Two new mononuclear gold(I)-nitrogen [N,N′-di(2,6-methyl) phenylformamidine] complexes: Syntheses and crystal structures

Article abstract of DOI:10.1016/j.ica.2011.08.013

Two gold(I) mononuclear complexes have been prepared by reacting gold(I) tetrahydrothiophene with N,N′-di(2,6-methyl)phenylformamidine. The neutral complex [N,N′-di(2,6-methyl)phenylformamidine)-gold(I) chloride (C ₁₇H₂₀AuClN₂) (1), crystallizes in the triclinic group P1 while the cationic [N,N′-di(2,6-methyl)phenylformamidine] (tetrahydrothiophene)-gold(I) (C₂₁H₂₈AuN₂S) (2) crystallizes with a nitrate anion in the monoclinic group P2(1)/n. Both compounds are good starting materials for synthetic gold chemistry.

Full text of DOI:10.1016/j.ica.2011.08.013

Inorganica Chimica Acta 378 (2011) 297–302
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Inorganica Chimica Acta
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Note
Two new mononuclear gold(I)–nitrogen [N,N0-di(2,6-methyl)phenylformamidine]
complexes: Syntheses and crystal structures
⇑
Doris Y. Melgarejo, Gina M. Chiarella, John P. Fackler Jr.
Department of Chemistry, Texas A&M University, P.O. Box 3255, College Station, TX 77843-3255, USA
a r t i c l e i n f o
a b s t r a c t
Article history:
Two gold(I) mononuclear complexes have been prepared by reacting gold(I) tetrahydrothiophene with
N,N0-di(2,6-methyl)phenylformamidine. The neutral complex [N,N0-di(2,6-methyl)phenylformamidine)–
Received 11 July 2011
Accepted 9 August 2011
Available online 23 August 2011
0
ꢀ
gold(I) chloride (C17H20AuClN2) (1), crystallizes in the triclinic group P1 while the cationic [N,N -di(2,6-
methyl)phenylformamidine](tetrahydrothiophene)–gold(I) (C21H28AuN2S) (2) crystallizes with a nitrate
anion in the monoclinic group P2(1)/n. Both compounds are good starting materials for synthetic gold
chemistry.
Keywords:
Mononuclear gold(I) compounds
Formamidine complexes
Sulfur-gold-nitrogen connection
Anion-dependant synthesis
Gold(I) nitrate complex
Ó 2011 Elsevier B.V. All rights reserved.
1. Introduction
metal. A formally tri-coordinated Ag complex, [Ag(HForm)2
(OSO2CF3)] [26] has two neutral formamidines attached to the Ag(I).
In this report we describe the syntheses and crystal structures
which show the mono coordinating ability of the [N,N0-(2,6-di-
methyl)diphenyl-formamidine] to gold (I), resulting in the new
gold complexes (1) and (2) (see Scheme 1).
Mononuclear gold complexes have been widely studied due to
their physicochemical properties [1] and their potential role as pre-
cursors for poly nuclear compounds and molecular frameworks
[2,3]. Gold(I) complexes with luminescent properties in the solid
state and in solution [4] have been studied for use as light emitting
diodes (LED) and in electroluminescence (EL) devices. Mononuclear
gold(I) complexes can lead to the synthesis of various dinuclear or
poly nuclear gold compounds [5]. Mononuclear complexes
[X–M-(ArN(CH)NHAr)] with neutral formamidines can be suitable
precursors for the synthesis of mixed metal arrangements with
short M–M distances. Few such monomers have been described. In
the compound [K(MesForm)(MesHForm)] [6], potassium connects
one protonated formamidine and one anionic formamidinate.
The bi coordinating nature of formamidinates [ArN(CH)NAr], or
[Form], has been extensively used in the production of dimers and
tetramers with only one type of metal center, such as V [7], Cr [8],
Mn, Zn and Co [9], Ni and Pd [10], Cu [11], Mo [12], Ru [13], Rh [14],
Ag [15], W [16], Re [17], Os [18], Ir [19], Pt [20], Au [21] in variable
oxidation states.
2. Experimental
2.1. Materials and methods
The synthesis was carried out under an inert atmosphere using
standard Schlenk techniques unless otherwise noted. Solvents and
reagents were commercially available. Solvents were distilled
under nitrogen and kept over drying sieves. The formamidine,
2,6-Me2-HForm [27], and the Au(THT)Cl were prepared according
to literature methods [28].
2.2. Synthesis of N,N0-di(2,6-methyl)phenylformamidine) gold(I)
chloride (1)
The halides FeCl2, CoCl2, NiCl2 and PtCl2 have been found con-
nected to protonated tolyl formamidines [22] or diphenylbenzami-
dine [23]. In [Pt{C6H3(CH2NMe2)-2,6}dptf] [24] the square planar Pt,
is tri-coordinated by the rigid amine and bonded to a nitrogen atom
of the neutral tolyl formamidine. Another square planar complex of
Pt [25] has three C6F5ꢀ and one formamidine ligands bonded to the
Compound (1) was obtained from an acetonitrile solution of
Au(THT)Cl (1 mmol, 0.320 g) with the neutral formamidine
(1 mmol, 0.252 g) after an hour of stirring. The pale yellow solution
was brought to dryness and the residue rinsed with hexane and ex-
tracted with THF from which 0.35 g of product was collected
(72.2% yield). Vapor diffusion in THF- hexane gave colorless thin
needles, stable to the air. A crystal suitable for X-ray diffraction
was mounted on a nylon loop with Paratone oil, and X-ray diffrac-
tion data were collected in a Bruker diffractometer.
⇑
Corresponding author.
E-mail address: fackler@mail.chem.tamu.edu (J.P. Fackler Jr.).
0020-1693/$ - see front matter Ó 2011 Elsevier B.V. All rights reserved.
doi:10.1016/j.ica.2011.08.013

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D.Y. Melgarejo et al. / Inorganica Chimica Acta 378 (2011) 297–302
Scheme 1. Schematic synthetic procedure of the two gold monomers reported.
Table 1
Crystallographic data.
Compound
1
2
Empirical formula
Formula weight
T (K)
C
17H20AuClN2
C23H34AuN3O4S
645.56
213(2)
484.77
110(2)
Wavelength (Å)
Crystal system
Space group
Unit cell dimensions
a (Å)
0.71073
triclinic
P1
0.71073
monoclinic
P2(1)/c
ꢀ
8.293(2)
8.833(5)
b (Å)
8.314(2)
12.299(7)
c (Å)
12.914(3)
24.098(12)
a
(°)
83.238(3)
90
b (°)
86.685(3)
104.648(18)
c
(°)
64.585(2)
798.6(3)
90
2533(2)
Volume (Å3)
Z
2
4
Dcalc (Mg/m3)
2.016
9.373
464
1.693
5.923
1280
Absorption coefficient (mmꢀ1
F(000)
)
Crystal size (mm3)
h Range (data collection) (°)
Index ranges
0.38 ꢁ 0.06 ꢁ 0.05
0.25 ꢁ 0.19 ꢁ 0.14
2.72–25.02
2.38–25.05
ꢀ9 6 h 6 9, ꢀ9 6 k 6 9, ꢀ15 6 l 6 15
6205
2714 [Rint = 0.1318]
25.02°
ꢀ10 6 h 6 10, ꢀ14 6 k 6 14, ꢀ28 6 l 6 28
19850
4474 [Rint = 0.1191]
25.05°
Reflections collected
Independent reflections
Completeness to h
96.3%
99.7%
Absorption correction
Maximum and minimum transmission
Refinement method
semi-empirical from equivalents
0.6515 and 0.1249
full-matrix least-squares on F2
2714/18/195
semi-empirical from equivalents
0.4910 and 0.3190
full-matrix least-squares on F2
4474/33/301
Data/restraints/parameters
Goodness-of-fit on (GOF) F2
1.241
0.987
Final R indices [I > 2
R indices (all data)
r
(I)]
R1 = 0.0707, wR2 = 0.1695
R1 = 0.0743, wR2 = 0.1723
5.540 and ꢀ3.496
R1 = 0.0428, wR2 = 0.0870
R1 = 0.0631, wR2 = 0.0916
1.361 and ꢀ1.586
Largest diff. peak and hole (eÅꢀ3
)

D.Y. Melgarejo et al. / Inorganica Chimica Acta 378 (2011) 297–302
299
2.3. Synthesis of N,N0-di(2,6-methyl)phenylformamidine] (tetrahydro-
thiophene) gold(I) nitrate (2)
Table 2
Selected bond distances.
Atoms
1
2
X = Cl, S
Bond length
Bond length
To produce compound (2) the chloride anion was removed from
Au(THT)Cl (1 mmol, 0.320 g) using AgNO3 in 1:1 ratio in ethanol at
0 °C. The ethanolic solution was filtered into a Schlenk flask con-
taining the formamidine (1 mmol, 0.252 g). After 1 h of stirring, a
clear solution resulted and was transferred to a vial; the achieved
product weighed 0.51 g, (85% yield). Hexane was vapor diffused
into the vial, which was stored under nitrogen at ꢀ10 °C (in the
freezer). Large flat crystals of (2) sensitive to the light and air grew
in 2 weeks. A piece of the crystal was mounted in a loop with Par-
atone oil to collect X-ray diffraction data.
Au1–X
Au1–N1
N1–C1
N2–C1
N1–C2
N2–C10
2.251(4)
2.269(2)
2.029(2)
1.308(9)
1.326(9)
1.450(9)
1.445(8)
2.030(11)
1.289(17)
1.327(17)
1.395(17)
1.410(19)
2.4. Crystal structure determination and refinement
Data for these compounds were collected on an APEXII v2008.4-
0 (Bruker-Nonius, 2008) CCD area detector system using omega
scans of 0.3°/frame, at 110 K for compound (1) and 213 K for com-
pound (2), with exposition of 30 s/frame. Cell parameters were
determined using the SMART software suite [29]. Data reduction
and integration was performed with the software SAINT [30] of APEX-
II v2008.4-0 [31] for (1) and (2). Absorption corrections were ap-
plied by using the program SADABS [32]. The positions of the Au
atoms were found via direct methods using the program SHELXTL
[33]. Subsequent cycles of least-squares refinement followed by
difference Fourier syntheses revealed the positions of the remain-
ing non-hydrogen atoms. Hydrogen atoms were added in idealized
positions. All hydrogen atoms were included in the calculation of
the structure factors. All non-hydrogen atoms were refined with
anisotropic displacement parameters.
Fig. 1. The structure of (1), showing the almost linear Cl1–Au1–N1 arrangement.
Displacement ellipsoids are drawn at the 50% probability level.
could not be applied). Isotropic behavior restraints at N1 (six re-
straints) were applied during refinement. All H atoms were placed
in calculated positions and refined using a riding model. The C–H
distances in the aromatic rings were fixed at 0.95 Å with Uiso
(H) = 1.2 Ueq(C). The C–H distances at the alkenyl C1 was fixed at
0.94 Å, with Uiso(H) = 1.2Ueq(C). The H atoms on the methyl
groups C8, C9, C16 and C17 were located with a variable torsion
angle about the C–C bond [C–H = 0.98 Å and Uiso(H) = 1.5 Ueq(C)].
The N–H distances were fixed at 0.85 Å with Uiso(H) = 1.2 Ueq(N).
A non-merohedral twin refinement was performed.
3. Results and discussion
The synthetic procedure was carried out under Schlenk condi-
tions, due to the reactivity to air of the reaction mixture, even
though the products are relatively air stable.
In compound (1) the difference peaks of 6.03 and 5.97 are sited
at 0.98 and 0.95 Å from the Au atom (the absorption corrections
using SADABS were insufficient and Face Index Absorption Correction
Fig. 2. The structure of (2), showing the almost linear S1–Au1–N1 arrangement, and the hydrogen bonds N–H(cation)ꢂꢂꢂ(NO3)anion and O–H(solvent)ꢂꢂꢂ(NO3) and the
methylꢂꢂꢂpi-ring interaction (symmetry code: i = 2 ꢀ x, 1/2 + y, 3/2 ꢀ z). Displacement ellipsoids are drawn at the 50% probability level.

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D.Y. Melgarejo et al. / Inorganica Chimica Acta 378 (2011) 297–302
Table 3
Comparison of C–N distances (Å) as qualitative indication of double bond localization in 2,6-substituted formamidinates–metal mononuclear
compounds.
Compound
Space group
N1–C1
N2–C1
Reference
C
31H29ClMoN4O2,0.5(C7H8)
31H28MoN4O2
P21/n
1.29(2)
1.58(4)
1.31(2)
1.37(2)
1.09(3)
1.30(2)
[38]
[38]
[38]
[25]
[26]
[26]
[39]
[40]
[40]
[40]
[40]
[26]
[26]
[41]
[42]
[42]
C
P212121
P21/n
P21/c
C16H36N+, C31H12F15N2Pt
1.285(13)
1.288(6)
1.285(6)
1.292(6)
1.316(5)
1.294(5)
1.322(4)
1.288(4)
1.298(5)
1.297(5)
1.28(1)
1.305(2)
1.305(2)
1.306(4)
1.296(17)
1.298(9)
1.355(13)
1.338(6)
1.325(6)
1.341(6)
1.325(4)
1.344(4)
1.322(4)
1.340(4)
1.350(6)
1.349(6)
1.31 (1)
1.318(3)
1.322(2)
1.309(4)
1.321(17)
1.327(9)
C
27H24AgF3N4O3S
ꢀ
C
104H90Fe4Li2N16O4, 4(C7H8)
P1
C46H63KN4O
P21/n
P21/n
P21/c
P21/c
C
C
C
42H55KN4, C7H8
52H48Cl4Mn2N8
32H28Cl2N5Ta
ꢀ
C26H24Cl2FeN4
P1
C
25H36Cl3GaN2
C17H20AuClN2
21H28AuN2S
P21/c
[43]
This work
This work
ꢀ
P1
C
P21/c
In compound (2) the largest difference peak of 1.72 is sited at
alkenyl C1 was fixed at 0.94 Å, with Uiso(H) = 1.2 Ueq(C). The H
atoms on the methyl groups C8, C9, C16, C17 and C23 were located
with a variable torsion angle about the C–C bond [C–H = 0.97 Å and
Uiso(H) = 1.5 Ueq(C)]. The C–H on CH2 groups C18, C19, C20, C21
and C22 were fixed at 0.98 Å with Uiso(H) = 1.2 Ueq(C). The N–H
distances were fixed at 0.87 Å with Uiso(H) = 1.2 Ueq(N). The
O–H distance was fixed at 0.83 Å with Uiso(H) = 1.5 Ueq(O). Crys-
tallographic data is given in Table 1 and selected bond distances
in Table 2.
1.02 Å from the Au atom (absorption corrections using SADABS soft-
ware and Face Index Absorption Corrections were performed). The
following restraints were applied: at the complex three DELU on
C4 and C5, on C20 and C21 and on C12, C13, eighteen SIMU on
N3 and O2 at the anion and on O4, C22, C23 at the solvent; six iso-
tropic behavior restraints on C23, two disorder restraints at the
ethanol solvent molecule and two anti-bumping restraints.
All H atoms were placed in calculated positions and refined
using a riding model. The C–H distances in the aromatic rings were
fixed at 0.95 Å with Uiso(H) = 1.2 Ueq(C). The C–H distances at the
For the neutral chloride complex [Au(2,6-Me2-HForm)Cl] (1),
gold(I) binds linearly to chloride and to a N from the neutral
Fig. 3. Packing of compound (1) view of the two stacking interactions that mediate a chain of molecules running parallel to the [ꢀ1,1,1] direction and the antiparallel N–
HꢂꢂꢂCl contacts in the extended crystal structure (symmetry codes: i = x, y, z; ii = 1 ꢀ x, 1 ꢀ y, 1 ꢀ z; iii = 1 + x, y, x; i = 2 ꢀ x, ꢀy, ꢀz).
v

D.Y. Melgarejo et al. / Inorganica Chimica Acta 378 (2011) 297–302
301
Table 4
of gravity = Cg(1), is stacked at a distance of 3.587(7) Å with its
symmetry relative at (1 ꢀ x, 1 ꢀ y, 1 ꢀ z), the two rings are not
eclipsed rather there is a slippage of 1.791 Å. The second one is be-
tween ring 2 (C10–C15) and its symmetry relative at (2 ꢀ x, ꢀy, ꢀz)
with a perpendicular distance between the center of gravity of
both rings Cg(2) and Cg(2)iv (iv = 2 ꢀ x, ꢀy, ꢀz) of 3.488(7) Å and
a have a slippage of 1.641 Å . The two stacking interactions mediate
a chain of molecules running parallel to the [ꢀ1,1,1] direction
(Fig. 3).
Hydrogen-bond geometry (Å, °).
D–HꢂꢂꢂA
D–H (Å)
HꢂꢂꢂA (Å)
DꢂꢂꢂA (Å)
D–HꢂꢂꢂA (°)
O4–H4AꢂꢂꢂO2i
O4–H4AꢂꢂꢂO1i
N2–H2ꢂꢂꢂO3i
N2–H2ꢂꢂꢂO1i
0.83
0.83
0.87
0.87
2.79
2.54
2.23
2.35
3.143 (9)
3.184 (9)
3.047 (9)
3.033 (8)
108
136
156
136
Symmetry codes: (i) x, y, z.
formamidine, [ArNH(CH)NAr] which is 2,6-methyl substituted on
the phenyl rings (Fig. 1). In the cationic complex [Au(2,6-Me2-
Form)THT]+ (2), a tetrahydrothiophene (THT) molecule, substitutes
for the chloride. In the unit cell, there is one nitrate anion and one
molecule of ethanol, the latter distributed between two disordered
groups (Fig. 2). In both structures the protonated N2 is accessible
to further chemistry involving the same metal or a different one.
The N2–H proton is anti to the Au–N bond in (1) and (2), conse-
quently the adjacent phenyl ring sits near to the Au–N connection.
All other mononuclear species [22–26] with no ortho substitution
on the formamidinate, but with a crowded metal center, show
the N–H proton pointing cis to the Au–N bond. As in most of the
terminal amidines and guanidines the double bond tends to be
localized at N1–C1 [34], noticeable by the difference in the bond
distances N1–C1 and N2–C1, 1.296 (17), 1.321 (17) Å at (1) and
1.298 (9), 1.327 (9) Å at (2). There are 11 compounds recorded in
the Cambridge Structural Database [35] (CSD, Version 5.30), where
the amidine [ArN(CH)NHAr], having H or C bonded in 2,6 positions
of both phenyl rings, is attached to a metal in a terminal way. Table
3 shows the tendency of these compounds to localize the double
bond.
Evidence for the ring interactions are seen by the short contacts
between the aromatic ring containing C2–C7 and C4ii from the
adjacent molecule (the distance from C2–C7 ring centroid to C4i
(symmetry code ii: 1 ꢀ x, 1 ꢀ y, 1 ꢀ z) is 3.698 (0.018) Å); and be-
tween the aromatic ring C10–C15 and C10ii of a neighboring mol-
ecule (distance from C10–C15 ring centroid to C10iv (symmetry
code i
v: 2 ꢀ x, ꢀy, ꢀz) is 3.556 (0.015) Å).
The phenyl plane at N1 tilts 17.2 (1.3)° away from orthogonality
to the N1–C1–N2 in a rotational manner, and the phenyl plane at
N2 lies 86.1 (1.1)° with respect to the N1–C1–N2 plane. The two
asymmetric units per cell are related by an inversion center. The
distances Au1–N1 2.019 (11) Å at (1), 2.034 (6) Å at (2) are similar,
2.035 (7) Å, to those found at the related dinuclear complex
[Au(2,6-Me2-Form)]2 [36]. The angles Au1–N1–C1, 127.6 (9)° (1)
and 129.8 (5)° (2) are larger than at the constrained dinuclear com-
plex, 120.6 (6)°.
The distances Au1–Cl1 2.252 (4) Å in (1) and Au1–S1 2.269 (2) Å
in (2) compare well to the distances 2.274 (8), 2.292 (13) and 2.279
(9), 2.259 (11) Å found in AuTHTCl [37].
In structure (2) with THT, the solvent molecules and nitrate an-
ions show hydrogen bonding between anion-cation and solvent-
anion. These interactions are given in Table 4 and Fig. 2, and they
prevent pi-pi interactions to form between phenyl rings of the four
molecules in the unit cell in the P21/c space group.
Structure (2) displays a similar tilt of the THT ring to that found
in Au(THT)Cl, with the Au1–S1-(centroid of THT ring) angle of
114.48 (15)°, caused by the lone electron pairs on the sulfur atom.
This tilt brings THT closer to the phenyl group C10–C15.
Complex (1) shows inter molecular short contacts between N2–
HꢂꢂꢂCl1i of 3.333 (13) Å (symmetry code i = 1 + x, y, z) and Cl1ꢂꢂꢂH2
of 2.78 Å, the orientation of those interactions in both molecules
of the unit cell is anti parallel, the molecules thus form chains
propagating along the crystallographic a-axis (Fig. 3).
There are two stacking relationship in this structure, the first
one corresponds to the ring at C2–C7 (ring 1) which, with a center
Fig. 4. Packing of compound (2) (symmetry codes: i = x, y, z; ii = 1 ꢀ x, ꢀ0.5 + y, 1.5 ꢀ z; iii = 1 ꢀ x, 1 ꢀ y, 1 ꢀ z; iv = x, 1.5 ꢀ y, ꢀ0.5 + z).

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[9] F.A. Cotton, L.M. Daniels, L.R. Falvello, J.H. Matonic, C.A. Murillo, X. Wang, H.
The THT moiety has an envelope conformation with C20 at the
Zhou, Inorg. Chim. Acta 266 (1997) 91.
flap; considering the elongation of the displacement ellipsoid for
this atom, the displacement parameters indicate that there may
be a bit of conformational disorder.
There is one weak C—HꢂꢂꢂCg, (where C—H are methyl groups
which are not very acidic) methyl-pi-ring interaction, between
C16–H16AꢂꢂꢂCg(2)i of 3.65(1) Å (Cg(2) = C2–C7) and one short
contact at C21—H21AꢂꢂꢂO4i of 3.319(11) Å (symmetry code
i = 2 ꢀ x, 1/2 + y, 3/2 ꢀ z). It is possible that these contacts stabilize
the structure a bit (Fig. 4).
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The ethanol sits between two Au–S bonds with the closer
distance for C23AꢂꢂꢂS1i (symmetry code i: 1 ꢀ x, ꢀ1/2 + y, 3/2 ꢀ z)
of 3.43(5) Å.
4. Conclusions
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Two new gold(I) monomer compounds described here have
been obtained using simple procedures under nitrogen. The
resulting mononuclear complexes, once formed, are air stable.
Compound (2) has been extremely useful as starting material in
the synthesis of new compounds we have already reported [5].
Acknowledgment
[30] SAINT
, Data Reduction Software, Version 6.36A, Bruker Advanced X-ray
Solutions, Inc., Madison, WI, 2001.
[31] Bruker-Nonius, apexII v2008, 4-0, Bruker-Nonius Inc., Madison, Wisconsin,
The Robert A. Welch Foundation of Houston, Texas, Grant No.
A-0960 is thanked for financial support.
USA, 2008.
[32] G.M. Sheldrick, SADABS, University of Göttingen, Germany, 2006.
[33] G.M. Sheldrick, SHELXTL, Bruker AXS Inc., Madison, Wisconsin, USA, 2008.
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