(E,E)-3,3'-Dimethyl-1,1'-diphenyl-4,4'-{(ethane-1,2-diyldiimino)-bis-[(2-fur-yl)methyl-idyne]}di-1H-pyrazol-5(4H)-one.

The complete molecule of the title compound of the title compound, C(32)H(28)N(6)O(4), is generated by crystallographic inversion symmetry. The dihedral angles between the pyrazalone ring and the pendant phenyl and furan rings are 15.65 (8) and 65.06 (8)°, respectively. In the crystal, the molecules are linked by N-H⋯O, C-H⋯O and weak C-H⋯π interactions.

Related literature

For general background to pyrazolo­nes, see: Casas et al. (2007 ▶); Jensen (1959 ▶); Li et al. (2000 ▶); Zhang et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C32H28N6O4

M = 560.60

Monoclinic,

a = 10.7438 (6) Å

b = 7.6999 (4) Å

c = 16.8273 (9) Å

β = 93.937 (1)°

V = 1388.77 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.22 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

8081 measured reflections

3145 independent reflections

1934 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.133

S = 1.02

3145 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681001980X/zq2042sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001980X/zq2042Isup2.hkl

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

C32H28N6O4	F(000) = 588
Mr = 560.60	Dx = 1.341 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1740 reflections
a = 10.7438 (6) Å	θ = 2.4–22.9°
b = 7.6999 (4) Å	µ = 0.09 mm−1
c = 16.8273 (9) Å	T = 295 K
β = 93.937 (1)°	Block, yellow
V = 1388.77 (13) Å3	0.22 × 0.20 × 0.20 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	1934 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 27.5°, θmin = 1.9°
phi and ω scans	h = −12→13
8081 measured reflections	k = −10→6
3145 independent reflections	l = −21→21

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0585P)2 + 0.2282P] where P = (Fo2 + 2Fc2)/3
3145 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.21 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
C1	0.79340 (17)	1.2879 (2)	0.11911 (11)	0.0503 (4)
C2	0.86997 (19)	1.2531 (3)	0.18661 (11)	0.0628 (5)
H2	0.9052	1.1435	0.1942	0.075*
C3	0.8939 (2)	1.3819 (4)	0.24275 (14)	0.0784 (7)
H3	0.9448	1.3584	0.2884	0.094*
C4	0.8430 (2)	1.5442 (4)	0.23149 (16)	0.0832 (8)
H4	0.8600	1.6308	0.2692	0.100*
C5	0.7671 (2)	1.5788 (3)	0.16450 (15)	0.0755 (7)
H5	0.7329	1.6890	0.1570	0.091*
C6	0.74101 (18)	1.4516 (3)	0.10811 (13)	0.0598 (5)
H6	0.6887	1.4753	0.0631	0.072*
C7	0.83098 (17)	1.0057 (2)	0.04804 (11)	0.0494 (4)
C8	0.76317 (16)	0.9266 (2)	−0.01917 (10)	0.0477 (4)
C9	0.66731 (17)	1.0489 (3)	−0.04361 (11)	0.0529 (5)
C10	0.5737 (2)	1.0478 (3)	−0.11395 (13)	0.0757 (7)
H10A	0.5098	0.9640	−0.1054	0.114*
H10B	0.6145	1.0178	−0.1610	0.114*
H10C	0.5369	1.1610	−0.1204	0.114*
C11	0.79841 (15)	0.7652 (2)	−0.04839 (10)	0.0453 (4)
C12	0.71716 (18)	0.6668 (2)	−0.10479 (10)	0.0510 (5)
C13	0.59548 (17)	0.6410 (3)	−0.10780 (11)	0.0566 (5)
H13	0.5408	0.6837	−0.0720	0.068*
C14	0.5636 (2)	0.5375 (3)	−0.17468 (13)	0.0728 (6)
H14	0.4841	0.4988	−0.1915	0.087*
C15	0.6675 (2)	0.5054 (3)	−0.20900 (13)	0.0743 (6)
H15	0.6733	0.4402	−0.2551	0.089*
C16	0.95252 (16)	0.5224 (2)	−0.03384 (11)	0.0498 (5)
H16A	0.9908	0.5153	−0.0843	0.060*
H16B	0.8836	0.4408	−0.0350	0.060*
H3A	0.9502 (18)	0.768 (3)	0.0148 (12)	0.072 (6)*
N1	0.76746 (14)	1.1578 (2)	0.06110 (8)	0.0525 (4)
N2	0.67014 (15)	1.1852 (2)	0.00285 (9)	0.0586 (4)
N3	0.90719 (14)	0.6974 (2)	−0.02175 (10)	0.0523 (4)
O1	0.92691 (12)	0.95452 (17)	0.08686 (8)	0.0615 (4)
O2	0.76644 (13)	0.5832 (2)	−0.16638 (8)	0.0703 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0526 (10)	0.0503 (11)	0.0489 (10)	−0.0084 (9)	0.0096 (8)	−0.0029 (9)
C2	0.0687 (13)	0.0644 (13)	0.0550 (11)	−0.0098 (11)	0.0030 (10)	−0.0045 (10)
C3	0.0795 (15)	0.0934 (19)	0.0622 (14)	−0.0174 (14)	0.0041 (11)	−0.0200 (13)
C4	0.0753 (15)	0.0879 (19)	0.0887 (18)	−0.0172 (14)	0.0219 (14)	−0.0418 (15)
C5	0.0656 (13)	0.0618 (14)	0.1014 (18)	−0.0080 (11)	0.0215 (13)	−0.0244 (13)
C6	0.0572 (11)	0.0562 (12)	0.0673 (12)	−0.0035 (10)	0.0143 (10)	−0.0061 (10)
C7	0.0528 (10)	0.0465 (10)	0.0481 (10)	0.0005 (9)	−0.0017 (8)	0.0039 (8)
C8	0.0505 (10)	0.0465 (10)	0.0452 (9)	0.0000 (8)	−0.0029 (8)	0.0006 (8)
C9	0.0550 (11)	0.0534 (11)	0.0490 (10)	0.0044 (9)	−0.0051 (8)	0.0015 (9)
C10	0.0822 (15)	0.0761 (16)	0.0647 (13)	0.0176 (13)	−0.0249 (11)	−0.0040 (12)
C11	0.0472 (10)	0.0460 (10)	0.0426 (9)	−0.0017 (8)	0.0022 (8)	0.0051 (8)
C12	0.0622 (12)	0.0480 (10)	0.0425 (9)	−0.0011 (9)	0.0002 (8)	−0.0025 (8)
C13	0.0475 (10)	0.0667 (13)	0.0559 (11)	0.0026 (9)	0.0049 (8)	−0.0122 (10)
C14	0.0565 (12)	0.0862 (17)	0.0741 (14)	−0.0062 (12)	−0.0086 (11)	−0.0161 (12)
C15	0.0718 (14)	0.0852 (16)	0.0641 (13)	−0.0018 (13)	−0.0076 (11)	−0.0288 (12)
C16	0.0482 (10)	0.0454 (10)	0.0561 (11)	−0.0007 (8)	0.0052 (8)	−0.0022 (8)
N1	0.0594 (9)	0.0474 (9)	0.0494 (9)	0.0036 (8)	−0.0063 (7)	−0.0026 (7)
N2	0.0625 (10)	0.0552 (10)	0.0564 (9)	0.0090 (8)	−0.0087 (8)	−0.0015 (8)
N3	0.0497 (9)	0.0426 (9)	0.0636 (10)	−0.0014 (7)	−0.0020 (8)	−0.0042 (8)
O1	0.0619 (8)	0.0561 (8)	0.0635 (8)	0.0046 (7)	−0.0177 (7)	−0.0037 (7)
O2	0.0630 (9)	0.0847 (11)	0.0632 (9)	0.0002 (8)	0.0047 (7)	−0.0147 (8)

C1—C2	1.382 (3)	C10—H10A	0.9600
C1—C6	1.387 (3)	C10—H10B	0.9600
C1—N1	1.413 (2)	C10—H10C	0.9600
C2—C3	1.382 (3)	C11—N3	1.330 (2)
C2—H2	0.9300	C11—C12	1.457 (2)
C3—C4	1.372 (4)	C12—C13	1.320 (2)
C3—H3	0.9300	C12—O2	1.358 (2)
C4—C5	1.371 (4)	C13—C14	1.402 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.379 (3)	C14—C15	1.315 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—O2	1.378 (2)
C7—O1	1.246 (2)	C15—H15	0.9300
C7—N1	1.380 (2)	C16—N3	1.452 (2)
C7—C8	1.438 (2)	C16—C16i	1.516 (3)
C8—C11	1.398 (3)	C16—H16A	0.9700
C8—C9	1.435 (2)	C16—H16B	0.9700
C9—N2	1.307 (2)	N1—N2	1.399 (2)
C9—C10	1.500 (2)	N3—H3A	0.92 (2)
C2—C1—C6	119.95 (18)	H10A—C10—H10C	109.5
C2—C1—N1	120.52 (18)	H10B—C10—H10C	109.5
C6—C1—N1	119.54 (17)	N3—C11—C8	118.92 (16)
C3—C2—C1	119.7 (2)	N3—C11—C12	119.25 (17)
C3—C2—H2	120.2	C8—C11—C12	121.79 (16)
C1—C2—H2	120.2	C13—C12—O2	109.65 (16)
C4—C3—C2	120.4 (2)	C13—C12—C11	130.61 (17)
C4—C3—H3	119.8	O2—C12—C11	119.74 (16)
C2—C3—H3	119.8	C12—C13—C14	107.65 (18)
C5—C4—C3	119.9 (2)	C12—C13—H13	126.2
C5—C4—H4	120.0	C14—C13—H13	126.2
C3—C4—H4	120.0	C15—C14—C13	106.94 (18)
C4—C5—C6	120.6 (2)	C15—C14—H14	126.5
C4—C5—H5	119.7	C13—C14—H14	126.5
C6—C5—H5	119.7	C14—C15—O2	109.74 (18)
C5—C6—C1	119.5 (2)	C14—C15—H15	125.1
C5—C6—H6	120.3	O2—C15—H15	125.1
C1—C6—H6	120.3	N3—C16—C16i	108.70 (18)
O1—C7—N1	125.83 (17)	N3—C16—H16A	109.9
O1—C7—C8	129.37 (17)	C16i—C16—H16A	109.9
N1—C7—C8	104.79 (15)	N3—C16—H16B	109.9
C11—C8—C9	133.55 (16)	C16i—C16—H16B	109.9
C11—C8—C7	121.23 (16)	H16A—C16—H16B	108.3
C9—C8—C7	105.20 (16)	C7—N1—N2	111.73 (14)
N2—C9—C8	111.62 (16)	C7—N1—C1	129.44 (15)
N2—C9—C10	117.60 (17)	N2—N1—C1	118.64 (15)
C8—C9—C10	130.68 (18)	C9—N2—N1	106.47 (15)
C9—C10—H10A	109.5	C11—N3—C16	127.80 (16)
C9—C10—H10B	109.5	C11—N3—H3A	112.4 (12)
H10A—C10—H10B	109.5	C16—N3—H3A	119.0 (13)
C9—C10—H10C	109.5	C12—O2—C15	106.01 (15)
C6—C1—C2—C3	−0.1 (3)	C8—C11—C12—O2	139.07 (18)
N1—C1—C2—C3	−179.80 (18)	O2—C12—C13—C14	−0.6 (2)
C1—C2—C3—C4	−0.6 (3)	C11—C12—C13—C14	179.5 (2)
C2—C3—C4—C5	0.6 (4)	C12—C13—C14—C15	0.0 (3)
C3—C4—C5—C6	0.1 (3)	C13—C14—C15—O2	0.6 (3)
C4—C5—C6—C1	−0.7 (3)	O1—C7—N1—N2	174.61 (17)
C2—C1—C6—C5	0.7 (3)	C8—C7—N1—N2	−4.5 (2)
N1—C1—C6—C5	−179.56 (17)	O1—C7—N1—C1	−0.1 (3)
O1—C7—C8—C11	3.0 (3)	C8—C7—N1—C1	−179.26 (17)
N1—C7—C8—C11	−177.92 (16)	C2—C1—N1—C7	−19.0 (3)
O1—C7—C8—C9	−175.32 (19)	C6—C1—N1—C7	161.30 (18)
N1—C7—C8—C9	3.75 (19)	C2—C1—N1—N2	166.60 (16)
C11—C8—C9—N2	−179.9 (2)	C6—C1—N1—N2	−13.1 (2)
C7—C8—C9—N2	−1.9 (2)	C8—C9—N2—N1	−0.8 (2)
C11—C8—C9—C10	−3.7 (4)	C10—C9—N2—N1	−177.56 (17)
C7—C8—C9—C10	174.3 (2)	C7—N1—N2—C9	3.4 (2)
C9—C8—C11—N3	167.09 (19)	C1—N1—N2—C9	178.82 (16)
C7—C8—C11—N3	−10.7 (3)	C8—C11—N3—C16	169.17 (17)
C9—C8—C11—C12	−15.3 (3)	C12—C11—N3—C16	−8.5 (3)
C7—C8—C11—C12	166.92 (16)	C16i—C16—N3—C11	−154.74 (19)
N3—C11—C12—C13	136.6 (2)	C13—C12—O2—C15	0.9 (2)
C8—C11—C12—C13	−41.0 (3)	C11—C12—O2—C15	−179.14 (18)
N3—C11—C12—O2	−43.3 (2)	C14—C15—O2—C12	−0.9 (3)

Cg3 is the centroid of the C1–c6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.92 (2)	1.91 (2)	2.693 (2)	142.0 (17)
C16—H16A···Cg3ii	0.97	2.70	3.575 (2)	151
C3—H3···O1iii	0.93	2.54	3.389 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.92 (2)	1.91 (2)	2.693 (2)	142.0 (17)
C16—H16A⋯Cg3i	0.97	2.70	3.575 (2)	151
C3—H3⋯O1ii	0.93	2.54	3.389 (2)	152

Symmetry codes: (i) ; (ii) .