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ISSN: 2056-9890

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

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: mjamil@um.edu.my

(Received 14 May 2010; accepted 17 May 2010; online 22 May 2010)

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[Bruni, S., Cariati, F., Cesarotti, E., Chiodini, G. & Moggi, G. (1992). Inorg. Chim. Acta, 192, 233-236.]). For the crystal structures of two related zincates, see: Aliev et al. (1988[Aliev, Z. G., Karateev, A. M. & Atovmyan, L. O. (1988). Koord. Khim. 14, 530-535.]); Pattacini et al. (2009[Pattacini, R., Jie, S. & Braunstein, P. (2009). Chem. Commun. pp. 890-892.]).

[Scheme 1]

Experimental

Crystal data
  • (C25H21ClP)2[ZnCl4]·3H2O

  • Mr = 1036.89

  • Triclinic, [P \overline 1]

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.869, Tmax = 0.972

  • 23163 measured reflections

  • 10895 independent reflections

  • 6579 reflections with I > 2σ(I)

  • Rint = 0.064

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 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

Table 1
Selected bond lengths (Å)

Zn1—Cl1 2.3049 (14)
Zn1—Cl2 2.2685 (14)
Zn1—Cl3 2.2800 (13)
Zn1—Cl4 2.2571 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1w—H1w1⋯Cl1 0.84 2.59 3.361 (4) 154
O1w—H1w2⋯Cl2 0.84 2.41 3.184 (4) 153
O2w—H2w1⋯Cl1 0.84 2.58 3.385 (9) 161
O3w—H3w1⋯O4w 0.84 2.31 3.12 (2) 160
O3w—H3w2⋯Cl3 0.84 2.43 3.27 (2) 172
O4w—H4w1⋯Cl1 0.84 2.29 3.09 (1) 158

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. 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: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.]).

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Structure description top

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.

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

Computing details top

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

Figures top
[Figure 1] 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.
Bis[(4-chlorobenzyl)triphenylphosphonium] tetrachloridozincate(II) trihydrate top
Crystal data top
(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 top
Bruker SMART APEX
diffractometer
10895 independent reflections
Radiation source: fine-focus sealed tube6579 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.869, Tmax = 0.972k = 1718
23163 measured reflectionsl = 2119
Refinement top
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 = 1.00 w = 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
Crystal data top
(C25H21ClP)2[ZnCl4]·3H2Oγ = 68.205 (2)°
Mr = 1036.89V = 2379.7 (4) Å3
Triclinic, P1Z = 2
a = 11.2634 (12) ÅMo Kα radiation
b = 14.2995 (15) ŵ = 0.96 mm1
c = 16.9288 (17) ÅT = 100 K
α = 73.651 (1)°0.15 × 0.10 × 0.03 mm
β = 73.527 (2)°
Data collection top
Bruker SMART APEX
diffractometer
10895 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
6579 reflections with I > 2σ(I)
Tmin = 0.869, Tmax = 0.972Rint = 0.064
23163 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05918 restraints
wR(F2) = 0.164H-atom parameters constrained
S = 1.00Δρmax = 1.16 e Å3
10895 reflectionsΔρmin = 0.82 e Å3
568 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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
H4w20.04621.09550.41620.322*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)
H110.53641.26370.04760.026*
C120.6518 (4)1.1160 (3)0.0243 (3)0.0188 (9)
H120.63941.09680.07000.023*
C130.9112 (4)0.9036 (3)0.0868 (3)0.0162 (9)
C140.9176 (4)0.9902 (4)0.1498 (3)0.0226 (10)
H140.86811.05690.13870.027*
C150.9958 (4)0.9791 (4)0.2285 (3)0.0252 (10)
H151.00061.03830.27090.030*
C161.0669 (4)0.8823 (4)0.2454 (3)0.0270 (11)
H161.12060.87470.29930.032*
C171.0593 (4)0.7961 (4)0.1833 (3)0.0235 (10)
H171.10710.72950.19500.028*
C180.9830 (4)0.8068 (3)0.1046 (3)0.0202 (9)
H180.97950.74740.06230.024*
C190.6724 (4)0.8668 (3)0.0237 (3)0.0212 (10)
H19A0.61550.87140.08000.025*
H19B0.61950.91160.01870.025*
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)
H240.77140.62450.13010.025*
C250.7269 (4)0.7367 (3)0.0653 (3)0.0211 (10)
H250.70540.79220.11090.025*
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)
H290.05710.34020.57380.037*
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)
H350.70570.09240.39520.032*
C360.6728 (5)0.0184 (4)0.4591 (3)0.0283 (11)
H360.72220.02490.50030.034*
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) top
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, º) top
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—C2106.3 (4)C32—P2—C26—C3137.0 (4)
C13—P1—C1—C217.6 (4)C38—P2—C26—C3180.6 (4)
C19—P1—C1—C2137.8 (3)C44—P2—C26—C31160.0 (3)
C7—P1—C1—C667.9 (4)C32—P2—C26—C27145.1 (4)
C13—P1—C1—C6168.2 (3)C38—P2—C26—C2797.3 (4)
C19—P1—C1—C648.0 (4)C44—P2—C26—C2722.1 (4)
C6—C1—C2—C30.1 (6)C31—C26—C27—C280.4 (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—C50.6 (7)C27—C28—C29—C300.3 (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—C50.7 (6)P2—C26—C31—C30177.7 (4)
P1—C1—C6—C5174.9 (3)C29—C30—C31—C260.1 (7)
C13—P1—C7—C8122.5 (3)C38—P2—C32—C37152.1 (4)
C1—P1—C7—C80.5 (4)C26—P2—C32—C3789.8 (4)
C19—P1—C7—C8117.9 (4)C44—P2—C32—C3731.9 (4)
C13—P1—C7—C1260.8 (4)C38—P2—C32—C3333.7 (4)
C1—P1—C7—C12177.2 (3)C26—P2—C32—C3384.4 (4)
C19—P1—C7—C1258.8 (4)C44—P2—C32—C33153.9 (3)
C12—C7—C8—C90.6 (6)C37—C32—C33—C340.8 (7)
P1—C7—C8—C9176.1 (3)P2—C32—C33—C34173.5 (3)
C7—C8—C9—C100.4 (6)C32—C33—C34—C351.6 (7)
C8—C9—C10—C110.5 (7)C33—C34—C35—C360.7 (7)
C9—C10—C11—C121.2 (7)C34—C35—C36—C370.9 (7)
C10—C11—C12—C71.0 (6)C35—C36—C37—C321.7 (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—C3953.1 (4)
C1—P1—C13—C1853.4 (4)C26—P2—C38—C39171.6 (3)
C19—P1—C13—C1867.4 (4)C44—P2—C38—C3968.8 (4)
C7—P1—C13—C148.8 (4)C32—P2—C38—C43127.4 (4)
C1—P1—C13—C14130.1 (3)C26—P2—C38—C438.9 (4)
C19—P1—C13—C14109.1 (4)C44—P2—C38—C43110.7 (4)
C18—C13—C14—C150.8 (6)C43—C38—C39—C400.3 (6)
P1—C13—C14—C15177.3 (3)P2—C38—C39—C40179.2 (3)
C13—C14—C15—C160.7 (7)C38—C39—C40—C410.4 (7)
C14—C15—C16—C170.1 (7)C39—C40—C41—C420.2 (7)
C15—C16—C17—C180.9 (7)C40—C41—C42—C430.2 (7)
C16—C17—C18—C130.9 (6)C41—C42—C43—C380.4 (7)
C14—C13—C18—C170.1 (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—C4546.2 (4)
C1—P1—C19—C2063.1 (4)C26—P2—C44—C45165.2 (3)
P1—C19—C20—C2597.7 (4)P2—C44—C45—C5097.8 (4)
P1—C19—C20—C2183.5 (5)P2—C44—C45—C4682.3 (4)
C25—C20—C21—C221.3 (6)C50—C45—C46—C470.2 (6)
C19—C20—C21—C22179.8 (4)C44—C45—C46—C47180.0 (4)
C20—C21—C22—C231.3 (7)C45—C46—C47—C480.0 (6)
C21—C22—C23—C240.3 (7)C46—C47—C48—C490.7 (7)
C21—C22—C23—Cl5178.7 (3)C46—C47—C48—Cl6179.7 (3)
C22—C23—C24—C250.7 (7)C47—C48—C49—C501.1 (7)
Cl5—C23—C24—C25179.7 (3)Cl6—C48—C49—C50179.8 (3)
C23—C24—C25—C200.7 (6)C48—C49—C50—C450.9 (7)
C21—C20—C25—C240.3 (6)C46—C45—C50—C490.3 (6)
C19—C20—C25—C24179.2 (4)C44—C45—C50—C49179.6 (4)
Hydrogen-bond geometry (Å, º) top
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

Experimental details

Crystal data
Chemical formula(C25H21ClP)2[ZnCl4]·3H2O
Mr1036.89
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)11.2634 (12), 14.2995 (15), 16.9288 (17)
α, β, γ (°)73.651 (1), 73.527 (2), 68.205 (2)
V3)2379.7 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.96
Crystal size (mm)0.15 × 0.10 × 0.03
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.869, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
23163, 10895, 6579
Rint0.064
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.164, 1.00
No. of reflections10895
No. of parameters568
No. of restraints18
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.16, 0.82

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top
Zn1—Cl12.3049 (14)Zn1—Cl32.2800 (13)
Zn1—Cl22.2685 (14)Zn1—Cl42.2571 (12)
Hydrogen-bond geometry (Å, º) top
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
 

Acknowledgements

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

References

First citationAliev, Z. G., Karateev, A. M. & Atovmyan, L. O. (1988). Koord. Khim. 14, 530–535.  CAS Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruni, S., Cariati, F., Cesarotti, E., Chiodini, G. & Moggi, G. (1992). Inorg. Chim. Acta, 192, 233–236.  CrossRef CAS Web of Science Google Scholar
First citationPattacini, R., Jie, S. & Braunstein, P. (2009). Chem. Commun. pp. 890–892.  Web of Science CSD CrossRef Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.  Google Scholar

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