N,N-Diethyl-5-nitro­pyridin-2-amine

Yufit, D.S.; Turner, M.J.; Howard, J.A.K.

doi:10.1107/S160053680600729X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 62| Part 4| April 2006| Pages o1237-o1239

https://doi.org/10.1107/S160053680600729X

N,N-Diethyl-5-nitropyridin-2-amine

Dmitry S. Yufit,^a ^* Michael J. Turner ^a and Judith A. K. Howard ^a

^aChemistry Department, University of Durham, South Road, Durham DH1 3LE, England
^*Correspondence e-mail: d.s.yufit@durham.ac.uk

(Received 13 February 2006; accepted 28 February 2006; online 3 March 2006)

In the title compound, C₉H₁₃N₃O₂, the asymmetric unit contains two almost identical but crystallographically independent molecules. The molecules are linked together by pairs of weak C—H⋯O interactions into zigzag chains, which, in turn, form corrugated layers perpendicular to the a axis.

Comment

In continuation of our studies of organic molecules with non-linear optical properties (Yufit et al., 2006 ), an attempt to grow crystals of 2-adamantylamino-5-nitropyridine (AANP) (Tomaru et al., 1991 ; Antipin et al., 2001 ) by sublimation has been made. As a result, two types of crystals formed in the reaction vessel. An X-ray study of the small cubic-shaped ones revealed that they are, in fact, crystals of N,N-diethyl-5-nitropyridine-2-amine, (I), which is a side product in the synthesis of AANP. Here, we briefly describe the structural features of this compound.

The asymmetric unit of (I) contains two virtually identical but crystallographically independent molecules (Fig. 1). These molecules differ slightly in the positions of the terminal C atoms of the ethyl groups (Fig. 2).

The packing of the molecules of (I) is quite different from that of its benzene analogue N,N-diethyl-p-nitroaniline (Maurin & Krygowski, 1988 ), in which numerous C—H⋯π interactions are present.

In the crystal structure, molecules are linked together by pairs of C—H⋯O [O1ⁱ⋯H2(—C2) = 2.74 (1) Å, O2ⁱ⋯H3(—C3) = 2.63 (1) Å, O21ⁱⁱ⋯H22(—C22) = 2.67 (1) Å and O22ⁱⁱ⋯H23(—C23) = 2.51 (1) Å; symmetry codes: (i) x, $[{5\over 2}]$ − y, $[{1\over 2}]$ + z, (ii) x, $[{5\over 2}]$ − y, − $[{1\over 2}]$ + z] interactions in zigzag chains parallel to the c axis (Fig. 3); each independent molecule forms separate chains. These chains form corrugated layers perpendicular to a axis (Fig. 4). The pyridine rings of the molecules in adjacent layers are partially overlapped, the shortest interplanar distance being 3.42 Å, which is within the normal range for π–π aromatic interactions (Janiak, 2000 ).

Figure 1
The asymmetric unit of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
A least-squares fit of the pyridine rings of the two independent molecules.

Figure 3
The chains of molecules of (I)

in a single layer. H atoms of ethyl groups have been omitted for clarity. Dashed lines indicate hydrogen bonds.

Figure 4
A packing diagram for (I)

, viewed down the a axis.

Experimental

The title compound, (I), was isolated by chromatography from the mixture of products of the reaction between 2-chloronitropyridine (0.948 g, 5.979 mmol) and adamantylamine (0.984 g, 6.594 mmol). The crystals of (I) were formed on heating the powder sample at 343 K for 3 d (yield 0.99 g, 61%; m.p. 440 K).

Crystal data

C₉H₁₃N₃O₂
M_r = 195.22
Monoclinic, P 2₁ /c
a = 14.6723 (7) Å
b = 10.6920 (5) Å
c = 12.4224 (5) Å
β = 96.820 (1)°
V = 1934.99 (15) Å³
Z = 8
D_x = 1.340 Mg m⁻³
Mo- Kα radiation
Cell parameters from 4483 reflections
θ = 2.4–30.4°
μ = 0.10 mm⁻¹
T = 120 (2) K
Block, yellow
0.26 × 0.14 × 0.12 mm

Data collection

Bruker SMART CCD 6000 diffractometer
ω scans
Absorption correction: none
19597 measured reflections
5389 independent reflections
3536 reflections with I > 2σ(I)
R_int = 0.048
θ_max = 29.5°
h = −20 → 20
k = −14 → 14
l = −17 → 17

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.112
S = 0.97
5389 reflections
357 parameters
All H-atom parameters refined
w = 1/[σ²(F_o²) + (0.06P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

O1—N1	1.2387 (14)
O2—N1	1.2378 (15)
O21—N21	1.2368 (14)
O22—N21	1.2356 (14)
N1—C1	1.4365 (16)
N2—C5	1.3263 (16)
N2—C4	1.3626 (15)
N3—C4	1.3455 (15)
N3—C8	1.4658 (15)
N3—C6	1.4692 (16)
N21—C21	1.4333 (15)
N22—C25	1.3276 (17)
N22—C24	1.3612 (16)
N23—C24	1.3509 (15)
N23—C28	1.4620 (17)
N23—C26	1.4660 (16)

O2—N1—O1	122.69 (11)
O2—N1—C1	118.57 (11)
O1—N1—C1	118.74 (11)
C5—N2—C4	117.73 (11)
C4—N3—C8	121.56 (10)
C4—N3—C6	121.56 (10)
C8—N3—C6	116.44 (10)
O22—N21—O21	122.40 (11)
O22—N21—C21	118.76 (10)
O21—N21—C21	118.83 (11)
C25—N22—C24	117.57 (11)
C24—N23—C28	121.83 (10)
C24—N23—C26	121.11 (11)
C28—N23—C26	117.04 (10)
N3—C4—N2	116.80 (11)
N3—C4—C3	121.76 (11)

H atoms were located in a difference synthesis and refined isotropically [C—H = 0.922 (14)–0.976 (14) for CH, 0.965 (13)–1.007 (14) for CH₂ and 0.970 (17)–1.028 (16) Å for CH₃].

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680600729X/hk2006sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680600729X/hk2006Isup2.hkl

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N,N-diethyl-5-nitropyridine-2-amine top

Crystal data top

C₉H₁₃N₃O₂	F(000) = 832
M_r = 195.22	D_x = 1.340 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4483 reflections
a = 14.6723 (7) Å	θ = 2.4–30.4°
b = 10.6920 (5) Å	µ = 0.10 mm⁻¹
c = 12.4224 (5) Å	T = 120 K
β = 96.820 (1)°	Block, yellow
V = 1934.99 (15) Å³	0.26 × 0.14 × 0.12 mm
Z = 8

Data collection top

Bruker SMART CCD 6000 diffractometer	3536 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 29.5°, θ_min = 1.4°
ω scans	h = −20→20
19597 measured reflections	k = −14→14
5389 independent reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: difference Fourier map
wR(F²) = 0.112	All H-atom parameters refined
S = 0.97	w = 1/[σ²(F_o²) + (0.06P)²] where P = (F_o² + 2F_c²)/3
5389 reflections	(Δ/σ)_max = 0.001
357 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.88641 (7)	1.16690 (10)	−0.20267 (7)	0.0395 (3)
O2	0.85357 (7)	1.31005 (9)	−0.08920 (8)	0.0394 (2)
O21	0.35252 (8)	1.16353 (10)	1.18822 (7)	0.0408 (3)
O22	0.34599 (7)	1.31229 (9)	1.06912 (7)	0.0336 (2)
N1	0.86987 (8)	1.20006 (11)	−0.11143 (9)	0.0296 (2)
N2	0.88886 (7)	0.89231 (10)	0.02259 (8)	0.0268 (2)
N3	0.87939 (7)	0.83105 (9)	0.19895 (8)	0.0236 (2)
N21	0.35337 (7)	1.20055 (10)	1.09402 (8)	0.0273 (2)
N22	0.39111 (7)	0.89809 (9)	0.96485 (9)	0.0262 (2)
N23	0.38857 (7)	0.83972 (9)	0.78584 (8)	0.0260 (2)
C1	0.86994 (8)	1.10729 (12)	−0.02779 (10)	0.0244 (3)
C2	0.85663 (8)	1.14175 (12)	0.07749 (10)	0.0251 (3)
C3	0.85941 (8)	1.05069 (11)	0.15475 (10)	0.0234 (3)
C4	0.87580 (8)	0.92429 (11)	0.12583 (10)	0.0223 (2)
C5	0.88623 (9)	0.98302 (12)	−0.05055 (10)	0.0268 (3)
C6	0.90970 (9)	0.70469 (12)	0.17327 (11)	0.0262 (3)
C7	0.83026 (10)	0.61517 (13)	0.14346 (12)	0.0309 (3)
C8	0.86461 (9)	0.85407 (13)	0.31190 (10)	0.0260 (3)
C9	0.95032 (10)	0.89981 (14)	0.38086 (11)	0.0328 (3)
C21	0.36342 (8)	1.11063 (11)	1.01067 (9)	0.0229 (3)
C22	0.35764 (8)	1.14762 (11)	0.90234 (10)	0.0224 (2)
C23	0.36722 (8)	1.05862 (11)	0.82571 (10)	0.0226 (2)
C24	0.38215 (8)	0.93229 (11)	0.85857 (10)	0.0230 (3)
C25	0.38127 (8)	0.98655 (12)	1.03757 (10)	0.0262 (3)
C26	0.41529 (9)	0.71269 (12)	0.82107 (12)	0.0283 (3)
C27	0.33357 (10)	0.62959 (14)	0.83556 (14)	0.0362 (3)
C28	0.37213 (10)	0.86210 (13)	0.66905 (10)	0.0287 (3)
C29	0.45757 (11)	0.90510 (15)	0.62215 (12)	0.0361 (3)
H2	0.8458 (9)	1.2287 (13)	0.0962 (11)	0.025 (3)*
H3	0.8547 (10)	1.0713 (13)	0.2259 (11)	0.029 (4)*
H5	0.8977 (9)	0.9588 (14)	−0.1233 (12)	0.035 (4)*
H61	0.9503 (10)	0.6739 (13)	0.2380 (12)	0.034 (4)*
H62	0.9477 (9)	0.7122 (12)	0.1149 (11)	0.025 (3)*
H71	0.7969 (11)	0.6413 (14)	0.0736 (13)	0.040 (4)*
H72	0.8559 (10)	0.5284 (15)	0.1329 (12)	0.042 (4)*
H73	0.7881 (10)	0.6140 (13)	0.1993 (12)	0.036 (4)*
H81	0.8431 (9)	0.7764 (13)	0.3393 (10)	0.023 (3)*
H82	0.8137 (9)	0.9168 (13)	0.3140 (10)	0.027 (4)*
H91	0.9978 (12)	0.8369 (16)	0.3803 (13)	0.052 (5)*
H92	0.9758 (10)	0.9807 (15)	0.3509 (12)	0.041 (4)*
H93	0.9373 (11)	0.9131 (15)	0.4526 (14)	0.048 (5)*
H22	0.3491 (9)	1.2342 (12)	0.8839 (10)	0.019 (3)*
H23	0.3659 (9)	1.0812 (13)	0.7504 (11)	0.029 (4)*
H25	0.3891 (9)	0.9642 (13)	1.1136 (11)	0.030 (4)*
H261	0.4578 (10)	0.7189 (13)	0.8895 (11)	0.028 (4)*
H262	0.4534 (10)	0.6804 (13)	0.7657 (12)	0.031 (4)*
H271	0.3047 (11)	0.6582 (15)	0.8981 (13)	0.045 (5)*
H272	0.3546 (11)	0.5419 (17)	0.8529 (13)	0.050 (5)*
H273	0.2913 (11)	0.6265 (15)	0.7689 (13)	0.044 (4)*
H281	0.3220 (10)	0.9221 (13)	0.6533 (11)	0.030 (4)*
H282	0.3488 (10)	0.7821 (14)	0.6362 (11)	0.030 (4)*
H291	0.5053 (12)	0.8409 (16)	0.6329 (13)	0.052 (5)*
H292	0.4821 (11)	0.9817 (16)	0.6565 (12)	0.044 (4)*
H293	0.4438 (10)	0.9218 (14)	0.5436 (13)	0.038 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0501 (6)	0.0455 (6)	0.0230 (5)	−0.0122 (5)	0.0038 (4)	0.0050 (4)
O2	0.0465 (6)	0.0308 (5)	0.0411 (6)	0.0025 (4)	0.0057 (5)	0.0107 (5)
O21	0.0614 (7)	0.0411 (6)	0.0210 (5)	0.0002 (5)	0.0086 (5)	−0.0017 (4)
O22	0.0426 (6)	0.0275 (5)	0.0300 (5)	0.0021 (4)	0.0020 (4)	−0.0050 (4)
N1	0.0276 (6)	0.0330 (6)	0.0274 (6)	−0.0054 (5)	−0.0001 (4)	0.0061 (5)
N2	0.0316 (6)	0.0256 (5)	0.0235 (5)	−0.0018 (4)	0.0051 (4)	−0.0023 (4)
N3	0.0273 (5)	0.0211 (5)	0.0228 (5)	0.0006 (4)	0.0041 (4)	0.0002 (4)
N21	0.0286 (6)	0.0303 (6)	0.0230 (5)	−0.0007 (4)	0.0030 (4)	−0.0028 (5)
N22	0.0293 (6)	0.0239 (5)	0.0253 (5)	0.0002 (4)	0.0029 (4)	0.0024 (4)
N23	0.0304 (6)	0.0212 (5)	0.0260 (5)	0.0019 (4)	0.0018 (4)	−0.0005 (4)
C1	0.0232 (6)	0.0273 (6)	0.0224 (6)	−0.0033 (5)	0.0018 (5)	0.0047 (5)
C2	0.0227 (6)	0.0233 (6)	0.0294 (7)	−0.0002 (5)	0.0027 (5)	−0.0009 (5)
C3	0.0262 (6)	0.0238 (6)	0.0205 (6)	−0.0001 (5)	0.0041 (5)	−0.0022 (5)
C4	0.0212 (6)	0.0229 (6)	0.0226 (6)	−0.0015 (5)	0.0019 (5)	−0.0010 (5)
C5	0.0299 (7)	0.0296 (7)	0.0209 (6)	−0.0045 (5)	0.0038 (5)	−0.0016 (5)
C6	0.0268 (6)	0.0222 (6)	0.0296 (7)	0.0019 (5)	0.0031 (5)	0.0001 (5)
C7	0.0308 (7)	0.0252 (7)	0.0361 (8)	−0.0012 (5)	0.0019 (6)	−0.0005 (6)
C8	0.0300 (7)	0.0257 (6)	0.0227 (6)	−0.0004 (5)	0.0051 (5)	0.0033 (5)
C9	0.0347 (8)	0.0377 (8)	0.0252 (7)	−0.0005 (6)	0.0000 (6)	0.0011 (6)
C21	0.0229 (6)	0.0246 (6)	0.0212 (6)	−0.0017 (5)	0.0029 (5)	−0.0025 (5)
C22	0.0213 (6)	0.0214 (6)	0.0245 (6)	−0.0006 (5)	0.0026 (5)	0.0011 (5)
C23	0.0235 (6)	0.0235 (6)	0.0209 (6)	0.0006 (5)	0.0028 (5)	0.0019 (5)
C24	0.0207 (6)	0.0235 (6)	0.0248 (6)	−0.0008 (5)	0.0030 (5)	−0.0002 (5)
C25	0.0280 (7)	0.0272 (6)	0.0234 (6)	−0.0015 (5)	0.0025 (5)	0.0032 (5)
C26	0.0288 (7)	0.0209 (6)	0.0354 (7)	0.0013 (5)	0.0041 (6)	−0.0007 (6)
C27	0.0317 (8)	0.0271 (7)	0.0493 (9)	−0.0018 (6)	0.0034 (7)	0.0003 (7)
C28	0.0327 (7)	0.0280 (7)	0.0250 (6)	0.0014 (6)	0.0016 (5)	−0.0047 (5)
C29	0.0405 (8)	0.0386 (8)	0.0304 (8)	0.0005 (7)	0.0097 (6)	−0.0023 (7)

Geometric parameters (Å, º) top

O1—N1	1.2387 (14)	C7—H72	1.015 (16)
O2—N1	1.2378 (15)	C7—H73	0.983 (15)
O21—N21	1.2368 (14)	C8—C9	1.516 (2)
O22—N21	1.2356 (14)	C8—H81	0.965 (13)
N1—C1	1.4365 (16)	C8—H82	1.007 (14)
N2—C5	1.3263 (16)	C9—H91	0.970 (17)
N2—C4	1.3626 (15)	C9—H92	1.028 (16)
N3—C4	1.3455 (15)	C9—H93	0.944 (17)
N3—C8	1.4658 (15)	C21—C25	1.3855 (17)
N3—C6	1.4692 (16)	C21—C22	1.3955 (16)
N21—C21	1.4333 (15)	C22—C23	1.3650 (17)
N22—C25	1.3276 (17)	C22—H22	0.958 (13)
N22—C24	1.3612 (16)	C23—C24	1.4205 (17)
N23—C24	1.3509 (15)	C23—H23	0.964 (14)
N23—C28	1.4620 (17)	C25—H25	0.968 (14)
N23—C26	1.4660 (16)	C26—C27	1.5201 (19)
C1—C5	1.3851 (18)	C26—H261	0.995 (14)
C1—C2	1.3946 (18)	C26—H262	0.997 (14)
C2—C3	1.3644 (18)	C27—H271	0.977 (16)
C2—H2	0.976 (14)	C27—H272	1.003 (17)
C3—C4	1.4261 (17)	C27—H273	0.974 (17)
C3—H3	0.922 (14)	C28—C29	1.515 (2)
C5—H5	0.974 (14)	C28—H281	0.978 (14)
C6—C7	1.5197 (19)	C28—H282	0.991 (15)
C6—H61	0.997 (15)	C29—H291	0.978 (18)
C6—H62	0.970 (13)	C29—H292	0.973 (17)
C7—H71	0.985 (16)	C29—H293	0.989 (15)

O2—N1—O1	122.69 (11)	H81—C8—H82	106.9 (11)
O2—N1—C1	118.57 (11)	C8—C9—H91	108.7 (10)
O1—N1—C1	118.74 (11)	C8—C9—H92	112.3 (8)
C5—N2—C4	117.73 (11)	H91—C9—H92	106.8 (13)
C4—N3—C8	121.56 (10)	C8—C9—H93	109.6 (10)
C4—N3—C6	121.56 (10)	H91—C9—H93	109.7 (13)
C8—N3—C6	116.44 (10)	H92—C9—H93	109.7 (13)
O22—N21—O21	122.40 (11)	C25—C21—C22	119.48 (11)
O22—N21—C21	118.76 (10)	C25—C21—N21	120.05 (11)
O21—N21—C21	118.83 (11)	C22—C21—N21	120.45 (11)
C25—N22—C24	117.57 (11)	C23—C22—C21	118.39 (11)
C24—N23—C28	121.83 (10)	C23—C22—H22	121.9 (8)
C24—N23—C26	121.11 (11)	C21—C22—H22	119.7 (8)
C28—N23—C26	117.04 (10)	C22—C23—C24	119.18 (11)
C5—C1—C2	119.45 (11)	C22—C23—H23	120.7 (8)
C5—C1—N1	120.00 (11)	C24—C23—H23	120.1 (8)
C2—C1—N1	120.51 (11)	N23—C24—N22	116.45 (11)
C3—C2—C1	118.38 (12)	N23—C24—C23	121.68 (11)
C3—C2—H2	120.3 (8)	N22—C24—C23	121.87 (11)
C1—C2—H2	121.3 (8)	N22—C25—C21	123.42 (12)
C2—C3—C4	119.40 (11)	N22—C25—H25	118.6 (8)
C2—C3—H3	120.3 (9)	C21—C25—H25	118.0 (8)
C4—C3—H3	120.1 (9)	N23—C26—C27	112.96 (11)
N3—C4—N2	116.80 (11)	N23—C26—H261	108.2 (8)
N3—C4—C3	121.76 (11)	C27—C26—H261	111.1 (8)
N2—C4—C3	121.44 (11)	N23—C26—H262	105.5 (8)
N2—C5—C1	123.59 (11)	C27—C26—H262	113.1 (8)
N2—C5—H5	116.6 (9)	H261—C26—H262	105.5 (11)
C1—C5—H5	119.8 (9)	C26—C27—H271	109.5 (9)
N3—C6—C7	112.89 (11)	C26—C27—H272	110.2 (10)
N3—C6—H61	107.2 (8)	H271—C27—H272	105.9 (13)
C7—C6—H61	110.9 (8)	C26—C27—H273	110.5 (10)
N3—C6—H62	107.6 (8)	H271—C27—H273	113.2 (13)
C7—C6—H62	111.3 (8)	H272—C27—H273	107.5 (13)
H61—C6—H62	106.8 (12)	N23—C28—C29	112.63 (12)
C6—C7—H71	108.8 (9)	N23—C28—H281	109.7 (8)
C6—C7—H72	108.8 (9)	C29—C28—H281	111.2 (8)
H71—C7—H72	107.4 (12)	N23—C28—H282	106.0 (8)
C6—C7—H73	111.4 (9)	C29—C28—H282	111.4 (8)
H71—C7—H73	109.8 (12)	H281—C28—H282	105.6 (11)
H72—C7—H73	110.7 (12)	C28—C29—H291	110.2 (10)
N3—C8—C9	112.83 (11)	C28—C29—H292	111.5 (9)
N3—C8—H81	106.5 (8)	H291—C29—H292	108.0 (14)
C9—C8—H81	111.2 (8)	C28—C29—H293	110.7 (9)
N3—C8—H82	109.4 (7)	H291—C29—H293	108.7 (12)
C9—C8—H82	109.8 (8)	H292—C29—H293	107.6 (12)

Acknowledgements

We thank the EPSRC (UK) for financial support.

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