Bis(4-chloro­benzyl­ammonium) tetra­kis(2,6-diethyl­anilinium) cyclo­hexa­phosphate tetra­hydrate

Amri, O.; Abid, S.; Rzaigui, M.

doi:10.1107/S1600536809006655

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o654

doi:10.1107/S1600536809006655

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Bis(4-chlorobenzylammonium) tetrakis(2,6-diethylanilinium) cyclohexaphosphate tetrahydrate

Olfa Amri,^a Sonia Abid ^a ^* and Mohamed Rzaigui ^a

^aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia
^*Correspondence e-mail: sonia.abid@fsb.rnu.tn

(Received 21 February 2009; accepted 23 February 2009; online 28 February 2009)

In the crystal of the title hydrated molecular salt, 2C₇H₉ClN⁺·4C₁₀H₁₆N⁺·P₆O₁₈⁶⁻·4H₂O, the packing consists of a three-dimensional O—H⋯O and N—H⋯O hydrogen-bonded network resulting from the association of anionic layers built up from centrosymmetric cyclohexaphosphate ions and water molecules and the two types of organic cations.

Related literature

For related structures, see: Amri et al. (2007 , 2008 ); Marouani & Rzaigui (2002 ). For background, see: Kresge et al. (1992 ); Katsoulis (1998 ).

Experimental

Crystal data

2C₇H₉ClN⁺·4C₁₀H₁₆N⁺·P₆O₁₈⁶⁻·4H₂O
M_r = 1432.04
Monoclinic, C 2/c
a = 31.437 (2) Å
b = 14.178 (2) Å
c = 16.034 (2) Å
β = 99.60 (2)°
V = 7046.5 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.16 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer
Absorption correction: none
11637 measured reflections
8452 independent reflections
5321 reflections with I > 2σ(I)
R_int = 0.035
2 standard reflections frequency: 120 min intensity decay: 5%

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.144
S = 1.02
8452 reflections
417 parameters
H-atom parameters not refined
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O9ⁱ	0.89	1.80	2.685 (3)	171
N1—H1B⋯O2	0.89	2.03	2.758 (3)	138
N1—H1C⋯O4	0.89	2.13	2.935 (3)	151
N2—H2A⋯O4ⁱⁱ	0.89	1.94	2.827 (3)	172
N2—H2B⋯O1	0.89	2.05	2.887 (3)	156
N2—H2C⋯O7	0.89	1.94	2.809 (3)	166
N3—H3A⋯O5ⁱⁱⁱ	0.89	1.89	2.762 (3)	165
N3—H3B⋯O9	0.89	1.93	2.799 (3)	164
N3—H3C⋯O10	0.89	1.99	2.800 (5)	151
O10—H1⋯O11	0.85	2.22	2.923 (6)	140
O10—H2⋯O11^iv	0.86	2.25	2.831 (5)	125
O11—H6⋯O2^v	0.85	2.23	2.740 (4)	118
O11—H7⋯O5ⁱⁱⁱ	0.85	2.17	2.781 (4)	129
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (v) x, y+1, z.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006655/hb2918sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006655/hb2918Isup2.hkl

checkCIF report

Comment top

The synthesis and characterization of organic–inorganic solid state hybrid materials has attracted great attention due to their structural diversity (Kresge et al., 1992) and widely promising potential areas in chemistry, biology and material science (Katsoulis, 1998). As part of our studies in this area, we report here synthesis and crystal structure of the the title compound, (I), (Fig. 1).

The centrosymmetric cyclohexaphosphate anion and the two water molecules are linked together by O—H···O hydrogen bonds to form inorganic layers parallel to the (b,c) plane. On both sides of each inorganic layer, are grafted the organic cations compensating their negatives charges (Fig. 2). Inside this arrangement, the geometry of the phosphoric rings is comparable to those found in [2,6-(CH₃)₂C₆H₃NH₃]₄[2,6-(C₂H₅)₂C₆H₃NH₃]~2_P6_O18_.4H2_{O (Amri et al. 2007) and (1,6NH}3_C6_H12_NH3_)(C6_H5_NH3₎4_P6_O18_.6H2_{O (Marouani et al. 2002). In the title compound, the phosphoric rings have the same internal symmetry and thus built up by only three independent PO}4_{tetrahedra P1O}4_{, P2O}4_{and P3O}4_{. In the PO}4 _{tetrahedra, the P—O distances range in [1.470 (3) - 1.610 (2) Å] and the O—P—O bond angles in [99.4 (2) - 121.2 (2)°]. It is the same for the P—P distances ranging from 2.901 (1) and 2.937 (1) Å which are comparable to values generally measured. For the organic cations, the main features measured are similar to distances and angles usually reported for such molecules (Amri et al.2007, Amri et al. 2008). The phenyl rings of these groups are almost planar, with mean deviations of ± 0.004 and ± 0.011Å for 2,6- diethylphenylammonium and ± 0.003 Å for 4-chlorobenzylanilinium.}

Related literature top

For related structures, see: Amri et al. (2007, 2008); Marouani & Rzaigui (2002). For background, see: Kresge et al. (1992); Katsoulis (1998).

Experimental top

Cyclohexaphosphoric acid (4.8 mmol) was slowly added to an ethanolic solution of 2,6-diethylaniline (3.16 ml; 19.2 mmol) and 4-chlorobenzylaniline (1.16 ml, 9.6 mmol) in a molar ratio of 2:1 respectively. The obtained solution was slowly evaporated at room temperature. After some days, colourless prisms of (I) were formed. The cyclohexaphosphoric acid is freshly prepared by passing a solution of Li₆P₆O₁₈(3 g, 4.8 mmol) through an ion exchange resin in its H-state (Amberlite IR 120).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of (I) with displacement ellipsoids for the non-H atoms drawn at the 30% probability level (symmetry code: (i) 1/2 - x, 1/2 - y, 1 -z).
	Fig. 2. Projection of (I) along b axis.

Bis(4-chlorobenzylammonium) tetrakis(2,6-diethylanilinium) cyclohexaphosphate tetrahydrate top

Crystal data top

2C₇H₉ClN⁺·4C₁₀H₁₆N⁺·P₆O₁₈⁶⁻·4H₂O	F(000) = 3024
M_r = 1432.04	D_x = 1.350 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 31.437 (2) Å	θ = 9–11°
b = 14.178 (2) Å	µ = 0.30 mm⁻¹
c = 16.034 (2) Å	T = 293 K
β = 99.60 (2)°	Prism, colourless
V = 7046.5 (14) Å³	0.20 × 0.18 × 0.16 mm
Z = 4

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	R_int = 0.035
Radiation source: Enraf Nonius FR590	θ_max = 28.0°, θ_min = 2.1°
Graphite monochromator	h = −41→41
non–profiled ω scans	k = 0→18
11637 measured reflections	l = −5→21
8452 independent reflections	2 standard reflections every 120 min
5321 reflections with I > 2σ(I)	intensity decay: 5%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters not refined
S = 1.02	w = 1/[σ²(F_o²) + (0.0697P)² + 2.2936P] where P = (F_o² + 2F_c²)/3
8452 reflections	(Δ/σ)_max < 0.001
417 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

2C₇H₉ClN⁺·4C₁₀H₁₆N⁺·P₆O₁₈⁶⁻·4H₂O	V = 7046.5 (14) Å³
M_r = 1432.04	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 31.437 (2) Å	µ = 0.30 mm⁻¹
b = 14.178 (2) Å	T = 293 K
c = 16.034 (2) Å	0.20 × 0.18 × 0.16 mm
β = 99.60 (2)°

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	R_int = 0.035
11637 measured reflections	2 standard reflections every 120 min
8452 independent reflections	intensity decay: 5%
5321 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.144	H-atom parameters not refined
S = 1.02	Δρ_max = 0.57 e Å⁻³
8452 reflections	Δρ_min = −0.44 e Å⁻³
417 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

	x	y	z	U_iso*/U_eq
Cl1	0.01382 (3)	0.69163 (8)	0.12825 (8)	0.0880 (3)
P1	0.24807 (2)	0.07584 (5)	0.44736 (4)	0.03164 (16)
P2	0.23420 (2)	0.23566 (5)	0.33302 (4)	0.03092 (15)
P3	0.293786 (19)	0.38486 (4)	0.40635 (4)	0.03042 (15)
O1	0.28646 (5)	0.04571 (12)	0.50699 (11)	0.0400 (4)
O2	0.22756 (7)	0.01330 (14)	0.37887 (13)	0.0541 (5)
O3	0.26078 (5)	0.17399 (13)	0.40739 (12)	0.0414 (4)
O4	0.18744 (5)	0.22936 (14)	0.33497 (12)	0.0428 (4)
O5	0.24898 (7)	0.21336 (15)	0.25302 (12)	0.0524 (5)
O6	0.24927 (6)	0.33887 (13)	0.36243 (14)	0.0485 (5)
O7	0.33084 (5)	0.32302 (13)	0.39994 (12)	0.0423 (4)
O8	0.28898 (6)	0.38724 (15)	0.50341 (11)	0.0462 (5)
O9	0.29240 (6)	0.48264 (13)	0.37325 (13)	0.0454 (5)
O10	0.19365 (13)	0.6949 (3)	0.4542 (2)	0.1059 (10)
H1	0.2147	0.7334	0.4620	0.21 (4)*
H2	0.1988	0.6545	0.4948	0.15 (3)*
O11	0.25125 (15)	0.8271 (2)	0.38834 (19)	0.1238 (15)
H6	0.2411	0.8642	0.3478	0.37 (7)*
H7	0.2659	0.7851	0.3679	0.58 (12)*
N1	0.16392 (7)	0.05296 (16)	0.24302 (14)	0.0422 (5)
H1A	0.1792	0.0362	0.2034	0.063*
H1B	0.1734	0.0214	0.2905	0.063*
H1C	0.1669	0.1146	0.2527	0.063*
N2	0.35074 (6)	0.19299 (15)	0.53288 (14)	0.0363 (5)
H2A	0.3395	0.2228	0.5729	0.054*
H2B	0.3377	0.1376	0.5221	0.054*
H2C	0.3470	0.2278	0.4860	0.054*
N3	0.21272 (7)	0.57295 (18)	0.32809 (16)	0.0500 (6)
H3A	0.2205	0.6199	0.2970	0.075*
H3B	0.2360	0.5407	0.3512	0.075*
H3C	0.1998	0.5965	0.3688	0.075*
C1	0.11824 (8)	0.0310 (2)	0.21416 (17)	0.0415 (6)
C2	0.10027 (9)	−0.0469 (2)	0.24718 (19)	0.0507 (7)
C3	0.05691 (11)	−0.0647 (3)	0.2167 (2)	0.0688 (10)
H3	0.0436	−0.1163	0.2373	0.083*
C4	0.03350 (11)	−0.0076 (3)	0.1571 (3)	0.0799 (12)
H4	0.0045	−0.0206	0.1382	0.096*
C5	0.05230 (11)	0.0683 (3)	0.1251 (2)	0.0753 (11)
H5	0.0360	0.1059	0.0843	0.090*
C6	0.09543 (10)	0.0899 (2)	0.15295 (19)	0.0530 (8)
C7	0.11533 (14)	0.1759 (3)	0.1192 (3)	0.0777 (11)
H7A	0.1459	0.1645	0.1207	0.093*
H7B	0.1023	0.1853	0.0606	0.093*
C8	0.10995 (18)	0.2644 (3)	0.1678 (3)	0.1045 (16)
H8A	0.0799	0.2806	0.1609	0.157*
H8B	0.1256	0.3149	0.1470	0.157*
H8C	0.1209	0.2543	0.2267	0.157*
C9	0.12659 (12)	−0.1088 (3)	0.3131 (2)	0.0683 (10)
H9A	0.1434	−0.0686	0.3551	0.082*
H9B	0.1467	−0.1448	0.2860	0.082*
C10	0.10082 (16)	−0.1772 (3)	0.3583 (3)	0.0936 (13)
H10A	0.0811	−0.1425	0.3864	0.140*
H10B	0.1202	−0.2128	0.3991	0.140*
H10C	0.0849	−0.2194	0.3177	0.140*
C11	0.39714 (8)	0.17773 (19)	0.56208 (17)	0.0378 (6)
C12	0.42153 (9)	0.2542 (2)	0.59790 (19)	0.0459 (7)
C13	0.46474 (11)	0.2379 (3)	0.6290 (2)	0.0671 (10)
H13	0.4818	0.2869	0.6545	0.081*
C14	0.48285 (10)	0.1505 (3)	0.6226 (3)	0.0786 (12)
H14	0.5119	0.1412	0.6438	0.094*
C15	0.45849 (10)	0.0770 (3)	0.5855 (2)	0.0669 (10)
H15	0.4713	0.0186	0.5808	0.080*
C16	0.41455 (9)	0.0887 (2)	0.5545 (2)	0.0461 (7)
C17	0.40416 (10)	0.3535 (2)	0.6000 (2)	0.0547 (8)
H17A	0.3729	0.3512	0.5935	0.066*
H17B	0.4150	0.3817	0.6545	0.066*
C18	0.41691 (12)	0.4142 (2)	0.5311 (2)	0.0675 (10)
H18A	0.4478	0.4147	0.5360	0.101*
H18B	0.4067	0.4773	0.5364	0.101*
H18C	0.4044	0.3891	0.4769	0.101*
C19	0.38797 (10)	0.0071 (2)	0.5151 (3)	0.0635 (9)
H19A	0.3622	0.0033	0.5407	0.076*
H19B	0.3788	0.0210	0.4555	0.076*
C20	0.40905 (15)	−0.0872 (3)	0.5220 (3)	0.0992 (15)
H20A	0.4322	−0.0877	0.4897	0.149*
H20B	0.3882	−0.1346	0.5006	0.149*
H20C	0.4203	−0.1002	0.5803	0.149*
C21	0.14034 (9)	0.5570 (2)	0.23882 (18)	0.0453 (7)
C22	0.13925 (9)	0.6432 (2)	0.19784 (18)	0.0470 (7)
H22	0.1651	0.6734	0.1935	0.056*
C23	0.10094 (9)	0.6850 (2)	0.16347 (19)	0.0488 (7)
H23	0.1007	0.7427	0.1358	0.059*
C24	0.06256 (9)	0.6395 (2)	0.1708 (2)	0.0535 (8)
C25	0.06304 (11)	0.5540 (3)	0.2110 (2)	0.0649 (9)
H25	0.0372	0.5238	0.2154	0.078*
C26	0.10184 (11)	0.5128 (2)	0.2447 (2)	0.0579 (8)
H26	0.1021	0.4548	0.2718	0.070*
C27	0.18274 (10)	0.5098 (2)	0.2740 (2)	0.0574 (8)
H27A	0.1771	0.4550	0.3067	0.069*
H27B	0.1963	0.4881	0.2274	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0443 (4)	0.0973 (8)	0.1139 (9)	0.0033 (5)	−0.0115 (5)	−0.0025 (7)
P1	0.0321 (3)	0.0326 (3)	0.0294 (3)	−0.0001 (3)	0.0026 (3)	0.0001 (3)
P2	0.0332 (3)	0.0313 (3)	0.0282 (3)	−0.0024 (3)	0.0053 (2)	0.0001 (3)
P3	0.0303 (3)	0.0308 (3)	0.0303 (3)	−0.0005 (2)	0.0055 (2)	0.0023 (3)
O1	0.0369 (9)	0.0413 (10)	0.0400 (10)	0.0045 (8)	0.0013 (8)	0.0042 (8)
O2	0.0625 (13)	0.0426 (11)	0.0508 (12)	0.0012 (10)	−0.0090 (10)	−0.0127 (10)
O3	0.0355 (9)	0.0458 (10)	0.0419 (10)	−0.0050 (8)	0.0034 (8)	0.0130 (9)
O4	0.0337 (9)	0.0540 (11)	0.0390 (10)	−0.0053 (8)	0.0009 (8)	0.0041 (9)
O5	0.0746 (13)	0.0520 (12)	0.0342 (10)	0.0114 (10)	0.0196 (10)	−0.0005 (9)
O6	0.0363 (9)	0.0353 (10)	0.0686 (14)	0.0020 (8)	−0.0063 (9)	−0.0110 (10)
O7	0.0352 (9)	0.0416 (10)	0.0509 (11)	0.0047 (8)	0.0091 (8)	−0.0015 (9)
O8	0.0359 (9)	0.0754 (14)	0.0281 (9)	0.0093 (9)	0.0074 (8)	0.0112 (9)
O9	0.0457 (10)	0.0401 (10)	0.0529 (12)	0.0012 (8)	0.0149 (9)	0.0137 (9)
O10	0.110 (3)	0.124 (3)	0.077 (2)	0.029 (2)	−0.0021 (17)	−0.005 (2)
O11	0.245 (5)	0.0640 (17)	0.0534 (16)	0.041 (2)	−0.001 (2)	−0.0106 (15)
N1	0.0381 (11)	0.0459 (13)	0.0421 (13)	0.0004 (10)	0.0054 (10)	−0.0121 (11)
N2	0.0335 (10)	0.0355 (11)	0.0391 (12)	0.0028 (9)	0.0036 (9)	−0.0012 (10)
N3	0.0403 (12)	0.0528 (15)	0.0560 (15)	0.0045 (11)	0.0052 (11)	0.0182 (13)
C1	0.0349 (13)	0.0500 (16)	0.0398 (15)	0.0021 (12)	0.0070 (11)	−0.0160 (13)
C2	0.0473 (16)	0.0577 (18)	0.0482 (17)	−0.0016 (14)	0.0107 (14)	−0.0150 (15)
C3	0.0480 (18)	0.079 (2)	0.082 (3)	−0.0122 (18)	0.0180 (18)	−0.010 (2)
C4	0.0417 (18)	0.110 (3)	0.084 (3)	−0.006 (2)	−0.0015 (19)	−0.011 (3)
C5	0.0507 (19)	0.104 (3)	0.066 (2)	0.018 (2)	−0.0057 (17)	−0.006 (2)
C6	0.0488 (16)	0.064 (2)	0.0454 (17)	0.0071 (15)	0.0059 (14)	−0.0089 (16)
C7	0.088 (3)	0.077 (3)	0.063 (2)	0.001 (2)	−0.002 (2)	0.014 (2)
C8	0.128 (4)	0.077 (3)	0.096 (3)	0.013 (3)	−0.019 (3)	0.003 (3)
C9	0.068 (2)	0.062 (2)	0.074 (2)	−0.0057 (18)	0.0119 (19)	0.0038 (19)
C10	0.121 (4)	0.079 (3)	0.084 (3)	−0.007 (3)	0.025 (3)	0.007 (2)
C11	0.0330 (12)	0.0441 (15)	0.0357 (14)	0.0007 (11)	0.0037 (11)	0.0040 (12)
C12	0.0408 (14)	0.0540 (18)	0.0434 (16)	−0.0078 (13)	0.0081 (12)	−0.0010 (14)
C13	0.0469 (18)	0.073 (2)	0.076 (2)	−0.0179 (17)	−0.0053 (16)	0.001 (2)
C14	0.0331 (16)	0.083 (3)	0.112 (3)	−0.0008 (17)	−0.0095 (18)	0.017 (2)
C15	0.0386 (16)	0.061 (2)	0.099 (3)	0.0131 (15)	0.0040 (17)	0.012 (2)
C16	0.0367 (13)	0.0446 (16)	0.0562 (18)	0.0054 (12)	0.0053 (13)	0.0064 (14)
C17	0.0558 (18)	0.0472 (17)	0.063 (2)	−0.0112 (14)	0.0162 (16)	−0.0176 (16)
C18	0.069 (2)	0.055 (2)	0.078 (2)	−0.0131 (17)	0.0102 (19)	−0.0027 (19)
C19	0.0516 (18)	0.0449 (18)	0.091 (3)	0.0065 (14)	0.0014 (18)	−0.0006 (18)
C20	0.096 (3)	0.062 (2)	0.134 (4)	0.014 (2)	0.000 (3)	−0.017 (3)
C21	0.0502 (16)	0.0464 (16)	0.0386 (15)	−0.0045 (13)	0.0054 (13)	0.0021 (13)
C22	0.0412 (14)	0.0513 (17)	0.0488 (17)	−0.0047 (13)	0.0086 (13)	0.0067 (14)
C23	0.0460 (15)	0.0502 (17)	0.0491 (17)	−0.0025 (13)	0.0048 (13)	0.0070 (14)
C24	0.0416 (15)	0.062 (2)	0.0537 (19)	−0.0031 (14)	−0.0010 (14)	−0.0070 (16)
C25	0.0508 (18)	0.068 (2)	0.075 (2)	−0.0224 (17)	0.0086 (17)	−0.0006 (19)
C26	0.064 (2)	0.0505 (18)	0.059 (2)	−0.0121 (16)	0.0089 (16)	0.0057 (16)
C27	0.0620 (19)	0.0477 (18)	0.061 (2)	0.0079 (15)	0.0047 (16)	0.0074 (16)

Geometric parameters (Å, º) top

O7—P3	1.4751 (18)	C1—C6	1.393 (4)
O6—P2	1.5854 (19)	C2—C3	1.392 (4)
O6—P3	1.5970 (19)	C2—C9	1.510 (5)
O1—P1	1.4724 (18)	C6—C5	1.389 (5)
O3—P2	1.5975 (19)	C6—C7	1.512 (5)
O3—P1	1.6101 (19)	C5—C4	1.368 (6)
O4—P2	1.4783 (18)	C5—H5	0.9300
O8—P3	1.5889 (18)	C3—C4	1.369 (5)
O8—P1ⁱ	1.6003 (19)	C3—H3	0.9300
O9—P3	1.4825 (19)	C4—H4	0.9300
O5—P2	1.470 (2)	C9—C10	1.522 (5)
O2—P1	1.474 (2)	C9—H9A	0.9700
P1—O8ⁱ	1.6003 (19)	C9—H9B	0.9700
N2—C11	1.472 (3)	C7—C8	1.501 (6)
N2—H2A	0.8900	C7—H7A	0.9700
N2—H2B	0.8900	C7—H7B	0.9700
N2—H2C	0.8900	C10—H10A	0.9600
C11—C16	1.389 (4)	C10—H10B	0.9600
C11—C12	1.395 (4)	C10—H10C	0.9600
C12—C13	1.386 (4)	C8—H8A	0.9600
C12—C17	1.512 (4)	C8—H8B	0.9600
C16—C15	1.398 (4)	C8—H8C	0.9600
C16—C19	1.503 (4)	Cl1—C24	1.735 (3)
C17—C18	1.506 (5)	N3—C27	1.473 (4)
C17—H17A	0.9700	N3—H3A	0.8900
C17—H17B	0.9700	N3—H3B	0.8900
C19—C20	1.489 (5)	N3—H3C	0.8900
C19—H19A	0.9700	C23—C22	1.372 (4)
C19—H19B	0.9700	C23—C24	1.390 (4)
C15—C14	1.369 (5)	C23—H23	0.9300
C15—H15	0.9300	C22—C21	1.385 (4)
C14—C13	1.374 (5)	C22—H22	0.9300
C14—H14	0.9300	C21—C26	1.380 (4)
C13—H13	0.9300	C21—C27	1.514 (4)
C18—H18A	0.9600	C24—C25	1.372 (5)
C18—H18B	0.9600	C25—C26	1.379 (5)
C18—H18C	0.9600	C25—H25	0.9300
C20—H20A	0.9600	C27—H27A	0.9700
C20—H20B	0.9600	C27—H27B	0.9700
C20—H20C	0.9600	C26—H26	0.9300
N1—C1	1.467 (3)	O11—H6	0.8600
N1—H1A	0.8900	O11—H7	0.8500
N1—H1B	0.8900	O10—H1	0.8500
N1—H1C	0.8900	O10—H2	0.8600
C1—C2	1.385 (4)

P2—O6—P3	134.79 (12)	C2—C1—C6	123.5 (3)
P2—O3—P1	129.53 (11)	C2—C1—N1	119.3 (3)
P3—O8—P1ⁱ	133.32 (12)	C6—C1—N1	117.2 (3)
O5—P2—O4	117.76 (12)	C1—C2—C3	116.7 (3)
O5—P2—O6	109.61 (12)	C1—C2—C9	121.3 (3)
O4—P2—O6	107.36 (11)	C3—C2—C9	122.0 (3)
O5—P2—O3	109.36 (11)	C5—C6—C1	117.0 (3)
O4—P2—O3	110.45 (10)	C5—C6—C7	120.2 (3)
O6—P2—O3	100.95 (10)	C1—C6—C7	122.7 (3)
O7—P3—O9	120.48 (11)	C4—C5—C6	120.8 (4)
O7—P3—O8	106.62 (11)	C4—C5—H5	119.6
O9—P3—O8	109.20 (12)	C6—C5—H5	119.6
O7—P3—O6	111.75 (11)	C4—C3—C2	121.2 (4)
O9—P3—O6	104.64 (11)	C4—C3—H3	119.4
O8—P3—O6	102.77 (11)	C2—C3—H3	119.4
O1—P1—O2	121.24 (11)	C5—C4—C3	120.7 (3)
O1—P1—O8ⁱ	111.08 (10)	C5—C4—H4	119.6
O2—P1—O8ⁱ	107.48 (12)	C3—C4—H4	119.6
O1—P1—O3	106.16 (10)	C2—C9—C10	115.5 (3)
O2—P1—O3	109.28 (11)	C2—C9—H9A	108.4
O8ⁱ—P1—O3	99.39 (11)	C10—C9—H9A	108.4
C11—N2—H2A	109.5	C2—C9—H9B	108.4
C11—N2—H2B	109.5	C10—C9—H9B	108.4
H2A—N2—H2B	109.5	H9A—C9—H9B	107.5
C11—N2—H2C	109.5	C8—C7—C6	113.5 (4)
H2A—N2—H2C	109.5	C8—C7—H7A	108.9
H2B—N2—H2C	109.5	C6—C7—H7A	108.9
C16—C11—C12	123.0 (2)	C8—C7—H7B	108.9
C16—C11—N2	119.3 (2)	C6—C7—H7B	108.9
C12—C11—N2	117.7 (2)	H7A—C7—H7B	107.7
C13—C12—C11	117.2 (3)	C9—C10—H10A	109.5
C13—C12—C17	118.9 (3)	C9—C10—H10B	109.5
C11—C12—C17	123.8 (3)	H10A—C10—H10B	109.5
C11—C16—C15	117.2 (3)	C9—C10—H10C	109.5
C11—C16—C19	122.4 (2)	H10A—C10—H10C	109.5
C15—C16—C19	120.3 (3)	H10B—C10—H10C	109.5
C18—C17—C12	112.0 (3)	C7—C8—H8A	109.5
C18—C17—H17A	109.2	C7—C8—H8B	109.5
C12—C17—H17A	109.2	H8A—C8—H8B	109.5
C18—C17—H17B	109.2	C7—C8—H8C	109.5
C12—C17—H17B	109.2	H8A—C8—H8C	109.5
H17A—C17—H17B	107.9	H8B—C8—H8C	109.5
C20—C19—C16	116.8 (3)	C27—N3—H3A	109.5
C20—C19—H19A	108.1	C27—N3—H3B	109.5
C16—C19—H19A	108.1	H3A—N3—H3B	109.5
C20—C19—H19B	108.1	C27—N3—H3C	109.5
C16—C19—H19B	108.1	H3A—N3—H3C	109.5
H19A—C19—H19B	107.3	H3B—N3—H3C	109.5
C14—C15—C16	120.8 (3)	C22—C23—C24	118.8 (3)
C14—C15—H15	119.6	C22—C23—H23	120.6
C16—C15—H15	119.6	C24—C23—H23	120.6
C15—C14—C13	120.7 (3)	C23—C22—C21	121.4 (3)
C15—C14—H14	119.7	C23—C22—H22	119.3
C13—C14—H14	119.7	C21—C22—H22	119.3
C14—C13—C12	121.1 (3)	C26—C21—C22	118.7 (3)
C14—C13—H13	119.4	C26—C21—C27	120.1 (3)
C12—C13—H13	119.4	C22—C21—C27	121.2 (3)
C17—C18—H18A	109.5	C25—C24—C23	120.5 (3)
C17—C18—H18B	109.5	C25—C24—Cl1	120.1 (3)
H18A—C18—H18B	109.5	C23—C24—Cl1	119.4 (3)
C17—C18—H18C	109.5	C24—C25—C26	119.9 (3)
H18A—C18—H18C	109.5	C24—C25—H25	120.1
H18B—C18—H18C	109.5	C26—C25—H25	120.1
C19—C20—H20A	109.5	N3—C27—C21	112.8 (2)
C19—C20—H20B	109.5	N3—C27—H27A	109.0
H20A—C20—H20B	109.5	C21—C27—H27A	109.0
C19—C20—H20C	109.5	N3—C27—H27B	109.0
H20A—C20—H20C	109.5	C21—C27—H27B	109.0
H20B—C20—H20C	109.5	H27A—C27—H27B	107.8
C1—N1—H1A	109.5	C25—C26—C21	120.6 (3)
C1—N1—H1B	109.5	C25—C26—H26	119.7
H1A—N1—H1B	109.5	C21—C26—H26	119.7
C1—N1—H1C	109.5	H6—O11—H7	107.00
H1A—N1—H1C	109.5	H1—O10—H2	106.00
H1B—N1—H1C	109.5

Symmetry code: (i) −x+1/2, −y+1/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O9ⁱⁱ	0.89	1.80	2.685 (3)	171
N1—H1B···O2	0.89	2.03	2.758 (3)	138
N1—H1C···O4	0.89	2.13	2.935 (3)	151
N2—H2A···O4ⁱ	0.89	1.94	2.827 (3)	172
N2—H2B···O1	0.89	2.05	2.887 (3)	156
N2—H2C···O7	0.89	1.94	2.809 (3)	166
N3—H3A···O5ⁱⁱⁱ	0.89	1.89	2.762 (3)	165
N3—H3B···O9	0.89	1.93	2.799 (3)	164
N3—H3C···O10	0.89	1.99	2.800 (5)	151
O10—H1···O11	0.85	2.22	2.923 (6)	140
O10—H2···O11^iv	0.86	2.25	2.831 (5)	125
O11—H6···O2^v	0.85	2.23	2.740 (4)	118
O11—H7···O5ⁱⁱⁱ	0.85	2.17	2.781 (4)	129

Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x+1/2, −y+3/2, −z+1; (v) x, y+1, z.

Experimental details

Crystal data
Chemical formula	2C₇H₉ClN⁺·4C₁₀H₁₆N⁺·P₆O₁₈⁶⁻·4H₂O
M_r	1432.04
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	31.437 (2), 14.178 (2), 16.034 (2)
β (°)	99.60 (2)
V (Å³)	7046.5 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Enraf–Nonius TurboCAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11637, 8452, 5321
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.144, 1.02
No. of reflections	8452
No. of parameters	417
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.44

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O9ⁱ	0.89	1.80	2.685 (3)	171
N1—H1B···O2	0.89	2.03	2.758 (3)	138
N1—H1C···O4	0.89	2.13	2.935 (3)	151
N2—H2A···O4ⁱⁱ	0.89	1.94	2.827 (3)	172
N2—H2B···O1	0.89	2.05	2.887 (3)	156
N2—H2C···O7	0.89	1.94	2.809 (3)	166
N3—H3A···O5ⁱⁱⁱ	0.89	1.89	2.762 (3)	165
N3—H3B···O9	0.89	1.93	2.799 (3)	164
N3—H3C···O10	0.89	1.99	2.800 (5)	151
O10—H1···O11	0.85	2.22	2.923 (6)	140
O10—H2···O11^iv	0.86	2.25	2.831 (5)	125
O11—H6···O2^v	0.85	2.23	2.740 (4)	118
O11—H7···O5ⁱⁱⁱ	0.85	2.17	2.781 (4)	129

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, −y+1/2, −z+1; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x+1/2, −y+3/2, −z+1; (v) x, y+1, z.

References

Amri, O., Abid, S. & Rzaigui, M. (2007). Cryst. Res. Technol. 42, 930–936. Web of Science CSD CrossRef CAS Google Scholar
Amri, O., Abid, S. & Rzaigui, M. (2008). Phosphorus Sulfur Silicon Relat. Elem. 183, 1984–1993. Web of Science CSD CrossRef CAS Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Katsoulis, D. E. (1998). Chem. Rev. 98, 359–387. Web of Science CrossRef PubMed CAS Google Scholar
Kresge, C. T., Leonowicz, M. E., Roth, W. J., Vartuli, J. C. & Beck, J. S. (1992). Nature (London), 359, 710–712. CrossRef CAS Web of Science Google Scholar
Marouani, H. & Rzaigui, M. (2002). Z. Kristallogr. New Cryst. Struct. 217, 277–278. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 3| March 2009| Page o654

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

Bis(4-chloro­benzyl­ammonium) tetra­kis(2,6-di­ethyl­anilinium) cyclo­hexa­phosphate tetra­hydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

Bis(4-chlorobenzylammonium) tetrakis(2,6-diethylanilinium) cyclohexaphosphate tetrahydrate