Literature DB >> 21581714

N,N-Bis(2-hydroxy-benzyl-idene)-2,2'-bipyridyl-3,3'-dicarbohydrazide.

Shao-Bin Miao1, Lu-Lu Zang, Ya-Wei Fan, Bao-Ming Ji.   

Abstract

In the title compound, C(26)H(20)N(6)O(4), the two aroylhydrazone side groups exist as diastereomeres, both in the keto form in the crystal structure. The aroylhydrazone units support the mol-ecular conformation through an intra-molecular N-H⋯O hydrogen bond. Two mol-ecules are connected into a centrosymmetric dimer by inter-molecular N-H⋯N hydrogen bonds. These dimers are connected into chains along the a axis by inter-molecular O-H⋯O hydrogen bonds. The combination of these hydrogen bonds results in layers in the bc plane. The layers are further linked by weak C-H⋯π contacts to form a three-dimensional network structure.

Entities:  

Year:  2008        PMID: 21581714      PMCID: PMC2967985          DOI: 10.1107/S1600536808038087

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For syntheses, structures and ligand conformations of AgI complexes with flexible N,N′-di(2-pyrid­yl)adipoamide ligands, see: Chen et al. (2007 ▶). For palladium-catalysed allylic alkyl­ation using chiral hydrazones as ligands, see: Mino et al. (2001 ▶). For the biological activity of hydrazones and their metal complexes, see: Rodriguez-Argüelles et al. (2004 ▶); Wiley & Clevenger (1962 ▶). For coordinated hydrazone ligands as nucleophiles, see: Wood et al. (2004 ▶). For a new fluorescent rhodamine hydrazone chemosensor for CuII, see: Xiang et al. (2006 ▶).

Experimental

Crystal data

C26H20N6O4 M = 480.48 Triclinic, a = 9.4251 (13) Å b = 11.7642 (16) Å c = 12.0384 (16) Å α = 98.842 (2)° β = 108.895 (2)° γ = 104.591 (2)° V = 1181.1 (3) Å3 Z = 2 Mo Kα radiation μ = 0.10 mm−1 T = 293 (2) K 0.37 × 0.25 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.956, T max = 0.991 8593 measured reflections 4281 independent reflections 3119 reflections with I > 2σ(I) R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.111 S = 1.02 4281 reflections 327 parameters H-atom parameters constrained Δρmax = 0.46 e Å−3 Δρmin = −0.19 e Å−3 Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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 and PLATON (Spek, 2003 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038087/si2129sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038087/si2129Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C26H20N6O4Z = 2
Mr = 480.48F(000) = 500
Triclinic, P1Dx = 1.351 Mg m3
a = 9.4251 (13) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.7642 (16) ÅCell parameters from 2245 reflections
c = 12.0384 (16) Åθ = 2.4–23.8°
α = 98.842 (2)°µ = 0.10 mm1
β = 108.895 (2)°T = 293 K
γ = 104.591 (2)°Block, yellow
V = 1181.1 (3) Å30.37 × 0.25 × 0.10 mm
Bruker SMART CCD area-detector diffractometer4281 independent reflections
Radiation source: fine-focus sealed tube3119 reflections with I > 2σ(I)
graphiteRint = 0.021
φ and ω scansθmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.956, Tmax = 0.991k = −14→14
8593 measured reflectionsl = −14→14
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0497P)2 + 0.2276P] where P = (Fo2 + 2Fc2)/3
4281 reflections(Δ/σ)max < 0.001
327 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = −0.19 e Å3
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.
xyzUiso*/Ueq
O10.91934 (18)0.72851 (13)0.61871 (15)0.0628 (4)
H10.86140.75510.57020.094*
O20.54744 (16)0.76483 (12)0.33652 (13)0.0531 (4)
O30.03313 (14)0.63641 (12)0.00365 (11)0.0452 (3)
O40.76743 (15)0.68107 (15)0.01770 (12)0.0586 (4)
H40.85190.67490.01700.088*
N10.81685 (17)0.90089 (14)0.53315 (14)0.0400 (4)
N20.70967 (17)0.94879 (14)0.46351 (13)0.0399 (4)
H2D0.72801.02610.47950.048*
N30.20060 (19)0.93570 (15)0.21026 (14)0.0458 (4)
N40.23711 (19)0.79268 (14)0.42134 (13)0.0413 (4)
N50.29163 (16)0.65006 (13)0.09343 (13)0.0370 (4)
H5D0.36930.66300.16090.044*
N60.31480 (17)0.62971 (13)−0.01446 (13)0.0355 (4)
C11.0361 (2)0.82252 (18)0.70788 (18)0.0448 (5)
C21.1409 (3)0.7965 (2)0.8036 (2)0.0579 (6)
H21.13100.71600.80460.070*
C31.2592 (3)0.8884 (2)0.8969 (2)0.0645 (7)
H31.32740.86940.96120.077*
C41.2783 (3)1.0079 (2)0.8970 (2)0.0607 (6)
H4A1.36011.06950.95980.073*
C51.1754 (2)1.03568 (19)0.80321 (18)0.0488 (5)
H51.18731.11670.80380.059*
C61.0531 (2)0.94455 (17)0.70696 (16)0.0383 (4)
C70.9401 (2)0.97971 (17)0.61685 (16)0.0385 (4)
H70.95751.06170.61990.046*
C80.5773 (2)0.87486 (17)0.37108 (16)0.0375 (4)
C90.4686 (2)0.93978 (16)0.31156 (15)0.0348 (4)
C100.5244 (2)1.05037 (17)0.28697 (17)0.0423 (5)
H100.63281.08890.31180.051*
C110.4186 (3)1.10226 (19)0.22581 (19)0.0509 (5)
H110.45411.17730.21070.061*
C120.2594 (3)1.04164 (19)0.18726 (19)0.0518 (5)
H120.18851.07590.14280.062*
C130.3044 (2)0.88770 (16)0.27334 (15)0.0340 (4)
C140.22940 (19)0.77607 (16)0.30632 (15)0.0332 (4)
C150.1631 (2)0.69644 (19)0.45134 (18)0.0488 (5)
H150.17020.70590.53130.059*
C160.0775 (2)0.58480 (19)0.37127 (18)0.0514 (5)
H160.02740.52080.39640.062*
C170.0671 (2)0.56921 (18)0.25305 (18)0.0459 (5)
H170.00750.49500.19630.055*
C180.14672 (19)0.66555 (16)0.21967 (15)0.0334 (4)
C190.1497 (2)0.65002 (15)0.09467 (16)0.0333 (4)
C200.4561 (2)0.63447 (16)−0.00311 (16)0.0359 (4)
H200.53420.65310.07400.043*
C210.4959 (2)0.61090 (16)−0.11018 (16)0.0358 (4)
C220.3798 (2)0.5622 (2)−0.22627 (19)0.0532 (5)
H220.27380.5441−0.23630.064*
C230.4176 (3)0.5402 (2)−0.3266 (2)0.0697 (7)
H230.33810.5068−0.40360.084*
C240.5753 (3)0.5682 (2)−0.3121 (2)0.0662 (7)
H240.60170.5546−0.37980.079*
C250.6928 (2)0.6157 (2)−0.1985 (2)0.0522 (5)
H250.79850.6345−0.18970.063*
C260.6548 (2)0.63589 (16)−0.09660 (17)0.0385 (4)
U11U22U33U12U13U23
O10.0565 (10)0.0435 (9)0.0758 (11)0.0107 (7)0.0136 (8)0.0147 (8)
O20.0472 (8)0.0374 (8)0.0581 (9)0.0142 (6)0.0026 (7)0.0033 (7)
O30.0298 (7)0.0663 (9)0.0356 (7)0.0159 (6)0.0098 (6)0.0071 (6)
O40.0326 (7)0.0918 (12)0.0490 (9)0.0242 (8)0.0154 (7)0.0044 (8)
N10.0359 (9)0.0441 (9)0.0378 (9)0.0142 (7)0.0103 (7)0.0102 (7)
N20.0383 (9)0.0361 (8)0.0381 (9)0.0111 (7)0.0074 (7)0.0068 (7)
N30.0452 (9)0.0520 (10)0.0467 (10)0.0221 (8)0.0181 (8)0.0186 (8)
N40.0500 (10)0.0399 (9)0.0317 (8)0.0123 (7)0.0153 (7)0.0064 (7)
N50.0292 (8)0.0504 (9)0.0291 (8)0.0124 (7)0.0101 (6)0.0065 (7)
N60.0335 (8)0.0437 (9)0.0326 (8)0.0135 (7)0.0161 (7)0.0095 (7)
C10.0385 (11)0.0479 (12)0.0504 (12)0.0120 (9)0.0201 (10)0.0154 (10)
C20.0535 (13)0.0611 (14)0.0708 (15)0.0250 (12)0.0247 (12)0.0357 (13)
C30.0524 (14)0.0918 (19)0.0571 (15)0.0310 (14)0.0166 (12)0.0371 (14)
C40.0484 (13)0.0759 (17)0.0448 (13)0.0172 (12)0.0056 (10)0.0110 (12)
C50.0435 (11)0.0510 (12)0.0456 (12)0.0153 (10)0.0109 (10)0.0081 (10)
C60.0333 (10)0.0468 (11)0.0373 (10)0.0147 (8)0.0151 (8)0.0114 (9)
C70.0376 (10)0.0400 (10)0.0377 (10)0.0116 (9)0.0152 (9)0.0086 (9)
C80.0348 (10)0.0388 (11)0.0364 (10)0.0099 (8)0.0130 (8)0.0066 (9)
C90.0375 (10)0.0352 (10)0.0293 (9)0.0102 (8)0.0122 (8)0.0055 (8)
C100.0417 (11)0.0403 (11)0.0392 (11)0.0068 (9)0.0136 (9)0.0091 (9)
C110.0616 (14)0.0428 (11)0.0529 (13)0.0168 (10)0.0239 (11)0.0208 (10)
C120.0580 (14)0.0552 (13)0.0560 (13)0.0299 (11)0.0241 (11)0.0279 (11)
C130.0376 (10)0.0346 (9)0.0303 (9)0.0135 (8)0.0137 (8)0.0049 (8)
C140.0284 (9)0.0380 (10)0.0325 (10)0.0119 (8)0.0105 (8)0.0075 (8)
C150.0593 (13)0.0515 (12)0.0343 (11)0.0107 (10)0.0214 (10)0.0114 (10)
C160.0588 (13)0.0451 (12)0.0437 (12)−0.0009 (10)0.0259 (10)0.0083 (10)
C170.0441 (11)0.0420 (11)0.0416 (11)−0.0001 (9)0.0187 (9)0.0008 (9)
C180.0278 (9)0.0383 (10)0.0328 (10)0.0097 (8)0.0125 (8)0.0050 (8)
C190.0290 (9)0.0350 (9)0.0329 (10)0.0078 (7)0.0118 (8)0.0042 (8)
C200.0317 (10)0.0380 (10)0.0393 (10)0.0133 (8)0.0133 (8)0.0103 (8)
C210.0352 (10)0.0385 (10)0.0405 (10)0.0172 (8)0.0180 (8)0.0121 (8)
C220.0364 (11)0.0719 (15)0.0470 (12)0.0183 (10)0.0143 (10)0.0058 (11)
C230.0567 (14)0.107 (2)0.0413 (13)0.0328 (14)0.0159 (11)0.0042 (13)
C240.0662 (16)0.102 (2)0.0461 (13)0.0416 (14)0.0315 (12)0.0171 (13)
C250.0450 (12)0.0731 (15)0.0542 (13)0.0296 (11)0.0289 (11)0.0208 (11)
C260.0369 (10)0.0415 (10)0.0422 (11)0.0184 (8)0.0170 (9)0.0108 (9)
O1—C11.358 (2)C8—C91.494 (2)
O1—H10.8200C9—C101.390 (2)
O2—C81.226 (2)C9—C131.398 (2)
O3—C191.229 (2)C10—C111.371 (3)
O4—C261.359 (2)C10—H100.9300
O4—H40.8200C11—C121.372 (3)
N1—C71.279 (2)C11—H110.9300
N1—N21.387 (2)C12—H120.9300
N2—C81.345 (2)C13—C141.502 (2)
N2—H2D0.8600C14—C181.390 (2)
N3—C131.335 (2)C15—C161.371 (3)
N3—C121.340 (2)C15—H150.9300
N4—C151.338 (2)C16—C171.374 (3)
N4—C141.344 (2)C16—H160.9300
N5—C191.343 (2)C17—C181.384 (2)
N5—N61.3807 (19)C17—H170.9300
N5—H5D0.8600C18—C191.498 (2)
N6—C201.280 (2)C20—C211.461 (2)
C1—C21.386 (3)C20—H200.9300
C1—C61.406 (3)C21—C221.388 (3)
C2—C31.372 (3)C21—C261.401 (2)
C2—H20.9300C22—C231.372 (3)
C3—C41.371 (3)C22—H220.9300
C3—H30.9300C23—C241.383 (3)
C4—C51.373 (3)C23—H230.9300
C4—H4A0.9300C24—C251.372 (3)
C5—C61.397 (3)C24—H240.9300
C5—H50.9300C25—C261.388 (3)
C6—C71.447 (2)C25—H250.9300
C7—H70.9300
C1—O1—H1109.5N3—C12—C11123.45 (19)
C26—O4—H4109.5N3—C12—H12118.3
C7—N1—N2114.91 (16)C11—C12—H12118.3
C8—N2—N1120.29 (15)N3—C13—C9123.44 (16)
C8—N2—H2D119.9N3—C13—C14113.82 (15)
N1—N2—H2D119.9C9—C13—C14122.65 (15)
C13—N3—C12117.24 (17)N4—C14—C18122.77 (16)
C15—N4—C14117.06 (16)N4—C14—C13115.72 (15)
C19—N5—N6121.03 (14)C18—C14—C13121.31 (15)
C19—N5—H5D119.5N4—C15—C16123.90 (18)
N6—N5—H5D119.5N4—C15—H15118.1
C20—N6—N5114.90 (14)C16—C15—H15118.1
O1—C1—C2118.42 (19)C15—C16—C17118.71 (18)
O1—C1—C6122.38 (17)C15—C16—H16120.6
C2—C1—C6119.20 (19)C17—C16—H16120.6
C3—C2—C1120.6 (2)C16—C17—C18119.02 (18)
C3—C2—H2119.7C16—C17—H17120.5
C1—C2—H2119.7C18—C17—H17120.5
C4—C3—C2121.0 (2)C17—C18—C14118.48 (16)
C4—C3—H3119.5C17—C18—C19120.92 (16)
C2—C3—H3119.5C14—C18—C19120.56 (15)
C3—C4—C5119.4 (2)O3—C19—N5124.31 (16)
C3—C4—H4A120.3O3—C19—C18123.07 (15)
C5—C4—H4A120.3N5—C19—C18112.61 (15)
C4—C5—C6121.3 (2)N6—C20—C21120.59 (16)
C4—C5—H5119.4N6—C20—H20119.7
C6—C5—H5119.4C21—C20—H20119.7
C5—C6—C1118.61 (17)C22—C21—C26118.43 (17)
C5—C6—C7118.48 (18)C22—C21—C20121.77 (16)
C1—C6—C7122.62 (17)C26—C21—C20119.79 (16)
N1—C7—C6121.70 (18)C23—C22—C21121.58 (19)
N1—C7—H7119.2C23—C22—H22119.2
C6—C7—H7119.2C21—C22—H22119.2
O2—C8—N2124.11 (17)C22—C23—C24119.3 (2)
O2—C8—C9122.32 (16)C22—C23—H23120.3
N2—C8—C9113.56 (16)C24—C23—H23120.3
C10—C9—C13117.33 (16)C25—C24—C23120.5 (2)
C10—C9—C8122.09 (17)C25—C24—H24119.7
C13—C9—C8120.52 (16)C23—C24—H24119.7
C11—C10—C9119.50 (18)C24—C25—C26120.28 (19)
C11—C10—H10120.3C24—C25—H25119.9
C9—C10—H10120.3C26—C25—H25119.9
C10—C11—C12118.93 (18)O4—C26—C25122.21 (17)
C10—C11—H11120.5O4—C26—C21117.96 (16)
C12—C11—H11120.5C25—C26—C21119.82 (18)
C7—N1—N2—C8178.55 (16)C15—N4—C14—C13176.13 (16)
C19—N5—N6—C20178.69 (16)N3—C13—C14—N4−101.74 (18)
O1—C1—C2—C3−178.8 (2)C9—C13—C14—N474.8 (2)
C6—C1—C2—C30.5 (3)N3—C13—C14—C1873.3 (2)
C1—C2—C3—C4−1.1 (4)C9—C13—C14—C18−110.1 (2)
C2—C3—C4—C51.3 (4)C14—N4—C15—C16−2.0 (3)
C3—C4—C5—C6−1.0 (3)N4—C15—C16—C170.6 (3)
C4—C5—C6—C10.4 (3)C15—C16—C17—C181.7 (3)
C4—C5—C6—C7174.46 (19)C16—C17—C18—C14−2.4 (3)
O1—C1—C6—C5179.16 (18)C16—C17—C18—C19175.03 (17)
C2—C1—C6—C5−0.1 (3)N4—C14—C18—C171.0 (3)
O1—C1—C6—C75.3 (3)C13—C14—C18—C17−173.68 (16)
C2—C1—C6—C7−173.96 (18)N4—C14—C18—C19−176.47 (16)
N2—N1—C7—C6171.98 (15)C13—C14—C18—C198.9 (2)
C5—C6—C7—N1−173.13 (17)N6—N5—C19—O3−2.5 (3)
C1—C6—C7—N10.7 (3)N6—N5—C19—C18176.19 (14)
N1—N2—C8—O2−5.5 (3)C17—C18—C19—O371.2 (2)
N1—N2—C8—C9175.49 (14)C14—C18—C19—O3−111.4 (2)
O2—C8—C9—C10−137.05 (19)C17—C18—C19—N5−107.46 (19)
N2—C8—C9—C1042.0 (2)C14—C18—C19—N569.9 (2)
O2—C8—C9—C1340.0 (3)N5—N6—C20—C21178.09 (14)
N2—C8—C9—C13−140.91 (17)N6—C20—C21—C22−11.5 (3)
C13—C9—C10—C11−1.0 (3)N6—C20—C21—C26169.45 (17)
C8—C9—C10—C11176.21 (17)C26—C21—C22—C23−1.0 (3)
C9—C10—C11—C12−1.8 (3)C20—C21—C22—C23−180.0 (2)
C13—N3—C12—C11−0.5 (3)C21—C22—C23—C24−0.6 (4)
C10—C11—C12—N32.7 (3)C22—C23—C24—C251.0 (4)
C12—N3—C13—C9−2.6 (3)C23—C24—C25—C260.3 (4)
C12—N3—C13—C14173.98 (16)C24—C25—C26—O4179.0 (2)
C10—C9—C13—N33.3 (3)C24—C25—C26—C21−1.9 (3)
C8—C9—C13—N3−173.91 (16)C22—C21—C26—O4−178.60 (18)
C10—C9—C13—C14−172.94 (16)C20—C21—C26—O40.4 (3)
C8—C9—C13—C149.8 (3)C22—C21—C26—C252.2 (3)
C15—N4—C14—C181.2 (3)C20—C21—C26—C25−178.76 (17)
D—H···AD—HH···AD···AD—H···A
N5—H5D···O20.862.152.962 (2)157
N2—H2D···N4i0.862.172.985 (2)159
O4—H4···O3ii0.821.922.736 (2)172
O1—H1···N10.821.952.663 (2)145
C10—H10···Cg3iii0.932.763.458 (2)133
C11—H11···Cg4iv0.932.733.588 (2)154
Table 1

Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the benzene rings C1–C6 and C21–C26, respectively.

D—H⋯AD—HH⋯ADAD—H⋯A
N5—H5D⋯O20.862.152.962 (2)157
N2—H2D⋯N4i0.862.172.985 (2)159
O4—H4⋯O3ii0.821.922.736 (2)172
O1—H1⋯N10.821.952.663 (2)145
C10—H10⋯Cg3iii0.932.763.458 (2)133
C11—H11⋯Cg4iv0.932.733.588 (2)154

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

  6 in total

1.  ALDEHYDE HYDRAZONE DERIVATIVES IN CANCER CHEMOTHERAPY.

Authors:  R H WILEY; R L CLEVENGER
Journal:  J Med Pharm Chem       Date:  1962-11

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  New fluorescent rhodamine hydrazone chemosensor for Cu(II) with high selectivity and sensitivity.

Authors:  Yu Xiang; Aijun Tong; Peiyuan Jin; Yong Ju
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

4.  Palladium-catalyzed allylic alkylation using chiral hydrazones as ligands.

Authors:  T Mino; M Shiotsuki; N Yamamoto; T Suenaga; M Sakamoto; T Fujita; M Yamashita
Journal:  J Org Chem       Date:  2001-03-09       Impact factor: 4.354

5.  Coordinated hydrazone ligands as nucleophiles: reactions of Fe(papy)2.

Authors:  Aaron Wood; Wasim Aris; David J R Brook
Journal:  Inorg Chem       Date:  2004-12-27       Impact factor: 5.165

6.  Synthesis, characterization and biological activity of Ni, Cu and Zn complexes of isatin hydrazones.

Authors:  Maria C Rodríuez-Argüelles; Marisa Belicchi errari; Franco Bisceglie; Corrado Pelizzi; Giorgio Pelosi; Silvana Pinelli; Monica Sassi
Journal:  J Inorg Biochem       Date:  2004-02       Impact factor: 4.155

  6 in total

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