4-[(E)-4-(2-{4-[(E)-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino­meth­yl]phen­oxy}eth­oxy)benzyl­ideneamino]-1,5-dimethyl-1-phenyl-1H-dihydro­pyrazol-3(2H)-one

In the title compound, C₃₈H₃₆N₆O₄, a crystallographic center of symmetry is located at the mid-point of the central C—C bond. The 4-hydroxy­benzaldehyde residue makes dihedral angles of 8.09 (9) and 68.93 (7)°, respectively, with the pyrazolone ring and the terminal phenyl ring. The crystal packing is stabilized by inter­molecular C—H...O hydrogen bonds that link mol­ecules into one-dimensional extended chains.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.044
• wR factor = 0.131
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

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Computing details

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.

4-[(E)-4-(2-{4-[(E)-(1,5-Dimethyl-3-oxo-2-phenyl-2,3- dihydro-1H-pyrazol-4-yl)iminomethyl]phenoxy}ethoxy)benzylideneamino]- 1,5-dimethyl-1-phenyl-1H-dihydropyrazol-3(2H)-one

Crystal data

C38H36N6O4	F(000) = 676
Mr = 640.73	Dx = 1.288 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2144 reflections
a = 13.199 (5) Å	θ = 2.2–23.3°
b = 6.802 (3) Å	µ = 0.09 mm^−1
c = 18.841 (7) Å	T = 294 K
β = 102.315 (7)°	Block, yellow
V = 1652.6 (11) Å^3	0.38 × 0.26 × 0.20 mm
Z = 2

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3383 independent reflections
Radiation source: fine-focus sealed tube	1892 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→15
Tmin = 0.951, Tmax = 0.983	k = −8→4
9053 measured reflections	l = −23→22

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0603P)^2 + 0.1695P] where P = (Fo^2 + 2Fc^2)/3
3383 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.91514 (11)	0.1946 (2)	0.01277 (9)	0.0654 (5)
O2	0.30821 (11)	0.2863 (2)	0.10057 (8)	0.0572 (4)
N1	0.51533 (12)	0.5312 (2)	0.11079 (9)	0.0455 (4)
N2	0.31753 (13)	0.7313 (2)	0.19154 (9)	0.0468 (5)
N3	0.26376 (12)	0.5639 (2)	0.15964 (9)	0.0440 (4)
C1	0.94305 (16)	−0.0018 (3)	−0.00031 (13)	0.0609 (7)
H1A	0.9040	−0.0474	−0.0470	0.073*
H1B	0.9291	−0.0888	0.0373	0.073*
C2	0.81793 (15)	0.2271 (3)	0.02622 (12)	0.0483 (5)
C3	0.80292 (16)	0.4106 (3)	0.05371 (13)	0.0609 (7)
H3	0.8562	0.5027	0.0608	0.073*
C4	0.70930 (16)	0.4576 (3)	0.07060 (13)	0.0550 (6)
H4	0.7003	0.5811	0.0895	0.066*
C5	0.62822 (15)	0.3235 (3)	0.05984 (11)	0.0414 (5)
C6	0.64485 (16)	0.1416 (3)	0.03118 (12)	0.0511 (6)
H6	0.5913	0.0499	0.0231	0.061*
C7	0.73897 (16)	0.0919 (3)	0.01417 (11)	0.0506 (6)
H7	0.7483	−0.0310	−0.0051	0.061*
C8	0.52845 (15)	0.3704 (3)	0.07831 (11)	0.0449 (5)
H8	0.4737	0.2820	0.0663	0.054*
C9	0.42172 (15)	0.5723 (3)	0.13098 (10)	0.0401 (5)
C10	0.40827 (15)	0.7395 (3)	0.16863 (11)	0.0434 (5)
C11	0.33060 (15)	0.4529 (3)	0.12541 (11)	0.0427 (5)
C12	0.47896 (18)	0.9100 (3)	0.18505 (14)	0.0650 (7)
H12A	0.4450	1.0254	0.1620	0.097*
H12B	0.5406	0.8854	0.1671	0.097*
H12C	0.4972	0.9301	0.2366	0.097*
C13	0.25641 (18)	0.9012 (3)	0.20473 (14)	0.0669 (7)
H13A	0.3004	0.9931	0.2356	0.100*
H13B	0.2021	0.8588	0.2280	0.100*
H13C	0.2265	0.9633	0.1593	0.100*
C14	0.19317 (15)	0.4697 (3)	0.19712 (11)	0.0424 (5)
C15	0.21201 (17)	0.4641 (3)	0.27209 (12)	0.0511 (6)
H15	0.2695	0.5279	0.2997	0.061*
C16	0.14445 (19)	0.3625 (3)	0.30571 (14)	0.0627 (7)
H16	0.1563	0.3587	0.3561	0.075*
C17	0.05970 (19)	0.2670 (3)	0.26485 (16)	0.0644 (7)
H17	0.0150	0.1975	0.2877	0.077*
C18	0.04141 (19)	0.2747 (3)	0.19042 (16)	0.0652 (7)
H18	−0.0159	0.2102	0.1630	0.078*
C19	0.10713 (16)	0.3771 (3)	0.15589 (12)	0.0527 (6)
H19	0.0937	0.3839	0.1055	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0406 (9)	0.0658 (10)	0.0953 (13)	0.0097 (7)	0.0273 (9)	−0.0176 (9)
O2	0.0596 (10)	0.0461 (9)	0.0720 (11)	−0.0055 (7)	0.0276 (8)	−0.0168 (8)
N1	0.0414 (10)	0.0515 (11)	0.0466 (11)	0.0075 (8)	0.0162 (8)	−0.0004 (8)
N2	0.0473 (11)	0.0389 (10)	0.0600 (12)	0.0015 (8)	0.0245 (9)	−0.0073 (8)
N3	0.0429 (10)	0.0411 (10)	0.0529 (11)	−0.0015 (8)	0.0211 (8)	−0.0078 (8)
C1	0.0448 (13)	0.0716 (16)	0.0695 (17)	0.0146 (11)	0.0196 (12)	−0.0179 (12)
C2	0.0330 (12)	0.0608 (14)	0.0527 (14)	0.0100 (10)	0.0126 (10)	−0.0061 (11)
C3	0.0405 (13)	0.0532 (14)	0.0930 (19)	−0.0015 (11)	0.0229 (12)	−0.0144 (13)
C4	0.0456 (13)	0.0479 (13)	0.0747 (17)	0.0076 (10)	0.0204 (12)	−0.0107 (11)
C5	0.0349 (11)	0.0506 (12)	0.0395 (12)	0.0076 (9)	0.0095 (9)	−0.0006 (9)
C6	0.0357 (12)	0.0579 (13)	0.0592 (15)	−0.0001 (10)	0.0087 (10)	−0.0122 (11)
C7	0.0411 (12)	0.0577 (14)	0.0530 (14)	0.0090 (11)	0.0097 (10)	−0.0169 (11)
C8	0.0406 (12)	0.0513 (13)	0.0447 (13)	0.0056 (10)	0.0132 (10)	−0.0004 (10)
C9	0.0388 (11)	0.0447 (12)	0.0393 (12)	0.0055 (9)	0.0139 (9)	−0.0003 (9)
C10	0.0425 (12)	0.0450 (12)	0.0445 (13)	0.0008 (9)	0.0136 (10)	0.0016 (10)
C11	0.0447 (12)	0.0430 (12)	0.0434 (12)	0.0063 (10)	0.0160 (10)	−0.0021 (10)
C12	0.0622 (16)	0.0591 (15)	0.0785 (18)	−0.0125 (12)	0.0260 (13)	−0.0125 (12)
C13	0.0742 (17)	0.0449 (13)	0.092 (2)	0.0118 (12)	0.0399 (15)	−0.0077 (12)
C14	0.0385 (12)	0.0404 (11)	0.0531 (14)	0.0052 (9)	0.0203 (10)	−0.0020 (9)
C15	0.0441 (13)	0.0586 (14)	0.0523 (14)	0.0011 (10)	0.0141 (10)	−0.0005 (11)
C16	0.0678 (16)	0.0665 (16)	0.0607 (16)	0.0073 (13)	0.0292 (13)	0.0089 (12)
C17	0.0594 (16)	0.0537 (15)	0.089 (2)	−0.0051 (12)	0.0363 (15)	0.0059 (14)
C18	0.0525 (15)	0.0620 (15)	0.084 (2)	−0.0118 (12)	0.0217 (14)	−0.0112 (14)
C19	0.0483 (13)	0.0565 (13)	0.0544 (15)	−0.0026 (11)	0.0137 (11)	−0.0078 (11)

Geometric parameters (Å, º)

O1—C2	1.378 (2)	C7—H7	0.9300
O1—C1	1.421 (3)	C8—H8	0.9300
O2—C11	1.238 (2)	C9—C10	1.372 (3)
N1—C8	1.283 (2)	C9—C11	1.436 (3)
N1—C9	1.396 (2)	C10—C12	1.479 (3)
N2—C10	1.358 (2)	C12—H12A	0.9600
N2—N3	1.407 (2)	C12—H12B	0.9600
N2—C13	1.460 (2)	C12—H12C	0.9600
N3—C11	1.417 (2)	C13—H13A	0.9600
N3—C14	1.435 (2)	C13—H13B	0.9600
C1—C1^i	1.501 (4)	C13—H13C	0.9600
C1—H1A	0.9700	C14—C15	1.382 (3)
C1—H1B	0.9700	C14—C19	1.383 (3)
C2—C7	1.372 (3)	C15—C16	1.384 (3)
C2—C3	1.382 (3)	C15—H15	0.9300
C3—C4	1.378 (3)	C16—C17	1.378 (3)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.388 (3)	C17—C18	1.372 (3)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.386 (3)	C18—C19	1.379 (3)
C5—C8	1.467 (3)	C18—H18	0.9300
C6—C7	1.389 (3)	C19—H19	0.9300
C6—H6	0.9300
C2—O1—C1	117.93 (17)	N1—C9—C11	129.99 (18)
C8—N1—C9	121.18 (17)	N2—C10—C9	110.52 (17)
C10—N2—N3	107.22 (15)	N2—C10—C12	121.68 (18)
C10—N2—C13	125.33 (17)	C9—C10—C12	127.79 (19)
N3—N2—C13	117.79 (17)	O2—C11—N3	122.60 (18)
N2—N3—C11	108.63 (15)	O2—C11—C9	132.38 (18)
N2—N3—C14	118.21 (15)	N3—C11—C9	104.97 (17)
C11—N3—C14	121.24 (16)	C10—C12—H12A	109.5
O1—C1—C1^i	106.2 (2)	C10—C12—H12B	109.5
O1—C1—H1A	110.5	H12A—C12—H12B	109.5
C1^i—C1—H1A	110.5	C10—C12—H12C	109.5
O1—C1—H1B	110.5	H12A—C12—H12C	109.5
C1^i—C1—H1B	110.5	H12B—C12—H12C	109.5
H1A—C1—H1B	108.7	N2—C13—H13A	109.5
C7—C2—O1	124.52 (19)	N2—C13—H13B	109.5
C7—C2—C3	120.19 (18)	H13A—C13—H13B	109.5
O1—C2—C3	115.29 (18)	N2—C13—H13C	109.5
C4—C3—C2	120.2 (2)	H13A—C13—H13C	109.5
C4—C3—H3	119.9	H13B—C13—H13C	109.5
C2—C3—H3	119.9	C15—C14—C19	120.6 (2)
C3—C4—C5	121.0 (2)	C15—C14—N3	121.43 (19)
C3—C4—H4	119.5	C19—C14—N3	117.94 (19)
C5—C4—H4	119.5	C14—C15—C16	119.3 (2)
C6—C5—C4	117.54 (18)	C14—C15—H15	120.4
C6—C5—C8	120.74 (18)	C16—C15—H15	120.4
C4—C5—C8	121.72 (19)	C17—C16—C15	120.3 (2)
C5—C6—C7	122.04 (19)	C17—C16—H16	119.8
C5—C6—H6	119.0	C15—C16—H16	119.8
C7—C6—H6	119.0	C18—C17—C16	119.9 (2)
C2—C7—C6	118.95 (19)	C18—C17—H17	120.1
C2—C7—H7	120.5	C16—C17—H17	120.1
C6—C7—H7	120.5	C17—C18—C19	120.7 (2)
N1—C8—C5	121.17 (19)	C17—C18—H18	119.7
N1—C8—H8	119.4	C19—C18—H18	119.7
C5—C8—H8	119.4	C18—C19—C14	119.3 (2)
C10—C9—N1	121.76 (18)	C18—C19—H19	120.4
C10—C9—C11	107.93 (16)	C14—C19—H19	120.4
C10—N2—N3—C11	8.8 (2)	C13—N2—C10—C12	28.0 (3)
C13—N2—N3—C11	156.78 (18)	N1—C9—C10—N2	−170.52 (17)
C10—N2—N3—C14	152.13 (17)	C11—C9—C10—N2	3.6 (2)
C13—N2—N3—C14	−59.9 (2)	N1—C9—C10—C12	8.9 (3)
C2—O1—C1—C1^i	−170.1 (2)	C11—C9—C10—C12	−177.0 (2)
C1—O1—C2—C7	−13.3 (3)	N2—N3—C11—O2	170.99 (18)
C1—O1—C2—C3	166.6 (2)	C14—N3—C11—O2	29.0 (3)
C7—C2—C3—C4	1.3 (3)	N2—N3—C11—C9	−6.5 (2)
O1—C2—C3—C4	−178.6 (2)	C14—N3—C11—C9	−148.50 (18)
C2—C3—C4—C5	−0.6 (4)	C10—C9—C11—O2	−175.2 (2)
C3—C4—C5—C6	−0.3 (3)	N1—C9—C11—O2	−1.8 (4)
C3—C4—C5—C8	179.3 (2)	C10—C9—C11—N3	1.9 (2)
C4—C5—C6—C7	0.6 (3)	N1—C9—C11—N3	175.37 (19)
C8—C5—C6—C7	−179.0 (2)	N2—N3—C14—C15	−33.7 (3)
O1—C2—C7—C6	178.9 (2)	C11—N3—C14—C15	104.8 (2)
C3—C2—C7—C6	−1.1 (3)	N2—N3—C14—C19	148.77 (18)
C5—C6—C7—C2	0.1 (3)	C11—N3—C14—C19	−72.7 (2)
C9—N1—C8—C5	−177.40 (18)	C19—C14—C15—C16	0.8 (3)
C6—C5—C8—N1	173.7 (2)	N3—C14—C15—C16	−176.62 (18)
C4—C5—C8—N1	−5.9 (3)	C14—C15—C16—C17	0.4 (3)
C8—N1—C9—C10	176.99 (19)	C15—C16—C17—C18	−0.8 (4)
C8—N1—C9—C11	4.3 (3)	C16—C17—C18—C19	0.1 (4)
N3—N2—C10—C9	−7.7 (2)	C17—C18—C19—C14	1.2 (3)
C13—N2—C10—C9	−152.6 (2)	C15—C14—C19—C18	−1.6 (3)
N3—N2—C10—C12	172.88 (19)	N3—C14—C19—C18	175.93 (18)

Symmetry code: (i) −x+2, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2^ii	0.93	2.50	3.332 (3)	150

Symmetry code: (ii) −x+1, −y, −z.