research communications
of chlorido(2-{[2-(phenylcarbamothioyl)hydrazin-1-ylidene](pyridin-2-yl)methyl}pyridin-1-ium)gold(I) chloride sesquihydrate
aLaboratory of Inorganic Synthesis and Crystallography, University of Brasília, IQ, Campus Universitário Darcy Ribeiro, CEP 70904970, PO Box 4478, Brasília - DF, Brazil
*Correspondence e-mail: ccgatto@gmail.com
The title complex, [AuCl(C18H16N5S)]Cl·1.5H2O, may be considered as a gold(I) compound with the corresponding metal site coordinated by a thiosemicarbazone ligand through the S atom. The ligand adopts an E conformation and the gold(I) atom displays the expected linear geometry with a Cl atom also bonded to the metal ion [Cl—Au—S = 174.23 (5)°]. One of the pyridyl rings is protonated, giving the gold complex an overall positive charge. Two solvent water molecules, one of which is located on a twofold rotation axis, and a non-coordinating chloride ion complete the structural assembly. The molecular structure is stabilized by intramolecular and intermolecular N—H⋯Cl, N—H⋯N, O—H⋯Cl and O—H⋯O hydrogen bonding.
Keywords: crystal structure; gold(I) complex; thiosemicarbazone; hydrogen bonding.
CCDC reference: 1419509
1. Chemical context
Thiosemicarbazones are generated from reactions of thiosemicarbazides with either an aldehyde or a ketone. They are compounds that can coordinate to transition metals and exhibit keto–enol et al., 1996). Thiosemicarbazones are known to have diverse biological activity, including anti-malarial properties and antibacterial, antitubercular, antiviral and antitumor activity (Beraldo & Gambino, 2004, Casini et al., 2008, Khanye et al., 2010). The study of gold compounds with thiosemicarbazones has great importance: the literature reports that some compounds of this type have been shown to exhibit biological activity and have potential applications (Casini et al., 2008, Lessa et al., 2011).
(Duan2. Structural commentary
In the title complex (Fig. 1), the di-2-pyridyl ketone phenylthiosemicarbazone ligand is protonated at the pyridine (py) nitrogen and only the sulfur donor atom is used to bond to the central metal ion. The thiosemicarbazone adopts the E conformation in relation to the C6=N3 and N4—C12 bonds.
The 4] during the synthesis. Two solvent water molecules and an non-coordinating chloride ion complete the structural assembly and are hydrogen bonded to the cationic complex.
data confirm reduction of gold(III) of the starting material [HPy][AuClThe gold(I) atom displays the expected linear geometry, with a Cl—Au—S coordination angle of 174.23 (5)°, close to the ideal angle of 180° expected for sp of the metal.
The C12—S1 bond length reported for di-2-pyridyl ketone phenylthiosemicarbazone is 1.676 (2) Å and it is lengthened to 1.713 (4) Å on coordination to gold; this is typical of the ketone form with a concomitant shortening of the N3—N4 bond (Suni et al., 2006).
An intramolecular N4—H4A⋯N2 hydrogen bond (Table 1) is observed.
3. Supramolecular features
In the crystal, the chloride ion is linked to the complex molecule by N—H⋯Cl hydrogen bonds. The molecular structure is also stabilized by intermolecular O—H⋯Cl and O—H⋯O hydrogen bonding involving the water molecules. Therefore, upon protonation of the ligand, hydrogen-bond formation with the chloride ion results in a stabilization of the conformation of the cationic gold complex, and hydrogen bonding plays an important role in the crystallization of the compound (Table 1 and Fig. 2).
4. Related studies
For the preparation of coordination compounds of thiomemicarbazones with gold, see: Castiñeiras et al. (2012); Khanye et al. (2010); Lessa et al. (2011); Sreekanth et al. (2004). For the spectroscopic (FT–IR) properties of thiosemicarbazones and the of thiosemicarbazones, see: Beraldo & Gambino (2004); Duan et al. (1996); Pereiras-Gabián et al. (2004); Suni et al. (2006). For the crystal structures of di-2-pyridyl ketone phenylthiosemicarbazone and coordination compounds with this thiosemicarbazone, see: Bernhardt et al. (2009); Philip et al. (2005); Suni et al. (2006, 2007). For structure–activity studies of thiosemicarbazones, see: Bernhardt et al. (2009); Casini et al. (2008); Duan et al. (1996).
5. Synthesis and crystallization
Di-2-pyridyl ketone phenylthiosemicarbazone (1 mmol) was dissolved in about 5 ml of CH3CN and added to a solution of [HPy][AuCl4] (1 mmol) in 5 ml of CH3CN. A clear yellow solution was formed after heating the mixture to reflux for three h. Orange crystals deposited upon slow cooling of the solvent. Yield: 69%, m.p. 491 K. Elemental analysis, found: C, 33.71; H, 3.15; N, 10.04%; calculated for C36H38Au2Cl4N10O3S2: C, 33.87; H, 3.16; N, 10.97%. IR (νmax cm−1): 3421 (O—H), 3281 (N—H), 2927 (N—H+), 1694 (C=N), 1150 (N—N), 765 (C=S).
6. Refinement
Crystal data, data collection and structure . Hydrogen atoms potentially involved in hydrogen-bonding interactions were located in difference electron-density maps and their positional and isotropic displacement parameters were refined. Hydrogen atoms of water molecules were refined with distance restraints, with an H⋯H separation of 1.38 (2) Å, the H—O distance restrained to 0.82 (2) Å and with Uiso = 1.5Ueq(O). Other H atoms were included in the at calculated positions and treated as riding with Uiso(H) = 1.2Ueq(C).
details are summarized in Table 2
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Supporting information
CCDC reference: 1419509
https://doi.org/10.1107/S2056989015015480/zl2637sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015015480/zl2637Isup3.hkl
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: DIAMOND (Crystal Impact, 2014); software used to prepare material for publication: publCIF (Westrip, 2010).[AuCl(C18H16N5S)]Cl·1.5H2O | Dx = 1.964 Mg m−3 |
Mr = 629.31 | Melting point: 491 K |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 31.0939 (7) Å | Cell parameters from 4811 reflections |
b = 12.2704 (3) Å | θ = 2.7–25.2° |
c = 11.8851 (3) Å | µ = 7.28 mm−1 |
β = 110.174 (1)° | T = 296 K |
V = 4256.38 (18) Å3 | Block, red |
Z = 8 | 0.24 × 0.22 × 0.14 mm |
F(000) = 2424 |
Bruker CCD SMART APEXII diffractometer | 3220 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.038 |
phi & ω scans | θmax = 26.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −37→38 |
Tmin = 0.274, Tmax = 0.429 | k = −14→15 |
15424 measured reflections | l = −14→14 |
4345 independent reflections |
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)] = 0.031 | Hydrogen site location: mixed |
wR(F2) = 0.072 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0364P)2] where P = (Fo2 + 2Fc2)/3 |
4345 reflections | (Δ/σ)max = 0.001 |
271 parameters | Δρmax = 0.97 e Å−3 |
3 restraints | Δρmin = −0.78 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Au1 | 0.25092 (2) | 0.60284 (2) | 0.04569 (2) | 0.04892 (9) | |
S1 | 0.32514 (5) | 0.61867 (10) | 0.16165 (13) | 0.0581 (4) | |
Cl1 | 0.17486 (5) | 0.57863 (11) | −0.05533 (12) | 0.0610 (4) | |
C12 | 0.34886 (15) | 0.4928 (3) | 0.1607 (4) | 0.0388 (10) | |
N3 | 0.35315 (13) | 0.3345 (3) | 0.0578 (3) | 0.0370 (9) | |
N5 | 0.38617 (12) | 0.4607 (3) | 0.2458 (3) | 0.0424 (9) | |
H5A | 0.3953 | 0.3954 | 0.2403 | 0.051* | |
N4 | 0.32925 (13) | 0.4234 (3) | 0.0690 (3) | 0.0401 (9) | |
H4A | 0.3022 | 0.4355 | 0.0190 | 0.048* | |
C13 | 0.41343 (15) | 0.5235 (4) | 0.3473 (4) | 0.0410 (11) | |
C5 | 0.36773 (15) | 0.1810 (3) | −0.0344 (4) | 0.0355 (10) | |
C6 | 0.33459 (15) | 0.2653 (3) | −0.0268 (3) | 0.0342 (10) | |
C7 | 0.28703 (16) | 0.2612 (3) | −0.1109 (3) | 0.0376 (10) | |
C4 | 0.36887 (17) | 0.1356 (3) | −0.1392 (4) | 0.0431 (11) | |
H4 | 0.3469 | 0.1549 | −0.2121 | 0.052* | |
C1 | 0.43375 (18) | 0.0813 (3) | 0.0737 (5) | 0.0479 (12) | |
H1 | 0.4560 | 0.0642 | 0.1470 | 0.057* | |
C18 | 0.43406 (17) | 0.6200 (4) | 0.3336 (5) | 0.0472 (12) | |
H18 | 0.4292 | 0.6490 | 0.2579 | 0.057* | |
C15 | 0.45009 (18) | 0.5339 (4) | 0.5600 (4) | 0.0560 (14) | |
H15 | 0.4557 | 0.5049 | 0.6360 | 0.067* | |
C16 | 0.47070 (18) | 0.6300 (4) | 0.5471 (5) | 0.0585 (14) | |
H16 | 0.4903 | 0.6657 | 0.6142 | 0.070* | |
C14 | 0.42124 (16) | 0.4803 (4) | 0.4608 (4) | 0.0481 (12) | |
H14 | 0.4071 | 0.4158 | 0.4697 | 0.058* | |
C17 | 0.46232 (17) | 0.6725 (4) | 0.4362 (5) | 0.0553 (13) | |
H17 | 0.4758 | 0.7384 | 0.4286 | 0.066* | |
C3 | 0.40278 (18) | 0.0613 (4) | −0.1356 (4) | 0.0492 (12) | |
H3 | 0.4037 | 0.0304 | −0.2062 | 0.059* | |
C2 | 0.43484 (18) | 0.0335 (4) | −0.0286 (5) | 0.0536 (13) | |
H2 | 0.4573 | −0.0177 | −0.0254 | 0.064* | |
N2 | 0.26250 (14) | 0.3552 (3) | −0.1220 (3) | 0.0471 (10) | |
N1 | 0.40084 (13) | 0.1526 (3) | 0.0690 (3) | 0.0393 (9) | |
C9 | 0.22292 (19) | 0.1715 (5) | −0.2508 (5) | 0.0588 (14) | |
H9 | 0.2095 | 0.1095 | −0.2936 | 0.071* | |
C8 | 0.26759 (17) | 0.1682 (4) | −0.1724 (4) | 0.0486 (12) | |
H8 | 0.2844 | 0.1038 | −0.1612 | 0.058* | |
C11 | 0.21949 (19) | 0.3548 (5) | −0.1966 (4) | 0.0586 (14) | |
H11 | 0.2024 | 0.4181 | −0.2030 | 0.070* | |
C10 | 0.19855 (19) | 0.2663 (5) | −0.2653 (4) | 0.0592 (14) | |
H10 | 0.1688 | 0.2710 | −0.3197 | 0.071* | |
Cl2 | 0.42609 (4) | 0.21756 (9) | 0.32609 (9) | 0.0506 (3) | |
O1 | 0.42303 (14) | 0.7870 (4) | 0.0930 (3) | 0.0663 (10) | |
H1W1 | 0.3956 (7) | 0.787 (6) | 0.069 (6) | 0.099* | |
H1W2 | 0.424 (2) | 0.783 (5) | 0.025 (3) | 0.099* | |
O2 | 0.5000 | 0.9028 (5) | 0.2500 | 0.087 (2) | |
H2W2 | 0.4803 (19) | 0.859 (4) | 0.213 (6) | 0.130* | |
H1A | 0.3997 (14) | 0.186 (3) | 0.126 (4) | 0.033 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Au1 | 0.04494 (14) | 0.05060 (13) | 0.04726 (13) | 0.01206 (9) | 0.01084 (10) | −0.00251 (9) |
S1 | 0.0458 (8) | 0.0439 (7) | 0.0735 (9) | 0.0109 (6) | 0.0064 (7) | −0.0198 (6) |
Cl1 | 0.0451 (8) | 0.0752 (9) | 0.0550 (8) | 0.0134 (6) | 0.0075 (7) | 0.0022 (6) |
C12 | 0.042 (3) | 0.032 (2) | 0.043 (2) | 0.001 (2) | 0.014 (2) | −0.005 (2) |
N3 | 0.041 (2) | 0.033 (2) | 0.0358 (19) | 0.0044 (16) | 0.0122 (18) | −0.0029 (16) |
N5 | 0.043 (3) | 0.0311 (19) | 0.047 (2) | 0.0033 (16) | 0.008 (2) | −0.0065 (17) |
N4 | 0.033 (2) | 0.037 (2) | 0.046 (2) | 0.0049 (16) | 0.0089 (19) | −0.0062 (17) |
C13 | 0.036 (3) | 0.038 (2) | 0.047 (3) | 0.004 (2) | 0.012 (2) | −0.004 (2) |
C5 | 0.040 (3) | 0.030 (2) | 0.036 (2) | −0.0010 (19) | 0.012 (2) | 0.0018 (19) |
C6 | 0.038 (3) | 0.033 (2) | 0.033 (2) | 0.0017 (18) | 0.013 (2) | 0.0008 (19) |
C7 | 0.041 (3) | 0.042 (2) | 0.032 (2) | 0.000 (2) | 0.016 (2) | 0.002 (2) |
C4 | 0.052 (3) | 0.040 (2) | 0.037 (2) | 0.005 (2) | 0.015 (2) | −0.002 (2) |
C1 | 0.050 (3) | 0.040 (3) | 0.047 (3) | 0.008 (2) | 0.007 (3) | 0.003 (2) |
C18 | 0.046 (3) | 0.043 (3) | 0.050 (3) | 0.004 (2) | 0.014 (3) | 0.003 (2) |
C15 | 0.056 (4) | 0.066 (3) | 0.044 (3) | 0.002 (3) | 0.015 (3) | −0.008 (3) |
C16 | 0.040 (3) | 0.066 (3) | 0.060 (3) | 0.000 (3) | 0.006 (3) | −0.023 (3) |
C14 | 0.045 (3) | 0.050 (3) | 0.052 (3) | 0.000 (2) | 0.019 (3) | 0.001 (2) |
C17 | 0.046 (3) | 0.041 (3) | 0.075 (4) | −0.005 (2) | 0.016 (3) | −0.012 (3) |
C3 | 0.056 (3) | 0.043 (3) | 0.050 (3) | 0.003 (2) | 0.020 (3) | −0.012 (2) |
C2 | 0.053 (3) | 0.044 (3) | 0.069 (4) | 0.011 (2) | 0.027 (3) | −0.003 (3) |
N2 | 0.043 (3) | 0.054 (2) | 0.040 (2) | 0.0091 (19) | 0.008 (2) | 0.0055 (18) |
N1 | 0.044 (3) | 0.033 (2) | 0.037 (2) | 0.0027 (17) | 0.010 (2) | −0.0038 (18) |
C9 | 0.045 (3) | 0.073 (4) | 0.054 (3) | −0.024 (3) | 0.012 (3) | −0.006 (3) |
C8 | 0.045 (3) | 0.050 (3) | 0.051 (3) | −0.006 (2) | 0.016 (3) | −0.001 (2) |
C11 | 0.048 (4) | 0.076 (4) | 0.047 (3) | 0.013 (3) | 0.009 (3) | 0.008 (3) |
C10 | 0.041 (3) | 0.088 (4) | 0.044 (3) | −0.006 (3) | 0.009 (3) | −0.001 (3) |
Cl2 | 0.0610 (9) | 0.0450 (6) | 0.0386 (6) | −0.0022 (6) | 0.0080 (6) | 0.0000 (5) |
O1 | 0.065 (3) | 0.079 (2) | 0.051 (2) | 0.002 (2) | 0.015 (2) | 0.003 (2) |
O2 | 0.077 (5) | 0.064 (4) | 0.092 (5) | 0.000 | −0.004 (4) | 0.000 |
Au1—S1 | 2.2515 (14) | C18—H18 | 0.9300 |
Au1—Cl1 | 2.2725 (14) | C15—C16 | 1.376 (7) |
S1—C12 | 1.713 (4) | C15—C14 | 1.377 (6) |
C12—N5 | 1.309 (5) | C15—H15 | 0.9300 |
C12—N4 | 1.351 (5) | C16—C17 | 1.357 (7) |
N3—C6 | 1.290 (5) | C16—H16 | 0.9300 |
N3—N4 | 1.353 (5) | C14—H14 | 0.9300 |
N5—C13 | 1.436 (5) | C17—H17 | 0.9300 |
N5—H5A | 0.8600 | C3—C2 | 1.362 (7) |
N4—H4A | 0.8600 | C3—H3 | 0.9300 |
C13—C18 | 1.383 (6) | C2—H2 | 0.9300 |
C13—C14 | 1.391 (6) | N2—C11 | 1.325 (6) |
C5—N1 | 1.349 (5) | N1—H1A | 0.80 (4) |
C5—C4 | 1.375 (6) | C9—C10 | 1.366 (7) |
C5—C6 | 1.485 (6) | C9—C8 | 1.381 (7) |
C6—C7 | 1.473 (6) | C9—H9 | 0.9300 |
C7—N2 | 1.364 (5) | C8—H8 | 0.9300 |
C7—C8 | 1.378 (6) | C11—C10 | 1.380 (7) |
C4—C3 | 1.384 (6) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C10—H10 | 0.9300 |
C1—N1 | 1.332 (6) | O1—H1W1 | 0.80 (2) |
C1—C2 | 1.361 (7) | O1—H1W2 | 0.813 (19) |
C1—H1 | 0.9300 | O2—H2W2 | 0.82 (2) |
C18—C17 | 1.390 (6) | ||
S1—Au1—Cl1 | 174.23 (5) | C16—C15—H15 | 119.9 |
C12—S1—Au1 | 105.72 (16) | C14—C15—H15 | 119.9 |
N5—C12—N4 | 117.8 (4) | C17—C16—C15 | 119.8 (5) |
N5—C12—S1 | 122.3 (3) | C17—C16—H16 | 120.1 |
N4—C12—S1 | 119.8 (3) | C15—C16—H16 | 120.1 |
C6—N3—N4 | 119.6 (4) | C15—C14—C13 | 119.5 (5) |
C12—N5—C13 | 126.6 (4) | C15—C14—H14 | 120.2 |
C12—N5—H5A | 116.7 | C13—C14—H14 | 120.2 |
C13—N5—H5A | 116.7 | C16—C17—C18 | 121.7 (5) |
C12—N4—N3 | 118.5 (4) | C16—C17—H17 | 119.2 |
C12—N4—H4A | 120.7 | C18—C17—H17 | 119.2 |
N3—N4—H4A | 120.7 | C2—C3—C4 | 119.9 (5) |
C18—C13—C14 | 120.5 (4) | C2—C3—H3 | 120.1 |
C18—C13—N5 | 121.6 (4) | C4—C3—H3 | 120.1 |
C14—C13—N5 | 117.7 (4) | C1—C2—C3 | 119.4 (5) |
N1—C5—C4 | 118.1 (4) | C1—C2—H2 | 120.3 |
N1—C5—C6 | 116.9 (4) | C3—C2—H2 | 120.3 |
C4—C5—C6 | 124.9 (4) | C11—N2—C7 | 117.6 (4) |
N3—C6—C7 | 128.7 (4) | C1—N1—C5 | 122.8 (4) |
N3—C6—C5 | 111.9 (4) | C1—N1—H1A | 124 (3) |
C7—C6—C5 | 119.4 (4) | C5—N1—H1A | 113 (3) |
N2—C7—C8 | 121.4 (4) | C10—C9—C8 | 119.7 (5) |
N2—C7—C6 | 115.7 (4) | C10—C9—H9 | 120.2 |
C8—C7—C6 | 122.8 (4) | C8—C9—H9 | 120.2 |
C5—C4—C3 | 119.7 (4) | C7—C8—C9 | 119.2 (5) |
C5—C4—H4 | 120.1 | C7—C8—H8 | 120.4 |
C3—C4—H4 | 120.1 | C9—C8—H8 | 120.4 |
N1—C1—C2 | 120.0 (5) | N2—C11—C10 | 124.1 (5) |
N1—C1—H1 | 120.0 | N2—C11—H11 | 118.0 |
C2—C1—H1 | 120.0 | C10—C11—H11 | 118.0 |
C13—C18—C17 | 118.2 (5) | C9—C10—C11 | 117.9 (5) |
C13—C18—H18 | 120.9 | C9—C10—H10 | 121.1 |
C17—C18—H18 | 120.9 | C11—C10—H10 | 121.1 |
C16—C15—C14 | 120.3 (5) | H1W1—O1—H1W2 | 92 (6) |
Au1—S1—C12—N5 | −157.3 (4) | N5—C13—C18—C17 | −175.9 (4) |
Au1—S1—C12—N4 | 23.6 (4) | C14—C15—C16—C17 | 0.4 (8) |
N4—C12—N5—C13 | 176.7 (4) | C16—C15—C14—C13 | 0.7 (8) |
S1—C12—N5—C13 | −2.5 (7) | C18—C13—C14—C15 | −0.6 (7) |
N5—C12—N4—N3 | −12.1 (6) | N5—C13—C14—C15 | 175.0 (4) |
S1—C12—N4—N3 | 167.0 (3) | C15—C16—C17—C18 | −1.6 (8) |
C6—N3—N4—C12 | 177.8 (4) | C13—C18—C17—C16 | 1.6 (8) |
C12—N5—C13—C18 | −60.4 (7) | C5—C4—C3—C2 | −0.1 (8) |
C12—N5—C13—C14 | 124.1 (5) | N1—C1—C2—C3 | 1.7 (8) |
N4—N3—C6—C7 | −7.3 (6) | C4—C3—C2—C1 | −1.5 (8) |
N4—N3—C6—C5 | 173.0 (3) | C8—C7—N2—C11 | −1.7 (6) |
N1—C5—C6—N3 | 31.7 (5) | C6—C7—N2—C11 | −179.8 (4) |
C4—C5—C6—N3 | −143.8 (4) | C2—C1—N1—C5 | −0.2 (7) |
N1—C5—C6—C7 | −148.1 (4) | C4—C5—N1—C1 | −1.4 (7) |
C4—C5—C6—C7 | 36.4 (6) | C6—C5—N1—C1 | −177.2 (4) |
N3—C6—C7—N2 | 18.1 (6) | N2—C7—C8—C9 | 2.8 (7) |
C5—C6—C7—N2 | −162.1 (4) | C6—C7—C8—C9 | −179.2 (4) |
N3—C6—C7—C8 | −160.0 (4) | C10—C9—C8—C7 | −0.7 (7) |
C5—C6—C7—C8 | 19.7 (6) | C7—N2—C11—C10 | −1.6 (7) |
N1—C5—C4—C3 | 1.5 (7) | C8—C9—C10—C11 | −2.3 (8) |
C6—C5—C4—C3 | 176.9 (4) | N2—C11—C10—C9 | 3.6 (8) |
C14—C13—C18—C17 | −0.5 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5A···Cl2 | 0.86 | 2.46 | 3.246 (4) | 153 |
N4—H4A···N2 | 0.86 | 1.97 | 2.629 (5) | 133 |
N1—H1A···Cl2 | 0.80 (4) | 2.26 (4) | 2.989 (4) | 150 (4) |
O1—H1W1···Cl1i | 0.80 (2) | 2.70 (5) | 3.353 (4) | 140 (6) |
O1—H1W2···Cl2ii | 0.81 (2) | 2.39 (2) | 3.206 (4) | 177 (6) |
O2—H2W2···O1 | 0.82 (2) | 2.06 (3) | 2.855 (5) | 163 (7) |
Symmetry codes: (i) −x+1/2, −y+3/2, −z; (ii) x, −y+1, z−1/2. |
Acknowledgements
This work was supported by CNPq, FAPDF, Finatec and, DDP-UnB.
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