1-[(E)-2-Formyl-1-(4-methyl­phen­yl)ethen­yl]-3-(4-methyl­phen­yl)pyrazole-4-carbaldehyde

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

doi:10.1107/S1600536808027694

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1889

doi:10.1107/S1600536808027694

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1-[(E)-2-Formyl-1-(4-methylphenyl)ethenyl]-3-(4-methylphenyl)pyrazole-4-carbaldehyde

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 20 August 2008; accepted 28 August 2008; online 6 September 2008)

In the crystal structure of the title compound, C₂₁H₁₈N₂O₂, molecules are linked through C—H⋯O interactions. Two symmetry-related molecules form a cyclic centrosymmetric R₂²(20) dimer. These dimers are further connected into chains running along the b axis.

Related literature

For related literature, see: Baraldi et al. (1998 ); Bernstein et al. (1995 ); Bruno et al. (1990 ); Chen & Li (1998 ); Cottineau et al. (2002 ); Londershausen (1996 ); Mishra et al. (1998 ); Smith et al. (2001 ).

Experimental

Crystal data

C₂₁H₁₈N₂O₂
M_r = 330.37
Monoclinic, P 2₁ /n
a = 10.2914 (4) Å
b = 15.3618 (5) Å
c = 11.0271 (4) Å
β = 98.778 (1)°
V = 1722.90 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.30 × 0.20 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.980, T_max = 0.987
24747 measured reflections
6019 independent reflections
3731 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.174
S = 1.04
6019 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22A⋯O2ⁱ	0.96	2.60	3.378 (2)	139
C5—H5⋯O1ⁱⁱ	0.93	2.23	3.1094 (17)	159
Symmetry codes: (i) -x+3, -y, -z; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536808027694/bt2774sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027694/bt2774Isup2.hkl

checkCIF report

Comment top

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

The pyrazole ring A and methylphenyl ring C are near-coplanar with the inter-ring dihedral angle of 17.08 (7)°, whereas the pyrazole ring is twisted from the methylphenyl ring B as can be seen from the dihedral angle of 79.70 (8)°. The propenal group assumes an extended conformation which is evidenced from the torsion angle of [N1—C6—C14—C15] -175.47 (12)°.

The crystal structure is stabilized by C—H···O type of intermolecular interactions. Atom C5 at (x, y, z) donates a proton to atom O1 at (3/2 - x,-1/2 + y,1/2 - z) form a one dimensional C7 chain (Bernstein et al. 1995) running along b axis. The molecules at positions (x, y, z) and (3 - x, -y, -z) form a cyclic centrosymmetric R₂²(20) dimer through C22—H22A···O2 hydrogen bonds.

Related literature top

For related literature, see: Baraldi et al. (1998); Bernstein et al. (1995); Bruno et al. (1990); Chen & Li (1998); Cottineau et al. (2002); Londershausen (1996); Mishra et al. (1998); Smith et al. (2001).

Experimental top

A 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 rectystalized in dichloromethane to obtain 3-(4-methylphenyl)-1-[(E)-1-(4-methylphenyl) -3-oxo-1-propenyl]-1H-pyrazole-4-carbaldehyde in 57% 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 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. Perspective view of the molecules showing the thermal ellipsoids are drawn at 50% probability level. The H atoms are shown as small circles of arbitrary radii.
	Fig. 2. Perspective view of the crystal packing showing hydrogen-bond interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

1-[(E)-2-Formyl-1-(4-methylphenyl)ethenyl]-3-(4-methylphenyl)pyrazole- 4-carbaldehyde top

Crystal data top

C₂₁H₁₈N₂O₂	F(000) = 696
M_r = 330.37	D_x = 1.274 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4580 reflections
a = 10.2914 (4) Å	θ = 2.3–32.2°
b = 15.3618 (5) Å	µ = 0.08 mm⁻¹
c = 11.0271 (4) Å	T = 293 K
β = 98.778 (1)°	Block, colorless
V = 1722.90 (11) Å³	0.30 × 0.20 × 0.16 mm
Z = 4

Data collection top

Bruker APEX2 CCD area-detector diffractometer	6019 independent reflections
Radiation source: fine-focus sealed tube	3731 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω and ϕ scans	θ_max = 32.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −9→15
T_min = 0.980, T_max = 0.987	k = −22→19
24747 measured reflections	l = −16→16

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0833P)² + 0.2417P] where P = (F_o² + 2F_c²)/3
6019 reflections	(Δ/σ)_max = 0.037
228 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₁H₁₈N₂O₂	V = 1722.90 (11) Å³
M_r = 330.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.2914 (4) Å	µ = 0.08 mm⁻¹
b = 15.3618 (5) Å	T = 293 K
c = 11.0271 (4) Å	0.30 × 0.20 × 0.16 mm
β = 98.778 (1)°

Data collection top

Bruker APEX2 CCD area-detector diffractometer	6019 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3731 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.987	R_int = 0.025
24747 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 1.04	Δρ_max = 0.35 e Å⁻³
6019 reflections	Δρ_min = −0.30 e Å⁻³
228 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	0.65358 (11)	0.31462 (7)	0.28639 (13)	0.0678 (3)
O2	1.23915 (18)	−0.09914 (9)	0.0928 (2)	0.1340 (9)
N1	0.93785 (9)	0.08384 (7)	0.22048 (10)	0.0378 (2)
N2	1.03155 (10)	0.13820 (7)	0.18711 (10)	0.0395 (2)
C3	1.12006 (11)	0.08674 (8)	0.14811 (11)	0.0367 (3)
C4	1.08139 (12)	−0.00258 (8)	0.15437 (12)	0.0413 (3)
C5	0.96509 (12)	−0.00004 (8)	0.20099 (12)	0.0401 (3)
H5	0.9144	−0.0478	0.2163	0.048*
C6	0.82656 (11)	0.11747 (8)	0.26494 (11)	0.0367 (3)
C7	0.75369 (11)	0.05214 (8)	0.32683 (12)	0.0381 (3)
C8	0.80708 (14)	0.01954 (10)	0.44021 (14)	0.0509 (3)
H8	0.8884	0.0396	0.4784	0.061*
C9	0.74082 (17)	−0.04269 (11)	0.49748 (15)	0.0593 (4)
H9	0.7777	−0.0632	0.5744	0.071*
C10	0.62160 (17)	−0.07477 (10)	0.44295 (16)	0.0594 (4)
C11	0.56858 (16)	−0.04197 (12)	0.33110 (18)	0.0648 (5)
H11	0.4876	−0.0627	0.2931	0.078*
C12	0.63277 (14)	0.02175 (11)	0.27265 (14)	0.0527 (4)
H12	0.5940	0.0437	0.1971	0.063*
C13	0.5526 (2)	−0.14496 (13)	0.5044 (2)	0.0956 (8)
H13A	0.4601	−0.1432	0.4741	0.143*
H13B	0.5667	−0.1356	0.5915	0.143*
H13C	0.5872	−0.2008	0.4867	0.143*
C14	0.79599 (12)	0.20179 (9)	0.25103 (13)	0.0438 (3)
H14	0.8454	0.2369	0.2066	0.053*
C15	0.68876 (13)	0.24017 (10)	0.30271 (14)	0.0487 (3)
H15	0.6441	0.2053	0.3516	0.058*
C16	1.23610 (11)	0.12790 (9)	0.10905 (12)	0.0386 (3)
C17	1.26700 (13)	0.21329 (10)	0.14214 (14)	0.0497 (3)
H17	1.2159	0.2431	0.1911	0.060*
C18	1.37242 (14)	0.25480 (10)	0.10352 (15)	0.0527 (4)
H18	1.3910	0.3122	0.1268	0.063*
C19	1.45103 (12)	0.21259 (10)	0.03075 (13)	0.0454 (3)
C20	1.42132 (13)	0.12763 (10)	−0.00071 (14)	0.0503 (3)
H20	1.4736	0.0978	−0.0486	0.060*
C21	1.31552 (13)	0.08512 (10)	0.03692 (13)	0.0475 (3)
H21	1.2976	0.0276	0.0137	0.057*
C22	1.56456 (14)	0.25876 (12)	−0.01291 (16)	0.0582 (4)
H22A	1.6425	0.2240	0.0057	0.087*
H22B	1.5783	0.3140	0.0277	0.087*
H22C	1.5451	0.2677	−0.1000	0.087*
C23	1.13601 (18)	−0.08585 (10)	0.12661 (19)	0.0684 (5)
H23	1.0849	−0.1346	0.1362	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0641 (7)	0.0420 (7)	0.0968 (9)	0.0162 (5)	0.0110 (6)	−0.0076 (6)
O2	0.1215 (13)	0.0506 (8)	0.263 (2)	0.0205 (8)	0.1355 (15)	0.0071 (11)
N1	0.0371 (5)	0.0308 (5)	0.0488 (6)	0.0001 (4)	0.0169 (4)	0.0010 (4)
N2	0.0387 (5)	0.0325 (6)	0.0508 (6)	−0.0020 (4)	0.0180 (4)	0.0002 (4)
C3	0.0366 (5)	0.0355 (7)	0.0399 (6)	0.0009 (4)	0.0117 (4)	0.0008 (5)
C4	0.0424 (6)	0.0353 (7)	0.0493 (7)	0.0019 (5)	0.0171 (5)	−0.0013 (5)
C5	0.0433 (6)	0.0298 (6)	0.0502 (7)	−0.0006 (5)	0.0167 (5)	−0.0007 (5)
C6	0.0337 (5)	0.0343 (6)	0.0442 (6)	0.0010 (4)	0.0129 (5)	0.0013 (5)
C7	0.0373 (5)	0.0332 (6)	0.0470 (7)	0.0008 (4)	0.0166 (5)	0.0000 (5)
C8	0.0489 (7)	0.0486 (8)	0.0561 (8)	0.0020 (6)	0.0110 (6)	0.0086 (6)
C9	0.0766 (10)	0.0492 (9)	0.0572 (9)	0.0087 (8)	0.0266 (8)	0.0136 (7)
C10	0.0757 (10)	0.0409 (8)	0.0730 (11)	−0.0059 (7)	0.0476 (8)	−0.0042 (7)
C11	0.0556 (8)	0.0655 (11)	0.0784 (12)	−0.0242 (8)	0.0266 (8)	−0.0120 (9)
C12	0.0471 (7)	0.0578 (9)	0.0545 (8)	−0.0103 (6)	0.0115 (6)	0.0000 (7)
C13	0.1297 (19)	0.0620 (12)	0.1154 (18)	−0.0239 (12)	0.0837 (15)	−0.0010 (11)
C14	0.0411 (6)	0.0357 (7)	0.0578 (8)	0.0027 (5)	0.0176 (6)	0.0040 (6)
C15	0.0424 (6)	0.0409 (8)	0.0647 (9)	0.0053 (5)	0.0145 (6)	−0.0028 (6)
C16	0.0360 (5)	0.0412 (7)	0.0404 (6)	−0.0007 (5)	0.0113 (5)	0.0016 (5)
C17	0.0474 (7)	0.0471 (8)	0.0599 (9)	−0.0060 (6)	0.0247 (6)	−0.0076 (6)
C18	0.0500 (7)	0.0461 (8)	0.0661 (9)	−0.0105 (6)	0.0221 (7)	−0.0054 (7)
C19	0.0356 (6)	0.0564 (9)	0.0455 (7)	−0.0020 (5)	0.0102 (5)	0.0086 (6)
C20	0.0445 (7)	0.0573 (9)	0.0537 (8)	0.0025 (6)	0.0216 (6)	−0.0006 (6)
C21	0.0459 (7)	0.0447 (8)	0.0556 (8)	−0.0015 (5)	0.0198 (6)	−0.0052 (6)
C22	0.0425 (7)	0.0709 (11)	0.0644 (9)	−0.0070 (7)	0.0180 (6)	0.0116 (8)
C23	0.0755 (11)	0.0359 (8)	0.1052 (14)	0.0070 (7)	0.0502 (10)	0.0005 (8)

Geometric parameters (Å, º) top

O1—C15	1.2048 (17)	C12—H12	0.9300
O2—C23	1.1949 (19)	C13—H13A	0.9600
N1—C5	1.3429 (16)	C13—H13B	0.9600
N1—N2	1.3679 (13)	C13—H13C	0.9600
N1—C6	1.4108 (14)	C14—C15	1.4429 (17)
N2—C3	1.3263 (15)	C14—H14	0.9300
C3—C4	1.4332 (18)	C15—H15	0.9300
C3—C16	1.4726 (16)	C16—C17	1.386 (2)
C4—C5	1.3734 (16)	C16—C21	1.3896 (17)
C4—C23	1.449 (2)	C17—C18	1.3806 (18)
C5—H5	0.9300	C17—H17	0.9300
C6—C14	1.3364 (18)	C18—C19	1.384 (2)
C6—C7	1.4804 (16)	C18—H18	0.9300
C7—C12	1.3771 (19)	C19—C20	1.373 (2)
C7—C8	1.3807 (19)	C19—C22	1.5072 (17)
C8—C9	1.382 (2)	C20—C21	1.3864 (18)
C8—H8	0.9300	C20—H20	0.9300
C9—C10	1.373 (3)	C21—H21	0.9300
C9—H9	0.9300	C22—H22A	0.9600
C10—C11	1.367 (3)	C22—H22B	0.9600
C10—C13	1.507 (2)	C22—H22C	0.9600
C11—C12	1.393 (2)	C23—H23	0.9300
C11—H11	0.9300

C5—N1—N2	111.71 (9)	C10—C13—H13C	109.5
C5—N1—C6	127.40 (10)	H13A—C13—H13C	109.5
N2—N1—C6	120.86 (10)	H13B—C13—H13C	109.5
C3—N2—N1	105.69 (10)	C6—C14—C15	122.12 (12)
N2—C3—C4	110.22 (10)	C6—C14—H14	118.9
N2—C3—C16	117.81 (11)	C15—C14—H14	118.9
C4—C3—C16	131.96 (11)	O1—C15—C14	124.02 (14)
C5—C4—C3	104.78 (11)	O1—C15—H15	118.0
C5—C4—C23	119.51 (13)	C14—C15—H15	118.0
C3—C4—C23	135.70 (12)	C17—C16—C21	117.85 (11)
N1—C5—C4	107.59 (11)	C17—C16—C3	119.56 (11)
N1—C5—H5	126.2	C21—C16—C3	122.58 (12)
C4—C5—H5	126.2	C18—C17—C16	121.04 (12)
C14—C6—N1	120.30 (11)	C18—C17—H17	119.5
C14—C6—C7	125.66 (10)	C16—C17—H17	119.5
N1—C6—C7	114.03 (10)	C17—C18—C19	121.24 (14)
C12—C7—C8	118.58 (12)	C17—C18—H18	119.4
C12—C7—C6	121.17 (12)	C19—C18—H18	119.4
C8—C7—C6	120.25 (11)	C20—C19—C18	117.67 (12)
C7—C8—C9	120.59 (14)	C20—C19—C22	121.35 (13)
C7—C8—H8	119.7	C18—C19—C22	120.99 (14)
C9—C8—H8	119.7	C19—C20—C21	121.80 (12)
C10—C9—C8	121.24 (15)	C19—C20—H20	119.1
C10—C9—H9	119.4	C21—C20—H20	119.1
C8—C9—H9	119.4	C20—C21—C16	120.39 (14)
C11—C10—C9	118.04 (14)	C20—C21—H21	119.8
C11—C10—C13	121.26 (18)	C16—C21—H21	119.8
C9—C10—C13	120.70 (19)	C19—C22—H22A	109.5
C10—C11—C12	121.64 (15)	C19—C22—H22B	109.5
C10—C11—H11	119.2	H22A—C22—H22B	109.5
C12—C11—H11	119.2	C19—C22—H22C	109.5
C7—C12—C11	119.90 (15)	H22A—C22—H22C	109.5
C7—C12—H12	120.1	H22B—C22—H22C	109.5
C11—C12—H12	120.1	O2—C23—C4	127.49 (16)
C10—C13—H13A	109.5	O2—C23—H23	116.3
C10—C13—H13B	109.5	C4—C23—H23	116.3
H13A—C13—H13B	109.5

C5—N1—N2—C3	−1.10 (14)	C9—C10—C11—C12	0.4 (2)
C6—N1—N2—C3	−178.96 (11)	C13—C10—C11—C12	−178.80 (16)
N1—N2—C3—C4	1.07 (14)	C8—C7—C12—C11	−1.4 (2)
N1—N2—C3—C16	−178.26 (10)	C6—C7—C12—C11	177.74 (13)
N2—C3—C4—C5	−0.68 (15)	C10—C11—C12—C7	1.0 (3)
C16—C3—C4—C5	178.52 (13)	N1—C6—C14—C15	−175.47 (12)
N2—C3—C4—C23	−179.31 (18)	C7—C6—C14—C15	3.5 (2)
C16—C3—C4—C23	−0.1 (3)	C6—C14—C15—O1	−175.65 (15)
N2—N1—C5—C4	0.69 (15)	N2—C3—C16—C17	16.27 (18)
C6—N1—C5—C4	178.37 (12)	C4—C3—C16—C17	−162.88 (14)
C3—C4—C5—N1	−0.02 (15)	N2—C3—C16—C21	−162.11 (13)
C23—C4—C5—N1	178.89 (14)	C4—C3—C16—C21	18.7 (2)
C5—N1—C6—C14	−163.17 (14)	C21—C16—C17—C18	0.7 (2)
N2—N1—C6—C14	14.31 (18)	C3—C16—C17—C18	−177.75 (13)
C5—N1—C6—C7	17.72 (18)	C16—C17—C18—C19	−0.2 (2)
N2—N1—C6—C7	−164.79 (11)	C17—C18—C19—C20	−0.7 (2)
C14—C6—C7—C12	72.91 (19)	C17—C18—C19—C22	178.93 (14)
N1—C6—C7—C12	−108.04 (14)	C18—C19—C20—C21	0.9 (2)
C14—C6—C7—C8	−107.93 (16)	C22—C19—C20—C21	−178.68 (13)
N1—C6—C7—C8	71.12 (15)	C19—C20—C21—C16	−0.4 (2)
C12—C7—C8—C9	0.5 (2)	C17—C16—C21—C20	−0.5 (2)
C6—C7—C8—C9	−178.73 (13)	C3—C16—C21—C20	177.95 (12)
C7—C8—C9—C10	1.0 (2)	C5—C4—C23—O2	−175.2 (2)
C8—C9—C10—C11	−1.4 (2)	C3—C4—C23—O2	3.3 (4)
C8—C9—C10—C13	177.79 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22A···O2ⁱ	0.96	2.60	3.378 (2)	139
C5—H5···O1ⁱⁱ	0.93	2.23	3.1094 (17)	159

Symmetry codes: (i) −x+3, −y, −z; (ii) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈N₂O₂
M_r	330.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.2914 (4), 15.3618 (5), 11.0271 (4)
β (°)	98.778 (1)
V (Å³)	1722.90 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.16

Data collection
Diffractometer	Bruker APEX2 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.980, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	24747, 6019, 3731
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.752

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.174, 1.04
No. of reflections	6019
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.30

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP (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—H22A···O2ⁱ	0.96	2.60	3.378 (2)	138.7
C5—H5···O1ⁱⁱ	0.93	2.23	3.1094 (17)	158.5

Symmetry codes: (i) −x+3, −y, −z; (ii) −x+3/2, y−1/2, −z+1/2.

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

1-[(E)-2-Formyl-1-(4-methyl­phen­yl)ethen­yl]-3-(4-methyl­phen­yl)pyrazole-4-carbaldehyde

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-[(E)-2-Formyl-1-(4-methylphenyl)ethenyl]-3-(4-methylphenyl)pyrazole-4-carbaldehyde