Literature DB >> 22904940

2-[(Z)-(3-{[(Z)-2-Hy-droxy-3,5-diiodo-benzyl-idene]amino}-propyl-imino)-meth-yl]-4,6-diiodo-phenol.

Hadi Kargar, Reza Kia, Amir Adabi Ardakani, Muhammad Nawaz Tahir.   

Abstract

In the title compound, C(17)H(14)I(4)N(2)O(2), there are two intra-molecular O-H⋯N hydrogen bonds, which make S(6) ring motifs. In the crystal, there are no significant inter-molecular inter-actions present.

Entities:  

Year:  2012        PMID： 22904940      PMCID： PMC3414953          DOI： 10.1107/S160053681203214X

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


Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to Schiff base ligands, see, for example: Kargar et al. (2011 ▶); Kia et al. (2010 ▶). For a related structure, see: Kargar et al. (2012 ▶).

Experimental

Crystal data

C17H14I4N2O2 M = 785.90 Monoclinic, a = 4.5578 (3) Å b = 16.5095 (11) Å c = 27.2417 (18) Å β = 91.736 (4)° V = 2048.9 (2) Å3 Z = 4 Mo Kα radiation μ = 6.10 mm−1 T = 291 K 0.30 × 0.14 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.262, T max = 0.482 16049 measured reflections 4458 independent reflections 2832 reflections with I > 2σ(I) R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.059 S = 0.98 4458 reflections 226 parameters H-atom parameters constrained Δρmax = 0.61 e Å−3 Δρmin = −0.72 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203214X/su2471sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203214X/su2471Isup2.hkl Supplementary material file. DOI: 10.1107/S160053681203214X/su2471Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H14I4N2O2F(000) = 1432
Mr = 785.90Dx = 2.548 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2453 reflections
a = 4.5578 (3) Åθ = 2.5–27.5°
b = 16.5095 (11) ŵ = 6.10 mm−1
c = 27.2417 (18) ÅT = 291 K
β = 91.736 (4)°Needle, light-yellow
V = 2048.9 (2) Å30.30 × 0.14 × 0.14 mm
Z = 4
Bruker SMART APEXII CCD area-detector diffractometer4458 independent reflections
Radiation source: fine-focus sealed tube2832 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
φ and ω scansθmax = 27.1°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −5→5
Tmin = 0.262, Tmax = 0.482k = −21→17
16049 measured reflectionsl = −34→34
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059H-atom parameters constrained
S = 0.98w = 1/[σ2(Fo2) + (0.0161P)2] where P = (Fo2 + 2Fc2)/3
4458 reflections(Δ/σ)max = 0.002
226 parametersΔρmax = 0.61 e Å−3
0 restraintsΔρmin = −0.72 e Å−3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
I1−0.84612 (9)1.18172 (2)0.147565 (15)0.05342 (13)
I2−0.80900 (9)0.88529 (2)0.274765 (14)0.05293 (13)
I30.66705 (10)0.36716 (2)0.091322 (16)0.06029 (14)
I40.86332 (9)0.67131 (2)0.208721 (14)0.05504 (13)
O1−0.4461 (7)1.0651 (2)0.08517 (12)0.0406 (9)
H1−0.31771.03450.06880.061*
O20.4376 (7)0.7341 (2)0.12415 (12)0.0446 (9)
H20.29460.74970.10300.067*
N1−0.1123 (8)0.9443 (2)0.06648 (15)0.0350 (10)
N20.0681 (9)0.7303 (3)0.05131 (15)0.0395 (11)
C1−0.5088 (10)1.0271 (3)0.12709 (18)0.0303 (12)
C2−0.6977 (10)1.0640 (3)0.16025 (19)0.0322 (12)
C3−0.7811 (11)1.0236 (3)0.20139 (19)0.0377 (13)
H3−0.91051.04800.22260.045*
C4−0.6736 (11)0.9465 (3)0.21164 (17)0.0341 (13)
C5−0.4784 (10)0.9102 (3)0.18129 (18)0.0329 (12)
H5−0.40280.85930.18900.040*
C6−0.3933 (10)0.9501 (3)0.13875 (18)0.0294 (12)
C7−0.1787 (10)0.9141 (3)0.10729 (18)0.0342 (13)
H7−0.08570.86660.11750.041*
C80.1172 (11)0.9065 (3)0.03753 (18)0.0378 (13)
H8A0.24940.87670.05940.045*
H8B0.22990.94870.02200.045*
C9−0.0043 (11)0.8493 (3)−0.00185 (18)0.0391 (14)
H9A0.15300.8340−0.02320.047*
H9B−0.15190.8776−0.02170.047*
C10−0.1411 (11)0.7724 (3)0.01916 (18)0.0415 (14)
H10A−0.31310.78670.03740.050*
H10B−0.20300.7368−0.00750.050*
C110.1244 (10)0.6563 (3)0.04552 (19)0.0375 (13)
H110.02950.62830.02000.045*
C120.3351 (10)0.6128 (3)0.07772 (19)0.0351 (13)
C130.3936 (11)0.5311 (3)0.07004 (19)0.0407 (14)
H130.30150.50360.04410.049*
C140.5879 (11)0.4914 (3)0.1010 (2)0.0387 (13)
C150.7236 (11)0.5313 (3)0.14057 (19)0.0381 (13)
H150.85100.50320.16180.046*
C160.6701 (11)0.6115 (3)0.14830 (18)0.0352 (13)
C170.4795 (11)0.6551 (3)0.11703 (19)0.0347 (13)
U11U22U33U12U13U23
I10.0713 (3)0.0303 (2)0.0585 (3)0.0101 (2)−0.0011 (2)−0.0040 (2)
I20.0675 (3)0.0569 (3)0.0348 (2)−0.0083 (2)0.00783 (19)0.0078 (2)
I30.0820 (3)0.0365 (2)0.0627 (3)0.0121 (2)0.0063 (2)−0.0041 (2)
I40.0633 (3)0.0545 (3)0.0467 (2)−0.0014 (2)−0.0092 (2)−0.0021 (2)
O10.051 (2)0.033 (2)0.038 (2)0.0030 (17)0.0072 (18)0.0107 (18)
O20.057 (2)0.031 (2)0.046 (2)0.0008 (18)−0.0050 (19)0.0028 (19)
N10.034 (3)0.037 (3)0.034 (3)−0.001 (2)0.004 (2)0.003 (2)
N20.042 (3)0.038 (3)0.039 (3)0.001 (2)0.001 (2)0.002 (2)
C10.034 (3)0.023 (3)0.033 (3)−0.010 (2)−0.004 (3)0.001 (3)
C20.036 (3)0.019 (3)0.042 (3)0.001 (2)−0.003 (3)−0.004 (3)
C30.044 (3)0.032 (3)0.038 (3)−0.001 (3)0.006 (3)−0.010 (3)
C40.041 (3)0.033 (3)0.028 (3)−0.006 (3)0.001 (3)−0.002 (3)
C50.038 (3)0.031 (3)0.029 (3)0.001 (2)−0.008 (3)0.002 (3)
C60.032 (3)0.023 (3)0.032 (3)−0.001 (2)−0.007 (2)−0.002 (2)
C70.035 (3)0.031 (3)0.037 (3)0.005 (2)−0.004 (3)−0.001 (3)
C80.037 (3)0.042 (3)0.035 (3)0.002 (3)0.007 (3)0.002 (3)
C90.041 (3)0.046 (4)0.031 (3)0.011 (3)0.001 (3)0.001 (3)
C100.038 (3)0.046 (4)0.039 (3)0.004 (3)−0.007 (3)−0.005 (3)
C110.034 (3)0.044 (4)0.035 (3)−0.001 (3)0.004 (3)0.000 (3)
C120.033 (3)0.036 (3)0.037 (3)−0.001 (3)0.007 (3)0.007 (3)
C130.046 (4)0.039 (3)0.038 (3)−0.002 (3)0.010 (3)−0.005 (3)
C140.041 (3)0.026 (3)0.049 (4)0.004 (2)0.011 (3)−0.003 (3)
C150.043 (3)0.037 (3)0.035 (3)0.004 (3)0.005 (3)0.003 (3)
C160.038 (3)0.031 (3)0.037 (3)−0.002 (3)0.003 (3)0.006 (3)
C170.039 (3)0.030 (3)0.035 (3)−0.004 (3)0.014 (3)0.000 (3)
I1—C22.083 (5)C6—C71.447 (6)
I2—C42.103 (5)C7—H70.9300
I3—C142.100 (5)C8—C91.521 (6)
I4—C162.091 (5)C8—H8A0.9700
O1—C11.341 (5)C8—H8B0.9700
O1—H10.9004C9—C101.533 (6)
O2—C171.334 (5)C9—H9A0.9700
O2—H20.8944C9—H9B0.9700
N1—C71.264 (6)C10—H10A0.9700
N1—C81.468 (6)C10—H10B0.9700
N2—C111.260 (6)C11—C121.468 (7)
N2—C101.452 (6)C11—H110.9300
C1—C21.405 (6)C12—C131.392 (6)
C1—C61.409 (6)C12—C171.422 (7)
C2—C31.367 (6)C13—C141.372 (7)
C3—C41.390 (7)C13—H130.9300
C3—H30.9300C14—C151.392 (7)
C4—C51.370 (6)C15—C161.364 (6)
C5—C61.397 (6)C15—H150.9300
C5—H50.9300C16—C171.397 (7)
C1—O1—H1108.6C8—C9—H9A108.9
C17—O2—H2107.0C10—C9—H9A108.9
C7—N1—C8119.9 (4)C8—C9—H9B108.9
C11—N2—C10121.4 (4)C10—C9—H9B108.9
O1—C1—C2119.7 (4)H9A—C9—H9B107.7
O1—C1—C6121.7 (5)N2—C10—C9110.7 (4)
C2—C1—C6118.5 (5)N2—C10—H10A109.5
C3—C2—C1120.4 (4)C9—C10—H10A109.5
C3—C2—I1119.6 (4)N2—C10—H10B109.5
C1—C2—I1120.0 (4)C9—C10—H10B109.5
C2—C3—C4120.4 (5)H10A—C10—H10B108.1
C2—C3—H3119.8N2—C11—C12122.1 (5)
C4—C3—H3119.8N2—C11—H11118.9
C5—C4—C3120.7 (5)C12—C11—H11118.9
C5—C4—I2119.7 (4)C13—C12—C17120.1 (5)
C3—C4—I2119.6 (4)C13—C12—C11120.6 (5)
C4—C5—C6119.8 (5)C17—C12—C11119.3 (5)
C4—C5—H5120.1C14—C13—C12119.6 (5)
C6—C5—H5120.1C14—C13—H13120.2
C5—C6—C1120.0 (5)C12—C13—H13120.2
C5—C6—C7120.5 (4)C13—C14—C15120.9 (5)
C1—C6—C7119.4 (5)C13—C14—I3120.0 (4)
N1—C7—C6122.9 (5)C15—C14—I3119.1 (4)
N1—C7—H7118.6C16—C15—C14120.1 (5)
C6—C7—H7118.6C16—C15—H15119.9
N1—C8—C9113.1 (4)C14—C15—H15119.9
N1—C8—H8A109.0C15—C16—C17121.1 (5)
C9—C8—H8A109.0C15—C16—I4120.5 (4)
N1—C8—H8B109.0C17—C16—I4118.4 (4)
C9—C8—H8B109.0O2—C17—C16120.3 (5)
H8A—C8—H8B107.8O2—C17—C12121.6 (5)
C8—C9—C10113.3 (4)C16—C17—C12118.1 (5)
O1—C1—C2—C3175.1 (4)C11—N2—C10—C9−127.5 (5)
C6—C1—C2—C3−3.9 (7)C8—C9—C10—N2−55.5 (6)
O1—C1—C2—I1−6.0 (6)C10—N2—C11—C12−179.9 (4)
C6—C1—C2—I1174.9 (3)N2—C11—C12—C13−179.5 (5)
C1—C2—C3—C41.8 (7)N2—C11—C12—C170.5 (8)
I1—C2—C3—C4−177.0 (4)C17—C12—C13—C140.9 (8)
C2—C3—C4—C51.2 (7)C11—C12—C13—C14−179.0 (5)
C2—C3—C4—I2−179.4 (3)C12—C13—C14—C151.1 (8)
C3—C4—C5—C6−2.0 (7)C12—C13—C14—I3177.9 (4)
I2—C4—C5—C6178.6 (3)C13—C14—C15—C16−1.6 (8)
C4—C5—C6—C1−0.2 (7)I3—C14—C15—C16−178.4 (4)
C4—C5—C6—C7177.6 (4)C14—C15—C16—C170.0 (8)
O1—C1—C6—C5−175.9 (4)C14—C15—C16—I4178.2 (4)
C2—C1—C6—C53.1 (7)C15—C16—C17—O2−177.7 (5)
O1—C1—C6—C76.3 (7)I4—C16—C17—O24.1 (6)
C2—C1—C6—C7−174.7 (4)C15—C16—C17—C122.0 (7)
C8—N1—C7—C6177.2 (4)I4—C16—C17—C12−176.3 (3)
C5—C6—C7—N1174.0 (4)C13—C12—C17—O2177.2 (5)
C1—C6—C7—N1−8.2 (7)C11—C12—C17—O2−2.9 (7)
C7—N1—C8—C996.3 (5)C13—C12—C17—C16−2.5 (7)
N1—C8—C9—C10−68.6 (5)C11—C12—C17—C16177.5 (4)
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.901.762.569 (5)148
O2—H2···N20.891.752.564 (5)150
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
O1—H1⋯N10.901.762.569 (5)148
O2—H2⋯N20.891.752.564 (5)150
  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.  5,5'-Bis(diethyl-amino)-2,2'-[2,2-di-methyl-propane-1,3-diylbis-(nitrilo-methylidyne)]diphenol.

Authors:  Reza Kia; Hadi Kargar; Muhammad Nawaz Tahir; Fatemeh Kianoosh
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-08-11

3.  4,4'-Dimeth-oxy-2,2'-[2,2-dimethyl-propane-1,3-diylbis(nitrilo-methanylyl-idene)]diphenol.

Authors:  Hadi Kargar; Reza Kia; Elham Pahlavani; Muhammad Nawaz Tahir
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-02-12

4.  4,4',6,6'-Tetra-chloro-2,2'-[(1E,1'E)-propane-1,3-diylbis(nitrilo-methanylyl-idene)]diphenol.

Authors:  Hadi Kargar; Reza Kia; Amir Adabi Ardakani; Muhammad Nawaz Tahir
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-07-04

5.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  5 in total
  1 in total

1.  {4,4',6,6'-Tetra-iodo-2,2'-[propane-1,3-diylbis(nitrilo-methanylyl-idene)]diphenolato-κ(4)O,N,N',O'}nickel(II).

Authors:  Hadi Kargar; Reza Kia; Amir Adabi Ardakani; Muhammad Nawaz Tahir
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-07-18
  1 in total

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