(E)-3-(4-Methyl­phen­yl)-3-[3-(4-methyl­phen­yl)-1H-pyrazol-1-yl]-2-propenal

Ramesh, P.; Subbiahpandi, A.; Manikannan, R.; Muthusubramanian, S.; Ponnuswamy, M.N.

doi:10.1107/S1600536808034697

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2243

doi:10.1107/S1600536808034697

Open

access

(E)-3-(4-Methylphenyl)-3-[3-(4-methylphenyl)-1H-pyrazol-1-yl]-2-propenal

P. Ramesh,^a A. Subbiahpandi,^a Ramaiyan Manikannan,^b S. Muthusubramanian ^b and M. N. Ponnuswamy ^c ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 14 August 2008; accepted 23 October 2008; online 31 October 2008)

In the title compound, C₂₀H₁₈N₂O, the pyrazole ring adopts a planar conformation. The C—N bond lengths in the pyrazole ring are shorter than a standard C—N single bond (1.443 Å), but longer than a standard double bond (1.269 Å), indicating electron delocalization. The propenal group assumes an extended conformation. Intermolecular C—H⋯O hydrogen bonds connect molecules into cyclic centrosymmetric R₂²(26) dimers, which are cross-linked via C—H⋯π interactions.

Related literature

For the properties of pyrazole derivatives, 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 related literature, see: Beddoes et al. (1986 ); Jin et al. (2004 ); Bernstein et al. (1995 ); Cordell (1981 ).

Experimental

Crystal data

C₂₀H₁₈N₂O
M_r = 302.36
Triclinic, $[P \overline 1]$
a = 10.0560 (9) Å
b = 10.0786 (8) Å
c = 10.3176 (9) Å
α = 62.040 (4)°
β = 79.356 (4)°
γ = 63.038 (4)°
V = 822.73 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.30 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.980, T_max = 0.985
14086 measured reflections
2887 independent reflections
2315 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.154
S = 1.03
2887 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22B⋯O1ⁱ	0.96	2.60	3.446 (3)	148
C9—H9⋯Cg1ⁱⁱ	0.93	2.80	3.690 (3)	161
Symmetry codes: (i) -x+2, -y, -z+1; (ii) x-1, y+1, z. Cg1 is the centroid of the C16–C21 ring.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034697/gw2051sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034697/gw2051Isup2.hkl

checkCIF report

Comment top

Some pyrazole derivatives are successfully tested for their antifungal (Chen & Li, 1998), antihistaminic (Mishra et al., 1998) and anti-inflammatory (Smith et al., 2001) properties. These derivatives also possess significant antiarrhythmic and sedative (Bruno et al., 1990), hypoglycemic (Cottineau et al., 2002), antiviral (Baraldi et al., 1998), and pesticidal (Londershausen,1996) activities.

The pyrazole ring adopts planar conformation. The sum of the angles at N1 of the pyrazole ring (360.0°) is in accordance with sp² hybridization (Beddoes et al., 1986). The C—N bond lengths in the pyrazole ring are 1.321 (2) and 1.360 (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 pyrazole ring A and methylphenyl ring C are near-coplanar with the inter-ring dihedral angle of 4.50 (13)°, whereas the pyrazole ring is twisted by an angle of 66.31 (12)° to the methylphenyl ring B. The propenal group assumes an extended conformation which is evidenced from the torsion angles [N1—C6—C14—C15]-169.74 (16) ° and [C5—N1—C6—C14]-160.85 (19)°. The crystal packing is stabilized by C—H···O and C—H-π interactions in addition to van der Waals forces. The molecules at (x, y, z) and (2 - x,-y,1 - z) are linked by C22—H22B···O1 hydrogen bonds into cyclic cenrosymmetric R₂²(26) dimers,

Related literature top

For the properties of pyrazole derivatives, 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 related literature, see: Beddoes et al. (1986); Jin et al. (2004); Bernstein et al. (1995); Cordell (1981). Cg1 is the centroid of the C16–C21 ring.

Experimental top

The mixture of 1-(4-methylphenyl)-1-ethanone N-[(E)-1-phenylethylidene] hydrazone (0.003 mole) and 3 ml of dimethyl formamide kept in an ice bath at 0° C, phosphorus oxycholride (0.024 mole) was added dropwise for 5–10 minutes. The reaction mixture was then kept in a microwave oven at 600 W for 30–60 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 with anhydrous sodium sulfate. The different compounds present in the mixture were separated by column chromatography using petroleum ether and ethyl acetate mixture as eluent. This isolated compound was recrystallized in dichloromethane to obtain (E)-3-(4-methylphenyl)-3-[3-(4-methylphenyl)-1H -pyrazol-1-yl]-2-propenal in 34% yield.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. Perspective view of the molecule showing the thermal ellipsoids are drawn at 50% probability level. The H atoms are shown as small circles of arbitrary radii.
	Fig. 2. The crystal packing of the molecules viewed down the a axis.

(E)-3-(4-Methylphenyl)-3-[3-(4-methylphenyl)-1H-pyrazol-1-yl]- 2-propenal top

Crystal data top

C₂₀H₁₈N₂O	Z = 2
M_r = 302.36	F(000) = 320
Triclinic, P1	D_x = 1.221 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0560 (9) Å	Cell parameters from 2865 reflections
b = 10.0786 (8) Å	θ = 2.2–25.0°
c = 10.3176 (9) Å	µ = 0.08 mm⁻¹
α = 62.040 (4)°	T = 293 K
β = 79.356 (4)°	Block, colorless
γ = 63.038 (4)°	0.30 × 0.22 × 0.20 mm
V = 822.73 (12) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	2887 independent reflections
Radiation source: fine-focus sealed tube	2315 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω and ϕ scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −11→11
T_min = 0.980, T_max = 0.985	k = −11→11
14086 measured reflections	l = −12→12

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0885P)² + 0.2614P] where P = (F_o² + 2F_c²)/3
2887 reflections	(Δ/σ)_max = 0.037
210 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₀H₁₈N₂O	γ = 63.038 (4)°
M_r = 302.36	V = 822.73 (12) Å³
Triclinic, P1	Z = 2
a = 10.0560 (9) Å	Mo Kα radiation
b = 10.0786 (8) Å	µ = 0.08 mm⁻¹
c = 10.3176 (9) Å	T = 293 K
α = 62.040 (4)°	0.30 × 0.22 × 0.20 mm
β = 79.356 (4)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2887 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	2315 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.985	R_int = 0.035
14086 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
2887 reflections	Δρ_min = −0.23 e Å⁻³
210 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
O1	0.67828 (17)	0.53579 (18)	0.72181 (16)	0.0625 (4)
N1	0.60777 (16)	0.58095 (17)	0.26253 (16)	0.0432 (4)
N2	0.68095 (16)	0.41223 (17)	0.31521 (16)	0.0427 (4)
C3	0.69279 (19)	0.3841 (2)	0.19979 (19)	0.0416 (4)
C4	0.6304 (2)	0.5334 (2)	0.0717 (2)	0.0519 (5)
H4	0.6267	0.5457	−0.0229	0.062*
C5	0.5774 (2)	0.6543 (2)	0.1158 (2)	0.0515 (5)
H5	0.5288	0.7675	0.0565	0.062*
C6	0.57725 (18)	0.6542 (2)	0.35731 (19)	0.0400 (4)
C7	0.45725 (19)	0.8246 (2)	0.30619 (18)	0.0396 (4)
C8	0.3162 (2)	0.8596 (2)	0.2667 (2)	0.0450 (4)
H8	0.2986	0.7771	0.2657	0.054*
C9	0.2021 (2)	1.0156 (2)	0.2292 (2)	0.0477 (5)
H9	0.1077	1.0364	0.2051	0.057*
C10	0.2255 (2)	1.1425 (2)	0.2264 (2)	0.0472 (5)
C11	0.3665 (2)	1.1077 (2)	0.2624 (2)	0.0490 (5)
H11	0.3847	1.1916	0.2597	0.059*
C12	0.4818 (2)	0.9513 (2)	0.3023 (2)	0.0451 (4)
H12	0.5759	0.9308	0.3267	0.054*
C13	0.1000 (3)	1.3122 (3)	0.1849 (3)	0.0705 (6)
H13A	0.1319	1.3799	0.2011	0.106*
H13B	0.0158	1.3034	0.2439	0.106*
H13C	0.0719	1.3618	0.0831	0.106*
C14	0.65218 (19)	0.5672 (2)	0.48724 (19)	0.0439 (4)
H14	0.7338	0.4666	0.5039	0.053*
C15	0.6144 (2)	0.6193 (2)	0.6020 (2)	0.0465 (4)
H15	0.5367	0.7228	0.5837	0.056*
C16	0.75914 (19)	0.2135 (2)	0.21612 (19)	0.0431 (4)
C17	0.8059 (2)	0.0785 (2)	0.3526 (2)	0.0541 (5)
H17	0.7965	0.0953	0.4357	0.065*
C18	0.8664 (2)	−0.0813 (3)	0.3660 (2)	0.0600 (5)
H18	0.8978	−0.1702	0.4583	0.072*
C19	0.8812 (2)	−0.1120 (3)	0.2463 (3)	0.0563 (5)
C20	0.8340 (2)	0.0235 (3)	0.1112 (3)	0.0614 (6)
H20	0.8430	0.0064	0.0284	0.074*
C21	0.7740 (2)	0.1837 (3)	0.0956 (2)	0.0548 (5)
H21	0.7432	0.2722	0.0029	0.066*
C22	0.9457 (3)	−0.2851 (3)	0.2607 (3)	0.0817 (8)
H22A	0.9448	−0.3606	0.3615	0.123*
H22B	1.0465	−0.3148	0.2285	0.123*
H22C	0.8869	−0.2905	0.2013	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0725 (10)	0.0569 (9)	0.0525 (9)	−0.0170 (7)	−0.0167 (7)	−0.0231 (7)
N1	0.0508 (9)	0.0338 (8)	0.0399 (8)	−0.0144 (6)	−0.0021 (6)	−0.0144 (6)
N2	0.0462 (8)	0.0361 (8)	0.0409 (8)	−0.0128 (6)	−0.0014 (6)	−0.0167 (6)
C3	0.0412 (9)	0.0424 (10)	0.0394 (9)	−0.0158 (8)	0.0026 (7)	−0.0187 (8)
C4	0.0643 (12)	0.0491 (11)	0.0379 (10)	−0.0213 (9)	0.0008 (8)	−0.0182 (8)
C5	0.0641 (12)	0.0397 (10)	0.0405 (10)	−0.0178 (9)	−0.0035 (8)	−0.0119 (8)
C6	0.0423 (9)	0.0363 (9)	0.0435 (9)	−0.0187 (8)	0.0016 (7)	−0.0173 (7)
C7	0.0441 (9)	0.0334 (9)	0.0386 (9)	−0.0171 (7)	−0.0002 (7)	−0.0127 (7)
C8	0.0505 (10)	0.0400 (10)	0.0487 (10)	−0.0225 (8)	−0.0043 (8)	−0.0172 (8)
C9	0.0428 (10)	0.0464 (10)	0.0493 (10)	−0.0182 (8)	−0.0047 (8)	−0.0161 (8)
C10	0.0526 (11)	0.0360 (9)	0.0432 (10)	−0.0146 (8)	−0.0030 (8)	−0.0121 (8)
C11	0.0620 (12)	0.0333 (9)	0.0515 (11)	−0.0230 (9)	−0.0056 (9)	−0.0131 (8)
C12	0.0458 (10)	0.0401 (10)	0.0494 (10)	−0.0220 (8)	−0.0037 (8)	−0.0140 (8)
C13	0.0647 (14)	0.0433 (12)	0.0827 (16)	−0.0084 (10)	−0.0120 (11)	−0.0206 (11)
C14	0.0445 (10)	0.0376 (9)	0.0472 (10)	−0.0147 (8)	−0.0026 (8)	−0.0179 (8)
C15	0.0504 (10)	0.0400 (10)	0.0494 (11)	−0.0177 (8)	−0.0057 (8)	−0.0185 (8)
C16	0.0397 (9)	0.0449 (10)	0.0449 (10)	−0.0164 (8)	0.0043 (7)	−0.0224 (8)
C17	0.0643 (12)	0.0479 (11)	0.0458 (11)	−0.0184 (9)	0.0031 (9)	−0.0231 (9)
C18	0.0643 (13)	0.0425 (11)	0.0598 (13)	−0.0175 (10)	0.0041 (10)	−0.0179 (9)
C19	0.0412 (10)	0.0528 (12)	0.0819 (15)	−0.0178 (9)	0.0089 (9)	−0.0391 (11)
C20	0.0588 (12)	0.0667 (14)	0.0698 (14)	−0.0182 (11)	0.0022 (10)	−0.0463 (12)
C21	0.0574 (12)	0.0539 (12)	0.0506 (11)	−0.0145 (9)	−0.0029 (9)	−0.0280 (9)
C22	0.0724 (16)	0.0617 (15)	0.123 (2)	−0.0251 (12)	0.0162 (15)	−0.0569 (16)

Geometric parameters (Å, º) top

O1—C15	1.215 (2)	C12—H12	0.9300
N1—C5	1.360 (2)	C13—H13A	0.9600
N1—N2	1.369 (2)	C13—H13B	0.9600
N1—C6	1.399 (2)	C13—H13C	0.9600
N2—C3	1.321 (2)	C14—C15	1.435 (3)
C3—C4	1.411 (3)	C14—H14	0.9300
C3—C16	1.469 (2)	C15—H15	0.9300
C4—C5	1.348 (3)	C16—C21	1.379 (3)
C4—H4	0.9300	C16—C17	1.387 (3)
C5—H5	0.9300	C17—C18	1.384 (3)
C6—C14	1.344 (2)	C17—H17	0.9300
C6—C7	1.480 (2)	C18—C19	1.375 (3)
C7—C12	1.388 (2)	C18—H18	0.9300
C7—C8	1.388 (2)	C19—C20	1.380 (3)
C8—C9	1.377 (3)	C19—C22	1.501 (3)
C8—H8	0.9300	C20—C21	1.380 (3)
C9—C10	1.388 (3)	C20—H20	0.9300
C9—H9	0.9300	C21—H21	0.9300
C10—C11	1.376 (3)	C22—H22A	0.9600
C10—C13	1.503 (3)	C22—H22B	0.9600
C11—C12	1.382 (3)	C22—H22C	0.9600
C11—H11	0.9300

C5—N1—N2	110.87 (14)	C10—C13—H13B	109.5
C5—N1—C6	129.15 (15)	H13A—C13—H13B	109.5
N2—N1—C6	119.97 (14)	C10—C13—H13C	109.5
C3—N2—N1	104.85 (14)	H13A—C13—H13C	109.5
N2—C3—C4	111.37 (16)	H13B—C13—H13C	109.5
N2—C3—C16	120.39 (16)	C6—C14—C15	124.24 (16)
C4—C3—C16	128.20 (16)	C6—C14—H14	117.9
C5—C4—C3	105.21 (17)	C15—C14—H14	117.9
C5—C4—H4	127.4	O1—C15—C14	123.68 (17)
C3—C4—H4	127.4	O1—C15—H15	118.2
C4—C5—N1	107.70 (16)	C14—C15—H15	118.2
C4—C5—H5	126.2	C21—C16—C17	118.12 (17)
N1—C5—H5	126.2	C21—C16—C3	120.56 (17)
C14—C6—N1	119.58 (15)	C17—C16—C3	121.31 (16)
C14—C6—C7	124.72 (15)	C18—C17—C16	120.45 (19)
N1—C6—C7	115.65 (14)	C18—C17—H17	119.8
C12—C7—C8	118.61 (16)	C16—C17—H17	119.8
C12—C7—C6	120.61 (15)	C19—C18—C17	121.7 (2)
C8—C7—C6	120.73 (15)	C19—C18—H18	119.1
C9—C8—C7	120.48 (16)	C17—C18—H18	119.1
C9—C8—H8	119.8	C18—C19—C20	117.22 (19)
C7—C8—H8	119.8	C18—C19—C22	121.8 (2)
C8—C9—C10	121.20 (17)	C20—C19—C22	120.9 (2)
C8—C9—H9	119.4	C19—C20—C21	121.90 (19)
C10—C9—H9	119.4	C19—C20—H20	119.1
C11—C10—C9	117.95 (17)	C21—C20—H20	119.1
C11—C10—C13	121.45 (18)	C16—C21—C20	120.6 (2)
C9—C10—C13	120.60 (18)	C16—C21—H21	119.7
C10—C11—C12	121.59 (17)	C20—C21—H21	119.7
C10—C11—H11	119.2	C19—C22—H22A	109.5
C12—C11—H11	119.2	C19—C22—H22B	109.5
C11—C12—C7	120.15 (16)	H22A—C22—H22B	109.5
C11—C12—H12	119.9	C19—C22—H22C	109.5
C7—C12—H12	119.9	H22A—C22—H22C	109.5
C10—C13—H13A	109.5	H22B—C22—H22C	109.5

C5—N1—N2—C3	−0.79 (19)	C9—C10—C11—C12	−1.0 (3)
C6—N1—N2—C3	−179.57 (15)	C13—C10—C11—C12	179.22 (19)
N1—N2—C3—C4	1.1 (2)	C10—C11—C12—C7	0.4 (3)
N1—N2—C3—C16	−176.65 (15)	C8—C7—C12—C11	1.1 (3)
N2—C3—C4—C5	−1.1 (2)	C6—C7—C12—C11	−176.32 (16)
C16—C3—C4—C5	176.50 (18)	N1—C6—C14—C15	−169.74 (16)
C3—C4—C5—N1	0.5 (2)	C7—C6—C14—C15	7.8 (3)
N2—N1—C5—C4	0.1 (2)	C6—C14—C15—O1	176.16 (18)
C6—N1—C5—C4	178.78 (17)	N2—C3—C16—C21	−178.92 (17)
C5—N1—C6—C14	−160.85 (19)	C4—C3—C16—C21	3.7 (3)
N2—N1—C6—C14	17.7 (2)	N2—C3—C16—C17	2.4 (3)
C5—N1—C6—C7	21.4 (3)	C4—C3—C16—C17	−175.02 (19)
N2—N1—C6—C7	−160.09 (14)	C21—C16—C17—C18	0.4 (3)
C14—C6—C7—C12	54.5 (2)	C3—C16—C17—C18	179.17 (18)
N1—C6—C7—C12	−127.83 (17)	C16—C17—C18—C19	−0.5 (3)
C14—C6—C7—C8	−122.9 (2)	C17—C18—C19—C20	0.4 (3)
N1—C6—C7—C8	54.8 (2)	C17—C18—C19—C22	−179.5 (2)
C12—C7—C8—C9	−2.0 (3)	C18—C19—C20—C21	−0.1 (3)
C6—C7—C8—C9	175.42 (16)	C22—C19—C20—C21	179.7 (2)
C7—C8—C9—C10	1.4 (3)	C17—C16—C21—C20	−0.2 (3)
C8—C9—C10—C11	0.1 (3)	C3—C16—C21—C20	−178.93 (17)
C8—C9—C10—C13	179.87 (19)	C19—C20—C21—C16	0.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22B···O1ⁱ	0.96	2.60	3.446 (3)	148
C9—H9···Cg1ⁱⁱ	0.93	2.80	3.690 (3)	161

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₂O
M_r	302.36
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.0560 (9), 10.0786 (8), 10.3176 (9)
α, β, γ (°)	62.040 (4), 79.356 (4), 63.038 (4)
V (Å³)	822.73 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.22 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.980, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	14086, 2887, 2315
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.154, 1.03
No. of reflections	2887
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.23

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22B···O1ⁱ	0.96	2.60	3.446 (3)	147.6
C9—H9···Cg1ⁱⁱ	0.93	2.80	3.690 (3)	161

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

Acknowledgements

PR thanks Dr Babu Varghese, SAIF, IIT, Madras, India, for his help with the data collection.

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 (2004). APEX2 and SAINT. 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
Cordell, G. (1981). Introduction to Alkaloids: A Biogenic Approach. New York: Wiley International. Google Scholar
Cottineau, B., Toto, P., Marot, C., Pipaud, A. & Chenault, J. (2002). Bioorg. Med. Chem. 12, 2105–2108. CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals 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. 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. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar