(E)-1,5-Dimethyl-4-(4-methyl­benzyl­ideneamino)-2-phenyl-1H-pyrazol-3(2H)-one

In the crystal structure of the title compound, C₁₉H₁₉N₃O, mol­ecules are linked via C—H...O inter­actions, forming ribbons along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.051
• wR factor = 0.084
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(E)-4-(4-methylbenzylideneamino)-1, 5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Crystal data

C19H19N3O	F(000) = 1296
Mr = 305.37	Dx = 1.217 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3564 reflections
a = 6.9966 (8) Å	θ = 2.4–21.9°
b = 17.994 (2) Å	µ = 0.08 mm^−1
c = 26.469 (3) Å	T = 291 K
V = 3332.3 (7) Å^3	Block, yellow
Z = 8	0.32 × 0.26 × 0.24 mm

Data collection

Bruker SMART Apex CCD diffractometer	3255 independent reflections
Radiation source: sealed tube	1799 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.97, Tmax = 0.98	k = −22→22
20184 measured reflections	l = −32→32

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.02P)^2] where P = (Fo^2 + 2Fc^2)/3
3255 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.24 e Å^−3
150 restraints	Δρmin = −0.13 e Å^−3

Special details

Experimental. ¹H NMR(300 MHz, CDCl3): d 9.72 (s, 1H), 7.19- 7.78 (m, 9H), 3.13 (s, 3H), 2.48(s, 3H), 2.38(s, 3H). IR (KBr, cm-1): \v 3060, 3022, 2934, 1653, 1578, 1493, 1303.

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

5.4839 (0.0045) x - 0.7469 (0.0188) y + 16.4008 (0.0214) z = 12.9198 (0.0143)

* -0.0009 (0.0016) C1 * -0.0007 (0.0018) C2 * 0.0014 (0.0019) C3 * -0.0003 (0.0020) C4 * -0.0013 (0.0019) C5 * 0.0019 (0.0017) C6

Rms deviation of fitted atoms = 0.0012

3.1263 (0.0068) x - 14.2119 (0.0119) y + 11.1209 (0.0253) z = 5.6710 (0.0160)

Angle to previous plane (with approximate e.s.d.) = 49.96 (0.10)

* 0.0436 (0.0012) N1 * -0.0475 (0.0012) N2 * -0.0240 (0.0013) C7 * -0.0049 (0.0014) C8 * 0.0329 (0.0014) C9

Rms deviation of fitted atoms = 0.0342

2.7520 (0.0069) x - 15.5744 (0.0090) y + 8.2063 (0.0261) z = 3.7929 (0.0100)

Angle to previous plane (with approximate e.s.d.) = 8.25 (0.14)

* 0.0046 (0.0017) C11 * -0.0045 (0.0017) C12 * 0.0002 (0.0018) C13 * 0.0040 (0.0018) C14 * -0.0041 (0.0019) C15 * -0.0002 (0.0019) C16

Rms deviation of fitted atoms = 0.0035

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4453 (3)	0.24467 (14)	0.64994 (8)	0.0528 (5)
C2	0.4641 (4)	0.32168 (15)	0.64718 (9)	0.0631 (6)
H2	0.5407	0.3433	0.6225	0.076*
C3	0.3670 (4)	0.36576 (17)	0.68178 (10)	0.0775 (7)
H3	0.3786	0.4172	0.6804	0.093*
C4	0.2536 (4)	0.33327 (19)	0.71810 (11)	0.0808 (7)
H4	0.1887	0.3630	0.7412	0.097*
C5	0.2358 (4)	0.25784 (17)	0.72058 (10)	0.0741 (7)
H5	0.1586	0.2366	0.7452	0.089*
C6	0.3318 (4)	0.21280 (16)	0.68664 (9)	0.0656 (6)
H6	0.3198	0.1614	0.6885	0.079*
C7	0.4330 (3)	0.15234 (13)	0.58073 (8)	0.0501 (5)
C8	0.5553 (3)	0.14420 (13)	0.53766 (8)	0.0469 (5)
C9	0.7177 (3)	0.18406 (12)	0.54635 (8)	0.0476 (5)
C10	0.3636 (4)	0.07488 (12)	0.48357 (9)	0.0544 (5)
H10	0.2757	0.0704	0.5098	0.065*
C11	0.3197 (3)	0.04164 (12)	0.43456 (9)	0.0531 (5)
C12	0.1463 (4)	0.00740 (13)	0.42664 (9)	0.0593 (6)
H12	0.0571	0.0060	0.4527	0.071*
C13	0.1024 (4)	−0.02473 (13)	0.38096 (9)	0.0634 (6)
H13	−0.0159	−0.0476	0.3772	0.076*
C14	0.2272 (4)	−0.02441 (14)	0.34018 (10)	0.0670 (6)
C15	0.4003 (4)	0.01168 (15)	0.34963 (10)	0.0726 (6)
H15	0.4890	0.0141	0.3235	0.087*
C16	0.4479 (4)	0.04373 (14)	0.39496 (9)	0.0672 (6)
H16	0.5659	0.0667	0.3990	0.081*
C17	0.8697 (3)	0.23933 (14)	0.62273 (9)	0.0672 (7)
H17A	0.9271	0.1941	0.6345	0.101*
H17B	0.8282	0.2683	0.6511	0.101*
H17C	0.9616	0.2671	0.6035	0.101*
C18	0.8914 (4)	0.18859 (14)	0.51411 (9)	0.0678 (7)
H18A	0.9963	0.1649	0.5310	0.102*
H18B	0.9222	0.2398	0.5080	0.102*
H18C	0.8677	0.1640	0.4825	0.102*
C19	0.1821 (5)	−0.05746 (18)	0.29144 (10)	0.0957 (9)
H19A	0.0546	−0.0772	0.2922	0.144*
H19B	0.2709	−0.0968	0.2844	0.144*
H19C	0.1910	−0.0202	0.2656	0.144*
N1	0.5377 (3)	0.19725 (10)	0.61479 (7)	0.0514 (4)
N2	0.7054 (2)	0.22177 (10)	0.59076 (7)	0.0510 (4)
N3	0.5197 (3)	0.11003 (10)	0.49139 (7)	0.0535 (5)
O1	0.2687 (2)	0.13124 (9)	0.58937 (6)	0.0662 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0396 (10)	0.0672 (11)	0.0515 (11)	−0.0016 (10)	−0.0019 (9)	0.0009 (9)
C2	0.0516 (12)	0.0727 (13)	0.0650 (12)	0.0010 (11)	0.0016 (11)	0.0005 (11)
C3	0.0643 (14)	0.0852 (15)	0.0830 (14)	0.0062 (13)	0.0052 (12)	−0.0082 (13)
C4	0.0651 (14)	0.1012 (16)	0.0761 (14)	0.0094 (13)	0.0055 (12)	−0.0091 (13)
C5	0.0588 (13)	0.0997 (16)	0.0638 (13)	−0.0051 (12)	0.0075 (11)	0.0045 (12)
C6	0.0518 (13)	0.0858 (14)	0.0591 (12)	−0.0046 (11)	0.0005 (10)	0.0069 (12)
C7	0.0374 (11)	0.0542 (11)	0.0588 (11)	−0.0023 (9)	−0.0001 (9)	0.0057 (9)
C8	0.0380 (10)	0.0479 (10)	0.0549 (10)	0.0006 (8)	−0.0022 (9)	0.0056 (9)
C9	0.0362 (10)	0.0517 (11)	0.0548 (11)	0.0011 (9)	0.0026 (9)	0.0040 (9)
C10	0.0527 (12)	0.0517 (12)	0.0587 (12)	0.0019 (10)	0.0022 (10)	0.0030 (10)
C11	0.0503 (11)	0.0528 (11)	0.0562 (11)	−0.0028 (9)	−0.0001 (9)	0.0007 (9)
C12	0.0577 (13)	0.0614 (13)	0.0587 (12)	−0.0061 (11)	0.0024 (11)	0.0065 (10)
C13	0.0626 (13)	0.0653 (13)	0.0623 (13)	−0.0105 (11)	−0.0064 (11)	0.0015 (10)
C14	0.0719 (14)	0.0707 (14)	0.0584 (12)	−0.0106 (11)	−0.0059 (12)	−0.0046 (11)
C15	0.0703 (14)	0.0849 (15)	0.0626 (13)	−0.0112 (12)	0.0042 (12)	−0.0087 (11)
C16	0.0564 (13)	0.0771 (13)	0.0682 (13)	−0.0125 (11)	0.0035 (11)	−0.0064 (11)
C17	0.0431 (14)	0.0772 (18)	0.0812 (17)	−0.0104 (13)	−0.0115 (13)	−0.0036 (13)
C18	0.0557 (16)	0.0731 (18)	0.0746 (16)	−0.0078 (13)	0.0169 (13)	0.0011 (13)
C19	0.106 (2)	0.108 (2)	0.0730 (19)	−0.0228 (19)	−0.0098 (17)	−0.0172 (16)
N1	0.0375 (9)	0.0614 (10)	0.0553 (9)	−0.0061 (8)	0.0025 (8)	0.0005 (8)
N2	0.0329 (9)	0.0596 (10)	0.0603 (10)	−0.0060 (8)	−0.0008 (8)	0.0017 (8)
N3	0.0482 (10)	0.0521 (10)	0.0601 (10)	0.0008 (8)	−0.0009 (9)	0.0032 (8)
O1	0.0414 (10)	0.0808 (12)	0.0766 (11)	−0.0158 (8)	0.0073 (8)	−0.0071 (9)

Geometric parameters (Å, º)

C1—C6	1.380 (3)	C11—C12	1.377 (3)
C1—C2	1.394 (3)	C11—C16	1.380 (3)
C1—N1	1.418 (3)	C12—C13	1.375 (3)
C2—C3	1.389 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.388 (3)
C3—C4	1.377 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.397 (3)
C4—C5	1.364 (4)	C14—C19	1.455 (3)
C4—H4	0.9300	C15—C16	1.372 (3)
C5—C6	1.384 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—N2	1.462 (3)
C7—O1	1.232 (2)	C17—H17A	0.9600
C7—N1	1.415 (3)	C17—H17B	0.9600
C7—C8	1.433 (3)	C17—H17C	0.9600
C8—C9	1.363 (3)	C18—H18A	0.9600
C8—N3	1.393 (3)	C18—H18B	0.9600
C9—N2	1.360 (3)	C18—H18C	0.9600
C9—C18	1.487 (3)	C19—H19A	0.9600
C10—N3	1.279 (3)	C19—H19B	0.9600
C10—C11	1.461 (3)	C19—H19C	0.9600
C10—H10	0.9300	N1—N2	1.406 (2)
C6—C1—C2	120.3 (2)	C12—C13—H13	118.6
C6—C1—N1	118.3 (2)	C14—C13—H13	118.6
C2—C1—N1	121.4 (2)	C13—C14—C15	114.1 (2)
C3—C2—C1	119.1 (3)	C13—C14—C19	123.4 (3)
C3—C2—H2	120.4	C15—C14—C19	122.5 (3)
C1—C2—H2	120.4	C16—C15—C14	124.2 (3)
C4—C3—C2	120.0 (3)	C16—C15—H15	117.9
C4—C3—H3	120.0	C14—C15—H15	117.9
C2—C3—H3	120.0	C15—C16—C11	119.7 (2)
C5—C4—C3	120.6 (3)	C15—C16—H16	120.2
C5—C4—H4	119.7	C11—C16—H16	120.2
C3—C4—H4	119.7	N2—C17—H17A	109.5
C4—C5—C6	120.5 (3)	N2—C17—H17B	109.5
C4—C5—H5	119.8	H17A—C17—H17B	109.5
C6—C5—H5	119.8	N2—C17—H17C	109.5
C1—C6—C5	119.5 (3)	H17A—C17—H17C	109.5
C1—C6—H6	120.2	H17B—C17—H17C	109.5
C5—C6—H6	120.2	C9—C18—H18A	109.5
O1—C7—N1	122.7 (2)	C9—C18—H18B	109.5
O1—C7—C8	132.3 (2)	H18A—C18—H18B	109.5
N1—C7—C8	104.83 (18)	C9—C18—H18C	109.5
C9—C8—N3	122.0 (2)	H18A—C18—H18C	109.5
C9—C8—C7	108.1 (2)	H18B—C18—H18C	109.5
N3—C8—C7	129.6 (2)	C14—C19—H19A	109.5
N2—C9—C8	110.8 (2)	C14—C19—H19B	109.5
N2—C9—C18	121.4 (2)	H19A—C19—H19B	109.5
C8—C9—C18	127.8 (2)	C14—C19—H19C	109.5
N3—C10—C11	121.7 (2)	H19A—C19—H19C	109.5
N3—C10—H10	119.2	H19B—C19—H19C	109.5
C11—C10—H10	119.2	N2—N1—C7	108.86 (17)
C12—C11—C16	118.0 (2)	N2—N1—C1	119.23 (18)
C12—C11—C10	120.2 (2)	C7—N1—C1	121.71 (18)
C16—C11—C10	121.8 (2)	C9—N2—N1	106.69 (17)
C13—C12—C11	121.2 (2)	C9—N2—C17	123.96 (19)
C13—C12—H12	119.4	N1—N2—C17	117.54 (18)
C11—C12—H12	119.4	C10—N3—C8	120.9 (2)
C12—C13—C14	122.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1^i	0.93	2.48	3.321 (3)	150
C18—H18A···O1^ii	0.96	2.53	3.465 (4)	166

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