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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): m690.
Published online 2010 May 22. doi:  10.1107/S1600536810018325
PMCID: PMC2979374

Bis[(4-chloro­benz­yl)triphenyl­phospho­nium] tetra­chloridozincate(II) trihydrate

Abstract

The crystal structure of the title compound, (C25H21ClP)2[ZnCl4]·3H2O, consists of tetra­hedral phosphonium cations and tetra­hedral zincate anions; the water mol­ecules form weak hydrogen bonds to the anions. Two of the water mol­ecules are disordered over three sites in a 0.68:0.55:0.77 ratio.

Related literature

For background to phospho­nium tetrahalogenidozincates, see: Bruni et al. (1992 [triangle]). For the crystal structures of two related zincates, see: Aliev et al. (1988 [triangle]); Pattacini et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m690-scheme1.jpg

Experimental

Crystal data

  • (C25H21ClP)2[ZnCl4]·3H2O
  • M r = 1036.89
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m690-efi1.jpg
  • a = 11.2634 (12) Å
  • b = 14.2995 (15) Å
  • c = 16.9288 (17) Å
  • α = 73.651 (1)°
  • β = 73.527 (2)°
  • γ = 68.205 (2)°
  • V = 2379.7 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.96 mm−1
  • T = 100 K
  • 0.15 × 0.10 × 0.03 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.869, T max = 0.972
  • 23163 measured reflections
  • 10895 independent reflections
  • 6579 reflections with I > 2σ(I)
  • R int = 0.064

Refinement

  • R[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.164
  • S = 1.00
  • 10895 reflections
  • 568 parameters
  • 18 restraints
  • H-atom parameters constrained
  • Δρmax = 1.16 e Å−3
  • Δρmin = −0.82 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810018325/bt5270sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018325/bt5270Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the MOHE (FRGS–FP001/2009) for supporting this study. KWT thanks the Ministry of Higher Education for an SLAI scholarship.

supplementary crystallographic information

Comment

From far infrared spectral measurements, the anion of the salt, bis[benzyltriphenylphosphonium] tetrachloridozincate, was assigned an ion-pair structure with the cation and anion existing in tetrahedral geometries (Bruni et al., 1992). A earlier synthesis yielded instead the hexachlorodizincate salt, whose formulation was confirmed by crystal structure analysis (Aliev et al., 1988). With the (4-chlorobenzyl)triphenylphosphonium cation, the salt is a tetrachlorozincate; however, the salt this crystallizes as a trihydrate (Scheme I, Fig. 1). The crystal structure consists of tetrahedral cations and tetrahedral anions, with the lattice water molecules being only weakly connected to the anions.

Experimental

Zinc chloride (0.14 g, 1 mmol) and (4-chlorobenzyl)triphenylphosphonium chloride (0.84 g, 2 mmol) were heated in an ethanol and water mixture ( 3:1, 20 ml) for 3 hours. The yellow compound that separated upon slow evaporation of the solution was recrystallized from a mixture of ethanol and DMF.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95–0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

Tow of the three water molecules are disordered over three positions (O2w, O3w, O4w). As their occupancies refined to nearly 0.68:0.55:0.77, the occupancies were fixed at these values. The anisotropic temperature factors of all water molecules were restrained to be nearly isotropic. Hydrogen atoms were placed in chemically-sensible positions on the basis of possible O–H···Cl interactions; these are weak. For O2w, one of its hydrogen atoms occupies the same site as O3w, and for O3w, one of its hydrogen atoms occupes the same site as O2w.

The final difference Fourier map had only one somewhat large peak near O4w but was otherwise featureless.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of (C25 H21ClP)2(ZnCl4).3H2O; ellipsoids are drawn at the 50% probability level and H atoms are of arbitrary radius. The disorder in the water molecules is not shown.

Crystal data

(C25H21ClP)2[ZnCl4]·3H2OZ = 2
Mr = 1036.89F(000) = 1068
Triclinic, P1Dx = 1.447 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.2634 (12) ÅCell parameters from 2585 reflections
b = 14.2995 (15) Åθ = 2.5–24.6°
c = 16.9288 (17) ŵ = 0.96 mm1
α = 73.651 (1)°T = 100 K
β = 73.527 (2)°Prism, yellow
γ = 68.205 (2)°0.15 × 0.10 × 0.03 mm
V = 2379.7 (4) Å3

Data collection

Bruker SMART APEX diffractometer10895 independent reflections
Radiation source: fine-focus sealed tube6579 reflections with I > 2σ(I)
graphiteRint = 0.064
ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −14→14
Tmin = 0.869, Tmax = 0.972k = −17→18
23163 measured reflectionsl = −21→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0725P)2 + 0.642P] where P = (Fo2 + 2Fc2)/3
10895 reflections(Δ/σ)max = 0.001
568 parametersΔρmax = 1.16 e Å3
18 restraintsΔρmin = −0.82 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Zn10.39614 (5)0.84375 (4)0.28532 (3)0.02513 (15)
Cl10.21085 (13)0.86435 (11)0.38977 (8)0.0408 (3)
Cl20.40060 (15)0.72339 (10)0.22031 (8)0.0422 (3)
Cl30.40802 (12)0.99004 (9)0.18953 (7)0.0305 (3)
Cl40.57229 (10)0.78183 (9)0.34554 (7)0.0256 (3)
Cl50.84826 (11)0.43139 (8)−0.02489 (8)0.0289 (3)
Cl61.00321 (12)0.47193 (12)0.24586 (9)0.0439 (4)
P10.80632 (10)0.91395 (8)0.01410 (7)0.0164 (2)
P20.44814 (10)0.31622 (9)0.40672 (7)0.0172 (2)
O1w0.3019 (3)0.6091 (3)0.4044 (2)0.0357 (8)
H1w10.26790.66680.41820.054*
H1w20.33830.61830.35340.054*
O2w0.1837 (9)1.1168 (7)0.3434 (6)0.071 (2)0.68
H2w10.20381.05400.34370.106*0.68
H2w20.22661.14370.29970.106*0.68
O3w0.2158 (17)1.1580 (12)0.3051 (10)0.131 (6)0.55
H3w10.17911.12220.34590.197*0.55
H3w20.26761.11960.27200.197*0.55
O4w0.0156 (13)1.0658 (10)0.4421 (8)0.215 (6)0.77
H4w10.07391.02250.41540.322*0.77
H4w2−0.04621.09550.41620.322*0.77
C10.8966 (4)0.8405 (3)0.0951 (3)0.0165 (9)
C21.0319 (4)0.8094 (3)0.0784 (3)0.0181 (9)
H21.07910.82120.02230.022*
C31.0979 (4)0.7607 (3)0.1443 (3)0.0218 (10)
H31.19050.73970.13320.026*
C41.0296 (4)0.7425 (3)0.2259 (3)0.0221 (10)
H41.07550.70860.27050.027*
C50.8946 (4)0.7736 (3)0.2428 (3)0.0212 (10)
H50.84810.76100.29900.025*
C60.8273 (4)0.8231 (3)0.1778 (3)0.0202 (9)
H60.73460.84510.18940.024*
C70.7331 (4)1.0437 (3)0.0293 (3)0.0177 (9)
C80.7498 (4)1.0733 (3)0.0960 (3)0.0187 (9)
H80.80531.02500.13220.022*
C90.6865 (4)1.1723 (3)0.1099 (3)0.0212 (10)
H90.69781.19190.15580.025*
C100.6062 (4)1.2427 (3)0.0563 (3)0.0224 (10)
H100.56191.31070.06590.027*
C110.5903 (4)1.2146 (3)−0.0107 (3)0.0219 (10)
H110.53641.2637−0.04760.026*
C120.6518 (4)1.1160 (3)−0.0243 (3)0.0188 (9)
H120.63941.0968−0.07000.023*
C130.9112 (4)0.9036 (3)−0.0868 (3)0.0162 (9)
C140.9176 (4)0.9902 (4)−0.1498 (3)0.0226 (10)
H140.86811.0569−0.13870.027*
C150.9958 (4)0.9791 (4)−0.2285 (3)0.0252 (10)
H151.00061.0383−0.27090.030*
C161.0669 (4)0.8823 (4)−0.2454 (3)0.0270 (11)
H161.12060.8747−0.29930.032*
C171.0593 (4)0.7961 (4)−0.1833 (3)0.0235 (10)
H171.10710.7295−0.19500.028*
C180.9830 (4)0.8068 (3)−0.1046 (3)0.0202 (9)
H180.97950.7474−0.06230.024*
C190.6724 (4)0.8668 (3)0.0237 (3)0.0212 (10)
H19A0.61550.87140.08000.025*
H19B0.61950.9116−0.01870.025*
C200.7178 (4)0.7573 (3)0.0118 (3)0.0190 (9)
C210.7489 (4)0.6754 (3)0.0778 (3)0.0238 (10)
H210.74130.68830.13140.029*
C220.7906 (5)0.5755 (4)0.0667 (3)0.0273 (11)
H220.81350.51960.11170.033*
C230.7986 (4)0.5579 (3)−0.0108 (3)0.0221 (10)
C240.7664 (4)0.6377 (3)−0.0771 (3)0.0211 (10)
H240.77140.6245−0.13010.025*
C250.7269 (4)0.7367 (3)−0.0653 (3)0.0211 (10)
H250.70540.7922−0.11090.025*
C260.2848 (4)0.3235 (3)0.4640 (3)0.0187 (9)
C270.2169 (4)0.3938 (4)0.5163 (3)0.0240 (10)
H270.25750.43720.52420.029*
C280.0892 (4)0.4003 (4)0.5570 (3)0.0291 (11)
H280.04190.44850.59260.035*
C290.0302 (4)0.3359 (4)0.5457 (3)0.0305 (12)
H29−0.05710.34020.57380.037*
C300.0983 (4)0.2664 (4)0.4939 (3)0.0306 (11)
H300.05800.22280.48610.037*
C310.2262 (4)0.2597 (4)0.4527 (3)0.0270 (11)
H310.27330.21150.41700.032*
C320.5400 (4)0.1858 (3)0.3999 (3)0.0186 (9)
C330.5334 (4)0.1442 (3)0.3363 (3)0.0225 (10)
H330.48720.18740.29350.027*
C340.5935 (4)0.0411 (4)0.3354 (3)0.0260 (10)
H340.58670.01300.29280.031*
C350.6635 (4)−0.0215 (4)0.3963 (3)0.0266 (11)
H350.7057−0.09240.39520.032*
C360.6728 (5)0.0184 (4)0.4591 (3)0.0283 (11)
H360.7222−0.02490.50030.034*
C370.6099 (4)0.1214 (3)0.4618 (3)0.0238 (10)
H370.61430.14830.50580.029*
C380.4406 (4)0.3890 (3)0.3018 (3)0.0172 (9)
C390.5555 (4)0.3843 (3)0.2417 (3)0.0226 (10)
H390.63720.34210.25600.027*
C400.5502 (5)0.4410 (4)0.1614 (3)0.0279 (11)
H400.62860.43810.12050.034*
C410.4312 (5)0.5023 (3)0.1397 (3)0.0269 (11)
H410.42800.54110.08420.032*
C420.3169 (5)0.5067 (3)0.1995 (3)0.0248 (10)
H420.23540.54840.18470.030*
C430.3207 (4)0.4506 (3)0.2806 (3)0.0221 (10)
H430.24220.45410.32140.026*
C440.5220 (4)0.3699 (3)0.4574 (3)0.0201 (9)
H44A0.45710.43420.47320.024*
H44B0.54320.32110.50980.024*
C450.6443 (4)0.3932 (3)0.4048 (3)0.0180 (9)
C460.7670 (4)0.3166 (4)0.3986 (3)0.0222 (10)
H460.77430.24810.42810.027*
C470.8776 (4)0.3408 (4)0.3496 (3)0.0272 (11)
H470.96080.28940.34510.033*
C480.8645 (4)0.4404 (4)0.3075 (3)0.0255 (11)
C490.7463 (4)0.5175 (4)0.3128 (3)0.0261 (10)
H490.74000.58600.28390.031*
C500.6373 (4)0.4922 (3)0.3612 (3)0.0199 (9)
H500.55480.54430.36480.024*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0277 (3)0.0273 (3)0.0197 (3)−0.0064 (2)−0.0081 (2)−0.0036 (2)
Cl10.0356 (7)0.0486 (9)0.0346 (8)−0.0098 (6)−0.0089 (6)−0.0055 (6)
Cl20.0713 (10)0.0370 (8)0.0281 (7)−0.0240 (7)−0.0180 (7)−0.0040 (6)
Cl30.0436 (7)0.0241 (6)0.0228 (6)−0.0078 (5)−0.0130 (5)−0.0009 (5)
Cl40.0240 (5)0.0269 (6)0.0229 (6)−0.0062 (5)−0.0070 (4)−0.0002 (5)
Cl50.0349 (6)0.0157 (6)0.0341 (7)−0.0043 (5)−0.0100 (5)−0.0038 (5)
Cl60.0323 (7)0.0622 (10)0.0424 (8)−0.0276 (7)0.0140 (6)−0.0226 (7)
P10.0163 (5)0.0170 (6)0.0162 (6)−0.0039 (4)−0.0041 (4)−0.0048 (5)
P20.0170 (5)0.0177 (6)0.0163 (6)−0.0050 (4)−0.0028 (4)−0.0038 (5)
O1w0.0296 (18)0.035 (2)0.036 (2)−0.0071 (15)0.0008 (15)−0.0087 (17)
O2w0.074 (5)0.066 (5)0.075 (5)−0.003 (4)−0.024 (4)−0.035 (4)
O3w0.135 (9)0.138 (10)0.131 (10)−0.038 (7)−0.033 (7)−0.040 (7)
O4w0.199 (9)0.251 (10)0.215 (9)−0.053 (7)−0.065 (7)−0.078 (7)
C10.021 (2)0.014 (2)0.017 (2)−0.0041 (17)−0.0069 (17)−0.0043 (17)
C20.020 (2)0.017 (2)0.018 (2)−0.0067 (17)−0.0010 (17)−0.0064 (18)
C30.023 (2)0.015 (2)0.027 (3)−0.0025 (18)−0.0071 (19)−0.0049 (19)
C40.026 (2)0.018 (2)0.021 (2)−0.0045 (18)−0.0101 (19)−0.0001 (19)
C50.031 (2)0.015 (2)0.014 (2)−0.0064 (18)−0.0043 (18)0.0016 (18)
C60.016 (2)0.019 (2)0.023 (2)−0.0039 (17)−0.0015 (18)−0.0068 (19)
C70.016 (2)0.021 (2)0.016 (2)−0.0055 (17)0.0007 (16)−0.0070 (18)
C80.016 (2)0.022 (2)0.018 (2)−0.0061 (17)−0.0030 (17)−0.0054 (19)
C90.021 (2)0.026 (2)0.019 (2)−0.0072 (19)−0.0002 (18)−0.011 (2)
C100.021 (2)0.017 (2)0.028 (3)−0.0043 (18)−0.0030 (19)−0.007 (2)
C110.016 (2)0.019 (2)0.026 (3)−0.0027 (17)−0.0052 (18)0.0002 (19)
C120.019 (2)0.023 (2)0.016 (2)−0.0092 (18)0.0001 (17)−0.0063 (19)
C130.018 (2)0.020 (2)0.014 (2)−0.0058 (17)−0.0063 (17)−0.0062 (18)
C140.021 (2)0.024 (2)0.022 (2)−0.0045 (19)−0.0044 (18)−0.007 (2)
C150.025 (2)0.032 (3)0.019 (2)−0.012 (2)−0.0032 (19)−0.002 (2)
C160.020 (2)0.044 (3)0.019 (2)−0.011 (2)−0.0007 (18)−0.012 (2)
C170.018 (2)0.031 (3)0.022 (2)−0.0011 (19)−0.0035 (18)−0.017 (2)
C180.019 (2)0.022 (2)0.021 (2)−0.0033 (18)−0.0081 (18)−0.0061 (19)
C190.020 (2)0.021 (2)0.023 (2)−0.0052 (18)−0.0077 (18)−0.0027 (19)
C200.016 (2)0.017 (2)0.025 (2)−0.0065 (17)−0.0047 (18)−0.0036 (19)
C210.031 (2)0.025 (3)0.019 (2)−0.014 (2)−0.0062 (19)−0.001 (2)
C220.041 (3)0.022 (3)0.024 (3)−0.017 (2)−0.015 (2)0.007 (2)
C230.023 (2)0.016 (2)0.027 (3)−0.0085 (18)−0.0034 (19)−0.0026 (19)
C240.026 (2)0.020 (2)0.019 (2)−0.0060 (18)−0.0047 (18)−0.0070 (19)
C250.023 (2)0.019 (2)0.021 (2)−0.0063 (18)−0.0066 (18)−0.0021 (19)
C260.018 (2)0.019 (2)0.017 (2)−0.0044 (17)−0.0057 (17)0.0007 (18)
C270.020 (2)0.029 (3)0.023 (3)−0.0060 (19)−0.0081 (19)−0.004 (2)
C280.022 (2)0.037 (3)0.021 (3)0.000 (2)−0.0045 (19)−0.007 (2)
C290.018 (2)0.049 (3)0.018 (3)−0.011 (2)−0.0052 (19)0.005 (2)
C300.026 (2)0.036 (3)0.032 (3)−0.016 (2)−0.010 (2)0.002 (2)
C310.031 (3)0.023 (3)0.027 (3)−0.011 (2)−0.003 (2)−0.004 (2)
C320.020 (2)0.019 (2)0.017 (2)−0.0048 (17)−0.0042 (17)−0.0042 (18)
C330.025 (2)0.022 (2)0.022 (2)−0.0065 (19)−0.0083 (19)−0.004 (2)
C340.033 (3)0.029 (3)0.020 (3)−0.012 (2)−0.003 (2)−0.009 (2)
C350.032 (3)0.018 (2)0.028 (3)−0.005 (2)−0.006 (2)−0.006 (2)
C360.034 (3)0.024 (3)0.025 (3)−0.004 (2)−0.011 (2)−0.002 (2)
C370.024 (2)0.025 (3)0.023 (3)−0.0075 (19)−0.0028 (19)−0.007 (2)
C380.025 (2)0.017 (2)0.012 (2)−0.0090 (18)−0.0023 (17)−0.0039 (17)
C390.020 (2)0.027 (3)0.024 (3)−0.0115 (19)−0.0007 (19)−0.010 (2)
C400.036 (3)0.034 (3)0.020 (3)−0.019 (2)0.001 (2)−0.009 (2)
C410.048 (3)0.019 (2)0.018 (2)−0.016 (2)−0.009 (2)−0.0003 (19)
C420.032 (2)0.020 (2)0.022 (3)−0.004 (2)−0.013 (2)−0.002 (2)
C430.025 (2)0.019 (2)0.020 (2)−0.0037 (18)−0.0031 (19)−0.0063 (19)
C440.022 (2)0.021 (2)0.018 (2)−0.0062 (18)−0.0043 (18)−0.0053 (19)
C450.023 (2)0.022 (2)0.014 (2)−0.0086 (18)−0.0075 (17)−0.0061 (18)
C460.024 (2)0.023 (2)0.021 (2)−0.0053 (19)−0.0082 (19)−0.006 (2)
C470.021 (2)0.035 (3)0.029 (3)−0.007 (2)−0.005 (2)−0.016 (2)
C480.023 (2)0.042 (3)0.020 (2)−0.018 (2)0.0044 (19)−0.016 (2)
C490.032 (3)0.027 (3)0.023 (3)−0.016 (2)−0.002 (2)−0.007 (2)
C500.021 (2)0.020 (2)0.019 (2)−0.0046 (18)−0.0058 (18)−0.0054 (19)

Geometric parameters (Å, °)

Zn1—Cl12.3049 (14)C19—H19B0.9900
Zn1—Cl22.2685 (14)C20—C251.385 (6)
Zn1—Cl32.2800 (13)C20—C211.387 (6)
Zn1—Cl42.2571 (12)C21—C221.379 (6)
Cl5—C231.749 (4)C21—H210.9500
Cl6—C481.752 (4)C22—C231.376 (6)
P1—C71.790 (4)C22—H220.9500
P1—C131.790 (4)C23—C241.377 (6)
P1—C11.790 (4)C24—C251.372 (6)
P1—C191.820 (4)C24—H240.9500
P2—C321.784 (4)C25—H250.9500
P2—C381.796 (4)C26—C311.387 (6)
P2—C261.799 (4)C26—C271.388 (6)
P2—C441.807 (4)C27—C281.389 (6)
O1w—H1w10.8401C27—H270.9500
O1w—H1w20.8400C28—C291.396 (7)
O2w—H2w10.8400C28—H280.9500
O2w—H2w20.8400C29—C301.375 (7)
O3w—H3w10.8399C29—H290.9500
O3w—H3w20.8400C30—C311.391 (6)
O4w—H4w10.8399C30—H300.9500
O4w—H4w20.8400C31—H310.9500
C1—C21.387 (6)C32—C371.396 (6)
C1—C61.400 (6)C32—C331.399 (6)
C2—C31.390 (6)C33—C341.378 (6)
C2—H20.9500C33—H330.9500
C3—C41.382 (6)C34—C351.380 (6)
C3—H30.9500C34—H340.9500
C4—C51.383 (6)C35—C361.382 (6)
C4—H40.9500C35—H350.9500
C5—C61.387 (6)C36—C371.385 (6)
C5—H50.9500C36—H360.9500
C6—H60.9500C37—H370.9500
C7—C81.391 (6)C38—C391.393 (6)
C7—C121.405 (6)C38—C431.394 (6)
C8—C91.382 (6)C39—C401.378 (6)
C8—H80.9500C39—H390.9500
C9—C101.390 (6)C40—C411.387 (7)
C9—H90.9500C40—H400.9500
C10—C111.381 (6)C41—C421.386 (7)
C10—H100.9500C41—H410.9500
C11—C121.374 (6)C42—C431.385 (6)
C11—H110.9500C42—H420.9500
C12—H120.9500C43—H430.9500
C13—C181.388 (6)C44—C451.510 (6)
C13—C141.398 (6)C44—H44A0.9900
C14—C151.388 (6)C44—H44B0.9900
C14—H140.9500C45—C501.385 (6)
C15—C161.382 (6)C45—C461.406 (6)
C15—H150.9500C46—C471.391 (6)
C16—C171.389 (7)C46—H460.9500
C16—H160.9500C47—C481.375 (7)
C17—C181.379 (6)C47—H470.9500
C17—H170.9500C48—C491.376 (6)
C18—H180.9500C49—C501.379 (6)
C19—C201.509 (6)C49—H490.9500
C19—H19A0.9900C50—H500.9500
Cl4—Zn1—Cl2108.29 (5)C23—C22—H22120.5
Cl4—Zn1—Cl3108.25 (5)C21—C22—H22120.5
Cl2—Zn1—Cl3110.16 (5)C22—C23—C24121.5 (4)
Cl4—Zn1—Cl1108.61 (5)C22—C23—Cl5119.2 (3)
Cl2—Zn1—Cl1106.56 (6)C24—C23—Cl5119.3 (3)
Cl3—Zn1—Cl1114.79 (5)C25—C24—C23118.8 (4)
C7—P1—C13112.9 (2)C25—C24—H24120.6
C7—P1—C1108.51 (19)C23—C24—H24120.6
C13—P1—C1109.85 (19)C24—C25—C20121.3 (4)
C7—P1—C19106.25 (19)C24—C25—H25119.4
C13—P1—C19109.2 (2)C20—C25—H25119.4
C1—P1—C19110.1 (2)C31—C26—C27120.4 (4)
C32—P2—C38107.93 (19)C31—C26—P2118.6 (3)
C32—P2—C26109.4 (2)C27—C26—P2120.9 (3)
C38—P2—C26108.72 (19)C26—C27—C28119.5 (4)
C32—P2—C44111.9 (2)C26—C27—H27120.3
C38—P2—C44109.3 (2)C28—C27—H27120.3
C26—P2—C44109.7 (2)C27—C28—C29120.1 (5)
H1w1—O1w—H1w2107.7C27—C28—H28119.9
H2w1—O2w—H2w2108.8C29—C28—H28119.9
H3w1—O3w—H3w2108.2C30—C29—C28120.0 (4)
H4w1—O4w—H4w2109.0C30—C29—H29120.0
C2—C1—C6120.2 (4)C28—C29—H29120.0
C2—C1—P1121.3 (3)C29—C30—C31120.2 (5)
C6—C1—P1118.3 (3)C29—C30—H30119.9
C1—C2—C3119.4 (4)C31—C30—H30119.9
C1—C2—H2120.3C26—C31—C30119.8 (4)
C3—C2—H2120.3C26—C31—H31120.1
C4—C3—C2120.5 (4)C30—C31—H31120.1
C4—C3—H3119.8C37—C32—C33119.0 (4)
C2—C3—H3119.8C37—C32—P2120.7 (3)
C3—C4—C5120.2 (4)C33—C32—P2120.0 (3)
C3—C4—H4119.9C34—C33—C32120.5 (4)
C5—C4—H4119.9C34—C33—H33119.8
C4—C5—C6120.0 (4)C32—C33—H33119.8
C4—C5—H5120.0C33—C34—C35120.0 (4)
C6—C5—H5120.0C33—C34—H34120.0
C5—C6—C1119.7 (4)C35—C34—H34120.0
C5—C6—H6120.2C34—C35—C36120.4 (4)
C1—C6—H6120.2C34—C35—H35119.8
C8—C7—C12119.2 (4)C36—C35—H35119.8
C8—C7—P1121.2 (3)C35—C36—C37120.0 (4)
C12—C7—P1119.5 (3)C35—C36—H36120.0
C9—C8—C7120.6 (4)C37—C36—H36120.0
C9—C8—H8119.7C36—C37—C32120.1 (4)
C7—C8—H8119.7C36—C37—H37120.0
C8—C9—C10119.4 (4)C32—C37—H37120.0
C8—C9—H9120.3C39—C38—C43120.1 (4)
C10—C9—H9120.3C39—C38—P2119.7 (3)
C11—C10—C9120.5 (4)C43—C38—P2120.3 (3)
C11—C10—H10119.8C40—C39—C38119.8 (4)
C9—C10—H10119.8C40—C39—H39120.1
C12—C11—C10120.4 (4)C38—C39—H39120.1
C12—C11—H11119.8C39—C40—C41120.5 (4)
C10—C11—H11119.8C39—C40—H40119.7
C11—C12—C7119.9 (4)C41—C40—H40119.7
C11—C12—H12120.0C42—C41—C40119.6 (4)
C7—C12—H12120.0C42—C41—H41120.2
C18—C13—C14119.0 (4)C40—C41—H41120.2
C18—C13—P1119.1 (3)C43—C42—C41120.5 (4)
C14—C13—P1121.8 (3)C43—C42—H42119.7
C15—C14—C13120.3 (4)C41—C42—H42119.7
C15—C14—H14119.9C42—C43—C38119.4 (4)
C13—C14—H14119.9C42—C43—H43120.3
C16—C15—C14120.2 (4)C38—C43—H43120.3
C16—C15—H15119.9C45—C44—P2114.8 (3)
C14—C15—H15119.9C45—C44—H44A108.6
C15—C16—C17119.6 (4)P2—C44—H44A108.6
C15—C16—H16120.2C45—C44—H44B108.6
C17—C16—H16120.2P2—C44—H44B108.6
C18—C17—C16120.4 (4)H44A—C44—H44B107.5
C18—C17—H17119.8C50—C45—C46118.4 (4)
C16—C17—H17119.8C50—C45—C44119.9 (4)
C17—C18—C13120.5 (4)C46—C45—C44121.7 (4)
C17—C18—H18119.7C47—C46—C45120.2 (4)
C13—C18—H18119.7C47—C46—H46119.9
C20—C19—P1113.1 (3)C45—C46—H46119.9
C20—C19—H19A109.0C48—C47—C46118.8 (4)
P1—C19—H19A109.0C48—C47—H47120.6
C20—C19—H19B109.0C46—C47—H47120.6
P1—C19—H19B109.0C47—C48—C49122.6 (4)
H19A—C19—H19B107.8C47—C48—Cl6119.2 (4)
C25—C20—C21118.6 (4)C49—C48—Cl6118.2 (4)
C25—C20—C19120.4 (4)C48—C49—C50117.9 (4)
C21—C20—C19121.0 (4)C48—C49—H49121.0
C22—C21—C20120.8 (4)C50—C49—H49121.0
C22—C21—H21119.6C49—C50—C45122.1 (4)
C20—C21—H21119.6C49—C50—H50119.0
C23—C22—C21119.0 (4)C45—C50—H50119.0
C7—P1—C1—C2−106.3 (4)C32—P2—C26—C31−37.0 (4)
C13—P1—C1—C217.6 (4)C38—P2—C26—C3180.6 (4)
C19—P1—C1—C2137.8 (3)C44—P2—C26—C31−160.0 (3)
C7—P1—C1—C667.9 (4)C32—P2—C26—C27145.1 (4)
C13—P1—C1—C6−168.2 (3)C38—P2—C26—C27−97.3 (4)
C19—P1—C1—C6−48.0 (4)C44—P2—C26—C2722.1 (4)
C6—C1—C2—C30.1 (6)C31—C26—C27—C28−0.4 (7)
P1—C1—C2—C3174.2 (3)P2—C26—C27—C28177.5 (3)
C1—C2—C3—C40.5 (6)C26—C27—C28—C290.4 (7)
C2—C3—C4—C5−0.6 (7)C27—C28—C29—C30−0.3 (7)
C3—C4—C5—C60.0 (7)C28—C29—C30—C310.2 (7)
C4—C5—C6—C10.6 (6)C27—C26—C31—C300.3 (7)
C2—C1—C6—C5−0.7 (6)P2—C26—C31—C30−177.7 (4)
P1—C1—C6—C5−174.9 (3)C29—C30—C31—C26−0.1 (7)
C13—P1—C7—C8−122.5 (3)C38—P2—C32—C37152.1 (4)
C1—P1—C7—C8−0.5 (4)C26—P2—C32—C37−89.8 (4)
C19—P1—C7—C8117.9 (4)C44—P2—C32—C3731.9 (4)
C13—P1—C7—C1260.8 (4)C38—P2—C32—C33−33.7 (4)
C1—P1—C7—C12−177.2 (3)C26—P2—C32—C3384.4 (4)
C19—P1—C7—C12−58.8 (4)C44—P2—C32—C33−153.9 (3)
C12—C7—C8—C90.6 (6)C37—C32—C33—C340.8 (7)
P1—C7—C8—C9−176.1 (3)P2—C32—C33—C34−173.5 (3)
C7—C8—C9—C10−0.4 (6)C32—C33—C34—C35−1.6 (7)
C8—C9—C10—C11−0.5 (7)C33—C34—C35—C360.7 (7)
C9—C10—C11—C121.2 (7)C34—C35—C36—C370.9 (7)
C10—C11—C12—C7−1.0 (6)C35—C36—C37—C32−1.7 (7)
C8—C7—C12—C110.1 (6)C33—C32—C37—C360.8 (7)
P1—C7—C12—C11176.9 (3)P2—C32—C37—C36175.2 (4)
C7—P1—C13—C18174.7 (3)C32—P2—C38—C39−53.1 (4)
C1—P1—C13—C1853.4 (4)C26—P2—C38—C39−171.6 (3)
C19—P1—C13—C18−67.4 (4)C44—P2—C38—C3968.8 (4)
C7—P1—C13—C14−8.8 (4)C32—P2—C38—C43127.4 (4)
C1—P1—C13—C14−130.1 (3)C26—P2—C38—C438.9 (4)
C19—P1—C13—C14109.1 (4)C44—P2—C38—C43−110.7 (4)
C18—C13—C14—C15−0.8 (6)C43—C38—C39—C400.3 (6)
P1—C13—C14—C15−177.3 (3)P2—C38—C39—C40−179.2 (3)
C13—C14—C15—C160.7 (7)C38—C39—C40—C41−0.4 (7)
C14—C15—C16—C170.1 (7)C39—C40—C41—C420.2 (7)
C15—C16—C17—C18−0.9 (7)C40—C41—C42—C430.2 (7)
C16—C17—C18—C130.9 (6)C41—C42—C43—C38−0.4 (7)
C14—C13—C18—C17−0.1 (6)C39—C38—C43—C420.1 (6)
P1—C13—C18—C17176.5 (3)P2—C38—C43—C42179.6 (3)
C7—P1—C19—C20179.6 (3)C32—P2—C44—C4573.3 (4)
C13—P1—C19—C2057.6 (4)C38—P2—C44—C45−46.2 (4)
C1—P1—C19—C20−63.1 (4)C26—P2—C44—C45−165.2 (3)
P1—C19—C20—C25−97.7 (4)P2—C44—C45—C5097.8 (4)
P1—C19—C20—C2183.5 (5)P2—C44—C45—C46−82.3 (4)
C25—C20—C21—C221.3 (6)C50—C45—C46—C47−0.2 (6)
C19—C20—C21—C22−179.8 (4)C44—C45—C46—C47180.0 (4)
C20—C21—C22—C23−1.3 (7)C45—C46—C47—C480.0 (6)
C21—C22—C23—C240.3 (7)C46—C47—C48—C490.7 (7)
C21—C22—C23—Cl5−178.7 (3)C46—C47—C48—Cl6179.7 (3)
C22—C23—C24—C250.7 (7)C47—C48—C49—C50−1.1 (7)
Cl5—C23—C24—C25179.7 (3)Cl6—C48—C49—C50179.8 (3)
C23—C24—C25—C20−0.7 (6)C48—C49—C50—C450.9 (7)
C21—C20—C25—C24−0.3 (6)C46—C45—C50—C49−0.3 (6)
C19—C20—C25—C24−179.2 (4)C44—C45—C50—C49179.6 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1w—H1w1···Cl10.842.593.361 (4)154
O1w—H1w2···Cl20.842.413.184 (4)153
O2w—H2w1···Cl10.842.583.385 (9)161
O3w—H3w1···O4w0.842.313.12 (2)160
O3w—H3w2···Cl30.842.433.27 (2)172
O4w—H4w1···Cl10.842.293.09 (1)158

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5270).

References

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  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruni, S., Cariati, F., Cesarotti, E., Chiodini, G. & Moggi, G. (1992). Inorg. Chim. Acta, 192, 233–236.
  • Pattacini, R., Jie, S. & Braunstein, P. (2009). Chem. Commun. pp. 890–892. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
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  • Westrip, S. P. (2010). J. Appl. Cryst.43 Submitted.

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