(E)-3-[4-(Dimethyl­amino)­phen­yl]-1-(2-methyl-4-phenyl­quinolin-3-yl)prop-2-en-1-one 0.7-hydrate

Loh, W.-S.; Fun, H.-K.; Sarveswari, S.; Vijayakumar, V.; Prasath, R.

doi:10.1107/S1600536811019088

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1521-o1522

doi:10.1107/S1600536811019088

Open

access

(E)-3-[4-(Dimethylamino)phenyl]-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one 0.7-hydrate

Wan-Sin Loh,^a ‡ Hoong-Kun Fun,^a ^*§ S. Sarveswari,^b V. Vijayakumar ^b and R. Prasath ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India
^*Correspondence e-mail: hkfun@usm.my

(Received 5 May 2011; accepted 19 May 2011; online 25 May 2011)

In the title compound, C₂₇H₂₄N₂O·0.7H₂O, the quinoline ring system is approximately planar, with a maximum deviation of 0.011 (1) Å, and forms dihedral angles of 74.70 (4) and 80.14 (4)° with the phenyl and benzene rings, respectively. In the crystal, the molecules are linked to the water molecules via intermolecular O—H⋯N hydrogen bonds and further stabilized by C—H⋯π interactions involving the centroid of the benzene ring of the quinoline group. This benzene ring is observed to form a π–π interaction with an adjacent pyridine ring [centroid–centroid distance = 3.7120 (6) Å].

Related literature

For background to chalcone derivatives, see: Sarveswari & Vijayakumar (2011 ); Sarveswari et al. (2010 ); Loh et al. (2010b ); Shahani et al. (2010 ). For related structures, see: Fun et al. (2009 ); Loh et al. (2010a ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₇H₂₄N₂O·0.7H₂O
M_r = 405.09
Triclinic, $[P \overline 1]$
a = 9.2653 (2) Å
b = 10.6076 (2) Å
c = 12.2347 (2) Å
α = 66.409 (1)°
β = 87.758 (1)°
γ = 80.308 (1)°
V = 1085.70 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.47 × 0.31 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.964, T_max = 0.983
28425 measured reflections
8843 independent reflections
6883 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.158
S = 1.05
8843 reflections
289 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯N1ⁱ	0.85 (2)	2.01 (2)	2.8650 (17)	176 (2)
C14—H14A⋯Cg1ⁱⁱ	0.95	2.81	3.6395 (14)	147
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811019088/rz2594sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019088/rz2594Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019088/rz2594Isup3.cml

checkCIF report

Comment top

As part of our ongoing research on chalcones (Sarveswari & Vijayakumar, 2011; Sarveswari et al., 2010; Loh et al., 2010b; Shahani et al., 2010), herein we report the synthesis of new chalcone derivative.

The asymmetric unit of title compound, (Fig. 1), consists of one (E)-3-(4-(dimethylamino)phenyl)-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one molecule and one water molecule with the occupancy of 0.7. The quinoline ring system (C1–C9/N1) is approximately planar with a maximum deviation of 0.011 (1) Å at atom C9 and forms dihedral angles of 74.70 (4) and 80.14 (4)° with the benzene and phenyl rings (C10–C15 & C19–C24), respectively. Bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to the related structures (Fun et al., 2009; Loh et al., 2010a).

In the crystal packing (Fig. 2), the molecules are linked to the water molecules via intermolecular O1W—H1W1···N1 hydrogen bonds (Table 1) and further stabilized by C—H···π interactions (Table 1), involving the centroids of the benzene ring (C1–C6; Cg1) of the quinoline unit. This benzene ring is observed to form a π–π interactions with an adjacent pyridine ring (N1/C1/C6–C9; Cg2) in the stabilization of the crystal structure, with the separation Cg1···Cg2ⁱⁱⁱ = 3.7120 (6) Å [symmetry code: (iii) 1 - x, -y, -z].

Related literature top

For background to chalcone derivatives, see: Sarveswari & Vijayakumar (2011); Sarveswari et al. (2010); Loh et al. (2010b); Shahani et al. (2010). For related structures, see: Fun et al. (2009); Loh et al. (2010a). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 3-acetyl-2-methyl-4-phenylquinoline (2.6 g, 0.01 M) and N,N-dimethylamino-benzaldehyde (1.5 g 0.01 M) and a catalytic amount of KOH in 30 ml of distilled ethanol was stirred for about 24 h. The resulting mixture was concentrated to remove ethanol and then poured onto ice and neutralized with diluted acetic acid. The resultant solid was filtered, dried and purified by column chromatography using 1:1 v/v mixture of ethyl acetate and petroleum ether. Crystals suitable for X-ray analysis were obtained by slow evaporation of an acetone solution (yield: 60%). M.p.: 421–423 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along the showing the a axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

(E)-3-[4-(Dimethylamino)phenyl]-1-(2-methyl-4-phenylquinolin- 3-yl)prop-2-en-1-one 0.7-hydrate top

Crystal data top

C₂₇H₂₄N₂O·0.7H₂O	Z = 2
M_r = 405.09	F(000) = 430
Triclinic, P1	D_x = 1.239 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2653 (2) Å	Cell parameters from 9900 reflections
b = 10.6076 (2) Å	θ = 2.2–34.1°
c = 12.2347 (2) Å	µ = 0.08 mm⁻¹
α = 66.409 (1)°	T = 100 K
β = 87.758 (1)°	Block, yellow
γ = 80.308 (1)°	0.47 × 0.31 × 0.22 mm
V = 1085.70 (4) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8843 independent reflections
Radiation source: fine-focus sealed tube	6883 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 34.1°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
T_min = 0.964, T_max = 0.983	k = −16→15
28425 measured reflections	l = −19→19

Refinement top

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0836P)² + 0.2116P] where P = (F_o² + 2F_c²)/3
8843 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.45 e Å⁻³
2 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₇H₂₄N₂O·0.7H₂O	γ = 80.308 (1)°
M_r = 405.09	V = 1085.70 (4) Å³
Triclinic, P1	Z = 2
a = 9.2653 (2) Å	Mo Kα radiation
b = 10.6076 (2) Å	µ = 0.08 mm⁻¹
c = 12.2347 (2) Å	T = 100 K
α = 66.409 (1)°	0.47 × 0.31 × 0.22 mm
β = 87.758 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8843 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6883 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.983	R_int = 0.024
28425 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	2 restraints
wR(F²) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.45 e Å⁻³
8843 reflections	Δρ_min = −0.25 e Å⁻³
289 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.62190 (8)	0.03973 (8)	0.38342 (7)	0.02981 (16)
N1	0.29814 (8)	0.08211 (8)	0.10561 (7)	0.02176 (15)
N2	0.05122 (9)	0.75572 (9)	0.47082 (8)	0.02510 (16)
C1	0.36984 (9)	0.14337 (9)	0.00267 (8)	0.01954 (15)
C2	0.31833 (11)	0.14074 (10)	−0.10394 (9)	0.02472 (18)
H2A	0.2352	0.0985	−0.1025	0.030*
C3	0.38766 (12)	0.19871 (11)	−0.20888 (9)	0.0289 (2)
H3A	0.3534	0.1950	−0.2795	0.035*
C4	0.50996 (12)	0.26408 (11)	−0.21278 (9)	0.02809 (19)
H4A	0.5565	0.3051	−0.2862	0.034*
C5	0.56190 (10)	0.26855 (10)	−0.11095 (8)	0.02374 (17)
H5A	0.6442	0.3125	−0.1144	0.028*
C6	0.49338 (9)	0.20786 (9)	−0.00065 (8)	0.01872 (15)
C7	0.54149 (9)	0.20946 (9)	0.10795 (8)	0.01787 (15)
C8	0.46772 (9)	0.14656 (9)	0.21066 (8)	0.01906 (15)
C9	0.34569 (9)	0.08271 (10)	0.20584 (8)	0.02138 (16)
C10	0.67008 (9)	0.27639 (9)	0.10986 (8)	0.02043 (16)
C11	0.81131 (10)	0.21074 (11)	0.10215 (10)	0.0292 (2)
H11A	0.8256	0.1228	0.0964	0.035*
C12	0.93163 (11)	0.27357 (14)	0.10290 (11)	0.0349 (2)
H12A	1.0277	0.2286	0.0975	0.042*
C13	0.91096 (13)	0.40165 (13)	0.11151 (9)	0.0345 (2)
H13A	0.9931	0.4441	0.1124	0.041*
C14	0.77099 (13)	0.46815 (12)	0.11876 (10)	0.0336 (2)
H14A	0.7571	0.5562	0.1242	0.040*
C15	0.65074 (11)	0.40541 (10)	0.11806 (9)	0.02625 (18)
H15A	0.5548	0.4509	0.1232	0.031*
C16	0.52220 (9)	0.13497 (10)	0.32989 (8)	0.02152 (16)
C17	0.45532 (10)	0.23519 (10)	0.37833 (8)	0.02317 (17)
H17A	0.4912	0.2259	0.4533	0.028*
C18	0.34498 (10)	0.34062 (10)	0.32226 (8)	0.02172 (16)
H18A	0.3112	0.3469	0.2476	0.026*
C19	0.27230 (10)	0.44507 (9)	0.36294 (8)	0.02049 (16)
C20	0.31758 (10)	0.45868 (11)	0.46537 (8)	0.02470 (18)
H20A	0.4002	0.3964	0.5111	0.030*
C21	0.24580 (11)	0.55967 (11)	0.50161 (8)	0.02482 (18)
H21A	0.2802	0.5658	0.5712	0.030*
C22	0.12176 (9)	0.65431 (9)	0.43683 (8)	0.02082 (16)
C23	0.07597 (12)	0.64065 (12)	0.33376 (10)	0.0322 (2)
H23A	−0.0072	0.7018	0.2880	0.039*
C24	0.15050 (12)	0.53970 (11)	0.29894 (10)	0.0304 (2)
H24A	0.1178	0.5342	0.2286	0.037*
C25	0.09293 (15)	0.76160 (15)	0.58093 (11)	0.0397 (3)
H25A	0.1935	0.7804	0.5762	0.060*
H25B	0.0872	0.6722	0.6474	0.060*
H25C	0.0265	0.8362	0.5939	0.060*
C26	−0.08338 (11)	0.84364 (12)	0.40942 (11)	0.0312 (2)
H26A	−0.0656	0.8917	0.3244	0.047*
H26B	−0.1164	0.9127	0.4433	0.047*
H26C	−0.1590	0.7858	0.4192	0.047*
C27	0.26687 (12)	0.00813 (13)	0.31730 (10)	0.0321 (2)
H27A	0.1609	0.0335	0.3009	0.048*
H27B	0.2925	0.0353	0.3808	0.048*
H27C	0.2960	−0.0929	0.3427	0.048*
O1W	0.06296 (16)	0.93446 (14)	0.11443 (13)	0.0424 (3)	0.70
H1W1	0.135 (2)	0.977 (3)	0.109 (3)	0.064*	0.70
H2W1	0.098 (3)	0.8490 (13)	0.151 (2)	0.064*	0.70

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0246 (3)	0.0346 (4)	0.0280 (3)	0.0048 (3)	−0.0033 (3)	−0.0136 (3)
N1	0.0185 (3)	0.0224 (3)	0.0260 (3)	−0.0063 (3)	0.0013 (3)	−0.0103 (3)
N2	0.0228 (3)	0.0263 (4)	0.0284 (4)	−0.0008 (3)	−0.0004 (3)	−0.0144 (3)
C1	0.0191 (3)	0.0179 (3)	0.0234 (4)	−0.0040 (3)	−0.0004 (3)	−0.0097 (3)
C2	0.0263 (4)	0.0240 (4)	0.0273 (4)	−0.0065 (3)	−0.0041 (3)	−0.0125 (3)
C3	0.0350 (5)	0.0304 (5)	0.0247 (4)	−0.0075 (4)	−0.0037 (4)	−0.0131 (4)
C4	0.0325 (5)	0.0314 (5)	0.0219 (4)	−0.0093 (4)	0.0025 (3)	−0.0108 (4)
C5	0.0246 (4)	0.0256 (4)	0.0226 (4)	−0.0083 (3)	0.0027 (3)	−0.0097 (3)
C6	0.0184 (3)	0.0181 (3)	0.0213 (3)	−0.0042 (3)	0.0009 (3)	−0.0092 (3)
C7	0.0159 (3)	0.0172 (3)	0.0219 (3)	−0.0033 (3)	0.0007 (3)	−0.0091 (3)
C8	0.0162 (3)	0.0203 (4)	0.0220 (4)	−0.0031 (3)	0.0013 (3)	−0.0099 (3)
C9	0.0171 (3)	0.0232 (4)	0.0249 (4)	−0.0057 (3)	0.0027 (3)	−0.0100 (3)
C10	0.0192 (3)	0.0219 (4)	0.0207 (3)	−0.0072 (3)	−0.0002 (3)	−0.0076 (3)
C11	0.0195 (4)	0.0294 (5)	0.0389 (5)	−0.0063 (3)	0.0017 (3)	−0.0128 (4)
C12	0.0196 (4)	0.0456 (6)	0.0367 (5)	−0.0117 (4)	0.0001 (4)	−0.0109 (5)
C13	0.0335 (5)	0.0451 (6)	0.0253 (4)	−0.0249 (5)	−0.0020 (4)	−0.0070 (4)
C14	0.0413 (6)	0.0308 (5)	0.0329 (5)	−0.0193 (4)	−0.0028 (4)	−0.0116 (4)
C15	0.0276 (4)	0.0245 (4)	0.0292 (4)	−0.0093 (3)	−0.0013 (3)	−0.0113 (3)
C16	0.0182 (3)	0.0252 (4)	0.0219 (4)	−0.0039 (3)	0.0018 (3)	−0.0101 (3)
C17	0.0231 (4)	0.0262 (4)	0.0212 (4)	−0.0029 (3)	0.0010 (3)	−0.0110 (3)
C18	0.0220 (4)	0.0229 (4)	0.0218 (4)	−0.0049 (3)	0.0011 (3)	−0.0101 (3)
C19	0.0210 (4)	0.0211 (4)	0.0201 (3)	−0.0043 (3)	0.0004 (3)	−0.0086 (3)
C20	0.0244 (4)	0.0276 (4)	0.0207 (4)	0.0018 (3)	−0.0026 (3)	−0.0103 (3)
C21	0.0264 (4)	0.0284 (4)	0.0194 (4)	0.0007 (3)	−0.0023 (3)	−0.0111 (3)
C22	0.0193 (3)	0.0211 (4)	0.0227 (4)	−0.0043 (3)	0.0017 (3)	−0.0092 (3)
C23	0.0309 (5)	0.0315 (5)	0.0374 (5)	0.0071 (4)	−0.0151 (4)	−0.0203 (4)
C24	0.0322 (5)	0.0308 (5)	0.0320 (5)	0.0035 (4)	−0.0122 (4)	−0.0186 (4)
C25	0.0451 (6)	0.0470 (7)	0.0294 (5)	0.0091 (5)	−0.0026 (4)	−0.0241 (5)
C26	0.0239 (4)	0.0297 (5)	0.0414 (6)	0.0015 (4)	−0.0031 (4)	−0.0177 (4)
C27	0.0274 (4)	0.0424 (6)	0.0286 (5)	−0.0164 (4)	0.0079 (4)	−0.0127 (4)
O1W	0.0475 (7)	0.0369 (6)	0.0544 (8)	−0.0256 (6)	0.0242 (6)	−0.0250 (6)

Geometric parameters (Å, º) top

O1—C16	1.2273 (11)	C14—C15	1.3926 (14)
N1—C9	1.3218 (12)	C14—H14A	0.9500
N1—C1	1.3692 (12)	C15—H15A	0.9500
N2—C22	1.3628 (12)	C16—C17	1.4557 (13)
N2—C25	1.4437 (14)	C17—C18	1.3499 (13)
N2—C26	1.4527 (13)	C17—H17A	0.9500
C1—C2	1.4185 (12)	C18—C19	1.4466 (13)
C1—C6	1.4205 (12)	C18—H18A	0.9500
C2—C3	1.3695 (14)	C19—C24	1.3974 (13)
C2—H2A	0.9500	C19—C20	1.4049 (13)
C3—C4	1.4146 (15)	C20—C21	1.3798 (14)
C3—H3A	0.9500	C20—H20A	0.9500
C4—C5	1.3741 (13)	C21—C22	1.4152 (13)
C4—H4A	0.9500	C21—H21A	0.9500
C5—C6	1.4191 (12)	C22—C23	1.4142 (13)
C5—H5A	0.9500	C23—C24	1.3777 (15)
C6—C7	1.4253 (12)	C23—H23A	0.9500
C7—C8	1.3809 (12)	C24—H24A	0.9500
C7—C10	1.4914 (12)	C25—H25A	0.9800
C8—C9	1.4269 (12)	C25—H25B	0.9800
C8—C16	1.5136 (12)	C25—H25C	0.9800
C9—C27	1.5072 (13)	C26—H26A	0.9800
C10—C15	1.3933 (14)	C26—H26B	0.9800
C10—C11	1.3937 (13)	C26—H26C	0.9800
C11—C12	1.3939 (14)	C27—H27A	0.9800
C11—H11A	0.9500	C27—H27B	0.9800
C12—C13	1.3853 (19)	C27—H27C	0.9800
C12—H12A	0.9500	O1W—H1W1	0.850 (10)
C13—C14	1.3858 (18)	O1W—H2W1	0.846 (10)
C13—H13A	0.9500

C9—N1—C1	118.84 (7)	C10—C15—H15A	119.8
C22—N2—C25	120.55 (8)	O1—C16—C17	121.86 (8)
C22—N2—C26	120.61 (8)	O1—C16—C8	118.44 (8)
C25—N2—C26	117.90 (9)	C17—C16—C8	119.71 (8)
N1—C1—C2	118.17 (8)	C18—C17—C16	123.43 (8)
N1—C1—C6	122.50 (8)	C18—C17—H17A	118.3
C2—C1—C6	119.33 (8)	C16—C17—H17A	118.3
C3—C2—C1	120.40 (9)	C17—C18—C19	127.37 (8)
C3—C2—H2A	119.8	C17—C18—H18A	116.3
C1—C2—H2A	119.8	C19—C18—H18A	116.3
C2—C3—C4	120.44 (9)	C24—C19—C20	116.51 (8)
C2—C3—H3A	119.8	C24—C19—C18	119.96 (8)
C4—C3—H3A	119.8	C20—C19—C18	123.53 (8)
C5—C4—C3	120.39 (9)	C21—C20—C19	122.04 (8)
C5—C4—H4A	119.8	C21—C20—H20A	119.0
C3—C4—H4A	119.8	C19—C20—H20A	119.0
C4—C5—C6	120.41 (8)	C20—C21—C22	121.07 (8)
C4—C5—H5A	119.8	C20—C21—H21A	119.5
C6—C5—H5A	119.8	C22—C21—H21A	119.5
C5—C6—C1	119.02 (8)	N2—C22—C23	121.45 (8)
C5—C6—C7	123.16 (8)	N2—C22—C21	121.59 (8)
C1—C6—C7	117.82 (8)	C23—C22—C21	116.95 (8)
C8—C7—C6	118.59 (7)	C24—C23—C22	120.78 (9)
C8—C7—C10	121.15 (8)	C24—C23—H23A	119.6
C6—C7—C10	120.25 (7)	C22—C23—H23A	119.6
C7—C8—C9	119.71 (8)	C23—C24—C19	122.64 (9)
C7—C8—C16	120.54 (7)	C23—C24—H24A	118.7
C9—C8—C16	119.57 (8)	C19—C24—H24A	118.7
N1—C9—C8	122.52 (8)	N2—C25—H25A	109.5
N1—C9—C27	116.52 (8)	N2—C25—H25B	109.5
C8—C9—C27	120.93 (8)	H25A—C25—H25B	109.5
C15—C10—C11	119.24 (8)	N2—C25—H25C	109.5
C15—C10—C7	120.65 (8)	H25A—C25—H25C	109.5
C11—C10—C7	120.11 (8)	H25B—C25—H25C	109.5
C10—C11—C12	120.25 (10)	N2—C26—H26A	109.5
C10—C11—H11A	119.9	N2—C26—H26B	109.5
C12—C11—H11A	119.9	H26A—C26—H26B	109.5
C13—C12—C11	119.95 (11)	N2—C26—H26C	109.5
C13—C12—H12A	120.0	H26A—C26—H26C	109.5
C11—C12—H12A	120.0	H26B—C26—H26C	109.5
C12—C13—C14	120.31 (9)	C9—C27—H27A	109.5
C12—C13—H13A	119.8	C9—C27—H27B	109.5
C14—C13—H13A	119.8	H27A—C27—H27B	109.5
C13—C14—C15	119.77 (11)	C9—C27—H27C	109.5
C13—C14—H14A	120.1	H27A—C27—H27C	109.5
C15—C14—H14A	120.1	H27B—C27—H27C	109.5
C14—C15—C10	120.49 (10)	H1W1—O1W—H2W1	105 (3)
C14—C15—H15A	119.8

C9—N1—C1—C2	179.43 (8)	C15—C10—C11—C12	0.13 (15)
C9—N1—C1—C6	−0.10 (13)	C7—C10—C11—C12	179.46 (9)
N1—C1—C2—C3	−179.00 (9)	C10—C11—C12—C13	0.09 (17)
C6—C1—C2—C3	0.54 (14)	C11—C12—C13—C14	−0.34 (17)
C1—C2—C3—C4	−1.09 (16)	C12—C13—C14—C15	0.37 (16)
C2—C3—C4—C5	0.88 (16)	C13—C14—C15—C10	−0.15 (16)
C3—C4—C5—C6	−0.10 (16)	C11—C10—C15—C14	−0.10 (15)
C4—C5—C6—C1	−0.43 (14)	C7—C10—C15—C14	−179.43 (9)
C4—C5—C6—C7	−179.74 (9)	C7—C8—C16—O1	−81.63 (11)
N1—C1—C6—C5	179.74 (8)	C9—C8—C16—O1	93.64 (11)
C2—C1—C6—C5	0.22 (13)	C7—C8—C16—C17	98.80 (10)
N1—C1—C6—C7	−0.92 (13)	C9—C8—C16—C17	−85.93 (11)
C2—C1—C6—C7	179.56 (8)	O1—C16—C17—C18	−179.59 (9)
C5—C6—C7—C8	−179.58 (8)	C8—C16—C17—C18	−0.03 (14)
C1—C6—C7—C8	1.11 (12)	C16—C17—C18—C19	−179.76 (9)
C5—C6—C7—C10	−0.34 (13)	C17—C18—C19—C24	−174.09 (10)
C1—C6—C7—C10	−179.65 (8)	C17—C18—C19—C20	6.19 (15)
C6—C7—C8—C9	−0.37 (12)	C24—C19—C20—C21	0.20 (15)
C10—C7—C8—C9	−179.60 (8)	C18—C19—C20—C21	179.92 (9)
C6—C7—C8—C16	174.89 (8)	C19—C20—C21—C22	0.35 (15)
C10—C7—C8—C16	−4.34 (13)	C25—N2—C22—C23	175.46 (11)
C1—N1—C9—C8	0.92 (13)	C26—N2—C22—C23	6.80 (15)
C1—N1—C9—C27	−177.32 (8)	C25—N2—C22—C21	−5.80 (15)
C7—C8—C9—N1	−0.70 (14)	C26—N2—C22—C21	−174.47 (9)
C16—C8—C9—N1	−176.00 (8)	C20—C21—C22—N2	−179.07 (9)
C7—C8—C9—C27	177.47 (9)	C20—C21—C22—C23	−0.28 (15)
C16—C8—C9—C27	2.17 (13)	N2—C22—C23—C24	178.45 (10)
C8—C7—C10—C15	−75.46 (11)	C21—C22—C23—C24	−0.35 (16)
C6—C7—C10—C15	105.32 (10)	C22—C23—C24—C19	0.93 (19)
C8—C7—C10—C11	105.21 (11)	C20—C19—C24—C23	−0.84 (16)
C6—C7—C10—C11	−74.01 (12)	C18—C19—C24—C23	179.43 (10)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···N1ⁱ	0.85 (2)	2.01 (2)	2.8650 (17)	176 (2)
C14—H14A···Cg1ⁱⁱ	0.95	2.81	3.6395 (14)	147

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₄N₂O·0.7H₂O
M_r	405.09
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.2653 (2), 10.6076 (2), 12.2347 (2)
α, β, γ (°)	66.409 (1), 87.758 (1), 80.308 (1)
V (Å³)	1085.70 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.47 × 0.31 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.964, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	28425, 8843, 6883
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.789

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.158, 1.05
No. of reflections	8843
No. of parameters	289
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.25

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···N1ⁱ	0.85 (2)	2.01 (2)	2.8650 (17)	176 (2)
C14—H14A···Cg1ⁱⁱ	0.95	2.81	3.6395 (14)	147

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z.

Footnotes

‡Thomson Reuters ResearcherID: C-7581-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of a Research Fellowship. VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Loh, W.-S., Sarveswari, S., Vijayakumar, V. & Reddy, B. P. (2009). Acta Cryst. E65, o2688–o2689. Web of Science CrossRef IUCr Journals Google Scholar
Loh, W.-S., Fun, H.-K., Sarveswari, S., Vijayakumar, V. & Reddy, B. P. (2010a). Acta Cryst. E66, o91–o92. Web of Science CSD CrossRef IUCr Journals Google Scholar
Loh, W.-S., Fun, H.-K., Sarveswari, S., Vijayakumar, V. & Reddy, B. P. (2010b). Acta Cryst. E66, o353–o354. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sarveswari, S. & Vijayakumar, V. (2011). Arab. J. Chem. doi:10.1016/j.arabjc.2011.01.032. Google Scholar
Sarveswari, S., Vijayakumar, V., Prasath, R., Narasimhamurthy, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o3284. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shahani, T., Fun, H.-K., Sarveswari, S., Vijayakumar, V. & Ragavan, R. V. (2010). Acta Cryst. E66, o374. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1521-o1522

doi:10.1107/S1600536811019088

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

(E)-3-[4-(Di­methyl­amino)­phen­yl]-1-(2-methyl-4-phenyl­quinolin-3-yl)prop-2-en-1-one 0.7-hydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

(E)-3-[4-(Dimethylamino)phenyl]-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one 0.7-hydrate