metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 71| Part 3| March 2015| Pages m61-m62

Crystal structure of [1,3-bis­­(di­phenyl­phosphan­yl)propane-κ2P,P′](N,N′-di­methyl­thio­urea-κS)(thio­cyanato-κN)copper(I)

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aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand, and bDepartment of Chemistry, Youngstown State University, 1 University Plaza, 44555 Youngstown, OH, USA
*Correspondence e-mail: yupa.t@psu.ac.th

Edited by A. J. Lough, University of Toronto, Canada (Received 31 January 2015; accepted 5 February 2015; online 11 February 2015)

The asymmetric unit of the title compound, [Cu(NCS)(C3H8N2S)(C27H26P2)], contains two independent mononuclear complex mol­ecules. In each, the CuI ion exhibits a distorted tetra­hedral geometry by coordination with two P atoms from one 1,3-bis(diphenylphosphino)propane (dppm) ligand, one terminal S atom of one N,N′-di­methyl­thio­urea (dmtu) ligand and one terminal N atom of the thio­cyanato ligand. The dppp ligand is involved in a bidentate coordination mode with the CuI ion, forming a six-membered CuP2C3 ring. In both mol­ecules, the coordination of the dmtu ligand is further stabilized by an intra­molecular N—H⋯N hydrogen bond with an S(6) graph-set motif. In the crystal, mol­ecules are linked by N—H⋯S hydrogen bonds forming a zigzag chain along the a-axis direction. In one independent mol­ecule, one of the phenyl rings of the dppp ligand is disordered over two sites with refined occupancies 0.639 (11):0.361 (11) and this corresponds with a mutual disorder of the dmtu ligand in the other independent mol­ecule giving the same ratio of refined occupancies. The structure was refined as a two-component inversion twin.

1. Related literature

For applications of thio­urea, thio­urea derivatives and their complexes, see: Chen et al. (2009[Chen, M. H., Chen, Z., Song, B. A., Bhadury, P. S., Yang, S., Cai, X. J., Hu, D. Y., Xue, W. & Zeng, S. (2009). J. Agric. Food Chem. 57, 1383-1388.]); Isab et al. (2010[Isab, A. A., Nawaz, S., Saleem, M., Altaf, M., Monim-ul-Mehboob, M., Ahmad, S. & Evans, H. S. (2010). Polyhedron, 29, 1251-1256.]); Saeed et al. (2010[Saeed, S., Rashid, N., Jones, P. G., Hussain, R. & Bhatti, M. H. (2010). Cent. Eur. J. Chem. 8, 550-558.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • [Cu(NCS)(C3H8N2S)(C27H26P2)]

  • Mr = 638.21

  • Monoclinic, P 21

  • a = 9.9727 (15) Å

  • b = 31.971 (5) Å

  • c = 10.2162 (15) Å

  • β = 110.022 (2)°

  • V = 3060.4 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.98 mm−1

  • T = 100 K

  • 0.44 × 0.42 × 0.26 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan SADABS (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.566, Tmax = 0.746

  • 24402 measured reflections

  • 13908 independent reflections

  • 12457 reflections with I > 2σ(I)

  • Rint = 0.027

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.111

  • S = 1.06

  • 13908 reflections

  • 744 parameters

  • 140 restraints

  • H-atom parameters constrained

  • Δρmax = 1.32 e Å−3

  • Δρmin = −0.69 e Å−3

  • Absolute structure: refined as an inversion twin

  • Absolute structure parameter: 0.158 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯S2Bi 0.88 2.64 3.466 (5) 158
N2—H2⋯N3 0.88 2.32 3.174 (7) 165
N2B—H2L⋯N3B 0.88 2.43 3.286 (13) 164
N1B—H1B⋯S1 0.88 2.55 3.350 (13) 151
N2C—H2M⋯N3B 0.88 2.50 3.24 (2) 142
N1C—H1C⋯S1 0.88 2.58 3.34 (2) 146
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and SHELXLE (Hübschle et al., 2011[Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284.]); molecular graphics: Mercury (Macrae, 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Thio­urea and thio­urea derivatives as well as their complexes have been widely studied because of their relevance in biological systems such as anti­microbial, anti­viral and anti fungal (Chen et al., 2009; Isab et al., 2010; Saeed et al., 2010). The use of diphosphine lead to the mononuclear complex we have prepared in this study. The asymmetric unit of the title compound, [Cu(NCS)(C3H8N2S)(C27H26P2)], contains two independent mononuclear complex molecules (Fig. 1). In each, the CuI ion exhibits a distorted tetra­hedral geometry by coordination with two P atoms from one propane-1,3-bis­(di­phenyl­phosphino) (dppm) ligand, one terminal S atom of one N,N'-di­methyl­thio­urea (dmtu) ligand and one terminal N atom of thio­cyanate ligand. The dppp ligand is involved in a bidentate coordination mode with the CuI ion, forming a six-membered CuP2C3 ring. In both molecules, the coordination of the dmtu ligand is further stabilized by an intra­molecular N—H···N hydrogen bond (Table 1) with S(6) graph-set motif. In the crystal, molecules are linked by N—H···S hydrogen bonds forming a one-dimensional zigzag chain along the a-axis direction (see Table 1 and Fig. 2). In molecule A, one of the phenyl rings of the dppp ligand is disordered over two sites with refined occupancies 0.639 (11):0.361 (11) and this corresponds with a mutual disorder of the dmtu ligand in molecule B giving the same ratio of refined occupancies.

Experimental top

Propane-1,3-bis­(di­phenyl­phosphino), dppp, (0.34 g, 0.8 mmol) was dissolved in 30 ml of aceto­nitrile at 338 K and then copperthio­cynate, CuSCN, (0.10 g, 0.8 mmol) was added. The mixture was stirred for 3 hr and then N,N′-di­methyl­thio­urea, dmtu, (0.09 g, 0.8 mmol) was added and the new reaction mixture was heated under reflux for 4 hr during which the precipitate gradually disappeared. The resulting clear solution was filtered and left to evaporate at room temperature. The crystalline complex, which deposited upon standing for several days, was filtered off and dried in vacuo.

Refinement top

Reflections 020, 0-20, -505, -605 and 006 were affected by the beam stop and were omitted from the refinement. H atoms bonded to C and N atoms were included in calculated positions and were refined with a riding model using distances of 0.95 Å (aryl H), and Uiso(H) = 1.2Ueq(C); 0.98 Å (CH3) and Uiso(H) = 1.5Ueq(C); 0.88 Å (NH), and Uiso(H) = 1.2Ueq(N). One of phenyl rings of the dppp ligand in molecule A is mutually disordered with the dmtu of molecule B. The ADPs of the carbon and nitro­gen atoms were constrained to be identical. An enhanced rigid bond restraint was applied to all disordered atoms [RIGU in SHELXL (Sheldrick, 2008)]. To ensure satisfactory refinement the atoms of each disorder component of the phenyl ring and the directly attached carbon atoms were each restrained to lie within a common plane. The overall ratio of the two components of disorder refined to 0.639 (11) and 0.361 (11).

Related literature top

For applications of thiourea, thiourea derivatives and their complexes, see: Chen et al. (2009); Isab et al. (2010); Saeed et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) and SHELXLE (Hübschle et al., 2011); molecular graphics: Mercury (Macrae, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure with displacement ellipsoids drawn at the 50% probability level. The minor component of disorder is omitted for clarity.
[Figure 2] Fig. 2. Part of the crystal structure showing intermolecular N—H···S hydrogen bonds as dashed lines, forming a zigzag chain along the a-axis.
[1,3-Bis(diphenylphosphanyl)propane-κ2P,P'](N,N'-dimethylthiourea-κS)(thiocyanato-κN)copper(I) top
Crystal data top
[Cu(NCS)(C3H8N2S)(C27H26P2)]F(000) = 1328
Mr = 638.21Dx = 1.385 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.9727 (15) ÅCell parameters from 986 reflections
b = 31.971 (5) Åθ = 2.9–29.6°
c = 10.2162 (15) ŵ = 0.98 mm1
β = 110.022 (2)°T = 100 K
V = 3060.4 (8) Å3Prism, colourless
Z = 40.44 × 0.42 × 0.26 mm
Data collection top
Bruker APEXII CCD
diffractometer
13908 independent reflections
Radiation source: fine focus sealed tube12457 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω and ϕ scansθmax = 31.6°, θmin = 2.1°
Absorption correction: multi-scan
SADABS (Bruker, 2013)
h = 1413
Tmin = 0.566, Tmax = 0.746k = 4544
24402 measured reflectionsl = 1312
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)] = 0.045H-atom parameters constrained
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0442P)2 + 4.2761P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
13908 reflectionsΔρmax = 1.32 e Å3
744 parametersΔρmin = 0.69 e Å3
140 restraintsAbsolute structure: Refined as an inversion twin.
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.158 (14)
Crystal data top
[Cu(NCS)(C3H8N2S)(C27H26P2)]V = 3060.4 (8) Å3
Mr = 638.21Z = 4
Monoclinic, P21Mo Kα radiation
a = 9.9727 (15) ŵ = 0.98 mm1
b = 31.971 (5) ÅT = 100 K
c = 10.2162 (15) Å0.44 × 0.42 × 0.26 mm
β = 110.022 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
13908 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 2013)
12457 reflections with I > 2σ(I)
Tmin = 0.566, Tmax = 0.746Rint = 0.027
24402 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.111Δρmax = 1.32 e Å3
S = 1.06Δρmin = 0.69 e Å3
13908 reflectionsAbsolute structure: Refined as an inversion twin.
744 parametersAbsolute structure parameter: 0.158 (14)
140 restraints
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. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.23083 (6)0.48822 (2)0.95389 (7)0.01440 (14)
S10.29244 (14)0.55158 (4)0.85602 (16)0.0173 (3)
S20.24387 (16)0.52907 (5)1.40265 (17)0.0247 (3)
P10.05689 (13)0.46187 (4)0.77085 (16)0.0139 (3)
P20.41776 (13)0.45185 (4)0.93301 (15)0.0128 (3)
N10.5053 (5)0.60594 (15)0.9529 (6)0.0244 (11)
H10.56690.62011.02100.029*
N20.4300 (5)0.57410 (15)1.1162 (6)0.0244 (12)
H20.36900.55721.13420.029*
N30.2224 (5)0.50129 (15)1.1380 (6)0.0201 (11)
C10.4191 (5)0.57906 (15)0.9854 (6)0.0167 (12)
C20.5035 (9)0.6131 (2)0.8124 (9)0.0425 (19)
H2C0.51200.58630.76930.064*
H2D0.58360.63130.81510.064*
H2E0.41350.62670.75780.064*
S2B0.24826 (15)0.67958 (5)1.13983 (16)0.0219 (3)
C1B0.0620 (17)0.6408 (6)0.7188 (12)0.0139 (19)0.639 (11)
N2B0.0397 (12)0.6469 (4)0.8525 (12)0.019 (2)0.639 (11)
H2L0.10340.66190.87370.022*0.639 (11)
C3B0.0815 (14)0.6310 (4)0.9691 (15)0.032 (3)0.639 (11)
H3BA0.08880.60060.95980.048*0.639 (11)
H3BB0.06700.63731.05710.048*0.639 (11)
H3BC0.16960.64430.96820.048*0.639 (11)
N1B0.0284 (14)0.6167 (4)0.6824 (12)0.023 (2)0.639 (11)
H1B0.10640.60800.74800.027*0.639 (11)
C2B0.0045 (15)0.6042 (5)0.5409 (13)0.042 (3)0.639 (11)
H2F0.08540.58870.50500.063*0.639 (11)
H2G0.08330.58630.53810.063*0.639 (11)
H2H0.00070.62910.48340.063*0.639 (11)
C1C0.060 (3)0.6427 (12)0.751 (3)0.0139 (19)0.361 (11)
N2C0.061 (2)0.6389 (7)0.881 (2)0.019 (2)0.361 (11)
H2M0.13320.64950.90120.022*0.361 (11)
C3C0.053 (3)0.6174 (7)0.990 (3)0.032 (3)0.361 (11)
H3BD0.04380.58710.97440.048*0.361 (11)
H3BE0.04730.62411.08110.048*0.361 (11)
H3BF0.14590.62660.98640.048*0.361 (11)
N1C0.045 (3)0.6249 (8)0.720 (2)0.023 (2)0.361 (11)
H1C0.11300.61260.78760.027*0.361 (11)
C2C0.056 (3)0.6241 (8)0.584 (2)0.042 (3)0.361 (11)
H2I0.02640.60930.51930.063*0.361 (11)
H2J0.14390.60960.58760.063*0.361 (11)
H2K0.05800.65280.55060.063*0.361 (11)
P2B0.08332 (14)0.76514 (4)0.67173 (16)0.0140 (3)
C30.5364 (7)0.5947 (2)1.2340 (8)0.0344 (16)
H3A0.63230.58781.23430.052*
H3B0.52600.58511.32110.052*
H3C0.52240.62511.22560.052*
N3B0.2716 (5)0.71589 (15)0.8829 (6)0.0246 (12)
C40.2307 (5)0.51225 (16)1.2477 (6)0.0158 (12)
C110.1138 (19)0.4900 (4)0.698 (3)0.0175 (17)0.639 (11)
C120.2334 (19)0.4711 (4)0.604 (2)0.016 (3)0.639 (11)
H120.22790.44340.57230.020*0.639 (11)
C130.3634 (19)0.4934 (4)0.555 (2)0.016 (3)0.639 (11)
H130.44690.48000.49490.019*0.639 (11)
C140.3700 (15)0.5338 (5)0.594 (2)0.025 (3)0.639 (11)
H140.45540.54940.55380.030*0.639 (11)
C150.2522 (10)0.5522 (3)0.6918 (13)0.023 (3)0.639 (11)
H150.25910.57980.72330.028*0.639 (11)
C160.1228 (11)0.5302 (3)0.7446 (13)0.022 (3)0.639 (11)
H160.04220.54280.81190.027*0.639 (11)
C11C0.113 (3)0.4881 (7)0.688 (5)0.0175 (17)0.361 (11)
C12C0.237 (3)0.4653 (8)0.625 (5)0.016 (3)0.361 (11)
H12C0.23420.43560.62400.020*0.361 (11)
C13C0.367 (3)0.4861 (8)0.564 (5)0.016 (3)0.361 (11)
H13C0.45130.47040.52040.020*0.361 (11)
C14C0.373 (3)0.5281 (9)0.567 (5)0.025 (3)0.361 (11)
H14C0.46280.54160.52950.030*0.361 (11)
C15C0.2497 (18)0.5521 (5)0.623 (2)0.023 (3)0.361 (11)
H15C0.25310.58180.61610.028*0.361 (11)
C16C0.120 (2)0.5312 (7)0.691 (3)0.022 (3)0.361 (11)
H16C0.03630.54680.73830.027*0.361 (11)
C210.0031 (5)0.40938 (15)0.7913 (6)0.0136 (11)
S1B0.20509 (16)0.66393 (4)0.60428 (19)0.0275 (4)
Cu1B0.26535 (6)0.72732 (2)0.69714 (7)0.01687 (16)
P1B0.44267 (14)0.74965 (4)0.50908 (15)0.0135 (3)
C220.0370 (5)0.40178 (16)0.9099 (6)0.0145 (11)
H220.02940.42380.97460.017*
C230.0817 (6)0.36252 (17)0.9355 (6)0.0175 (12)
H230.10530.35781.01680.021*
C240.0921 (6)0.33034 (17)0.8432 (7)0.0207 (13)
H240.12080.30330.86150.025*
C250.0601 (6)0.33770 (17)0.7224 (7)0.0211 (13)
H250.06860.31560.65780.025*
C260.0162 (6)0.37685 (17)0.6963 (7)0.0198 (12)
H260.00500.38170.61370.024*
C270.1234 (5)0.45820 (17)0.6242 (6)0.0169 (11)
H27A0.04840.44490.54510.020*
H27B0.13720.48700.59520.020*
C27B0.3761 (5)0.75374 (17)0.3619 (6)0.0164 (11)
H27C0.35800.72510.33510.020*
H27D0.45290.76590.28170.020*
C26B0.5248 (6)0.83380 (17)0.4309 (6)0.0167 (11)
H26B0.50860.82870.34600.020*
C25B0.5646 (6)0.87332 (18)0.4609 (8)0.0246 (14)
H25B0.57330.89540.39630.029*
C24B0.5916 (6)0.88113 (17)0.5808 (6)0.0171 (12)
H24B0.62010.90830.59840.021*
C23B0.5771 (5)0.84925 (17)0.6773 (6)0.0175 (12)
H23B0.59510.85450.76130.021*
C22B0.5362 (5)0.80970 (16)0.6496 (6)0.0167 (12)
H22B0.52680.78780.71510.020*
C21B0.5089 (5)0.80166 (16)0.5285 (6)0.0127 (11)
C16B0.5997 (6)0.67626 (18)0.4434 (7)0.0255 (13)
H16B0.51070.66300.48920.031*
C15B0.7222 (6)0.65191 (19)0.3874 (7)0.0319 (16)
H15B0.71690.62230.39590.038*
C14B0.8517 (6)0.67135 (19)0.3194 (7)0.0241 (13)
H14B0.93550.65500.28040.029*
C13B0.8595 (6)0.7137 (2)0.3081 (7)0.0240 (13)
H13B0.94870.72680.26120.029*
C12B0.7379 (6)0.73816 (17)0.3646 (6)0.0190 (12)
H12B0.74450.76780.35660.023*
C11B0.6055 (5)0.71926 (17)0.4332 (6)0.0152 (11)
C280.2630 (6)0.43390 (17)0.6502 (6)0.0166 (11)
H28A0.27440.42880.55900.020*
H28B0.25320.40630.68990.020*
C28B0.2398 (6)0.77977 (17)0.3860 (6)0.0197 (12)
H28C0.25400.80760.42130.024*
H28D0.22690.78400.29500.024*
C290.4005 (5)0.45453 (16)0.7469 (6)0.0167 (11)
H29A0.40180.48420.71980.020*
H29B0.48380.44050.73420.020*
C29B0.1007 (5)0.76057 (17)0.4887 (6)0.0169 (11)
H29C0.01800.77450.47470.020*
H29D0.09700.73060.46590.020*
C310.4403 (5)0.39548 (16)0.9623 (6)0.0126 (10)
C320.3305 (6)0.37296 (17)0.9855 (6)0.0194 (12)
H320.25110.38740.99510.023*
C330.3366 (6)0.32970 (17)0.9945 (6)0.0202 (12)
H330.26090.31471.00960.024*
C340.4504 (6)0.30837 (17)0.9820 (6)0.0181 (12)
H340.45350.27870.98750.022*
C350.5616 (6)0.33050 (18)0.9610 (7)0.0209 (12)
H350.64160.31580.95400.025*
C360.5571 (6)0.37386 (17)0.9502 (6)0.0163 (12)
H360.63290.38870.93460.020*
C410.5921 (5)0.47370 (16)1.0282 (6)0.0176 (12)
C420.6914 (6)0.4860 (2)0.9675 (7)0.0271 (14)
H420.67170.48190.87060.032*
C430.8217 (7)0.5045 (2)1.0501 (8)0.0342 (16)
H430.88990.51281.00910.041*
C440.8492 (6)0.5106 (2)1.1905 (8)0.0331 (17)
H440.93640.52321.24620.040*
C450.7526 (6)0.4987 (2)1.2494 (7)0.0292 (15)
H450.77220.50301.34620.035*
C460.6250 (6)0.48018 (18)1.1690 (7)0.0248 (13)
H460.55880.47181.21220.030*
C4B0.2630 (5)0.70142 (16)0.9887 (6)0.0148 (11)
C31B0.0601 (5)0.82157 (16)0.6981 (6)0.0152 (11)
C32B0.1698 (5)0.84492 (17)0.7197 (6)0.0147 (11)
H32B0.25030.83100.72870.018*
C33B0.1614 (6)0.88834 (18)0.7280 (6)0.0200 (12)
H33B0.23780.90410.73850.024*
C34B0.0405 (6)0.90849 (18)0.7207 (7)0.0211 (13)
H34B0.03380.93810.72830.025*
C35B0.0707 (6)0.88569 (17)0.7025 (7)0.0217 (12)
H35B0.15320.89960.69800.026*
C36B0.0600 (6)0.84242 (18)0.6910 (7)0.0189 (13)
H36B0.13570.82680.67820.023*
C41B0.0947 (5)0.74421 (15)0.7681 (6)0.0160 (11)
C42B0.1932 (6)0.73248 (18)0.7065 (7)0.0242 (13)
H42B0.17160.73580.60900.029*
C43B0.3243 (6)0.71581 (18)0.7887 (7)0.0240 (13)
H43B0.39190.70790.74650.029*
C44B0.3570 (6)0.71065 (18)0.9294 (7)0.0224 (13)
H44B0.44600.69890.98430.027*
C45B0.2588 (6)0.7227 (2)0.9907 (7)0.0303 (15)
H45B0.28200.72001.08860.036*
C46B0.1269 (6)0.73879 (18)0.9107 (7)0.0232 (13)
H46B0.05890.74600.95310.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0086 (3)0.0155 (3)0.0172 (4)0.0008 (2)0.0019 (2)0.0046 (3)
S10.0134 (6)0.0137 (6)0.0220 (8)0.0002 (4)0.0025 (5)0.0010 (5)
S20.0205 (7)0.0356 (8)0.0173 (8)0.0069 (6)0.0055 (6)0.0054 (6)
P10.0081 (6)0.0125 (6)0.0176 (8)0.0012 (4)0.0001 (5)0.0005 (5)
P20.0087 (6)0.0133 (6)0.0149 (7)0.0016 (4)0.0022 (5)0.0005 (5)
N10.020 (2)0.022 (2)0.030 (3)0.0079 (18)0.008 (2)0.003 (2)
N20.021 (2)0.021 (2)0.029 (3)0.0091 (18)0.006 (2)0.002 (2)
N30.012 (2)0.023 (2)0.025 (3)0.0028 (16)0.007 (2)0.005 (2)
C10.011 (2)0.012 (2)0.027 (4)0.0018 (17)0.005 (2)0.000 (2)
C20.051 (5)0.037 (4)0.046 (5)0.022 (3)0.025 (4)0.008 (3)
S2B0.0154 (6)0.0307 (7)0.0172 (8)0.0035 (5)0.0024 (5)0.0025 (6)
C1B0.017 (3)0.008 (3)0.015 (5)0.0004 (19)0.004 (4)0.002 (4)
N2B0.018 (4)0.022 (5)0.015 (5)0.007 (3)0.004 (3)0.000 (3)
C3B0.040 (6)0.018 (7)0.022 (5)0.010 (5)0.010 (4)0.004 (4)
N1B0.021 (4)0.025 (6)0.022 (6)0.011 (4)0.007 (4)0.002 (4)
C2B0.047 (7)0.055 (8)0.026 (6)0.025 (5)0.015 (5)0.003 (4)
C1C0.017 (3)0.008 (3)0.015 (5)0.0004 (19)0.004 (4)0.002 (4)
N2C0.018 (4)0.022 (5)0.015 (5)0.007 (3)0.004 (3)0.000 (3)
C3C0.040 (6)0.018 (7)0.022 (5)0.010 (5)0.010 (4)0.004 (4)
N1C0.021 (4)0.025 (6)0.022 (6)0.011 (4)0.007 (4)0.002 (4)
C2C0.047 (7)0.055 (8)0.026 (6)0.025 (5)0.015 (5)0.003 (4)
P2B0.0086 (6)0.0156 (6)0.0172 (8)0.0001 (4)0.0035 (5)0.0021 (5)
C30.034 (4)0.030 (3)0.030 (4)0.014 (3)0.001 (3)0.001 (3)
N3B0.014 (2)0.024 (2)0.034 (3)0.0022 (17)0.005 (2)0.005 (2)
C40.008 (2)0.018 (2)0.020 (3)0.0029 (17)0.003 (2)0.001 (2)
C110.011 (2)0.014 (2)0.022 (4)0.0019 (19)0.001 (2)0.001 (2)
C120.014 (2)0.014 (4)0.017 (7)0.001 (3)0.000 (3)0.003 (4)
C130.017 (4)0.020 (6)0.008 (5)0.000 (4)0.000 (3)0.007 (5)
C140.013 (2)0.019 (4)0.042 (9)0.002 (2)0.006 (3)0.004 (4)
C150.015 (3)0.014 (3)0.040 (7)0.000 (2)0.009 (4)0.001 (4)
C160.012 (3)0.018 (3)0.037 (8)0.0030 (19)0.010 (4)0.001 (4)
C11C0.011 (2)0.014 (2)0.022 (4)0.0019 (19)0.001 (2)0.001 (2)
C12C0.014 (2)0.014 (4)0.017 (7)0.001 (3)0.000 (3)0.003 (4)
C13C0.014 (2)0.014 (4)0.017 (7)0.001 (3)0.000 (3)0.003 (4)
C14C0.013 (2)0.019 (4)0.042 (9)0.002 (2)0.006 (3)0.004 (4)
C15C0.015 (3)0.014 (3)0.040 (7)0.000 (2)0.009 (4)0.001 (4)
C16C0.012 (3)0.018 (3)0.037 (8)0.0030 (19)0.010 (4)0.001 (4)
C210.010 (2)0.013 (2)0.016 (3)0.0005 (17)0.002 (2)0.002 (2)
S1B0.0211 (7)0.0174 (7)0.0390 (10)0.0079 (5)0.0039 (7)0.0061 (6)
Cu1B0.0091 (3)0.0173 (3)0.0221 (4)0.0009 (2)0.0026 (3)0.0066 (3)
P1B0.0091 (6)0.0126 (6)0.0172 (8)0.0006 (4)0.0024 (5)0.0012 (5)
C220.013 (2)0.014 (2)0.011 (3)0.0011 (17)0.003 (2)0.003 (2)
C230.012 (2)0.023 (3)0.016 (3)0.0002 (18)0.003 (2)0.005 (2)
C240.016 (3)0.014 (2)0.029 (4)0.0015 (19)0.004 (2)0.001 (2)
C250.024 (3)0.015 (3)0.023 (4)0.004 (2)0.007 (3)0.006 (2)
C260.019 (3)0.019 (3)0.019 (3)0.004 (2)0.004 (2)0.003 (2)
C270.015 (2)0.019 (2)0.013 (3)0.0005 (19)0.000 (2)0.003 (2)
C27B0.012 (2)0.023 (3)0.016 (3)0.0004 (18)0.007 (2)0.003 (2)
C26B0.019 (3)0.022 (3)0.010 (3)0.0022 (19)0.006 (2)0.001 (2)
C25B0.019 (3)0.017 (3)0.039 (4)0.005 (2)0.012 (3)0.011 (3)
C24B0.015 (3)0.015 (2)0.018 (3)0.0049 (19)0.002 (2)0.001 (2)
C23B0.011 (2)0.023 (3)0.015 (3)0.0001 (19)0.001 (2)0.000 (2)
C22B0.011 (2)0.013 (2)0.020 (3)0.0019 (17)0.002 (2)0.004 (2)
C21B0.006 (2)0.014 (2)0.014 (3)0.0003 (16)0.0027 (19)0.002 (2)
C16B0.016 (3)0.021 (3)0.034 (4)0.002 (2)0.001 (2)0.000 (2)
C15B0.022 (3)0.021 (3)0.043 (4)0.006 (2)0.001 (3)0.002 (3)
C14B0.016 (3)0.033 (3)0.025 (3)0.010 (2)0.009 (2)0.009 (3)
C13B0.006 (2)0.041 (3)0.024 (3)0.002 (2)0.003 (2)0.006 (3)
C12B0.016 (3)0.020 (3)0.018 (3)0.0010 (18)0.001 (2)0.002 (2)
C11B0.009 (2)0.024 (3)0.012 (3)0.0011 (18)0.0027 (19)0.002 (2)
C280.017 (3)0.022 (3)0.010 (3)0.0007 (19)0.004 (2)0.001 (2)
C28B0.016 (3)0.022 (3)0.018 (3)0.0011 (19)0.001 (2)0.006 (2)
C290.013 (2)0.016 (2)0.020 (3)0.0001 (18)0.004 (2)0.001 (2)
C29B0.012 (2)0.023 (3)0.019 (3)0.0038 (19)0.009 (2)0.001 (2)
C310.014 (2)0.018 (2)0.006 (3)0.0031 (18)0.0025 (19)0.000 (2)
C320.011 (2)0.019 (3)0.023 (3)0.0024 (18)0.000 (2)0.003 (2)
C330.015 (3)0.023 (3)0.016 (3)0.0052 (19)0.003 (2)0.001 (2)
C340.028 (3)0.017 (3)0.006 (3)0.001 (2)0.002 (2)0.000 (2)
C350.022 (3)0.022 (3)0.016 (3)0.008 (2)0.004 (2)0.002 (2)
C360.020 (3)0.020 (3)0.010 (3)0.002 (2)0.006 (2)0.001 (2)
C410.010 (2)0.016 (2)0.025 (3)0.0033 (17)0.002 (2)0.003 (2)
C420.019 (3)0.045 (4)0.021 (3)0.007 (3)0.012 (2)0.013 (3)
C430.016 (3)0.046 (4)0.044 (5)0.010 (3)0.015 (3)0.012 (3)
C440.009 (3)0.033 (3)0.050 (5)0.001 (2)0.000 (3)0.016 (3)
C450.019 (3)0.037 (3)0.023 (4)0.001 (2)0.003 (2)0.010 (3)
C460.018 (3)0.027 (3)0.029 (4)0.000 (2)0.007 (2)0.001 (3)
C4B0.011 (2)0.018 (2)0.017 (3)0.0019 (18)0.007 (2)0.005 (2)
C31B0.014 (2)0.014 (2)0.014 (3)0.0010 (18)0.000 (2)0.001 (2)
C32B0.010 (2)0.027 (3)0.008 (3)0.0006 (19)0.004 (2)0.002 (2)
C33B0.019 (3)0.027 (3)0.013 (3)0.003 (2)0.004 (2)0.000 (2)
C34B0.020 (3)0.016 (3)0.023 (3)0.000 (2)0.000 (2)0.004 (2)
C35B0.022 (3)0.020 (3)0.022 (3)0.004 (2)0.006 (2)0.002 (2)
C36B0.011 (3)0.019 (3)0.026 (4)0.0009 (19)0.007 (2)0.001 (2)
C41B0.013 (2)0.010 (2)0.022 (3)0.0036 (17)0.002 (2)0.002 (2)
C42B0.015 (3)0.025 (3)0.029 (4)0.002 (2)0.003 (2)0.004 (3)
C43B0.014 (3)0.025 (3)0.039 (4)0.003 (2)0.018 (3)0.005 (3)
C44B0.019 (3)0.019 (3)0.024 (4)0.000 (2)0.001 (2)0.003 (2)
C45B0.016 (3)0.038 (3)0.030 (4)0.004 (2)0.001 (2)0.001 (3)
C46B0.012 (3)0.030 (3)0.023 (3)0.003 (2)0.001 (2)0.003 (2)
Geometric parameters (Å, º) top
Cu1—N31.957 (5)C23—C241.375 (8)
Cu1—P12.2348 (15)C23—H230.9500
Cu1—P22.2683 (14)C24—C251.395 (10)
Cu1—S12.4292 (15)C24—H240.9500
S1—C11.724 (6)C25—C261.382 (8)
S2—C41.634 (6)C25—H250.9500
P1—C211.817 (5)C26—H260.9500
P1—C11C1.82 (3)C27—C281.536 (7)
P1—C271.838 (6)C27—H27A0.9900
P1—C111.842 (17)C27—H27B0.9900
P2—C411.816 (6)C27B—C28B1.540 (7)
P2—C311.828 (5)C27B—H27C0.9900
P2—C291.852 (6)C27B—H27D0.9900
N1—C11.336 (7)C26B—C25B1.390 (8)
N1—C21.447 (10)C26B—C21B1.402 (8)
N1—H10.8800C26B—H26B0.9500
N2—C11.312 (8)C25B—C24B1.364 (10)
N2—C31.461 (8)C25B—H25B0.9500
N2—H20.8800C24B—C23B1.391 (8)
N3—C41.149 (8)C24B—H24B0.9500
C2—H2C0.9800C23B—C22B1.387 (8)
C2—H2D0.9800C23B—H23B0.9500
C2—H2E0.9800C22B—C21B1.379 (9)
S2B—C4B1.654 (6)C22B—H22B0.9500
C1B—N2B1.322 (12)C16B—C11B1.378 (8)
C1B—N1B1.332 (11)C16B—C15B1.395 (8)
C1B—S1B1.675 (14)C16B—H16B0.9500
N2B—C3B1.467 (11)C15B—C14B1.387 (9)
N2B—H2L0.8800C15B—H15B0.9500
C3B—H3BA0.9800C14B—C13B1.360 (9)
C3B—H3BB0.9800C14B—H14B0.9500
C3B—H3BC0.9800C13B—C12B1.391 (7)
N1B—C2B1.438 (14)C13B—H13B0.9500
N1B—H1B0.8800C12B—C11B1.402 (7)
C2B—H2F0.9800C12B—H12B0.9500
C2B—H2G0.9800C28—C291.537 (7)
C2B—H2H0.9800C28—H28A0.9900
C1C—N1C1.320 (18)C28—H28B0.9900
C1C—N2C1.335 (19)C28B—C29B1.551 (8)
C1C—S1B1.82 (3)C28B—H28C0.9900
N2C—C3C1.466 (18)C28B—H28D0.9900
N2C—H2M0.8800C29—H29A0.9900
C3C—H3BD0.9800C29—H29B0.9900
C3C—H3BE0.9800C29B—H29C0.9900
C3C—H3BF0.9800C29B—H29D0.9900
N1C—C2C1.43 (2)C31—C361.396 (8)
N1C—H1C0.8800C31—C321.397 (8)
C2C—H2I0.9800C32—C331.386 (8)
C2C—H2J0.9800C32—H320.9500
C2C—H2K0.9800C33—C341.367 (9)
P2B—C29B1.824 (6)C33—H330.9500
P2B—C31B1.827 (5)C34—C351.392 (9)
P2B—C41B1.836 (5)C34—H340.9500
P2B—Cu1B2.2688 (15)C35—C361.390 (8)
C3—H3A0.9800C35—H350.9500
C3—H3B0.9800C36—H360.9500
C3—H3C0.9800C41—C461.377 (9)
N3B—C4B1.152 (8)C41—C421.393 (9)
N3B—Cu1B1.954 (6)C42—C431.415 (9)
C11—C161.384 (14)C42—H420.9500
C11—C121.387 (12)C43—C441.378 (11)
C12—C131.412 (11)C43—H430.9500
C12—H120.9500C44—C451.354 (10)
C13—C141.358 (13)C44—H440.9500
C13—H130.9500C45—C461.388 (8)
C14—C151.387 (13)C45—H450.9500
C14—H140.9500C46—H460.9500
C15—C161.406 (11)C31B—C36B1.394 (8)
C15—H150.9500C31B—C32B1.403 (7)
C16—H160.9500C32B—C33B1.391 (8)
C11C—C16C1.379 (19)C32B—H32B0.9500
C11C—C12C1.389 (18)C33B—C34B1.391 (9)
C12C—C13C1.394 (18)C33B—H33B0.9500
C12C—H12C0.9500C34B—C35B1.392 (9)
C13C—C14C1.346 (19)C34B—H34B0.9500
C13C—H13C0.9500C35B—C36B1.390 (8)
C14C—C15C1.40 (2)C35B—H35B0.9500
C14C—H14C0.9500C36B—H36B0.9500
C15C—C16C1.411 (17)C41B—C42B1.388 (9)
C15C—H15C0.9500C41B—C46B1.391 (9)
C16C—H16C0.9500C42B—C43B1.395 (8)
C21—C221.387 (9)C42B—H42B0.9500
C21—C261.398 (8)C43B—C44B1.370 (10)
S1B—Cu1B2.3997 (17)C43B—H43B0.9500
Cu1B—P1B2.2363 (15)C44B—C45B1.386 (10)
P1B—C11B1.822 (5)C44B—H44B0.9500
P1B—C21B1.825 (5)C45B—C46B1.388 (8)
P1B—C27B1.845 (6)C45B—H45B0.9500
C22—C231.387 (7)C46B—H46B0.9500
C22—H220.9500
N3—Cu1—P1127.47 (14)C23—C24—H24120.2
N3—Cu1—P2120.47 (14)C25—C24—H24120.2
P1—Cu1—P298.95 (6)C26—C25—C24120.5 (6)
N3—Cu1—S1108.54 (15)C26—C25—H25119.8
P1—Cu1—S1101.73 (5)C24—C25—H25119.8
P2—Cu1—S193.27 (5)C25—C26—C21120.0 (6)
C1—S1—Cu1109.4 (2)C25—C26—H26120.0
C21—P1—C11C100.8 (10)C21—C26—H26120.0
C21—P1—C27105.0 (3)C28—C27—P1116.8 (4)
C11C—P1—C27100.9 (16)C28—C27—H27A108.1
C21—P1—C11101.7 (6)P1—C27—H27A108.1
C27—P1—C11104.0 (9)C28—C27—H27B108.1
C21—P1—Cu1116.34 (19)P1—C27—H27B108.1
C11C—P1—Cu1123.3 (10)H27A—C27—H27B107.3
C27—P1—Cu1108.22 (17)C28B—C27B—P1B116.9 (4)
C11—P1—Cu1120.0 (6)C28B—C27B—H27C108.1
C41—P2—C31104.5 (2)P1B—C27B—H27C108.1
C41—P2—C29105.5 (3)C28B—C27B—H27D108.1
C31—P2—C29100.2 (2)P1B—C27B—H27D108.1
C41—P2—Cu1114.79 (18)H27C—C27B—H27D107.3
C31—P2—Cu1123.29 (18)C25B—C26B—C21B118.8 (6)
C29—P2—Cu1106.41 (17)C25B—C26B—H26B120.6
C1—N1—C2123.9 (5)C21B—C26B—H26B120.6
C1—N1—H1118.0C24B—C25B—C26B121.5 (6)
C2—N1—H1118.0C24B—C25B—H25B119.2
C1—N2—C3124.6 (5)C26B—C25B—H25B119.2
C1—N2—H2117.7C25B—C24B—C23B119.9 (5)
C3—N2—H2117.7C25B—C24B—H24B120.1
C4—N3—Cu1171.7 (4)C23B—C24B—H24B120.1
N2—C1—N1119.7 (5)C22B—C23B—C24B119.3 (6)
N2—C1—S1120.2 (4)C22B—C23B—H23B120.3
N1—C1—S1120.1 (5)C24B—C23B—H23B120.3
N1—C2—H2C109.5C21B—C22B—C23B121.0 (5)
N1—C2—H2D109.5C21B—C22B—H22B119.5
H2C—C2—H2D109.5C23B—C22B—H22B119.5
N1—C2—H2E109.5C22B—C21B—C26B119.5 (5)
H2C—C2—H2E109.5C22B—C21B—P1B117.2 (4)
H2D—C2—H2E109.5C26B—C21B—P1B123.2 (5)
N2B—C1B—N1B118.9 (11)C11B—C16B—C15B121.1 (5)
N2B—C1B—S1B117.3 (9)C11B—C16B—H16B119.4
N1B—C1B—S1B123.8 (9)C15B—C16B—H16B119.4
C1B—N2B—C3B126.0 (11)C14B—C15B—C16B119.3 (5)
C1B—N2B—H2L117.0C14B—C15B—H15B120.3
C3B—N2B—H2L117.0C16B—C15B—H15B120.3
N2B—C3B—H3BA109.5C13B—C14B—C15B120.4 (5)
N2B—C3B—H3BB109.5C13B—C14B—H14B119.8
H3BA—C3B—H3BB109.5C15B—C14B—H14B119.8
N2B—C3B—H3BC109.5C14B—C13B—C12B120.5 (5)
H3BA—C3B—H3BC109.5C14B—C13B—H13B119.7
H3BB—C3B—H3BC109.5C12B—C13B—H13B119.7
C1B—N1B—C2B123.1 (11)C13B—C12B—C11B120.3 (5)
C1B—N1B—H1B118.4C13B—C12B—H12B119.9
C2B—N1B—H1B118.4C11B—C12B—H12B119.9
N1B—C2B—H2F109.5C16B—C11B—C12B118.4 (5)
N1B—C2B—H2G109.5C16B—C11B—P1B119.4 (4)
H2F—C2B—H2G109.5C12B—C11B—P1B122.2 (4)
N1B—C2B—H2H109.5C27—C28—C29116.8 (5)
H2F—C2B—H2H109.5C27—C28—H28A108.1
H2G—C2B—H2H109.5C29—C28—H28A108.1
N1C—C1C—N2C119 (2)C27—C28—H28B108.1
N1C—C1C—S1B115.5 (16)C29—C28—H28B108.1
N2C—C1C—S1B125.0 (17)H28A—C28—H28B107.3
C1C—N2C—C3C122 (2)C27B—C28B—C29B115.5 (5)
C1C—N2C—H2M119.2C27B—C28B—H28C108.4
C3C—N2C—H2M119.2C29B—C28B—H28C108.4
N2C—C3C—H3BD109.5C27B—C28B—H28D108.4
N2C—C3C—H3BE109.5C29B—C28B—H28D108.4
H3BD—C3C—H3BE109.5H28C—C28B—H28D107.5
N2C—C3C—H3BF109.5C28—C29—P2112.9 (4)
H3BD—C3C—H3BF109.5C28—C29—H29A109.0
H3BE—C3C—H3BF109.5P2—C29—H29A109.0
C1C—N1C—C2C125 (2)C28—C29—H29B109.0
C1C—N1C—H1C117.4P2—C29—H29B109.0
C2C—N1C—H1C117.4H29A—C29—H29B107.8
N1C—C2C—H2I109.5C28B—C29B—P2B114.3 (4)
N1C—C2C—H2J109.5C28B—C29B—H29C108.7
H2I—C2C—H2J109.5P2B—C29B—H29C108.7
N1C—C2C—H2K109.5C28B—C29B—H29D108.7
H2I—C2C—H2K109.5P2B—C29B—H29D108.7
H2J—C2C—H2K109.5H29C—C29B—H29D107.6
C29B—P2B—C31B101.1 (3)C36—C31—C32119.1 (5)
C29B—P2B—C41B104.8 (3)C36—C31—P2122.2 (4)
C31B—P2B—C41B103.3 (2)C32—C31—P2118.5 (4)
C29B—P2B—Cu1B106.01 (17)C33—C32—C31120.4 (5)
C31B—P2B—Cu1B125.14 (19)C33—C32—H32119.8
C41B—P2B—Cu1B114.14 (17)C31—C32—H32119.8
N2—C3—H3A109.5C34—C33—C32120.7 (6)
N2—C3—H3B109.5C34—C33—H33119.7
H3A—C3—H3B109.5C32—C33—H33119.7
N2—C3—H3C109.5C33—C34—C35119.4 (5)
H3A—C3—H3C109.5C33—C34—H34120.3
H3B—C3—H3C109.5C35—C34—H34120.3
C4B—N3B—Cu1B165.8 (5)C36—C35—C34120.9 (5)
N3—C4—S2178.5 (5)C36—C35—H35119.6
C16—C11—C12120.1 (12)C34—C35—H35119.6
C16—C11—P1118.2 (11)C35—C36—C31119.5 (6)
C12—C11—P1121.6 (10)C35—C36—H36120.3
C11—C12—C13119.5 (11)C31—C36—H36120.3
C11—C12—H12120.2C46—C41—C42118.1 (5)
C13—C12—H12120.2C46—C41—P2117.3 (5)
C14—C13—C12120.5 (11)C42—C41—P2124.5 (5)
C14—C13—H13119.8C41—C42—C43120.0 (6)
C12—C13—H13119.8C41—C42—H42120.0
C13—C14—C15120.0 (11)C43—C42—H42120.0
C13—C14—H14120.0C44—C43—C42119.6 (6)
C15—C14—H14120.0C44—C43—H43120.2
C14—C15—C16120.2 (10)C42—C43—H43120.2
C14—C15—H15119.9C45—C44—C43120.3 (6)
C16—C15—H15119.9C45—C44—H44119.8
C11—C16—C15119.5 (10)C43—C44—H44119.8
C11—C16—H16120.3C44—C45—C46120.3 (7)
C15—C16—H16120.3C44—C45—H45119.9
C16C—C11C—C12C120 (2)C46—C45—H45119.9
C16C—C11C—P1119.5 (19)C41—C46—C45121.7 (6)
C12C—C11C—P1121.0 (19)C41—C46—H46119.2
C11C—C12C—C13C119.9 (19)C45—C46—H46119.2
C11C—C12C—H12C120.1N3B—C4B—S2B178.5 (5)
C13C—C12C—H12C120.1C36B—C31B—C32B118.9 (5)
C14C—C13C—C12C120.5 (19)C36B—C31B—P2B122.2 (4)
C14C—C13C—H13C119.7C32B—C31B—P2B118.8 (4)
C12C—C13C—H13C119.7C33B—C32B—C31B120.4 (5)
C13C—C14C—C15C121 (2)C33B—C32B—H32B119.8
C13C—C14C—H14C119.4C31B—C32B—H32B119.8
C15C—C14C—H14C119.4C34B—C33B—C32B119.6 (5)
C14C—C15C—C16C118.1 (17)C34B—C33B—H33B120.2
C14C—C15C—H15C120.9C32B—C33B—H33B120.2
C16C—C15C—H15C120.9C33B—C34B—C35B120.6 (5)
C11C—C16C—C15C120.3 (18)C33B—C34B—H34B119.7
C11C—C16C—H16C119.8C35B—C34B—H34B119.7
C15C—C16C—H16C119.8C36B—C35B—C34B119.4 (5)
C22—C21—C26118.9 (5)C36B—C35B—H35B120.3
C22—C21—P1116.8 (4)C34B—C35B—H35B120.3
C26—C21—P1124.3 (5)C35B—C36B—C31B120.9 (5)
C1B—S1B—Cu1B111.4 (5)C35B—C36B—H36B119.5
C1C—S1B—Cu1B103.0 (10)C31B—C36B—H36B119.5
N3B—Cu1B—P1B127.96 (15)C42B—C41B—C46B119.7 (5)
N3B—Cu1B—P2B120.23 (15)C42B—C41B—P2B124.1 (5)
P1B—Cu1B—P2B99.20 (6)C46B—C41B—P2B116.2 (4)
N3B—Cu1B—S1B108.75 (15)C41B—C42B—C43B119.6 (6)
P1B—Cu1B—S1B99.28 (6)C41B—C42B—H42B120.2
P2B—Cu1B—S1B94.95 (6)C43B—C42B—H42B120.2
C11B—P1B—C21B103.2 (2)C44B—C43B—C42B120.9 (6)
C11B—P1B—C27B102.0 (3)C44B—C43B—H43B119.5
C21B—P1B—C27B105.6 (3)C42B—C43B—H43B119.5
C11B—P1B—Cu1B121.51 (19)C43B—C44B—C45B119.3 (6)
C21B—P1B—Cu1B114.00 (19)C43B—C44B—H44B120.3
C27B—P1B—Cu1B108.87 (18)C45B—C44B—H44B120.3
C23—C22—C21120.9 (5)C44B—C45B—C46B120.7 (7)
C23—C22—H22119.6C44B—C45B—H45B119.6
C21—C22—H22119.6C46B—C45B—H45B119.6
C24—C23—C22120.1 (6)C45B—C46B—C41B119.7 (6)
C24—C23—H23119.9C45B—C46B—H46B120.2
C22—C23—H23119.9C41B—C46B—H46B120.2
C23—C24—C25119.6 (5)
C3—N2—C1—N13.0 (9)Cu1B—P1B—C21B—C26B129.4 (4)
C3—N2—C1—S1177.9 (5)C11B—C16B—C15B—C14B0.6 (11)
C2—N1—C1—N2178.9 (6)C16B—C15B—C14B—C13B0.4 (11)
C2—N1—C1—S12.0 (8)C15B—C14B—C13B—C12B0.0 (10)
Cu1—S1—C1—N224.5 (5)C14B—C13B—C12B—C11B0.4 (10)
Cu1—S1—C1—N1156.4 (4)C15B—C16B—C11B—C12B0.3 (10)
N1B—C1B—N2B—C3B3 (2)C15B—C16B—C11B—P1B179.6 (6)
S1B—C1B—N2B—C3B177.5 (10)C13B—C12B—C11B—C16B0.2 (9)
N2B—C1B—N1B—C2B172.5 (16)C13B—C12B—C11B—P1B179.9 (5)
S1B—C1B—N1B—C2B7 (3)C21B—P1B—C11B—C16B159.8 (5)
N1C—C1C—N2C—C3C3 (4)C27B—P1B—C11B—C16B90.8 (5)
S1B—C1C—N2C—C3C173 (2)Cu1B—P1B—C11B—C16B30.4 (6)
N2C—C1C—N1C—C2C176 (3)C21B—P1B—C11B—C12B20.1 (6)
S1B—C1C—N1C—C2C5 (4)C27B—P1B—C11B—C12B89.4 (5)
C21—P1—C11—C16139.8 (17)Cu1B—P1B—C11B—C12B149.4 (4)
C27—P1—C11—C16111.3 (18)P1—C27—C28—C2970.8 (6)
Cu1—P1—C11—C1610 (2)P1B—C27B—C28B—C29B69.2 (6)
C21—P1—C11—C1236.9 (16)C27—C28—C29—P274.9 (6)
C27—P1—C11—C1272.0 (15)C41—P2—C29—C28175.3 (4)
Cu1—P1—C11—C12166.9 (12)C31—P2—C29—C2867.0 (4)
C16—C11—C12—C130.8 (19)Cu1—P2—C29—C2862.3 (4)
P1—C11—C12—C13177.4 (17)C27B—C28B—C29B—P2B75.8 (6)
C11—C12—C13—C143.6 (16)C31B—P2B—C29B—C28B68.3 (4)
C12—C13—C14—C156 (3)C41B—P2B—C29B—C28B175.4 (4)
C13—C14—C15—C164 (3)Cu1B—P2B—C29B—C28B63.5 (4)
C12—C11—C16—C153 (2)C41—P2—C31—C3645.9 (5)
P1—C11—C16—C15179.3 (12)C29—P2—C31—C3663.2 (5)
C14—C15—C16—C110 (2)Cu1—P2—C31—C36179.3 (4)
C21—P1—C11C—C16C161 (3)C41—P2—C31—C32139.8 (5)
C27—P1—C11C—C16C91 (3)C29—P2—C31—C32111.1 (5)
Cu1—P1—C11C—C16C29 (4)Cu1—P2—C31—C326.4 (5)
C21—P1—C11C—C12C17 (3)C36—C31—C32—C330.8 (9)
C27—P1—C11C—C12C91 (3)P2—C31—C32—C33173.6 (5)
Cu1—P1—C11C—C12C149 (2)C31—C32—C33—C340.5 (9)
C16C—C11C—C12C—C13C1 (3)C32—C33—C34—C350.5 (9)
P1—C11C—C12C—C13C179 (4)C33—C34—C35—C361.2 (9)
C11C—C12C—C13C—C14C1 (3)C34—C35—C36—C310.8 (9)
C12C—C13C—C14C—C15C4 (5)C32—C31—C36—C350.2 (9)
C13C—C14C—C15C—C16C7 (5)P2—C31—C36—C35174.1 (5)
C12C—C11C—C16C—C15C4 (4)C31—P2—C41—C4682.7 (5)
P1—C11C—C16C—C15C178 (2)C29—P2—C41—C46172.2 (4)
C14C—C15C—C16C—C11C7 (4)Cu1—P2—C41—C4655.4 (5)
C11C—P1—C21—C2285.8 (16)C31—P2—C41—C42100.3 (5)
C27—P1—C21—C22169.7 (4)C29—P2—C41—C424.8 (6)
C11—P1—C21—C2282.2 (9)Cu1—P2—C41—C42121.7 (5)
Cu1—P1—C21—C2250.1 (4)C46—C41—C42—C430.1 (9)
C11C—P1—C21—C2694.4 (16)P2—C41—C42—C43177.0 (5)
C27—P1—C21—C2610.1 (5)C41—C42—C43—C440.3 (10)
C11—P1—C21—C2698.1 (10)C42—C43—C44—C450.3 (10)
Cu1—P1—C21—C26129.7 (4)C43—C44—C45—C460.1 (10)
N2B—C1B—S1B—Cu1B28.9 (17)C42—C41—C46—C450.5 (9)
N1B—C1B—S1B—Cu1B151.7 (15)P2—C41—C46—C45176.7 (5)
N1C—C1C—S1B—Cu1B142 (3)C44—C45—C46—C410.5 (9)
N2C—C1C—S1B—Cu1B48 (3)C29B—P2B—C31B—C36B66.2 (5)
C26—C21—C22—C230.7 (8)C41B—P2B—C31B—C36B42.1 (6)
P1—C21—C22—C23179.1 (4)Cu1B—P2B—C31B—C36B175.0 (4)
C21—C22—C23—C240.5 (8)C29B—P2B—C31B—C32B110.8 (5)
C22—C23—C24—C251.3 (8)C41B—P2B—C31B—C32B140.9 (5)
C23—C24—C25—C261.0 (9)Cu1B—P2B—C31B—C32B8.0 (5)
C24—C25—C26—C210.2 (9)C36B—C31B—C32B—C33B2.7 (8)
C22—C21—C26—C251.1 (8)P2B—C31B—C32B—C33B174.4 (4)
P1—C21—C26—C25178.7 (4)C31B—C32B—C33B—C34B2.8 (8)
C21—P1—C27—C2870.4 (4)C32B—C33B—C34B—C35B1.3 (9)
C11C—P1—C27—C28174.8 (9)C33B—C34B—C35B—C36B0.2 (10)
C11—P1—C27—C28176.8 (6)C34B—C35B—C36B—C31B0.3 (10)
Cu1—P1—C27—C2854.5 (4)C32B—C31B—C36B—C35B1.2 (9)
C11B—P1B—C27B—C28B177.2 (4)P2B—C31B—C36B—C35B175.8 (5)
C21B—P1B—C27B—C28B69.6 (4)C29B—P2B—C41B—C42B6.2 (5)
Cu1B—P1B—C27B—C28B53.1 (4)C31B—P2B—C41B—C42B99.3 (5)
C21B—C26B—C25B—C24B1.5 (9)Cu1B—P2B—C41B—C42B121.7 (4)
C26B—C25B—C24B—C23B1.0 (9)C29B—P2B—C41B—C46B171.4 (4)
C25B—C24B—C23B—C22B0.4 (8)C31B—P2B—C41B—C46B83.1 (5)
C24B—C23B—C22B—C21B0.4 (8)Cu1B—P2B—C41B—C46B55.8 (4)
C23B—C22B—C21B—C26B0.9 (8)C46B—C41B—C42B—C43B0.7 (8)
C23B—C22B—C21B—P1B175.4 (4)P2B—C41B—C42B—C43B178.2 (4)
C25B—C26B—C21B—C22B1.4 (8)C41B—C42B—C43B—C44B0.3 (9)
C25B—C26B—C21B—P1B174.6 (4)C42B—C43B—C44B—C45B0.9 (9)
C11B—P1B—C21B—C22B87.1 (4)C43B—C44B—C45B—C46B1.8 (9)
C27B—P1B—C21B—C22B166.2 (4)C44B—C45B—C46B—C41B2.3 (9)
Cu1B—P1B—C21B—C22B46.7 (4)C42B—C41B—C46B—C45B1.7 (8)
C11B—P1B—C21B—C26B96.8 (5)P2B—C41B—C46B—C45B179.4 (5)
C27B—P1B—C21B—C26B10.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S2Bi0.882.643.466 (5)158
N2—H2···N30.882.323.174 (7)165
N2B—H2L···N3B0.882.433.286 (13)164
N1B—H1B···S10.882.553.350 (13)151
N2C—H2M···N3B0.882.503.24 (2)142
N1C—H1C···S10.882.583.34 (2)146
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S2Bi0.882.643.466 (5)157.6
N2—H2···N30.882.323.174 (7)164.5
N2B—H2L···N3B0.882.433.286 (13)164.3
N1B—H1B···S10.882.553.350 (13)151.0
N2C—H2M···N3B0.882.503.24 (2)141.5
N1C—H1C···S10.882.583.34 (2)146.0
Symmetry code: (i) x+1, y, z.
 

Acknowledgements

Financial support from the Department of Chemistry, Prince of Songkla University, is gratefully acknowledged. We would like to thank Dr Matthias Zeller for valuable suggestions and assistance with the X-ray structure determination and use of structure refinement programs.

References

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Volume 71| Part 3| March 2015| Pages m61-m62
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