166 (2)
O1w—H2w···N1i0.85 (1)2.06 (1)2.9032 (17)170 (2)
C4—H4···O1wii0.952.493.4055 (19)161
C16—H16···O1wiii0.952.523.402 (2)155
C24—H24···Cg1iv0.952.703.6414 (17)171
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, −y+2, −z+2; (iii) x−1, y, z; (iv) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC26H21NO·H2O
Mr381.45
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)8.2634 (7), 9.0785 (7), 14.1176 (12)
α, β, γ (°)91.137 (1), 101.537 (1), 100.820 (1)
V (Å3)1017.43 (15)
Z2
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.794, 0.862
No. of measured, independent and
observed [I > 2σ(I)] reflections		9738, 4647, 3790
Rint0.023
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.165, 1.01
No. of reflections4647
No. of parameters270
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.35, −0.27

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w···O10.854 (10)2.029 (11)2.8654 (17)166 (2)
O1w—H2w···N1i0.852 (9)2.061 (10)2.9032 (17)170 (2)
C4—H4···O1wii0.952.493.4055 (19)161
C16—H16···O1wiii0.952.523.402 (2)155
C24—H24···Cg1iv0.952.703.6414 (17)171
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, −y+2, −z+2; (iii) x−1, y, z; (iv) −x+1, −y+1, −z+1.
 

Footnotes

‡Additional correspondence author, e-mail: kvpsvijayakumar@gmail.com.

Acknowledgements

VV is grateful to the DST, India, for funding through the Young Scientist Scheme (Fast Track Proposal). The authors are also grateful to the University of Malaya for support of the crystallographic facility.

References

First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationPrasath, R., Sarveswari, S., Vijayakumar, V., Narasimhamurthy, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1110.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationRoman, G. (2004). Acta Chim. Slov. 51, 537–544.  CAS Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 66| Part 11| November 2010| Pages o2710-o2711
https://doi.org/10.1107/S1600536810038791
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