(E)-1,5-Dimethyl-4-[3-(2-phenoxy­ethoxy)benzyl­ideneamino]-2-phenyl-1H-pyrazol-3(2H)-one

Diao, C.-H.; Yu, M.

doi:10.1107/S1600536806038402

(E)-1,5-Dimethyl-4-[3-(2-phenoxyethoxy)benzylideneamino]-2-phenyl-1H-pyrazol-3(2H)-one

In the title compound, C₂₆H₂₅N₃O₃, the central benzene ring makes dihedral angles of 13.93 (7), 54.45 (6) and 80.83 (5)°, respectively, with the pyrazolone ring, the attached phenyl ring and the other terminal phenyl ring. The crystal structure is stabilized by a couple of weak non-classical intermolecular C—H

O interactions, forming an infinite network.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038402/at2118sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038402/at2118Isup2.hkl Contains datablock I

CCDC reference: 623978

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C)= 0.003 Å
R factor = 0.048
wR factor = 0.138
Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(E)-1,5-Dimethyl-4-[3-(2-phenoxyethoxy)benzylideneamino]-2-phenyl- 1H-pyrazol-3(2H)-one top

Crystal data top

C₂₆H₂₅N₃O₃	F(000) = 904
M_r = 427.49	D_x = 1.255 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2796 reflections
a = 11.3949 (18) Å	θ = 2.2–23.2°
b = 7.4456 (12) Å	µ = 0.08 mm⁻¹
c = 26.791 (4) Å	T = 294 K
β = 95.392 (3)°	Block, yellow
V = 2262.9 (6) Å³	0.30 × 0.24 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4635 independent reflections
Radiation source: fine-focus sealed tube	2621 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
φ and ω scans	θ_max = 26.4°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.958, T_max = 0.984	k = −9→9
12330 measured reflections	l = −33→20

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0654P)² + 0.2074P] where P = (F_o² + 2F_c²)/3
4635 reflections	(Δ/σ)_max = 0.002
291 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

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 > 2σ(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
O1	−0.00745 (13)	0.4705 (2)	0.63078 (6)	0.0713 (5)
O2	0.07467 (14)	0.7235 (2)	0.56092 (6)	0.0687 (5)
O3	0.52490 (13)	1.04054 (18)	0.37744 (5)	0.0567 (4)
N1	0.40235 (14)	0.7835 (2)	0.45023 (5)	0.0397 (4)
N2	0.60559 (14)	0.77117 (19)	0.35410 (6)	0.0429 (4)
N3	0.58681 (15)	0.5891 (2)	0.36475 (6)	0.0454 (4)
C1	−0.1617 (2)	0.2459 (3)	0.63317 (8)	0.0596 (6)
H1	−0.2074	0.2975	0.6064	0.071*
C2	−0.2006 (2)	0.0953 (4)	0.65624 (9)	0.0684 (7)
H2	−0.2730	0.0457	0.6447	0.082*
C3	−0.1351 (2)	0.0167 (4)	0.69585 (10)	0.0748 (7)
H3	−0.1629	−0.0842	0.7115	0.090*
C4	−0.0267 (2)	0.0904 (4)	0.71204 (10)	0.0763 (8)
H4	0.0191	0.0378	0.7387	0.092*
C5	0.0137 (2)	0.2396 (3)	0.68941 (9)	0.0649 (7)
H5	0.0869	0.2874	0.7005	0.078*
C6	−0.05443 (19)	0.3196 (3)	0.64999 (8)	0.0541 (6)
C7	−0.0809 (2)	0.5775 (4)	0.59637 (9)	0.0737 (8)
H7A	−0.1568	0.5962	0.6092	0.088*
H7B	−0.0938	0.5162	0.5644	0.088*
C8	−0.0226 (2)	0.7529 (4)	0.58971 (9)	0.0705 (7)
H8A	−0.0779	0.8363	0.5725	0.085*
H8B	0.0046	0.8035	0.6221	0.085*
C9	0.13331 (19)	0.8722 (3)	0.54595 (7)	0.0517 (6)
C10	0.1091 (2)	1.0469 (3)	0.55935 (8)	0.0622 (6)
H10	0.0502	1.0705	0.5802	0.075*
C11	0.1735 (2)	1.1851 (3)	0.54146 (8)	0.0641 (7)
H11	0.1574	1.3027	0.5504	0.077*
C12	0.2613 (2)	1.1524 (3)	0.51055 (7)	0.0543 (6)
H12	0.3039	1.2475	0.4988	0.065*
C13	0.28609 (17)	0.9778 (3)	0.49693 (6)	0.0416 (5)
C14	0.22074 (17)	0.8387 (3)	0.51472 (7)	0.0465 (5)
H14	0.2359	0.7211	0.5055	0.056*
C15	0.37678 (17)	0.9434 (3)	0.46308 (7)	0.0421 (5)
H15	0.4169	1.0398	0.4506	0.051*
C16	0.48346 (16)	0.7526 (2)	0.41523 (6)	0.0372 (4)
C17	0.53624 (16)	0.8769 (3)	0.38295 (7)	0.0403 (5)
C18	0.51858 (17)	0.5834 (2)	0.40380 (7)	0.0407 (5)
C19	0.4906 (2)	0.4135 (3)	0.42857 (8)	0.0621 (7)
H19A	0.4720	0.3227	0.4036	0.093*
H19B	0.4242	0.4314	0.4476	0.093*
H19C	0.5574	0.3759	0.4506	0.093*
C20	0.6804 (2)	0.4616 (3)	0.35678 (9)	0.0660 (7)
H20A	0.7496	0.4908	0.3785	0.099*
H20B	0.6984	0.4678	0.3225	0.099*
H20C	0.6549	0.3423	0.3640	0.099*
C21	0.63202 (17)	0.8227 (3)	0.30503 (7)	0.0409 (5)
C22	0.70002 (18)	0.9739 (3)	0.30058 (8)	0.0506 (5)
H22	0.7312	1.0356	0.3290	0.061*
C23	0.72142 (19)	1.0329 (3)	0.25301 (9)	0.0619 (6)
H23	0.7661	1.1358	0.2494	0.074*
C24	0.6768 (2)	0.9395 (3)	0.21135 (9)	0.0642 (7)
H24	0.6915	0.9794	0.1796	0.077*
C25	0.6107 (2)	0.7882 (3)	0.21611 (8)	0.0613 (6)
H25	0.5817	0.7247	0.1877	0.074*
C26	0.58685 (19)	0.7290 (3)	0.26327 (8)	0.0509 (5)
H26	0.5409	0.6273	0.2666	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0482 (9)	0.0935 (13)	0.0719 (11)	−0.0031 (9)	0.0047 (8)	0.0185 (10)
O2	0.0656 (10)	0.0722 (11)	0.0734 (11)	0.0026 (9)	0.0346 (9)	0.0050 (9)
O3	0.0847 (11)	0.0303 (8)	0.0589 (9)	0.0029 (7)	0.0266 (8)	0.0023 (7)
N1	0.0460 (9)	0.0394 (10)	0.0343 (8)	−0.0011 (8)	0.0067 (7)	0.0001 (7)
N2	0.0565 (10)	0.0299 (9)	0.0443 (9)	0.0031 (8)	0.0151 (8)	0.0015 (7)
N3	0.0606 (11)	0.0299 (9)	0.0477 (9)	0.0067 (8)	0.0152 (8)	0.0018 (7)
C1	0.0482 (14)	0.0783 (17)	0.0519 (13)	0.0026 (12)	0.0034 (11)	−0.0055 (12)
C2	0.0545 (15)	0.0768 (18)	0.0721 (16)	−0.0043 (14)	−0.0031 (13)	−0.0057 (14)
C3	0.0652 (17)	0.0724 (18)	0.0856 (18)	−0.0053 (14)	0.0004 (15)	0.0082 (15)
C4	0.0642 (17)	0.086 (2)	0.0760 (17)	0.0048 (15)	−0.0067 (14)	0.0133 (15)
C5	0.0470 (13)	0.0806 (18)	0.0662 (15)	−0.0005 (13)	0.0002 (12)	−0.0034 (14)
C6	0.0445 (13)	0.0718 (16)	0.0476 (12)	0.0048 (12)	0.0122 (11)	−0.0051 (12)
C7	0.0496 (14)	0.104 (2)	0.0692 (16)	0.0040 (15)	0.0151 (13)	0.0183 (15)
C8	0.0559 (15)	0.0908 (19)	0.0685 (16)	0.0078 (14)	0.0248 (13)	0.0109 (14)
C9	0.0516 (13)	0.0604 (15)	0.0443 (12)	0.0044 (11)	0.0106 (10)	0.0000 (11)
C10	0.0637 (15)	0.0717 (17)	0.0534 (13)	0.0114 (13)	0.0177 (12)	−0.0114 (12)
C11	0.0749 (17)	0.0560 (15)	0.0627 (14)	0.0107 (13)	0.0138 (13)	−0.0163 (12)
C12	0.0650 (14)	0.0486 (13)	0.0501 (12)	−0.0003 (11)	0.0095 (11)	−0.0058 (11)
C13	0.0491 (12)	0.0433 (12)	0.0326 (10)	0.0044 (10)	0.0040 (9)	−0.0031 (9)
C14	0.0507 (13)	0.0471 (12)	0.0432 (11)	0.0046 (10)	0.0117 (10)	−0.0023 (10)
C15	0.0467 (12)	0.0411 (12)	0.0387 (10)	−0.0024 (10)	0.0045 (9)	0.0007 (9)
C16	0.0442 (11)	0.0322 (10)	0.0355 (10)	−0.0003 (9)	0.0054 (9)	0.0007 (8)
C17	0.0487 (12)	0.0338 (11)	0.0389 (10)	0.0016 (9)	0.0067 (9)	−0.0002 (9)
C18	0.0516 (12)	0.0346 (11)	0.0364 (10)	−0.0028 (9)	0.0071 (9)	0.0014 (9)
C19	0.0993 (19)	0.0351 (12)	0.0549 (13)	−0.0007 (12)	0.0227 (13)	0.0042 (10)
C20	0.0792 (17)	0.0462 (13)	0.0755 (16)	0.0218 (12)	0.0231 (14)	0.0020 (12)
C21	0.0409 (11)	0.0381 (11)	0.0455 (11)	0.0038 (9)	0.0134 (9)	0.0013 (9)
C22	0.0476 (12)	0.0478 (13)	0.0577 (13)	−0.0035 (10)	0.0119 (10)	0.0013 (11)
C23	0.0524 (14)	0.0574 (14)	0.0797 (17)	−0.0037 (12)	0.0261 (13)	0.0167 (13)
C24	0.0695 (16)	0.0742 (17)	0.0531 (14)	0.0107 (14)	0.0280 (12)	0.0104 (13)
C25	0.0736 (16)	0.0647 (16)	0.0479 (13)	0.0043 (13)	0.0174 (12)	−0.0040 (12)
C26	0.0536 (13)	0.0498 (13)	0.0510 (12)	−0.0039 (11)	0.0135 (10)	−0.0041 (10)

Geometric parameters (Å, º) top

O1—C6	1.366 (3)	C10—C11	1.375 (3)
O1—C7	1.428 (3)	C10—H10	0.9300
O2—C9	1.372 (3)	C11—C12	1.379 (3)
O2—C8	1.426 (2)	C11—H11	0.9300
O3—C17	1.233 (2)	C12—C13	1.386 (3)
N1—C15	1.280 (2)	C12—H12	0.9300
N1—C16	1.396 (2)	C13—C14	1.386 (3)
N2—C17	1.398 (2)	C13—C15	1.460 (3)
N2—N3	1.406 (2)	C14—H14	0.9300
N2—C21	1.429 (2)	C15—H15	0.9300
N3—C18	1.361 (2)	C16—C18	1.365 (2)
N3—C20	1.459 (2)	C16—C17	1.437 (3)
C1—C2	1.374 (3)	C18—C19	1.477 (3)
C1—C6	1.376 (3)	C19—H19A	0.9600
C1—H1	0.9300	C19—H19B	0.9600
C2—C3	1.370 (3)	C19—H19C	0.9600
C2—H2	0.9300	C20—H20A	0.9600
C3—C4	1.383 (4)	C20—H20B	0.9600
C3—H3	0.9300	C20—H20C	0.9600
C4—C5	1.366 (3)	C21—C26	1.376 (3)
C4—H4	0.9300	C21—C22	1.378 (3)
C5—C6	1.385 (3)	C22—C23	1.391 (3)
C5—H5	0.9300	C22—H22	0.9300
C7—C8	1.483 (3)	C23—C24	1.372 (3)
C7—H7A	0.9700	C23—H23	0.9300
C7—H7B	0.9700	C24—C25	1.368 (3)
C8—H8A	0.9700	C24—H24	0.9300
C8—H8B	0.9700	C25—C26	1.389 (3)
C9—C14	1.382 (3)	C25—H25	0.9300
C9—C10	1.384 (3)	C26—H26	0.9300

C6—O1—C7	118.38 (18)	C13—C12—H12	120.0
C9—O2—C8	117.34 (18)	C14—C13—C12	118.71 (18)
C15—N1—C16	121.05 (16)	C14—C13—C15	121.13 (17)
C17—N2—N3	109.01 (14)	C12—C13—C15	120.12 (18)
C17—N2—C21	122.43 (15)	C9—C14—C13	121.0 (2)
N3—N2—C21	119.69 (15)	C9—C14—H14	119.5
C18—N3—N2	107.17 (14)	C13—C14—H14	119.5
C18—N3—C20	124.78 (16)	N1—C15—C13	121.49 (18)
N2—N3—C20	118.06 (16)	N1—C15—H15	119.3
C2—C1—C6	119.5 (2)	C13—C15—H15	119.3
C2—C1—H1	120.2	C18—C16—N1	121.96 (16)
C6—C1—H1	120.2	C18—C16—C17	108.14 (16)
C3—C2—C1	121.5 (2)	N1—C16—C17	129.72 (17)
C3—C2—H2	119.3	O3—C17—N2	123.26 (17)
C1—C2—H2	119.3	O3—C17—C16	131.58 (17)
C2—C3—C4	118.6 (3)	N2—C17—C16	105.10 (16)
C2—C3—H3	120.7	N3—C18—C16	110.11 (16)
C4—C3—H3	120.7	N3—C18—C19	122.35 (17)
C5—C4—C3	120.8 (2)	C16—C18—C19	127.54 (17)
C5—C4—H4	119.6	C18—C19—H19A	109.5
C3—C4—H4	119.6	C18—C19—H19B	109.5
C4—C5—C6	120.0 (2)	H19A—C19—H19B	109.5
C4—C5—H5	120.0	C18—C19—H19C	109.5
C6—C5—H5	120.0	H19A—C19—H19C	109.5
O1—C6—C1	124.9 (2)	H19B—C19—H19C	109.5
O1—C6—C5	115.5 (2)	N3—C20—H20A	109.5
C1—C6—C5	119.6 (2)	N3—C20—H20B	109.5
O1—C7—C8	109.1 (2)	H20A—C20—H20B	109.5
O1—C7—H7A	109.9	N3—C20—H20C	109.5
C8—C7—H7A	109.9	H20A—C20—H20C	109.5
O1—C7—H7B	109.9	H20B—C20—H20C	109.5
C8—C7—H7B	109.9	C26—C21—C22	120.94 (18)
H7A—C7—H7B	108.3	C26—C21—N2	121.11 (17)
O2—C8—C7	108.0 (2)	C22—C21—N2	117.90 (18)
O2—C8—H8A	110.1	C21—C22—C23	119.0 (2)
C7—C8—H8A	110.1	C21—C22—H22	120.5
O2—C8—H8B	110.1	C23—C22—H22	120.5
C7—C8—H8B	110.1	C24—C23—C22	120.1 (2)
H8A—C8—H8B	108.4	C24—C23—H23	119.9
O2—C9—C14	115.46 (19)	C22—C23—H23	119.9
O2—C9—C10	124.61 (19)	C25—C24—C23	120.5 (2)
C14—C9—C10	119.9 (2)	C25—C24—H24	119.8
C11—C10—C9	119.1 (2)	C23—C24—H24	119.8
C11—C10—H10	120.4	C24—C25—C26	120.2 (2)
C9—C10—H10	120.4	C24—C25—H25	119.9
C10—C11—C12	121.2 (2)	C26—C25—H25	119.9
C10—C11—H11	119.4	C21—C26—C25	119.2 (2)
C12—C11—H11	119.4	C21—C26—H26	120.4
C11—C12—C13	120.1 (2)	C25—C26—H26	120.4
C11—C12—H12	120.0

C17—N2—N3—C18	−7.2 (2)	C12—C13—C15—N1	179.35 (19)
C21—N2—N3—C18	−155.35 (17)	C15—N1—C16—C18	175.00 (18)
C17—N2—N3—C20	−154.48 (18)	C15—N1—C16—C17	−10.6 (3)
C21—N2—N3—C20	57.4 (2)	N3—N2—C17—O3	−171.82 (18)
C6—C1—C2—C3	0.1 (3)	C21—N2—C17—O3	−24.7 (3)
C1—C2—C3—C4	−1.0 (4)	N3—N2—C17—C16	5.57 (19)
C2—C3—C4—C5	0.7 (4)	C21—N2—C17—C16	152.65 (17)
C3—C4—C5—C6	0.5 (4)	C18—C16—C17—O3	175.1 (2)
C7—O1—C6—C1	10.6 (3)	N1—C16—C17—O3	0.1 (4)
C7—O1—C6—C5	−169.1 (2)	C18—C16—C17—N2	−1.9 (2)
C2—C1—C6—O1	−178.7 (2)	N1—C16—C17—N2	−176.97 (18)
C2—C1—C6—C5	1.1 (3)	N2—N3—C18—C16	6.0 (2)
C4—C5—C6—O1	178.4 (2)	C20—N3—C18—C16	150.45 (19)
C4—C5—C6—C1	−1.4 (3)	N2—N3—C18—C19	−173.80 (18)
C6—O1—C7—C8	166.89 (18)	C20—N3—C18—C19	−29.3 (3)
C9—O2—C8—C7	173.30 (19)	N1—C16—C18—N3	172.97 (16)
O1—C7—C8—O2	72.1 (2)	C17—C16—C18—N3	−2.5 (2)
C8—O2—C9—C14	−174.90 (19)	N1—C16—C18—C19	−7.3 (3)
C8—O2—C9—C10	4.1 (3)	C17—C16—C18—C19	177.2 (2)
O2—C9—C10—C11	−179.3 (2)	C17—N2—C21—C26	−111.9 (2)
C14—C9—C10—C11	−0.4 (3)	N3—N2—C21—C26	31.8 (3)
C9—C10—C11—C12	0.0 (3)	C17—N2—C21—C22	65.3 (3)
C10—C11—C12—C13	0.0 (3)	N3—N2—C21—C22	−150.92 (18)
C11—C12—C13—C14	0.4 (3)	C26—C21—C22—C23	0.9 (3)
C11—C12—C13—C15	178.27 (19)	N2—C21—C22—C23	−176.37 (18)
O2—C9—C14—C13	179.84 (18)	C21—C22—C23—C24	−1.0 (3)
C10—C9—C14—C13	0.8 (3)	C22—C23—C24—C25	0.2 (4)
C12—C13—C14—C9	−0.8 (3)	C23—C24—C25—C26	0.9 (4)
C15—C13—C14—C9	−178.66 (18)	C22—C21—C26—C25	0.1 (3)
C16—N1—C15—C13	175.64 (16)	N2—C21—C26—C25	177.31 (19)
C14—C13—C15—N1	−2.8 (3)	C24—C25—C26—C21	−1.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···O3ⁱ	0.96	2.31	3.137 (2)	144
C25—H25···O3ⁱⁱ	0.93	2.45	3.368 (3)	169

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

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

(E)-1,5-Dimethyl-4-[3-(2-phenoxy­ethoxy)benzyl­ideneamino]-2-phenyl-1H-pyrazol-3(2H)-one

Supporting information

Key indicators

checkCIF/PLATON results

(E)-1,5-Dimethyl-4-[3-(2-phenoxyethoxy)benzylideneamino]-2-phenyl-1H-pyrazol-3(2H)-one