(Z)-3-Methyl-4-[1-(4-methyl-anilino)propyl-idene]-1-phenyl-1H-pyrazol-5(4H)-one.

In the title mol-ecule, C20H21N3O, the central pyrazole ring forms dihedral angles of 4.75 (9) and 49.11 (9)°, respectively, with the phenyl and methyl-substituted benzene rings. The dihedral angle between the phenyl and benzene rings is 51.76 (8)°. The amino group and carbonyl O atom are involved in an intra-molecular N-H⋯O hydrogen bond. In the crystal, π-π inter-actions are observed between benzene rings [centroid-centroid seperation = 3.892 (2) Å] and pyrazole rings [centroid-centroid seperation = 3.626 (2) Å], forming chains along [111]. The H atoms of the methyl group on the p-tolyl substituent were refined as disordered over two sets of sites in a 0.60 (4):0.40 (4) ratio.

Related literature

For applications of pyrazole derivatives, see: Wang et al. (2005 ▶); Vyas et al. (2011 ▶). For general background to Schiff-based pyrazole derivatives, see: Kahwa et al. (1986 ▶). For related structures, see: Sharma et al. (2012 ▶); Abdel-Aziz et al. (2012 ▶).

Experimental

Crystal data

C20H21N3O

M = 319.40

Triclinic,

a = 8.8092 (3) Å

b = 9.8629 (4) Å

c = 10.9278 (4) Å

α = 105.633 (4)°

β = 99.971 (3)°

γ = 104.961 (3)°

V = 852.75 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.792, T max = 1.000

23723 measured reflections

3341 independent reflections

2067 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.130

S = 1.01

3341 reflections

225 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813019144/lh5629sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019144/lh5629Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019144/lh5629Isup3.cml

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

C20H21N3O	Z = 2
Mr = 319.40	F(000) = 340
Triclinic, P1	Dx = 1.244 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8092 (3) Å	Cell parameters from 10378 reflections
b = 9.8629 (4) Å	θ = 3.5–29.1°
c = 10.9278 (4) Å	µ = 0.08 mm−1
α = 105.633 (4)°	T = 293 K
β = 99.971 (3)°	Block, yellow
γ = 104.961 (3)°	0.30 × 0.20 × 0.20 mm
V = 852.75 (5) Å3

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3341 independent reflections
Radiation source: fine-focus sealed tube	2067 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.5°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −12→12
Tmin = 0.792, Tmax = 1.000	l = −13→13
23723 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.3811P] where P = (Fo2 + 2Fc2)/3
3341 reflections	(Δ/σ)max = 0.001
225 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	Occ. (<1)
N1	0.6306 (2)	0.5996 (2)	0.37478 (17)	0.0405 (4)
N2	0.4810 (2)	0.6219 (2)	0.33572 (19)	0.0461 (5)
C3	0.4497 (3)	0.6918 (2)	0.4430 (2)	0.0432 (5)
C4	0.5759 (3)	0.7196 (2)	0.5581 (2)	0.0419 (5)
C5	0.6914 (2)	0.6541 (2)	0.5090 (2)	0.0396 (5)
O5	0.82042 (18)	0.64696 (18)	0.57192 (14)	0.0524 (4)
C6	0.6921 (2)	0.5216 (2)	0.2780 (2)	0.0382 (5)
C7	0.6007 (3)	0.4624 (2)	0.1476 (2)	0.0458 (6)
H7	0.4989	0.4733	0.1250	0.055*
C8	0.6609 (3)	0.3874 (3)	0.0520 (2)	0.0542 (7)
H8	0.5989	0.3479	−0.0351	0.065*
C9	0.8116 (3)	0.3703 (3)	0.0832 (2)	0.0537 (6)
H9	0.8524	0.3210	0.0180	0.064*
C10	0.9002 (3)	0.4274 (3)	0.2122 (2)	0.0540 (6)
H10	1.0013	0.4149	0.2343	0.065*
C11	0.8431 (3)	0.5029 (2)	0.3102 (2)	0.0460 (6)
H11	0.9053	0.5410	0.3971	0.055*
C12	0.7747 (3)	0.8304 (2)	0.9149 (2)	0.0423 (5)
C13	0.8209 (3)	0.7326 (3)	0.9708 (2)	0.0456 (6)
H13	0.8139	0.6388	0.9176	0.055*
C14	0.8777 (3)	0.7740 (3)	1.1057 (2)	0.0510 (6)
H14	0.9085	0.7072	1.1424	0.061*
C15	0.8898 (3)	0.9121 (3)	1.1875 (2)	0.0517 (6)
C16	0.8441 (3)	1.0085 (3)	1.1292 (2)	0.0558 (7)
H16	0.8516	1.1025	1.1823	0.067*
C17	0.7877 (3)	0.9697 (3)	0.9947 (2)	0.0517 (6)
H17	0.7585	1.0370	0.9580	0.062*
C18	0.9500 (4)	0.9557 (3)	1.3343 (3)	0.0825 (9)
H18A	0.9662	1.0595	1.3739	0.124*	0.60 (4)
H18B	1.0513	0.9368	1.3558	0.124*	0.60 (4)
H18C	0.8712	0.8985	1.3671	0.124*	0.60 (4)
H18D	0.9596	0.8703	1.3573	0.124*	0.40 (4)
H18E	0.8745	0.9931	1.3754	0.124*	0.40 (4)
H18F	1.0546	1.0314	1.3641	0.124*	0.40 (4)
N19	0.7247 (2)	0.7827 (2)	0.77489 (19)	0.0468 (5)
C20	0.5957 (3)	0.7862 (2)	0.6926 (2)	0.0419 (5)
C21	0.4839 (3)	0.8636 (3)	0.7452 (2)	0.0489 (6)
H21A	0.4943	0.8702	0.8366	0.059*
H21B	0.3724	0.8056	0.6963	0.059*
C22	0.5207 (3)	1.0205 (3)	0.7353 (3)	0.0670 (8)
H22A	0.4515	1.0688	0.7755	0.101*
H22B	0.5010	1.0139	0.6444	0.101*
H22C	0.6325	1.0768	0.7798	0.101*
C23	0.2922 (3)	0.7244 (3)	0.4309 (3)	0.0591 (7)
H23A	0.2374	0.6964	0.3396	0.089*
H23B	0.3132	0.8288	0.4728	0.089*
H23C	0.2248	0.6690	0.4728	0.089*
H19	0.778 (3)	0.728 (3)	0.727 (2)	0.063 (8)*

	U11	U22	U33	U12	U13	U23
N1	0.0335 (10)	0.0496 (11)	0.0386 (11)	0.0157 (8)	0.0051 (8)	0.0155 (9)
N2	0.0348 (10)	0.0554 (12)	0.0490 (12)	0.0162 (9)	0.0063 (9)	0.0198 (10)
C3	0.0379 (12)	0.0441 (13)	0.0485 (14)	0.0111 (10)	0.0103 (11)	0.0193 (11)
C4	0.0404 (12)	0.0436 (13)	0.0448 (14)	0.0127 (10)	0.0131 (10)	0.0190 (10)
C5	0.0363 (12)	0.0430 (13)	0.0412 (13)	0.0120 (10)	0.0091 (10)	0.0180 (10)
O5	0.0453 (10)	0.0708 (11)	0.0432 (9)	0.0296 (8)	0.0055 (7)	0.0156 (8)
C6	0.0367 (11)	0.0329 (11)	0.0433 (13)	0.0085 (9)	0.0075 (10)	0.0142 (10)
C7	0.0403 (13)	0.0467 (13)	0.0463 (14)	0.0138 (10)	0.0027 (11)	0.0146 (11)
C8	0.0627 (16)	0.0476 (14)	0.0434 (14)	0.0187 (12)	0.0019 (12)	0.0076 (11)
C9	0.0622 (16)	0.0475 (14)	0.0500 (16)	0.0258 (12)	0.0136 (13)	0.0070 (12)
C10	0.0505 (14)	0.0585 (15)	0.0548 (16)	0.0282 (12)	0.0103 (12)	0.0134 (12)
C11	0.0427 (13)	0.0518 (14)	0.0425 (14)	0.0176 (11)	0.0064 (11)	0.0149 (11)
C12	0.0387 (12)	0.0490 (14)	0.0401 (13)	0.0144 (10)	0.0150 (10)	0.0130 (11)
C13	0.0434 (13)	0.0465 (13)	0.0471 (14)	0.0162 (11)	0.0142 (11)	0.0123 (11)
C14	0.0532 (15)	0.0548 (15)	0.0489 (15)	0.0166 (12)	0.0130 (12)	0.0241 (12)
C15	0.0512 (14)	0.0589 (16)	0.0414 (14)	0.0097 (12)	0.0159 (11)	0.0163 (12)
C16	0.0648 (16)	0.0505 (15)	0.0477 (15)	0.0176 (13)	0.0186 (13)	0.0075 (12)
C17	0.0596 (15)	0.0498 (14)	0.0535 (16)	0.0228 (12)	0.0185 (12)	0.0218 (12)
C18	0.104 (3)	0.086 (2)	0.0468 (17)	0.0230 (19)	0.0128 (16)	0.0160 (15)
N19	0.0469 (12)	0.0575 (13)	0.0388 (12)	0.0236 (10)	0.0124 (9)	0.0130 (9)
C20	0.0371 (12)	0.0396 (12)	0.0506 (14)	0.0083 (10)	0.0123 (10)	0.0209 (11)
C21	0.0458 (14)	0.0519 (14)	0.0556 (15)	0.0194 (11)	0.0208 (11)	0.0201 (12)
C22	0.0748 (19)	0.0550 (16)	0.081 (2)	0.0296 (14)	0.0248 (16)	0.0261 (14)
C23	0.0425 (14)	0.0720 (17)	0.0658 (17)	0.0246 (13)	0.0106 (12)	0.0236 (14)

N1—C5	1.372 (3)	C14—C15	1.379 (3)
N1—N2	1.404 (2)	C14—H14	0.9300
N1—C6	1.407 (3)	C15—C16	1.381 (3)
N2—C3	1.304 (3)	C15—C18	1.502 (3)
C3—C4	1.437 (3)	C16—C17	1.379 (3)
C3—C23	1.496 (3)	C16—H16	0.9300
C4—C20	1.398 (3)	C17—H17	0.9300
C4—C5	1.442 (3)	C18—H18A	0.9600
C5—O5	1.252 (2)	C18—H18B	0.9600
C6—C11	1.388 (3)	C18—H18C	0.9600
C6—C7	1.389 (3)	C18—H18D	0.9600
C7—C8	1.378 (3)	C18—H18E	0.9600
C7—H7	0.9300	C18—H18F	0.9600
C8—C9	1.377 (3)	N19—C20	1.335 (3)
C8—H8	0.9300	N19—H19	0.92 (3)
C9—C10	1.371 (3)	C20—C21	1.494 (3)
C9—H9	0.9300	C21—C22	1.534 (3)
C10—C11	1.380 (3)	C21—H21A	0.9700
C10—H10	0.9300	C21—H21B	0.9700
C11—H11	0.9300	C22—H22A	0.9600
C12—C17	1.377 (3)	C22—H22B	0.9600
C12—C13	1.380 (3)	C22—H22C	0.9600
C12—N19	1.425 (3)	C23—H23A	0.9600
C13—C14	1.380 (3)	C23—H23B	0.9600
C13—H13	0.9300	C23—H23C	0.9600
C5—N1—N2	111.70 (17)	C12—C17—H17	120.2
C5—N1—C6	129.42 (17)	C16—C17—H17	120.2
N2—N1—C6	118.78 (17)	C15—C18—H18A	109.5
C3—N2—N1	106.56 (17)	C15—C18—H18B	109.5
N2—C3—C4	111.68 (19)	H18A—C18—H18B	109.5
N2—C3—C23	118.1 (2)	C15—C18—H18C	109.5
C4—C3—C23	130.2 (2)	H18A—C18—H18C	109.5
C20—C4—C3	133.0 (2)	H18B—C18—H18C	109.5
C20—C4—C5	122.02 (19)	C15—C18—H18D	109.5
C3—C4—C5	104.92 (19)	H18A—C18—H18D	141.1
O5—C5—N1	125.9 (2)	H18B—C18—H18D	56.3
O5—C5—C4	129.0 (2)	H18C—C18—H18D	56.3
N1—C5—C4	105.10 (17)	C15—C18—H18E	109.5
C11—C6—C7	119.2 (2)	H18A—C18—H18E	56.3
C11—C6—N1	121.19 (19)	H18B—C18—H18E	141.1
C7—C6—N1	119.60 (19)	H18C—C18—H18E	56.3
C8—C7—C6	120.0 (2)	H18D—C18—H18E	109.5
C8—C7—H7	120.0	C15—C18—H18F	109.5
C6—C7—H7	120.0	H18A—C18—H18F	56.3
C9—C8—C7	121.0 (2)	H18B—C18—H18F	56.3
C9—C8—H8	119.5	H18C—C18—H18F	141.1
C7—C8—H8	119.5	H18D—C18—H18F	109.5
C10—C9—C8	118.7 (2)	H18E—C18—H18F	109.5
C10—C9—H9	120.7	C20—N19—C12	131.3 (2)
C8—C9—H9	120.7	C20—N19—H19	108.9 (15)
C9—C10—C11	121.6 (2)	C12—N19—H19	119.2 (15)
C9—C10—H10	119.2	N19—C20—C4	116.9 (2)
C11—C10—H10	119.2	N19—C20—C21	120.1 (2)
C10—C11—C6	119.5 (2)	C4—C20—C21	122.9 (2)
C10—C11—H11	120.3	C20—C21—C22	112.1 (2)
C6—C11—H11	120.3	C20—C21—H21A	109.2
C17—C12—C13	119.5 (2)	C22—C21—H21A	109.2
C17—C12—N19	123.6 (2)	C20—C21—H21B	109.2
C13—C12—N19	116.8 (2)	C22—C21—H21B	109.2
C14—C13—C12	119.9 (2)	H21A—C21—H21B	107.9
C14—C13—H13	120.0	C21—C22—H22A	109.5
C12—C13—H13	120.0	C21—C22—H22B	109.5
C15—C14—C13	121.6 (2)	H22A—C22—H22B	109.5
C15—C14—H14	119.2	C21—C22—H22C	109.5
C13—C14—H14	119.2	H22A—C22—H22C	109.5
C14—C15—C16	117.5 (2)	H22B—C22—H22C	109.5
C14—C15—C18	121.2 (2)	C3—C23—H23A	109.5
C16—C15—C18	121.4 (2)	C3—C23—H23B	109.5
C17—C16—C15	122.0 (2)	H23A—C23—H23B	109.5
C17—C16—H16	119.0	C3—C23—H23C	109.5
C15—C16—H16	119.0	H23A—C23—H23C	109.5
C12—C17—C16	119.6 (2)	H23B—C23—H23C	109.5
C5—N1—N2—C3	1.3 (2)	C8—C9—C10—C11	−1.0 (4)
C6—N1—N2—C3	178.00 (18)	C9—C10—C11—C6	0.2 (4)
N1—N2—C3—C4	0.1 (2)	C7—C6—C11—C10	0.6 (3)
N1—N2—C3—C23	−177.35 (19)	N1—C6—C11—C10	−179.1 (2)
N2—C3—C4—C20	−178.3 (2)	C17—C12—C13—C14	0.8 (3)
C23—C3—C4—C20	−1.3 (4)	N19—C12—C13—C14	177.1 (2)
N2—C3—C4—C5	−1.3 (2)	C12—C13—C14—C15	0.0 (4)
C23—C3—C4—C5	175.7 (2)	C13—C14—C15—C16	−0.5 (4)
N2—N1—C5—O5	178.3 (2)	C13—C14—C15—C18	179.4 (2)
C6—N1—C5—O5	2.0 (4)	C14—C15—C16—C17	0.3 (4)
N2—N1—C5—C4	−2.0 (2)	C18—C15—C16—C17	−179.6 (2)
C6—N1—C5—C4	−178.31 (19)	C13—C12—C17—C16	−1.1 (3)
C20—C4—C5—O5	−1.0 (3)	N19—C12—C17—C16	−177.1 (2)
C3—C4—C5—O5	−178.4 (2)	C15—C16—C17—C12	0.5 (4)
C20—C4—C5—N1	179.35 (19)	C17—C12—N19—C20	−51.1 (4)
C3—C4—C5—N1	1.9 (2)	C13—C12—N19—C20	132.8 (3)
C5—N1—C6—C11	−7.2 (3)	C12—N19—C20—C4	−175.5 (2)
N2—N1—C6—C11	176.70 (19)	C12—N19—C20—C21	6.7 (4)
C5—N1—C6—C7	173.0 (2)	C3—C4—C20—N19	174.6 (2)
N2—N1—C6—C7	−3.1 (3)	C5—C4—C20—N19	−2.0 (3)
C11—C6—C7—C8	−0.6 (3)	C3—C4—C20—C21	−7.6 (4)
N1—C6—C7—C8	179.2 (2)	C5—C4—C20—C21	175.8 (2)
C6—C7—C8—C9	−0.2 (4)	N19—C20—C21—C22	98.8 (3)
C7—C8—C9—C10	1.0 (4)	C4—C20—C21—C22	−78.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N19—H19···O5	0.92 (3)	1.82 (2)	2.656 (2)	151 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N19—H19⋯O5	0.92 (3)	1.82 (2)	2.656 (2)	151 (2)