(E,E)-3,3′-Dimethyl-1,1′-diphenyl-4,4′-{[3-aza­pentane-1,5-diylbis(aza­nedi­yl)]bis­(phenyl­methyl­idyne)}di-1H-pyrazol-5(4H)-one

Zhang, Z.-P.; Wang, Y.; Li, X.-X.; Li, Y.-W.

doi:10.1107/S1600536810048981

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3326

https://doi.org/10.1107/S1600536810048981

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(E,E)-3,3′-Dimethyl-1,1′-diphenyl-4,4′-{[3-azapentane-1,5-diylbis(azanediyl)]bis(phenylmethylidyne)}di-1H-pyrazol-5(4H)-one

Zhao-Po Zhang,^a Yuan Wang,^a ^* Xiao-Xia Li ^b and Yan-Wei Li ^a

^aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo 454000, People's Republic of China, and ^bInstitute of Functional Materials, Jiangxi University of Finance & Economics, Nanchang 330013, People's Republic of China
^*Correspondence e-mail: wangyuan08@hpu.edu.cn

(Received 21 November 2010; accepted 23 November 2010; online 27 November 2010)

The asymmetric unit of the title compound, C₃₈H₃₇N₇O₂, contains one half-molecule, situated on a twofold rotational axis, in which one amino group is involved in intramolecular N—H⋯O hydrogen bond and the two phenyl rings are twisted from the plane of pyrazolone ring by 26.69 (10) and 79.64 (8)°. The crystal packing exhibits no classical intermolecular contacts.

Related literature

For the synthesis of the title compound and the DNA binding properties of its transition metal complexes, see: Yang et al. (2000 ); Wang & Yang (2005 ). For the similar structure of (E,E)-3,3′-dimethyl-1,1′-diphenyl-4,4′-{(ethane-1,2-diyldiimino)bis[(2-furyl)-methylidyne]}di-1H-pyrazol-5(4H)-one, see: Wang (2010 ).

Experimental

Crystal data

C₃₈H₃₇N₇O₂
M_r = 623.75
Monoclinic, C 2/c
a = 20.3219 (8) Å
b = 8.1990 (2) Å
c = 20.5468 (6) Å
β = 106.748 (2)°
V = 3278.27 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.23 × 0.21 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.982, T_max = 0.988
8269 measured reflections
3765 independent reflections
1886 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.179
S = 1.01
3765 reflections
214 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.86	2.00	2.722 (2)	140

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810048981/cv5005sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048981/cv5005Isup2.hkl

checkCIF report

Comment top

The Schiff bases derivatives of 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone (PMBP) and their metal complexes have been widely studied because of their high biological and pharmaceutical activities (Yang et al., 2000; Wang et al., 2005). For our interest in coordination chemistry, the crystal structure of the title compound was determined by X-ray diffraction analysis.

The asymmetric unit of the title compound contains a half of the molecule situated on a twofold rotational axis. In the independent part of the molecule, one amino group is invloved in intramolecular N—H···O hydrogen bond (Table 1), and two phenyl rings are twisted from the plane of pyrazolone ring at 26.69 (10)° and 79.64 (8)°, respectively. The crystal packing exhibits no classical intermolecular contacts.

Related literature top

For the synthesis of the title compound and the DNA binding properties of its transition metal complexes, see: Yang et al. (2000); Wang et al. (2005). For the similar structure of (E,E)-3,3'-dimethyl-1,1'-diphenyl-4,4'-{(ethane-1,2-diyldiimino)bis[(2-furyl)-methylidyne]}di-1H-pyrazol-5(4H)-one, see: Wang et al. (2010).

Experimental top

The title compound was prepared according to the literature (Wang et al., 2005). 1.1 g (4 mmol) of PMBP were dissolved in EtOH (50 ml), and the EtOH solution containing diethylenetriamine (0.2 g, 2 mmol) was added dropwise. The mixture refluxed on a water bath for 4 h, then part of the solvent was removed on a rotary evaporator. After cooling to 273 K, a large amount of yellow precipitate separated out. Yellow block crystals were obtained by slow evaporation of an ethanol /chloroform (1:1) solution.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure shown with 30% probability displacement ellipsoids. Unlabelled atoms are related with the labelled ones by symmetry operation (-x, y, -z+1/2).

(E,E)-3,3'-Dimethyl-1,1'-diphenyl-4,4'-{[3-azapentane- 1,5-diylbis(azanediyl)]bis(phenylmethylidyne)}di-1H-pyrazol- 5(4H)-one top

Crystal data top

C₃₈H₃₇N₇O₂	F(000) = 1320
M_r = 623.75	D_x = 1.264 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.3219 (8) Å	Cell parameters from 1721 reflections
b = 8.1990 (2) Å	θ = 2.5–22.0°
c = 20.5468 (6) Å	µ = 0.08 mm⁻¹
β = 106.748 (2)°	T = 296 K
V = 3278.27 (18) Å³	Block, yellow
Z = 4	0.23 × 0.21 × 0.15 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3765 independent reflections
Radiation source: fine-focus sealed tube	1886 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
phi and ω scans	θ_max = 27.7°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −26→20
T_min = 0.982, T_max = 0.988	k = −8→10
8269 measured reflections	l = −26→25

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0884P)² + 0.1149P] where P = (F_o² + 2F_c²)/3
3765 reflections	(Δ/σ)_max < 0.001
214 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₃₈H₃₇N₇O₂	V = 3278.27 (18) Å³
M_r = 623.75	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 20.3219 (8) Å	µ = 0.08 mm⁻¹
b = 8.1990 (2) Å	T = 296 K
c = 20.5468 (6) Å	0.23 × 0.21 × 0.15 mm
β = 106.748 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3765 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1886 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.988	R_int = 0.021
8269 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 1.01	Δρ_max = 0.34 e Å⁻³
3765 reflections	Δρ_min = −0.29 e Å⁻³
214 parameters

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 > 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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.06573 (8)	0.23883 (18)	0.35444 (8)	0.0809 (5)
N1	0.14838 (9)	0.0606 (2)	0.41990 (8)	0.0707 (5)
C7	0.12657 (11)	0.1980 (3)	0.38051 (10)	0.0645 (6)
C12	0.25215 (10)	0.4844 (3)	0.32781 (11)	0.0661 (6)
N2	0.21985 (10)	0.0439 (3)	0.43823 (10)	0.0819 (6)
N3	0.12874 (9)	0.4629 (2)	0.29494 (10)	0.0833 (6)
H3A	0.0927	0.4145	0.2992	0.100*
C11	0.18821 (10)	0.4066 (3)	0.33364 (11)	0.0657 (6)
N4	0.0000	0.6106 (3)	0.2500	0.0898 (9)
H4	0.0000	0.5057	0.2500	0.108*
C8	0.18835 (10)	0.2749 (3)	0.37639 (10)	0.0635 (6)
C6	0.10856 (13)	−0.0732 (3)	0.42954 (10)	0.0719 (6)
C17	0.27276 (12)	0.4657 (3)	0.27000 (11)	0.0738 (6)
H17	0.2456	0.4070	0.2333	0.089*
C9	0.24330 (11)	0.1713 (3)	0.41344 (10)	0.0715 (6)
C19	0.06028 (11)	0.7026 (3)	0.25289 (12)	0.0802 (7)
H19A	0.0749	0.7608	0.2958	0.096*
H19B	0.0500	0.7825	0.2165	0.096*
C15	0.37336 (13)	0.6229 (3)	0.32006 (17)	0.0930 (8)
H15	0.4144	0.6685	0.3174	0.112*
C13	0.29269 (12)	0.5747 (3)	0.38196 (12)	0.0822 (7)
H13	0.2791	0.5876	0.4212	0.099*
C16	0.33348 (14)	0.5339 (3)	0.26650 (14)	0.0840 (7)
H16	0.3476	0.5196	0.2277	0.101*
C5	0.04144 (14)	−0.0517 (3)	0.42877 (12)	0.0830 (7)
H5	0.0224	0.0524	0.4239	0.100*
C18	0.11649 (12)	0.5955 (3)	0.24635 (13)	0.0913 (8)
H18A	0.1048	0.5511	0.2007	0.110*
H18B	0.1582	0.6592	0.2535	0.110*
C14	0.35261 (13)	0.6447 (3)	0.37766 (15)	0.0951 (8)
H14	0.3792	0.7068	0.4136	0.114*
C10	0.31871 (12)	0.1867 (4)	0.42487 (13)	0.0961 (8)
H10A	0.3412	0.0905	0.4472	0.144*
H10B	0.3354	0.2803	0.4528	0.144*
H10C	0.3281	0.1991	0.3820	0.144*
C1	0.13730 (17)	−0.2275 (3)	0.43868 (12)	0.0930 (8)
H1	0.1832	−0.2428	0.4409	0.112*
C2	0.0968 (2)	−0.3578 (4)	0.44439 (14)	0.1196 (12)
H2	0.1156	−0.4621	0.4496	0.144*
C4	0.00213 (17)	−0.1842 (4)	0.43516 (14)	0.1080 (9)
H4A	−0.0435	−0.1692	0.4344	0.130*
C3	0.0297 (3)	−0.3380 (5)	0.44262 (15)	0.1220 (12)
H3	0.0030	−0.4276	0.4464	0.146*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0582 (10)	0.0849 (11)	0.0935 (11)	0.0105 (8)	0.0123 (8)	0.0203 (9)
N1	0.0691 (12)	0.0775 (12)	0.0639 (11)	0.0186 (10)	0.0165 (9)	0.0105 (10)
C7	0.0633 (14)	0.0714 (13)	0.0550 (11)	0.0118 (11)	0.0113 (10)	0.0031 (11)
C12	0.0527 (12)	0.0789 (14)	0.0630 (13)	0.0104 (10)	0.0106 (10)	0.0064 (11)
N2	0.0710 (13)	0.1030 (15)	0.0698 (12)	0.0299 (11)	0.0171 (9)	0.0151 (11)
N3	0.0534 (11)	0.0994 (14)	0.0904 (14)	0.0020 (10)	0.0098 (9)	0.0312 (12)
C11	0.0534 (12)	0.0782 (14)	0.0613 (12)	0.0071 (11)	0.0099 (9)	−0.0004 (11)
N4	0.0586 (17)	0.0646 (15)	0.141 (3)	0.000	0.0209 (16)	0.000
C8	0.0578 (13)	0.0768 (14)	0.0529 (11)	0.0114 (11)	0.0109 (9)	0.0040 (11)
C6	0.0888 (17)	0.0736 (15)	0.0502 (11)	0.0087 (13)	0.0153 (11)	0.0050 (11)
C17	0.0676 (15)	0.0905 (16)	0.0623 (13)	0.0129 (12)	0.0171 (11)	0.0103 (12)
C9	0.0635 (14)	0.0937 (16)	0.0556 (12)	0.0222 (13)	0.0144 (10)	0.0047 (12)
C19	0.0640 (15)	0.0849 (15)	0.0790 (15)	−0.0046 (13)	0.0001 (11)	0.0105 (13)
C15	0.0587 (15)	0.0976 (19)	0.118 (2)	0.0060 (14)	0.0185 (15)	0.0314 (18)
C13	0.0626 (14)	0.1095 (18)	0.0691 (14)	0.0038 (14)	0.0101 (11)	−0.0065 (14)
C16	0.0793 (18)	0.0950 (17)	0.0848 (17)	0.0241 (14)	0.0348 (14)	0.0294 (15)
C5	0.0876 (18)	0.0819 (16)	0.0771 (15)	−0.0009 (14)	0.0201 (13)	0.0111 (13)
C18	0.0667 (15)	0.1080 (18)	0.0938 (17)	0.0109 (14)	0.0146 (12)	0.0381 (15)
C14	0.0646 (17)	0.110 (2)	0.101 (2)	−0.0025 (14)	0.0075 (14)	−0.0023 (16)
C10	0.0650 (16)	0.134 (2)	0.0863 (16)	0.0318 (15)	0.0163 (12)	0.0204 (16)
C1	0.136 (2)	0.0787 (17)	0.0666 (14)	0.0274 (17)	0.0325 (15)	0.0120 (13)
C2	0.205 (4)	0.074 (2)	0.0774 (19)	0.014 (2)	0.037 (2)	0.0158 (15)
C4	0.119 (2)	0.105 (2)	0.0920 (19)	−0.020 (2)	0.0188 (16)	0.0229 (17)
C3	0.182 (4)	0.100 (3)	0.0778 (18)	−0.037 (3)	0.026 (2)	0.0155 (17)

Geometric parameters (Å, º) top

O1—C7	1.243 (2)	C19—H19A	0.9700
N1—C7	1.383 (3)	C19—H19B	0.9700
N1—N2	1.398 (2)	C15—C16	1.374 (4)
N1—C6	1.411 (3)	C15—C14	1.378 (4)
C7—C8	1.429 (3)	C15—H15	0.9300
C12—C17	1.377 (3)	C13—C14	1.372 (3)
C12—C13	1.391 (3)	C13—H13	0.9300
C12—C11	1.483 (3)	C16—H16	0.9300
N2—C9	1.310 (3)	C5—C4	1.377 (4)
N3—C11	1.324 (3)	C5—H5	0.9300
N3—C18	1.448 (3)	C18—H18A	0.9700
N3—H3A	0.8600	C18—H18B	0.9700
C11—C8	1.392 (3)	C14—H14	0.9300
N4—C19	1.425 (3)	C10—H10A	0.9600
N4—C19ⁱ	1.425 (3)	C10—H10B	0.9600
N4—H4	0.8600	C10—H10C	0.9600
C8—C9	1.435 (3)	C1—C2	1.375 (4)
C6—C5	1.371 (3)	C1—H1	0.9300
C6—C1	1.384 (3)	C2—C3	1.362 (5)
C17—C16	1.375 (3)	C2—H2	0.9300
C17—H17	0.9300	C4—C3	1.370 (5)
C9—C10	1.487 (3)	C4—H4A	0.9300
C19—C18	1.477 (3)	C3—H3	0.9300

C7—N1—N2	111.73 (18)	C16—C15—H15	120.0
C7—N1—C6	127.98 (19)	C14—C15—H15	120.0
N2—N1—C6	118.64 (18)	C14—C13—C12	120.2 (2)
O1—C7—N1	125.6 (2)	C14—C13—H13	119.9
O1—C7—C8	129.6 (2)	C12—C13—H13	119.9
N1—C7—C8	104.77 (18)	C15—C16—C17	120.3 (2)
C17—C12—C13	119.5 (2)	C15—C16—H16	119.8
C17—C12—C11	120.9 (2)	C17—C16—H16	119.8
C13—C12—C11	119.66 (19)	C6—C5—C4	120.0 (3)
C9—N2—N1	106.44 (17)	C6—C5—H5	120.0
C11—N3—C18	128.4 (2)	C4—C5—H5	120.0
C11—N3—H3A	115.8	N3—C18—C19	111.5 (2)
C18—N3—H3A	115.8	N3—C18—H18A	109.3
N3—C11—C8	119.03 (19)	C19—C18—H18A	109.3
N3—C11—C12	118.1 (2)	N3—C18—H18B	109.3
C8—C11—C12	122.84 (18)	C19—C18—H18B	109.3
C19—N4—C19ⁱ	116.1 (3)	H18A—C18—H18B	108.0
C19—N4—H4	122.0	C13—C14—C15	119.9 (3)
C19ⁱ—N4—H4	122.0	C13—C14—H14	120.1
C11—C8—C7	122.52 (18)	C15—C14—H14	120.1
C11—C8—C9	130.9 (2)	C9—C10—H10A	109.5
C7—C8—C9	105.7 (2)	C9—C10—H10B	109.5
C5—C6—C1	119.9 (2)	H10A—C10—H10B	109.5
C5—C6—N1	120.5 (2)	C9—C10—H10C	109.5
C1—C6—N1	119.6 (2)	H10A—C10—H10C	109.5
C16—C17—C12	120.0 (2)	H10B—C10—H10C	109.5
C16—C17—H17	120.0	C2—C1—C6	118.8 (3)
C12—C17—H17	120.0	C2—C1—H1	120.6
N2—C9—C8	111.3 (2)	C6—C1—H1	120.6
N2—C9—C10	118.7 (2)	C3—C2—C1	121.6 (3)
C8—C9—C10	130.0 (2)	C3—C2—H2	119.2
N4—C19—C18	111.1 (2)	C1—C2—H2	119.2
N4—C19—H19A	109.4	C3—C4—C5	120.4 (3)
C18—C19—H19A	109.4	C3—C4—H4A	119.8
N4—C19—H19B	109.4	C5—C4—H4A	119.8
C18—C19—H19B	109.4	C2—C3—C4	119.1 (3)
H19A—C19—H19B	108.0	C2—C3—H3	120.4
C16—C15—C14	120.1 (2)	C4—C3—H3	120.4

N2—N1—C7—O1	176.4 (2)	C11—C12—C17—C16	−177.64 (19)
C6—N1—C7—O1	11.4 (3)	N1—N2—C9—C8	−1.4 (2)
N2—N1—C7—C8	−2.4 (2)	N1—N2—C9—C10	−179.79 (19)
C6—N1—C7—C8	−167.39 (18)	C11—C8—C9—N2	−168.8 (2)
C7—N1—N2—C9	2.5 (2)	C7—C8—C9—N2	0.0 (2)
C6—N1—N2—C9	169.01 (18)	C11—C8—C9—C10	9.3 (4)
C18—N3—C11—C8	−178.9 (2)	C7—C8—C9—C10	178.1 (2)
C18—N3—C11—C12	−0.7 (3)	C19ⁱ—N4—C19—C18	−172.3 (2)
C17—C12—C11—N3	−69.2 (3)	C17—C12—C13—C14	0.1 (4)
C13—C12—C11—N3	112.2 (2)	C11—C12—C13—C14	178.8 (2)
C17—C12—C11—C8	108.9 (2)	C14—C15—C16—C17	−0.1 (4)
C13—C12—C11—C8	−69.7 (3)	C12—C17—C16—C15	−1.0 (3)
N3—C11—C8—C7	−0.3 (3)	C1—C6—C5—C4	−1.8 (3)
C12—C11—C8—C7	−178.43 (19)	N1—C6—C5—C4	177.1 (2)
N3—C11—C8—C9	166.9 (2)	C11—N3—C18—C19	−135.6 (3)
C12—C11—C8—C9	−11.2 (3)	N4—C19—C18—N3	−52.7 (3)
O1—C7—C8—C11	−7.3 (4)	C12—C13—C14—C15	−1.3 (4)
N1—C7—C8—C11	171.45 (18)	C16—C15—C14—C13	1.3 (4)
O1—C7—C8—C9	−177.3 (2)	C5—C6—C1—C2	2.3 (3)
N1—C7—C8—C9	1.4 (2)	N1—C6—C1—C2	−176.6 (2)
C7—N1—C6—C5	−32.3 (3)	C6—C1—C2—C3	−1.3 (4)
N2—N1—C6—C5	163.56 (19)	C6—C5—C4—C3	0.3 (4)
C7—N1—C6—C1	146.5 (2)	C1—C2—C3—C4	−0.2 (5)
N2—N1—C6—C1	−17.5 (3)	C5—C4—C3—C2	0.7 (5)
C13—C12—C17—C16	1.0 (3)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.86	2.00	2.722 (2)	140

Experimental details

Crystal data
Chemical formula	C₃₈H₃₇N₇O₂
M_r	623.75
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	20.3219 (8), 8.1990 (2), 20.5468 (6)
β (°)	106.748 (2)
V (Å³)	3278.27 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.23 × 0.21 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.982, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	8269, 3765, 1886
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.655

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.179, 1.01
No. of reflections	3765
No. of parameters	214
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.29

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.86	2.00	2.722 (2)	140.3

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China for financial support (grant No. 21001040).

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, H.-W. (2010). Acta Cryst. E66, o1534. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, Y. & Yang, Z.-Y. (2005). Transition Met. Chem. 30, 902–906. Web of Science CrossRef CAS Google Scholar
Yang, Z.-Y., Yang, R.-D., Li, F.-S. & Yu, K.-B. (2000). Polyhedron, 19, 2599–2604. Web of Science CSD CrossRef CAS Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E,E)-3,3′-Di­methyl-1,1′-di­phenyl-4,4′-{[3-aza­pentane-1,5-diylbis(aza­nedi­yl)]bis­­(phenyl­methyl­­idyne)}di-1H-pyrazol-5(4H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E,E)-3,3′-Dimethyl-1,1′-diphenyl-4,4′-{[3-azapentane-1,5-diylbis(azanediyl)]bis(phenylmethylidyne)}di-1H-pyrazol-5(4H)-one