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

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ISSN: 2056-9890

Bis[N-(2-hy­dr­oxy­benz­yl)adamantan-1-aminium] fluoride tetra­fluoro­borate monohydrate

aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: wangyc33@yahoo.com.cn

(Received 30 December 2011; accepted 7 January 2012; online 14 January 2012)

In the title compound, 2C17H24NO+·BF4·F·H2O, the asymmetric unit contains two N-(2-hy­droxy­benz­yl)adamantan-1-aminium cations, one BF4 anion, one F anion and one water mol­ecule. Both amine N atoms are protonated. The hy­droxy O atoms, amino N atoms and water O atom are involved in inter­molecular O—H⋯O, O—H⋯F, N—H⋯O and N—H⋯F hydrogen bonding.

Related literature

For the structures of related amino compounds, see: Fu et al. (2007[Fu, D.-W., Song, Y.-M., Wang, G.-X., Ye, Q., Xiong, R.-G., Akutagawa, T., Nakamura, T., Chan, P. W. H. & Huang, S. P. D. (2007). J. Am. Chem. Soc. 129, 5346-5347.], 2008[Fu, D.-W., Zhang, W. & Xiong, R.-G. (2008). Cryst. Growth Des. 8, 3461-3464.], 2009[Fu, D.-W., Ge, J.-Z., Dai, J., Ye, H.-Y. & Qu, Z.-R. (2009). Inorg. Chem. Commun. 12, 994-997.]); Fu & Xiong (2008[Fu, D.-W. & Xiong, R.-G. (2008). Dalton Trans. pp. 3946-3948.]). For the ferroelectric properties of related amino derivatives, see: Fu et al. (2011a[Fu, D.-W., Zhang, W., Cai, H.-L., Ge, J.-Z., Zhang, Y. & Xiong, R.-G. (2011a). Adv. Mater. 23, 5658-5662.],b[Fu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z., Xiong, R.-G. & Huang, S. P. D. (2011b). J. Am. Chem. Soc. 133, 12780-12786.],c[Fu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z., Xiong, R.-G., Huang, S. P. D. & Nakamura, T. (2011c). Angew. Chem. Int. Ed. 50, 11947-11951.]).

[Scheme 1]

Experimental

Crystal data
  • 2C17H24NO+·BF4·F·H2O

  • Mr = 640.57

  • Triclinic, [P \overline 1]

  • a = 9.4546 (19) Å

  • b = 12.532 (3) Å

  • c = 15.394 (3) Å

  • α = 104.28 (3)°

  • β = 103.20 (3)°

  • γ = 94.54 (3)°

  • V = 1703.1 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.10 × 0.05 × 0.05 mm

Data collection
  • Rigaku Mercury2 diffractometer

  • 14663 measured reflections

  • 5987 independent reflections

  • 2943 reflections with I > 2σ(I)

  • Rint = 0.078

Refinement
  • R[F2 > 2σ(F2)] = 0.074

  • wR(F2) = 0.221

  • S = 1.01

  • 5987 reflections

  • 406 parameters

  • 6 restraints

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1B⋯F3 0.90 2.26 3.125 (4) 161
N1—H1B⋯F4 0.90 2.26 2.992 (4) 138
N1—H1C⋯F5 0.90 1.74 2.607 (3) 161
N2—H2B⋯O2 0.90 2.13 2.791 (3) 129
N2—H2B⋯F3i 0.90 2.52 3.251 (3) 139
N2—H2D⋯F5i 0.90 1.70 2.600 (3) 175
O1—H1A⋯F5ii 0.82 1.67 2.487 (3) 172
O2—H2A⋯O3Wi 0.82 1.85 2.660 (4) 168
O3W—H3B⋯F2iii 0.82 1.97 2.733 (6) 155
O3W—H3C⋯F1 0.82 2.03 2.842 (6) 169
Symmetry codes: (i) x, y+1, z; (ii) -x, -y, -z; (iii) -x+1, -y, -z+1.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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

Organic amino compounds attracted more attention as phase transition dielectric materials for its application in memory storage (Fu et al. 2007; Fu & Xiong 2008; Fu et al. 2008; Fu et al. 2009). With the purpose of obtaining phase transition crystals of amino compounds, various amines have been studied and we have elaborated a series of new materials with this organic molecules (Fu et al. 2011a; Fu et al. 2011b; Fu et al. 2011c). In this study, we describe the crystal structure of the title compound, bis-N-(2-Hydroxybenzyl)adamantan-1-aminium tetrafluoroborate monofluoride monohydrate.

The asymmetric unit is composed of two N-(2-Hydroxybenzyl)adamantan-1-aminium cations, one BF4 anion, one F- anion and one water molecule. The two benzene rings are nearly coplanar and only twisted from each other by a dihedral angle of 4.48 (2)°. Both the amine N atoms were protonated. And the BF4 and F- groups were deprotonated to keep the charge balance. The geometric parameters of the title compound are in the normal range.

In the crystal structure, all the hydroxy O atoms, amino N atoms and aqueous O atom are involved in intermolecular O—H···O, O—H···F, N—H···O and N—H···F H-bonding interactions with the O atoms (O2 and O3W) and F atoms (F1 to F5). These hydrogen bonds link the molecules and ion units into a 1D chain parallel to the ac-plane(Table 1 and Fig.2).

Related literature top

For the structures of related amino compounds, see: Fu et al. (2007, 2008, 2009); Fu & Xiong (2008). For the ferroelectric properties of related amino derivatives, see: Fu et al. (2011a,b,c).

Experimental top

A mixture of N-(2-Hydroxybenzyl)adamantan-1-amine (4.0 mmol), HBF4 (2.0 mL), HF (2.0 mL) and 20 mL ethanol were added into a 50ml flask and refluxed for 5 hours, then cooled and filtrated. The solution was evaporated slowly in the air. Colorless block crystals suitable for X-ray analysis were obtained after one week.

Refinement top

All H atoms attached to C atoms were fixed geometrically and treated as riding with C-H = 0.93 Å (aromatic), C-H = 0.97 Å (methylene) and C-H = 0.98 Å (methine) with Uiso(H) = 1.2Ueq(C). H atoms bonded to N and O atoms were located in difference Fourier maps and restrained with the H–N = 0.90 (2)Å and H—O = 0.82 (2)Å. In the last stage of refinement they were treated as riding on the N and O atoms with Uiso(H) = 1.2Ueq(N) and Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms (except the H atoms bonding to N and O atoms) have been omitted for clarity.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed along the b axis showing the hydrogen bondings unit (dashed line). H atoms not involved in hydrogen bonding (dashed line) have been omitted for clarity.
Bis[N-(2-hydroxybenzyl)adamantan-1-aminium] fluoride tetrafluoroborate monohydrate top
Crystal data top
2C17H24NO+·BF4·F·H2OZ = 2
Mr = 640.57F(000) = 684
Triclinic, P1Dx = 1.249 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4546 (19) ÅCell parameters from 5987 reflections
b = 12.532 (3) Åθ = 3.0–27.5°
c = 15.394 (3) ŵ = 0.10 mm1
α = 104.28 (3)°T = 293 K
β = 103.20 (3)°Block, colorless
γ = 94.54 (3)°0.10 × 0.05 × 0.05 mm
V = 1703.1 (6) Å3
Data collection top
Rigaku Mercury2
diffractometer
2943 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.078
Graphite monochromatorθmax = 25.0°, θmin = 3.0°
Detector resolution: 13.6612 pixels mm-1h = 1111
CCD profile fitting scansk = 1414
14663 measured reflectionsl = 1818
5987 independent reflections
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)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0941P)2]
where P = (Fo2 + 2Fc2)/3
5987 reflections(Δ/σ)max < 0.001
406 parametersΔρmax = 0.34 e Å3
6 restraintsΔρmin = 0.36 e Å3
Crystal data top
2C17H24NO+·BF4·F·H2Oγ = 94.54 (3)°
Mr = 640.57V = 1703.1 (6) Å3
Triclinic, P1Z = 2
a = 9.4546 (19) ÅMo Kα radiation
b = 12.532 (3) ŵ = 0.10 mm1
c = 15.394 (3) ÅT = 293 K
α = 104.28 (3)°0.10 × 0.05 × 0.05 mm
β = 103.20 (3)°
Data collection top
Rigaku Mercury2
diffractometer
2943 reflections with I > 2σ(I)
14663 measured reflectionsRint = 0.078
5987 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0746 restraints
wR(F2) = 0.221H-atom parameters constrained
S = 1.01Δρmax = 0.34 e Å3
5987 reflectionsΔρmin = 0.36 e Å3
406 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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*/Ueq
O20.2166 (3)1.1728 (2)0.47603 (16)0.0768 (7)
H2A0.30131.19600.50690.115*
N20.0613 (2)1.02915 (18)0.30531 (17)0.0457 (6)
H2B0.15001.04810.34630.055*
H2D0.07191.04340.25250.055*
C10.0278 (4)1.2233 (3)0.3748 (2)0.0559 (9)
C20.0385 (4)1.3028 (3)0.3406 (3)0.0823 (12)
H2C0.12561.28200.29400.099*
C30.0221 (6)1.4134 (4)0.3743 (4)0.1035 (16)
H3A0.02521.46690.35150.124*
C40.1489 (7)1.4435 (4)0.4398 (4)0.0999 (16)
H4A0.18941.51820.46170.120*
C50.2210 (5)1.3663 (4)0.4756 (3)0.0836 (13)
H5A0.30991.38780.52060.100*
C60.1572 (4)1.2556 (3)0.4427 (3)0.0623 (9)
C70.0398 (4)1.1038 (3)0.3424 (3)0.0611 (9)
H7A0.12961.09520.29420.073*
H7B0.06531.08170.39360.073*
C80.0186 (3)0.9063 (2)0.2855 (2)0.0442 (7)
C90.1294 (4)0.8504 (3)0.2392 (3)0.0616 (9)
H9A0.22740.87470.28000.074*
H9B0.12730.87130.18230.074*
C100.1343 (3)0.8703 (3)0.2206 (2)0.0597 (9)
H10A0.13800.89150.16370.072*
H10B0.20560.90600.24960.072*
C110.0925 (4)0.7243 (3)0.2173 (3)0.0713 (11)
H11A0.16390.68810.18750.086*
C120.0605 (5)0.6881 (3)0.1526 (3)0.0790 (12)
H12A0.06370.70900.09570.095*
H12B0.08480.60790.13710.095*
C130.1698 (4)0.7428 (3)0.1991 (3)0.0727 (11)
H13A0.26850.71810.15750.087*
C140.0981 (4)0.6935 (3)0.3076 (3)0.0766 (11)
H14A0.07640.61340.29500.092*
H14B0.19600.71740.34870.092*
C150.1649 (4)0.7114 (3)0.2891 (3)0.0807 (12)
H15A0.19090.63160.27590.097*
H15B0.23530.74750.31880.097*
C160.0107 (4)0.7479 (3)0.3536 (3)0.0708 (11)
H16A0.00720.72680.41120.085*
C170.0250 (4)0.8748 (3)0.3757 (2)0.0614 (9)
H17A0.04540.91020.40590.074*
H17B0.12220.89990.41740.074*
O10.1598 (2)0.01917 (18)0.04354 (16)0.0671 (7)
H1A0.07960.04550.07990.101*
N10.3591 (3)0.12722 (18)0.15517 (16)0.0458 (6)
H1B0.39730.12080.21250.055*
H1C0.26260.10270.14280.055*
C180.3497 (3)0.0654 (2)0.0606 (2)0.0474 (8)
C190.2181 (4)0.0990 (2)0.0076 (2)0.0493 (8)
C200.1529 (4)0.2079 (3)0.0355 (2)0.0622 (9)
H20A0.06520.23000.08160.075*
C210.2177 (5)0.2837 (3)0.0049 (3)0.0766 (12)
H21A0.17260.35730.01350.092*
C220.3476 (5)0.2532 (3)0.0719 (3)0.0759 (12)
H22A0.39120.30540.09860.091*
C230.4205 (3)0.0525 (2)0.0859 (2)0.0514 (8)
H23A0.40630.07820.03040.062*
H23B0.52520.05650.11120.062*
C240.3909 (3)0.2505 (2)0.1669 (2)0.0470 (8)
C250.4134 (4)0.1434 (3)0.0993 (2)0.0592 (9)
H25A0.50190.12210.14470.071*
C260.5540 (4)0.2863 (3)0.1827 (3)0.0670 (10)
H26A0.58660.24860.12930.080*
H26B0.60870.26680.23660.080*
C270.5349 (6)0.4692 (3)0.2807 (3)0.1109 (17)
H27A0.55490.54910.29110.133*
H27B0.59020.45040.33490.133*
C280.5812 (4)0.4116 (3)0.1977 (3)0.0825 (12)
H28A0.68630.43510.20730.099*
C290.4980 (5)0.4424 (3)0.1150 (3)0.0837 (13)
H29A0.53070.40690.06100.100*
H29B0.51650.52230.12500.100*
C300.2869 (6)0.4637 (3)0.1814 (5)0.124 (2)
H30A0.18280.44060.17160.149*
H30B0.30280.54360.19060.149*
C310.3359 (5)0.4061 (3)0.0979 (3)0.0877 (13)
H31A0.28210.42620.04320.105*
C320.3073 (4)0.2796 (3)0.0817 (3)0.0702 (11)
H32A0.20310.25540.07020.084*
H32B0.33930.24230.02800.084*
C330.3429 (5)0.3085 (3)0.2515 (3)0.0847 (13)
H33A0.39650.28850.30550.102*
H33B0.23890.28560.24250.102*
C340.3730 (7)0.4347 (3)0.2667 (4)0.114 (2)
H34A0.34220.47320.32140.136*
F10.6340 (4)0.1272 (5)0.4430 (3)0.258 (3)
F20.5834 (7)0.0399 (5)0.3596 (4)0.286 (4)
F30.4169 (3)0.0710 (3)0.3459 (2)0.1287 (10)
F40.6105 (3)0.0848 (3)0.2942 (2)0.1330 (11)
B10.5602 (7)0.0654 (7)0.3648 (5)0.112 (2)
O3W0.4910 (3)0.2203 (3)0.5815 (2)0.1357 (13)
H3C0.54210.19970.54580.204*
H3B0.47980.18020.61500.204*
F50.08538 (18)0.08174 (14)0.15565 (12)0.0593 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0752 (17)0.0827 (18)0.0604 (16)0.0041 (14)0.0026 (13)0.0132 (14)
N20.0396 (14)0.0525 (16)0.0467 (16)0.0023 (12)0.0168 (12)0.0129 (13)
C10.061 (2)0.051 (2)0.062 (2)0.0100 (18)0.0286 (19)0.0148 (18)
C20.076 (3)0.064 (3)0.115 (4)0.021 (2)0.036 (3)0.027 (3)
C30.121 (4)0.070 (3)0.144 (5)0.026 (3)0.061 (4)0.043 (3)
C40.130 (5)0.054 (3)0.125 (5)0.001 (3)0.070 (4)0.009 (3)
C50.100 (3)0.070 (3)0.065 (3)0.015 (3)0.030 (2)0.011 (2)
C60.074 (3)0.061 (2)0.053 (2)0.010 (2)0.027 (2)0.008 (2)
C70.050 (2)0.060 (2)0.077 (2)0.0087 (17)0.0245 (18)0.0161 (19)
C80.0399 (17)0.0446 (18)0.0499 (19)0.0008 (14)0.0158 (15)0.0139 (15)
C90.064 (2)0.059 (2)0.077 (3)0.0148 (17)0.036 (2)0.0271 (19)
C100.049 (2)0.057 (2)0.065 (2)0.0002 (16)0.0062 (17)0.0116 (18)
C110.088 (3)0.056 (2)0.089 (3)0.021 (2)0.051 (3)0.025 (2)
C120.113 (4)0.051 (2)0.067 (3)0.000 (2)0.025 (3)0.008 (2)
C130.059 (2)0.063 (2)0.079 (3)0.0082 (18)0.004 (2)0.007 (2)
C140.084 (3)0.062 (2)0.098 (3)0.017 (2)0.033 (2)0.037 (2)
C150.085 (3)0.058 (2)0.111 (4)0.003 (2)0.051 (3)0.025 (2)
C160.089 (3)0.071 (2)0.070 (3)0.008 (2)0.033 (2)0.039 (2)
C170.068 (2)0.068 (2)0.051 (2)0.0004 (18)0.0171 (18)0.0224 (18)
O10.0626 (15)0.0603 (14)0.0734 (17)0.0008 (12)0.0021 (13)0.0258 (13)
N10.0434 (14)0.0490 (15)0.0448 (15)0.0015 (12)0.0140 (12)0.0112 (12)
C180.051 (2)0.0438 (18)0.053 (2)0.0091 (15)0.0253 (17)0.0122 (16)
C190.056 (2)0.0450 (19)0.050 (2)0.0055 (16)0.0205 (17)0.0141 (17)
C200.063 (2)0.054 (2)0.066 (2)0.0025 (18)0.0250 (19)0.0059 (19)
C210.098 (3)0.045 (2)0.100 (3)0.009 (2)0.059 (3)0.014 (2)
C220.092 (3)0.063 (3)0.098 (3)0.034 (2)0.050 (3)0.039 (2)
C230.0465 (19)0.0520 (19)0.059 (2)0.0082 (15)0.0235 (17)0.0115 (17)
C240.0460 (18)0.0439 (18)0.050 (2)0.0024 (14)0.0181 (15)0.0067 (15)
C250.061 (2)0.055 (2)0.071 (2)0.0196 (18)0.0279 (19)0.0212 (19)
C260.050 (2)0.062 (2)0.084 (3)0.0023 (17)0.0122 (19)0.018 (2)
C270.151 (5)0.062 (3)0.100 (4)0.032 (3)0.039 (4)0.006 (3)
C280.069 (3)0.058 (2)0.110 (4)0.0161 (19)0.026 (3)0.009 (3)
C290.110 (4)0.049 (2)0.110 (4)0.010 (2)0.059 (3)0.026 (2)
C300.115 (4)0.051 (3)0.228 (7)0.025 (3)0.096 (5)0.027 (4)
C310.104 (3)0.058 (2)0.108 (4)0.026 (2)0.024 (3)0.033 (2)
C320.066 (2)0.056 (2)0.084 (3)0.0081 (18)0.005 (2)0.025 (2)
C330.122 (4)0.054 (2)0.086 (3)0.000 (2)0.065 (3)0.000 (2)
C340.182 (6)0.058 (3)0.122 (4)0.006 (3)0.107 (4)0.002 (3)
F10.120 (3)0.491 (9)0.084 (2)0.005 (4)0.011 (2)0.014 (4)
F20.337 (7)0.333 (7)0.349 (8)0.201 (6)0.168 (7)0.262 (7)
F30.0670 (17)0.177 (3)0.129 (2)0.0101 (17)0.0298 (16)0.017 (2)
F40.0848 (18)0.216 (3)0.121 (2)0.0286 (19)0.0281 (17)0.083 (2)
B10.079 (4)0.179 (7)0.095 (5)0.044 (4)0.020 (4)0.066 (5)
O3W0.094 (2)0.161 (3)0.121 (3)0.010 (2)0.001 (2)0.013 (2)
F50.0519 (11)0.0727 (12)0.0573 (12)0.0026 (9)0.0173 (9)0.0241 (10)
Geometric parameters (Å, º) top
O2—C61.370 (4)N1—C241.508 (3)
O2—H2A0.8200N1—H1B0.9001
N2—C81.496 (3)N1—H1C0.9001
N2—C71.498 (4)C18—C251.375 (4)
N2—H2B0.9000C18—C191.389 (4)
N2—H2D0.9000C18—C231.491 (4)
C1—C21.368 (5)C19—C201.372 (4)
C1—C61.372 (5)C20—C211.370 (5)
C1—C71.495 (4)C20—H20A0.9300
C2—C31.379 (5)C21—C221.368 (5)
C2—H2C0.9300C21—H21A0.9300
C3—C41.336 (7)C22—C251.384 (5)
C3—H3A0.9300C22—H22A0.9300
C4—C51.379 (6)C23—H23A0.9700
C4—H4A0.9300C23—H23B0.9700
C5—C61.388 (5)C24—C331.512 (4)
C5—H5A0.9300C24—C321.512 (4)
C7—H7A0.9700C24—C261.518 (4)
C7—H7B0.9700C25—H25A0.9300
C8—C101.519 (4)C26—C281.522 (4)
C8—C91.520 (4)C26—H26A0.9700
C8—C171.525 (4)C26—H26B0.9700
C9—C111.526 (4)C27—C281.483 (5)
C9—H9A0.9700C27—C341.509 (7)
C9—H9B0.9700C27—H27A0.9700
C10—C131.543 (4)C27—H27B0.9700
C10—H10A0.9700C28—C291.490 (5)
C10—H10B0.9700C28—H28A0.9800
C11—C121.518 (5)C29—C311.506 (5)
C11—C141.522 (5)C29—H29A0.9700
C11—H11A0.9800C29—H29B0.9700
C12—C131.502 (5)C30—C311.502 (6)
C12—H12A0.9700C30—C341.522 (7)
C12—H12B0.9700C30—H30A0.9700
C13—C151.523 (5)C30—H30B0.9700
C13—H13A0.9800C31—C321.534 (5)
C14—C161.494 (5)C31—H31A0.9800
C14—H14A0.9700C32—H32A0.9700
C14—H14B0.9700C32—H32B0.9700
C15—C161.527 (5)C33—C341.533 (5)
C15—H15A0.9700C33—H33A0.9700
C15—H15B0.9700C33—H33B0.9700
C16—C171.534 (4)C34—H34A0.9800
C16—H16A0.9800F1—B11.268 (8)
C17—H17A0.9700F2—B11.341 (8)
C17—H17B0.9700F3—B11.331 (6)
O1—C191.354 (3)F4—B11.347 (6)
O1—H1A0.8200O3W—H3C0.8214
N1—C231.492 (3)O3W—H3B0.8203
C6—O2—H2A109.5C23—N1—H1C107.9
C8—N2—C7117.7 (2)C24—N1—H1C112.9
C8—N2—H2B107.9H1B—N1—H1C104.9
C7—N2—H2B107.9C25—C18—C19118.7 (3)
C8—N2—H2D107.9C25—C18—C23122.4 (3)
C7—N2—H2D107.9C19—C18—C23118.9 (3)
H2B—N2—H2D107.2O1—C19—C20122.9 (3)
C2—C1—C6118.6 (3)O1—C19—C18116.5 (3)
C2—C1—C7121.6 (4)C20—C19—C18120.6 (3)
C6—C1—C7119.8 (3)C21—C20—C19119.6 (4)
C1—C2—C3120.8 (4)C21—C20—H20A120.2
C1—C2—H2C119.6C19—C20—H20A120.2
C3—C2—H2C119.6C22—C21—C20121.1 (3)
C4—C3—C2119.9 (5)C22—C21—H21A119.4
C4—C3—H3A120.1C20—C21—H21A119.4
C2—C3—H3A120.1C21—C22—C25119.0 (4)
C3—C4—C5121.4 (4)C21—C22—H22A120.5
C3—C4—H4A119.3C25—C22—H22A120.5
C5—C4—H4A119.3C18—C23—N1112.1 (2)
C4—C5—C6118.2 (4)C18—C23—H23A109.2
C4—C5—H5A120.9N1—C23—H23A109.2
C6—C5—H5A120.9C18—C23—H23B109.2
O2—C6—C1116.0 (3)N1—C23—H23B109.2
O2—C6—C5123.0 (4)H23A—C23—H23B107.9
C1—C6—C5121.0 (4)N1—C24—C33106.8 (2)
C1—C7—N2112.0 (2)N1—C24—C32110.1 (3)
C1—C7—H7A109.2C33—C24—C32110.7 (3)
N2—C7—H7A109.2N1—C24—C26110.7 (2)
C1—C7—H7B109.2C33—C24—C26109.1 (3)
N2—C7—H7B109.2C32—C24—C26109.4 (3)
H7A—C7—H7B107.9C18—C25—C22121.0 (4)
N2—C8—C10110.3 (2)C18—C25—H25A119.5
N2—C8—C9106.9 (2)C22—C25—H25A119.5
C10—C8—C9109.7 (3)C24—C26—C28108.7 (3)
N2—C8—C17110.1 (2)C24—C26—H26A109.9
C10—C8—C17110.5 (2)C28—C26—H26A109.9
C9—C8—C17109.3 (3)C24—C26—H26B109.9
C8—C9—C11109.7 (2)C28—C26—H26B109.9
C8—C9—H9A109.7H26A—C26—H26B108.3
C11—C9—H9A109.7C28—C27—C34109.7 (4)
C8—C9—H9B109.7C28—C27—H27A109.7
C11—C9—H9B109.7C34—C27—H27A109.7
H9A—C9—H9B108.2C28—C27—H27B109.7
C8—C10—C13108.0 (3)C34—C27—H27B109.7
C8—C10—H10A110.1H27A—C27—H27B108.2
C13—C10—H10A110.1C27—C28—C29109.5 (4)
C8—C10—H10B110.1C27—C28—C26109.9 (3)
C13—C10—H10B110.1C29—C28—C26110.3 (3)
H10A—C10—H10B108.4C27—C28—H28A109.0
C12—C11—C14110.2 (3)C29—C28—H28A109.0
C12—C11—C9108.8 (3)C26—C28—H28A109.0
C14—C11—C9108.7 (3)C28—C29—C31110.2 (3)
C12—C11—H11A109.7C28—C29—H29A109.6
C14—C11—H11A109.7C31—C29—H29A109.6
C9—C11—H11A109.7C28—C29—H29B109.6
C13—C12—C11109.5 (3)C31—C29—H29B109.6
C13—C12—H12A109.8H29A—C29—H29B108.1
C11—C12—H12A109.8C31—C30—C34109.7 (4)
C13—C12—H12B109.8C31—C30—H30A109.7
C11—C12—H12B109.8C34—C30—H30A109.7
H12A—C12—H12B108.2C31—C30—H30B109.7
C12—C13—C15110.3 (3)C34—C30—H30B109.7
C12—C13—C10109.8 (3)H30A—C30—H30B108.2
C15—C13—C10109.2 (3)C30—C31—C29108.8 (4)
C12—C13—H13A109.2C30—C31—C32109.8 (3)
C15—C13—H13A109.2C29—C31—C32109.4 (3)
C10—C13—H13A109.2C30—C31—H31A109.6
C16—C14—C11110.2 (3)C29—C31—H31A109.6
C16—C14—H14A109.6C32—C31—H31A109.6
C11—C14—H14A109.6C24—C32—C31108.7 (3)
C16—C14—H14B109.6C24—C32—H32A109.9
C11—C14—H14B109.6C31—C32—H32A109.9
H14A—C14—H14B108.1C24—C32—H32B109.9
C13—C15—C16109.5 (3)C31—C32—H32B109.9
C13—C15—H15A109.8H32A—C32—H32B108.3
C16—C15—H15A109.8C24—C33—C34109.0 (3)
C13—C15—H15B109.8C24—C33—H33A109.9
C16—C15—H15B109.8C34—C33—H33A109.9
H15A—C15—H15B108.2C24—C33—H33B109.9
C14—C16—C15109.9 (3)C34—C33—H33B109.9
C14—C16—C17109.9 (3)H33A—C33—H33B108.3
C15—C16—C17108.5 (3)C27—C34—C30109.5 (4)
C14—C16—H16A109.5C27—C34—C33109.3 (4)
C15—C16—H16A109.5C30—C34—C33108.7 (4)
C17—C16—H16A109.5C27—C34—H34A109.8
C8—C17—C16108.9 (3)C30—C34—H34A109.8
C8—C17—H17A109.9C33—C34—H34A109.8
C16—C17—H17A109.9F1—B1—F3114.8 (6)
C8—C17—H17B109.9F1—B1—F2108.8 (6)
C16—C17—H17B109.9F3—B1—F2110.1 (7)
H17A—C17—H17B108.3F1—B1—F4112.5 (7)
C19—O1—H1A109.5F3—B1—F4108.1 (5)
C23—N1—C24116.8 (2)F2—B1—F4101.8 (6)
C23—N1—H1B110.6H3C—O3W—H3B115.9
C24—N1—H1B103.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···F30.902.263.125 (4)161
N1—H1B···F40.902.262.992 (4)138
N1—H1C···F50.901.742.607 (3)161
N2—H2B···O20.902.132.791 (3)129
N2—H2B···F3i0.902.523.251 (3)139
N2—H2D···F5i0.901.702.600 (3)175
O1—H1A···F5ii0.821.672.487 (3)172
O2—H2A···O3Wi0.821.852.660 (4)168
O3W—H3B···F2iii0.821.972.733 (6)155
O3W—H3C···F10.822.032.842 (6)169
Symmetry codes: (i) x, y+1, z; (ii) x, y, z; (iii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula2C17H24NO+·BF4·F·H2O
Mr640.57
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.4546 (19), 12.532 (3), 15.394 (3)
α, β, γ (°)104.28 (3), 103.20 (3), 94.54 (3)
V3)1703.1 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.10 × 0.05 × 0.05
Data collection
DiffractometerRigaku Mercury2
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
14663, 5987, 2943
Rint0.078
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.221, 1.01
No. of reflections5987
No. of parameters406
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.36

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···F30.902.263.125 (4)160.5
N1—H1B···F40.902.262.992 (4)138.0
N1—H1C···F50.901.742.607 (3)161.3
N2—H2B···O20.902.132.791 (3)129.1
N2—H2B···F3i0.902.523.251 (3)138.8
N2—H2D···F5i0.901.702.600 (3)174.6
O1—H1A···F5ii0.821.672.487 (3)172.2
O2—H2A···O3Wi0.821.852.660 (4)168.2
O3W—H3B···F2iii0.821.972.733 (6)154.7
O3W—H3C···F10.822.032.842 (6)169.0
Symmetry codes: (i) x, y+1, z; (ii) x, y, z; (iii) x+1, y, z+1.
 

Acknowledgements

This work was supported by the Doctoral Foundation of SEU, China.

References

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First citationFu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z., Xiong, R.-G., Huang, S. P. D. & Nakamura, T. (2011c). Angew. Chem. Int. Ed. 50, 11947–11951.  Web of Science CSD CrossRef CAS Google Scholar
First citationFu, D.-W., Zhang, W. & Xiong, R.-G. (2008). Cryst. Growth Des. 8, 3461–3464.  Web of Science CSD CrossRef CAS Google Scholar
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