Bis[2-(2-isopropyl­phenyl­imino)phen­yl]mercury(II)

Flower, K.R.; Pritchard, R.G.

doi:10.1107/S1600536806020150

metal-organic compounds

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ISSN: 2056-9890

Volume 62| Part 7| July 2006| Pages m1469-m1470

https://doi.org/10.1107/S1600536806020150

Bis[2-(2-isopropylphenylimino)phenyl]mercury(II)

Kevin R. Flower ^a ^* and Robin G. Pritchard ^a

^aSchool of Chemistry, University of Manchester, Sackville Street, Manchester, England
^*Correspondence e-mail: k.r.flower@manchester.ac.uk

(Received 19 May 2006; accepted 29 May 2006; online 9 June 2006)

The structure of the centrosymmetric cyclomercurated 2-phenyliminophenyl title compound, [Hg(C₁₆H₁₆N)₂], has been determined at 120 (2) K. The coordination geometry at the Hg atom is essentially square planar.

Comment

The stucture of the centrosymmetric title compound, (I), is shown below. For a discussion of the structure, together with that of a similar complex, see Flower & Pritchard (2006 ).

Figure 1
The molecular structure of (I)

, showing the atomic numbering scheme. Unlabelled atoms are related to labelled atoms by 2 − x, −y, 2 − z. Displacement ellipsoids are shown at the 30% probability level.

Experimental

Caution: preparation of an organomercurial. . Organomercurials are extremely toxic. Compound (I) was prepared by the method previously described (Flower & Pritchard, 2006) (yield 1.12 g, 75%). Elemental analysis C₃₂H₃₂N₂Hg requires: C 59.58, H 4.99, N 4.4%; found: C 59.54, H 5.01, N 4.41%.

Crystal data

[Hg(C₁₆H₁₆N)₂]
M_r = 645.19
Monoclinic, P 2₁ /c
a = 12.585 (3) Å
b = 8.2963 (17) Å
c = 13.244 (3) Å
β = 101.58 (3)°
V = 1354.7 (5) Å³
Z = 2
D_x = 1.582 Mg m⁻³
Mo Kα radiation
μ = 5.70 mm⁻¹
T = 120 (2) K
Prism, yellow
0.16 × 0.12 × 0.04 mm

Data collection

Enraf–Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.462, T_max = 0.804
9987 measured reflections
3078 independent reflections
2244 reflections with I > 2σ(I)
R_int = 0.039
θ_max = 27.5°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.058
S = 1.06
3078 reflections
162 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0195P)² + 0.6915P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.65 e Å⁻³
Δρ_min = −1.50 e Å⁻³

H atoms were positioned geometrically and treated as riding, with C—H = 0.95–1.00 Å and U_iso(H) values of 1.2 or 1.5 times U_eq(C). The deepest hole is located 0.87 Å from Hg1.

Data collection: DENZO (Otwinowski & Minor, 1997 ) and COLLECT (Hooft, 1998 ); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536806020150/sg2030sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806020150/sg2030Isup2.hkl

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'; cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis[2-(2-isopropylphenylimino)phenyl]mercury(I) top

Crystal data top

[Hg(C₁₆H₁₆N)₂]	F(000) = 636
M_r = 645.19	D_x = 1.582 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6064 reflections
a = 12.585 (3) Å	θ = 2.9–27.5°
b = 8.2963 (17) Å	µ = 5.70 mm⁻¹
c = 13.244 (3) Å	T = 120 K
β = 101.58 (3)°	Prism, yellow
V = 1354.7 (5) Å³	0.16 × 0.12 × 0.04 mm
Z = 2

Data collection top

Enraf–Nonius KappaCCD area-detector diffractometer	3078 independent reflections
Graphite monochromator	2244 reflections with I > 2σ(I)
Detector resolution: 9.091 pixels mm^-1	R_int = 0.039
φ and ω scans	θ_max = 27.5°, θ_min = 2.9°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −16→16
T_min = 0.462, T_max = 0.804	k = −9→10
9987 measured reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.058	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0195P)² + 0.6915P] where P = (F_o² + 2F_c²)/3
3078 reflections	(Δ/σ)_max < 0.001
162 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −1.50 e Å⁻³

Special details top

Experimental. ¹H NMR (CDCl₃, 200 MHz): δ 8.51 (s, 1H, CH, J_HHg = 9.81 Hz), 7.63–7.10 (m, 14H, aryl-H), 6.68 (m, 2H, aryl-H), 3.47 (sept, 1H, CH, J_HH = 7.20 Hz), 0.85 (d, 6H, CH₃, J_HH = 7.20 Hz). ¹³C{¹H} (CDCl₃, 100 MHz): δ 167.3, 164.6, 149.9, 143.6, 142.4, 139.1, 133.4, 131.3, 127.3, 126.3, 125.7, 125.1, 118.1, 27.7, 23.2.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Hg1	1	0	1	0.01587 (6)
N1	1.11390 (19)	−0.2604 (3)	1.10205 (17)	0.0194 (5)
C1	0.9102 (2)	−0.0930 (4)	1.1028 (2)	0.0191 (6)
C2	0.8151 (3)	−0.0174 (3)	1.1180 (3)	0.0204 (7)
H2	0.792	0.0798	1.0824	0.024*
C3	0.7540 (3)	−0.0832 (4)	1.1847 (2)	0.0233 (7)
H3	0.69	−0.0301	1.1947	0.028*
C4	0.7861 (3)	−0.2257 (4)	1.2364 (2)	0.0240 (7)
H4	0.7439	−0.2707	1.2814	0.029*
C5	0.8799 (2)	−0.3026 (4)	1.2226 (2)	0.0222 (7)
H5	0.9014	−0.4009	1.2576	0.027*
C6	0.9432 (2)	−0.2362 (3)	1.1573 (2)	0.0177 (6)
C7	1.0429 (2)	−0.3225 (4)	1.1468 (2)	0.0193 (7)
H7	1.0546	−0.4282	1.1744	0.023*
C8	1.2043 (2)	−0.3549 (4)	1.0883 (2)	0.0180 (6)
C9	1.1894 (3)	−0.5072 (3)	1.0444 (3)	0.0191 (7)
H9	1.1182	−0.5501	1.0247	0.023*
C10	1.2776 (3)	−0.5972 (4)	1.0290 (2)	0.0225 (7)
H10	1.2671	−0.7017	0.9994	0.027*
C11	1.3808 (3)	−0.5339 (4)	1.0572 (3)	0.0257 (8)
H11	1.4417	−0.5954	1.0477	0.031*
C12	1.3954 (3)	−0.3805 (4)	1.0992 (2)	0.0236 (7)
H12	1.4668	−0.3382	1.1183	0.028*
C13	1.3082 (2)	−0.2867 (4)	1.1142 (2)	0.0184 (6)
C14	1.3232 (2)	−0.1206 (4)	1.1643 (2)	0.0214 (7)
H14	1.2567	−0.0562	1.1362	0.026*
C15	1.4204 (3)	−0.0284 (4)	1.1401 (4)	0.0373 (10)
H15A	1.4878	−0.0807	1.1748	0.056*
H15B	1.419	0.0829	1.1646	0.056*
H15C	1.4168	−0.0284	1.0655	0.056*
C16	1.3312 (3)	−0.1361 (4)	1.2808 (2)	0.0320 (8)
H16A	1.2651	−0.1867	1.2943	0.048*
H16B	1.3395	−0.0288	1.3124	0.048*
H16C	1.3941	−0.2027	1.3103	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.01480 (10)	0.01619 (10)	0.01730 (10)	0.00034 (6)	0.00482 (6)	0.00045 (6)
N1	0.0160 (14)	0.0202 (13)	0.0216 (13)	−0.0013 (11)	0.0028 (10)	−0.0021 (11)
C1	0.0187 (16)	0.0215 (17)	0.0166 (14)	−0.0037 (13)	0.0024 (11)	−0.0041 (12)
C2	0.0170 (17)	0.0226 (17)	0.0209 (17)	−0.0017 (13)	0.0021 (13)	−0.0049 (12)
C3	0.0182 (17)	0.0252 (18)	0.0282 (17)	−0.0002 (14)	0.0087 (13)	−0.0094 (14)
C4	0.0244 (18)	0.0276 (18)	0.0224 (16)	−0.0083 (15)	0.0103 (13)	−0.0046 (13)
C5	0.0256 (18)	0.0213 (17)	0.0193 (15)	−0.0039 (14)	0.0039 (12)	−0.0003 (12)
C6	0.0166 (16)	0.0185 (16)	0.0175 (14)	0.0004 (12)	0.0020 (11)	−0.0028 (12)
C7	0.0173 (16)	0.0192 (16)	0.0193 (15)	0.0007 (13)	−0.0017 (12)	−0.0016 (12)
C8	0.0176 (16)	0.0191 (15)	0.0173 (14)	0.0033 (13)	0.0036 (11)	0.0005 (12)
C9	0.0174 (17)	0.0212 (17)	0.0180 (16)	−0.0037 (13)	0.0019 (13)	0.0020 (11)
C10	0.0281 (18)	0.0220 (17)	0.0178 (15)	0.0023 (15)	0.0056 (12)	−0.0037 (13)
C11	0.0247 (19)	0.032 (2)	0.0222 (18)	0.0076 (15)	0.0079 (14)	0.0004 (14)
C12	0.0176 (17)	0.0276 (18)	0.0245 (16)	−0.0009 (14)	0.0013 (12)	−0.0001 (14)
C13	0.0191 (16)	0.0205 (16)	0.0157 (14)	0.0006 (13)	0.0037 (11)	0.0017 (12)
C14	0.0178 (16)	0.0165 (16)	0.0292 (16)	−0.0006 (13)	0.0030 (13)	−0.0020 (13)
C15	0.027 (2)	0.032 (2)	0.054 (3)	−0.0079 (16)	0.0132 (19)	−0.0061 (17)
C16	0.037 (2)	0.0272 (19)	0.0297 (18)	−0.0003 (16)	0.0029 (15)	−0.0074 (15)

Geometric parameters (Å, º) top

Hg1—C1ⁱ	2.084 (3)	C9—C10	1.387 (4)
Hg1—C1	2.084 (3)	C9—H9	0.95
N1—C7	1.276 (4)	C10—C11	1.381 (5)
N1—C8	1.423 (4)	C10—H10	0.95
C1—C2	1.401 (5)	C11—C12	1.387 (4)
C1—C6	1.409 (4)	C11—H11	0.95
C2—C3	1.393 (5)	C12—C13	1.391 (4)
C2—H2	0.95	C12—H12	0.95
C3—C4	1.386 (4)	C13—C14	1.525 (4)
C3—H3	0.95	C14—C15	1.531 (5)
C4—C5	1.386 (4)	C14—C16	1.532 (4)
C4—H4	0.95	C14—H14	1
C5—C6	1.401 (4)	C15—H15A	0.98
C5—H5	0.95	C15—H15B	0.98
C6—C7	1.475 (4)	C15—H15C	0.98
C7—H7	0.95	C16—H16A	0.98
C8—C9	1.388 (4)	C16—H16B	0.98
C8—C13	1.402 (4)	C16—H16C	0.98

C1ⁱ—Hg1—C1	180.0000 (10)	C11—C10—H10	120.2
C7—N1—C8	119.3 (3)	C9—C10—H10	120.2
C2—C1—C6	118.4 (3)	C10—C11—C12	119.9 (3)
C2—C1—Hg1	121.3 (2)	C10—C11—H11	120
C6—C1—Hg1	120.3 (2)	C12—C11—H11	120
C3—C2—C1	120.8 (3)	C11—C12—C13	121.7 (3)
C3—C2—H2	119.6	C11—C12—H12	119.1
C1—C2—H2	119.6	C13—C12—H12	119.1
C4—C3—C2	120.3 (3)	C12—C13—C8	117.6 (3)
C4—C3—H3	119.9	C12—C13—C14	122.3 (3)
C2—C3—H3	119.9	C8—C13—C14	119.9 (3)
C3—C4—C5	119.9 (3)	C13—C14—C15	113.3 (3)
C3—C4—H4	120	C13—C14—C16	109.9 (2)
C5—C4—H4	120	C15—C14—C16	111.0 (3)
C4—C5—C6	120.4 (3)	C13—C14—H14	107.5
C4—C5—H5	119.8	C15—C14—H14	107.5
C6—C5—H5	119.8	C16—C14—H14	107.5
C5—C6—C1	120.2 (3)	C14—C15—H15A	109.5
C5—C6—C7	117.8 (3)	C14—C15—H15B	109.5
C1—C6—C7	122.0 (3)	H15A—C15—H15B	109.5
N1—C7—C6	122.4 (3)	C14—C15—H15C	109.5
N1—C7—H7	118.8	H15A—C15—H15C	109.5
C6—C7—H7	118.8	H15B—C15—H15C	109.5
C9—C8—C13	120.7 (3)	C14—C16—H16A	109.5
C9—C8—N1	120.7 (3)	C14—C16—H16B	109.5
C13—C8—N1	118.5 (3)	H16A—C16—H16B	109.5
C10—C9—C8	120.4 (3)	C14—C16—H16C	109.5
C10—C9—H9	119.8	H16A—C16—H16C	109.5
C8—C9—H9	119.8	H16B—C16—H16C	109.5
C11—C10—C9	119.6 (3)

C6—C1—C2—C3	−0.6 (4)	C13—C8—C9—C10	2.5 (4)
Hg1—C1—C2—C3	178.1 (2)	N1—C8—C9—C10	178.5 (3)
C1—C2—C3—C4	−0.6 (5)	C8—C9—C10—C11	−0.4 (5)
C2—C3—C4—C5	0.5 (4)	C9—C10—C11—C12	−0.8 (5)
C3—C4—C5—C6	0.7 (4)	C10—C11—C12—C13	0.0 (5)
C4—C5—C6—C1	−1.8 (4)	C11—C12—C13—C8	2.0 (4)
C4—C5—C6—C7	179.2 (3)	C11—C12—C13—C14	177.5 (3)
C2—C1—C6—C5	1.8 (4)	C9—C8—C13—C12	−3.3 (4)
Hg1—C1—C6—C5	−176.9 (2)	N1—C8—C13—C12	−179.4 (3)
C2—C1—C6—C7	−179.3 (3)	C9—C8—C13—C14	−178.8 (3)
Hg1—C1—C6—C7	2.0 (4)	N1—C8—C13—C14	5.1 (4)
C8—N1—C7—C6	−175.5 (2)	C12—C13—C14—C15	33.3 (4)
C5—C6—C7—N1	−169.2 (3)	C8—C13—C14—C15	−151.4 (3)
C1—C6—C7—N1	11.8 (4)	C12—C13—C14—C16	−91.5 (3)
C7—N1—C8—C9	51.0 (4)	C8—C13—C14—C16	83.8 (3)
C7—N1—C8—C13	−132.9 (3)

Symmetry code: (i) −x+2, −y, −z+2.

Acknowledgements

We thank the EPSRC Crystallographic Service, University of Southampton, for collecting the data.

References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–888. CrossRef CAS IUCr Journals Google Scholar
Flower, K. R. & Pritchard, R. G. (2006). Acta Cryst. E62, m1467–m1468. CSD CrossRef IUCr Journals Google Scholar
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar

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