Skip to main content
Acta Crystallographica Section E: Crystallographic Communications logoLink to Acta Crystallographica Section E: Crystallographic Communications
. 2026 Jan 16;82(Pt 2):168–172. doi: 10.1107/S2056989026000228

Synthesis and structure of {methyl (Z)-2-[4-(di­meth­yl­amino)­benzyl­idene]hydrazine-1-carbodi­thio­ate-κ2N2,S}bis­(tri­phenyl­phosphine-κP)copper(I) nitrate carbon tetra­chloride monosolvate

Liji Muthirakalayil Abraham a, Banmankhraw Dkhar b, Amirthalingam Arunkumar a, Thangaraja Chinnathangavel c, Kolandaivelu Saminathan d, Marappan Velusamy b,*, Venugopal Rajendiran a,*
Editor: W T A Harrisone
PMCID: PMC12874262  PMID: 41657507

In the title compound, the carbon tetra­chloride solvent mol­ecule is presumed to have originated as an impurity in the chloro­form solvent used. In the extended structure, the cation and anion are linked by an N—H⋯O hydrogen bond. Along with electrostatic forces, C—H⋯N, C—H⋯S and C—H⋯O hydrogen bonds help to consolidate the crystal packing.

Keywords: copper(I), tri­phenyl­phosphine, distorted tetra­hedral geometry, crystal structure

Abstract

In the title compound, [Cu(C11H15N3S2){P(C6H5)3}2]NO3·CCl4, the carbon tetra­chloride solvent mol­ecule is presumed to have originated as an impurity in the chloro­form solvent used. The coordination environment around the copper(I) ion is a distorted CuNSP2 tetra­hedron, with a τ4 structural index of 0.844. In the extended structure, the cation and anion are linked by an N—H⋯O hydrogen bond. Along with electrostatic forces, C—H⋯N, C—H⋯S and C—H⋯O hydrogen bonds help to consolidate the crystal packing.

1. Chemical context

Copper(I) complexes exhibit broad applications across medicinal chemistry (Papazoglou et al., 2014), materials science (Hei & Li, 2021), and catalysis (Egbert et al., 2013). Elucidating their structural features provides valuable insights for the innovative design of further copper(I) complexes, thereby enhancing their structure–activity relationships.1.

Copper(I) complexes bearing nitro­gen and sulfur donor ligands are of significant inter­est owing to the presence of this metal in the active sites of hydrogenases, carbon monoxide de­hydrogenases, and blue copper proteins. Complexes of copper(I) with methyl (Z)-2-(4-(di­methyl­amino)­benzyl­idene)hydrazine-1-carbodi­thio­ate ligands and their BSA binding properties have been reported in the literature (Malakar et al., 2023). Such copper(I) species are generally obtained by reacting methyl (Z)-2-(4-(di­methyl­amino)­benzyl­idene)hydrazine-1-carbodi­thio­ate or its derivatives with appropriate copper(I) precursors. In this context, the present work reports the synthesis and single-crystal X-ray characterization of the title mononuclear mixed-ligand copper(I) complex [Cu(C11H15N3S2){P(C6H5)3}2]NO3·CCl4 (I) or [Cu(NS)(PPh3)2]NO3·CCl4, where NS denotes the methyl (Z)-2-(4-(di­methyl­amino)­benzyl­idene)hydrazine-1-carbodi­thio­ate chel­ating ligand and PPh3 represents the tri­phenyl­phosphine co-ligand.

2. Structural commentary

Compound (I) crystallizes in the monoclinic space group P21/n, with one cation, one anion and one disordered CCl4 solvent mol­ecule in the asymmetric unit (Fig. 1). The CuI atom is bound to an azomethine nitro­gen atom and a sulfur atom from the C11H15N3S2 ligand, generating a five-membered chelate ring, in addition to phospho­rous coordination from two tri­phenyl­phosphine ligands. The Cu—N1 bond distance [2.112 (3) Å] is substanti­ally shorter than the Cu—S1 distance [2.3599 (11) Å], which is consistent with previously reported complexes containing analogous donor sets (Malakar et al., 2023). The bite angle of the di­thio­carbazate fragment, N1—Cu—S1 [84.80 (10)°], is significantly narrower than the bond angles involving the phosphine donors, P1—Cu—P2 [125.29 (4)°], reflecting trends observed in related CuI systems incorporating such coordination motifs (Pathaw et al., 2021). The remaining angles in the coordination sphere, namely N1—Cu—P2 [110.95 (9)°], N1—Cu—P1 [115.78 (8)°], S1—Cu—P2 [109.19 (3)°], and S1—Cu—P1 [101.91 (4)°] lie between these two extremes, reflecting the geometric adjustments required to accommodate different donor atoms and steric constraints around the CuI centre. The notably wider P1—Cu—P2 bond angle can be ascribed to the steric bulk and spatial demands of the two tri­phenyl­phosphine ligands, as observed in CuI complexes containing similar types of phosphine ligands (Messmer & Palenik, 2011). The bite angle of the N2—Cu1—S1 chelate ring is intrinsically constrained by the five-membered di­thio­carbazate ring, forcing a much smaller angle than the ideal tetra­hedral value. Overall, these angular distortions are a direct consequence of the competing electronic and steric influences within the coordination sphere, leading to the observed deviation from perfect tetra­hedral geometry. This is reflected in the four-coordinate structural index (τ4) of 0.844 [τ4 = (360° – (α + β))/141°] where α and β represent the two predominant θ angles in the four-coordinate complex (Yang et al., 2007): τ4 is unity and zero for perfect tetra­hedral and square planar geometries, respectively).

Figure 1.

Figure 1

The mol­ecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. H atoms are omitted for clarity.

Even though (I) was synthesized using chloro­form, the single-crystal X-ray structure revealed the presence of included carbon tetra­chloride (CCl4) mol­ecules. This can arise as commercial chloro­form often contains trace amounts of CCl4 as a stabilizer or residual impurity from industrial production. These minor amounts of solvate can crystallize during slow evaporation and be incorporated in the crystal. As a result of the weak van der Waals inter­actions, the CCl4 mol­ecules occupy voids in the crystal rather than coordinating to the metal centre (Huber et al., 1978).

3. Supra­molecular features

In the crystal, an N—H⋯O bond (Table 1) links the cation with the anion. The packing in the extended structure of (I) is consolidated by C—H⋯N, C—H⋯S and C—H⋯O inter­actions. All of the hydrogen-to-acceptor distances are less than 2.9 Å, and the donor-to-acceptor distances are less than 3.5 Å. Moreover, all of the hydrogen-bonding inter­actions exhibit D—H⋯A bond angles greater than 130°. The complete inter­action details are illustrated in the packing diagram of the compound shown in Fig. 2.

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2A⋯O2i 0.82 1.96 2.754 (5) 163
C2—H2⋯N1 0.93 2.55 3.391 (5) 151
C36—H36⋯S1 0.93 2.87 3.758 (5) 160
C37—H37⋯O2i 0.93 2.66 3.384 (5) 135
C47—H47A⋯O2 0.96 2.52 3.322 (6) 141

Symmetry code: (i) Inline graphic.

Figure 2.

Figure 2

The crystal packing of (I) with the N—H⋯O hydrogen bonds shown as blue dashed lines.

4. Hirshfeld Surface Analysis

Hirshfeld surface analysis was carried out using the Crystal Explorer 21.5 software package. The surfaces were generated over dnorm and two-dimensional fingerprint plots were obtained to qu­antify the directional inter­molecular inter­actions along with other atom-to-atom contacts. Fig. 3(a) and (b) show the Hirshfeld surfaces mapped over di and dnorm, respectively. The dark-red spots indicate the presence of close contacts between atoms, while the green regions represent weak contacts. The blue regions, which occupy the majority of the surface, indicate the absence of close contacts in the structure. In Fig. 3(b), hydrogen-bond inter­actions are represented by red dotted lines, whereas other atom-to-atom inter­actions are represented by blue dotted lines.

Figure 3.

Figure 3

Hirshfeld surfaces for (I); (a) di plot; (b) dnorm plot.

According to the two-dimensional fingerprint plots for (I) (Fig. 4), the H⋯H contacts make the largest contribution (61.4%) to the total Hirshfeld surface at a distance range of de + di ≃ 1.9 Å. Similarly, the C⋯H, O⋯H, S⋯H, C⋯C, N⋯H, and S⋯S inter­actions contribute 9.2%, 5.6%, 2.2%, 1.3%, 0.8%, and 0.4%, respectively.

Figure 4.

Figure 4

Two-dimensional fingerprint plots for (I); (a) all inter­actions and delineated into (b) H⋯H; (c) C⋯H/H⋯C; (d) O⋯H/H⋯O; (e) S⋯H/H⋯S; (f) C⋯C; (g) N⋯H/H⋯N; (h) S⋯S.

5. Database survey

A SciFinder structure-similarity search for CuI complexes bearing N,S-bidentate hydrazine-derived carbodi­thio­ate ligands in combination with tri­phenyl­phosphine donors revealed a small but significant group of structurally related systems. Early studies by Bianchini and co-workers explored the reactivity of bis­(tri­phenyl­phosphine)copper(I) species toward heterocumulenes such as CO2, COS, CS2, and phenyl iso­thio­cyanate, establishing that CuI centres supported by phosphines and sulfur-bearing ligands favour distorted tetra­hedral coordination and readily engage in S-based bond formation. The Cu—S distances vary from 2.10–2.35 Å for monodentate thiol­ates to 2.40–2.48 Å in chelating di­thiol­ate environments, while the Cu—P distances lie near 2.27 Å (Bianchini et al., 1983, 2002a,b). Borate-anchored CuI–phosphine complexes were reported by Lobbia et al. (1997) in which the Cu atom is coordinated to one phosphine and three pyrazolyl nitro­gen atoms in a distorted tetra­hedral environment. The N—Cu—P angles fall in the range 120.8 (1)–130.3 (1)°, and the N—Cu—N angles between 87.5 (1) and 90.8 (1)°, indicating that steric effects from the bulky PCy3 ligand significantly influence the coordination geometry. Complementary insight into the structural variability of phosphine–supported Cu(I) environments was provided by Bowmaker et al. (2002), who characterised three-coordinate tri­cyclo­hexyl­phosphine complexes, which crystallise in several polymorphic forms but maintain Cu—P distances in the 2.20–2.29 Å range and exhibit comparable P—Cu—P angles, and acyl­pyrazolo­nate bis­(phosphine) derivatives were described by Marchetti et al., (2000) and Eller & Kubas, (2002), who demonstrated that sulfur dioxide binding to CuI phosphine thiol­ate systems stabilizes unusual S- and Se-coordinated adducts, which further expanded the structural space, confirming that phosphine steric effects and ancillary ligand denticity modulate tetra­hedral versus pseudo-trigonal coordination. The adaptability of CuI coordination spheres in the presence of mixed N- and S-donors was additionally illustrated in phenanthroline-containing systems (Mutrofin et al., 2008; Pettinari et al., 1996) who reported phosphine-stabilized CuI–pyrazole salts that display diverse supra­molecular assemblies through hydrogen-bonding inter­actions. Across this literature landscape, κ2-N,S chelation in combination with monodentate phosphine donors emerges as a recurring theme. Several copper(I) and copper(II) systems with tri­cyclo­hexyl- or tri­phenyl­phosphine donors were reported, as well as analogous Ni, Pd, Pt, Ag, and Ru complexes. Notably, nitrate-bound tri­cyclo­hexyl­phosphine copper complexes and thiol­ate-bridged CuI–phosphine derivatives exhibit similar coordination features. However, no previous report describes a CuI system incorporating a methyl-substituted (Z)-hydrazine-1-carbodi­thio­ate ligand combined with tri­phenyl­phosphine and nitrate, confirming the novelty of the present structure.

6. Synthesis and crystallization

To a 20 ml chloro­form solution of the metal precursor [Cu(PPh3)2NO3] (0.325 g, 0.500 mmol), the ligand methyl (Z)-2-(4-(di­methyl­amino)­benzyl­idene)hydrazine-1-carbodi­thio­ate (0.126 g, 0.500 mmol) was added and stirred at room temperature for 12 h. The solution was then evaporated, and the desired complex was precipitated by diethyl ether (40 ml) and dried under vacuum. The obtained product was then recrystallized from chloro­form solution by slow evaporation to give yellow needles of (I). Yield: 65%.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C).

Table 2. Experimental details.

Crystal data
Chemical formula [Cu(C11H15N3S2)(C18H15P)2]NO3·CCl4
M r 1057.28
Crystal system, space group Monoclinic, P21/n
Temperature (K) 293
a, b, c (Å) 10.8364 (18), 22.358 (4), 20.107 (4)
β (°) 98.146 (7)
V3) 4822.4 (16)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.87
Crystal size (mm) 0.30 × 0.22 × 0.20
 
Data collection
Diffractometer Bruker D8 VENTURE CCD
Absorption correction Multi-scan (SADABS; Krause et al., 2015)
Tmin, Tmax 0.780, 0.845
No. of measured, independent and observed [I > 2σ(I)] reflections 85779, 8478, 6143
R int 0.097
(sin θ/λ)max−1) 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.168, 1.04
No. of reflections 8478
No. of parameters 590
No. of restraints 52
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.57, −0.91

Computer programs: APEX3 and SAINT), SHELXT2018/2 (Sheldrick, 2015a), SHELXL2019/2 (Sheldrick, 2015b), Mercury (Macrae et al., 2020) and publCIF(Westrip, 2010).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989026000228/hb8181sup1.cif

e-82-00168-sup1.cif (3.1MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026000228/hb8181Isup2.hkl

e-82-00168-Isup2.hkl (673.2KB, hkl)

CCDC reference: 2482415

Additional supporting information: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

{Methyl (Z)-2-[4-(dimethylamino)benzylidene]hydrazine-1-carbodithioate-κ2N2,S}bis(triphenylphosphine-κP)copper(I) nitrate carbon tetrachloride monosolvate . Crystal data

[Cu(C11H15N3S2)(C18H15P)2]NO3·CCl4 F(000) = 2176
Mr = 1057.28 Dx = 1.456 Mg m3
Monoclinic, P21/n Mo Kα radiation, λ = 0.71073 Å
a = 10.8364 (18) Å Cell parameters from 8478 reflections
b = 22.358 (4) Å θ = 2.0–25.0°
c = 20.107 (4) Å µ = 0.87 mm1
β = 98.146 (7)° T = 293 K
V = 4822.4 (16) Å3 Needle, yellow
Z = 4 0.30 × 0.22 × 0.20 mm

{Methyl (Z)-2-[4-(dimethylamino)benzylidene]hydrazine-1-carbodithioate-κ2N2,S}bis(triphenylphosphine-κP)copper(I) nitrate carbon tetrachloride monosolvate . Data collection

Bruker D8 VENTURE CCD diffractometer 6143 reflections with I > 2σ(I)
ω scans Rint = 0.097
Absorption correction: multi-scan (SADABS; Krause et al., 2015) θmax = 25.0°, θmin = 2.0°
Tmin = 0.780, Tmax = 0.845 h = −12→12
85779 measured reflections k = −26→26
8478 independent reflections l = −23→23

{Methyl (Z)-2-[4-(dimethylamino)benzylidene]hydrazine-1-carbodithioate-κ2N2,S}bis(triphenylphosphine-κP)copper(I) nitrate carbon tetrachloride monosolvate . Refinement

Refinement on F2 Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.055 w = 1/[σ2(Fo2) + (0.0965P)2 + 2.9941P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.168 (Δ/σ)max = 0.002
S = 1.04 Δρmax = 0.57 e Å3
8478 reflections Δρmin = −0.91 e Å3
590 parameters Extinction correction: SHELXL-2019/2 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
52 restraints Extinction coefficient: 0.0013 (3)
Primary atom site location: dual

{Methyl (Z)-2-[4-(dimethylamino)benzylidene]hydrazine-1-carbodithioate-κ2N2,S}bis(triphenylphosphine-κP)copper(I) nitrate carbon tetrachloride monosolvate . Special details

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.

{Methyl (Z)-2-[4-(dimethylamino)benzylidene]hydrazine-1-carbodithioate-κ2N2,S}bis(triphenylphosphine-κP)copper(I) nitrate carbon tetrachloride monosolvate . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
C1 3.0510 (3) 0.13767 (17) 0.68718 (18) 0.0465 (9)
C2 2.9398 (4) 0.1173 (2) 0.7063 (2) 0.0553 (10)
H2 2.867151 0.139233 0.694544 0.066*
C3 2.9357 (5) 0.0647 (2) 0.7424 (2) 0.0726 (14)
H3 2.860989 0.051497 0.754977 0.087*
C4 3.0431 (5) 0.0325 (2) 0.7595 (3) 0.0788 (15)
H4 3.040878 −0.002617 0.784103 0.095*
C5 3.1524 (5) 0.0510 (2) 0.7411 (3) 0.0753 (14)
H5 3.224366 0.028597 0.753176 0.090*
C6 3.1578 (4) 0.1033 (2) 0.7043 (2) 0.0628 (12)
H6 3.232832 0.115400 0.691075 0.075*
C7 3.1742 (3) 0.19743 (17) 0.58957 (18) 0.0427 (9)
C8 3.1793 (4) 0.1447 (2) 0.5522 (2) 0.0593 (11)
H8 3.120031 0.114950 0.554549 0.071*
C9 3.2713 (4) 0.1363 (2) 0.5120 (2) 0.0665 (12)
H9 3.275139 0.100776 0.488417 0.080*
C10 3.3567 (4) 0.1805 (3) 0.5071 (2) 0.0707 (13)
H10 3.418250 0.174973 0.479791 0.085*
C11 3.3520 (4) 0.2327 (2) 0.5420 (3) 0.0702 (13)
H11 3.409354 0.262965 0.537876 0.084*
C12 3.2604 (4) 0.2407 (2) 0.5842 (2) 0.0565 (11)
H12 3.258766 0.275928 0.608712 0.068*
C13 3.1098 (3) 0.26363 (19) 0.70024 (19) 0.0485 (10)
C14 3.1983 (4) 0.2512 (2) 0.7557 (2) 0.0629 (12)
H14 3.225773 0.212115 0.763530 0.075*
C15 3.2451 (5) 0.2949 (3) 0.7986 (3) 0.0864 (17)
H15 3.305382 0.285752 0.834819 0.104*
C16 3.2045 (6) 0.3521 (4) 0.7888 (3) 0.098 (2)
H16 3.236378 0.381759 0.818852 0.118*
C17 3.1166 (5) 0.3669 (3) 0.7349 (3) 0.0907 (18)
H17 3.089342 0.406184 0.728159 0.109*
C18 3.0693 (4) 0.3218 (2) 0.6906 (2) 0.0657 (12)
H18 3.009593 0.331144 0.654129 0.079*
C19 2.9079 (3) 0.31867 (17) 0.44612 (18) 0.0440 (9)
C20 3.0136 (4) 0.2842 (2) 0.4469 (2) 0.0606 (12)
H20 3.032798 0.255689 0.480405 0.073*
C21 3.0921 (5) 0.2914 (2) 0.3982 (2) 0.0740 (14)
H21 3.162242 0.267328 0.398696 0.089*
C22 3.0651 (5) 0.3343 (2) 0.3496 (2) 0.0718 (13)
H22 3.118750 0.340393 0.317991 0.086*
C23 2.9598 (4) 0.3679 (2) 0.3474 (2) 0.0661 (12)
H23 2.941286 0.396449 0.313889 0.079*
C24 2.8801 (4) 0.35993 (19) 0.3947 (2) 0.0590 (11)
H24 2.807351 0.382426 0.392042 0.071*
C25 2.8157 (4) 0.37910 (17) 0.55577 (19) 0.0492 (10)
C26 2.9089 (5) 0.4208 (2) 0.5522 (3) 0.0719 (13)
H26 2.967071 0.414072 0.523193 0.086*
C27 2.9176 (6) 0.4719 (2) 0.5906 (3) 0.0962 (19)
H27 2.982037 0.498936 0.587929 0.115*
C28 2.8308 (7) 0.4832 (3) 0.6330 (3) 0.098 (2)
H28 2.835634 0.517911 0.658740 0.118*
C29 2.7377 (6) 0.4428 (2) 0.6367 (3) 0.0832 (16)
H29 2.678614 0.450020 0.665011 0.100*
C30 2.7305 (5) 0.3912 (2) 0.5987 (2) 0.0627 (12)
H30 2.666758 0.363976 0.602099 0.075*
C31 2.6534 (3) 0.30880 (18) 0.46096 (18) 0.0467 (9)
C32 2.5847 (5) 0.3598 (2) 0.4473 (3) 0.0778 (15)
H32 2.610620 0.395616 0.468235 0.093*
C33 2.4753 (5) 0.3572 (3) 0.4016 (3) 0.0947 (19)
H33 2.428118 0.391707 0.392422 0.114*
C34 2.4358 (5) 0.3051 (3) 0.3702 (3) 0.0833 (17)
H34 2.363814 0.304342 0.338950 0.100*
C35 2.5023 (5) 0.2553 (3) 0.3849 (2) 0.0790 (15)
H35 2.474493 0.219539 0.364303 0.095*
C36 2.6122 (4) 0.2554 (2) 0.4304 (2) 0.0595 (11)
H36 2.657198 0.220296 0.440074 0.071*
C37 2.6272 (4) 0.20298 (18) 0.6466 (2) 0.0503 (10)
H37 2.553203 0.181747 0.645880 0.060*
C38 2.6472 (3) 0.25264 (19) 0.69251 (19) 0.0491 (10)
C39 2.7613 (4) 0.28038 (19) 0.7111 (2) 0.0540 (10)
H39 2.830430 0.266560 0.693121 0.065*
C40 2.7754 (4) 0.3271 (2) 0.7548 (2) 0.0591 (11)
H40 2.853898 0.344107 0.766161 0.071*
C41 2.6747 (4) 0.3504 (2) 0.7831 (2) 0.0616 (11)
C42 2.5603 (4) 0.3218 (2) 0.7659 (3) 0.0718 (13)
H42 2.491220 0.335163 0.784262 0.086*
C43 2.5479 (4) 0.2746 (2) 0.7227 (3) 0.0689 (13)
H43 2.470375 0.256280 0.712970 0.083*
C44 2.8032 (6) 0.4290 (3) 0.8405 (3) 0.0986 (19)
H44A 2.794740 0.461341 0.870926 0.148*
H44B 2.865745 0.401674 0.860798 0.148*
H44C 2.827278 0.444588 0.799718 0.148*
C45 2.5846 (6) 0.4168 (3) 0.8588 (3) 0.1000 (19)
H45A 2.608369 0.450975 0.886641 0.150*
H45B 2.514892 0.427070 0.825787 0.150*
H45C 2.561684 0.384591 0.886145 0.150*
C46 2.7232 (4) 0.11030 (17) 0.5255 (2) 0.0520 (10)
C47 2.7519 (6) 0.0203 (2) 0.4333 (3) 0.0858 (17)
H47A 2.719630 −0.015909 0.411752 0.129*
H47B 2.756371 0.050690 0.400056 0.129*
H47C 2.833672 0.012977 0.457141 0.129*
C48 3.3194 (9) 0.4272 (3) 0.5651 (4) 0.226 (6)
N1 2.7024 (3) 0.18535 (14) 0.60652 (16) 0.0451 (8)
N2 2.6641 (3) 0.13278 (15) 0.57286 (17) 0.0515 (8)
H2A 2.612437 0.108611 0.582327 0.077*
N3 3.5183 (3) 0.05500 (16) 0.68568 (19) 0.0572 (9)
N4 2.6876 (4) 0.3986 (2) 0.8257 (2) 0.0806 (12)
O1 3.6175 (3) 0.07496 (16) 0.71350 (18) 0.0825 (10)
O2 3.4847 (3) 0.06823 (18) 0.62581 (19) 0.0957 (13)
O3 3.4555 (4) 0.02164 (18) 0.71447 (19) 0.0932 (12)
P1 3.04707 (8) 0.20709 (4) 0.63954 (5) 0.0408 (2)
P2 2.80883 (9) 0.30789 (4) 0.51150 (5) 0.0408 (3)
S1 2.84891 (10) 0.14034 (5) 0.49953 (5) 0.0546 (3)
S2 2.65109 (13) 0.04460 (6) 0.49112 (7) 0.0821 (4)
Cu 2.86077 (4) 0.22336 (2) 0.57262 (2) 0.04075 (17)
Cl1 3.2286 (4) 0.39592 (19) 0.4997 (3) 0.1015 (9) 0.5
Cl1' 3.4001 (3) 0.3864 (2) 0.6323 (2) 0.1015 (9) 0.5
Cl2 3.4040 (14) 0.4819 (4) 0.5416 (7) 0.360 (7) 0.5
Cl2' 3.3799 (15) 0.3925 (4) 0.6356 (6) 0.360 (7) 0.5
Cl3 3.2687 (9) 0.4928 (3) 0.5874 (4) 0.215 (3) 0.5
Cl3' 3.2528 (9) 0.3816 (3) 0.5083 (4) 0.215 (3) 0.5
Cl4 3.2245 (9) 0.4611 (8) 0.6087 (8) 0.380 (7) 0.5
Cl4' 3.4426 (10) 0.4662 (7) 0.5482 (10) 0.380 (7) 0.5

{Methyl (Z)-2-[4-(dimethylamino)benzylidene]hydrazine-1-carbodithioate-κ2N2,S}bis(triphenylphosphine-κP)copper(I) nitrate carbon tetrachloride monosolvate . Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.051 (2) 0.049 (2) 0.040 (2) −0.0006 (18) 0.0054 (16) 0.0050 (17)
C2 0.051 (2) 0.060 (3) 0.055 (2) 0.000 (2) 0.0083 (19) 0.013 (2)
C3 0.069 (3) 0.077 (3) 0.072 (3) −0.011 (3) 0.011 (2) 0.029 (3)
C4 0.083 (3) 0.070 (3) 0.082 (4) −0.003 (3) 0.005 (3) 0.036 (3)
C5 0.070 (3) 0.070 (3) 0.084 (3) 0.014 (3) 0.001 (3) 0.026 (3)
C6 0.053 (2) 0.066 (3) 0.070 (3) 0.005 (2) 0.010 (2) 0.017 (2)
C7 0.0407 (19) 0.046 (2) 0.040 (2) 0.0007 (16) 0.0028 (15) 0.0044 (17)
C8 0.058 (2) 0.059 (3) 0.063 (3) −0.006 (2) 0.016 (2) −0.002 (2)
C9 0.069 (3) 0.069 (3) 0.066 (3) 0.011 (2) 0.025 (2) −0.007 (2)
C10 0.061 (3) 0.095 (4) 0.060 (3) 0.011 (3) 0.025 (2) 0.005 (3)
C11 0.054 (3) 0.086 (4) 0.074 (3) −0.015 (2) 0.020 (2) 0.011 (3)
C12 0.053 (2) 0.059 (3) 0.059 (3) −0.008 (2) 0.012 (2) −0.001 (2)
C13 0.0402 (19) 0.061 (3) 0.045 (2) −0.0083 (18) 0.0096 (17) −0.0076 (19)
C14 0.057 (2) 0.082 (3) 0.048 (2) −0.016 (2) 0.001 (2) −0.001 (2)
C15 0.076 (3) 0.129 (5) 0.052 (3) −0.033 (4) 0.002 (2) −0.015 (3)
C16 0.088 (4) 0.131 (6) 0.077 (4) −0.050 (4) 0.016 (3) −0.054 (4)
C17 0.089 (4) 0.073 (4) 0.113 (5) −0.019 (3) 0.024 (4) −0.037 (3)
C18 0.059 (3) 0.057 (3) 0.078 (3) −0.010 (2) 0.001 (2) −0.016 (2)
C19 0.048 (2) 0.042 (2) 0.042 (2) −0.0087 (17) 0.0058 (16) 0.0003 (17)
C20 0.054 (2) 0.074 (3) 0.055 (3) 0.005 (2) 0.009 (2) 0.015 (2)
C21 0.063 (3) 0.095 (4) 0.068 (3) 0.008 (3) 0.021 (2) 0.009 (3)
C22 0.070 (3) 0.095 (4) 0.054 (3) −0.012 (3) 0.023 (2) 0.005 (3)
C23 0.078 (3) 0.069 (3) 0.052 (3) −0.012 (3) 0.013 (2) 0.017 (2)
C24 0.066 (3) 0.057 (3) 0.055 (3) 0.003 (2) 0.012 (2) 0.016 (2)
C25 0.063 (2) 0.039 (2) 0.044 (2) 0.0020 (18) 0.0031 (19) 0.0011 (17)
C26 0.085 (3) 0.057 (3) 0.075 (3) −0.014 (2) 0.017 (3) −0.012 (2)
C27 0.116 (5) 0.061 (4) 0.110 (5) −0.030 (3) 0.009 (4) −0.021 (3)
C28 0.155 (6) 0.056 (4) 0.078 (4) 0.001 (4) −0.001 (4) −0.018 (3)
C29 0.127 (5) 0.066 (4) 0.062 (3) 0.017 (3) 0.027 (3) −0.004 (3)
C30 0.083 (3) 0.052 (3) 0.055 (3) 0.006 (2) 0.018 (2) −0.001 (2)
C31 0.042 (2) 0.060 (3) 0.039 (2) 0.0004 (18) 0.0079 (16) 0.0065 (19)
C32 0.078 (3) 0.076 (4) 0.074 (3) 0.018 (3) −0.009 (3) 0.005 (3)
C33 0.072 (3) 0.123 (5) 0.083 (4) 0.035 (3) −0.009 (3) 0.022 (4)
C34 0.049 (3) 0.139 (6) 0.059 (3) −0.002 (3) −0.001 (2) 0.012 (3)
C35 0.064 (3) 0.113 (5) 0.058 (3) −0.027 (3) 0.000 (2) −0.005 (3)
C36 0.054 (2) 0.070 (3) 0.052 (2) −0.013 (2) 0.0005 (19) 0.000 (2)
C37 0.044 (2) 0.050 (2) 0.057 (2) −0.0090 (18) 0.0055 (19) 0.013 (2)
C38 0.047 (2) 0.052 (2) 0.050 (2) 0.0038 (19) 0.0126 (18) 0.012 (2)
C39 0.047 (2) 0.063 (3) 0.054 (2) −0.0023 (19) 0.0130 (19) −0.002 (2)
C40 0.058 (3) 0.067 (3) 0.053 (3) −0.008 (2) 0.010 (2) −0.001 (2)
C41 0.077 (3) 0.059 (3) 0.051 (3) 0.008 (2) 0.018 (2) 0.009 (2)
C42 0.064 (3) 0.081 (4) 0.076 (3) 0.011 (3) 0.026 (2) −0.004 (3)
C43 0.048 (2) 0.081 (4) 0.080 (3) −0.004 (2) 0.021 (2) −0.001 (3)
C44 0.144 (6) 0.082 (4) 0.074 (4) −0.021 (4) 0.029 (4) −0.016 (3)
C45 0.116 (5) 0.107 (5) 0.079 (4) 0.029 (4) 0.020 (3) −0.019 (3)
C46 0.058 (2) 0.039 (2) 0.053 (2) −0.0109 (18) −0.012 (2) 0.0025 (18)
C47 0.134 (5) 0.054 (3) 0.069 (3) −0.031 (3) 0.013 (3) −0.015 (2)
C48 0.276 (14) 0.118 (8) 0.269 (14) −0.057 (9) −0.022 (12) −0.039 (9)
N1 0.0427 (17) 0.0447 (19) 0.0464 (18) −0.0082 (14) 0.0007 (14) 0.0075 (15)
N2 0.0520 (19) 0.045 (2) 0.056 (2) −0.0173 (15) 0.0019 (16) 0.0032 (16)
N3 0.058 (2) 0.054 (2) 0.061 (2) −0.0015 (18) 0.0158 (19) 0.0054 (18)
N4 0.100 (3) 0.074 (3) 0.073 (3) −0.001 (2) 0.030 (2) −0.013 (2)
O1 0.078 (2) 0.088 (3) 0.078 (2) −0.0154 (19) −0.0019 (18) 0.0061 (19)
O2 0.091 (2) 0.112 (3) 0.077 (2) −0.051 (2) −0.013 (2) 0.030 (2)
O3 0.091 (2) 0.104 (3) 0.090 (3) −0.022 (2) 0.032 (2) 0.021 (2)
P1 0.0396 (5) 0.0427 (6) 0.0395 (5) −0.0033 (4) 0.0035 (4) 0.0016 (4)
P2 0.0437 (5) 0.0386 (6) 0.0397 (5) −0.0037 (4) 0.0044 (4) 0.0024 (4)
S1 0.0611 (6) 0.0450 (6) 0.0580 (6) −0.0121 (5) 0.0096 (5) −0.0105 (5)
S2 0.0927 (9) 0.0565 (8) 0.0950 (10) −0.0351 (7) 0.0060 (8) −0.0151 (7)
Cu 0.0427 (3) 0.0374 (3) 0.0413 (3) −0.00711 (19) 0.00314 (19) 0.00170 (19)
Cl1 0.0810 (13) 0.091 (2) 0.125 (2) −0.0002 (12) −0.0107 (13) −0.0179 (16)
Cl1' 0.0810 (13) 0.091 (2) 0.125 (2) −0.0002 (12) −0.0107 (13) −0.0179 (16)
Cl2 0.654 (18) 0.123 (4) 0.265 (8) −0.131 (7) −0.071 (9) 0.054 (5)
Cl2' 0.654 (18) 0.123 (4) 0.265 (8) −0.131 (7) −0.071 (9) 0.054 (5)
Cl3 0.307 (7) 0.114 (3) 0.190 (4) 0.064 (3) −0.088 (4) −0.027 (3)
Cl3' 0.307 (7) 0.114 (3) 0.190 (4) 0.064 (3) −0.088 (4) −0.027 (3)
Cl4 0.179 (5) 0.483 (15) 0.499 (16) −0.046 (7) 0.113 (7) −0.183 (13)
Cl4' 0.179 (5) 0.483 (15) 0.499 (16) −0.046 (7) 0.113 (7) −0.183 (13)

{Methyl (Z)-2-[4-(dimethylamino)benzylidene]hydrazine-1-carbodithioate-κ2N2,S}bis(triphenylphosphine-κP)copper(I) nitrate carbon tetrachloride monosolvate . Geometric parameters (Å, º)

C1—C6 1.391 (6) C30—H30 0.9300
C1—C2 1.392 (5) C31—C32 1.367 (6)
C1—P1 1.821 (4) C31—C36 1.387 (6)
C2—C3 1.386 (6) C31—P2 1.840 (4)
C2—H2 0.9300 C32—C33 1.395 (7)
C3—C4 1.370 (7) C32—H32 0.9300
C3—H3 0.9300 C33—C34 1.364 (8)
C4—C5 1.356 (7) C33—H33 0.9300
C4—H4 0.9300 C34—C35 1.338 (8)
C5—C6 1.390 (6) C34—H34 0.9300
C5—H5 0.9300 C35—C36 1.395 (6)
C6—H6 0.9300 C35—H35 0.9300
C7—C12 1.360 (6) C36—H36 0.9300
C7—C8 1.404 (6) C37—N1 1.287 (5)
C7—P1 1.830 (4) C37—C38 1.440 (6)
C8—C9 1.382 (6) C37—H37 0.9300
C8—H8 0.9300 C38—C39 1.386 (5)
C9—C10 1.365 (7) C38—C43 1.398 (6)
C9—H9 0.9300 C39—C40 1.360 (6)
C10—C11 1.369 (7) C39—H39 0.9300
C10—H10 0.9300 C40—C41 1.400 (6)
C11—C12 1.405 (6) C40—H40 0.9300
C11—H11 0.9300 C41—N4 1.372 (6)
C12—H12 0.9300 C41—C42 1.395 (7)
C13—C18 1.379 (6) C42—C43 1.360 (7)
C13—C14 1.392 (5) C42—H42 0.9300
C13—P1 1.821 (4) C43—H43 0.9300
C14—C15 1.352 (7) C44—N4 1.419 (7)
C14—H14 0.9300 C44—H44A 0.9600
C15—C16 1.359 (9) C44—H44B 0.9600
C15—H15 0.9300 C44—H44C 0.9600
C16—C17 1.378 (9) C45—N4 1.438 (7)
C16—H16 0.9300 C45—H45A 0.9600
C17—C18 1.393 (7) C45—H45B 0.9600
C17—H17 0.9300 C45—H45C 0.9600
C18—H18 0.9300 C46—N2 1.320 (5)
C19—C20 1.378 (6) C46—S1 1.668 (4)
C19—C24 1.386 (5) C46—S2 1.759 (4)
C19—P2 1.827 (4) C47—S2 1.788 (6)
C20—C21 1.395 (6) C47—H47A 0.9600
C20—H20 0.9300 C47—H47B 0.9600
C21—C22 1.370 (7) C47—H47C 0.9600
C21—H21 0.9300 C48—Cl3' 1.622 (8)
C22—C23 1.362 (7) C48—Cl4 1.630 (10)
C22—H22 0.9300 C48—Cl2 1.639 (11)
C23—C24 1.384 (6) C48—Cl3 1.652 (10)
C23—H23 0.9300 C48—Cl2' 1.665 (10)
C24—H24 0.9300 C48—Cl4' 1.670 (10)
C25—C30 1.376 (6) C48—Cl1 1.680 (8)
C25—C26 1.384 (6) C48—Cl1' 1.757 (9)
C25—P2 1.821 (4) N1—N2 1.390 (4)
C26—C27 1.375 (7) N1—Cu 2.112 (3)
C26—H26 0.9300 N2—H2A 0.8200
C27—C28 1.380 (9) N3—O3 1.211 (5)
C27—H27 0.9300 N3—O1 1.223 (4)
C28—C29 1.365 (8) N3—O2 1.243 (5)
C28—H28 0.9300 P1—Cu 2.2911 (10)
C29—C30 1.380 (7) P2—Cu 2.2808 (11)
C29—H29 0.9300 S1—Cu 2.3599 (11)
C6—C1—C2 118.3 (4) C31—C32—C33 119.0 (5)
C6—C1—P1 123.8 (3) C31—C32—H32 120.5
C2—C1—P1 117.9 (3) C33—C32—H32 120.5
C3—C2—C1 121.1 (4) C34—C33—C32 121.5 (5)
C3—C2—H2 119.5 C34—C33—H33 119.3
C1—C2—H2 119.5 C32—C33—H33 119.3
C4—C3—C2 119.2 (4) C35—C34—C33 119.0 (5)
C4—C3—H3 120.4 C35—C34—H34 120.5
C2—C3—H3 120.4 C33—C34—H34 120.5
C5—C4—C3 121.0 (4) C34—C35—C36 121.7 (5)
C5—C4—H4 119.5 C34—C35—H35 119.1
C3—C4—H4 119.5 C36—C35—H35 119.1
C4—C5—C6 120.5 (4) C31—C36—C35 118.9 (5)
C4—C5—H5 119.8 C31—C36—H36 120.5
C6—C5—H5 119.8 C35—C36—H36 120.5
C5—C6—C1 120.0 (4) N1—C37—C38 125.9 (4)
C5—C6—H6 120.0 N1—C37—H37 117.1
C1—C6—H6 120.0 C38—C37—H37 117.1
C12—C7—C8 118.5 (4) C39—C38—C43 115.9 (4)
C12—C7—P1 122.6 (3) C39—C38—C37 124.4 (4)
C8—C7—P1 118.9 (3) C43—C38—C37 119.6 (4)
C9—C8—C7 120.8 (4) C40—C39—C38 122.2 (4)
C9—C8—H8 119.6 C40—C39—H39 118.9
C7—C8—H8 119.6 C38—C39—H39 118.9
C10—C9—C8 119.8 (5) C39—C40—C41 121.7 (4)
C10—C9—H9 120.1 C39—C40—H40 119.2
C8—C9—H9 120.1 C41—C40—H40 119.2
C9—C10—C11 120.3 (4) N4—C41—C42 121.6 (4)
C9—C10—H10 119.8 N4—C41—C40 121.9 (5)
C11—C10—H10 119.8 C42—C41—C40 116.5 (4)
C10—C11—C12 120.0 (4) C43—C42—C41 121.2 (4)
C10—C11—H11 120.0 C43—C42—H42 119.4
C12—C11—H11 120.0 C41—C42—H42 119.4
C7—C12—C11 120.6 (4) C42—C43—C38 122.5 (4)
C7—C12—H12 119.7 C42—C43—H43 118.8
C11—C12—H12 119.7 C38—C43—H43 118.8
C18—C13—C14 118.0 (4) N4—C44—H44A 109.5
C18—C13—P1 118.7 (3) N4—C44—H44B 109.5
C14—C13—P1 123.3 (4) H44A—C44—H44B 109.5
C15—C14—C13 121.3 (5) N4—C44—H44C 109.5
C15—C14—H14 119.3 H44A—C44—H44C 109.5
C13—C14—H14 119.3 H44B—C44—H44C 109.5
C14—C15—C16 120.2 (5) N4—C45—H45A 109.5
C14—C15—H15 119.9 N4—C45—H45B 109.5
C16—C15—H15 119.9 H45A—C45—H45B 109.5
C15—C16—C17 120.9 (5) N4—C45—H45C 109.5
C15—C16—H16 119.5 H45A—C45—H45C 109.5
C17—C16—H16 119.5 H45B—C45—H45C 109.5
C16—C17—C18 118.7 (6) N2—C46—S1 125.0 (3)
C16—C17—H17 120.7 N2—C46—S2 111.6 (3)
C18—C17—H17 120.7 S1—C46—S2 123.4 (3)
C13—C18—C17 120.8 (5) S2—C47—H47A 109.5
C13—C18—H18 119.6 S2—C47—H47B 109.5
C17—C18—H18 119.6 H47A—C47—H47B 109.5
C20—C19—C24 118.2 (4) S2—C47—H47C 109.5
C20—C19—P2 119.4 (3) H47A—C47—H47C 109.5
C24—C19—P2 122.4 (3) H47B—C47—H47C 109.5
C19—C20—C21 121.1 (4) Cl3'—C48—Cl3 128.2 (7)
C19—C20—H20 119.4 Cl2—C48—Cl2' 115.1 (8)
C21—C20—H20 119.4 Cl4—C48—Cl4' 116.8 (9)
C22—C21—C20 119.4 (5) Cl1—C48—Cl1' 124.0 (5)
C22—C21—H21 120.3 C37—N1—N2 113.1 (3)
C20—C21—H21 120.3 C37—N1—Cu 134.0 (3)
C23—C22—C21 120.1 (4) N2—N1—Cu 112.5 (2)
C23—C22—H22 119.9 C46—N2—N1 122.1 (3)
C21—C22—H22 119.9 C46—N2—H2A 109.5
C22—C23—C24 120.6 (4) N1—N2—H2A 127.7
C22—C23—H23 119.7 O3—N3—O1 121.5 (4)
C24—C23—H23 119.7 O3—N3—O2 120.1 (4)
C23—C24—C19 120.4 (4) O1—N3—O2 118.3 (4)
C23—C24—H24 119.8 C41—N4—C44 121.1 (4)
C19—C24—H24 119.8 C41—N4—C45 119.7 (5)
C30—C25—C26 117.4 (4) C44—N4—C45 119.2 (5)
C30—C25—P2 119.5 (3) C13—P1—C1 105.10 (18)
C26—C25—P2 122.9 (3) C13—P1—C7 102.20 (17)
C27—C26—C25 121.6 (5) C1—P1—C7 103.01 (18)
C27—C26—H26 119.2 C13—P1—Cu 119.84 (14)
C25—C26—H26 119.2 C1—P1—Cu 113.40 (12)
C26—C27—C28 120.0 (6) C7—P1—Cu 111.46 (12)
C26—C27—H27 120.0 C25—P2—C19 104.41 (18)
C28—C27—H27 120.0 C25—P2—C31 103.36 (18)
C29—C28—C27 119.1 (5) C19—P2—C31 100.75 (17)
C29—C28—H28 120.4 C25—P2—Cu 118.12 (13)
C27—C28—H28 120.4 C19—P2—Cu 111.82 (13)
C28—C29—C30 120.6 (5) C31—P2—Cu 116.33 (13)
C28—C29—H29 119.7 C46—S1—Cu 95.54 (16)
C30—C29—H29 119.7 C46—S2—C47 103.4 (2)
C25—C30—C29 121.4 (5) N1—Cu—P2 110.95 (9)
C25—C30—H30 119.3 N1—Cu—P1 115.78 (8)
C29—C30—H30 119.3 P2—Cu—P1 125.29 (4)
C32—C31—C36 119.8 (4) N1—Cu—S1 84.80 (10)
C32—C31—P2 123.3 (3) P2—Cu—S1 109.19 (4)
C36—C31—P2 116.5 (3) P1—Cu—S1 101.91 (4)
C6—C1—C2—C3 1.2 (6) N4—C41—C42—C43 178.9 (5)
P1—C1—C2—C3 179.8 (4) C40—C41—C42—C43 −1.3 (7)
C1—C2—C3—C4 −0.1 (7) C41—C42—C43—C38 −0.9 (8)
C2—C3—C4—C5 −0.5 (8) C39—C38—C43—C42 2.4 (7)
C3—C4—C5—C6 −0.1 (9) C37—C38—C43—C42 −179.2 (4)
C4—C5—C6—C1 1.2 (8) C38—C37—N1—N2 174.1 (3)
C2—C1—C6—C5 −1.8 (7) C38—C37—N1—Cu −13.9 (6)
P1—C1—C6—C5 179.7 (4) S1—C46—N2—N1 0.1 (5)
C12—C7—C8—C9 1.3 (6) S2—C46—N2—N1 −178.8 (2)
P1—C7—C8—C9 177.8 (3) C37—N1—N2—C46 174.2 (3)
C7—C8—C9—C10 −1.7 (7) Cu—N1—N2—C46 0.4 (4)
C8—C9—C10—C11 0.4 (7) C42—C41—N4—C44 −177.2 (5)
C9—C10—C11—C12 1.2 (7) C40—C41—N4—C44 3.0 (7)
C8—C7—C12—C11 0.2 (6) C42—C41—N4—C45 6.2 (7)
P1—C7—C12—C11 −176.1 (3) C40—C41—N4—C45 −173.5 (5)
C10—C11—C12—C7 −1.5 (7) C18—C13—P1—C1 −150.4 (3)
C18—C13—C14—C15 −1.1 (7) C14—C13—P1—C1 30.4 (4)
P1—C13—C14—C15 178.0 (4) C18—C13—P1—C7 102.3 (4)
C13—C14—C15—C16 1.3 (8) C14—C13—P1—C7 −76.8 (4)
C14—C15—C16—C17 −0.9 (9) C18—C13—P1—Cu −21.5 (4)
C15—C16—C17—C18 0.4 (9) C14—C13—P1—Cu 159.4 (3)
C14—C13—C18—C17 0.6 (7) C6—C1—P1—C13 −79.5 (4)
P1—C13—C18—C17 −178.6 (4) C2—C1—P1—C13 101.9 (3)
C16—C17—C18—C13 −0.3 (8) C6—C1—P1—C7 27.2 (4)
C24—C19—C20—C21 1.4 (6) C2—C1—P1—C7 −151.4 (3)
P2—C19—C20—C21 −179.5 (4) C6—C1—P1—Cu 147.8 (3)
C19—C20—C21—C22 1.3 (7) C2—C1—P1—Cu −30.8 (4)
C20—C21—C22—C23 −2.5 (8) C12—C7—P1—C13 −24.3 (4)
C21—C22—C23—C24 1.0 (8) C8—C7—P1—C13 159.3 (3)
C22—C23—C24—C19 1.7 (7) C12—C7—P1—C1 −133.2 (3)
C20—C19—C24—C23 −2.9 (6) C8—C7—P1—C1 50.5 (3)
P2—C19—C24—C23 178.0 (3) C12—C7—P1—Cu 104.9 (3)
C30—C25—C26—C27 0.9 (7) C8—C7—P1—Cu −71.5 (3)
P2—C25—C26—C27 −174.5 (4) C30—C25—P2—C19 165.8 (3)
C25—C26—C27—C28 −1.2 (9) C26—C25—P2—C19 −19.0 (4)
C26—C27—C28—C29 0.7 (10) C30—C25—P2—C31 60.8 (4)
C27—C28—C29—C30 0.2 (9) C26—C25—P2—C31 −124.0 (4)
C26—C25—C30—C29 0.0 (7) C30—C25—P2—Cu −69.3 (4)
P2—C25—C30—C29 175.5 (4) C26—C25—P2—Cu 106.0 (4)
C28—C29—C30—C25 −0.5 (8) C20—C19—P2—C25 117.1 (3)
C36—C31—C32—C33 −1.3 (7) C24—C19—P2—C25 −63.8 (4)
P2—C31—C32—C33 171.9 (4) C20—C19—P2—C31 −135.9 (3)
C31—C32—C33—C34 −0.3 (9) C24—C19—P2—C31 43.2 (4)
C32—C33—C34—C35 1.7 (9) C20—C19—P2—Cu −11.7 (4)
C33—C34—C35—C36 −1.5 (8) C24—C19—P2—Cu 167.4 (3)
C32—C31—C36—C35 1.5 (6) C32—C31—P2—C25 17.6 (4)
P2—C31—C36—C35 −172.1 (3) C36—C31—P2—C25 −169.0 (3)
C34—C35—C36—C31 −0.1 (7) C32—C31—P2—C19 −90.1 (4)
N1—C37—C38—C39 −15.1 (6) C36—C31—P2—C19 83.2 (3)
N1—C37—C38—C43 166.7 (4) C32—C31—P2—Cu 148.8 (4)
C43—C38—C39—C40 −1.6 (6) C36—C31—P2—Cu −37.8 (3)
C37—C38—C39—C40 −179.9 (4) N2—C46—S1—Cu −0.5 (4)
C38—C39—C40—C41 −0.6 (7) S2—C46—S1—Cu 178.3 (2)
C39—C40—C41—N4 −178.1 (4) N2—C46—S2—C47 −176.3 (3)
C39—C40—C41—C42 2.1 (7) S1—C46—S2—C47 4.8 (3)

{Methyl (Z)-2-[4-(dimethylamino)benzylidene]hydrazine-1-carbodithioate-κ2N2,S}bis(triphenylphosphine-κP)copper(I) nitrate carbon tetrachloride monosolvate . Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
N2—H2A···O2i 0.82 1.96 2.754 (5) 163
C2—H2···N1 0.93 2.55 3.391 (5) 151
C36—H36···S1 0.93 2.87 3.758 (5) 160
C37—H37···O2i 0.93 2.66 3.384 (5) 135
C47—H47A···O2 0.96 2.52 3.322 (6) 141

Symmetry code: (i) x−1, y, z.

Funding Statement

VR thanks the Department of Biotechnology (DBT), New Delhi, for the research grant (BT/PR36476/NNT/28/1723/2020) and DST-FIST (SR/FST/CS-1/2021/215), New Delhi.

References

  1. Bianchini, C., Ghilardi, C. A., Meli, A., Midollini, S. & Orlandini, A. (1983). J. Organomet. Chem.255, C27–C30.
  2. Bianchini, C., Ghilardi, C. A., Meli, A., Midollini, S. & Orlandini, A. (2002a). Inorg. Chem.24, 924–931.
  3. Bianchini, C., Ghilardi, C. A., Meli, A., Midollini, S. & Orlandini, A. (2002b). Inorg. Chem.24, 932–939.
  4. Bowmaker, G. A., Boyd, S. E., Hanna, J. V., Hart, R. D., Healy, P. C., Skelton, B. W. & White, A. H. (2002). J. Chem. Soc. Dalton Trans. pp. 2722–2730.
  5. Bruker (2018). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
  6. Egbert, J. D., Cazin, C. S. J. & Nolan, S. P. (2013). Catal. Sci. Technol.3, 912–926.
  7. Eller, P. G. & Kubas, G. J. (2002). J. Am. Chem. Soc.99, 4346–4351.
  8. Hei, X. & Li, J. (2021). Chem. Sci.12, 3805–3817. [DOI] [PMC free article] [PubMed]
  9. Huber, C. P., Post, M. L. & Siiman, O. (1978). Acta Cryst. B34, 2629–2632.
  10. Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst.48, 3–10. [DOI] [PMC free article] [PubMed]
  11. Lobbia, G. G., Pettinari, C., Santini, C., Colapietro, M. & Cecchi, P. (1997). Polyhedron16, 207–215.
  12. Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst.53, 226–235. [DOI] [PMC free article] [PubMed]
  13. Malakar, K., Sohtun, W. P., Srinivasan, V. & Velusamy, M. (2023). Inorg. Chem. Commun.157, 111195.
  14. Marchetti, F., Pettinari, C., Pettinari, R., Cingolani, A., Camalli, M. & Spagna*, R. (2000). Inorg. Chim. Acta299, 65–79.
  15. Messmer, G. G. & Palenik, G. J. (2011). Can. J. Chem.47, 1440–1441.
  16. Mutrofin, S., Chan, E. J., Healy, P. C., Marinelli, A., Ngoune, J., Pettinari, C., Pettinari, R., Somers, N., Skelton, B. W. & White, A. H. (2008). Inorg. Chim. Acta361, 2365–2374.
  17. Papazoglou, I., Cox, P. J., Hatzidimitriou, A. G., Kokotidou, C., Choli-Papadopoulou, T. & Aslanidis, P. (2014). Eur. J. Med. Chem.78, 383–391. [DOI] [PubMed]
  18. Pathaw, L., Maheshwaran, D., Nagendraraj, T., Khamrang, T., Velusamy, M. & Mayilmurugan, R. (2021). Inorg. Chim. Acta514, 119999.
  19. Pettinari, C., Marchetti, F., Polimante, R., Cingolani, A., Portalone, G. & Colapietro, M. (1996). Inorg. Chim. Acta249, 215–229.
  20. Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
  21. Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
  22. Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.
  23. Yang, L., Powell, D. R. & Houser, R. P. (2007). Dalton Trans. pp. 955–964. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989026000228/hb8181sup1.cif

e-82-00168-sup1.cif (3.1MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026000228/hb8181Isup2.hkl

e-82-00168-Isup2.hkl (673.2KB, hkl)

CCDC reference: 2482415

Additional supporting information: crystallographic information; 3D view; checkCIF report


Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography

RESOURCES