Literature DB >> 21588500

Bis[1-(2-eth-oxy-phen-yl)-3-(4-nitro-phen-yl)triazenido]mercury(II).

Mohammad Kazem Rofouei, Ehsan Fereyduni, Jafar Attar Gharamaleki, Giuseppe Bruno, Hadi Amiri Rudbari.   

Abstract

In the title compound, [Hg(C(14)H(13)N(4)O(3))(2)], the central Hg atom (site symmetry 2) is six-coordinated by two tridentate 1-(2-eth-oxy-phen-yl)-3-(4-nitro-phen-yl)triazenide ligands through two N and one O atoms. The mononuclear complex mol-ecules are connected into two parallel chains by inter-molecular C-H⋯O hydrogen-bonding inter-actions. These chains are connected to each other by face-to-edge C-H⋯π inter-actions between the CH of the ethoxy groups and the aromatic rings, resulting in a two-dimensional architecture in the ac plane.

Entities:  

Year:  2010        PMID： 21588500      PMCID： PMC3007946          DOI： 10.1107/S1600536810031326

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


Related literature

For related structures, see: Melardi et al. (2007 ▶, 2009 ▶); Rofouei et al. (2009 ▶). For a similar complex with the same ligand, see: Melardi et al. (2010 ▶).

Experimental

Crystal data

[Hg(C14H13N4O3)2] M = 771.1 Orthorhombic, a = 15.4637 (3) Å b = 18.6594 (4) Å c = 9.8008 (2) Å V = 2827.96 (10) Å3 Z = 4 Mo Kα radiation μ = 5.50 mm−1 T = 296 K 0.50 × 0.45 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: integration (SADABS; Bruker, 2005 ▶) T min = 0.129, T max = 0.280 51881 measured reflections 3358 independent reflections 2629 reflections with I > 2σ(I) R int = 0.122

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.110 S = 1.15 3358 reflections 196 parameters 1 restraint H-atom parameters constrained Δρmax = 2.28 e Å−3 Δρmin = −2.52 e Å−3 Absolute structure: Flack (1983 ▶), 1575 Friedel pairs Flack parameter: −0.08 (2) Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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 I, global. DOI: 10.1107/S1600536810031326/pv2312sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031326/pv2312Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Hg(C14H13N4O3)2]F(000) = 1512
Mr = 771.1Dx = 1.811 Mg m−3Dm = 1.8 Mg m−3Dm measured by not measured
Orthorhombic, Aba2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2acCell parameters from 9751 reflections
a = 15.4637 (3) Åθ = 2.6–27.8°
b = 18.6594 (4) ŵ = 5.50 mm−1
c = 9.8008 (2) ÅT = 296 K
V = 2827.96 (10) Å3Irregular, red
Z = 40.50 × 0.45 × 0.20 mm
Bruker APEXII CCD diffractometer3358 independent reflections
Radiation source: fine-focus sealed tube2629 reflections with I > 2σ(I)
graphiteRint = 0.122
φ and ω scansθmax = 27.9°, θmin = 2.6°
Absorption correction: integration (SADABS; Bruker, 2005)h = −20→20
Tmin = 0.129, Tmax = 0.280k = −24→24
51881 measured reflectionsl = −12→12
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038w = 1/[σ2(Fo2) + (0.0655P)2 + 3.2492P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.110(Δ/σ)max < 0.001
S = 1.15Δρmax = 2.28 e Å−3
3358 reflectionsΔρmin = −2.52 e Å−3
196 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.00070 (17)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1575 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: −0.08 (2)
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Hg11.00001.00000.7679 (3)0.03974 (13)
C71.1773 (4)0.9517 (3)0.5961 (6)0.0546 (14)
C20.9670 (4)0.8059 (3)1.0850 (7)0.0545 (14)
H21.02360.81781.06240.065*
O10.7000 (3)0.7116 (3)1.2795 (6)0.0925 (17)
O31.0915 (3)0.9353 (2)0.5744 (5)0.0615 (11)
N10.9199 (3)0.8912 (2)0.9162 (5)0.0554 (11)
C30.9533 (5)0.7573 (3)1.1860 (7)0.0627 (16)
H30.99990.73711.23190.075*
C140.9689 (8)0.8927 (5)0.4560 (11)0.080 (3)
H14A0.94970.86390.38060.120*
H14B0.94880.94100.44440.120*
H14C0.94620.87340.53940.120*
C81.2429 (5)0.9181 (3)0.5204 (8)0.0659 (15)
H81.22970.88410.45430.079*
N30.8716 (3)0.9660 (2)0.7669 (6)0.0492 (9)
N20.8539 (3)0.9140 (3)0.8513 (5)0.0536 (11)
C10.8989 (3)0.8390 (3)1.0133 (6)0.0505 (12)
C40.8678 (5)0.7375 (3)1.2210 (7)0.0586 (15)
H40.85680.70481.29050.070*
C50.8026 (5)0.7683 (4)1.1489 (8)0.0528 (16)
N40.7125 (5)0.7478 (4)1.1825 (7)0.0661 (18)
O20.6572 (3)0.7650 (4)1.1014 (9)0.116 (3)
C60.8148 (3)0.8168 (3)1.0484 (7)0.0526 (13)
H60.76750.83571.00220.063*
C131.0658 (5)0.8922 (4)0.4614 (8)0.0605 (18)
H13A1.08690.84360.47280.073*
H13B1.08950.91150.37740.073*
C91.3285 (5)0.9371 (4)0.5470 (9)0.080 (2)
H91.37280.91540.49790.096*
C121.1960 (5)1.0019 (2)0.6943 (9)0.0420 (15)
C111.2818 (5)1.0216 (5)0.7181 (9)0.0652 (17)
H111.29501.05690.78180.078*
C101.3485 (7)0.9873 (5)0.6443 (13)0.075 (3)
H101.40600.99880.66160.090*
U11U22U33U12U13U23
Hg10.03350 (17)0.04451 (17)0.04121 (18)−0.00398 (7)0.0000.000
C70.047 (3)0.053 (3)0.064 (4)−0.002 (2)0.000 (3)0.013 (3)
C20.033 (3)0.063 (3)0.068 (4)−0.002 (2)−0.001 (3)−0.005 (3)
O10.080 (3)0.101 (4)0.097 (4)−0.019 (3)0.029 (3)0.012 (3)
O30.045 (2)0.068 (2)0.071 (3)−0.0021 (18)0.0040 (18)−0.016 (2)
N10.047 (2)0.059 (3)0.061 (3)−0.006 (2)0.009 (2)0.000 (3)
C30.052 (4)0.069 (4)0.067 (4)0.003 (3)0.000 (3)−0.001 (3)
C140.081 (6)0.073 (5)0.086 (6)−0.008 (5)−0.014 (6)−0.029 (4)
C80.061 (4)0.065 (3)0.071 (3)0.008 (3)0.009 (3)0.017 (4)
N30.037 (2)0.053 (2)0.058 (3)−0.0038 (17)0.002 (2)−0.006 (3)
N20.048 (3)0.057 (3)0.056 (3)−0.008 (2)0.008 (2)−0.004 (2)
C10.042 (3)0.053 (3)0.057 (3)−0.010 (2)0.007 (2)−0.009 (3)
C40.061 (4)0.058 (3)0.057 (4)−0.009 (3)0.005 (3)−0.002 (3)
C50.042 (3)0.054 (3)0.062 (4)−0.004 (2)0.013 (3)−0.012 (3)
N40.047 (4)0.070 (4)0.081 (5)−0.011 (2)0.020 (3)0.012 (3)
O20.040 (3)0.148 (5)0.159 (6)−0.005 (3)0.012 (4)0.066 (5)
C60.035 (2)0.056 (3)0.067 (4)−0.006 (2)0.007 (2)−0.004 (3)
C130.075 (5)0.044 (3)0.062 (4)−0.001 (3)0.009 (4)−0.009 (3)
C90.061 (4)0.082 (5)0.096 (6)0.020 (4)0.023 (4)0.036 (5)
C120.039 (4)0.046 (3)0.041 (4)−0.0032 (18)0.000 (3)0.0117 (19)
C110.043 (4)0.081 (4)0.071 (5)−0.008 (4)0.000 (3)0.012 (4)
C100.040 (4)0.103 (6)0.082 (7)−0.005 (4)0.002 (4)0.032 (5)
Hg1—N3i2.084 (4)C8—C91.394 (11)
Hg1—N32.084 (4)C8—H80.9300
Hg1—O32.656 (5)N3—N21.304 (6)
Hg1—O3i2.656 (5)N3—C12i1.400 (9)
C7—C121.374 (9)C1—C61.407 (6)
C7—O31.378 (7)C4—C51.359 (11)
C7—C81.406 (9)C4—H40.9300
C2—C31.359 (9)C5—C61.351 (10)
C2—C11.409 (8)C5—N41.481 (10)
C2—H20.9300N4—O21.211 (10)
O1—N41.182 (9)C6—H60.9300
O3—C131.425 (8)C13—H13A0.9700
N1—N21.275 (6)C13—H13B0.9700
N1—C11.400 (7)C9—C101.372 (14)
C3—C41.414 (9)C9—H90.9300
C3—H30.9300C12—C111.396 (11)
C14—C131.500 (13)C12—N3i1.400 (9)
C14—H14A0.9600C11—C101.412 (15)
C14—H14B0.9600C11—H110.9300
C14—H14C0.9600C10—H100.9300
N3i—Hg1—N3179.4 (4)N1—C1—C2118.1 (5)
N3i—Hg1—O368.12 (18)C6—C1—C2116.1 (6)
N3—Hg1—O3111.46 (18)C5—C4—C3117.2 (6)
N3i—Hg1—O3i111.46 (18)C5—C4—H4121.4
N3—Hg1—O3i68.12 (18)C3—C4—H4121.4
O3—Hg1—O3i88.9 (2)C6—C5—C4123.9 (6)
C12—C7—O3117.6 (6)C6—C5—N4117.8 (7)
C12—C7—C8121.5 (6)C4—C5—N4118.2 (7)
O3—C7—C8121.0 (6)O1—N4—O2124.3 (7)
C3—C2—C1122.6 (6)O1—N4—C5118.7 (7)
C3—C2—H2118.7O2—N4—C5116.8 (6)
C1—C2—H2118.7C5—C6—C1120.3 (6)
C7—O3—C13120.9 (5)C5—C6—H6119.8
C7—O3—Hg1107.5 (4)C1—C6—H6119.8
C13—O3—Hg1131.5 (4)O3—C13—C14107.6 (5)
N2—N1—C1112.7 (4)O3—C13—H13A110.2
C2—C3—C4119.8 (6)C14—C13—H13A110.2
C2—C3—H3120.1O3—C13—H13B110.2
C4—C3—H3120.1C14—C13—H13B110.2
C13—C14—H14A109.5H13A—C13—H13B108.5
C13—C14—H14B109.5C10—C9—C8121.2 (8)
H14A—C14—H14B109.5C10—C9—H9119.4
C13—C14—H14C109.5C8—C9—H9119.4
H14A—C14—H14C109.5C7—C12—C11119.8 (8)
H14B—C14—H14C109.5C7—C12—N3i119.3 (6)
C9—C8—C7118.2 (7)C11—C12—N3i120.9 (7)
C9—C8—H8120.9C12—C11—C10119.2 (9)
C7—C8—H8120.9C12—C11—H11120.4
N2—N3—C12i118.9 (5)C10—C11—H11120.4
N2—N3—Hg1115.1 (4)C9—C10—C11120.1 (9)
C12i—N3—Hg1125.8 (4)C9—C10—H10120.0
N1—N2—N3113.4 (4)C11—C10—H10120.0
N1—C1—C6125.8 (5)
C12—C7—O3—C13170.6 (6)C3—C2—C1—C6−2.4 (9)
C8—C7—O3—C13−9.5 (8)C2—C3—C4—C50.8 (10)
C12—C7—O3—Hg1−8.0 (6)C3—C4—C5—C6−1.0 (11)
C8—C7—O3—Hg1172.0 (4)C3—C4—C5—N4179.2 (6)
N3i—Hg1—O3—C710.0 (3)C6—C5—N4—O1−171.7 (7)
N3—Hg1—O3—C7−170.4 (3)C4—C5—N4—O18.0 (10)
O3i—Hg1—O3—C7123.7 (4)C6—C5—N4—O213.8 (11)
N3i—Hg1—O3—C13−168.4 (6)C4—C5—N4—O2−166.5 (7)
N3—Hg1—O3—C1311.3 (6)C4—C5—C6—C1−0.5 (10)
O3i—Hg1—O3—C13−54.6 (5)N4—C5—C6—C1179.2 (6)
C1—C2—C3—C40.9 (9)N1—C1—C6—C5−176.8 (6)
C12—C7—C8—C9−0.2 (9)C2—C1—C6—C52.2 (8)
O3—C7—C8—C9179.8 (5)C7—O3—C13—C14−172.6 (6)
O3—Hg1—N3—N294.9 (4)Hg1—O3—C13—C145.6 (8)
O3i—Hg1—N3—N2174.5 (4)C7—C8—C9—C10−0.1 (10)
O3—Hg1—N3—C12i−91.2 (5)O3—C7—C12—C11−178.5 (6)
O3i—Hg1—N3—C12i−11.6 (5)C8—C7—C12—C111.5 (9)
C1—N1—N2—N3175.7 (4)O3—C7—C12—N3i−0.1 (8)
C12i—N3—N2—N1−177.0 (5)C8—C7—C12—N3i179.9 (6)
Hg1—N3—N2—N1−2.6 (6)C7—C12—C11—C10−2.5 (11)
N2—N1—C1—C6−5.5 (7)N3i—C12—C11—C10179.1 (7)
N2—N1—C1—C2175.6 (5)C8—C9—C10—C11−1.0 (12)
C3—C2—C1—N1176.6 (5)C12—C11—C10—C92.3 (13)
D—H···AD—HH···AD···AD—H···A
C8—H8···O1ii0.932.523.446 (9)177
C13—H13A···Cg1iii0.972.863.764 (8)155
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C8—H8⋯O1i0.932.523.446 (9)177
C13—H13A⋯Cg1ii0.972.863.764 (8)155

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.  [1,3-Bis(2-ethoxy-phen-yl)triazenido]chloridomercury(II).

Authors:  Mohammad Reza Melardi; Yasaman Salemi; Saba Razi Kazemi; Mohammad Kazem Rofouei
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-02-21

3.  Chlorido[1-(2-eth-oxy-phen-yl)3-(4-nitro-phen-yl)triazenido]mercury(II).

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