organic compounds
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
The 18H40N4P+·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).
of the title hydrated salt, CRelated literature
For background to the applications of related compounds, see: Raders & Verkade (2010); Tang et al. (1993); Verkade & Kisang (2003); Zhou et al. (2011). For similar structure types, see: Kingston & Verkade (2005); Kisanga & Verkade (2001); Liu et al. (1999, 2000); Mohan et al. (1996); Thirupathi et al. (2003); Wroblewski et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT; 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.
Supporting information
10.1107/S1600536812045618/ff2086sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812045618/ff2086Isup3.hkl
Supporting information file. DOI: 10.1107/S1600536812045618/ff2086Isup4.cdx
Supporting information file. DOI: 10.1107/S1600536812045618/ff2086Isup4.cml
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.
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.
Data collection: APEX2 (Bruker, 2004); cell
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).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. |
C18H40N4P+·Cl−·2H2O | Z = 4 |
Mr = 414.99 | F(000) = 912 |
Triclinic, P1 | Dx = 1.123 Mg m−3 |
a = 10.0945 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 15.759 (3) Å | Cell parameters from 4603 reflections |
c = 16.122 (3) Å | θ = 2.1–19.9° |
α = 106.720 (8)° | µ = 0.24 mm−1 |
β = 92.259 (8)° | T = 296 K |
γ = 90.616 (8)° | Block, colourless |
V = 2453.6 (8) Å3 | 0.20 × 0.15 × 0.14 mm |
Bruker APEXII CCD diffractometer | 9856 independent reflections |
Radiation source: fine-focus sealed tube | 5364 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
ϕ and ω scans | θmax = 26.6°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −12→12 |
Tmin = 0.954, Tmax = 0.967 | k = −19→18 |
35181 measured reflections | l = −19→19 |
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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.212 | H 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 parameters | Δρmax = 0.39 e Å−3 |
18 restraints | Δρmin = −0.31 e Å−3 |
C18H40N4P+·Cl−·2H2O | γ = 90.616 (8)° |
Mr = 414.99 | V = 2453.6 (8) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.0945 (19) Å | Mo Kα radiation |
b = 15.759 (3) Å | µ = 0.24 mm−1 |
c = 16.122 (3) Å | T = 296 K |
α = 106.720 (8)° | 0.20 × 0.15 × 0.14 mm |
β = 92.259 (8)° |
Bruker APEXII CCD diffractometer | 9856 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 5364 reflections with I > 2σ(I) |
Tmin = 0.954, Tmax = 0.967 | Rint = 0.063 |
35181 measured reflections |
R[F2 > 2σ(F2)] = 0.068 | 18 restraints |
wR(F2) = 0.212 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.39 e Å−3 |
9856 reflections | Δρmin = −0.31 e Å−3 |
568 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
P1 | 0.47871 (8) | 0.18003 (5) | 0.25193 (4) | 0.0476 (2) | |
H1 | 0.5165 | 0.1643 | 0.1863 | 0.057* | |
N1 | 0.4185 (3) | 0.07779 (17) | 0.23900 (15) | 0.0595 (7) | |
N2 | 0.3761 (3) | 0.25637 (18) | 0.23615 (16) | 0.0628 (7) | |
N3 | 0.6278 (3) | 0.2097 (2) | 0.29888 (15) | 0.0680 (8) | |
N4 | 0.4135 (3) | 0.20879 (19) | 0.37035 (15) | 0.0666 (8) | |
C13 | 0.4487 (3) | 0.00250 (19) | 0.16562 (18) | 0.0547 (8) | |
H13A | 0.4929 | −0.0415 | 0.1875 | 0.066* | |
H13B | 0.5104 | 0.0224 | 0.1301 | 0.066* | |
C14 | 0.3291 (3) | −0.0414 (2) | 0.10863 (19) | 0.0589 (8) | |
H14 | 0.2676 | −0.0616 | 0.1449 | 0.071* | |
C15 | 0.2569 (4) | 0.0221 (3) | 0.0690 (3) | 0.0878 (12) | |
H15A | 0.3168 | 0.0452 | 0.0357 | 0.132* | |
H15B | 0.2238 | 0.0700 | 0.1143 | 0.132* | |
H15C | 0.1841 | −0.0086 | 0.0320 | 0.132* | |
C16 | 0.3732 (4) | −0.1225 (2) | 0.0384 (2) | 0.0838 (11) | |
H16A | 0.4321 | −0.1041 | 0.0012 | 0.126* | |
H16B | 0.2969 | −0.1526 | 0.0048 | 0.126* | |
H16C | 0.4183 | −0.1620 | 0.0650 | 0.126* | |
C23 | 0.3569 (3) | 0.2767 (2) | 0.15394 (19) | 0.0576 (8) | |
H23A | 0.2631 | 0.2706 | 0.1373 | 0.069* | |
H23B | 0.4027 | 0.2331 | 0.1100 | 0.069* | |
C24 | 0.4048 (4) | 0.3687 (2) | 0.1538 (2) | 0.0715 (10) | |
H24 | 0.3522 | 0.4127 | 0.1940 | 0.086* | |
C25 | 0.5489 (4) | 0.3849 (3) | 0.1837 (3) | 0.1022 (14) | |
H25A | 0.6015 | 0.3402 | 0.1469 | 0.153* | |
H25B | 0.5595 | 0.3824 | 0.2424 | 0.153* | |
H25C | 0.5771 | 0.4423 | 0.1808 | 0.153* | |
C26 | 0.3807 (5) | 0.3789 (3) | 0.0633 (3) | 0.1052 (15) | |
H26A | 0.4367 | 0.3394 | 0.0237 | 0.158* | |
H26B | 0.4008 | 0.4389 | 0.0643 | 0.158* | |
H26C | 0.2895 | 0.3647 | 0.0449 | 0.158* | |
C33 | 0.7437 (3) | 0.2225 (3) | 0.2514 (2) | 0.0786 (11) | |
H33A | 0.7708 | 0.2845 | 0.2715 | 0.094* | |
H33B | 0.7171 | 0.2094 | 0.1905 | 0.094* | |
C34 | 0.8623 (4) | 0.1676 (3) | 0.2595 (3) | 0.0949 (14) | |
H34 | 0.8966 | 0.1865 | 0.3198 | 0.114* | |
C35 | 0.8185 (6) | 0.0707 (3) | 0.2372 (4) | 0.153 (2) | |
H35A | 0.7853 | 0.0509 | 0.1781 | 0.230* | |
H35B | 0.7498 | 0.0643 | 0.2747 | 0.230* | |
H35C | 0.8927 | 0.0357 | 0.2449 | 0.230* | |
C36 | 0.9706 (5) | 0.1782 (5) | 0.2028 (4) | 0.187 (3) | |
H36A | 0.9395 | 0.1579 | 0.1432 | 0.280* | |
H36B | 1.0452 | 0.1441 | 0.2118 | 0.280* | |
H36C | 0.9970 | 0.2396 | 0.2169 | 0.280* | |
C11A | 0.3519 (12) | 0.0572 (11) | 0.3116 (10) | 0.064 (4) | 0.578 (9) |
H11A | 0.2566 | 0.0625 | 0.3054 | 0.077* | 0.578 (9) |
H11B | 0.3710 | −0.0026 | 0.3128 | 0.077* | 0.578 (9) |
C12A | 0.4050 (11) | 0.1221 (5) | 0.3914 (4) | 0.082 (3) | 0.578 (9) |
H12A | 0.4919 | 0.1051 | 0.4079 | 0.098* | 0.578 (9) |
H12B | 0.3464 | 0.1263 | 0.4386 | 0.098* | 0.578 (9) |
C21A | 0.2888 (16) | 0.2973 (9) | 0.3003 (10) | 0.069 (4) | 0.578 (9) |
H21A | 0.2020 | 0.3007 | 0.2735 | 0.083* | 0.578 (9) |
H21B | 0.3206 | 0.3572 | 0.3293 | 0.083* | 0.578 (9) |
C22A | 0.2774 (8) | 0.2474 (6) | 0.3645 (4) | 0.085 (3) | 0.578 (9) |
H22A | 0.2101 | 0.2007 | 0.3454 | 0.102* | 0.578 (9) |
H22B | 0.2546 | 0.2864 | 0.4203 | 0.102* | 0.578 (9) |
C31A | 0.6527 (14) | 0.2340 (12) | 0.3908 (10) | 0.090 (6) | 0.578 (9) |
H31A | 0.7204 | 0.2805 | 0.4096 | 0.108* | 0.578 (9) |
H31B | 0.6792 | 0.1835 | 0.4100 | 0.108* | 0.578 (9) |
C32A | 0.5063 (9) | 0.2696 (7) | 0.4264 (4) | 0.095 (3) | 0.578 (9) |
H32A | 0.4984 | 0.2691 | 0.4860 | 0.114* | 0.578 (9) |
H32B | 0.4926 | 0.3293 | 0.4229 | 0.114* | 0.578 (9) |
C11B | 0.352 (3) | 0.0518 (19) | 0.3059 (18) | 0.128 (11) | 0.422 (9) |
H11C | 0.4104 | 0.0193 | 0.3342 | 0.153* | 0.422 (9) |
H11D | 0.2736 | 0.0152 | 0.2821 | 0.153* | 0.422 (9) |
C12B | 0.3107 (14) | 0.1463 (8) | 0.3741 (7) | 0.089 (4) | 0.422 (9) |
H12C | 0.2252 | 0.1649 | 0.3570 | 0.106* | 0.422 (9) |
H12D | 0.3065 | 0.1408 | 0.4324 | 0.106* | 0.422 (9) |
C21B | 0.311 (2) | 0.3230 (14) | 0.3157 (14) | 0.076 (6) | 0.422 (9) |
H21C | 0.3266 | 0.3838 | 0.3156 | 0.091* | 0.422 (9) |
H21D | 0.2160 | 0.3117 | 0.3142 | 0.091* | 0.422 (9) |
C22B | 0.3783 (11) | 0.3057 (7) | 0.3948 (5) | 0.077 (4) | 0.422 (9) |
H22C | 0.4577 | 0.3427 | 0.4125 | 0.093* | 0.422 (9) |
H22D | 0.3191 | 0.3191 | 0.4426 | 0.093* | 0.422 (9) |
C31B | 0.638 (3) | 0.2444 (19) | 0.3975 (16) | 0.116 (10) | 0.422 (9) |
H31C | 0.7253 | 0.2328 | 0.4193 | 0.140* | 0.422 (9) |
H31D | 0.6244 | 0.3077 | 0.4165 | 0.140* | 0.422 (9) |
C32B | 0.5336 (13) | 0.1961 (11) | 0.4291 (6) | 0.095 (4) | 0.422 (9) |
H32C | 0.5190 | 0.2230 | 0.4901 | 0.113* | 0.422 (9) |
H32D | 0.5538 | 0.1341 | 0.4192 | 0.113* | 0.422 (9) |
P2 | 0.00164 (8) | 0.67818 (5) | 0.25974 (4) | 0.0463 (2) | |
H2 | 0.0358 | 0.6634 | 0.1932 | 0.056* | |
N5 | 0.1546 (3) | 0.67602 (17) | 0.30179 (15) | 0.0571 (7) | |
N6 | −0.0976 (3) | 0.58841 (17) | 0.23778 (14) | 0.0585 (7) | |
N7 | −0.0637 (3) | 0.77358 (17) | 0.25760 (15) | 0.0644 (7) | |
N8 | −0.0565 (3) | 0.70466 (19) | 0.37922 (15) | 0.0634 (7) | |
C41 | −0.1248 (5) | 0.8303 (3) | 0.3349 (3) | 0.0971 (14) | |
H41A | −0.2028 | 0.8582 | 0.3186 | 0.116* | |
H41B | −0.0625 | 0.8761 | 0.3677 | 0.116* | |
C42 | −0.1624 (5) | 0.7683 (3) | 0.3881 (3) | 0.1092 (16) | |
H42A | −0.1703 | 0.8014 | 0.4484 | 0.131* | |
H42B | −0.2464 | 0.7380 | 0.3663 | 0.131* | |
C43 | −0.0232 (3) | 0.8174 (2) | 0.1939 (2) | 0.0599 (8) | |
H43A | 0.0653 | 0.7987 | 0.1768 | 0.072* | |
H43B | −0.0184 | 0.8808 | 0.2217 | 0.072* | |
C44 | −0.1139 (4) | 0.7998 (3) | 0.1120 (2) | 0.0772 (11) | |
H44 | −0.1135 | 0.7358 | 0.0837 | 0.093* | |
C45 | −0.0542 (5) | 0.8441 (3) | 0.0499 (3) | 0.1091 (15) | |
H45A | −0.1088 | 0.8311 | −0.0025 | 0.164* | |
H45B | 0.0333 | 0.8223 | 0.0367 | 0.164* | |
H45C | −0.0491 | 0.9071 | 0.0762 | 0.164* | |
C46 | −0.2533 (4) | 0.8234 (3) | 0.1279 (3) | 0.1177 (16) | |
H46A | −0.2581 | 0.8856 | 0.1570 | 0.177* | |
H46B | −0.2894 | 0.7902 | 0.1635 | 0.177* | |
H46C | −0.3034 | 0.8098 | 0.0737 | 0.177* | |
C51 | 0.1787 (4) | 0.6952 (3) | 0.3955 (2) | 0.0859 (12) | |
H51A | 0.2580 | 0.7322 | 0.4142 | 0.103* | |
H51B | 0.1907 | 0.6407 | 0.4111 | 0.103* | |
C52 | 0.0604 (5) | 0.7423 (3) | 0.4373 (2) | 0.1013 (15) | |
H52A | 0.0507 | 0.7333 | 0.4938 | 0.122* | |
H52B | 0.0696 | 0.8054 | 0.4446 | 0.122* | |
C53 | 0.2650 (3) | 0.6351 (2) | 0.2489 (2) | 0.0605 (8) | |
H53A | 0.2335 | 0.6145 | 0.1887 | 0.073* | |
H53B | 0.2924 | 0.5836 | 0.2662 | 0.073* | |
C54 | 0.3857 (4) | 0.6966 (2) | 0.2560 (2) | 0.0732 (10) | |
H54 | 0.4206 | 0.7135 | 0.3162 | 0.088* | |
C55 | 0.4924 (4) | 0.6446 (3) | 0.1989 (4) | 0.1183 (17) | |
H55A | 0.4651 | 0.6338 | 0.1389 | 0.177* | |
H55B | 0.5048 | 0.5891 | 0.2112 | 0.177* | |
H55C | 0.5743 | 0.6783 | 0.2106 | 0.177* | |
C56 | 0.3497 (4) | 0.7796 (3) | 0.2337 (3) | 0.0973 (13) | |
H56A | 0.4271 | 0.8173 | 0.2404 | 0.146* | |
H56B | 0.2835 | 0.8100 | 0.2716 | 0.146* | |
H56C | 0.3155 | 0.7647 | 0.1747 | 0.146* | |
C61 | −0.1721 (4) | 0.5683 (3) | 0.3062 (2) | 0.0801 (11) | |
H61A | −0.1743 | 0.5050 | 0.2991 | 0.096* | |
H61B | −0.2625 | 0.5884 | 0.3051 | 0.096* | |
C62 | −0.0976 (5) | 0.6183 (3) | 0.3917 (2) | 0.0916 (13) | |
H62A | −0.1551 | 0.6273 | 0.4402 | 0.110* | |
H62B | −0.0208 | 0.5858 | 0.4023 | 0.110* | |
C63 | −0.1421 (3) | 0.5396 (2) | 0.14950 (18) | 0.0564 (8) | |
H63A | −0.1010 | 0.5667 | 0.1098 | 0.068* | |
H63B | −0.2372 | 0.5460 | 0.1436 | 0.068* | |
C64 | −0.1124 (4) | 0.4416 (2) | 0.1222 (2) | 0.0792 (11) | |
H64 | −0.1614 | 0.4146 | 0.1597 | 0.095* | |
C65 | −0.1675 (5) | 0.4001 (3) | 0.0296 (3) | 0.1206 (18) | |
H65A | −0.2618 | 0.4071 | 0.0273 | 0.181* | |
H65B | −0.1480 | 0.3381 | 0.0116 | 0.181* | |
H65C | −0.1274 | 0.4288 | −0.0085 | 0.181* | |
C66 | 0.0313 (5) | 0.4249 (3) | 0.1354 (4) | 0.136 (2) | |
H66A | 0.0831 | 0.4526 | 0.1013 | 0.203* | |
H66B | 0.0456 | 0.3622 | 0.1178 | 0.203* | |
H66C | 0.0576 | 0.4491 | 0.1956 | 0.203* | |
Cl1 | 0.74844 (12) | 0.48539 (9) | 0.49895 (10) | 0.1183 (5) | |
Cl2 | 0.24967 (11) | 0.95105 (8) | 0.49482 (9) | 0.1136 (4) | |
O1 | 0.0445 (6) | 0.0588 (3) | 0.4090 (3) | 0.1250 (13) | |
H101 | −0.033 (6) | 0.050 (4) | 0.422 (4) | 0.14 (3)* | |
H102 | 0.086 (8) | 0.016 (6) | 0.430 (5) | 0.25 (4)* | |
O2 | 0.4520 (7) | 0.1069 (3) | 0.5950 (3) | 0.1382 (16) | |
H103 | 0.530 (7) | 0.088 (4) | 0.584 (4) | 0.16 (3)* | |
H104 | 0.403 (8) | 0.066 (6) | 0.570 (5) | 0.24 (5)* | |
O3 | −0.0019 (6) | 0.6098 (3) | 0.6065 (3) | 0.1294 (15) | |
H105 | 0.076 (5) | 0.593 (3) | 0.591 (3) | 0.098 (17)* | |
H106 | −0.072 (4) | 0.578 (3) | 0.588 (3) | 0.091 (17)* | |
O4 | 0.5064 (6) | 0.5514 (4) | 0.3944 (3) | 0.1389 (17) | |
H107 | 0.551 (6) | 0.506 (4) | 0.414 (4) | 0.16 (3)* | |
H108 | 0.448 (5) | 0.541 (3) | 0.415 (3) | 0.086 (18)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0493 (5) | 0.0529 (5) | 0.0378 (4) | 0.0011 (4) | 0.0066 (3) | 0.0077 (3) |
N1 | 0.0780 (19) | 0.0541 (16) | 0.0458 (13) | −0.0067 (14) | 0.0140 (13) | 0.0121 (12) |
N2 | 0.0663 (18) | 0.0635 (18) | 0.0593 (15) | 0.0197 (15) | 0.0190 (13) | 0.0157 (13) |
N3 | 0.0575 (18) | 0.091 (2) | 0.0497 (14) | −0.0071 (16) | −0.0033 (13) | 0.0116 (14) |
N4 | 0.081 (2) | 0.074 (2) | 0.0421 (13) | 0.0076 (17) | 0.0139 (13) | 0.0101 (13) |
C13 | 0.061 (2) | 0.0480 (18) | 0.0553 (17) | 0.0068 (15) | 0.0082 (14) | 0.0145 (14) |
C14 | 0.061 (2) | 0.059 (2) | 0.0570 (17) | −0.0051 (16) | 0.0069 (15) | 0.0158 (15) |
C15 | 0.080 (3) | 0.083 (3) | 0.098 (3) | −0.005 (2) | −0.020 (2) | 0.027 (2) |
C16 | 0.108 (3) | 0.065 (2) | 0.069 (2) | −0.006 (2) | 0.008 (2) | 0.0044 (18) |
C23 | 0.052 (2) | 0.057 (2) | 0.0640 (18) | 0.0018 (16) | −0.0011 (15) | 0.0186 (15) |
C24 | 0.071 (3) | 0.057 (2) | 0.091 (2) | 0.0041 (18) | 0.0058 (19) | 0.0276 (18) |
C25 | 0.077 (3) | 0.082 (3) | 0.156 (4) | −0.017 (2) | −0.006 (3) | 0.050 (3) |
C26 | 0.129 (4) | 0.093 (3) | 0.114 (3) | 0.005 (3) | 0.007 (3) | 0.061 (3) |
C33 | 0.059 (2) | 0.088 (3) | 0.082 (2) | −0.002 (2) | −0.0052 (19) | 0.016 (2) |
C34 | 0.081 (3) | 0.088 (3) | 0.102 (3) | 0.025 (2) | −0.013 (2) | 0.006 (2) |
C35 | 0.161 (5) | 0.079 (4) | 0.191 (6) | 0.024 (4) | −0.041 (4) | −0.001 (3) |
C36 | 0.060 (3) | 0.286 (9) | 0.191 (6) | 0.002 (4) | 0.037 (4) | 0.028 (6) |
C11A | 0.077 (6) | 0.070 (7) | 0.056 (7) | −0.012 (5) | 0.022 (5) | 0.033 (6) |
C12A | 0.102 (7) | 0.095 (6) | 0.055 (4) | 0.014 (5) | 0.030 (4) | 0.029 (4) |
C21A | 0.084 (7) | 0.052 (8) | 0.065 (6) | 0.019 (6) | 0.003 (4) | 0.006 (6) |
C22A | 0.083 (6) | 0.105 (7) | 0.065 (4) | 0.025 (5) | 0.034 (4) | 0.018 (4) |
C31A | 0.073 (8) | 0.127 (10) | 0.049 (6) | −0.049 (8) | 0.005 (5) | −0.006 (6) |
C32A | 0.134 (9) | 0.094 (6) | 0.042 (3) | −0.011 (6) | −0.004 (4) | −0.002 (4) |
C11B | 0.21 (2) | 0.084 (14) | 0.069 (13) | −0.002 (14) | 0.044 (13) | −0.011 (10) |
C12B | 0.096 (9) | 0.084 (8) | 0.079 (7) | −0.023 (7) | 0.051 (7) | 0.008 (6) |
C21B | 0.086 (10) | 0.055 (10) | 0.072 (9) | 0.006 (7) | 0.051 (8) | −0.012 (7) |
C22B | 0.079 (8) | 0.081 (7) | 0.057 (5) | 0.001 (6) | 0.026 (5) | −0.008 (4) |
C31B | 0.115 (16) | 0.165 (18) | 0.054 (11) | 0.067 (14) | −0.036 (10) | 0.008 (10) |
C32B | 0.106 (9) | 0.136 (12) | 0.042 (5) | 0.012 (9) | 0.014 (5) | 0.026 (6) |
P2 | 0.0527 (5) | 0.0490 (5) | 0.0377 (4) | −0.0003 (4) | 0.0066 (3) | 0.0127 (3) |
N5 | 0.0556 (17) | 0.0674 (17) | 0.0497 (13) | −0.0043 (14) | −0.0030 (12) | 0.0198 (12) |
N6 | 0.0673 (17) | 0.0603 (17) | 0.0448 (13) | −0.0160 (14) | 0.0048 (12) | 0.0103 (12) |
N7 | 0.083 (2) | 0.0593 (17) | 0.0530 (14) | 0.0176 (15) | 0.0152 (13) | 0.0167 (12) |
N8 | 0.075 (2) | 0.0684 (18) | 0.0432 (13) | −0.0108 (16) | 0.0101 (13) | 0.0100 (12) |
C41 | 0.129 (4) | 0.078 (3) | 0.082 (3) | 0.036 (3) | 0.041 (3) | 0.014 (2) |
C42 | 0.128 (4) | 0.128 (4) | 0.071 (2) | 0.042 (3) | 0.043 (2) | 0.021 (2) |
C43 | 0.059 (2) | 0.0486 (19) | 0.074 (2) | 0.0025 (16) | −0.0026 (16) | 0.0218 (16) |
C44 | 0.069 (3) | 0.084 (3) | 0.089 (2) | 0.006 (2) | −0.008 (2) | 0.045 (2) |
C45 | 0.122 (4) | 0.125 (4) | 0.102 (3) | 0.013 (3) | −0.004 (3) | 0.068 (3) |
C46 | 0.076 (3) | 0.136 (4) | 0.146 (4) | −0.001 (3) | −0.015 (3) | 0.052 (3) |
C51 | 0.086 (3) | 0.116 (3) | 0.058 (2) | −0.016 (3) | −0.011 (2) | 0.032 (2) |
C52 | 0.116 (4) | 0.131 (4) | 0.0467 (19) | −0.021 (3) | 0.002 (2) | 0.011 (2) |
C53 | 0.051 (2) | 0.056 (2) | 0.079 (2) | −0.0014 (16) | −0.0035 (16) | 0.0261 (16) |
C54 | 0.063 (2) | 0.070 (2) | 0.093 (2) | −0.0080 (19) | −0.0074 (19) | 0.034 (2) |
C55 | 0.060 (3) | 0.098 (3) | 0.195 (5) | 0.003 (3) | 0.030 (3) | 0.037 (3) |
C56 | 0.084 (3) | 0.078 (3) | 0.145 (4) | −0.015 (2) | −0.005 (3) | 0.059 (3) |
C61 | 0.089 (3) | 0.088 (3) | 0.0593 (19) | −0.028 (2) | 0.0184 (19) | 0.0147 (18) |
C62 | 0.125 (4) | 0.096 (3) | 0.058 (2) | −0.022 (3) | 0.023 (2) | 0.027 (2) |
C63 | 0.0521 (19) | 0.062 (2) | 0.0509 (16) | −0.0023 (16) | 0.0014 (14) | 0.0099 (14) |
C64 | 0.081 (3) | 0.060 (2) | 0.088 (2) | 0.001 (2) | 0.015 (2) | 0.0070 (19) |
C65 | 0.154 (5) | 0.092 (3) | 0.083 (3) | −0.022 (3) | 0.017 (3) | −0.027 (2) |
C66 | 0.094 (4) | 0.088 (4) | 0.215 (6) | 0.031 (3) | 0.023 (4) | 0.024 (3) |
Cl1 | 0.0861 (8) | 0.1121 (10) | 0.1764 (13) | 0.0095 (7) | 0.0333 (8) | 0.0692 (9) |
Cl2 | 0.0769 (8) | 0.1007 (9) | 0.1633 (12) | −0.0105 (6) | 0.0060 (7) | 0.0387 (8) |
O1 | 0.114 (3) | 0.133 (3) | 0.139 (3) | 0.003 (3) | 0.023 (3) | 0.055 (3) |
O2 | 0.125 (4) | 0.140 (4) | 0.121 (3) | 0.002 (3) | −0.002 (3) | −0.007 (2) |
O3 | 0.127 (4) | 0.128 (3) | 0.112 (3) | 0.022 (3) | 0.012 (3) | −0.001 (2) |
O4 | 0.136 (4) | 0.192 (5) | 0.109 (3) | 0.017 (3) | 0.030 (3) | 0.071 (3) |
P1—N3 | 1.658 (3) | C22B—H22D | 0.9700 |
P1—N2 | 1.664 (3) | C31B—C32B | 1.48 (3) |
P1—N1 | 1.669 (3) | C31B—H31C | 0.9700 |
P1—N4 | 1.973 (2) | C31B—H31D | 0.9700 |
P1—H1 | 1.1000 | C32B—H32C | 0.9700 |
N1—C11B | 1.45 (3) | C32B—H32D | 0.9700 |
N1—C13 | 1.459 (4) | P2—N7 | 1.657 (3) |
N1—C11A | 1.484 (12) | P2—N5 | 1.666 (3) |
N2—C21A | 1.400 (16) | P2—N6 | 1.669 (3) |
N2—C23 | 1.457 (4) | P2—N8 | 1.965 (2) |
N2—C21B | 1.577 (19) | P2—H2 | 1.1000 |
N3—C31A | 1.431 (15) | N5—C51 | 1.463 (4) |
N3—C33 | 1.466 (4) | N5—C53 | 1.470 (4) |
N3—C31B | 1.52 (2) | N6—C63 | 1.460 (3) |
N4—C32A | 1.424 (8) | N6—C61 | 1.465 (4) |
N4—C12B | 1.438 (10) | N7—C43 | 1.460 (4) |
N4—C12A | 1.502 (8) | N7—C41 | 1.470 (4) |
N4—C22B | 1.513 (10) | N8—C42 | 1.456 (5) |
N4—C22A | 1.519 (7) | N8—C52 | 1.483 (5) |
N4—C32B | 1.559 (12) | N8—C62 | 1.489 (5) |
C13—C14 | 1.519 (4) | C41—C42 | 1.528 (6) |
C13—H13A | 0.9700 | C41—H41A | 0.9700 |
C13—H13B | 0.9700 | C41—H41B | 0.9700 |
C14—C15 | 1.513 (5) | C42—H42A | 0.9700 |
C14—C16 | 1.528 (4) | C42—H42B | 0.9700 |
C14—H14 | 0.9800 | C43—C44 | 1.533 (4) |
C15—H15A | 0.9600 | C43—H43A | 0.9700 |
C15—H15B | 0.9600 | C43—H43B | 0.9700 |
C15—H15C | 0.9600 | C44—C46 | 1.473 (5) |
C16—H16A | 0.9600 | C44—C45 | 1.515 (5) |
C16—H16B | 0.9600 | C44—H44 | 0.9800 |
C16—H16C | 0.9600 | C45—H45A | 0.9600 |
C23—C24 | 1.524 (4) | C45—H45B | 0.9600 |
C23—H23A | 0.9700 | C45—H45C | 0.9600 |
C23—H23B | 0.9700 | C46—H46A | 0.9600 |
C24—C25 | 1.509 (5) | C46—H46B | 0.9600 |
C24—C26 | 1.523 (5) | C46—H46C | 0.9600 |
C24—H24 | 0.9800 | C51—C52 | 1.493 (6) |
C25—H25A | 0.9600 | C51—H51A | 0.9700 |
C25—H25B | 0.9600 | C51—H51B | 0.9700 |
C25—H25C | 0.9600 | C52—H52A | 0.9700 |
C26—H26A | 0.9600 | C52—H52B | 0.9700 |
C26—H26B | 0.9600 | C53—C54 | 1.530 (5) |
C26—H26C | 0.9600 | C53—H53A | 0.9700 |
C33—C34 | 1.508 (5) | C53—H53B | 0.9700 |
C33—H33A | 0.9700 | C54—C56 | 1.497 (5) |
C33—H33B | 0.9700 | C54—C55 | 1.530 (5) |
C34—C36 | 1.491 (7) | C54—H54 | 0.9800 |
C34—C35 | 1.521 (6) | C55—H55A | 0.9600 |
C34—H34 | 0.9800 | C55—H55B | 0.9600 |
C35—H35A | 0.9600 | C55—H55C | 0.9600 |
C35—H35B | 0.9600 | C56—H56A | 0.9600 |
C35—H35C | 0.9600 | C56—H56B | 0.9600 |
C36—H36A | 0.9600 | C56—H56C | 0.9600 |
C36—H36B | 0.9600 | C61—C62 | 1.538 (5) |
C36—H36C | 0.9600 | C61—H61A | 0.9700 |
C11A—C12A | 1.470 (18) | C61—H61B | 0.9700 |
C11A—H11A | 0.9700 | C62—H62A | 0.9700 |
C11A—H11B | 0.9700 | C62—H62B | 0.9700 |
C12A—H12A | 0.9700 | C63—C64 | 1.515 (4) |
C12A—H12B | 0.9700 | C63—H63A | 0.9700 |
C21A—C22A | 1.476 (17) | C63—H63B | 0.9700 |
C21A—H21A | 0.9700 | C64—C66 | 1.495 (6) |
C21A—H21B | 0.9700 | C64—C65 | 1.527 (5) |
C22A—H22A | 0.9700 | C64—H64 | 0.9800 |
C22A—H22B | 0.9700 | C65—H65A | 0.9600 |
C31A—C32A | 1.65 (2) | C65—H65B | 0.9600 |
C31A—H31A | 0.9700 | C65—H65C | 0.9600 |
C31A—H31B | 0.9700 | C66—H66A | 0.9600 |
C32A—H32A | 0.9700 | C66—H66B | 0.9600 |
C32A—H32B | 0.9700 | C66—H66C | 0.9600 |
C11B—C12B | 1.64 (3) | O1—H101 | 0.84 (6) |
C11B—H11C | 0.9700 | O1—H102 | 0.94 (9) |
C11B—H11D | 0.9700 | O2—H103 | 0.85 (7) |
C12B—H12C | 0.9700 | O2—H104 | 0.80 (8) |
C12B—H12D | 0.9700 | O3—H105 | 0.85 (4) |
C21B—C22B | 1.52 (3) | O3—H106 | 0.86 (4) |
C21B—H21C | 0.9700 | O4—H107 | 0.97 (6) |
C21B—H21D | 0.9700 | O4—H108 | 0.73 (4) |
C22B—H22C | 0.9700 | ||
N3—P1—N2 | 120.17 (15) | C22B—C21B—H21C | 110.8 |
N3—P1—N1 | 120.09 (15) | N2—C21B—H21C | 110.8 |
N2—P1—N1 | 118.53 (15) | C22B—C21B—H21D | 110.8 |
N3—P1—N4 | 86.27 (13) | N2—C21B—H21D | 110.8 |
N2—P1—N4 | 86.52 (12) | H21C—C21B—H21D | 108.9 |
N1—P1—N4 | 86.24 (12) | N4—C22B—C21B | 107.5 (9) |
N3—P1—H1 | 92.9 | N4—C22B—H22C | 110.2 |
N2—P1—H1 | 93.9 | C21B—C22B—H22C | 110.2 |
N1—P1—H1 | 94.2 | N4—C22B—H22D | 110.2 |
N4—P1—H1 | 179.2 | C21B—C22B—H22D | 110.2 |
C11B—N1—C13 | 112.8 (11) | H22C—C22B—H22D | 108.5 |
C13—N1—C11A | 116.6 (7) | C32B—C31B—N3 | 105.9 (16) |
C11B—N1—P1 | 123.3 (11) | C32B—C31B—H31C | 110.6 |
C13—N1—P1 | 123.0 (2) | N3—C31B—H31C | 110.6 |
C11A—N1—P1 | 119.5 (7) | C32B—C31B—H31D | 110.6 |
C21A—N2—C23 | 115.4 (6) | N3—C31B—H31D | 110.6 |
C23—N2—C21B | 115.1 (9) | H31C—C31B—H31D | 108.7 |
C21A—N2—P1 | 120.0 (6) | C31B—C32B—N4 | 99.7 (10) |
C23—N2—P1 | 124.0 (2) | C31B—C32B—H32C | 111.8 |
C21B—N2—P1 | 120.2 (9) | N4—C32B—H32C | 111.8 |
C31A—N3—C33 | 113.3 (6) | C31B—C32B—H32D | 111.8 |
C33—N3—C31B | 117.4 (11) | N4—C32B—H32D | 111.8 |
C31A—N3—P1 | 123.0 (6) | H32C—C32B—H32D | 109.6 |
C33—N3—P1 | 123.4 (2) | N7—P2—N5 | 120.29 (14) |
C31B—N3—P1 | 117.9 (10) | N7—P2—N6 | 118.48 (15) |
C32A—N4—C12B | 139.9 (6) | N5—P2—N6 | 120.12 (14) |
C32A—N4—C12A | 112.5 (6) | N7—P2—N8 | 86.81 (12) |
C12B—N4—C22B | 117.2 (7) | N5—P2—N8 | 86.24 (12) |
C12A—N4—C22B | 147.4 (5) | N6—P2—N8 | 86.40 (11) |
C32A—N4—C22A | 113.5 (5) | N7—P2—H2 | 93.6 |
C12A—N4—C22A | 111.7 (5) | N5—P2—H2 | 92.9 |
C12B—N4—C32B | 107.8 (8) | N6—P2—H2 | 94.1 |
C22B—N4—C32B | 109.4 (7) | N8—P2—H2 | 179.1 |
C22A—N4—C32B | 147.8 (5) | C51—N5—C53 | 115.2 (3) |
C32A—N4—P1 | 107.7 (4) | C51—N5—P2 | 120.7 (2) |
C12B—N4—P1 | 109.9 (4) | C53—N5—P2 | 122.48 (19) |
C12A—N4—P1 | 105.6 (3) | C63—N6—C61 | 115.0 (3) |
C22B—N4—P1 | 106.3 (4) | C63—N6—P2 | 122.5 (2) |
C22A—N4—P1 | 105.3 (3) | C61—N6—P2 | 120.7 (2) |
C32B—N4—P1 | 105.7 (4) | C43—N7—C41 | 116.0 (3) |
N1—C13—C14 | 114.8 (3) | C43—N7—P2 | 120.5 (2) |
N1—C13—H13A | 108.6 | C41—N7—P2 | 120.2 (2) |
C14—C13—H13A | 108.6 | C42—N8—C52 | 111.8 (3) |
N1—C13—H13B | 108.6 | C42—N8—C62 | 114.4 (3) |
C14—C13—H13B | 108.6 | C52—N8—C62 | 109.9 (3) |
H13A—C13—H13B | 107.5 | C42—N8—P2 | 107.1 (2) |
C15—C14—C13 | 112.1 (3) | C52—N8—P2 | 106.9 (2) |
C15—C14—C16 | 110.9 (3) | C62—N8—P2 | 106.33 (19) |
C13—C14—C16 | 109.5 (3) | N7—C41—C42 | 105.4 (3) |
C15—C14—H14 | 108.1 | N7—C41—H41A | 110.7 |
C13—C14—H14 | 108.1 | C42—C41—H41A | 110.7 |
C16—C14—H14 | 108.1 | N7—C41—H41B | 110.7 |
C14—C15—H15A | 109.5 | C42—C41—H41B | 110.7 |
C14—C15—H15B | 109.5 | H41A—C41—H41B | 108.8 |
H15A—C15—H15B | 109.5 | N8—C42—C41 | 106.4 (3) |
C14—C15—H15C | 109.5 | N8—C42—H42A | 110.5 |
H15A—C15—H15C | 109.5 | C41—C42—H42A | 110.5 |
H15B—C15—H15C | 109.5 | N8—C42—H42B | 110.5 |
C14—C16—H16A | 109.5 | C41—C42—H42B | 110.5 |
C14—C16—H16B | 109.5 | H42A—C42—H42B | 108.6 |
H16A—C16—H16B | 109.5 | N7—C43—C44 | 115.5 (3) |
C14—C16—H16C | 109.5 | N7—C43—H43A | 108.4 |
H16A—C16—H16C | 109.5 | C44—C43—H43A | 108.4 |
H16B—C16—H16C | 109.5 | N7—C43—H43B | 108.4 |
N2—C23—C24 | 115.5 (3) | C44—C43—H43B | 108.4 |
N2—C23—H23A | 108.4 | H43A—C43—H43B | 107.5 |
C24—C23—H23A | 108.4 | C46—C44—C45 | 112.2 (3) |
N2—C23—H23B | 108.4 | C46—C44—C43 | 114.7 (3) |
C24—C23—H23B | 108.4 | C45—C44—C43 | 109.3 (3) |
H23A—C23—H23B | 107.5 | C46—C44—H44 | 106.7 |
C25—C24—C26 | 111.6 (4) | C45—C44—H44 | 106.7 |
C25—C24—C23 | 111.4 (3) | C43—C44—H44 | 106.7 |
C26—C24—C23 | 109.0 (3) | C44—C45—H45A | 109.5 |
C25—C24—H24 | 108.3 | C44—C45—H45B | 109.5 |
C26—C24—H24 | 108.3 | H45A—C45—H45B | 109.5 |
C23—C24—H24 | 108.3 | C44—C45—H45C | 109.5 |
C24—C25—H25A | 109.5 | H45A—C45—H45C | 109.5 |
C24—C25—H25B | 109.5 | H45B—C45—H45C | 109.5 |
H25A—C25—H25B | 109.5 | C44—C46—H46A | 109.5 |
C24—C25—H25C | 109.5 | C44—C46—H46B | 109.5 |
H25A—C25—H25C | 109.5 | H46A—C46—H46B | 109.5 |
H25B—C25—H25C | 109.5 | C44—C46—H46C | 109.5 |
C24—C26—H26A | 109.5 | H46A—C46—H46C | 109.5 |
C24—C26—H26B | 109.5 | H46B—C46—H46C | 109.5 |
H26A—C26—H26B | 109.5 | N5—C51—C52 | 106.9 (3) |
C24—C26—H26C | 109.5 | N5—C51—H51A | 110.3 |
H26A—C26—H26C | 109.5 | C52—C51—H51A | 110.3 |
H26B—C26—H26C | 109.5 | N5—C51—H51B | 110.3 |
N3—C33—C34 | 115.9 (4) | C52—C51—H51B | 110.3 |
N3—C33—H33A | 108.3 | H51A—C51—H51B | 108.6 |
C34—C33—H33A | 108.3 | N8—C52—C51 | 106.9 (3) |
N3—C33—H33B | 108.3 | N8—C52—H52A | 110.3 |
C34—C33—H33B | 108.3 | C51—C52—H52A | 110.3 |
H33A—C33—H33B | 107.4 | N8—C52—H52B | 110.3 |
C36—C34—C33 | 112.4 (5) | C51—C52—H52B | 110.3 |
C36—C34—C35 | 110.1 (5) | H52A—C52—H52B | 108.6 |
C33—C34—C35 | 109.1 (4) | N5—C53—C54 | 114.4 (3) |
C36—C34—H34 | 108.4 | N5—C53—H53A | 108.7 |
C33—C34—H34 | 108.4 | C54—C53—H53A | 108.7 |
C35—C34—H34 | 108.4 | N5—C53—H53B | 108.7 |
C34—C35—H35A | 109.5 | C54—C53—H53B | 108.7 |
C34—C35—H35B | 109.5 | H53A—C53—H53B | 107.6 |
H35A—C35—H35B | 109.5 | C56—C54—C53 | 111.7 (3) |
C34—C35—H35C | 109.5 | C56—C54—C55 | 112.7 (4) |
H35A—C35—H35C | 109.5 | C53—C54—C55 | 108.3 (3) |
H35B—C35—H35C | 109.5 | C56—C54—H54 | 108.0 |
C34—C36—H36A | 109.5 | C53—C54—H54 | 108.0 |
C34—C36—H36B | 109.5 | C55—C54—H54 | 108.0 |
H36A—C36—H36B | 109.5 | C54—C55—H55A | 109.5 |
C34—C36—H36C | 109.5 | C54—C55—H55B | 109.5 |
H36A—C36—H36C | 109.5 | H55A—C55—H55B | 109.5 |
H36B—C36—H36C | 109.5 | C54—C55—H55C | 109.5 |
C12A—C11A—N1 | 106.2 (9) | H55A—C55—H55C | 109.5 |
C12A—C11A—H11A | 110.5 | H55B—C55—H55C | 109.5 |
N1—C11A—H11A | 110.5 | C54—C56—H56A | 109.5 |
C12A—C11A—H11B | 110.5 | C54—C56—H56B | 109.5 |
N1—C11A—H11B | 110.5 | H56A—C56—H56B | 109.5 |
H11A—C11A—H11B | 108.7 | C54—C56—H56C | 109.5 |
C11A—C12A—N4 | 105.6 (7) | H56A—C56—H56C | 109.5 |
C11A—C12A—H12A | 110.6 | H56B—C56—H56C | 109.5 |
N4—C12A—H12A | 110.6 | N6—C61—C62 | 105.4 (3) |
C11A—C12A—H12B | 110.6 | N6—C61—H61A | 110.7 |
N4—C12A—H12B | 110.6 | C62—C61—H61A | 110.7 |
H12A—C12A—H12B | 108.7 | N6—C61—H61B | 110.7 |
N2—C21A—C22A | 111.0 (9) | C62—C61—H61B | 110.7 |
N2—C21A—H21A | 109.4 | H61A—C61—H61B | 108.8 |
C22A—C21A—H21A | 109.4 | N8—C62—C61 | 104.7 (3) |
N2—C21A—H21B | 109.4 | N8—C62—H62A | 110.8 |
C22A—C21A—H21B | 109.4 | C61—C62—H62A | 110.8 |
H21A—C21A—H21B | 108.0 | N8—C62—H62B | 110.8 |
C21A—C22A—N4 | 104.9 (8) | C61—C62—H62B | 110.8 |
C21A—C22A—H22A | 110.8 | H62A—C62—H62B | 108.9 |
N4—C22A—H22A | 110.8 | N6—C63—C64 | 115.6 (3) |
C21A—C22A—H22B | 110.8 | N6—C63—H63A | 108.4 |
N4—C22A—H22B | 110.8 | C64—C63—H63A | 108.4 |
H22A—C22A—H22B | 108.8 | N6—C63—H63B | 108.4 |
N3—C31A—C32A | 101.6 (9) | C64—C63—H63B | 108.4 |
N3—C31A—H31A | 111.4 | H63A—C63—H63B | 107.5 |
C32A—C31A—H31A | 111.4 | C66—C64—C63 | 112.3 (3) |
N3—C31A—H31B | 111.4 | C66—C64—C65 | 114.0 (4) |
C32A—C31A—H31B | 111.4 | C63—C64—C65 | 109.1 (3) |
H31A—C31A—H31B | 109.3 | C66—C64—H64 | 107.1 |
N4—C32A—C31A | 104.6 (7) | C63—C64—H64 | 107.1 |
N4—C32A—H32A | 110.8 | C65—C64—H64 | 107.1 |
C31A—C32A—H32A | 110.8 | C64—C65—H65A | 109.5 |
N4—C32A—H32B | 110.8 | C64—C65—H65B | 109.5 |
C31A—C32A—H32B | 110.8 | H65A—C65—H65B | 109.5 |
H32A—C32A—H32B | 108.9 | C64—C65—H65C | 109.5 |
N1—C11B—C12B | 104.1 (18) | H65A—C65—H65C | 109.5 |
N1—C11B—H11C | 110.9 | H65B—C65—H65C | 109.5 |
C12B—C11B—H11C | 110.9 | C64—C66—H66A | 109.5 |
N1—C11B—H11D | 110.9 | C64—C66—H66B | 109.5 |
C12B—C11B—H11D | 110.9 | H66A—C66—H66B | 109.5 |
H11C—C11B—H11D | 109.0 | C64—C66—H66C | 109.5 |
N4—C12B—C11B | 105.4 (12) | H66A—C66—H66C | 109.5 |
N4—C12B—H12C | 110.7 | H66B—C66—H66C | 109.5 |
C11B—C12B—H12C | 110.7 | H101—O1—H102 | 98 (6) |
N4—C12B—H12D | 110.7 | H103—O2—H104 | 105 (7) |
C11B—C12B—H12D | 110.7 | H105—O3—H106 | 123 (5) |
H12C—C12B—H12D | 108.8 | H107—O4—H108 | 86 (5) |
C22B—C21B—N2 | 104.7 (14) |
D—H···A | D—H | H···A | D···A | 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. |
Experimental details
Crystal data | |
Chemical formula | C18H40N4P+·Cl−·2H2O |
Mr | 414.99 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 2453.6 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.20 × 0.15 × 0.14 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.954, 0.967 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 35181, 9856, 5364 |
Rint | 0.063 |
(sin θ/λ)max (Å−1) | 0.631 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.212, 1.01 |
No. of reflections | 9856 |
No. of parameters | 568 |
No. of restraints | 18 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.39, −0.31 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | 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. |
Acknowledgements
This work was supported by a research grant from Chungbuk Nation University in 2012.
References
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kingston, J. V. & Verkade, J. G. (2005). Inorg. Chem. Commun. 8, 643–646. Web of Science CSD CrossRef CAS Google Scholar
Kisanga, P. B. & Verkade, J. G. (2001). Tetrahedron, 57, 467–475. Web of Science CrossRef CAS Google Scholar
Liu, X., Bai, Y. & Verkade, J. G. (1999). J. Organomet. Chem. 582, 16–24. Web of Science CSD CrossRef CAS Google Scholar
Liu, X., Ilankumaran, P., Guzei, I. A. & Verkade, J. G. (2000). J. Org. Chem. 65, 701–706. Web of Science CSD CrossRef CAS Google Scholar
Mohan, T., Arumugam, S., Wang, T., Jacobson, R. A. & Verkade, J. G. (1996). Heteroatom Chem. 7, 455–460. CSD CrossRef CAS Web of Science Google Scholar
Raders, M. R. & Verkade, J. G. (2010). J. Org. Chem. 75, 5308–5311. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, J.-S., Dopke, J. & Verkade, J. G. (1993). J. Am. Chem. Soc. 115, 5015–5020. CSD CrossRef CAS Web of Science Google Scholar
Thirupathi, N., Liu, X. & Verkade, J. G. (2003). Inorg. Chem. 42, 389–397. Web of Science CSD CrossRef PubMed CAS Google Scholar
Verkade, J. G. & Kisanga, P. (2003). Tetrahedron, 59, 7819–7858. Web of Science CrossRef CAS Google Scholar
Wroblewski, A., Pinkas, J. & Verkade, J. G. (1995). Main Group Chem. 1, 69–79. CAS Google Scholar
Zhou, Y., Armstrong, D. W., Zhang, Y. & Verkade, J. G. (2011). Tetrahedron Lett. 52, 1545–1548. Web of Science CrossRef CAS Google Scholar
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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).