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ISSN: 2056-9890

4-Bromo-N2,N2,N6,N6-tetra­ethyl­pyridine-2,6-dicarboxamide

aUniversity of Nevada, Reno, Department of Chemistry, 1664 N. Virginia St, Reno, NV 89557-0216, USA
*Correspondence e-mail: abd@unr.edu

(Received 6 July 2010; accepted 19 July 2010; online 24 July 2010)

The title compound, C15H22BrN3O2, consists of a pyridine ring with a bromine atom in the para position and two diethyl­amide groups in the ortho positions of the ring. Despite the positions of the three substituents on the pyridine ring, the mol­ecule does not exhibit either local or crystallographic twofold symmetry as the two diethyl­amido units exhibit significantly different Npy—C—C—Nam torsion angles of 46.3 (4) and 62.7 (4)° (py is pyridine and am is amine). Inter­molecular C—H⋯O inter­actions support the packing.

Related literature

The title compound has been investigated as a sensitizer of lanthanide ion luminescence. For uses of this ligand and its derivatives, see: de Bettencourt-Dias et al. (2006[de Bettencourt-Dias, A. & Poloukhtine, A. (2006). J. Phys. Chem. B, 110, 25638-25645.]); Renaud et al. (1997[Renaud, F., Piguet, C., Bernardinelli, G. & Bünzli, J.-C. G. (1997). Chem. Eur. J. 3, 1646-1659.]). For other structures involving this moiety, see: Muller et al. (2003[Muller, G., Schmidt, B., Jiřiček, J., Bünzli, J.-C. G. & Schenk, K. J. (2003). Acta Cryst. C59, o353-o356.]).

[Scheme 1]

Experimental

Crystal data
  • C15H22BrN3O2

  • Mr = 356.27

  • Orthorhombic, P b c a

  • a = 17.7096 (4) Å

  • b = 8.4987 (2) Å

  • c = 21.5013 (4) Å

  • V = 3236.13 (12) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 2.55 mm−1

  • T = 100 K

  • 0.17 × 0.08 × 0.07 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.670, Tmax = 0.852

  • 23172 measured reflections

  • 3392 independent reflections

  • 2499 reflections with I > 2σ(I)

  • Rint = 0.045

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.101

  • S = 1.05

  • 3392 reflections

  • 194 parameters

  • H-atom parameters constrained

  • Δρmax = 0.56 e Å−3

  • Δρmin = −0.58 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯O1i 0.95 2.54 3.429 (4) 156
C8—H8A⋯O2ii 0.99 2.59 3.250 (4) 124
C9—H9A⋯O1iii 0.98 2.48 3.447 (4) 168
C9—H9B⋯O2ii 0.98 2.87 3.479 (4) 121
C10—H10A⋯O1iii 0.99 2.72 3.652 (4) 157
C13—H13A⋯O2iv 0.99 2.63 3.415 (4) 135
C14—H14A⋯O2iv 0.99 2.73 3.444 (4) 130
C15—H15A⋯O2iv 0.98 2.99 3.525 (4) 115
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (ii) [-x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (iii) -x, -y, -z+1; (iv) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

The title compound, shown in Figure 1 and Scheme 1, is often utillized as the chelating and sensitizing moiety in ligands for lanthanide ion luminescent complexes, such as in (tert-butoxycarbonyl) alanine methyl ester, the structure of which has been reported (Muller et al., 2003) or in a N,N,N',N'-tetraethylpyridine-2,6,dicarboxamide-based ligand (Renaud et al., 1997). It has also been used as an intermediate to ligands capable of coordinating lanthanide ions (de Bettencourt-Dias et al., 2006) and as such was isolated in our research group. It consists of a pyridine ring with a bromide in position 4 and diethylamide groups in positions 2 and 5. This molecule is devoid of crystallographic symmetry and the asymmetric unit comprises one molecule. While at first impression the amide groups seem to be related by a twofold axis, closer inspection shows that they are different. This is evidenced by the torsion angles between the groups and the pyridine ring. The torsion angle for the atoms N1—C1—C7—N2 is 62.7 (4)° and the torsion angle for N1—C5—C6—N3 is 46.3 (4)°. The observed difference between the two ethyl groups might be a consequence of the C—H···O hydrogen bond interactions in which they are involved and which help support the packing structure, shown in Figure 2. Despite the presence of the pyridine rings and of the bromine atoms, ππ, C—Br···π or C—H···Br interactions are not observed.

Related literature top

The title compound has been pursued as a sensitizer of lanthanide ion luminescence. For uses of this ligand and its derivatives, see: de Bettencourt-Dias et al. (2006); Renaud et al. (1997). For other structures involving this moiety, see: Muller et al. (2003).

Experimental top

The title compound was synthesized as follows. PBr5 was obtained by slowly adding 8 ml of PBr3 to 3.5 ml of Br2 in 20 ml hexanes at 0 °C. After one hour, the hexanes were decanted and 5 g of chelidamic acid were added. The mixture was heated for six hours (85–90 °C.) The acid bromide which formed in this step was then extracted with chloroform and used without further purification in the next step.

The solution of the acid bromide in CHCl3 was slowly added to 2-chlorodiethylamine (2 eq.) in 50 ml H2O/KOH (5 eq.) at 0 °C, stirred for 20 minutes, then allowed to slowly warm to room temperature. The aqueous layer was washed and discarded. The organic layer was concentrated, filtered, and the product rinsed with water and hexanes. Crystals were grown by allowing a solution of (I) in CHCl3 to evaporate overnight. Overall yield: 5.7 g, 59%. 1H NMR (400 MHz, CDCl3) p.p.m.: 7.80 (m, 2H), 3.55 (q, 4H), 3.33 (q, 4H), 1.25 (t, 6H), 1.15 (dd, 6H).

Refinement top

Hydrogen atoms were positioned geometrically using a riding model with C—H = 0.95, 0.99 and 0.98 Å for aromatic CH and aliphatic CH2 and CH3 H atoms, respectively, and Uiso(H)=1.2–1.5 Ueq(C).

Structure description top

The title compound, shown in Figure 1 and Scheme 1, is often utillized as the chelating and sensitizing moiety in ligands for lanthanide ion luminescent complexes, such as in (tert-butoxycarbonyl) alanine methyl ester, the structure of which has been reported (Muller et al., 2003) or in a N,N,N',N'-tetraethylpyridine-2,6,dicarboxamide-based ligand (Renaud et al., 1997). It has also been used as an intermediate to ligands capable of coordinating lanthanide ions (de Bettencourt-Dias et al., 2006) and as such was isolated in our research group. It consists of a pyridine ring with a bromide in position 4 and diethylamide groups in positions 2 and 5. This molecule is devoid of crystallographic symmetry and the asymmetric unit comprises one molecule. While at first impression the amide groups seem to be related by a twofold axis, closer inspection shows that they are different. This is evidenced by the torsion angles between the groups and the pyridine ring. The torsion angle for the atoms N1—C1—C7—N2 is 62.7 (4)° and the torsion angle for N1—C5—C6—N3 is 46.3 (4)°. The observed difference between the two ethyl groups might be a consequence of the C—H···O hydrogen bond interactions in which they are involved and which help support the packing structure, shown in Figure 2. Despite the presence of the pyridine rings and of the bromine atoms, ππ, C—Br···π or C—H···Br interactions are not observed.

The title compound has been pursued as a sensitizer of lanthanide ion luminescence. For uses of this ligand and its derivatives, see: de Bettencourt-Dias et al. (2006); Renaud et al. (1997). For other structures involving this moiety, see: Muller et al. (2003).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, with atom numbering (except H atoms) and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed down the b axis. The hydrogen bonds are drawn as dashed lines. Hydrogen atoms not involved in hydrogen bonding interactions were omitted for clarity.
4-Bromo-N2,N2,N6,N6-tetraethylpyridine-2,6- dicarboxamide top
Crystal data top
C15H22BrN3O2F(000) = 1472
Mr = 356.27Dx = 1.462 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4936 reflections
a = 17.7096 (4) Åθ = 2.8–27.8°
b = 8.4987 (2) ŵ = 2.55 mm1
c = 21.5013 (4) ÅT = 100 K
V = 3236.13 (12) Å3Needle, clear light yellow
Z = 80.17 × 0.08 × 0.07 mm
Data collection top
Bruker APEX CCD
diffractometer
3392 independent reflections
Radiation source: fine-focus sealed tube2499 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
phi and ω scansθmax = 26.7°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 2216
Tmin = 0.670, Tmax = 0.852k = 1010
23172 measured reflectionsl = 2627
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0375P)2 + 6.2825P]
where P = (Fo2 + 2Fc2)/3
3392 reflections(Δ/σ)max = 0.001
194 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = 0.58 e Å3
Crystal data top
C15H22BrN3O2V = 3236.13 (12) Å3
Mr = 356.27Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 17.7096 (4) ŵ = 2.55 mm1
b = 8.4987 (2) ÅT = 100 K
c = 21.5013 (4) Å0.17 × 0.08 × 0.07 mm
Data collection top
Bruker APEX CCD
diffractometer
3392 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
2499 reflections with I > 2σ(I)
Tmin = 0.670, Tmax = 0.852Rint = 0.045
23172 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 1.05Δρmax = 0.56 e Å3
3392 reflectionsΔρmin = 0.58 e Å3
194 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*/Ueq
Br10.122569 (19)0.65446 (4)0.436078 (17)0.02253 (12)
N10.02418 (15)0.1655 (3)0.38110 (12)0.0146 (6)
C20.13042 (19)0.3352 (4)0.39707 (14)0.0152 (7)
H20.18350.35070.39590.018*
C60.10501 (18)0.2584 (4)0.39805 (14)0.0157 (7)
C30.08262 (19)0.4540 (4)0.41694 (15)0.0166 (7)
C40.00592 (19)0.4288 (4)0.41939 (14)0.0164 (7)
H40.02770.50910.43270.020*
C50.02047 (17)0.2821 (4)0.40168 (14)0.0126 (6)
C10.09906 (18)0.1947 (4)0.37915 (14)0.0133 (7)
C70.14800 (18)0.0595 (4)0.35846 (15)0.0165 (7)
C90.26126 (18)0.1403 (4)0.46580 (16)0.0214 (8)
H9A0.24190.08300.50200.032*
H9B0.31440.11300.45920.032*
H9C0.25680.25380.47310.032*
C150.2606 (2)0.0792 (5)0.25542 (17)0.0318 (10)
H15A0.25250.01100.21930.048*
H15B0.28990.17180.24280.048*
H15C0.28850.02120.28740.048*
C140.1854 (2)0.1311 (4)0.28117 (17)0.0261 (8)
H14A0.15790.19140.24900.031*
H14B0.19390.20170.31710.031*
C130.0897 (2)0.0736 (4)0.25344 (16)0.0226 (8)
H13A0.11660.07420.21310.027*
H13B0.07940.18430.26500.027*
C80.21630 (18)0.0963 (4)0.40922 (16)0.0194 (7)
H8A0.22510.01610.39960.023*
H8B0.23430.15910.37340.023*
C110.0732 (2)0.1413 (4)0.4195 (2)0.0338 (10)
H11A0.11670.18100.39610.051*
H11B0.05570.22220.44860.051*
H11C0.03240.11500.39050.051*
C100.0960 (2)0.0050 (4)0.45545 (17)0.0218 (8)
H10A0.12940.02640.49020.026*
H10B0.05020.05340.47360.026*
C120.0153 (2)0.0114 (5)0.24541 (19)0.0371 (10)
H12A0.02490.12240.23580.056*
H12B0.01310.03680.21130.056*
H12C0.01400.00370.28390.056*
N30.13501 (14)0.1225 (3)0.41736 (13)0.0139 (6)
N20.13906 (15)0.0027 (3)0.30094 (12)0.0172 (6)
O20.14317 (12)0.3659 (3)0.37517 (11)0.0202 (5)
O10.19438 (13)0.0070 (3)0.39535 (10)0.0209 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0197 (2)0.01536 (18)0.0325 (2)0.00308 (14)0.00063 (16)0.00522 (15)
N10.0166 (14)0.0131 (13)0.0141 (13)0.0011 (11)0.0015 (11)0.0005 (11)
C20.0151 (17)0.0178 (16)0.0127 (15)0.0028 (14)0.0021 (13)0.0008 (13)
C60.0174 (17)0.0162 (16)0.0135 (16)0.0016 (14)0.0000 (14)0.0022 (13)
C30.0200 (18)0.0113 (16)0.0185 (17)0.0017 (14)0.0041 (14)0.0008 (13)
C40.0178 (18)0.0156 (16)0.0157 (16)0.0031 (14)0.0034 (14)0.0007 (13)
C50.0079 (15)0.0167 (16)0.0131 (16)0.0002 (13)0.0003 (13)0.0027 (13)
C10.0127 (16)0.0161 (16)0.0111 (15)0.0004 (13)0.0018 (13)0.0003 (12)
C70.0169 (17)0.0138 (16)0.0186 (17)0.0028 (13)0.0022 (14)0.0010 (13)
C90.0112 (18)0.0279 (19)0.0252 (18)0.0027 (14)0.0031 (15)0.0034 (16)
C150.033 (2)0.037 (2)0.026 (2)0.0149 (19)0.0127 (17)0.0035 (17)
C140.036 (2)0.0167 (18)0.0251 (19)0.0075 (16)0.0013 (17)0.0057 (15)
C130.020 (2)0.028 (2)0.0197 (18)0.0047 (16)0.0041 (15)0.0047 (15)
C80.0145 (17)0.0184 (16)0.0253 (18)0.0045 (14)0.0016 (15)0.0007 (15)
C110.022 (2)0.0176 (18)0.062 (3)0.0013 (15)0.013 (2)0.0019 (18)
C100.0134 (17)0.0191 (17)0.033 (2)0.0004 (14)0.0016 (15)0.0082 (15)
C120.026 (2)0.055 (3)0.030 (2)0.003 (2)0.0050 (18)0.016 (2)
N30.0051 (13)0.0152 (14)0.0213 (14)0.0007 (10)0.0014 (11)0.0023 (11)
N20.0154 (15)0.0169 (14)0.0192 (15)0.0034 (11)0.0015 (12)0.0030 (12)
O20.0104 (11)0.0212 (13)0.0291 (13)0.0022 (9)0.0010 (10)0.0068 (10)
O10.0163 (12)0.0237 (13)0.0228 (13)0.0049 (10)0.0011 (11)0.0005 (10)
Geometric parameters (Å, º) top
Br1—C31.890 (3)C15—H15C0.9800
N1—C51.343 (4)C14—N21.465 (4)
N1—C11.350 (4)C14—H14A0.9900
C2—C11.372 (4)C14—H14B0.9900
C2—C31.385 (4)C13—N21.474 (4)
C2—H20.9500C13—C121.512 (5)
C6—O21.238 (4)C13—H13A0.9900
C6—N31.338 (4)C13—H13B0.9900
C6—C51.513 (4)C8—N31.467 (4)
C3—C41.376 (5)C8—H8A0.9900
C4—C51.385 (4)C8—H8B0.9900
C4—H40.9500C11—C101.519 (5)
C1—C71.506 (4)C11—H11A0.9800
C7—O11.226 (4)C11—H11B0.9800
C7—N21.337 (4)C11—H11C0.9800
C9—C81.501 (5)C10—N31.465 (4)
C9—H9A0.9800C10—H10A0.9900
C9—H9B0.9800C10—H10B0.9900
C9—H9C0.9800C12—H12A0.9800
C15—C141.509 (5)C12—H12B0.9800
C15—H15A0.9800C12—H12C0.9800
C15—H15B0.9800
C5—N1—C1116.9 (3)C15—C14—H14B109.2
C1—C2—C3118.2 (3)H14A—C14—H14B107.9
C1—C2—H2120.9N2—C13—C12113.6 (3)
C3—C2—H2120.9N2—C13—H13A108.8
O2—C6—N3122.9 (3)C12—C13—H13A108.8
O2—C6—C5117.6 (3)N2—C13—H13B108.8
N3—C6—C5119.5 (3)C12—C13—H13B108.8
C4—C3—C2120.2 (3)H13A—C13—H13B107.7
C4—C3—Br1120.1 (2)N3—C8—C9112.7 (3)
C2—C3—Br1119.7 (2)N3—C8—H8A109.1
C3—C4—C5117.5 (3)C9—C8—H8A109.1
C3—C4—H4121.2N3—C8—H8B109.1
C5—C4—H4121.2C9—C8—H8B109.1
N1—C5—C4123.8 (3)H8A—C8—H8B107.8
N1—C5—C6117.9 (3)C10—C11—H11A109.5
C4—C5—C6117.9 (3)C10—C11—H11B109.5
N1—C1—C2123.3 (3)H11A—C11—H11B109.5
N1—C1—C7115.7 (3)C10—C11—H11C109.5
C2—C1—C7120.9 (3)H11A—C11—H11C109.5
O1—C7—N2123.1 (3)H11B—C11—H11C109.5
O1—C7—C1118.2 (3)N3—C10—C11113.5 (3)
N2—C7—C1118.7 (3)N3—C10—H10A108.9
C8—C9—H9A109.5C11—C10—H10A108.9
C8—C9—H9B109.5N3—C10—H10B108.9
H9A—C9—H9B109.5C11—C10—H10B108.9
C8—C9—H9C109.5H10A—C10—H10B107.7
H9A—C9—H9C109.5C13—C12—H12A109.5
H9B—C9—H9C109.5C13—C12—H12B109.5
C14—C15—H15A109.5H12A—C12—H12B109.5
C14—C15—H15B109.5C13—C12—H12C109.5
H15A—C15—H15B109.5H12A—C12—H12C109.5
C14—C15—H15C109.5H12B—C12—H12C109.5
H15A—C15—H15C109.5C6—N3—C8118.9 (3)
H15B—C15—H15C109.5C6—N3—C10125.1 (3)
N2—C14—C15112.0 (3)C8—N3—C10115.2 (3)
N2—C14—H14A109.2C7—N2—C14118.8 (3)
C15—C14—H14A109.2C7—N2—C13124.3 (3)
N2—C14—H14B109.2C14—N2—C13116.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.952.543.429 (4)156
C8—H8A···O2ii0.992.593.250 (4)124
C8—H8B···O20.992.392.732 (4)100
C9—H9A···O1iii0.982.483.447 (4)168
C9—H9B···O2ii0.982.873.479 (4)121
C10—H10A···O1iii0.992.723.652 (4)157
C13—H13A···O2iv0.992.633.415 (4)135
C14—H14A···O2iv0.992.733.444 (4)130
C15—H15A···O2iv0.982.993.525 (4)115
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x1/2, y1/2, z; (iii) x, y, z+1; (iv) x, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H22BrN3O2
Mr356.27
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)100
a, b, c (Å)17.7096 (4), 8.4987 (2), 21.5013 (4)
V3)3236.13 (12)
Z8
Radiation typeMo Kα
µ (mm1)2.55
Crystal size (mm)0.17 × 0.08 × 0.07
Data collection
DiffractometerBruker APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.670, 0.852
No. of measured, independent and
observed [I > 2σ(I)] reflections
23172, 3392, 2499
Rint0.045
(sin θ/λ)max1)0.632
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.101, 1.05
No. of reflections3392
No. of parameters194
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.56, 0.58

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.952.543.429 (4)156
C8—H8A···O2ii0.992.593.250 (4)124
C8—H8B···O20.992.392.732 (4)100
C9—H9A···O1iii0.982.483.447 (4)168
C9—H9B···O2ii0.982.873.479 (4)121
C10—H10A···O1iii0.992.723.652 (4)157
C13—H13A···O2iv0.992.633.415 (4)135
C14—H14A···O2iv0.992.733.444 (4)130
C15—H15A···O2iv0.982.993.525 (4)115
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x1/2, y1/2, z; (iii) x, y, z+1; (iv) x, y1/2, z+1/2.
 

Acknowledgements

The authors thank the University of Nevada, Reno and the National Science Foundation (CHE-0733458) for support.

References

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