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Acta Crystallogr Sect E Struct Rep Online. Dec 1, 2010; 66(Pt 12): o3326.
Published online Nov 27, 2010. doi:  10.1107/S1600536810048981
PMCID: PMC3011678
(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 Lia
aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo 454000, People’s Republic of China
bInstitute of Functional Materials, Jiangxi University of Finance & Economics, Nanchang 330013, People’s Republic of China
Correspondence e-mail: wangyuan08/at/hpu.edu.cn
Received November 21, 2010; Accepted November 23, 2010.
Abstract
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 [triangle]); Wang & Yang (2005 [triangle]). 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 [triangle]).
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Object name is e-66-o3326-scheme1.jpg Object name is e-66-o3326-scheme1.jpg
Crystal data
  • C38H37N7O2
  • M r = 623.75
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3326-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.179
  • S = 1.01
  • 3765 reflections
  • 214 parameters
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.29 e Å−3
Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810048981/cv5005sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048981/cv5005Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors are grateful to the National Natural Science Foundation of China for financial support (grant No. 21001040).
supplementary crystallographic information
Comment
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.
Experimental
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.
Refinement
All H atoms were placed in calculated positions, with C—H = 0.93–0.97 Å and N—H = 0.86 Å, and were treated as riding, with Uiso(H) = 1.2-1.5 Ueq of the parent atom.
Figures
Fig. 1.
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).
Crystal data
C38H37N7O2F(000) = 1320
Mr = 623.75Dx = 1.264 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 20.3219 (8) ÅCell parameters from 1721 reflections
b = 8.1990 (2) Åθ = 2.5–22.0°
c = 20.5468 (6) ŵ = 0.08 mm1
β = 106.748 (2)°T = 296 K
V = 3278.27 (18) Å3Block, yellow
Z = 40.23 × 0.21 × 0.15 mm
Data collection
Bruker SMART APEXII CCD diffractometer3765 independent reflections
Radiation source: fine-focus sealed tube1886 reflections with I > 2σ(I)
graphiteRint = 0.021
phi and ω scansθmax = 27.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −26→20
Tmin = 0.982, Tmax = 0.988k = −8→10
8269 measured reflectionsl = −26→25
Refinement
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0884P)2 + 0.1149P] where P = (Fo2 + 2Fc2)/3
3765 reflections(Δ/σ)max < 0.001
214 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = −0.29 e Å3
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 > 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)
xyzUiso*/Ueq
O10.06573 (8)0.23883 (18)0.35444 (8)0.0809 (5)
N10.14838 (9)0.0606 (2)0.41990 (8)0.0707 (5)
C70.12657 (11)0.1980 (3)0.38051 (10)0.0645 (6)
C120.25215 (10)0.4844 (3)0.32781 (11)0.0661 (6)
N20.21985 (10)0.0439 (3)0.43823 (10)0.0819 (6)
N30.12874 (9)0.4629 (2)0.29494 (10)0.0833 (6)
H3A0.09270.41450.29920.100*
C110.18821 (10)0.4066 (3)0.33364 (11)0.0657 (6)
N40.00000.6106 (3)0.25000.0898 (9)
H40.00000.50570.25000.108*
C80.18835 (10)0.2749 (3)0.37639 (10)0.0635 (6)
C60.10856 (13)−0.0732 (3)0.42954 (10)0.0719 (6)
C170.27276 (12)0.4657 (3)0.27000 (11)0.0738 (6)
H170.24560.40700.23330.089*
C90.24330 (11)0.1713 (3)0.41344 (10)0.0715 (6)
C190.06028 (11)0.7026 (3)0.25289 (12)0.0802 (7)
H19A0.07490.76080.29580.096*
H19B0.05000.78250.21650.096*
C150.37336 (13)0.6229 (3)0.32006 (17)0.0930 (8)
H150.41440.66850.31740.112*
C130.29269 (12)0.5747 (3)0.38196 (12)0.0822 (7)
H130.27910.58760.42120.099*
C160.33348 (14)0.5339 (3)0.26650 (14)0.0840 (7)
H160.34760.51960.22770.101*
C50.04144 (14)−0.0517 (3)0.42877 (12)0.0830 (7)
H50.02240.05240.42390.100*
C180.11649 (12)0.5955 (3)0.24635 (13)0.0913 (8)
H18A0.10480.55110.20070.110*
H18B0.15820.65920.25350.110*
C140.35261 (13)0.6447 (3)0.37766 (15)0.0951 (8)
H140.37920.70680.41360.114*
C100.31871 (12)0.1867 (4)0.42487 (13)0.0961 (8)
H10A0.34120.09050.44720.144*
H10B0.33540.28030.45280.144*
H10C0.32810.19910.38200.144*
C10.13730 (17)−0.2275 (3)0.43868 (12)0.0930 (8)
H10.1832−0.24280.44090.112*
C20.0968 (2)−0.3578 (4)0.44439 (14)0.1196 (12)
H20.1156−0.46210.44960.144*
C40.00213 (17)−0.1842 (4)0.43516 (14)0.1080 (9)
H4A−0.0435−0.16920.43440.130*
C30.0297 (3)−0.3380 (5)0.44262 (15)0.1220 (12)
H30.0030−0.42760.44640.146*
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
O10.0582 (10)0.0849 (11)0.0935 (11)0.0105 (8)0.0123 (8)0.0203 (9)
N10.0691 (12)0.0775 (12)0.0639 (11)0.0186 (10)0.0165 (9)0.0105 (10)
C70.0633 (14)0.0714 (13)0.0550 (11)0.0118 (11)0.0113 (10)0.0031 (11)
C120.0527 (12)0.0789 (14)0.0630 (13)0.0104 (10)0.0106 (10)0.0064 (11)
N20.0710 (13)0.1030 (15)0.0698 (12)0.0299 (11)0.0171 (9)0.0151 (11)
N30.0534 (11)0.0994 (14)0.0904 (14)0.0020 (10)0.0098 (9)0.0312 (12)
C110.0534 (12)0.0782 (14)0.0613 (12)0.0071 (11)0.0099 (9)−0.0004 (11)
N40.0586 (17)0.0646 (15)0.141 (3)0.0000.0209 (16)0.000
C80.0578 (13)0.0768 (14)0.0529 (11)0.0114 (11)0.0109 (9)0.0040 (11)
C60.0888 (17)0.0736 (15)0.0502 (11)0.0087 (13)0.0153 (11)0.0050 (11)
C170.0676 (15)0.0905 (16)0.0623 (13)0.0129 (12)0.0171 (11)0.0103 (12)
C90.0635 (14)0.0937 (16)0.0556 (12)0.0222 (13)0.0144 (10)0.0047 (12)
C190.0640 (15)0.0849 (15)0.0790 (15)−0.0046 (13)0.0001 (11)0.0105 (13)
C150.0587 (15)0.0976 (19)0.118 (2)0.0060 (14)0.0185 (15)0.0314 (18)
C130.0626 (14)0.1095 (18)0.0691 (14)0.0038 (14)0.0101 (11)−0.0065 (14)
C160.0793 (18)0.0950 (17)0.0848 (17)0.0241 (14)0.0348 (14)0.0294 (15)
C50.0876 (18)0.0819 (16)0.0771 (15)−0.0009 (14)0.0201 (13)0.0111 (13)
C180.0667 (15)0.1080 (18)0.0938 (17)0.0109 (14)0.0146 (12)0.0381 (15)
C140.0646 (17)0.110 (2)0.101 (2)−0.0025 (14)0.0075 (14)−0.0023 (16)
C100.0650 (16)0.134 (2)0.0863 (16)0.0318 (15)0.0163 (12)0.0204 (16)
C10.136 (2)0.0787 (17)0.0666 (14)0.0274 (17)0.0325 (15)0.0120 (13)
C20.205 (4)0.074 (2)0.0774 (19)0.014 (2)0.037 (2)0.0158 (15)
C40.119 (2)0.105 (2)0.0920 (19)−0.020 (2)0.0188 (16)0.0229 (17)
C30.182 (4)0.100 (3)0.0778 (18)−0.037 (3)0.026 (2)0.0155 (17)
Geometric parameters (Å, °)
O1—C71.243 (2)C19—H19A0.9700
N1—C71.383 (3)C19—H19B0.9700
N1—N21.398 (2)C15—C161.374 (4)
N1—C61.411 (3)C15—C141.378 (4)
C7—C81.429 (3)C15—H150.9300
C12—C171.377 (3)C13—C141.372 (3)
C12—C131.391 (3)C13—H130.9300
C12—C111.483 (3)C16—H160.9300
N2—C91.310 (3)C5—C41.377 (4)
N3—C111.324 (3)C5—H50.9300
N3—C181.448 (3)C18—H18A0.9700
N3—H3A0.8600C18—H18B0.9700
C11—C81.392 (3)C14—H140.9300
N4—C191.425 (3)C10—H10A0.9600
N4—C19i1.425 (3)C10—H10B0.9600
N4—H40.8600C10—H10C0.9600
C8—C91.435 (3)C1—C21.375 (4)
C6—C51.371 (3)C1—H10.9300
C6—C11.384 (3)C2—C31.362 (5)
C17—C161.375 (3)C2—H20.9300
C17—H170.9300C4—C31.370 (5)
C9—C101.487 (3)C4—H4A0.9300
C19—C181.477 (3)C3—H30.9300
C7—N1—N2111.73 (18)C16—C15—H15120.0
C7—N1—C6127.98 (19)C14—C15—H15120.0
N2—N1—C6118.64 (18)C14—C13—C12120.2 (2)
O1—C7—N1125.6 (2)C14—C13—H13119.9
O1—C7—C8129.6 (2)C12—C13—H13119.9
N1—C7—C8104.77 (18)C15—C16—C17120.3 (2)
C17—C12—C13119.5 (2)C15—C16—H16119.8
C17—C12—C11120.9 (2)C17—C16—H16119.8
C13—C12—C11119.66 (19)C6—C5—C4120.0 (3)
C9—N2—N1106.44 (17)C6—C5—H5120.0
C11—N3—C18128.4 (2)C4—C5—H5120.0
C11—N3—H3A115.8N3—C18—C19111.5 (2)
C18—N3—H3A115.8N3—C18—H18A109.3
N3—C11—C8119.03 (19)C19—C18—H18A109.3
N3—C11—C12118.1 (2)N3—C18—H18B109.3
C8—C11—C12122.84 (18)C19—C18—H18B109.3
C19—N4—C19i116.1 (3)H18A—C18—H18B108.0
C19—N4—H4122.0C13—C14—C15119.9 (3)
C19i—N4—H4122.0C13—C14—H14120.1
C11—C8—C7122.52 (18)C15—C14—H14120.1
C11—C8—C9130.9 (2)C9—C10—H10A109.5
C7—C8—C9105.7 (2)C9—C10—H10B109.5
C5—C6—C1119.9 (2)H10A—C10—H10B109.5
C5—C6—N1120.5 (2)C9—C10—H10C109.5
C1—C6—N1119.6 (2)H10A—C10—H10C109.5
C16—C17—C12120.0 (2)H10B—C10—H10C109.5
C16—C17—H17120.0C2—C1—C6118.8 (3)
C12—C17—H17120.0C2—C1—H1120.6
N2—C9—C8111.3 (2)C6—C1—H1120.6
N2—C9—C10118.7 (2)C3—C2—C1121.6 (3)
C8—C9—C10130.0 (2)C3—C2—H2119.2
N4—C19—C18111.1 (2)C1—C2—H2119.2
N4—C19—H19A109.4C3—C4—C5120.4 (3)
C18—C19—H19A109.4C3—C4—H4A119.8
N4—C19—H19B109.4C5—C4—H4A119.8
C18—C19—H19B109.4C2—C3—C4119.1 (3)
H19A—C19—H19B108.0C2—C3—H3120.4
C16—C15—C14120.1 (2)C4—C3—H3120.4
N2—N1—C7—O1176.4 (2)C11—C12—C17—C16−177.64 (19)
C6—N1—C7—O111.4 (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—C92.5 (2)C7—C8—C9—N20.0 (2)
C6—N1—N2—C9169.01 (18)C11—C8—C9—C109.3 (4)
C18—N3—C11—C8−178.9 (2)C7—C8—C9—C10178.1 (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—C140.1 (4)
C13—C12—C11—N3112.2 (2)C11—C12—C13—C14178.8 (2)
C17—C12—C11—C8108.9 (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—C4177.1 (2)
N3—C11—C8—C9166.9 (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—C11171.45 (18)C16—C15—C14—C131.3 (4)
O1—C7—C8—C9−177.3 (2)C5—C6—C1—C22.3 (3)
N1—C7—C8—C91.4 (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—C5163.56 (19)C6—C5—C4—C30.3 (4)
C7—N1—C6—C1146.5 (2)C1—C2—C3—C4−0.2 (5)
N2—N1—C6—C1−17.5 (3)C5—C4—C3—C20.7 (5)
C13—C12—C17—C161.0 (3)
Symmetry codes: (i) −x, y, −z+1/2.
Hydrogen-bond geometry (Å, °)
D—H···AD—HH···AD···AD—H···A
N3—H3A···O10.862.002.722 (2)140
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5005).
References
  • Bruker (2007). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, H.-W. (2010). Acta Cryst. E66, o1534. [PMC free article] [PubMed]
  • Wang, Y. & Yang, Z.-Y. (2005). Transition Met. Chem.30, 902–906.
  • Yang, Z.-Y., Yang, R.-D., Li, F.-S. & Yu, K.-B. (2000). Polyhedron, 19, 2599–2604.
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