(E)-3-(4-Meth­oxy­phen­yl)-3-[3-(4-meth­oxy­phen­yl)-1H-pyrazol-1-yl]prop-2-enal

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

doi:10.1107/S1600536813007678

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Pages o594-o595

doi:10.1107/S1600536813007678

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(E)-3-(4-Methoxyphenyl)-3-[3-(4-methoxyphenyl)-1H-pyrazol-1-yl]prop-2-enal

V. Susindran,^a S. Athimoolam,^b ^* S. Asath Bahadur,^c R. Manikannan ^d 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 Region, Nagercoil 629 004, India, ^cDepartment of Physics, Kalasalingam University, Anand Nagar, Krishnan Koil 626 190, India, ^dInstitute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Pardubice 53210, Czech Republic, and ^eDepartment of Organic Chemistry, Madurai Kamaraj University, Madurai 625 021, India
^*Correspondence e-mail: athi81s@yahoo.co.in

(Received 15 March 2013; accepted 20 March 2013; online 28 March 2013)

In the title molecule, C₂₀H₁₈N₂O₃, the pyrazole ring forms a dihedral angle of 2.2 (1)° with its methoxyphenyl substituent and a dihedral angle of 67.2 (1)° with the benzene substituent on the propenal unit. In the crystal, molecules are connected by weak C—H⋯O hydrogen bonds, forming R₂²(26) and R₂²(28) cyclic dimers that lie about crystallographic inversion centres. These dimers are further linked through C—H⋯O and C—H⋯N hydrogen bonds, forming C(8), C(9), C(10) and C(16) chain motifs. These primary motifs are further linked to form secondary C₂²(15) chains and R₂²(18) rings.

Related literature

For the pharmacological and medicinal properties of pyrazole compounds, 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 structures, see: Susindran et al. (2010a ,b , 2012 ). For hydrogen-bond motifs, see: Etter et al. (1990 ).

Experimental

Crystal data

C₂₀H₁₈N₂O₃
M_r = 334.36
Triclinic, $[P \overline 1]$
a = 8.8081 (6) Å
b = 9.8474 (5) Å
c = 10.3292 (8) Å
α = 94.997 (12)°
β = 93.811 (14)°
γ = 106.719 (13)°
V = 850.85 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.22 × 0.19 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer
8253 measured reflections
2993 independent reflections
2677 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.107
S = 1.04
2993 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3ⁱ	0.93	2.73	3.366 (2)	126
C18—H18C⋯N2ⁱ	0.96	2.74	3.627 (2)	155
C14—H14⋯O2ⁱⁱ	0.93	2.49	3.301 (2)	145
C33—H33⋯O1ⁱⁱⁱ	0.93	2.82	3.642 (2)	148
C37—H37B⋯O2^iv	0.96	2.75	3.688 (2)	166
C37—H37C⋯O1^v	0.96	2.76	3.650 (2)	155
Symmetry codes: (i) x, y-1, z; (ii) x+1, y, z; (iii) -x+2, -y+1, -z+1; (iv) -x+1, -y+2, -z+1; (v) x, y+1, z-1.

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813007678/sj5307sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813007678/sj5307Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813007678/sj5307Isup3.cml

checkCIF report

Comment top

Pyrazoles are classified as both aromatic ring compounds and heterocyclic compounds and are characterized by a 5-membered ring structure composed of three carbon atoms and two nitrogen atoms in adjacent positions in 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 have been 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. Based on the above specifics and also as part of our continuing work on pyrazole related compounds (Susindran et al., 2010a,b, 2012), we report here the structure of the title pyrazole derivative.

The molecular structure of the title compound is shown in Fig. 1. The phenyl rings of the methoxyphenyl groups and the plane of the pyrazole ring form dihedral angles of 2.2 (1)° (with the C31—C36 ring) and 67.2 (1)° (with the C12—C17 ring). The crystal packing is stabilized through weak intermolecular C—H···O and C—H···N interactions (Table 1). Molecules are connected around inversion centres of the unit cell making R₂²(26) and R₂²(28) ring motifs (Etter et al., 1990) through C33—H33···O1 and C37—H37B···O2 interactions, respectively. These pairs of dimeric rings are further connected in a head-to-tail fashion by C37—H37B···O2 and C33—H33···O1 contacts, Table 1, to generate sheets of dimers approximately parallel to (112). These contacts also generate C₂²(15) chains in the ab-plane, Fig 2.

Additional chains are generated in the crystal as follows. A C(8) chain forms along the a-axis through a C14—H14···O2 interaction (Fig. 3) while C5—H5···O3 and C18—H18C···N2 contacts generate C(9) and C(10) chains along b. A combination of these contacts also generate an R₂²(18) ring motif (Fig. 4). Finally a C(16) chain of molecules linked in a head to tail fashion forms along the bc diagonal through a C37—H37C···O1 contact, Fig 5.

Related literature top

For the pharmacological and medicinal properties of pyrazole compounds, 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 structures, see: Susindran et al. (2010a,b, 2012). For hydrogen-bond motifs, see: Etter et al. (1990).

Experimental top

Phosphorous oxychloride (0.024 mole) was added dropwise over 5 to 10 minutes to a mixture of 1-(4-methoxyphenyl)-1-ethanone N-[(E)-1-(4-methoxyphenyl)ethylidene]hydrazone (0.003 mole) and 3 ml of dimethyl formamide cooled in ice to 0°C. The reaction mixture was then irradiated with microwaves for 30 sec. The progress 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 products were separated by column chromatography using petroleum ether and ethyl acetate mixture (98/2 v/v) as eluent. The title compound was crystallized from dichloromethane.

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 (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids.
	Fig. 2. A view of the primary R₂²(26) and R₂²(28) rings and the secondary C₂²(15) chains.
	Fig. 3. A view of the C(8) chain extending along the a-axis.
	Fig. 4. A view of the primary C(9) and C(10) chains leading to a secondary R₂²(18) ring motif.
	Fig. 5. A view of a C(16) chain motif connecting the molecules in a head-to-tail fashion along the diagonal of the bc-plane.

(E)-3-(4-Methoxyphenyl)-3-[3-(4-methoxyphenyl)-1H-pyrazol-1-yl]prop-2-enal top

Crystal data top

C₂₀H₁₈N₂O₃	Z = 2
M_r = 334.36	F(000) = 352
Triclinic, P1	D_x = 1.305 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8081 (6) Å	Cell parameters from 3011 reflections
b = 9.8474 (5) Å	θ = 2.2–24.3°
c = 10.3292 (8) Å	µ = 0.09 mm⁻¹
α = 94.997 (12)°	T = 293 K
β = 93.811 (14)°	Block, colourless
γ = 106.719 (13)°	0.22 × 0.19 × 0.15 mm
V = 850.85 (10) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	2677 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 25.0°, θ_min = 2.0°
ω scans	h = −10→10
8253 measured reflections	k = −11→11
2993 independent 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.057P)² + 0.1393P] where P = (F_o² + 2F_c²)/3
2993 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₀H₁₈N₂O₃	γ = 106.719 (13)°
M_r = 334.36	V = 850.85 (10) Å³
Triclinic, P1	Z = 2
a = 8.8081 (6) Å	Mo Kα radiation
b = 9.8474 (5) Å	µ = 0.09 mm⁻¹
c = 10.3292 (8) Å	T = 293 K
α = 94.997 (12)°	0.22 × 0.19 × 0.15 mm
β = 93.811 (14)°

Data collection top

Bruker SMART APEX CCD diffractometer	2677 reflections with I > 2σ(I)
8253 measured reflections	R_int = 0.020
2993 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.04	Δρ_max = 0.14 e Å⁻³
2993 reflections	Δρ_min = −0.25 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
N1	0.69002 (13)	0.52763 (11)	0.64078 (11)	0.0457 (3)
N2	0.67831 (13)	0.65931 (12)	0.61936 (11)	0.0462 (3)
C3	0.76448 (15)	0.69626 (14)	0.52034 (12)	0.0422 (3)
C4	0.83041 (17)	0.58717 (15)	0.47685 (14)	0.0509 (3)
H4	0.8947	0.5874	0.4089	0.061*
C5	0.78079 (17)	0.48282 (15)	0.55426 (14)	0.0505 (3)
H5	0.8041	0.3963	0.5496	0.061*
C11	0.60073 (15)	0.45024 (14)	0.73278 (13)	0.0444 (3)
C12	0.66018 (15)	0.33536 (14)	0.77906 (12)	0.0436 (3)
C13	0.81934 (16)	0.36217 (15)	0.82620 (14)	0.0508 (3)
H13	0.8894	0.4532	0.8269	0.061*
C14	0.87420 (17)	0.25667 (16)	0.87148 (14)	0.0527 (4)
H14	0.9807	0.2768	0.9028	0.063*
C15	0.77221 (17)	0.12014 (15)	0.87087 (13)	0.0473 (3)
C16	0.61388 (17)	0.09080 (14)	0.82448 (13)	0.0478 (3)
H16	0.5444	−0.0005	0.8239	0.057*
C17	0.55946 (16)	0.19790 (14)	0.77898 (13)	0.0454 (3)
H17	0.4530	0.1774	0.7476	0.055*
O1	0.84005 (13)	0.02394 (12)	0.91793 (11)	0.0643 (3)
C18	0.7407 (2)	−0.11630 (18)	0.92744 (19)	0.0734 (5)
H18A	0.6562	−0.1113	0.9801	0.110*
H18B	0.8025	−0.1704	0.9669	0.110*
H18C	0.6963	−0.1619	0.8417	0.110*
C31	0.77884 (15)	0.83377 (14)	0.47012 (12)	0.0413 (3)
C32	0.86613 (15)	0.87520 (15)	0.36586 (13)	0.0460 (3)
H32	0.9203	0.8156	0.3287	0.055*
C33	0.87491 (16)	1.00260 (15)	0.31559 (13)	0.0483 (3)
H33	0.9338	1.0277	0.2453	0.058*
C34	0.79545 (16)	1.09256 (14)	0.37054 (13)	0.0459 (3)
C35	0.71081 (17)	1.05416 (15)	0.47681 (14)	0.0507 (3)
H35	0.6596	1.1153	0.5157	0.061*
C36	0.70186 (17)	0.92713 (15)	0.52510 (13)	0.0481 (3)
H36	0.6434	0.9027	0.5958	0.058*
O3	0.79160 (14)	1.21895 (11)	0.32819 (11)	0.0639 (3)
C37	0.8698 (3)	1.26075 (19)	0.21679 (18)	0.0768 (5)
H37A	0.9816	1.2730	0.2343	0.115*
H37B	0.8542	1.3492	0.1958	0.115*
H37C	0.8267	1.1885	0.1445	0.115*
C1A	0.47167 (16)	0.48460 (15)	0.77072 (14)	0.0496 (3)
H1A	0.4399	0.5534	0.7292	0.059*
C2A	0.38042 (18)	0.42069 (15)	0.87178 (15)	0.0547 (4)
H2A	0.4199	0.3611	0.9206	0.066*
O2	0.25512 (13)	0.43970 (13)	0.89739 (13)	0.0758 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0500 (6)	0.0417 (6)	0.0481 (6)	0.0163 (5)	0.0060 (5)	0.0086 (5)
N2	0.0514 (7)	0.0421 (6)	0.0482 (6)	0.0168 (5)	0.0077 (5)	0.0083 (5)
C3	0.0397 (7)	0.0464 (7)	0.0407 (7)	0.0139 (6)	0.0013 (5)	0.0043 (5)
C4	0.0551 (8)	0.0560 (8)	0.0481 (8)	0.0247 (7)	0.0105 (6)	0.0081 (6)
C5	0.0555 (8)	0.0478 (8)	0.0539 (8)	0.0242 (7)	0.0057 (6)	0.0050 (6)
C11	0.0437 (7)	0.0409 (7)	0.0446 (7)	0.0078 (6)	−0.0012 (6)	0.0040 (5)
C12	0.0432 (7)	0.0429 (7)	0.0438 (7)	0.0113 (6)	0.0027 (5)	0.0063 (5)
C13	0.0435 (7)	0.0482 (8)	0.0562 (8)	0.0048 (6)	0.0026 (6)	0.0134 (6)
C14	0.0402 (7)	0.0648 (9)	0.0546 (8)	0.0156 (7)	0.0035 (6)	0.0161 (7)
C15	0.0532 (8)	0.0531 (8)	0.0421 (7)	0.0227 (7)	0.0104 (6)	0.0121 (6)
C16	0.0518 (8)	0.0414 (7)	0.0487 (8)	0.0102 (6)	0.0072 (6)	0.0073 (6)
C17	0.0405 (7)	0.0446 (7)	0.0486 (7)	0.0097 (6)	0.0006 (6)	0.0044 (6)
O1	0.0669 (7)	0.0648 (7)	0.0729 (7)	0.0323 (6)	0.0096 (5)	0.0252 (5)
C18	0.0972 (13)	0.0589 (10)	0.0768 (12)	0.0368 (9)	0.0141 (10)	0.0253 (8)
C31	0.0380 (7)	0.0453 (7)	0.0402 (7)	0.0125 (6)	0.0012 (5)	0.0039 (5)
C32	0.0419 (7)	0.0494 (8)	0.0482 (7)	0.0156 (6)	0.0083 (6)	0.0026 (6)
C33	0.0455 (7)	0.0510 (8)	0.0455 (7)	0.0075 (6)	0.0116 (6)	0.0073 (6)
C34	0.0462 (7)	0.0405 (7)	0.0473 (7)	0.0071 (6)	0.0030 (6)	0.0053 (6)
C35	0.0560 (8)	0.0470 (8)	0.0531 (8)	0.0196 (6)	0.0136 (6)	0.0055 (6)
C36	0.0525 (8)	0.0518 (8)	0.0437 (7)	0.0176 (6)	0.0144 (6)	0.0106 (6)
O3	0.0835 (8)	0.0468 (6)	0.0661 (7)	0.0200 (5)	0.0224 (6)	0.0182 (5)
C37	0.1060 (14)	0.0580 (10)	0.0669 (11)	0.0169 (9)	0.0234 (10)	0.0238 (8)
C1A	0.0458 (8)	0.0456 (8)	0.0565 (8)	0.0119 (6)	0.0019 (6)	0.0090 (6)
C2A	0.0505 (8)	0.0477 (8)	0.0621 (9)	0.0086 (6)	0.0062 (7)	0.0046 (7)
O2	0.0561 (7)	0.0799 (8)	0.0946 (9)	0.0200 (6)	0.0264 (6)	0.0125 (7)

Geometric parameters (Å, º) top

N1—C5	1.3646 (18)	C18—H18A	0.9600
N1—N2	1.3656 (15)	C18—H18B	0.9600
N1—C11	1.4082 (17)	C18—H18C	0.9600
N2—C3	1.3281 (17)	C31—C32	1.3869 (18)
C3—C4	1.4151 (19)	C31—C36	1.3951 (19)
C3—C31	1.4668 (18)	C32—C33	1.3830 (19)
C4—C5	1.348 (2)	C32—H32	0.9300
C4—H4	0.9300	C33—C34	1.3852 (19)
C5—H5	0.9300	C33—H33	0.9300
C11—C1A	1.3482 (19)	C34—O3	1.3633 (16)
C11—C12	1.4779 (18)	C34—C35	1.3865 (19)
C12—C17	1.3885 (18)	C35—C36	1.3701 (19)
C12—C13	1.3950 (19)	C35—H35	0.9300
C13—C14	1.3693 (19)	C36—H36	0.9300
C13—H13	0.9300	O3—C37	1.4116 (19)
C14—C15	1.385 (2)	C37—H37A	0.9600
C14—H14	0.9300	C37—H37B	0.9600
C15—O1	1.3631 (16)	C37—H37C	0.9600
C15—C16	1.383 (2)	C1A—C2A	1.438 (2)
C16—C17	1.3821 (18)	C1A—H1A	0.9300
C16—H16	0.9300	C2A—O2	1.2133 (18)
C17—H17	0.9300	C2A—H2A	0.9300
O1—C18	1.422 (2)

C5—N1—N2	111.08 (11)	O1—C18—H18B	109.5
C5—N1—C11	128.12 (11)	H18A—C18—H18B	109.5
N2—N1—C11	120.42 (11)	O1—C18—H18C	109.5
C3—N2—N1	105.15 (10)	H18A—C18—H18C	109.5
N2—C3—C4	110.69 (12)	H18B—C18—H18C	109.5
N2—C3—C31	120.28 (12)	C32—C31—C36	117.49 (12)
C4—C3—C31	129.03 (12)	C32—C31—C3	121.90 (12)
C5—C4—C3	105.76 (12)	C36—C31—C3	120.60 (12)
C5—C4—H4	127.1	C33—C32—C31	121.85 (13)
C3—C4—H4	127.1	C33—C32—H32	119.1
C4—C5—N1	107.31 (12)	C31—C32—H32	119.1
C4—C5—H5	126.3	C32—C33—C34	119.60 (12)
N1—C5—H5	126.3	C32—C33—H33	120.2
C1A—C11—N1	119.20 (12)	C34—C33—H33	120.2
C1A—C11—C12	125.76 (12)	O3—C34—C33	125.26 (12)
N1—C11—C12	115.04 (11)	O3—C34—C35	115.54 (12)
C17—C12—C13	117.75 (12)	C33—C34—C35	119.20 (13)
C17—C12—C11	121.30 (12)	C36—C35—C34	120.67 (13)
C13—C12—C11	120.94 (12)	C36—C35—H35	119.7
C14—C13—C12	121.12 (13)	C34—C35—H35	119.7
C14—C13—H13	119.4	C35—C36—C31	121.16 (13)
C12—C13—H13	119.4	C35—C36—H36	119.4
C13—C14—C15	120.43 (13)	C31—C36—H36	119.4
C13—C14—H14	119.8	C34—O3—C37	118.14 (12)
C15—C14—H14	119.8	O3—C37—H37A	109.5
O1—C15—C16	125.18 (13)	O3—C37—H37B	109.5
O1—C15—C14	115.27 (13)	H37A—C37—H37B	109.5
C16—C15—C14	119.55 (13)	O3—C37—H37C	109.5
C17—C16—C15	119.65 (13)	H37A—C37—H37C	109.5
C17—C16—H16	120.2	H37B—C37—H37C	109.5
C15—C16—H16	120.2	C11—C1A—C2A	123.61 (13)
C16—C17—C12	121.50 (12)	C11—C1A—H1A	118.2
C16—C17—H17	119.3	C2A—C1A—H1A	118.2
C12—C17—H17	119.3	O2—C2A—C1A	124.07 (15)
C15—O1—C18	118.42 (13)	O2—C2A—H2A	118.0
O1—C18—H18A	109.5	C1A—C2A—H2A	118.0

C5—N1—N2—C3	−0.92 (14)	C15—C16—C17—C12	−0.2 (2)
C11—N1—N2—C3	−174.43 (11)	C13—C12—C17—C16	0.3 (2)
N1—N2—C3—C4	0.69 (15)	C11—C12—C17—C16	−178.75 (12)
N1—N2—C3—C31	179.94 (11)	C16—C15—O1—C18	−3.6 (2)
N2—C3—C4—C5	−0.22 (16)	C14—C15—O1—C18	176.38 (14)
C31—C3—C4—C5	−179.40 (13)	N2—C3—C31—C32	−179.19 (12)
C3—C4—C5—N1	−0.35 (16)	C4—C3—C31—C32	−0.1 (2)
N2—N1—C5—C4	0.80 (16)	N2—C3—C31—C36	−0.28 (19)
C11—N1—C5—C4	173.69 (12)	C4—C3—C31—C36	178.82 (13)
C5—N1—C11—C1A	−152.78 (14)	C36—C31—C32—C33	−1.3 (2)
N2—N1—C11—C1A	19.52 (18)	C3—C31—C32—C33	177.64 (12)
C5—N1—C11—C12	27.04 (19)	C31—C32—C33—C34	0.3 (2)
N2—N1—C11—C12	−160.66 (11)	C32—C33—C34—O3	−178.35 (12)
C1A—C11—C12—C17	50.16 (19)	C32—C33—C34—C35	1.2 (2)
N1—C11—C12—C17	−129.64 (13)	O3—C34—C35—C36	177.84 (13)
C1A—C11—C12—C13	−128.87 (16)	C33—C34—C35—C36	−1.8 (2)
N1—C11—C12—C13	51.32 (17)	C34—C35—C36—C31	0.8 (2)
C17—C12—C13—C14	−0.3 (2)	C32—C31—C36—C35	0.7 (2)
C11—C12—C13—C14	178.74 (13)	C3—C31—C36—C35	−178.22 (12)
C12—C13—C14—C15	0.3 (2)	C33—C34—O3—C37	2.3 (2)
C13—C14—C15—O1	179.86 (13)	C35—C34—O3—C37	−177.29 (14)
C13—C14—C15—C16	−0.2 (2)	N1—C11—C1A—C2A	−174.57 (12)
O1—C15—C16—C17	−179.88 (12)	C12—C11—C1A—C2A	5.6 (2)
C14—C15—C16—C17	0.2 (2)	C11—C1A—C2A—O2	−172.01 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱ	0.93	2.73	3.366 (2)	126
C18—H18C···N2ⁱ	0.96	2.74	3.627 (2)	155
C14—H14···O2ⁱⁱ	0.93	2.49	3.301 (2)	145
C33—H33···O1ⁱⁱⁱ	0.93	2.82	3.642 (2)	148
C37—H37B···O2^iv	0.96	2.75	3.688 (2)	166
C37—H37C···O1^v	0.96	2.76	3.650 (2)	155

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₂O₃
M_r	334.36
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.8081 (6), 9.8474 (5), 10.3292 (8)
α, β, γ (°)	94.997 (12), 93.811 (14), 106.719 (13)
V (Å³)	850.85 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.22 × 0.19 × 0.15

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8253, 2993, 2677
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.107, 1.04
No. of reflections	2993
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.25

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱ	0.93	2.73	3.366 (2)	126
C18—H18C···N2ⁱ	0.96	2.74	3.627 (2)	155
C14—H14···O2ⁱⁱ	0.93	2.49	3.301 (2)	145
C33—H33···O1ⁱⁱⁱ	0.93	2.82	3.642 (2)	148
C37—H37B···O2^iv	0.96	2.75	3.688 (2)	166
C37—H37C···O1^v	0.96	2.76	3.650 (2)	155

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

Acknowledgements

VS and SAB sincerely thank the Vice Chancellor and Management of Kalasalingam University, Anand Nagar, Krishnan Koil, for their support and encouragement.

References

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Volume 69| Part 4| April 2013| Pages o594-o595

doi:10.1107/S1600536813007678

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

(E)-3-(4-Meth­­oxy­phen­yl)-3-[3-(4-meth­­oxy­phen­yl)-1H-pyrazol-1-yl]prop-2-enal

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-3-(4-Methoxyphenyl)-3-[3-(4-methoxyphenyl)-1H-pyrazol-1-yl]prop-2-enal