Literature DB >> 21589396

2-{[4-(Diethyl-amino)-phen-yl]imino-methyl}-4,6-diiodo-phenol.

A Thirugnan Sundar, G Rajagopal, S Murugavel, A Subbiah Pandi.   

Abstract

In the title compound, C(17)H(18)I(2)N(2)O, the dihedral angle between the aromatic rings is 5.4 (1)°. An intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. The crystal packing is stabilized by C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.697 (1) Å].

Entities:  

Year:  2010        PMID： 21589396      PMCID： PMC3011799          DOI： 10.1107/S160053681004417X

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


Related literature

For Schiff base compounds in coordination chemistry, see: Weber et al. (2007 ▶); Chen et al. (2008 ▶). For their role in biological processes, see: May et al. (2004 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Manvizhi et al. (2010 ▶).

Experimental

Crystal data

C17H18I2N2O M = 520.13 Monoclinic, a = 11.5562 (5) Å b = 11.1325 (5) Å c = 15.1207 (6) Å β = 111.958 (2)° V = 1804.15 (13) Å3 Z = 4 Mo Kα radiation μ = 3.49 mm−1 T = 293 K 0.24 × 0.22 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.450, T max = 0.572 26163 measured reflections 7041 independent reflections 4445 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036 wR(F 2) = 0.105 S = 1.01 7041 reflections 202 parameters H-atom parameters constrained Δρmax = 1.14 e Å−3 Δρmin = −1.24 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681004417X/bt5392sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053681004417X/bt5392Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H18I2N2OF(000) = 992
Mr = 520.13Dx = 1.915 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7076 reflections
a = 11.5562 (5) Åθ = 1.9–33.5°
b = 11.1325 (5) ŵ = 3.49 mm−1
c = 15.1207 (6) ÅT = 293 K
β = 111.958 (2)°Block, yellow
V = 1804.15 (13) Å30.24 × 0.22 × 0.16 mm
Z = 4
Bruker APEXII CCD diffractometer7041 independent reflections
Radiation source: fine-focus sealed tube4445 reflections with I > 2σ(I)
graphiteRint = 0.026
Detector resolution: 10.0 pixels mm-1θmax = 33.5°, θmin = 1.9°
ω scansh = −16→17
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −10→17
Tmin = 0.450, Tmax = 0.572l = −23→20
26163 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.105w = 1/[σ2(Fo2) + (0.0437P)2 + 1.1802P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
7041 reflectionsΔρmax = 1.14 e Å−3
202 parametersΔρmin = −1.24 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00078 (19)
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
I10.33796 (2)0.47955 (2)0.048244 (18)0.06508 (9)
I2−0.17213 (2)0.45975 (3)−0.257569 (17)0.07853 (11)
O1−0.18770 (18)0.2470 (2)−0.12546 (15)0.0561 (5)
H1−0.19350.1911−0.09200.084*
N1−0.1205 (2)0.10225 (19)0.01926 (16)0.0424 (5)
N2−0.2604 (2)−0.2797 (2)0.20106 (18)0.0502 (5)
C1−0.0432 (2)0.3956 (2)−0.12942 (18)0.0418 (5)
C2−0.0754 (2)0.2987 (2)−0.08510 (19)0.0401 (5)
C30.0127 (2)0.2571 (2)0.00140 (18)0.0384 (5)
C40.1298 (2)0.3106 (2)0.0396 (2)0.0434 (5)
H40.18820.28270.09690.052*
C50.1596 (2)0.4050 (2)−0.00723 (19)0.0413 (5)
C60.0732 (2)0.4483 (2)−0.09115 (19)0.0424 (5)
H60.09310.5128−0.12200.051*
C7−0.0155 (3)0.1572 (2)0.0516 (2)0.0435 (5)
H70.04470.13210.10910.052*
C8−0.1490 (2)0.0059 (2)0.06823 (19)0.0393 (5)
C9−0.0659 (2)−0.0478 (2)0.1498 (2)0.0448 (6)
H90.0160−0.02060.17530.054*
C10−0.1022 (3)−0.1412 (3)0.1942 (2)0.0460 (6)
H10−0.0442−0.17520.24900.055*
C11−0.2248 (2)−0.1854 (2)0.15812 (19)0.0414 (5)
C12−0.3081 (3)−0.1300 (3)0.0757 (2)0.0474 (6)
H12−0.3906−0.15570.05010.057*
C13−0.2698 (3)−0.0380 (2)0.03204 (19)0.0442 (6)
H13−0.3268−0.0044−0.02340.053*
C14−0.3909 (3)−0.3145 (3)0.1708 (2)0.0564 (7)
H14A−0.3951−0.39520.19360.068*
H14B−0.4266−0.31680.10170.068*
C15−0.4696 (4)−0.2328 (4)0.2052 (3)0.0820 (12)
H15A−0.4382−0.23340.27370.123*
H15B−0.5544−0.26050.18080.123*
H15C−0.4662−0.15250.18320.123*
C16−0.1740 (3)−0.3316 (3)0.2895 (3)0.0681 (9)
H16A−0.0935−0.34210.28420.082*
H16B−0.2042−0.41050.29770.082*
C17−0.1568 (4)−0.2583 (5)0.3760 (3)0.0930 (15)
H17A−0.1348−0.17770.36620.140*
H17B−0.0914−0.29260.43000.140*
H17C−0.2331−0.25750.38740.140*
U11U22U33U12U13U23
I10.04530 (12)0.06753 (15)0.07159 (16)−0.01936 (9)0.00944 (10)−0.00041 (10)
I20.05227 (14)0.1088 (2)0.05720 (15)−0.01130 (12)0.00056 (10)0.03482 (13)
O10.0423 (10)0.0597 (12)0.0577 (12)−0.0140 (9)0.0090 (9)0.0060 (10)
N10.0457 (12)0.0380 (10)0.0479 (12)−0.0021 (9)0.0227 (10)0.0008 (9)
N20.0510 (13)0.0495 (13)0.0506 (14)−0.0104 (10)0.0194 (11)0.0062 (11)
C10.0391 (12)0.0445 (13)0.0393 (13)−0.0014 (10)0.0117 (10)0.0037 (10)
C20.0373 (12)0.0402 (12)0.0435 (13)−0.0012 (9)0.0157 (10)−0.0027 (10)
C30.0385 (12)0.0336 (11)0.0428 (13)−0.0014 (9)0.0149 (10)−0.0011 (9)
C40.0400 (13)0.0404 (12)0.0442 (14)−0.0019 (10)0.0092 (10)0.0023 (11)
C50.0365 (12)0.0382 (12)0.0462 (14)−0.0050 (9)0.0121 (10)−0.0025 (10)
C60.0445 (14)0.0386 (12)0.0440 (14)−0.0029 (10)0.0166 (11)0.0029 (10)
C70.0480 (14)0.0373 (12)0.0475 (14)−0.0004 (10)0.0206 (12)0.0035 (11)
C80.0419 (13)0.0358 (11)0.0437 (13)−0.0019 (9)0.0201 (11)−0.0004 (10)
C90.0365 (12)0.0467 (14)0.0528 (16)−0.0041 (10)0.0186 (11)0.0022 (12)
C100.0421 (13)0.0478 (14)0.0483 (15)−0.0003 (11)0.0172 (11)0.0065 (12)
C110.0449 (13)0.0394 (12)0.0423 (13)−0.0050 (10)0.0191 (11)−0.0015 (10)
C120.0428 (13)0.0521 (15)0.0434 (14)−0.0138 (11)0.0115 (11)−0.0024 (12)
C130.0437 (13)0.0476 (14)0.0380 (13)−0.0064 (11)0.0115 (11)−0.0003 (11)
C140.0550 (17)0.0511 (16)0.0634 (19)−0.0177 (13)0.0225 (15)0.0013 (14)
C150.059 (2)0.096 (3)0.098 (3)−0.009 (2)0.037 (2)−0.010 (2)
C160.066 (2)0.067 (2)0.071 (2)−0.0094 (17)0.0248 (17)0.0222 (18)
C170.089 (3)0.123 (4)0.061 (2)−0.037 (3)0.020 (2)0.004 (2)
I1—C52.085 (2)C9—C101.385 (4)
I2—C12.080 (3)C9—H90.9300
O1—C21.340 (3)C10—C111.403 (4)
O1—H10.8200C10—H100.9300
N1—C71.281 (3)C11—C121.401 (4)
N1—C81.411 (3)C12—C131.378 (4)
N2—C111.375 (3)C12—H120.9300
N2—C141.456 (4)C13—H130.9300
N2—C161.457 (4)C14—C151.510 (5)
C1—C61.381 (4)C14—H14A0.9700
C1—C21.391 (4)C14—H14B0.9700
C2—C31.402 (4)C15—H15A0.9600
C3—C41.391 (3)C15—H15B0.9600
C3—C71.450 (3)C15—H15C0.9600
C4—C51.381 (4)C16—C171.489 (6)
C4—H40.9300C16—H16A0.9700
C5—C61.376 (4)C16—H16B0.9700
C6—H60.9300C17—H17A0.9600
C7—H70.9300C17—H17B0.9600
C8—C91.383 (4)C17—H17C0.9600
C8—C131.384 (4)
C2—O1—H1109.5C11—C10—H10119.4
C7—N1—C8122.5 (2)N2—C11—C12121.9 (2)
C11—N2—C14120.8 (2)N2—C11—C10121.4 (3)
C11—N2—C16120.9 (2)C12—C11—C10116.7 (2)
C14—N2—C16117.2 (2)C13—C12—C11121.1 (2)
C6—C1—C2121.4 (2)C13—C12—H12119.5
C6—C1—I2119.38 (19)C11—C12—H12119.5
C2—C1—I2119.18 (19)C12—C13—C8122.0 (3)
O1—C2—C1120.1 (2)C12—C13—H13119.0
O1—C2—C3121.6 (2)C8—C13—H13119.0
C1—C2—C3118.3 (2)N2—C14—C15114.7 (3)
C4—C3—C2120.0 (2)N2—C14—H14A108.6
C4—C3—C7119.0 (2)C15—C14—H14A108.6
C2—C3—C7121.0 (2)N2—C14—H14B108.6
C5—C4—C3120.2 (2)C15—C14—H14B108.6
C5—C4—H4119.9H14A—C14—H14B107.6
C3—C4—H4119.9C14—C15—H15A109.5
C6—C5—C4120.4 (2)C14—C15—H15B109.5
C6—C5—I1119.91 (19)H15A—C15—H15B109.5
C4—C5—I1119.71 (19)C14—C15—H15C109.5
C5—C6—C1119.6 (2)H15A—C15—H15C109.5
C5—C6—H6120.2H15B—C15—H15C109.5
C1—C6—H6120.2N2—C16—C17114.2 (3)
N1—C7—C3122.2 (3)N2—C16—H16A108.7
N1—C7—H7118.9C17—C16—H16A108.7
C3—C7—H7118.9N2—C16—H16B108.7
C9—C8—C13117.5 (2)C17—C16—H16B108.7
C9—C8—N1125.2 (2)H16A—C16—H16B107.6
C13—C8—N1117.4 (2)C16—C17—H17A109.5
C8—C9—C10121.4 (3)C16—C17—H17B109.5
C8—C9—H9119.3H17A—C17—H17B109.5
C10—C9—H9119.3C16—C17—H17C109.5
C9—C10—C11121.3 (3)H17A—C17—H17C109.5
C9—C10—H10119.4H17B—C17—H17C109.5
C6—C1—C2—O1−177.9 (2)C7—N1—C8—C13173.1 (2)
I2—C1—C2—O10.8 (3)C13—C8—C9—C10−0.6 (4)
C6—C1—C2—C31.6 (4)N1—C8—C9—C10179.1 (3)
I2—C1—C2—C3−179.80 (18)C8—C9—C10—C110.2 (4)
O1—C2—C3—C4177.9 (2)C14—N2—C11—C12−9.1 (4)
C1—C2—C3—C4−1.5 (4)C16—N2—C11—C12−176.7 (3)
O1—C2—C3—C7−1.1 (4)C14—N2—C11—C10171.8 (3)
C1—C2—C3—C7179.5 (2)C16—N2—C11—C104.3 (4)
C2—C3—C4—C50.2 (4)C9—C10—C11—N2178.7 (3)
C7—C3—C4—C5179.2 (2)C9—C10—C11—C12−0.4 (4)
C3—C4—C5—C61.1 (4)N2—C11—C12—C13−178.0 (3)
C3—C4—C5—I1−177.55 (19)C10—C11—C12—C131.1 (4)
C4—C5—C6—C1−1.1 (4)C11—C12—C13—C8−1.6 (4)
I1—C5—C6—C1177.6 (2)C9—C8—C13—C121.3 (4)
C2—C1—C6—C5−0.3 (4)N1—C8—C13—C12−178.4 (2)
I2—C1—C6—C5−178.9 (2)C11—N2—C14—C15−76.2 (4)
C8—N1—C7—C3−179.3 (2)C16—N2—C14—C1591.8 (4)
C4—C3—C7—N1−178.5 (2)C11—N2—C16—C1776.8 (4)
C2—C3—C7—N10.6 (4)C14—N2—C16—C17−91.2 (4)
C7—N1—C8—C9−6.6 (4)
Cg1 is the centroid of the C8–C13 ring.
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.862.592 (3)148
C16—H16B···Cg1ii0.972.943.845 (4)155
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1⋯N10.821.862.592 (3)148
C16—H16B⋯Cg1ii0.972.943.845 (4)155

Symmetry code: (i) .

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