(E)-3-Phenyl-3-(3-phenyl-1H-1-pyrazol­yl)-2-propenal

Susindran, V.; Athimoolam, S.; Bahadur, S.A.; Sridhar, B.; Manikannan, R.; Muthusubramanian, S.

doi:10.1107/S1600536810004332

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o577

doi:10.1107/S1600536810004332

Open

access

(E)-3-Phenyl-3-(3-phenyl-1H-1-pyrazolyl)-2-propenal

V. Susindran,^a S. Athimoolam,^b S. Asath Bahadur,^c ^* B. Sridhar,^d R. Manikannan ^e and S. Muthusubramanian ^e

^aDepartment of Lighthouses & Lightships, Ministry of Shipping, Nagapattinam Lighthouse & DGPS station, Nagapattinam 611 001, India, ^bDepartment of Physics, University College of Engineering Nagercoil, Anna University Tirunelveli, Nagercoil 629 004, India, ^cDepartment of Physics, Kalasalingam University, Anand Nagar, Krishnan Koil 626 190, India, ^dLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India, and ^eDepartment of Organic Chemistry, Madurai Kamaraj University, Madurai 625 021, India
^*Correspondence e-mail: s_a_bahadur@yahoo.co.in

(Received 2 January 2010; accepted 3 February 2010; online 10 February 2010)

In the title compound C₁₈H₁₄N₂O, the pendant rings make dihedral angles of 66.1 (1)° and 13.9 (1) with the central ring. In the crystal, two molecules form a cyclic centrosymmetric R₂²(22) dimer through pairs of C—H⋯O bonds. These dimers are further connected into zigzag chains extending along the b axis through C—H⋯π and C—H⋯O interactions.

Related literature

For the pharmacological and medicinal properties of the title compound, see: Baraldi et al. (1998 ); Bruno et al. (1990 ); Chen & Li (1998 ); Cottineau et al. (2002 ); Londershausen (1996 ); Mishra et al. (1998 ); Smith et al. (2001 ). For hybridization and electron delocalization, see: Beddoes et al. (1986 ); Jin et al. (2004 ). For ring and chain motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₁₄N₂O
M_r = 274.31
Monoclinic, P 2₁ /c
a = 8.6157 (7) Å
b = 18.0969 (12) Å
c = 10.0861 (6) Å
β = 113.091 (6)°
V = 1446.61 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.23 × 0.21 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.863, T_max = 0.994
13719 measured reflections
2547 independent reflections
2262 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.105
S = 1.05
2547 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C31–C36 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C35—H35⋯O1ⁱ	0.93	2.59	3.358 (2)	140
C13—H13⋯O1ⁱⁱ	0.93	2.66	3.360 (2)	133
C14—H14⋯Cgⁱⁱⁱ	0.93	2.95	3.703 (2)	139
Symmetry codes: (i) -x+2, -y, -z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL/PC; molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL/PC.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810004332/fj2268sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004332/fj2268Isup2.hkl

checkCIF report

Comment top

Pyrazole refers both to the class of simple aromatic ring organic compounds and of the heterocyclic series characterized by a 5-membered ring structure composed of three carbon atoms and two nitrogen atoms in adjacent positions and to the unsubstituted parent compound. Being so composed and having pharmacological effects on humans, they are classified as alkaloids although they are rare in nature. Pyrazole and its derivatives are successfully tested for their antifungal (Chen & Li, 1998), antihistaminic (Mishra et al.,1998), anti-inflammatory (Smith et al., 2001), antiarrhythmic and sedative (Bruno et al., 1990), hypoglycemic (Cottineau et al., 2002), antiviral (Baraldi et al., 1998) and pesticidal (Londershausen, 1996) activities.

An ORTEP plot of the molecule is shown in Fig. 1. The pyrazole ring adopts planar conformation. The phenyl rings and the plane of the pyrazole ring are making the dihedral angles of 66.1 (1)° (with C12/C17 ring) and 13.9 (1)° (with C31/C36 ring). The two phenyl rings are oriented with the dihedral angle of 79.9 (1)°. Further, pyrazole ring is making an angle of 15.8 (2)° with the propenal plane (C11,C1A,C2A,O1). The sum of the angles at N1 of the pyrazole ring (359.8 (1)°) is in accordance with sp² hybridization (Beddoes et al., 1986). The C—N bond lengths in the pyrazole ring are 1.326 (2) and 1.355 (2) Å, which are shorter than a C—N single bond length of 1.443 Å, but longer than a double bond length of 1.269 Å, (Jin et al.,2004), indicating electron delocalization.

The crystal packing is stabilized through moderate C—H···O, C—H···N and C—H···π interactions (Table 1). Two symmetry-related molecules form a cyclic centrosymmetric R₂²(22) dimer through C35—H35···O1ⁱ bond around the inversion centers of the unit cell (Fig 2). These dimers are connected into two zigzag chains extending along the b axis through C—H···π and another C—H···O interaction (Bernstein et al., 1995).

Related literature top

For the pharmacological and medicinal properties of the title compound, see: Baraldi et al. (1998); Bruno et al. (1990); Chen & Li (1998); Cottineau et al. (2002); Londershausen (1996); Mishra et al. (1998); Smith et al. (2001). For hybridization and electron delocalization, see: Beddoes et al. (1986); Jin et al. (2004). For ring and chain motifs, see: Bernstein et al. (1995).

Experimental top

To a mixture of 1-phenyl-1-ethanone N-[(E)-1-phenylethylidene]hydrazone (0.003 mole) and 3 ml of dimethyl formamide kept in ice bath at 0 °C, phosphorous oxycholride (0.024 mole) was added dropwise for 5 to 10 minutes. The reaction mixture was then irradiated under microwaves for 30 sec. The process of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into crushed ice and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate. The different compound was separated by column chromatography using petroleum ether and ethyl acetate mixture as eluent. This isolated compound was recrystallized to obtain the title compound.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with atom numbering scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed down the a axis.

(E)-3-Phenyl-3-(3-phenyl-1H-1-pyrazolyl)-2-propenal top

Crystal data top

C₁₈H₁₄N₂O	F(000) = 576
M_r = 274.31	D_x = 1.260 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5126 reflections
a = 8.6157 (7) Å	θ = 1.7–27.6°
b = 18.0969 (12) Å	µ = 0.08 mm⁻¹
c = 10.0861 (6) Å	T = 293 K
β = 113.091 (6)°	Block, colourless
V = 1446.61 (19) Å³	0.23 × 0.21 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2547 independent reflections
Radiation source: fine-focus sealed tube	2262 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
T_min = 0.863, T_max = 0.994	k = −21→21
13719 measured reflections	l = −11→11

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0509P)² + 0.2744P] where P = (F_o² + 2F_c²)/3
2547 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₈H₁₄N₂O	V = 1446.61 (19) Å³
M_r = 274.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.6157 (7) Å	µ = 0.08 mm⁻¹
b = 18.0969 (12) Å	T = 293 K
c = 10.0861 (6) Å	0.23 × 0.21 × 0.18 mm
β = 113.091 (6)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2547 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	2262 reflections with I > 2σ(I)
T_min = 0.863, T_max = 0.994	R_int = 0.024
13719 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.05	Δρ_max = 0.14 e Å⁻³
2547 reflections	Δρ_min = −0.15 e Å⁻³
190 parameters

Special details top

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
N1	0.61426 (14)	0.02209 (6)	0.24676 (12)	0.0463 (3)
N2	0.74924 (13)	−0.01152 (6)	0.23393 (12)	0.0447 (3)
C3	0.81474 (17)	−0.05400 (8)	0.34980 (14)	0.0467 (3)
C4	0.7236 (2)	−0.04724 (11)	0.43775 (17)	0.0663 (5)
H4	0.7448	−0.0712	0.5247	0.080*
C5	0.5990 (2)	0.00119 (10)	0.37010 (17)	0.0649 (5)
H5	0.5172	0.0174	0.4022	0.078*
C11	0.52083 (16)	0.07517 (7)	0.14569 (14)	0.0432 (3)
C12	0.36253 (17)	0.10037 (7)	0.15681 (14)	0.0442 (3)
C13	0.3380 (2)	0.17479 (9)	0.17313 (18)	0.0573 (4)
H13	0.4230	0.2085	0.1821	0.069*
C14	0.1874 (2)	0.19915 (10)	0.17617 (19)	0.0690 (5)
H14	0.1716	0.2493	0.1871	0.083*
C15	0.0613 (2)	0.14992 (10)	0.16317 (18)	0.0653 (5)
H15	−0.0406	0.1667	0.1633	0.078*
C16	0.08564 (19)	0.07612 (10)	0.14998 (17)	0.0595 (4)
H16	0.0008	0.0427	0.1428	0.071*
C17	0.23541 (18)	0.05101 (8)	0.14726 (15)	0.0510 (4)
H17	0.2513	0.0007	0.1390	0.061*
C31	0.96351 (17)	−0.09984 (7)	0.37111 (16)	0.0478 (4)
C32	1.0553 (2)	−0.13183 (9)	0.50393 (17)	0.0626 (4)
H32	1.0215	−0.1250	0.5801	0.075*
C33	1.1966 (2)	−0.17376 (10)	0.5237 (2)	0.0757 (5)
H33	1.2567	−0.1955	0.6128	0.091*
C34	1.2482 (2)	−0.18350 (11)	0.4134 (3)	0.0815 (6)
H34	1.3454	−0.2106	0.4281	0.098*
C35	1.1569 (2)	−0.15340 (10)	0.2805 (2)	0.0772 (5)
H35	1.1913	−0.1608	0.2048	0.093*
C36	1.0147 (2)	−0.11233 (9)	0.25925 (19)	0.0598 (4)
H36	0.9524	−0.0928	0.1686	0.072*
C1A	0.57622 (17)	0.10007 (8)	0.04689 (15)	0.0483 (3)
H1A	0.6831	0.0854	0.0552	0.058*
C2A	0.48155 (19)	0.14796 (8)	−0.07132 (16)	0.0524 (4)
H2A	0.3733	0.1617	−0.0819	0.063*
O1	0.53501 (16)	0.17125 (7)	−0.15736 (13)	0.0747 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0437 (6)	0.0521 (7)	0.0449 (6)	0.0073 (5)	0.0193 (5)	0.0021 (5)
N2	0.0409 (6)	0.0464 (7)	0.0471 (7)	0.0035 (5)	0.0174 (5)	−0.0006 (5)
C3	0.0451 (8)	0.0474 (8)	0.0438 (8)	0.0006 (6)	0.0133 (6)	0.0000 (6)
C4	0.0683 (10)	0.0862 (12)	0.0498 (9)	0.0222 (9)	0.0291 (8)	0.0186 (8)
C5	0.0647 (10)	0.0859 (12)	0.0543 (9)	0.0226 (9)	0.0344 (8)	0.0143 (8)
C11	0.0404 (7)	0.0424 (7)	0.0439 (7)	−0.0005 (6)	0.0136 (6)	−0.0044 (6)
C12	0.0424 (7)	0.0479 (8)	0.0406 (7)	0.0033 (6)	0.0147 (6)	−0.0014 (6)
C13	0.0544 (9)	0.0491 (8)	0.0668 (10)	0.0023 (7)	0.0221 (8)	−0.0055 (7)
C14	0.0715 (11)	0.0548 (10)	0.0816 (12)	0.0193 (8)	0.0312 (9)	−0.0035 (8)
C15	0.0508 (9)	0.0807 (12)	0.0679 (11)	0.0188 (8)	0.0270 (8)	0.0051 (9)
C16	0.0470 (8)	0.0715 (11)	0.0627 (10)	0.0010 (7)	0.0244 (7)	0.0055 (8)
C17	0.0495 (8)	0.0499 (8)	0.0554 (9)	0.0015 (6)	0.0227 (7)	−0.0002 (7)
C31	0.0434 (8)	0.0411 (7)	0.0539 (8)	−0.0011 (6)	0.0137 (6)	−0.0006 (6)
C32	0.0595 (10)	0.0632 (10)	0.0544 (9)	0.0050 (8)	0.0106 (8)	0.0007 (7)
C33	0.0610 (11)	0.0675 (11)	0.0761 (12)	0.0148 (9)	0.0025 (9)	0.0085 (9)
C34	0.0601 (11)	0.0664 (11)	0.1134 (17)	0.0207 (9)	0.0290 (11)	0.0097 (11)
C35	0.0775 (12)	0.0679 (11)	0.1003 (15)	0.0211 (9)	0.0500 (11)	0.0127 (10)
C36	0.0612 (10)	0.0552 (9)	0.0675 (10)	0.0123 (7)	0.0301 (8)	0.0106 (7)
C1A	0.0406 (7)	0.0501 (8)	0.0541 (8)	0.0016 (6)	0.0186 (6)	0.0003 (6)
C2A	0.0518 (8)	0.0488 (8)	0.0570 (9)	−0.0003 (7)	0.0216 (7)	0.0008 (7)
O1	0.0825 (9)	0.0766 (8)	0.0753 (8)	0.0041 (6)	0.0420 (7)	0.0219 (6)

Geometric parameters (Å, º) top

N1—C5	1.3552 (19)	C16—C17	1.378 (2)
N1—N2	1.3627 (15)	C16—H16	0.9300
N1—C11	1.4023 (18)	C17—H17	0.9300
N2—C3	1.3259 (17)	C31—C36	1.382 (2)
C3—C4	1.402 (2)	C31—C32	1.387 (2)
C3—C31	1.470 (2)	C32—C33	1.380 (2)
C4—C5	1.346 (2)	C32—H32	0.9300
C4—H4	0.9300	C33—C34	1.363 (3)
C5—H5	0.9300	C33—H33	0.9300
C11—C1A	1.340 (2)	C34—C35	1.373 (3)
C11—C12	1.4835 (18)	C34—H34	0.9300
C12—C13	1.383 (2)	C35—C36	1.376 (2)
C12—C17	1.387 (2)	C35—H35	0.9300
C13—C14	1.381 (2)	C36—H36	0.9300
C13—H13	0.9300	C1A—C2A	1.440 (2)
C14—C15	1.371 (3)	C1A—H1A	0.9300
C14—H14	0.9300	C2A—O1	1.2068 (18)
C15—C16	1.366 (2)	C2A—H2A	0.9300
C15—H15	0.9300

C5—N1—N2	110.89 (11)	C15—C16—H16	119.8
C5—N1—C11	128.59 (12)	C17—C16—H16	119.8
N2—N1—C11	120.31 (11)	C16—C17—C12	120.40 (14)
C3—N2—N1	105.02 (11)	C16—C17—H17	119.8
N2—C3—C4	110.90 (13)	C12—C17—H17	119.8
N2—C3—C31	120.10 (13)	C36—C31—C32	118.46 (14)
C4—C3—C31	129.01 (13)	C36—C31—C3	120.81 (13)
C5—C4—C3	105.64 (14)	C32—C31—C3	120.73 (14)
C5—C4—H4	127.2	C33—C32—C31	120.37 (17)
C3—C4—H4	127.2	C33—C32—H32	119.8
C4—C5—N1	107.55 (14)	C31—C32—H32	119.8
C4—C5—H5	126.2	C34—C33—C32	120.31 (17)
N1—C5—H5	126.2	C34—C33—H33	119.8
C1A—C11—N1	120.03 (12)	C32—C33—H33	119.8
C1A—C11—C12	123.97 (13)	C33—C34—C35	120.04 (17)
N1—C11—C12	116.00 (12)	C33—C34—H34	120.0
C13—C12—C17	118.80 (13)	C35—C34—H34	120.0
C13—C12—C11	119.78 (13)	C34—C35—C36	120.04 (18)
C17—C12—C11	121.40 (12)	C34—C35—H35	120.0
C14—C13—C12	120.15 (15)	C36—C35—H35	120.0
C14—C13—H13	119.9	C35—C36—C31	120.73 (16)
C12—C13—H13	119.9	C35—C36—H36	119.6
C15—C14—C13	120.42 (16)	C31—C36—H36	119.6
C15—C14—H14	119.8	C11—C1A—C2A	124.51 (13)
C13—C14—H14	119.8	C11—C1A—H1A	117.7
C16—C15—C14	119.87 (15)	C2A—C1A—H1A	117.7
C16—C15—H15	120.1	O1—C2A—C1A	123.61 (14)
C14—C15—H15	120.1	O1—C2A—H2A	118.2
C15—C16—C17	120.33 (16)	C1A—C2A—H2A	118.2

C5—N1—N2—C3	0.88 (16)	C13—C14—C15—C16	1.3 (3)
C11—N1—N2—C3	175.96 (12)	C14—C15—C16—C17	−1.1 (3)
N1—N2—C3—C4	−0.64 (16)	C15—C16—C17—C12	−0.5 (2)
N1—N2—C3—C31	179.26 (12)	C13—C12—C17—C16	1.8 (2)
N2—C3—C4—C5	0.2 (2)	C11—C12—C17—C16	−176.44 (13)
C31—C3—C4—C5	−179.71 (15)	N2—C3—C31—C36	−14.4 (2)
C3—C4—C5—N1	0.4 (2)	C4—C3—C31—C36	165.51 (16)
N2—N1—C5—C4	−0.8 (2)	N2—C3—C31—C32	165.91 (14)
C11—N1—C5—C4	−175.36 (15)	C4—C3—C31—C32	−14.2 (2)
C5—N1—C11—C1A	165.51 (15)	C36—C31—C32—C33	1.4 (2)
N2—N1—C11—C1A	−8.60 (19)	C3—C31—C32—C33	−178.88 (15)
C5—N1—C11—C12	−14.5 (2)	C31—C32—C33—C34	0.7 (3)
N2—N1—C11—C12	171.43 (11)	C32—C33—C34—C35	−1.9 (3)
C1A—C11—C12—C13	−56.2 (2)	C33—C34—C35—C36	1.1 (3)
N1—C11—C12—C13	123.79 (15)	C34—C35—C36—C31	1.1 (3)
C1A—C11—C12—C17	122.03 (16)	C32—C31—C36—C35	−2.3 (2)
N1—C11—C12—C17	−58.00 (17)	C3—C31—C36—C35	178.02 (15)
C17—C12—C13—C14	−1.6 (2)	N1—C11—C1A—C2A	172.66 (13)
C11—C12—C13—C14	176.68 (14)	C12—C11—C1A—C2A	−7.4 (2)
C12—C13—C14—C15	0.0 (3)	C11—C1A—C2A—O1	178.19 (15)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C31–C36 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C35—H35···O1ⁱ	0.93	2.59	3.358 (2)	140
C13—H13···O1ⁱⁱ	0.93	2.66	3.360 (2)	133
C14—H14···Cgⁱⁱⁱ	0.93	2.95	3.703 (2)	139

Symmetry codes: (i) −x+2, −y, −z; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄N₂O
M_r	274.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.6157 (7), 18.0969 (12), 10.0861 (6)
β (°)	113.091 (6)
V (Å³)	1446.61 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.23 × 0.21 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.863, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	13719, 2547, 2262
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.105, 1.05
No. of reflections	2547
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.15

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL/PC (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C31–C36 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C35—H35···O1ⁱ	0.93	2.59	3.358 (2)	140
C13—H13···O1ⁱⁱ	0.93	2.66	3.360 (2)	133
C14—H14···Cgⁱⁱⁱ	0.93	2.95	3.703 (2)	139

Symmetry codes: (i) −x+2, −y, −z; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+1/2.

Acknowledgements

VS and SAB sincerely thank the Vice Chancellor and Management of Kalasalingam University, Anand Nagar, Krishnan Koil, for their support and encouragement. SA thanks the Vice-Chancellor of Anna University Tirunelveli for his support and encouragement.

References

Baraldi, P. G., Manfredini, S., Romagnoli, R., Stevanato, L., Zaid, A. N. & Manservigi, R. (1998). Nucleosides Nucleotides, 17, 2165–2171. Web of Science CrossRef CAS Google Scholar
Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787–797. CSD CrossRef Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruno, O., Bondavalli, F., Ranise, A., Schenone, P., Losasso, C., Cilenti, L., Matera, C. & Marmo, E. (1990). Farmaco, 45, 147–66. CAS PubMed Web of Science Google Scholar
Chen, H. S. & Li, Z. M. (1998). Chem. J. Chin. Univ. 19, 572–576. CAS Google Scholar
Cottineau, B., Toto, P., Marot, C., Pipaud, A. & Chenault, J. (2002). Bioorg. Med. Chem. 12, 2105–2108. CrossRef CAS Google Scholar
Jin, Z.-M., Li, L., Li, M.-C., Hu, M.-L. & Shen, L. (2004). Acta Cryst. C60, o642–o643. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Londershausen, M. (1996). Pestic. Sci. 48, 269–274. CrossRef CAS Google Scholar
Mishra, P. D., Wahidullah, S. & Kamat, S. Y. (1998). Indian J. Chem. Sect. B, 37, 199–200. Google Scholar
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Smith, S. R., Denhardt, G. & Terminelli, C. (2001). Eur. J. Pharmacol. 432, 107–119. Web of Science CrossRef PubMed CAS 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 66| Part 3| March 2010| Page o577

doi:10.1107/S1600536810004332

Open

access