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Acta Cryst. (2007). E63, m2412    [ doi:10.1107/S1600536807040925 ]

(Pyrimidine-2-thiolato-[kappa]2N,S)bis(triphenylphosphine-[kappa]P)copper(I)

C.-X. Ruan and W.-J. Shi

Abstract top

The pyrimidine-2-thiolate ligand in the title copper(I) complex, [Cu(C4H3N2S)(C18H15P)2], chelates the metal atom through the exocyclic S atom and one heterocyclic N atom. Two triphenylphosphine ligands complete the approximately tetrahedral coordination geometry about the CuI atom. In the crystal structure, intermolecular C-H...S hydrogen bonds connect the mononuclear complexes into a two-dimensional network.

Comment top

Heterocyclic thiones have attracted much attention as ligands in metal complexes because of their relevance in biological systems (Krebs & Henkel, 1991). Pyrimidine-2-thione and the corresponding thiolate can adopt different coordination modes to yield a variety of coordination complexes (Cookson & Tiekink, 1993; Cotton & Ilsley, 1982; Karagiannidis et al., 1990; Lecomte et al., 1989; Su et al., 1999; Yap & Jensen, 1992; Zhao et al., 2001).

In the earlier study on the complex of copper(I) ion with both phosphine and a heterocyclic mercaptan, Li et al. have found that the heterocyclic thione ligands exist in the thione form in the adduct, the ligands coordinate in a monodentate fashion through the doubly bonded S atom (Li et al., 2004). In this work, the deprotonated ligand coordinates to the copper(I) ion in a chelate manner through an endocyclic N atom and the exocyclic S atom, giving the title complex (Fig. 1). The Cu atom exists in a tetrahedral environment.

A two-dimensional supramolecular network (Fig. 2) is formed by the intermolecular C—H···S hydrogen bonds [H···S 2.73 (3), 2.83 (2) Å; C—H···S 158.6 (1), 149.6 (1) °].

Related literature top

For general background, see: Krebs & Henkel (1991). For details of metal complexes of pyrimidine-2-thiolate, see: Cookson & Tiekink (1993); Cotton & Ilsley (1982); Su et al. (1999); Yap & Jensen (1992); Zhao et al. (2001). For details of the related thiones, see Karagiannidis et al. (1990); Lecomte et al. (1989). For a related structure, see: Li et al. (2004).

Experimental top

Sodium pyrimidine-2-thiolate was prepared through the reaction of pyrimidine-2-thione with sodium metal in dry tetrahydrofuran. To a stirred solution of Cu(NO3)2·3H2O (60.9 mg, 0.25 mmol) in methanol (5 ml) was added a methanol solution (5 ml) of sodium pyrimidine-2-thiolate (34.0 mg, 0.25 mmol) and a precipitate formed immediately. The resulting brown powder was added to a stirred solution of triphenylphosphine (130.2 mg, 0.5 mmol) in acetone (7 ml), forming a clear yellow solution. This was left standing at room temperature. Colorless block-shaped crystals of the title compound were obtained after two months. Yield: 55.6 mg (32%).

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with C—H = 0.93 Å, Uiso = 1.2Ueq(C) for aromatic H-atoms.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level, and H atoms as spheres of arbitrary radius.
[Figure 2] Fig. 2. Packing diagram showing the C—H····S hydrogen bonding interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.
(Pyrimidine-2-thiolato-κ2N,S)bis(triphenylphosphine- κP)copper(I) top
Crystal data top
[Cu(C4H3N2S)(C18H15P)2]Z = 2
Mr = 699.22F000 = 724
Triclinic, P1Dx = 1.313 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 9.3092 (6) ÅCell parameters from 3662 reflections
b = 11.0636 (7) Åθ = 2.2–23.3º
c = 18.8384 (12) ŵ = 0.80 mm−1
α = 93.181 (1)ºT = 295 (2) K
β = 91.912 (2)ºBlock, colourless
γ = 113.810 (2)º0.28 × 0.25 × 0.20 mm
V = 1769.1 (2) Å3
Data collection top
Bruker APEX area-detector
diffractometer		7227 independent reflections
Radiation source: fine-focus sealed tube5598 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.024
T = 295(2) Kθmax = 26.5º
φ and ω scansθmin = 2.0º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.808, Tmax = 0.857k = −13→13
14456 measured reflectionsl = −23→23
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.113  w = 1/[σ2(Fo2) + (0.0585P)2 + 0.2219P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
7227 reflectionsΔρmax = 0.41 e Å−3
415 parametersΔρmin = −0.37 e Å−3
102 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Cu(C4H3N2S)(C18H15P)2]γ = 113.810 (2)º
Mr = 699.22V = 1769.1 (2) Å3
Triclinic, P1Z = 2
a = 9.3092 (6) ÅMo Kα
b = 11.0636 (7) ŵ = 0.80 mm−1
c = 18.8384 (12) ÅT = 295 (2) K
α = 93.181 (1)º0.28 × 0.25 × 0.20 mm
β = 91.912 (2)º
Data collection top
Bruker APEX area-detector
diffractometer		7227 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5598 reflections with I > 2σ(I)
Tmin = 0.808, Tmax = 0.857Rint = 0.024
14456 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044102 restraints
wR(F2) = 0.113H-atom parameters constrained
S = 1.01Δρmax = 0.41 e Å−3
7227 reflectionsΔρmin = −0.37 e Å−3
415 parameters
Special details top

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
xyzUiso*/Ueq
Cu10.69666 (4)0.54945 (3)0.719137 (16)0.04441 (12)
S10.86486 (8)0.44086 (7)0.68664 (4)0.0569 (2)
P10.63061 (8)0.52595 (7)0.83325 (4)0.04319 (17)
P20.73004 (8)0.72462 (6)0.65674 (4)0.04140 (17)
N10.5631 (3)0.3595 (2)0.66490 (11)0.0485 (5)
N20.6660 (4)0.1983 (3)0.63669 (15)0.0736 (8)
C10.6832 (3)0.3203 (3)0.65968 (13)0.0487 (6)
C20.4191 (4)0.2706 (3)0.64506 (17)0.0679 (8)
H20.33480.29510.64770.082*
C30.3917 (5)0.1435 (4)0.6207 (2)0.0885 (12)
H30.29120.08090.60670.106*
C40.5206 (6)0.1146 (4)0.6183 (2)0.0921 (12)
H40.50460.02870.60240.110*
C50.5714 (3)0.3579 (3)0.86245 (14)0.0492 (6)
C60.6564 (4)0.2863 (3)0.84107 (17)0.0695 (9)
H60.74180.32440.81330.083*
C70.6150 (6)0.1576 (4)0.8607 (2)0.0943 (12)
H70.67320.10990.84680.113*
C80.4865 (6)0.1014 (4)0.9011 (2)0.0940 (13)
H80.45690.01490.91360.113*
C90.4043 (5)0.1710 (3)0.92248 (19)0.0798 (10)
H90.31940.13280.95050.096*
C100.4445 (4)0.2988 (3)0.90314 (16)0.0622 (8)
H100.38550.34530.91770.075*
C110.4607 (3)0.5631 (3)0.85071 (14)0.0463 (6)
C120.3271 (3)0.4996 (3)0.80554 (18)0.0672 (8)
H120.32640.43940.76890.081*
C130.1948 (4)0.5252 (4)0.8146 (2)0.0862 (11)
H130.10450.47980.78510.103*
C140.1963 (4)0.6172 (4)0.8668 (2)0.0851 (11)
H140.10830.63620.87190.102*
C150.3260 (4)0.6802 (4)0.9110 (2)0.0783 (10)
H150.32670.74190.94680.094*
C160.4579 (3)0.6535 (3)0.90348 (16)0.0588 (7)
H160.54610.69720.93450.071*
C170.7791 (3)0.6296 (3)0.90186 (14)0.0457 (6)
C180.8176 (3)0.5834 (3)0.96336 (15)0.0600 (7)
H180.76500.49460.97190.072*
C190.9331 (4)0.6677 (4)1.01194 (18)0.0782 (10)
H190.95800.63521.05290.094*
C201.0117 (4)0.7987 (4)1.0007 (2)0.0820 (11)
H201.08990.85521.03360.098*
C210.9738 (4)0.8456 (3)0.9405 (2)0.0796 (10)
H211.02600.93480.93280.095*
C220.8588 (3)0.7619 (3)0.89089 (16)0.0610 (8)
H220.83500.79510.84990.073*
C230.8644 (3)0.8830 (2)0.70027 (14)0.0453 (6)
C241.0025 (3)0.8879 (3)0.73323 (17)0.0609 (8)
H241.02190.81160.73270.073*
C251.1113 (4)1.0045 (4)0.7668 (2)0.0801 (10)
H251.20461.00710.78760.096*
C261.0822 (5)1.1159 (4)0.7695 (2)0.0862 (11)
H261.15421.19370.79350.103*
C270.9471 (5)1.1137 (3)0.7370 (2)0.0795 (10)
H270.92851.19030.73830.095*
C280.8389 (4)0.9980 (3)0.70238 (17)0.0628 (8)
H280.74780.99720.68020.075*
C290.8153 (3)0.7232 (2)0.57102 (14)0.0481 (6)
C300.9305 (4)0.8340 (3)0.54663 (16)0.0670 (7)
H300.96310.91500.57310.080*
C310.9983 (4)0.8262 (3)0.48327 (16)0.0773 (8)
H311.07650.90190.46790.093*
C320.9520 (4)0.7095 (3)0.44330 (17)0.0757 (8)
H320.99560.70510.40000.091*
C330.8406 (5)0.5990 (3)0.46774 (18)0.0904 (10)
H330.80910.51830.44100.108*
C340.7732 (4)0.6044 (3)0.53167 (16)0.0789 (9)
H340.69920.52740.54800.095*
C350.5498 (3)0.7466 (2)0.63579 (14)0.0464 (6)
C360.4941 (4)0.7507 (3)0.56753 (16)0.0604 (7)
H360.55460.75080.52920.072*
C370.3480 (4)0.7547 (3)0.55584 (19)0.0726 (9)
H370.31110.75660.50960.087*
C380.2587 (4)0.7559 (3)0.6109 (2)0.0772 (10)
H380.15990.75640.60260.093*
C390.3152 (4)0.7562 (4)0.6786 (2)0.0886 (11)
H390.25620.76060.71680.106*
C400.4580 (4)0.7501 (4)0.69101 (18)0.0727 (9)
H400.49350.74830.73750.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0511 (2)0.04317 (19)0.0439 (2)0.02402 (15)0.00632 (14)0.00292 (14)
S10.0506 (4)0.0616 (4)0.0663 (5)0.0324 (4)0.0010 (3)−0.0061 (4)
P10.0432 (4)0.0455 (4)0.0410 (4)0.0181 (3)0.0044 (3)0.0025 (3)
P20.0434 (4)0.0419 (4)0.0441 (4)0.0224 (3)0.0061 (3)0.0038 (3)
N10.0483 (13)0.0478 (13)0.0477 (13)0.0185 (11)−0.0026 (10)0.0012 (10)
N20.091 (2)0.0479 (15)0.085 (2)0.0330 (15)0.0004 (16)−0.0061 (14)
C10.0646 (17)0.0501 (16)0.0392 (14)0.0313 (14)0.0034 (12)0.0029 (12)
C20.0587 (19)0.069 (2)0.066 (2)0.0175 (17)−0.0041 (16)−0.0010 (17)
C30.080 (3)0.063 (2)0.090 (3)−0.001 (2)−0.007 (2)−0.008 (2)
C40.112 (3)0.051 (2)0.103 (3)0.025 (2)−0.001 (3)−0.009 (2)
C50.0587 (17)0.0444 (15)0.0402 (14)0.0170 (13)−0.0016 (12)0.0023 (11)
C60.090 (2)0.064 (2)0.064 (2)0.0401 (18)0.0112 (17)0.0156 (16)
C70.142 (4)0.073 (2)0.088 (3)0.063 (3)0.002 (3)0.013 (2)
C80.128 (4)0.054 (2)0.082 (3)0.019 (2)−0.010 (3)0.0170 (19)
C90.083 (2)0.058 (2)0.073 (2)0.0021 (19)−0.0011 (19)0.0115 (18)
C100.0599 (18)0.0561 (18)0.0577 (18)0.0103 (15)0.0012 (15)0.0053 (14)
C110.0391 (14)0.0517 (15)0.0470 (15)0.0164 (12)0.0065 (11)0.0075 (12)
C120.0494 (18)0.075 (2)0.071 (2)0.0196 (16)−0.0019 (15)−0.0011 (17)
C130.0455 (19)0.112 (3)0.093 (3)0.023 (2)−0.0074 (18)0.023 (2)
C140.056 (2)0.109 (3)0.111 (3)0.050 (2)0.023 (2)0.036 (3)
C150.075 (2)0.091 (3)0.088 (3)0.052 (2)0.025 (2)0.009 (2)
C160.0509 (17)0.0708 (19)0.0595 (18)0.0298 (15)0.0061 (14)0.0011 (15)
C170.0368 (13)0.0563 (16)0.0443 (15)0.0190 (12)0.0064 (11)0.0017 (12)
C180.0527 (17)0.0684 (19)0.0546 (18)0.0200 (15)0.0019 (14)0.0086 (15)
C190.068 (2)0.101 (3)0.058 (2)0.028 (2)−0.0135 (17)0.0042 (19)
C200.060 (2)0.090 (3)0.076 (2)0.014 (2)−0.0164 (18)−0.016 (2)
C210.076 (2)0.061 (2)0.084 (3)0.0115 (18)−0.002 (2)−0.0094 (19)
C220.0618 (19)0.0542 (17)0.0578 (18)0.0147 (15)−0.0005 (15)0.0020 (14)
C230.0466 (15)0.0428 (14)0.0474 (15)0.0184 (12)0.0081 (12)0.0050 (11)
C240.0468 (16)0.0636 (19)0.073 (2)0.0239 (15)0.0011 (15)0.0033 (16)
C250.0542 (19)0.084 (3)0.086 (3)0.0127 (18)−0.0102 (17)0.003 (2)
C260.084 (3)0.060 (2)0.083 (3)0.000 (2)−0.002 (2)−0.0084 (19)
C270.103 (3)0.0465 (18)0.086 (3)0.0284 (19)0.002 (2)−0.0038 (17)
C280.072 (2)0.0522 (17)0.068 (2)0.0309 (16)−0.0038 (16)−0.0023 (15)
C290.0581 (14)0.0497 (13)0.0487 (14)0.0332 (11)0.0119 (11)0.0103 (11)
C300.0793 (18)0.0625 (15)0.0639 (16)0.0313 (14)0.0215 (14)0.0124 (13)
C310.090 (2)0.0798 (17)0.0699 (18)0.0386 (16)0.0323 (15)0.0246 (14)
C320.104 (2)0.0863 (18)0.0624 (17)0.0607 (16)0.0352 (15)0.0200 (14)
C330.140 (2)0.0690 (17)0.0681 (18)0.0476 (17)0.0362 (17)0.0004 (15)
C340.118 (2)0.0542 (15)0.0610 (17)0.0294 (15)0.0303 (16)0.0032 (13)
C350.0458 (14)0.0447 (14)0.0530 (15)0.0222 (12)0.0049 (12)0.0072 (12)
C360.0608 (17)0.0711 (19)0.0539 (17)0.0329 (15)−0.0031 (14)−0.0019 (15)
C370.0632 (19)0.084 (2)0.074 (2)0.0354 (18)−0.0173 (17)0.0002 (18)
C380.0539 (18)0.086 (2)0.103 (3)0.0386 (17)0.0008 (18)0.022 (2)
C390.074 (2)0.131 (3)0.095 (2)0.071 (2)0.0334 (19)0.040 (2)
C400.071 (2)0.113 (3)0.0630 (19)0.0626 (19)0.0187 (16)0.0266 (18)
Geometric parameters (Å, °) top
Cu1—N12.139 (2)C17—C181.385 (4)
Cu1—P22.2417 (7)C18—C191.376 (4)
Cu1—P12.2557 (7)C18—H180.9300
Cu1—S12.4023 (7)C19—C201.368 (5)
S1—C11.715 (3)C19—H190.9300
P1—C111.823 (3)C20—C211.365 (5)
P1—C171.826 (3)C20—H200.9300
P1—C51.836 (3)C21—C221.384 (4)
P2—C231.820 (3)C21—H210.9300
P2—C351.824 (3)C22—H220.9300
P2—C291.825 (3)C23—C281.383 (4)
N1—C21.329 (4)C23—C241.389 (4)
N1—C11.357 (3)C24—C251.379 (4)
N2—C41.315 (5)C24—H240.9300
N2—C11.338 (3)C25—C261.364 (5)
C2—C31.373 (5)C25—H250.9300
C2—H20.9300C26—C271.370 (5)
C3—C41.363 (5)C26—H260.9300
C3—H30.9300C27—C281.379 (4)
C4—H40.9300C27—H270.9300
C5—C101.379 (4)C28—H280.9300
C5—C61.380 (4)C29—C341.373 (3)
C6—C71.393 (5)C29—C301.378 (3)
C6—H60.9300C30—C311.383 (3)
C7—C81.382 (6)C30—H300.9300
C7—H70.9300C31—C321.357 (3)
C8—C91.342 (6)C31—H310.9300
C8—H80.9300C32—C331.361 (4)
C9—C101.382 (4)C32—H320.9300
C9—H90.9300C33—C341.386 (3)
C10—H100.9300C33—H330.9300
C11—C161.379 (4)C34—H340.9300
C11—C121.386 (4)C35—C401.377 (4)
C12—C131.384 (5)C35—C361.380 (4)
C12—H120.9300C36—C371.390 (4)
C13—C141.373 (5)C36—H360.9300
C13—H130.9300C37—C381.353 (5)
C14—C151.351 (5)C37—H370.9300
C14—H140.9300C38—C391.362 (5)
C15—C161.384 (4)C38—H380.9300
C15—H150.9300C39—C401.372 (4)
C16—H160.9300C39—H390.9300
C17—C221.379 (4)C40—H400.9300
N1—Cu1—P2115.81 (6)C22—C17—P1117.5 (2)
N1—Cu1—P1104.82 (6)C18—C17—P1124.2 (2)
P2—Cu1—P1126.43 (3)C19—C18—C17120.6 (3)
N1—Cu1—S169.28 (6)C19—C18—H18119.7
P2—Cu1—S1113.43 (3)C17—C18—H18119.7
P1—Cu1—S1112.70 (3)C20—C19—C18120.8 (3)
C1—S1—Cu178.83 (9)C20—C19—H19119.6
C11—P1—C17103.64 (12)C18—C19—H19119.6
C11—P1—C5102.95 (13)C21—C20—C19119.2 (3)
C17—P1—C5103.71 (12)C21—C20—H20120.4
C11—P1—Cu1112.67 (9)C19—C20—H20120.4
C17—P1—Cu1116.99 (8)C20—C21—C22120.8 (3)
C5—P1—Cu1115.25 (9)C20—C21—H21119.6
C23—P2—C35104.69 (12)C22—C21—H21119.6
C23—P2—C29102.33 (12)C17—C22—C21120.4 (3)
C35—P2—C29104.72 (12)C17—C22—H22119.8
C23—P2—Cu1114.48 (9)C21—C22—H22119.8
C35—P2—Cu1114.47 (9)C28—C23—C24118.2 (3)
C29—P2—Cu1114.79 (8)C28—C23—P2124.7 (2)
C2—N1—C1117.5 (3)C24—C23—P2117.1 (2)
C2—N1—Cu1144.9 (2)C25—C24—C23120.7 (3)
C1—N1—Cu196.93 (16)C25—C24—H24119.7
C4—N2—C1115.3 (3)C23—C24—H24119.7
N2—C1—N1124.4 (3)C26—C25—C24120.1 (3)
N2—C1—S1121.1 (2)C26—C25—H25119.9
N1—C1—S1114.42 (19)C24—C25—H25120.0
N1—C2—C3121.6 (3)C25—C26—C27120.2 (3)
N1—C2—H2119.2C25—C26—H26119.9
C3—C2—H2119.2C27—C26—H26119.9
C4—C3—C2116.0 (3)C26—C27—C28120.0 (3)
C4—C3—H3122.0C26—C27—H27120.0
C2—C3—H3122.0C28—C27—H27120.0
N2—C4—C3125.2 (3)C27—C28—C23120.8 (3)
N2—C4—H4117.4C27—C28—H28119.6
C3—C4—H4117.4C23—C28—H28119.6
C10—C5—C6118.6 (3)C34—C29—C30118.1 (3)
C10—C5—P1123.3 (2)C34—C29—P2118.7 (2)
C6—C5—P1118.1 (2)C30—C29—P2122.9 (2)
C5—C6—C7120.5 (3)C29—C30—C31120.8 (3)
C5—C6—H6119.8C29—C30—H30119.6
C7—C6—H6119.8C31—C30—H30119.6
C8—C7—C6119.2 (4)C32—C31—C30120.8 (3)
C8—C7—H7120.4C32—C31—H31119.6
C6—C7—H7120.4C30—C31—H31119.6
C9—C8—C7120.5 (4)C31—C32—C33118.7 (3)
C9—C8—H8119.8C31—C32—H32120.6
C7—C8—H8119.8C33—C32—H32120.6
C8—C9—C10120.6 (4)C32—C33—C34121.3 (3)
C8—C9—H9119.7C32—C33—H33119.4
C10—C9—H9119.7C34—C33—H33119.4
C5—C10—C9120.6 (3)C29—C34—C33120.2 (3)
C5—C10—H10119.7C29—C34—H34119.9
C9—C10—H10119.7C33—C34—H34119.9
C16—C11—C12117.9 (3)C40—C35—C36117.9 (3)
C16—C11—P1124.8 (2)C40—C35—P2117.9 (2)
C12—C11—P1117.3 (2)C36—C35—P2124.0 (2)
C13—C12—C11120.5 (3)C35—C36—C37120.2 (3)
C13—C12—H12119.7C35—C36—H36119.9
C11—C12—H12119.7C37—C36—H36119.9
C14—C13—C12120.3 (3)C38—C37—C36120.8 (3)
C14—C13—H13119.9C38—C37—H37119.6
C12—C13—H13119.9C36—C37—H37119.6
C15—C14—C13119.8 (3)C37—C38—C39119.2 (3)
C15—C14—H14120.1C37—C38—H38120.4
C13—C14—H14120.1C39—C38—H38120.4
C14—C15—C16120.5 (3)C38—C39—C40120.7 (3)
C14—C15—H15119.8C38—C39—H39119.7
C16—C15—H15119.8C40—C39—H39119.7
C11—C16—C15121.0 (3)C39—C40—C35121.1 (3)
C11—C16—H16119.5C39—C40—H40119.4
C15—C16—H16119.5C35—C40—H40119.4
C22—C17—C18118.3 (3)
N1—Cu1—S1—C1−4.01 (11)C11—C12—C13—C142.3 (5)
P2—Cu1—S1—C1−114.09 (9)C12—C13—C14—C15−2.0 (6)
P1—Cu1—S1—C193.93 (9)C13—C14—C15—C160.6 (6)
N1—Cu1—P1—C11−89.40 (11)C12—C11—C16—C15−0.1 (4)
P2—Cu1—P1—C1149.62 (10)P1—C11—C16—C15177.0 (2)
S1—Cu1—P1—C11−162.77 (10)C14—C15—C16—C110.4 (5)
N1—Cu1—P1—C17150.64 (12)C11—P1—C17—C22−79.2 (2)
P2—Cu1—P1—C17−70.34 (10)C5—P1—C17—C22173.5 (2)
S1—Cu1—P1—C1777.26 (10)Cu1—P1—C17—C2245.4 (2)
N1—Cu1—P1—C528.35 (12)C11—P1—C17—C18101.6 (2)
P2—Cu1—P1—C5167.37 (10)C5—P1—C17—C18−5.7 (3)
S1—Cu1—P1—C5−45.03 (11)Cu1—P1—C17—C18−133.8 (2)
N1—Cu1—P2—C23−172.61 (11)C22—C17—C18—C19−0.3 (4)
P1—Cu1—P2—C2352.16 (10)P1—C17—C18—C19178.9 (2)
S1—Cu1—P2—C23−95.24 (9)C17—C18—C19—C200.3 (5)
N1—Cu1—P2—C3566.51 (12)C18—C19—C20—C210.2 (6)
P1—Cu1—P2—C35−68.72 (10)C19—C20—C21—C22−0.7 (6)
S1—Cu1—P2—C35143.87 (10)C18—C17—C22—C21−0.1 (4)
N1—Cu1—P2—C29−54.66 (12)P1—C17—C22—C21−179.4 (2)
P1—Cu1—P2—C29170.11 (10)C20—C21—C22—C170.6 (5)
S1—Cu1—P2—C2922.70 (10)C35—P2—C23—C28−11.3 (3)
P2—Cu1—N1—C2−79.7 (4)C29—P2—C23—C2897.8 (3)
P1—Cu1—N1—C264.5 (4)Cu1—P2—C23—C28−137.4 (2)
S1—Cu1—N1—C2173.5 (4)C35—P2—C23—C24169.1 (2)
P2—Cu1—N1—C1111.82 (14)C29—P2—C23—C24−81.8 (2)
P1—Cu1—N1—C1−104.06 (15)Cu1—P2—C23—C2443.0 (2)
S1—Cu1—N1—C15.01 (14)C28—C23—C24—C25−0.3 (4)
C4—N2—C1—N10.2 (5)P2—C23—C24—C25179.4 (2)
C4—N2—C1—S1179.3 (3)C23—C24—C25—C261.7 (5)
C2—N1—C1—N2−0.7 (4)C24—C25—C26—C27−2.1 (6)
Cu1—N1—C1—N2171.9 (2)C25—C26—C27—C281.1 (6)
C2—N1—C1—S1−179.8 (2)C26—C27—C28—C230.3 (5)
Cu1—N1—C1—S1−7.21 (19)C24—C23—C28—C27−0.7 (4)
Cu1—S1—C1—N2−172.6 (2)P2—C23—C28—C27179.7 (2)
Cu1—S1—C1—N16.50 (17)C23—P2—C29—C34161.5 (3)
C1—N1—C2—C30.5 (5)C35—P2—C29—C34−89.5 (3)
Cu1—N1—C2—C3−166.6 (3)Cu1—P2—C29—C3436.9 (3)
N1—C2—C3—C40.1 (6)C23—P2—C29—C30−12.7 (3)
C1—N2—C4—C30.5 (6)C35—P2—C29—C3096.4 (3)
C2—C3—C4—N2−0.6 (6)Cu1—P2—C29—C30−137.3 (2)
C11—P1—C5—C10−13.9 (3)C34—C29—C30—C311.8 (5)
C17—P1—C5—C1093.9 (2)P2—C29—C30—C31176.1 (3)
Cu1—P1—C5—C10−136.9 (2)C29—C30—C31—C320.5 (5)
C11—P1—C5—C6164.6 (2)C30—C31—C32—C33−1.9 (6)
C17—P1—C5—C6−87.7 (2)C31—C32—C33—C340.8 (6)
Cu1—P1—C5—C641.5 (3)C30—C29—C34—C33−2.9 (5)
C10—C5—C6—C7−0.4 (5)P2—C29—C34—C33−177.3 (3)
P1—C5—C6—C7−179.0 (3)C32—C33—C34—C291.6 (6)
C5—C6—C7—C80.8 (6)C23—P2—C35—C40−73.4 (3)
C6—C7—C8—C9−1.3 (6)C29—P2—C35—C40179.3 (2)
C7—C8—C9—C101.4 (6)Cu1—P2—C35—C4052.8 (3)
C6—C5—C10—C90.5 (4)C23—P2—C35—C36111.3 (3)
P1—C5—C10—C9178.9 (2)C29—P2—C35—C364.0 (3)
C8—C9—C10—C5−1.0 (5)Cu1—P2—C35—C36−122.5 (2)
C17—P1—C11—C161.8 (3)C40—C35—C36—C37−1.6 (5)
C5—P1—C11—C16109.6 (3)P2—C35—C36—C37173.7 (2)
Cu1—P1—C11—C16−125.6 (2)C35—C36—C37—C380.6 (5)
C17—P1—C11—C12178.9 (2)C36—C37—C38—C391.5 (6)
C5—P1—C11—C12−73.2 (2)C37—C38—C39—C40−2.6 (6)
Cu1—P1—C11—C1251.5 (2)C38—C39—C40—C351.5 (6)
C16—C11—C12—C13−1.2 (5)C36—C35—C40—C390.6 (5)
P1—C11—C12—C13−178.6 (3)P2—C35—C40—C39−175.0 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C6—H6···S10.932.833.661 (3)150
C13—H13···S1i0.932.733.613 (4)159
Symmetry codes: (i) x−1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C6—H6···S10.932.833.661 (3)150
C13—H13···S1i0.932.733.613 (4)159
Symmetry codes: (i) x−1, y, z.
Acknowledgements top

The authors thank Jiangxi Science and Technology Normal University for supporting this study.

references
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