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

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ISSN: 2056-9890

2,8,9-Tris(2-methyl­prop­yl)-2,5,8,9-tetra­aza-1λ5-phosphatri­cyclo­[3.3.3.01,5]undecan-5-ium chloride dihydrate

aDepartment of Chemistry, Chonnam National University, Gwangju 500-757, Republic of Korea, and bDepartment of Chemistry, Chungbuk National University, Cheongju, Chungbuk 361-763, Republic of Korea
*Correspondence e-mail: ykim@chungbuk.ac.kr

(Received 23 October 2012; accepted 5 November 2012; online 10 November 2012)

The asymmetric unit of the title hydrated salt, C18H40N4P+·Cl·2H2O, consists of two ionic mol­ecules and four water mol­ecules. The mol­ecular geometry around the penta­coordinate P atom is trigonal–bipyramidal, with a H atom and an apical N atom in axial positions and three N atoms with isobutyl substituents in equatorial positions. The Cl ions and water mol­ecules are connected via O—H⋯Cl hydrogen bonds, forming chains along [100]. The ethyl­ene bridging groups are disordered with refined site-occupancy ratios of 0.578 (9):0.422 (9).

Related literature

For background to the applications of related compounds, see: Raders & Verkade (2010[Raders, M. R. & Verkade, J. G. (2010). J. Org. Chem. 75, 5308-5311.]); Tang et al. (1993[Tang, J.-S., Dopke, J. & Verkade, J. G. (1993). J. Am. Chem. Soc. 115, 5015-5020.]); Verkade & Kisang (2003[Verkade, J. G. & Kisanga, P. (2003). Tetrahedron, 59, 7819-7858.]); Zhou et al. (2011[Zhou, Y., Armstrong, D. W., Zhang, Y. & Verkade, J. G. (2011). Tetrahedron Lett. 52, 1545-1548.]). For similar structure types, see: Kingston & Verkade (2005[Kingston, J. V. & Verkade, J. G. (2005). Inorg. Chem. Commun. 8, 643-646.]); Kisanga & Verkade (2001[Kisanga, P. B. & Verkade, J. G. (2001). Tetrahedron, 57, 467-475.]); Liu et al. (1999[Liu, X., Bai, Y. & Verkade, J. G. (1999). J. Organomet. Chem. 582, 16-24.], 2000[Liu, X., Ilankumaran, P., Guzei, I. A. & Verkade, J. G. (2000). J. Org. Chem. 65, 701-706.]); Mohan et al. (1996[Mohan, T., Arumugam, S., Wang, T., Jacobson, R. A. & Verkade, J. G. (1996). Heteroatom Chem. 7, 455-460.]); Thirupathi et al. (2003[Thirupathi, N., Liu, X. & Verkade, J. G. (2003). Inorg. Chem. 42, 389-397.]); Wroblewski et al. (1995[Wroblewski, A., Pinkas, J. & Verkade, J. G. (1995). Main Group Chem. 1, 69-79.]).

[Scheme 1]

Experimental

Crystal data
  • C18H40N4P+·Cl·2H2O

  • Mr = 414.99

  • Triclinic, [P \overline 1]

  • a = 10.0945 (19) Å

  • b = 15.759 (3) Å

  • c = 16.122 (3) Å

  • α = 106.720 (8)°

  • β = 92.259 (8)°

  • γ = 90.616 (8)°

  • V = 2453.6 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 296 K

  • 0.20 × 0.15 × 0.14 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.954, Tmax = 0.967

  • 35181 measured reflections

  • 9856 independent reflections

  • 5364 reflections with I > 2σ(I)

  • Rint = 0.063

Refinement
  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.212

  • S = 1.01

  • 9856 reflections

  • 568 parameters

  • 18 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H101⋯Cl2i 0.84 (6) 2.61 (6) 3.426 (6) 164 (5)
O1—H102⋯Cl2ii 0.93 (9) 2.32 (9) 3.208 (6) 159 (7)
O2—H103⋯Cl2iii 0.85 (7) 2.60 (7) 3.412 (7) 161 (5)
O2—H104⋯Cl2ii 0.81 (8) 2.38 (9) 3.188 (6) 177 (8)
O3—H105⋯Cl1iii 0.86 (5) 2.45 (5) 3.263 (6) 159 (4)
O3—H106⋯Cl1iv 0.85 (4) 2.45 (4) 3.286 (6) 165 (4)
O4—H108⋯Cl1iii 0.73 (5) 2.56 (5) 3.286 (6) 175 (4)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x, y-1, z; (iii) -x+1, -y+1, -z+1; (iv) x-1, y, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). 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: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Nonionic proazaphosphatranes with stronger basicity than DBU (Tang et al., 1993) have been used as stoichiometric bases and as catalysts in a wide range of organic reactions (Raders et al., 2010; Verkade et al., 2003; Zhou et al., 2011). Unlike proazaphosphatranes, their protonated phosphonium salts known as azaphosphatranes with the five-membered tricyclic frameworks exist as solid states. Even though a lot of azaphosphatranes have appeared in the literature, only few examples of their solid state structures have been reported (Kingston et al., 2005; Liu et al., 1999; Liu et al., 2000; Mohan et al., 1996; Thirupathi et al., 2003; Wroblewski et al., 1995). In addition, the similar structure of the title complex (I) with four chloroform molecules in the monoclinic unit was reported in the literature; however, no crystallographic data and parameters were provided (Kisanga et al., 2001). Herein, we report the X-ray structure of the title complex (I).

The title compound (I) could be isolated in more than 90% yield via the reaction of (i-BuNHCH2CH2)3N with ClP(NMe2)2, prepared in situ in acetonitrile by the slow addition of 1 equivalent of PCl3 to 2 equivalents of P(NMe2)3. In (I) (Fig. 1), the nearly ideal trigonal bipyramidal geometry around the phosphorus atom is confirmed by the sum of the Neq—P—Neq angle of 358.8 ° and the average Neq—P—Nax angle value of 86.3 °. The axial transannular P—N distance of 1.973 (2) Å and the average equatorial P—N bond distance of 1.664 (3) Å are in the range of typical values determined on azaphosphatranes derivatives (Kingston et al., 2005; Liu et al., 1999; Liu et al., 2000; Mohan et al., 1996; Thirupathi et al., 2003; Wroblewski et al., 1995).

Related literature top

For background to the applications of related compounds, see: Raders et al. (2010); Tang et al. (1993); Verkade et al. (2003); Zhou et al. (2011). For similar structure types, see: Kingston et al. (2005); Kisanga et al. (2001); Liu et al. (1999, 2000); Mohan et al. (1996); Thirupathi et al. (2003); Wroblewski et al. (1995).

Experimental top

The title compound (I) could be isolated in more than 90% yield via the reaction of (i-BuNHCH2CH2)3N with ClP(NMe2)2, prepared in situ in acetonitrile by the slow addition of 1 equivalent of PCl3 to 2 equivalents of P(NMe2)3. The crystal was obtained by slow evaporation of solvent in refrigerator.

Refinement top

H atoms attached to C atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C). The water H atoms were found in difference Fourier maps and refined freely.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are omitted for clarity.
2,8,9-Tris(2-methylpropyl)-2,5,8,9-tetraaza-1λ5- phosphatricyclo[3.3.3.01,5]undecan-5-ium chloride dihydrate top
Crystal data top
C18H40N4P+·Cl·2H2OZ = 4
Mr = 414.99F(000) = 912
Triclinic, P1Dx = 1.123 Mg m3
a = 10.0945 (19) ÅMo Kα radiation, λ = 0.71073 Å
b = 15.759 (3) ÅCell parameters from 4603 reflections
c = 16.122 (3) Åθ = 2.1–19.9°
α = 106.720 (8)°µ = 0.24 mm1
β = 92.259 (8)°T = 296 K
γ = 90.616 (8)°Block, colourless
V = 2453.6 (8) Å30.20 × 0.15 × 0.14 mm
Data collection top
Bruker APEXII CCD
diffractometer
9856 independent reflections
Radiation source: fine-focus sealed tube5364 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
ϕ and ω scansθmax = 26.6°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1212
Tmin = 0.954, Tmax = 0.967k = 1918
35181 measured reflectionsl = 1919
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.212H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.1089P)2 + 0.247P]
where P = (Fo2 + 2Fc2)/3
9856 reflections(Δ/σ)max = 0.011
568 parametersΔρmax = 0.39 e Å3
18 restraintsΔρmin = 0.31 e Å3
Crystal data top
C18H40N4P+·Cl·2H2Oγ = 90.616 (8)°
Mr = 414.99V = 2453.6 (8) Å3
Triclinic, P1Z = 4
a = 10.0945 (19) ÅMo Kα radiation
b = 15.759 (3) ŵ = 0.24 mm1
c = 16.122 (3) ÅT = 296 K
α = 106.720 (8)°0.20 × 0.15 × 0.14 mm
β = 92.259 (8)°
Data collection top
Bruker APEXII CCD
diffractometer
9856 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
5364 reflections with I > 2σ(I)
Tmin = 0.954, Tmax = 0.967Rint = 0.063
35181 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06818 restraints
wR(F2) = 0.212H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.39 e Å3
9856 reflectionsΔρmin = 0.31 e Å3
568 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P10.47871 (8)0.18003 (5)0.25193 (4)0.0476 (2)
H10.51650.16430.18630.057*
N10.4185 (3)0.07779 (17)0.23900 (15)0.0595 (7)
N20.3761 (3)0.25637 (18)0.23615 (16)0.0628 (7)
N30.6278 (3)0.2097 (2)0.29888 (15)0.0680 (8)
N40.4135 (3)0.20879 (19)0.37035 (15)0.0666 (8)
C130.4487 (3)0.00250 (19)0.16562 (18)0.0547 (8)
H13A0.49290.04150.18750.066*
H13B0.51040.02240.13010.066*
C140.3291 (3)0.0414 (2)0.10863 (19)0.0589 (8)
H140.26760.06160.14490.071*
C150.2569 (4)0.0221 (3)0.0690 (3)0.0878 (12)
H15A0.31680.04520.03570.132*
H15B0.22380.07000.11430.132*
H15C0.18410.00860.03200.132*
C160.3732 (4)0.1225 (2)0.0384 (2)0.0838 (11)
H16A0.43210.10410.00120.126*
H16B0.29690.15260.00480.126*
H16C0.41830.16200.06500.126*
C230.3569 (3)0.2767 (2)0.15394 (19)0.0576 (8)
H23A0.26310.27060.13730.069*
H23B0.40270.23310.11000.069*
C240.4048 (4)0.3687 (2)0.1538 (2)0.0715 (10)
H240.35220.41270.19400.086*
C250.5489 (4)0.3849 (3)0.1837 (3)0.1022 (14)
H25A0.60150.34020.14690.153*
H25B0.55950.38240.24240.153*
H25C0.57710.44230.18080.153*
C260.3807 (5)0.3789 (3)0.0633 (3)0.1052 (15)
H26A0.43670.33940.02370.158*
H26B0.40080.43890.06430.158*
H26C0.28950.36470.04490.158*
C330.7437 (3)0.2225 (3)0.2514 (2)0.0786 (11)
H33A0.77080.28450.27150.094*
H33B0.71710.20940.19050.094*
C340.8623 (4)0.1676 (3)0.2595 (3)0.0949 (14)
H340.89660.18650.31980.114*
C350.8185 (6)0.0707 (3)0.2372 (4)0.153 (2)
H35A0.78530.05090.17810.230*
H35B0.74980.06430.27470.230*
H35C0.89270.03570.24490.230*
C360.9706 (5)0.1782 (5)0.2028 (4)0.187 (3)
H36A0.93950.15790.14320.280*
H36B1.04520.14410.21180.280*
H36C0.99700.23960.21690.280*
C11A0.3519 (12)0.0572 (11)0.3116 (10)0.064 (4)0.578 (9)
H11A0.25660.06250.30540.077*0.578 (9)
H11B0.37100.00260.31280.077*0.578 (9)
C12A0.4050 (11)0.1221 (5)0.3914 (4)0.082 (3)0.578 (9)
H12A0.49190.10510.40790.098*0.578 (9)
H12B0.34640.12630.43860.098*0.578 (9)
C21A0.2888 (16)0.2973 (9)0.3003 (10)0.069 (4)0.578 (9)
H21A0.20200.30070.27350.083*0.578 (9)
H21B0.32060.35720.32930.083*0.578 (9)
C22A0.2774 (8)0.2474 (6)0.3645 (4)0.085 (3)0.578 (9)
H22A0.21010.20070.34540.102*0.578 (9)
H22B0.25460.28640.42030.102*0.578 (9)
C31A0.6527 (14)0.2340 (12)0.3908 (10)0.090 (6)0.578 (9)
H31A0.72040.28050.40960.108*0.578 (9)
H31B0.67920.18350.41000.108*0.578 (9)
C32A0.5063 (9)0.2696 (7)0.4264 (4)0.095 (3)0.578 (9)
H32A0.49840.26910.48600.114*0.578 (9)
H32B0.49260.32930.42290.114*0.578 (9)
C11B0.352 (3)0.0518 (19)0.3059 (18)0.128 (11)0.422 (9)
H11C0.41040.01930.33420.153*0.422 (9)
H11D0.27360.01520.28210.153*0.422 (9)
C12B0.3107 (14)0.1463 (8)0.3741 (7)0.089 (4)0.422 (9)
H12C0.22520.16490.35700.106*0.422 (9)
H12D0.30650.14080.43240.106*0.422 (9)
C21B0.311 (2)0.3230 (14)0.3157 (14)0.076 (6)0.422 (9)
H21C0.32660.38380.31560.091*0.422 (9)
H21D0.21600.31170.31420.091*0.422 (9)
C22B0.3783 (11)0.3057 (7)0.3948 (5)0.077 (4)0.422 (9)
H22C0.45770.34270.41250.093*0.422 (9)
H22D0.31910.31910.44260.093*0.422 (9)
C31B0.638 (3)0.2444 (19)0.3975 (16)0.116 (10)0.422 (9)
H31C0.72530.23280.41930.140*0.422 (9)
H31D0.62440.30770.41650.140*0.422 (9)
C32B0.5336 (13)0.1961 (11)0.4291 (6)0.095 (4)0.422 (9)
H32C0.51900.22300.49010.113*0.422 (9)
H32D0.55380.13410.41920.113*0.422 (9)
P20.00164 (8)0.67818 (5)0.25974 (4)0.0463 (2)
H20.03580.66340.19320.056*
N50.1546 (3)0.67602 (17)0.30179 (15)0.0571 (7)
N60.0976 (3)0.58841 (17)0.23778 (14)0.0585 (7)
N70.0637 (3)0.77358 (17)0.25760 (15)0.0644 (7)
N80.0565 (3)0.70466 (19)0.37922 (15)0.0634 (7)
C410.1248 (5)0.8303 (3)0.3349 (3)0.0971 (14)
H41A0.20280.85820.31860.116*
H41B0.06250.87610.36770.116*
C420.1624 (5)0.7683 (3)0.3881 (3)0.1092 (16)
H42A0.17030.80140.44840.131*
H42B0.24640.73800.36630.131*
C430.0232 (3)0.8174 (2)0.1939 (2)0.0599 (8)
H43A0.06530.79870.17680.072*
H43B0.01840.88080.22170.072*
C440.1139 (4)0.7998 (3)0.1120 (2)0.0772 (11)
H440.11350.73580.08370.093*
C450.0542 (5)0.8441 (3)0.0499 (3)0.1091 (15)
H45A0.10880.83110.00250.164*
H45B0.03330.82230.03670.164*
H45C0.04910.90710.07620.164*
C460.2533 (4)0.8234 (3)0.1279 (3)0.1177 (16)
H46A0.25810.88560.15700.177*
H46B0.28940.79020.16350.177*
H46C0.30340.80980.07370.177*
C510.1787 (4)0.6952 (3)0.3955 (2)0.0859 (12)
H51A0.25800.73220.41420.103*
H51B0.19070.64070.41110.103*
C520.0604 (5)0.7423 (3)0.4373 (2)0.1013 (15)
H52A0.05070.73330.49380.122*
H52B0.06960.80540.44460.122*
C530.2650 (3)0.6351 (2)0.2489 (2)0.0605 (8)
H53A0.23350.61450.18870.073*
H53B0.29240.58360.26620.073*
C540.3857 (4)0.6966 (2)0.2560 (2)0.0732 (10)
H540.42060.71350.31620.088*
C550.4924 (4)0.6446 (3)0.1989 (4)0.1183 (17)
H55A0.46510.63380.13890.177*
H55B0.50480.58910.21120.177*
H55C0.57430.67830.21060.177*
C560.3497 (4)0.7796 (3)0.2337 (3)0.0973 (13)
H56A0.42710.81730.24040.146*
H56B0.28350.81000.27160.146*
H56C0.31550.76470.17470.146*
C610.1721 (4)0.5683 (3)0.3062 (2)0.0801 (11)
H61A0.17430.50500.29910.096*
H61B0.26250.58840.30510.096*
C620.0976 (5)0.6183 (3)0.3917 (2)0.0916 (13)
H62A0.15510.62730.44020.110*
H62B0.02080.58580.40230.110*
C630.1421 (3)0.5396 (2)0.14950 (18)0.0564 (8)
H63A0.10100.56670.10980.068*
H63B0.23720.54600.14360.068*
C640.1124 (4)0.4416 (2)0.1222 (2)0.0792 (11)
H640.16140.41460.15970.095*
C650.1675 (5)0.4001 (3)0.0296 (3)0.1206 (18)
H65A0.26180.40710.02730.181*
H65B0.14800.33810.01160.181*
H65C0.12740.42880.00850.181*
C660.0313 (5)0.4249 (3)0.1354 (4)0.136 (2)
H66A0.08310.45260.10130.203*
H66B0.04560.36220.11780.203*
H66C0.05760.44910.19560.203*
Cl10.74844 (12)0.48539 (9)0.49895 (10)0.1183 (5)
Cl20.24967 (11)0.95105 (8)0.49482 (9)0.1136 (4)
O10.0445 (6)0.0588 (3)0.4090 (3)0.1250 (13)
H1010.033 (6)0.050 (4)0.422 (4)0.14 (3)*
H1020.086 (8)0.016 (6)0.430 (5)0.25 (4)*
O20.4520 (7)0.1069 (3)0.5950 (3)0.1382 (16)
H1030.530 (7)0.088 (4)0.584 (4)0.16 (3)*
H1040.403 (8)0.066 (6)0.570 (5)0.24 (5)*
O30.0019 (6)0.6098 (3)0.6065 (3)0.1294 (15)
H1050.076 (5)0.593 (3)0.591 (3)0.098 (17)*
H1060.072 (4)0.578 (3)0.588 (3)0.091 (17)*
O40.5064 (6)0.5514 (4)0.3944 (3)0.1389 (17)
H1070.551 (6)0.506 (4)0.414 (4)0.16 (3)*
H1080.448 (5)0.541 (3)0.415 (3)0.086 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0493 (5)0.0529 (5)0.0378 (4)0.0011 (4)0.0066 (3)0.0077 (3)
N10.0780 (19)0.0541 (16)0.0458 (13)0.0067 (14)0.0140 (13)0.0121 (12)
N20.0663 (18)0.0635 (18)0.0593 (15)0.0197 (15)0.0190 (13)0.0157 (13)
N30.0575 (18)0.091 (2)0.0497 (14)0.0071 (16)0.0033 (13)0.0116 (14)
N40.081 (2)0.074 (2)0.0421 (13)0.0076 (17)0.0139 (13)0.0101 (13)
C130.061 (2)0.0480 (18)0.0553 (17)0.0068 (15)0.0082 (14)0.0145 (14)
C140.061 (2)0.059 (2)0.0570 (17)0.0051 (16)0.0069 (15)0.0158 (15)
C150.080 (3)0.083 (3)0.098 (3)0.005 (2)0.020 (2)0.027 (2)
C160.108 (3)0.065 (2)0.069 (2)0.006 (2)0.008 (2)0.0044 (18)
C230.052 (2)0.057 (2)0.0640 (18)0.0018 (16)0.0011 (15)0.0186 (15)
C240.071 (3)0.057 (2)0.091 (2)0.0041 (18)0.0058 (19)0.0276 (18)
C250.077 (3)0.082 (3)0.156 (4)0.017 (2)0.006 (3)0.050 (3)
C260.129 (4)0.093 (3)0.114 (3)0.005 (3)0.007 (3)0.061 (3)
C330.059 (2)0.088 (3)0.082 (2)0.002 (2)0.0052 (19)0.016 (2)
C340.081 (3)0.088 (3)0.102 (3)0.025 (2)0.013 (2)0.006 (2)
C350.161 (5)0.079 (4)0.191 (6)0.024 (4)0.041 (4)0.001 (3)
C360.060 (3)0.286 (9)0.191 (6)0.002 (4)0.037 (4)0.028 (6)
C11A0.077 (6)0.070 (7)0.056 (7)0.012 (5)0.022 (5)0.033 (6)
C12A0.102 (7)0.095 (6)0.055 (4)0.014 (5)0.030 (4)0.029 (4)
C21A0.084 (7)0.052 (8)0.065 (6)0.019 (6)0.003 (4)0.006 (6)
C22A0.083 (6)0.105 (7)0.065 (4)0.025 (5)0.034 (4)0.018 (4)
C31A0.073 (8)0.127 (10)0.049 (6)0.049 (8)0.005 (5)0.006 (6)
C32A0.134 (9)0.094 (6)0.042 (3)0.011 (6)0.004 (4)0.002 (4)
C11B0.21 (2)0.084 (14)0.069 (13)0.002 (14)0.044 (13)0.011 (10)
C12B0.096 (9)0.084 (8)0.079 (7)0.023 (7)0.051 (7)0.008 (6)
C21B0.086 (10)0.055 (10)0.072 (9)0.006 (7)0.051 (8)0.012 (7)
C22B0.079 (8)0.081 (7)0.057 (5)0.001 (6)0.026 (5)0.008 (4)
C31B0.115 (16)0.165 (18)0.054 (11)0.067 (14)0.036 (10)0.008 (10)
C32B0.106 (9)0.136 (12)0.042 (5)0.012 (9)0.014 (5)0.026 (6)
P20.0527 (5)0.0490 (5)0.0377 (4)0.0003 (4)0.0066 (3)0.0127 (3)
N50.0556 (17)0.0674 (17)0.0497 (13)0.0043 (14)0.0030 (12)0.0198 (12)
N60.0673 (17)0.0603 (17)0.0448 (13)0.0160 (14)0.0048 (12)0.0103 (12)
N70.083 (2)0.0593 (17)0.0530 (14)0.0176 (15)0.0152 (13)0.0167 (12)
N80.075 (2)0.0684 (18)0.0432 (13)0.0108 (16)0.0101 (13)0.0100 (12)
C410.129 (4)0.078 (3)0.082 (3)0.036 (3)0.041 (3)0.014 (2)
C420.128 (4)0.128 (4)0.071 (2)0.042 (3)0.043 (2)0.021 (2)
C430.059 (2)0.0486 (19)0.074 (2)0.0025 (16)0.0026 (16)0.0218 (16)
C440.069 (3)0.084 (3)0.089 (2)0.006 (2)0.008 (2)0.045 (2)
C450.122 (4)0.125 (4)0.102 (3)0.013 (3)0.004 (3)0.068 (3)
C460.076 (3)0.136 (4)0.146 (4)0.001 (3)0.015 (3)0.052 (3)
C510.086 (3)0.116 (3)0.058 (2)0.016 (3)0.011 (2)0.032 (2)
C520.116 (4)0.131 (4)0.0467 (19)0.021 (3)0.002 (2)0.011 (2)
C530.051 (2)0.056 (2)0.079 (2)0.0014 (16)0.0035 (16)0.0261 (16)
C540.063 (2)0.070 (2)0.093 (2)0.0080 (19)0.0074 (19)0.034 (2)
C550.060 (3)0.098 (3)0.195 (5)0.003 (3)0.030 (3)0.037 (3)
C560.084 (3)0.078 (3)0.145 (4)0.015 (2)0.005 (3)0.059 (3)
C610.089 (3)0.088 (3)0.0593 (19)0.028 (2)0.0184 (19)0.0147 (18)
C620.125 (4)0.096 (3)0.058 (2)0.022 (3)0.023 (2)0.027 (2)
C630.0521 (19)0.062 (2)0.0509 (16)0.0023 (16)0.0014 (14)0.0099 (14)
C640.081 (3)0.060 (2)0.088 (2)0.001 (2)0.015 (2)0.0070 (19)
C650.154 (5)0.092 (3)0.083 (3)0.022 (3)0.017 (3)0.027 (2)
C660.094 (4)0.088 (4)0.215 (6)0.031 (3)0.023 (4)0.024 (3)
Cl10.0861 (8)0.1121 (10)0.1764 (13)0.0095 (7)0.0333 (8)0.0692 (9)
Cl20.0769 (8)0.1007 (9)0.1633 (12)0.0105 (6)0.0060 (7)0.0387 (8)
O10.114 (3)0.133 (3)0.139 (3)0.003 (3)0.023 (3)0.055 (3)
O20.125 (4)0.140 (4)0.121 (3)0.002 (3)0.002 (3)0.007 (2)
O30.127 (4)0.128 (3)0.112 (3)0.022 (3)0.012 (3)0.001 (2)
O40.136 (4)0.192 (5)0.109 (3)0.017 (3)0.030 (3)0.071 (3)
Geometric parameters (Å, º) top
P1—N31.658 (3)C22B—H22D0.9700
P1—N21.664 (3)C31B—C32B1.48 (3)
P1—N11.669 (3)C31B—H31C0.9700
P1—N41.973 (2)C31B—H31D0.9700
P1—H11.1000C32B—H32C0.9700
N1—C11B1.45 (3)C32B—H32D0.9700
N1—C131.459 (4)P2—N71.657 (3)
N1—C11A1.484 (12)P2—N51.666 (3)
N2—C21A1.400 (16)P2—N61.669 (3)
N2—C231.457 (4)P2—N81.965 (2)
N2—C21B1.577 (19)P2—H21.1000
N3—C31A1.431 (15)N5—C511.463 (4)
N3—C331.466 (4)N5—C531.470 (4)
N3—C31B1.52 (2)N6—C631.460 (3)
N4—C32A1.424 (8)N6—C611.465 (4)
N4—C12B1.438 (10)N7—C431.460 (4)
N4—C12A1.502 (8)N7—C411.470 (4)
N4—C22B1.513 (10)N8—C421.456 (5)
N4—C22A1.519 (7)N8—C521.483 (5)
N4—C32B1.559 (12)N8—C621.489 (5)
C13—C141.519 (4)C41—C421.528 (6)
C13—H13A0.9700C41—H41A0.9700
C13—H13B0.9700C41—H41B0.9700
C14—C151.513 (5)C42—H42A0.9700
C14—C161.528 (4)C42—H42B0.9700
C14—H140.9800C43—C441.533 (4)
C15—H15A0.9600C43—H43A0.9700
C15—H15B0.9600C43—H43B0.9700
C15—H15C0.9600C44—C461.473 (5)
C16—H16A0.9600C44—C451.515 (5)
C16—H16B0.9600C44—H440.9800
C16—H16C0.9600C45—H45A0.9600
C23—C241.524 (4)C45—H45B0.9600
C23—H23A0.9700C45—H45C0.9600
C23—H23B0.9700C46—H46A0.9600
C24—C251.509 (5)C46—H46B0.9600
C24—C261.523 (5)C46—H46C0.9600
C24—H240.9800C51—C521.493 (6)
C25—H25A0.9600C51—H51A0.9700
C25—H25B0.9600C51—H51B0.9700
C25—H25C0.9600C52—H52A0.9700
C26—H26A0.9600C52—H52B0.9700
C26—H26B0.9600C53—C541.530 (5)
C26—H26C0.9600C53—H53A0.9700
C33—C341.508 (5)C53—H53B0.9700
C33—H33A0.9700C54—C561.497 (5)
C33—H33B0.9700C54—C551.530 (5)
C34—C361.491 (7)C54—H540.9800
C34—C351.521 (6)C55—H55A0.9600
C34—H340.9800C55—H55B0.9600
C35—H35A0.9600C55—H55C0.9600
C35—H35B0.9600C56—H56A0.9600
C35—H35C0.9600C56—H56B0.9600
C36—H36A0.9600C56—H56C0.9600
C36—H36B0.9600C61—C621.538 (5)
C36—H36C0.9600C61—H61A0.9700
C11A—C12A1.470 (18)C61—H61B0.9700
C11A—H11A0.9700C62—H62A0.9700
C11A—H11B0.9700C62—H62B0.9700
C12A—H12A0.9700C63—C641.515 (4)
C12A—H12B0.9700C63—H63A0.9700
C21A—C22A1.476 (17)C63—H63B0.9700
C21A—H21A0.9700C64—C661.495 (6)
C21A—H21B0.9700C64—C651.527 (5)
C22A—H22A0.9700C64—H640.9800
C22A—H22B0.9700C65—H65A0.9600
C31A—C32A1.65 (2)C65—H65B0.9600
C31A—H31A0.9700C65—H65C0.9600
C31A—H31B0.9700C66—H66A0.9600
C32A—H32A0.9700C66—H66B0.9600
C32A—H32B0.9700C66—H66C0.9600
C11B—C12B1.64 (3)O1—H1010.84 (6)
C11B—H11C0.9700O1—H1020.94 (9)
C11B—H11D0.9700O2—H1030.85 (7)
C12B—H12C0.9700O2—H1040.80 (8)
C12B—H12D0.9700O3—H1050.85 (4)
C21B—C22B1.52 (3)O3—H1060.86 (4)
C21B—H21C0.9700O4—H1070.97 (6)
C21B—H21D0.9700O4—H1080.73 (4)
C22B—H22C0.9700
N3—P1—N2120.17 (15)C22B—C21B—H21C110.8
N3—P1—N1120.09 (15)N2—C21B—H21C110.8
N2—P1—N1118.53 (15)C22B—C21B—H21D110.8
N3—P1—N486.27 (13)N2—C21B—H21D110.8
N2—P1—N486.52 (12)H21C—C21B—H21D108.9
N1—P1—N486.24 (12)N4—C22B—C21B107.5 (9)
N3—P1—H192.9N4—C22B—H22C110.2
N2—P1—H193.9C21B—C22B—H22C110.2
N1—P1—H194.2N4—C22B—H22D110.2
N4—P1—H1179.2C21B—C22B—H22D110.2
C11B—N1—C13112.8 (11)H22C—C22B—H22D108.5
C13—N1—C11A116.6 (7)C32B—C31B—N3105.9 (16)
C11B—N1—P1123.3 (11)C32B—C31B—H31C110.6
C13—N1—P1123.0 (2)N3—C31B—H31C110.6
C11A—N1—P1119.5 (7)C32B—C31B—H31D110.6
C21A—N2—C23115.4 (6)N3—C31B—H31D110.6
C23—N2—C21B115.1 (9)H31C—C31B—H31D108.7
C21A—N2—P1120.0 (6)C31B—C32B—N499.7 (10)
C23—N2—P1124.0 (2)C31B—C32B—H32C111.8
C21B—N2—P1120.2 (9)N4—C32B—H32C111.8
C31A—N3—C33113.3 (6)C31B—C32B—H32D111.8
C33—N3—C31B117.4 (11)N4—C32B—H32D111.8
C31A—N3—P1123.0 (6)H32C—C32B—H32D109.6
C33—N3—P1123.4 (2)N7—P2—N5120.29 (14)
C31B—N3—P1117.9 (10)N7—P2—N6118.48 (15)
C32A—N4—C12B139.9 (6)N5—P2—N6120.12 (14)
C32A—N4—C12A112.5 (6)N7—P2—N886.81 (12)
C12B—N4—C22B117.2 (7)N5—P2—N886.24 (12)
C12A—N4—C22B147.4 (5)N6—P2—N886.40 (11)
C32A—N4—C22A113.5 (5)N7—P2—H293.6
C12A—N4—C22A111.7 (5)N5—P2—H292.9
C12B—N4—C32B107.8 (8)N6—P2—H294.1
C22B—N4—C32B109.4 (7)N8—P2—H2179.1
C22A—N4—C32B147.8 (5)C51—N5—C53115.2 (3)
C32A—N4—P1107.7 (4)C51—N5—P2120.7 (2)
C12B—N4—P1109.9 (4)C53—N5—P2122.48 (19)
C12A—N4—P1105.6 (3)C63—N6—C61115.0 (3)
C22B—N4—P1106.3 (4)C63—N6—P2122.5 (2)
C22A—N4—P1105.3 (3)C61—N6—P2120.7 (2)
C32B—N4—P1105.7 (4)C43—N7—C41116.0 (3)
N1—C13—C14114.8 (3)C43—N7—P2120.5 (2)
N1—C13—H13A108.6C41—N7—P2120.2 (2)
C14—C13—H13A108.6C42—N8—C52111.8 (3)
N1—C13—H13B108.6C42—N8—C62114.4 (3)
C14—C13—H13B108.6C52—N8—C62109.9 (3)
H13A—C13—H13B107.5C42—N8—P2107.1 (2)
C15—C14—C13112.1 (3)C52—N8—P2106.9 (2)
C15—C14—C16110.9 (3)C62—N8—P2106.33 (19)
C13—C14—C16109.5 (3)N7—C41—C42105.4 (3)
C15—C14—H14108.1N7—C41—H41A110.7
C13—C14—H14108.1C42—C41—H41A110.7
C16—C14—H14108.1N7—C41—H41B110.7
C14—C15—H15A109.5C42—C41—H41B110.7
C14—C15—H15B109.5H41A—C41—H41B108.8
H15A—C15—H15B109.5N8—C42—C41106.4 (3)
C14—C15—H15C109.5N8—C42—H42A110.5
H15A—C15—H15C109.5C41—C42—H42A110.5
H15B—C15—H15C109.5N8—C42—H42B110.5
C14—C16—H16A109.5C41—C42—H42B110.5
C14—C16—H16B109.5H42A—C42—H42B108.6
H16A—C16—H16B109.5N7—C43—C44115.5 (3)
C14—C16—H16C109.5N7—C43—H43A108.4
H16A—C16—H16C109.5C44—C43—H43A108.4
H16B—C16—H16C109.5N7—C43—H43B108.4
N2—C23—C24115.5 (3)C44—C43—H43B108.4
N2—C23—H23A108.4H43A—C43—H43B107.5
C24—C23—H23A108.4C46—C44—C45112.2 (3)
N2—C23—H23B108.4C46—C44—C43114.7 (3)
C24—C23—H23B108.4C45—C44—C43109.3 (3)
H23A—C23—H23B107.5C46—C44—H44106.7
C25—C24—C26111.6 (4)C45—C44—H44106.7
C25—C24—C23111.4 (3)C43—C44—H44106.7
C26—C24—C23109.0 (3)C44—C45—H45A109.5
C25—C24—H24108.3C44—C45—H45B109.5
C26—C24—H24108.3H45A—C45—H45B109.5
C23—C24—H24108.3C44—C45—H45C109.5
C24—C25—H25A109.5H45A—C45—H45C109.5
C24—C25—H25B109.5H45B—C45—H45C109.5
H25A—C25—H25B109.5C44—C46—H46A109.5
C24—C25—H25C109.5C44—C46—H46B109.5
H25A—C25—H25C109.5H46A—C46—H46B109.5
H25B—C25—H25C109.5C44—C46—H46C109.5
C24—C26—H26A109.5H46A—C46—H46C109.5
C24—C26—H26B109.5H46B—C46—H46C109.5
H26A—C26—H26B109.5N5—C51—C52106.9 (3)
C24—C26—H26C109.5N5—C51—H51A110.3
H26A—C26—H26C109.5C52—C51—H51A110.3
H26B—C26—H26C109.5N5—C51—H51B110.3
N3—C33—C34115.9 (4)C52—C51—H51B110.3
N3—C33—H33A108.3H51A—C51—H51B108.6
C34—C33—H33A108.3N8—C52—C51106.9 (3)
N3—C33—H33B108.3N8—C52—H52A110.3
C34—C33—H33B108.3C51—C52—H52A110.3
H33A—C33—H33B107.4N8—C52—H52B110.3
C36—C34—C33112.4 (5)C51—C52—H52B110.3
C36—C34—C35110.1 (5)H52A—C52—H52B108.6
C33—C34—C35109.1 (4)N5—C53—C54114.4 (3)
C36—C34—H34108.4N5—C53—H53A108.7
C33—C34—H34108.4C54—C53—H53A108.7
C35—C34—H34108.4N5—C53—H53B108.7
C34—C35—H35A109.5C54—C53—H53B108.7
C34—C35—H35B109.5H53A—C53—H53B107.6
H35A—C35—H35B109.5C56—C54—C53111.7 (3)
C34—C35—H35C109.5C56—C54—C55112.7 (4)
H35A—C35—H35C109.5C53—C54—C55108.3 (3)
H35B—C35—H35C109.5C56—C54—H54108.0
C34—C36—H36A109.5C53—C54—H54108.0
C34—C36—H36B109.5C55—C54—H54108.0
H36A—C36—H36B109.5C54—C55—H55A109.5
C34—C36—H36C109.5C54—C55—H55B109.5
H36A—C36—H36C109.5H55A—C55—H55B109.5
H36B—C36—H36C109.5C54—C55—H55C109.5
C12A—C11A—N1106.2 (9)H55A—C55—H55C109.5
C12A—C11A—H11A110.5H55B—C55—H55C109.5
N1—C11A—H11A110.5C54—C56—H56A109.5
C12A—C11A—H11B110.5C54—C56—H56B109.5
N1—C11A—H11B110.5H56A—C56—H56B109.5
H11A—C11A—H11B108.7C54—C56—H56C109.5
C11A—C12A—N4105.6 (7)H56A—C56—H56C109.5
C11A—C12A—H12A110.6H56B—C56—H56C109.5
N4—C12A—H12A110.6N6—C61—C62105.4 (3)
C11A—C12A—H12B110.6N6—C61—H61A110.7
N4—C12A—H12B110.6C62—C61—H61A110.7
H12A—C12A—H12B108.7N6—C61—H61B110.7
N2—C21A—C22A111.0 (9)C62—C61—H61B110.7
N2—C21A—H21A109.4H61A—C61—H61B108.8
C22A—C21A—H21A109.4N8—C62—C61104.7 (3)
N2—C21A—H21B109.4N8—C62—H62A110.8
C22A—C21A—H21B109.4C61—C62—H62A110.8
H21A—C21A—H21B108.0N8—C62—H62B110.8
C21A—C22A—N4104.9 (8)C61—C62—H62B110.8
C21A—C22A—H22A110.8H62A—C62—H62B108.9
N4—C22A—H22A110.8N6—C63—C64115.6 (3)
C21A—C22A—H22B110.8N6—C63—H63A108.4
N4—C22A—H22B110.8C64—C63—H63A108.4
H22A—C22A—H22B108.8N6—C63—H63B108.4
N3—C31A—C32A101.6 (9)C64—C63—H63B108.4
N3—C31A—H31A111.4H63A—C63—H63B107.5
C32A—C31A—H31A111.4C66—C64—C63112.3 (3)
N3—C31A—H31B111.4C66—C64—C65114.0 (4)
C32A—C31A—H31B111.4C63—C64—C65109.1 (3)
H31A—C31A—H31B109.3C66—C64—H64107.1
N4—C32A—C31A104.6 (7)C63—C64—H64107.1
N4—C32A—H32A110.8C65—C64—H64107.1
C31A—C32A—H32A110.8C64—C65—H65A109.5
N4—C32A—H32B110.8C64—C65—H65B109.5
C31A—C32A—H32B110.8H65A—C65—H65B109.5
H32A—C32A—H32B108.9C64—C65—H65C109.5
N1—C11B—C12B104.1 (18)H65A—C65—H65C109.5
N1—C11B—H11C110.9H65B—C65—H65C109.5
C12B—C11B—H11C110.9C64—C66—H66A109.5
N1—C11B—H11D110.9C64—C66—H66B109.5
C12B—C11B—H11D110.9H66A—C66—H66B109.5
H11C—C11B—H11D109.0C64—C66—H66C109.5
N4—C12B—C11B105.4 (12)H66A—C66—H66C109.5
N4—C12B—H12C110.7H66B—C66—H66C109.5
C11B—C12B—H12C110.7H101—O1—H10298 (6)
N4—C12B—H12D110.7H103—O2—H104105 (7)
C11B—C12B—H12D110.7H105—O3—H106123 (5)
H12C—C12B—H12D108.8H107—O4—H10886 (5)
C22B—C21B—N2104.7 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H101···Cl2i0.84 (6)2.61 (6)3.426 (6)164 (5)
O1—H102···Cl2ii0.93 (9)2.32 (9)3.208 (6)159 (7)
O2—H103···Cl2iii0.85 (7)2.60 (7)3.412 (7)161 (5)
O2—H104···Cl2ii0.81 (8)2.38 (9)3.188 (6)177 (8)
O3—H105···Cl1iii0.86 (5)2.45 (5)3.263 (6)159 (4)
O3—H106···Cl1iv0.85 (4)2.45 (4)3.286 (6)165 (4)
O4—H108···Cl1iii0.73 (5)2.56 (5)3.286 (6)175 (4)
Symmetry codes: (i) x, y+1, z+1; (ii) x, y1, z; (iii) x+1, y+1, z+1; (iv) x1, y, z.

Experimental details

Crystal data
Chemical formulaC18H40N4P+·Cl·2H2O
Mr414.99
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)10.0945 (19), 15.759 (3), 16.122 (3)
α, β, γ (°)106.720 (8), 92.259 (8), 90.616 (8)
V3)2453.6 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.20 × 0.15 × 0.14
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.954, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections
35181, 9856, 5364
Rint0.063
(sin θ/λ)max1)0.631
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.212, 1.01
No. of reflections9856
No. of parameters568
No. of restraints18
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.39, 0.31

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H101···Cl2i0.84 (6)2.61 (6)3.426 (6)164 (5)
O1—H102···Cl2ii0.93 (9)2.32 (9)3.208 (6)159 (7)
O2—H103···Cl2iii0.85 (7)2.60 (7)3.412 (7)161 (5)
O2—H104···Cl2ii0.81 (8)2.38 (9)3.188 (6)177 (8)
O3—H105···Cl1iii0.86 (5)2.45 (5)3.263 (6)159 (4)
O3—H106···Cl1iv0.85 (4)2.45 (4)3.286 (6)165 (4)
O4—H108···Cl1iii0.73 (5)2.56 (5)3.286 (6)175 (4)
Symmetry codes: (i) x, y+1, z+1; (ii) x, y1, z; (iii) x+1, y+1, z+1; (iv) x1, y, z.
 

Acknowledgements

This work was supported by a research grant from Chungbuk Nation University in 2012.

References

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