1-[(E)-2-Formyl-1-(4-methyl-phen-yl)ethen-yl]-3-(4-methyl-phen-yl)pyrazole-4-carbaldehyde.

In the crystal structure of the title compound, C(21)H(18)N(2)O(2), mol-ecules are linked through C-H⋯O inter-actions. Two symmetry-related mol-ecules form a cyclic centrosymmetric R(2) (2)(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 = 330.37

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.174

S = 1.04

6019 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.30 e Å−3

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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027694/bt2774sup1.cif

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

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

C21H18N2O2	F(000) = 696
Mr = 330.37	Dx = 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

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

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(Fo2) + (0.0833P)2 + 0.2417P] where P = (Fo2 + 2Fc2)/3
6019 reflections	(Δ/σ)max = 0.037
228 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.30 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
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*

	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)

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)

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.

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) ; (ii) .