Literature DB >> 21583963

5,5'-Dimeth-oxy-2,2'-[(pentane-1,5-diyl-dioxy)bis-(nitrilo-methyl-idyne)]diphenol.

Yin-Xia Sun1, Li Li, Wen-Kui Dong, Jian-Chao Wu, Jun-Feng Tong.   

Abstract

The mol-ecule of the title compound, C(21)H(26)N(2)O(6), which lies across a crystallographic inversion centre, crystallizes with two unique half-molecules in the symmetric unit and adopts a linear configuration and the imino group is coplanar with the aromatic ring, making a dihedral angle of 3.26 (3)°. Strong intra-molecular O-H⋯N and weak inter-molecular O-H⋯O and C-H⋯O hydrogen bonds and weak inter-molecular π-π stacking inter-actions [centroid-centroid distance = 4.419 (2) Å]establish an infinite three-dimensional supra-molecular structure.

Entities:  

Year:  2009        PMID： 21583963      PMCID： PMC2977826          DOI： 10.1107/S1600536809014986

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


Related literature

For the properties and uses of salen-type compounds, see: Lacroix (2001 ▶); Nishijo et al. (2006 ▶); Onda et al. (2007 ▶); Sun et al. (2004 ▶). For the structures of free salen-type compounds, see: Akine et al. (2005 ▶). For related structures, see: Dong et al. (2008a ▶,b ▶, 2009 ▶).

Experimental

Crystal data

C21H26N2O6 M = 402.44 Triclinic, a = 7.3324 (15) Å b = 7.6214 (17) Å c = 20.372 (3) Å α = 81.525 (1)° β = 89.928 (2)° γ = 67.870 (1)° V = 1041.2 (3) Å3 Z = 2 Mo Kα radiation μ = 0.09 mm−1 T = 298 K 0.43 × 0.28 × 0.14 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.961, T max = 0.987 5481 measured reflections 3618 independent reflections 1641 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.052 wR(F 2) = 0.124 S = 1.01 3618 reflections 264 parameters H-atom parameters constrained Δρmax = 0.15 e Å−3 Δρmin = −0.18 e Å−3 Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014986/hg2502sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014986/hg2502Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C21H26N2O6Z = 2
Mr = 402.44F(000) = 428
Triclinic, P1Dx = 1.284 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.3324 (15) ÅCell parameters from 974 reflections
b = 7.6214 (17) Åθ = 2.9–23.1°
c = 20.372 (3) ŵ = 0.09 mm−1
α = 81.525 (1)°T = 298 K
β = 89.928 (2)°Block-like, colorless
γ = 67.870 (1)°0.43 × 0.28 × 0.14 mm
V = 1041.2 (3) Å3
Siemens SMART 1000 CCD area-detector diffractometer3618 independent reflections
Radiation source: fine-focus sealed tube1641 reflections with I > 2σ(I)
graphiteRint = 0.028
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −8→8
Tmin = 0.961, Tmax = 0.987k = −9→8
5481 measured reflectionsl = −24→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0371P)2] where P = (Fo2 + 2Fc2)/3
3618 reflections(Δ/σ)max < 0.001
264 parametersΔρmax = 0.14 e Å−3
0 restraintsΔρmin = −0.18 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
N1−0.1725 (3)0.8216 (3)−0.07342 (10)0.0615 (6)
N20.8214 (3)0.4398 (3)0.28534 (10)0.0657 (6)
O10.0265 (3)0.7497 (3)−0.05195 (8)0.0749 (6)
O20.7701 (3)0.4917 (3)0.21730 (8)0.0800 (6)
O3−0.5543 (2)0.9488 (3)−0.06470 (8)0.0882 (7)
H3−0.44050.9249−0.05160.132*
O4−0.9588 (3)1.0916 (3)−0.25645 (9)0.0917 (7)
O50.8015 (2)0.3232 (3)0.41215 (8)0.0891 (7)
H50.76100.36330.37320.134*
O61.3399 (3)0.2041 (3)0.55807 (9)0.0906 (7)
C10.0438 (4)0.7272 (4)0.01908 (12)0.0678 (8)
H1A−0.01510.63870.03870.081*
H1B−0.02350.84970.03390.081*
C20.2584 (4)0.6508 (4)0.03966 (11)0.0699 (8)
H2A0.31560.73760.01730.084*
H2B0.32200.52790.02480.084*
C30.3029 (4)0.6250 (4)0.11341 (11)0.0651 (8)
H3A0.25700.52910.13570.078*
H3B0.23050.74490.12920.078*
C40.5200 (4)0.5643 (4)0.13208 (12)0.0662 (8)
H4A0.59300.44650.11510.079*
H4B0.56510.66210.11090.079*
C50.5645 (4)0.5332 (4)0.20517 (12)0.0692 (8)
H5A0.48610.64730.22330.083*
H5B0.53220.42720.22660.083*
C6−0.1984 (4)0.8436 (4)−0.13669 (12)0.0607 (7)
H6−0.08990.8147−0.16280.073*
C7−0.3954 (4)0.9133 (4)−0.16794 (12)0.0528 (7)
C8−0.5646 (4)0.9604 (4)−0.13165 (12)0.0599 (8)
C9−0.7468 (4)1.0168 (4)−0.16277 (13)0.0729 (9)
H9−0.85741.0445−0.13770.087*
C10−0.7693 (4)1.0334 (4)−0.23081 (14)0.0633 (8)
C11−0.6068 (4)0.9916 (4)−0.26870 (13)0.0691 (8)
H11−0.62011.0020−0.31470.083*
C12−0.4233 (4)0.9337 (4)−0.23622 (12)0.0661 (8)
H12−0.31320.9071−0.26150.079*
C13−0.9911 (4)1.1077 (4)−0.32617 (14)0.0919 (11)
H13A−0.93391.1923−0.34890.138*
H13B−1.13031.1582−0.33760.138*
H13C−0.93100.9834−0.33920.138*
C140.9944 (4)0.4320 (4)0.29886 (13)0.0642 (8)
H141.06490.46600.26470.077*
C151.0837 (4)0.3722 (4)0.36552 (12)0.0534 (7)
C160.9873 (4)0.3203 (4)0.42012 (13)0.0611 (8)
C171.0779 (4)0.2636 (4)0.48276 (13)0.0727 (9)
H171.01240.22800.51820.087*
C181.2649 (4)0.2590 (4)0.49373 (13)0.0627 (8)
C191.3648 (4)0.3074 (4)0.44140 (13)0.0669 (8)
H191.49220.30230.44830.080*
C201.2727 (4)0.3637 (4)0.37860 (13)0.0670 (8)
H201.34020.39750.34340.080*
C211.5276 (4)0.2114 (4)0.57277 (13)0.0959 (11)
H21A1.62820.11710.55240.144*
H21B1.55520.18530.62000.144*
H21C1.52510.33660.55580.144*
U11U22U33U12U13U23
N10.0551 (15)0.0683 (17)0.0543 (15)−0.0171 (13)−0.0062 (11)−0.0058 (12)
N20.0634 (16)0.0769 (18)0.0557 (15)−0.0256 (14)−0.0110 (12)−0.0096 (12)
O10.0562 (12)0.1062 (17)0.0539 (12)−0.0218 (11)−0.0072 (9)−0.0116 (10)
O20.0725 (14)0.1078 (18)0.0599 (12)−0.0379 (12)−0.0111 (10)−0.0041 (11)
O30.0699 (13)0.140 (2)0.0495 (12)−0.0358 (13)0.0041 (10)−0.0105 (11)
O40.0660 (14)0.128 (2)0.0742 (14)−0.0307 (13)−0.0134 (11)−0.0099 (12)
O50.0537 (12)0.150 (2)0.0738 (13)−0.0519 (13)0.0011 (9)−0.0124 (12)
O60.0790 (15)0.132 (2)0.0708 (14)−0.0603 (14)−0.0180 (11)0.0084 (12)
C10.0641 (19)0.078 (2)0.0539 (18)−0.0198 (17)−0.0075 (14)−0.0074 (15)
C20.0615 (19)0.083 (2)0.0596 (18)−0.0226 (17)−0.0068 (14)−0.0071 (15)
C30.0636 (19)0.066 (2)0.0589 (18)−0.0185 (16)−0.0073 (14)−0.0055 (14)
C40.068 (2)0.065 (2)0.0620 (18)−0.0220 (16)−0.0093 (14)−0.0086 (14)
C50.064 (2)0.072 (2)0.0655 (19)−0.0217 (17)−0.0124 (15)−0.0053 (15)
C60.0586 (18)0.069 (2)0.0511 (17)−0.0209 (16)0.0053 (14)−0.0088 (14)
C70.0553 (18)0.0558 (19)0.0467 (16)−0.0212 (15)−0.0018 (14)−0.0061 (13)
C80.0620 (19)0.072 (2)0.0433 (17)−0.0251 (16)0.0005 (14)−0.0045 (14)
C90.0581 (19)0.104 (3)0.0542 (19)−0.0273 (18)0.0038 (14)−0.0135 (16)
C100.0546 (19)0.068 (2)0.063 (2)−0.0212 (16)−0.0073 (16)−0.0059 (15)
C110.073 (2)0.082 (2)0.0518 (18)−0.0293 (18)−0.0038 (16)−0.0088 (15)
C120.0633 (19)0.083 (2)0.0512 (18)−0.0259 (17)0.0038 (14)−0.0120 (15)
C130.089 (2)0.100 (3)0.080 (2)−0.029 (2)−0.0296 (18)−0.0106 (19)
C140.0625 (19)0.070 (2)0.0630 (19)−0.0279 (17)0.0019 (15)−0.0109 (15)
C150.0495 (17)0.0574 (19)0.0555 (17)−0.0213 (14)0.0037 (13)−0.0139 (13)
C160.0417 (16)0.079 (2)0.0681 (19)−0.0269 (15)0.0022 (14)−0.0186 (15)
C170.0602 (19)0.108 (3)0.0597 (19)−0.0455 (18)0.0014 (15)−0.0068 (17)
C180.0563 (18)0.073 (2)0.0621 (19)−0.0302 (16)−0.0057 (15)−0.0061 (15)
C190.0470 (17)0.083 (2)0.076 (2)−0.0294 (16)0.0010 (15)−0.0134 (16)
C200.0539 (18)0.085 (2)0.069 (2)−0.0357 (17)0.0067 (14)−0.0086 (16)
C210.075 (2)0.123 (3)0.097 (2)−0.054 (2)−0.0304 (18)0.003 (2)
N1—C61.280 (2)C6—C71.449 (3)
N1—O11.396 (2)C6—H60.9300
N2—C141.276 (3)C7—C121.383 (3)
N2—O21.395 (2)C7—C81.398 (3)
O1—C11.432 (2)C8—C91.364 (3)
O2—C51.432 (3)C9—C101.378 (3)
O3—C81.354 (2)C9—H90.9300
O3—H30.8200C10—C111.379 (3)
O4—C101.367 (3)C11—C121.382 (3)
O4—C131.420 (3)C11—H110.9300
O5—C161.363 (2)C12—H120.9300
O5—H50.8200C13—H13A0.9600
O6—C181.365 (3)C13—H13B0.9600
O6—C211.431 (3)C13—H13C0.9600
C1—C21.493 (3)C14—C151.441 (3)
C1—H1A0.9700C14—H140.9300
C1—H1B0.9700C15—C201.387 (3)
C2—C31.506 (3)C15—C161.405 (3)
C2—H2A0.9700C16—C171.371 (3)
C2—H2B0.9700C17—C181.376 (3)
C3—C41.513 (3)C17—H170.9300
C3—H3A0.9700C18—C191.377 (3)
C3—H3B0.9700C19—C201.378 (3)
C4—C51.490 (3)C19—H190.9300
C4—H4A0.9700C20—H200.9300
C4—H4B0.9700C21—H21A0.9600
C5—H5A0.9700C21—H21B0.9600
C5—H5B0.9700C21—H21C0.9600
C6—N1—O1112.7 (2)C9—C8—C7120.7 (2)
C14—N2—O2111.7 (2)C8—C9—C10120.9 (3)
N1—O1—C1109.48 (18)C8—C9—H9119.5
N2—O2—C5110.15 (19)C10—C9—H9119.5
C8—O3—H3109.5O4—C10—C9115.7 (3)
C10—O4—C13118.4 (2)O4—C10—C11124.0 (3)
C16—O5—H5109.5C9—C10—C11120.3 (2)
C18—O6—C21117.9 (2)C10—C11—C12117.9 (2)
O1—C1—C2107.6 (2)C10—C11—H11121.1
O1—C1—H1A110.2C12—C11—H11121.1
C2—C1—H1A110.2C11—C12—C7123.3 (3)
O1—C1—H1B110.2C11—C12—H12118.4
C2—C1—H1B110.2C7—C12—H12118.4
H1A—C1—H1B108.5O4—C13—H13A109.5
C1—C2—C3114.5 (2)O4—C13—H13B109.5
C1—C2—H2A108.6H13A—C13—H13B109.5
C3—C2—H2A108.6O4—C13—H13C109.5
C1—C2—H2B108.6H13A—C13—H13C109.5
C3—C2—H2B108.6H13B—C13—H13C109.5
H2A—C2—H2B107.6N2—C14—C15121.9 (2)
C2—C3—C4113.2 (2)N2—C14—H14119.1
C2—C3—H3A108.9C15—C14—H14119.1
C4—C3—H3A108.9C20—C15—C16116.6 (2)
C2—C3—H3B108.9C20—C15—C14120.6 (2)
C4—C3—H3B108.9C16—C15—C14122.8 (2)
H3A—C3—H3B107.8O5—C16—C17118.2 (2)
C5—C4—C3113.1 (2)O5—C16—C15120.9 (2)
C5—C4—H4A109.0C17—C16—C15121.0 (2)
C3—C4—H4A109.0C16—C17—C18120.6 (2)
C5—C4—H4B109.0C16—C17—H17119.7
C3—C4—H4B109.0C18—C17—H17119.7
H4A—C4—H4B107.8O6—C18—C17115.9 (2)
O2—C5—C4108.8 (2)O6—C18—C19124.0 (2)
O2—C5—H5A109.9C17—C18—C19120.1 (2)
C4—C5—H5A109.9C18—C19—C20118.8 (2)
O2—C5—H5B109.9C18—C19—H19120.6
C4—C5—H5B109.9C20—C19—H19120.6
H5A—C5—H5B108.3C19—C20—C15122.9 (2)
N1—C6—C7120.5 (2)C19—C20—H20118.6
N1—C6—H6119.8C15—C20—H20118.6
C7—C6—H6119.8O6—C21—H21A109.5
C12—C7—C8116.8 (2)O6—C21—H21B109.5
C12—C7—C6120.5 (2)H21A—C21—H21B109.5
C8—C7—C6122.6 (2)O6—C21—H21C109.5
O3—C8—C9117.5 (2)H21A—C21—H21C109.5
O3—C8—C7121.7 (2)H21B—C21—H21C109.5
C6—N1—O1—C1−179.4 (2)C9—C10—C11—C12−0.1 (4)
C14—N2—O2—C5−169.4 (2)C10—C11—C12—C71.0 (4)
N1—O1—C1—C2−179.9 (2)C8—C7—C12—C11−2.0 (4)
O1—C1—C2—C3177.9 (2)C6—C7—C12—C11177.2 (3)
C1—C2—C3—C4−174.9 (2)O2—N2—C14—C15−176.9 (2)
C2—C3—C4—C5−178.3 (2)N2—C14—C15—C20179.5 (3)
N2—O2—C5—C4−173.06 (19)N2—C14—C15—C16−0.6 (4)
C3—C4—C5—O2−175.4 (2)C20—C15—C16—O5−179.7 (2)
O1—N1—C6—C7178.8 (2)C14—C15—C16—O50.4 (4)
N1—C6—C7—C12−178.8 (2)C20—C15—C16—C17−0.3 (4)
N1—C6—C7—C80.4 (4)C14—C15—C16—C17179.8 (2)
C12—C7—C8—O3−178.9 (2)O5—C16—C17—C18−179.6 (3)
C6—C7—C8—O31.9 (4)C15—C16—C17—C180.9 (4)
C12—C7—C8—C92.3 (4)C21—O6—C18—C17−175.2 (3)
C6—C7—C8—C9−176.9 (2)C21—O6—C18—C195.0 (4)
O3—C8—C9—C10179.5 (2)C16—C17—C18—O6178.8 (2)
C7—C8—C9—C10−1.6 (4)C16—C17—C18—C19−1.4 (4)
C13—O4—C10—C9−178.8 (2)O6—C18—C19—C20−179.0 (2)
C13—O4—C10—C110.9 (4)C17—C18—C19—C201.2 (4)
C8—C9—C10—O4−179.8 (3)C18—C19—C20—C15−0.6 (4)
C8—C9—C10—C110.5 (4)C16—C15—C20—C190.1 (4)
O4—C10—C11—C12−179.8 (2)C14—C15—C20—C19−180.0 (2)
D—H···AD—HH···AD···AD—H···A
O3—H3···N10.821.902.610 (3)144
O5—H5···N20.821.902.628 (3)147
O3—H3···O3i0.822.683.045 (3)109
C2—H2A···O3ii0.972.583.533 (4)168
C19—H19···O5ii0.932.443.300 (4)154
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O3—H3⋯N10.821.902.610 (3)144
O5—H5⋯N20.821.902.628 (3)147
O3—H3⋯O3i0.822.683.045 (3)109
C2—H2A⋯O3ii0.972.583.533 (4)168
C19—H19⋯O5ii0.932.443.300 (4)154

Symmetry codes: (i) ; (ii) .

  5 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.  Oxime-based salen-type tetradentate ligands with high stability against imine metathesis reaction.

Authors:  Shigehisa Akine; Takanori Taniguchi; Wenkui Dong; Sayuri Masubuchi; Tatsuya Nabeshima
Journal:  J Org Chem       Date:  2005-03-04       Impact factor: 4.354

3.  6,6'-Dihydr-oxy-2,2'-[(pentane-1,5-diyl-dioxy)bis-(nitrilo-methyl-idyne)]diphenol.

Authors:  Wen-Kui Dong; Xue-Ni He; Yong-Hong Guan; Li Xu; Zong-Li Ren
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-07-26

4.  2,2'-{1,1'-[Pentane-1,5-diyl-bis(oxy-nitrilo)]-diethyl-idyne}diphenol.

Authors:  Wen-Kui Dong; Zhong-Wu Lv; Xue-Ni He; Yong-Hong Guan; Jun-Feng Tong
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-10-04

5.  Directed assembly of transition-metal-coordinated molecular loops and squares from salen-type components. Examples of metalation-controlled structural conversion.

Authors:  Shih-Sheng Sun; Charlotte L Stern; SonBinh T Nguyen; Joseph T Hupp
Journal:  J Am Chem Soc       Date:  2004-05-26       Impact factor: 15.419
  5 in total
  1 in total

1.  5,5'-Dimeth-oxy-2,2'-[(nonane-1,9-diyldi-oxy)bis-(nitrilo-methyl-idyne)]diphenol.

Authors:  Li Li; Hong-Zheng Ma; Su-Xia Gao; Wen-Kui Dong; Jian-Chao Wu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-17
  1 in total

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