Literature DB >> 21582924

2,2'-[(E,E)-1,1'-(2,2-Dimethyl-propane-1,3-diyldinitrilo)diethyl-idyne]diphenol.

Morteza Montazerozohori, Mohammad Hossein Habibi, Ahmad Hojjati, Reza Mokhtari, Yuki Yamane, Takayoshi Suzuki.   

Abstract

The title Schiff base, C(21)H(26)N(2)O(2), contains two intra-molecular O-H⋯N hydrogen bonds between the hydroxyl groups and the nearest imine N atoms, each leading to a six-membered ring. Weak C-H⋯O hydrogen bonds result in a ladder network running along the a axis. In addition, inter-molecular C-H⋯π inter-actions serve to stabilize the extended structure.

Entities:  

Year:  2009        PMID： 21582924      PMCID： PMC2969254          DOI： 10.1107/S1600536809022855

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


Related literature

For the biological activity of Schiff bases, see: Singh & Dash (1988 ▶); More et al. (2001 ▶); Baseer et al. (2000 ▶); El-Masry et al. (2000 ▶); Kabeer et al. (2001 ▶); Kuzmin et al. (2000 ▶); Desai et al. (2001 ▶). For n class="Chemical">metal complexes of Schiff bases, see: Habibi et al. (2007a ▶). For related structures, see: Barati et al. (2009 ▶); Habibi et al. (2007b ▶,c ▶).

Experimental

Crystal data

C21H26N2O2 M = 338.44 Triclinic, a = 7.7847 (9) Å b = 9.1857 (12) Å c = 13.3801 (14) Å α = 79.547 (4)° β = 77.508 (3)° γ = 85.537 (4)° V = 917.89 (18) Å3 Z = 2 Mo Kα radiation μ = 0.08 mm−1 T = 193 K 0.40 × 0.30 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.969, T max = 0.992 9076 measured reflections 4143 independent reflections 3022 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.135 S = 1.05 4143 reflections 331 parameters All H-atom parameters refined Δρmax = 0.28 e Å−3 Δρmin = −0.17 e Å−3 Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022855/fj2213sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022855/fj2213Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C21H26N2O2Z = 2
Mr = 338.44F(000) = 364
Triclinic, P1Dx = 1.225 Mg m−3
a = 7.7847 (9) ÅMo Kα radiation, λ = 0.71075 Å
b = 9.1857 (12) ÅCell parameters from 6952 reflections
c = 13.3801 (14) Åθ = 3.2–27.5°
α = 79.547 (4)°µ = 0.08 mm−1
β = 77.508 (3)°T = 193 K
γ = 85.537 (4)°Block, yellow
V = 917.89 (18) Å30.40 × 0.30 × 0.10 mm
Rigaku R-AXIS RAPID diffractometer4143 independent reflections
Radiation source: fine-focus sealed tube3022 reflections with I > 2σ(I)
graphiteRint = 0.023
Detector resolution: 10.00 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = −9→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −11→11
Tmin = 0.969, Tmax = 0.992l = −17→17
9076 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: difference Fourier map
wR(F2) = 0.135All H-atom parameters refined
S = 1.05w = 1/[σ2(Fo2) + (0.0886P)2] where P = (Fo2 + 2Fc2)/3
4143 reflections(Δ/σ)max < 0.001
331 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.16 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.
xyzUiso*/Ueq
O10.15478 (13)0.65393 (11)0.31309 (7)0.0451 (2)
O2−0.20734 (13)0.07117 (12)0.24962 (8)0.0540 (3)
N10.21630 (13)0.37811 (11)0.34121 (8)0.0364 (2)
N20.11114 (13)0.06677 (11)0.15578 (8)0.0362 (2)
C10.19076 (15)0.65208 (14)0.40716 (9)0.0359 (3)
C20.18871 (17)0.78713 (16)0.44180 (11)0.0432 (3)
C30.22510 (18)0.79071 (17)0.53777 (11)0.0478 (4)
C40.26271 (18)0.66134 (18)0.60108 (11)0.0485 (4)
C50.26484 (17)0.52696 (17)0.56774 (10)0.0430 (3)
C60.23057 (14)0.51821 (14)0.47044 (9)0.0344 (3)
C70.23780 (14)0.37460 (13)0.43405 (9)0.0345 (3)
C80.2708 (2)0.23544 (17)0.50650 (11)0.0475 (3)
C90.22683 (18)0.24468 (14)0.29458 (10)0.0387 (3)
C100.26636 (16)0.28390 (14)0.17541 (9)0.0379 (3)
C110.4468 (2)0.35385 (19)0.13855 (13)0.0535 (4)
C120.1233 (2)0.38992 (17)0.13821 (11)0.0502 (4)
C130.27857 (16)0.14083 (14)0.12936 (10)0.0378 (3)
C140.09534 (15)−0.05311 (13)0.12181 (8)0.0323 (3)
C150.24475 (17)−0.12727 (17)0.05479 (11)0.0411 (3)
C16−0.07908 (15)−0.12069 (13)0.15177 (8)0.0329 (3)
C17−0.10843 (17)−0.25178 (15)0.12019 (10)0.0395 (3)
C18−0.26901 (18)−0.31863 (17)0.15062 (11)0.0464 (3)
C19−0.40732 (18)−0.25416 (18)0.21474 (10)0.0474 (3)
C20−0.38434 (17)−0.12466 (17)0.24715 (10)0.0452 (3)
C21−0.22264 (16)−0.05565 (15)0.21614 (9)0.0384 (3)
H010.170 (2)0.545 (2)0.3073 (15)0.079 (6)*
H20.162 (2)0.8773 (19)0.3937 (13)0.054 (4)*
H30.223 (2)0.8850 (18)0.5615 (12)0.050 (4)*
H40.291 (2)0.664 (2)0.6686 (15)0.072 (5)*
H50.292 (2)0.4369 (19)0.6115 (13)0.054 (4)*
H8B0.194 (2)0.2313 (19)0.5766 (14)0.065 (5)*
H8C0.388 (3)0.231 (2)0.5152 (16)0.084 (6)*
H8A0.246 (3)0.148 (3)0.4832 (17)0.089 (6)*
H9A0.327 (2)0.1723 (18)0.3147 (12)0.054 (4)*
H9B0.115 (2)0.1914 (18)0.3175 (12)0.047 (4)*
H11A0.476 (2)0.375 (2)0.0579 (15)0.068 (5)*
H11C0.542 (3)0.285 (2)0.1658 (14)0.072 (5)*
H11B0.444 (2)0.445 (2)0.1650 (14)0.065 (5)*
H12C0.117 (2)0.482 (2)0.1598 (14)0.066 (5)*
H12B0.140 (2)0.4148 (19)0.0638 (14)0.062 (5)*
H12A−0.003 (3)0.344 (2)0.1627 (15)0.072 (5)*
H13B0.3711 (19)0.0670 (17)0.1561 (11)0.044 (4)*
H13A0.3126 (19)0.1690 (16)0.0504 (12)0.044 (4)*
H02−0.080 (3)0.098 (2)0.2212 (15)0.078 (6)*
H20−0.481 (2)−0.078 (2)0.2925 (13)0.062 (5)*
H19−0.523 (2)−0.3005 (19)0.2356 (13)0.061 (4)*
H18−0.285 (2)−0.4125 (19)0.1276 (12)0.058 (4)*
H17−0.012 (2)−0.2981 (17)0.0743 (12)0.051 (4)*
H15A0.353 (3)−0.080 (2)0.0387 (16)0.084 (6)*
H15B0.274 (3)−0.223 (3)0.0876 (16)0.082 (6)*
H15C0.212 (2)−0.149 (2)−0.0053 (15)0.070 (5)*
U11U22U33U12U13U23
O10.0605 (6)0.0362 (5)0.0397 (5)−0.0023 (4)−0.0153 (4)−0.0034 (4)
O20.0479 (5)0.0556 (6)0.0603 (6)0.0028 (5)0.0009 (5)−0.0310 (5)
N10.0416 (5)0.0328 (6)0.0345 (5)−0.0006 (4)−0.0063 (4)−0.0067 (4)
N20.0390 (5)0.0333 (6)0.0367 (5)0.0016 (4)−0.0063 (4)−0.0098 (4)
C10.0323 (5)0.0390 (7)0.0343 (6)−0.0049 (5)−0.0006 (5)−0.0070 (5)
C20.0430 (6)0.0372 (7)0.0460 (7)−0.0058 (5)0.0006 (6)−0.0083 (6)
C30.0446 (7)0.0480 (8)0.0510 (8)−0.0114 (6)0.0043 (6)−0.0220 (6)
C40.0467 (7)0.0618 (10)0.0400 (7)−0.0077 (6)−0.0038 (6)−0.0203 (6)
C50.0413 (7)0.0511 (8)0.0368 (6)−0.0024 (6)−0.0072 (6)−0.0090 (6)
C60.0290 (5)0.0396 (7)0.0335 (6)−0.0023 (4)−0.0018 (5)−0.0081 (5)
C70.0297 (5)0.0364 (7)0.0354 (6)−0.0016 (4)−0.0035 (5)−0.0044 (5)
C80.0551 (8)0.0426 (8)0.0423 (7)0.0012 (6)−0.0104 (7)−0.0013 (6)
C90.0471 (7)0.0303 (6)0.0381 (6)−0.0020 (5)−0.0072 (5)−0.0062 (5)
C100.0452 (6)0.0306 (6)0.0368 (6)−0.0024 (5)−0.0044 (5)−0.0074 (5)
C110.0588 (9)0.0448 (9)0.0543 (8)−0.0171 (7)0.0058 (7)−0.0163 (7)
C120.0741 (10)0.0347 (8)0.0435 (7)0.0099 (7)−0.0168 (7)−0.0103 (6)
C130.0389 (6)0.0348 (7)0.0392 (6)−0.0012 (5)−0.0036 (5)−0.0108 (5)
C140.0364 (6)0.0316 (6)0.0297 (5)0.0046 (4)−0.0095 (5)−0.0061 (4)
C150.0378 (6)0.0407 (8)0.0460 (7)0.0037 (5)−0.0051 (6)−0.0166 (6)
C160.0363 (6)0.0358 (7)0.0275 (5)0.0035 (5)−0.0099 (5)−0.0054 (4)
C170.0417 (6)0.0413 (7)0.0375 (6)0.0004 (5)−0.0108 (5)−0.0099 (5)
C180.0488 (7)0.0499 (8)0.0445 (7)−0.0099 (6)−0.0138 (6)−0.0099 (6)
C190.0398 (7)0.0662 (10)0.0367 (6)−0.0111 (6)−0.0113 (6)−0.0023 (6)
C200.0370 (6)0.0622 (9)0.0351 (6)0.0033 (6)−0.0060 (5)−0.0085 (6)
C210.0392 (6)0.0458 (7)0.0310 (6)0.0042 (5)−0.0084 (5)−0.0095 (5)
O1—C11.3443 (15)C10—C121.527 (2)
O1—H011.01 (2)C10—C111.5347 (19)
O2—C211.3439 (16)C10—C131.5379 (17)
O2—H021.02 (2)C11—H11A1.039 (18)
N1—C71.2833 (15)C11—H11C1.02 (2)
N1—C91.4622 (15)C11—H11B0.961 (19)
N2—C141.2888 (15)C12—H12C0.934 (19)
N2—C131.4622 (16)C12—H12B0.962 (18)
C1—C21.3987 (18)C12—H12A1.06 (2)
C1—C61.4147 (18)C13—H13B1.026 (15)
C2—C31.380 (2)C13—H13A1.022 (15)
C2—H20.991 (17)C14—C161.4816 (17)
C3—C41.380 (2)C14—C151.5061 (15)
C3—H30.973 (16)C15—H15A0.94 (2)
C4—C51.3844 (19)C15—H15B0.94 (2)
C4—H40.980 (19)C15—H15C0.95 (2)
C5—C61.4014 (17)C16—C171.3964 (17)
C5—H50.959 (17)C16—C211.4191 (16)
C6—C71.4799 (17)C17—C181.3835 (19)
C7—C81.4988 (19)C17—H170.984 (15)
C8—H8B0.994 (18)C18—C191.390 (2)
C8—H8C0.94 (2)C18—H180.991 (17)
C8—H8A0.96 (2)C19—C201.374 (2)
C9—C101.5374 (17)C19—H190.986 (18)
C9—H9A1.031 (17)C20—C211.4004 (19)
C9—H9B0.994 (16)C20—H200.982 (17)
C1—O1—H01101.4 (11)C10—C11—H11C110.7 (11)
C21—O2—H02105.2 (11)H11A—C11—H11C110.3 (14)
C7—N1—C9122.61 (10)C10—C11—H11B109.6 (10)
C14—N2—C13121.02 (9)H11A—C11—H11B110.0 (15)
O1—C1—C2118.27 (12)H11C—C11—H11B107.8 (15)
O1—C1—C6121.67 (11)C10—C12—H12C113.3 (11)
C2—C1—C6120.06 (12)C10—C12—H12B113.7 (10)
C3—C2—C1120.32 (13)H12C—C12—H12B103.8 (15)
C3—C2—H2123.2 (9)C10—C12—H12A111.7 (11)
C1—C2—H2116.5 (9)H12C—C12—H12A108.6 (14)
C4—C3—C2120.55 (13)H12B—C12—H12A105.0 (15)
C4—C3—H3119.5 (9)N2—C13—C10112.30 (9)
C2—C3—H3119.9 (9)N2—C13—H13B107.6 (8)
C3—C4—C5119.67 (13)C10—C13—H13B110.9 (8)
C3—C4—H4120.6 (11)N2—C13—H13A108.3 (8)
C5—C4—H4119.8 (11)C10—C13—H13A107.7 (8)
C4—C5—C6121.73 (14)H13B—C13—H13A110.0 (11)
C4—C5—H5119.8 (10)N2—C14—C16117.60 (9)
C6—C5—H5118.5 (10)N2—C14—C15123.32 (11)
C5—C6—C1117.67 (12)C16—C14—C15119.08 (10)
C5—C6—C7121.47 (12)C14—C15—H15A115.5 (12)
C1—C6—C7120.86 (11)C14—C15—H15B112.0 (12)
N1—C7—C6117.17 (11)H15A—C15—H15B102.8 (17)
N1—C7—C8124.21 (12)C14—C15—H15C111.9 (11)
C6—C7—C8118.62 (11)H15A—C15—H15C112.1 (17)
C7—C8—H8B112.3 (10)H15B—C15—H15C101.2 (17)
C7—C8—H8C109.6 (13)C17—C16—C21117.28 (11)
H8B—C8—H8C107.1 (16)C17—C16—C14121.82 (10)
C7—C8—H8A112.6 (13)C21—C16—C14120.88 (11)
H8B—C8—H8A104.6 (16)C18—C17—C16122.33 (12)
H8C—C8—H8A110.4 (17)C18—C17—H17118.7 (9)
N1—C9—C10110.72 (10)C16—C17—H17119.0 (9)
N1—C9—H9A111.3 (9)C17—C18—C19119.50 (13)
C10—C9—H9A107.0 (8)C17—C18—H18120.2 (9)
N1—C9—H9B111.3 (9)C19—C18—H18120.3 (9)
C10—C9—H9B108.6 (9)C20—C19—C18120.05 (13)
H9A—C9—H9B107.8 (13)C20—C19—H19120.2 (10)
C12—C10—C11110.49 (12)C18—C19—H19119.8 (10)
C12—C10—C9110.72 (10)C19—C20—C21120.84 (12)
C11—C10—C9109.04 (11)C19—C20—H20120.5 (10)
C12—C10—C13110.17 (11)C21—C20—H20118.6 (10)
C11—C10—C13107.19 (10)O2—C21—C20118.48 (11)
C9—C10—C13109.15 (10)O2—C21—C16121.53 (11)
C10—C11—H11A108.6 (10)C20—C21—C16119.99 (12)
O1—C1—C2—C3−179.89 (11)C14—N2—C13—C10178.35 (10)
C6—C1—C2—C3−0.12 (18)C12—C10—C13—N2−57.39 (14)
C1—C2—C3—C4−0.5 (2)C11—C10—C13—N2−177.66 (11)
C2—C3—C4—C50.3 (2)C9—C10—C13—N264.38 (14)
C3—C4—C5—C60.4 (2)C13—N2—C14—C16−179.70 (10)
C4—C5—C6—C1−0.91 (18)C13—N2—C14—C150.90 (18)
C4—C5—C6—C7178.31 (11)N2—C14—C16—C17−178.97 (10)
O1—C1—C6—C5−179.45 (10)C15—C14—C16—C170.45 (17)
C2—C1—C6—C50.78 (17)N2—C14—C16—C21−0.40 (17)
O1—C1—C6—C71.32 (17)C15—C14—C16—C21179.02 (11)
C2—C1—C6—C7−178.45 (10)C21—C16—C17—C18−0.89 (19)
C9—N1—C7—C6177.71 (10)C14—C16—C17—C18177.73 (11)
C9—N1—C7—C8−1.80 (19)C16—C17—C18—C190.1 (2)
C5—C6—C7—N1−175.41 (11)C17—C18—C19—C200.2 (2)
C1—C6—C7—N13.79 (16)C18—C19—C20—C210.2 (2)
C5—C6—C7—C84.13 (17)C19—C20—C21—O2179.69 (12)
C1—C6—C7—C8−176.68 (11)C19—C20—C21—C16−1.0 (2)
C7—N1—C9—C10−158.41 (11)C17—C16—C21—O2−179.41 (11)
N1—C9—C10—C12−59.23 (14)C14—C16—C21—O21.96 (18)
N1—C9—C10—C1162.54 (14)C17—C16—C21—C201.33 (18)
N1—C9—C10—C13179.33 (10)C14—C16—C21—C20−177.30 (11)
D—H···AD—HH···AD···AD—H···A
O1—H01···N11.01 (2)1.56 (2)2.517 (1)156 (2)
O2—H02···N21.02 (2)1.59 (2)2.526 (1)151 (2)
C19—H19···O1i0.99 (2)2.54 (2)3.488 (2)174 (1)
C3—H3···O2i0.97 (2)2.61 (2)3.291 (2)128 (1)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H01⋯N11.01 (2)1.56 (2)2.517 (1)156 (2)
O2—H02⋯N21.02 (2)1.59 (2)2.526 (1)151 (2)
C19—H19⋯O1i0.99 (2)2.54 (2)3.488 (2)174 (1)
C3—H3⋯O2ii0.97 (2)2.61 (2)3.291 (2)128 (1)

Symmetry codes: (i) ; (ii) .

  3 in total

1.  A short history of SHELX.

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

2.  Analysis of the structure-anticancer activity relationship in a set of Schiff bases of macrocyclic 2,6-bis(2- and 4-formylaryloxymethyl)pyridines.

Authors:  V E Kuz'min; V P Lozitsky; G L Kamalov; R N Lozitskaya; A I Zheltvay; A S Fedtchouk; D N Kryzhanovsky
Journal:  Acta Biochim Pol       Date:  2000       Impact factor: 2.149

3.  Bis[N,N'-(2-chlorobenzylidene)ethylenediamine-kappa2N,N']copper(I) dichloridocuprate(I) acetonitrile solvate.

Authors:  Mohammad Hossein Habibi; Morteza Montazerozohori; Kazem Barati; Ross W Harrington; William Clegg
Journal:  Acta Crystallogr C       Date:  2007-11-24       Impact factor: 1.172
  3 in total
  3 in total

1.  2,2'-[(Propane-1,3-diyldinitrilo)bis-(phenyl-methyl-idyne)]diphenol.

Authors:  Robert S Black; David G Billing; Agata Bartyzel; Ewa Cukrowska
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-03-31

2.  N,N'-Bis[(2-hydroxy-phen-yl)(phen-yl)methyl-idene]propane-1,2-diamine.

Authors:  Robert S Black; David G Billing; Agata Bartyzel; Ewa M Cukrowska
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-05-08

3.  {5,5'-Dimeth-oxy-2,2'-[2,2-dimethyl-propane-1,3-diylbis(nitrilo-methanylyl-idene)]diphenolato}palladium(II).

Authors:  Siti Kamilah Che Soh; Mustaffa Shamsuddin; Mohd Mustaqim Rosli; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-03-31
  3 in total

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