(E)-3-(4-Meth-oxy-phen-yl)-3-[3-(4-meth-oxy-phen-yl)-1H-pyrazol-1-yl]prop-2-enal.

In the title mol-ecule, C20H18N2O3, the pyrazole ring forms a dihedral angle of 2.2 (1)° with its meth-oxy-phenyl substituent and a dihedral angle of 67.2 (1)° with the benzene substituent on the propenal unit. In the crystal, mol-ecules are connected by weak C-H⋯O hydrogen bonds, forming R 2 (2)(26) and R 2 (2)(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 C 2 (2)(15) chains and R 2 (2)(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 = 334.36

Triclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.107

S = 1.04

2993 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.25 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007678/sj5307sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007678/sj5307Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H18N2O3	Z = 2
Mr = 334.36	F(000) = 352
Triclinic, P1	Dx = 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

Bruker SMART APEX CCD diffractometer	2677 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ω scans	h = −10→10
8253 measured reflections	k = −11→11
2993 independent reflections	l = −12→12

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(Fo2) + (0.057P)2 + 0.1393P] where P = (Fo2 + 2Fc2)/3
2993 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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···O2iv	0.96	2.75	3.688 (2)	166
C37—H37C···O1v	0.96	2.76	3.650 (2)	155

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⋯O2iv	0.96	2.75	3.688 (2)	166
C37—H37C⋯O1v	0.96	2.76	3.650 (2)	155

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .