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The title compound, C10H8F5NO, crystallizes as a racemate with four symmetry-independent mol­ecules in the asymmetric unit. The four mol­ecules form two hydrogen-bonded pairs. Each pair is a building unit of an independent C(4) chain propagating parallel to the ab plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106012121/hj3006sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106012121/hj3006IIsup2.hkl
Contains datablock II

CCDC reference: 609428

Comment top

We are interested in examining the folding propensities of peptoids, a class of peptidomimetics with interesting structural and biological properties (Simon et al., 1992). In the course of our investigations, we desired to synthesize peptoids containing α-chiral fluoroaromatic side chains in order to explore ππ stacking interactions in peptoid helices (Gorske et al., 2005; Kirshenbaum et al., 1998; Wu et al., 2001). We designed a monomeric system, (I), to determine how this side-chain affects local conformational behavior. A mixture of products was obtained from the solution-phase synthesis of compound (I). Purification by silica-gel chromatography using ethyl acetate as the eluent afforded the desired product and a mixture of by-products (r.f. = 0.6). NMR analysis of the by-products in CDCl3 (300 MHz) indicated that the mixture probably consisted of compounds (II) and (III) in an approximately 3:2 ratio. The mixture was dissolved in 1:1 n-heptane–chloroform and the solution was allowed to evaporate at room temperature, yielding colorless crystals.

The crystals proved to contain only the title compound, (II), in the form of a racemate in the centrosymmetric triclinic spacegroup P1. The asymmetric unit contains four independent molecules (AD) with the same configuration of the stereogenic center C3 (Fig. 1). The Cambridge Structural Database (CSD; Version 5.27 updated January 2006; Allen, 2002) contains 652 structures (0.18%) with Z = 8 and Z' = 4, of which 203 organic and 135 organometallic compounds crystallize in space group P1. Examples include 4-methyl-3-nitroanyline, which forms molecular R34(18) ladders (Cannon et al., 2001), maleimide, which forms discrete R22(8) dimers in the solid state (Cox & Parker, 1996), and 5-nitro-2,4-dihydro-1,2,4-triazol-3-one, which crystallizes as a four-component twin (Bolotina et al., 2005).

In the asymmetric unit of (II), the molecules are positioned pairwise with intermolecular N—H···O hydrogen bonds between molecules A and B and molecules C and D (Fig. 1). The donor–acceptor N···O separations fall in the range 2.8380 (15)–2.8855 (15) Å, with N—H···O angles between 156 and 172°. The relatively strong hydrogen bonds are thought to be the driving force for the crystallization of (II).

The hydrogen-bonding motif in (II) is C(4) (Bernstein et al., 1995) in both cases. The parallel hydrogen-bonded chains of the same chiral configuration propagate in the [120] direction and are stacked in planes with alternating chiral configurations along the crystallographic c axis. While there are no interchain hydrogen bonds, there are a number of F···F contacts that are shorter than the sum of the F `zero-point energy' radius of 2.826 Å, defined as the distance at which the F···F interactions become predominantly repulsive (Guzei & Wendt, 2006). The contacts are between chains A and A(1 + x, y, z), A and C(2 − x, −y, 1 − z), A and C(1 − x, −y, 1 − z), B and D(x, 1 + y, z), and C and C(1 + x, y, z), with the shortest distance being 2.7722 (11) Å between atoms F3A and F4C(1 − x, −y, 1 − z). The energy required to reposition two F atoms from 2.826 to 2.7722 Å has been estimated with a Morse potential and found to be ~0.04 kcal mol−1 (1 kcal mol−1 = 4.184 kJ mol−1).

Interestingly, molecules B and D have similar geometries, while those of A and C are noticeably different. Thus, two different hydrogen-bonded chains are present. It is important to compare Figs. 2 and 3. The lattice content viewed along axis a (Fig. 2) seems to reveal a regualar packing pattern. However, the lattice perspective examined along axis b (Fig. 3) shows that molecules B and D at the short a-axis edges of the lattice are in more similar conformations than molecules A and C, with the offset pentafluorophenyl rings in the middle of the unit cell. A closer inspection of the molecular conformations reveals that all four molecules differ: torsion angles N1—C3—C5—C6 in molecules AD and in the molecule of (II) with its geometry optimized at the pbe1pbe/6–31+G* level of theory (II-DFT) (GAUSSIAN03; Frisch et al., 2004) are 55.23 (17), 64.47 (16), 47.80 (16), 66.39 (16) and 52.3°, respectively. A somewhat smaller variation is observed for torsion angles C2—N1—C3—C5 for the five molecules in the same order: 74.23 (14), 87.95 (15), 81.32 (15), 84.22 (15) and 89.0°.

The average C—F bond length of 1.341 (3) Å for molecules AD is statistically equivalent to the corresponding averaged distance in (II-DFT) [1.334 (6) Å]. A scrutiny of the amide link shows that the delocalization of electron density in the planar H—N—CO unit due to the n(N1) π*(C2O1) donation is more prominent in the experimental data [N1—C2 = 1.340 (3) and C2O1 = 1.232 (2) Å] than in the theoretical model [N1—C2 = 1.37 and C2O1 = 1.22 Å], where the differences are statistically significant. This may in part be attributed to the intermolecular hydrogen bonding, which would elongate the experimentally observed CO double bonds relative to that in the theoretical model, in which intermolecular effects were absent. A natural bond-orbital analysis of (II-DFT) computed the bond orders for bonds N1—C2 and C2O1 to be 1.1 and 1.9, respectively.

Experimental top

A mixture of products was obtained from the solution-phase synthesis of compound (I). [Please give brief details of reagents, quantities and method] Purification by silica-gel chromatography using ethyl acetate as the eluent afforded the desired product and a mixture of by-products (r.f. = 0.6). NMR analysis of the byproducts in CDCl3 (300 MHz) indicated the mixture probably consisted of compounds (II) and (III) in an approximately 3:2 ratio. The mixture was dissolved in 1:1 n-heptane–chloroform and the solution was allowed to evaporate at room temperature, yielding colorless crystals.

Refinement top

All H atoms were placed in idealized locations and refined as riding, with C—H (Me groups) = 0.98 Å, C3—H = 1.00 Å and N—H = 0.88 Å, and with Uiso(H) = 1.2 (for N1 and C3) or 1.5 (for Me groups) times Ueq(parent).

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.

Figures top
[Figure 1] Fig. 1. The molecular structure of (II), showing the four symmetry-independent molecules (suffixes AD). Displacement ellipsoids are drawn at the 50% probability level. All H atoms, except the amide NH atoms, have been omitted for clarity. Hydrogen-bonding interactions are shown as dashed lines.
[Figure 2] Fig. 2. A packing diagram of (II), viewed along the a axis. All H atoms, except the amide NH atoms, have been omitted for clarity. Hydrogen-bonding interactions are shown as dashed lines.
[Figure 3] Fig. 3. A packing diagram of (II), viewed along the b axis. All H atoms, except the amide NH atoms, have been omitted for clarity. Hydrogen-bonding interactions are shown as dashed lines.
N-[1-(Pentafluorophenyl)ethyl]acetamide top
Crystal data top
C10H8F5NOZ = 8
Mr = 253.17F(000) = 1024
Triclinic, P1Dx = 1.620 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4129 (5) ÅCell parameters from 13370 reflections
b = 12.2875 (8) Åθ = 2.7–26.4°
c = 23.5594 (15) ŵ = 0.17 mm1
α = 77.694 (2)°T = 100 K
β = 82.070 (2)°Block, colorless
γ = 89.936 (2)°0.49 × 0.38 × 0.26 mm
V = 2075.7 (2) Å3
Data collection top
Bruker CCD-1000 area-detector
diffractometer
8472 independent reflections
Radiation source: fine-focus sealed tube6949 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
0.30° ω scansθmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = 99
Tmin = 0.923, Tmax = 0.958k = 1515
30498 measured reflectionsl = 2929
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0417P)2 + 0.8749P]
where P = (Fo2 + 2Fc2)/3
8472 reflections(Δ/σ)max = 0.001
621 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C10H8F5NOγ = 89.936 (2)°
Mr = 253.17V = 2075.7 (2) Å3
Triclinic, P1Z = 8
a = 7.4129 (5) ÅMo Kα radiation
b = 12.2875 (8) ŵ = 0.17 mm1
c = 23.5594 (15) ÅT = 100 K
α = 77.694 (2)°0.49 × 0.38 × 0.26 mm
β = 82.070 (2)°
Data collection top
Bruker CCD-1000 area-detector
diffractometer
8472 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
6949 reflections with I > 2σ(I)
Tmin = 0.923, Tmax = 0.958Rint = 0.024
30498 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.089H-atom parameters constrained
S = 1.04Δρmax = 0.32 e Å3
8472 reflectionsΔρmin = 0.23 e Å3
621 parameters
Special details top

Experimental. The 1H NMR (300 MHz) spectrum was recorded on a Bruker AC-300 MHz s pectrometer in CDCl3. Chemical shifts are reported in parts per million (p.p.m., δ) using tetramethyl silane (TMS) as a reference.

1H NMR (CDCl3) δ: 6.09 (m, 1H), 5.50 (dq, J = 7.3 and 7.3 Hz, 1H), 1.99 (s, 3H), 1.54 (d, J = 7.3 Hz, 3H).

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
F1A1.06643 (10)0.50505 (7)0.40483 (4)0.02252 (18)
F2A0.97022 (11)0.35949 (7)0.50744 (3)0.02302 (18)
F3A0.61370 (11)0.29898 (7)0.54514 (3)0.02392 (18)
F4A0.35502 (10)0.38302 (7)0.47850 (4)0.02346 (18)
F5A0.44685 (10)0.53412 (7)0.37763 (4)0.02226 (18)
F1B0.69967 (12)0.51779 (7)0.12690 (4)0.02687 (19)
F2B0.55073 (12)0.67126 (7)0.05021 (4)0.0284 (2)
F3B0.24491 (12)0.62035 (8)0.00789 (4)0.0330 (2)
F4B0.10046 (12)0.40931 (8)0.04012 (4)0.0345 (2)
F5B0.25184 (11)0.25286 (7)0.11489 (4)0.02624 (19)
F1C1.14838 (10)0.02785 (7)0.38191 (3)0.02067 (17)
F2C1.15477 (10)0.12271 (7)0.48251 (4)0.02213 (18)
F3C0.83890 (11)0.20761 (7)0.54984 (3)0.02262 (18)
F4C0.51429 (10)0.14774 (7)0.51308 (3)0.02189 (18)
F5C0.50512 (10)0.00369 (7)0.40986 (3)0.02160 (18)
F1D0.69529 (12)0.01565 (7)0.12802 (4)0.02705 (19)
F2D0.54576 (12)0.16749 (7)0.05083 (4)0.0288 (2)
F3D0.24210 (13)0.11426 (8)0.00802 (4)0.0344 (2)
F4D0.09986 (12)0.09733 (8)0.04077 (4)0.0358 (2)
F5D0.25207 (11)0.25233 (7)0.11628 (4)0.02640 (19)
O1A0.77024 (13)0.47169 (8)0.26288 (4)0.0231 (2)
O1B0.27619 (14)0.22532 (10)0.25183 (5)0.0322 (3)
O1C0.77357 (14)0.03317 (8)0.26310 (4)0.0250 (2)
O1D0.26714 (14)0.26742 (9)0.25192 (5)0.0301 (2)
N1A0.95159 (15)0.59065 (9)0.29087 (5)0.0191 (2)
H1A1.06150.62050.28740.023*
N1B0.54684 (15)0.31722 (9)0.22434 (5)0.0185 (2)
H1AA0.63150.35720.23400.022*
N1C0.95098 (15)0.09232 (9)0.28767 (5)0.0188 (2)
H1BA1.05510.13040.27990.023*
N1D0.54369 (16)0.18251 (9)0.22565 (5)0.0190 (2)
H1CA0.63100.14530.23580.023*
C1A1.0748 (2)0.50318 (13)0.21144 (6)0.0258 (3)
H1B1.10470.42420.21820.039*
H1C1.18170.54760.21420.039*
H1D1.03890.52670.17230.039*
C2A0.91969 (19)0.52021 (11)0.25700 (6)0.0187 (3)
C3A0.80692 (18)0.61858 (11)0.33344 (6)0.0189 (3)
H3A0.69520.63430.31400.023*
C4A0.8617 (2)0.72385 (12)0.35244 (7)0.0263 (3)
H4A0.88430.78550.31800.039*
H4B0.97260.71070.37090.039*
H4C0.76310.74290.38060.039*
C5A0.76033 (18)0.52429 (11)0.38713 (6)0.0166 (3)
C6A0.88934 (17)0.47591 (11)0.42151 (6)0.0177 (3)
C7A0.84258 (18)0.39995 (11)0.47412 (6)0.0183 (3)
C8A0.66213 (18)0.36852 (11)0.49325 (6)0.0179 (3)
C9A0.53068 (18)0.41262 (11)0.45952 (6)0.0182 (3)
C10A0.58058 (18)0.48965 (11)0.40773 (6)0.0171 (3)
C1B0.3872 (2)0.31577 (14)0.32105 (6)0.0298 (3)
H1AB0.27690.35810.32730.045*
H1AC0.49460.36220.32100.045*
H1AD0.38330.24900.35260.045*
C2B0.39776 (19)0.28200 (12)0.26312 (6)0.0216 (3)
C3B0.57094 (18)0.29032 (11)0.16634 (6)0.0183 (3)
H3AA0.50490.21770.16990.022*
C4B0.77208 (19)0.27450 (12)0.14615 (6)0.0225 (3)
H4AA0.81630.21120.17310.034*
H4AB0.84230.34210.14600.034*
H4AC0.78680.26000.10650.034*
C5B0.48369 (18)0.37840 (11)0.12342 (6)0.0182 (3)
C6B0.55220 (19)0.48749 (11)0.10580 (6)0.0195 (3)
C7B0.4750 (2)0.56842 (11)0.06717 (6)0.0219 (3)
C8B0.3209 (2)0.54252 (12)0.04537 (6)0.0234 (3)
C9B0.24824 (19)0.43548 (13)0.06175 (6)0.0235 (3)
C10B0.32946 (19)0.35560 (11)0.10027 (6)0.0199 (3)
C1C1.0663 (2)0.01226 (12)0.20488 (6)0.0237 (3)
H1BB1.10580.06490.21010.036*
H1BC1.16990.06140.20540.036*
H1BD1.01990.03430.16720.036*
C2C0.91760 (18)0.02164 (11)0.25403 (6)0.0183 (3)
C3C0.81841 (18)0.10743 (11)0.33688 (6)0.0180 (3)
H3BA0.69390.10500.32530.022*
C4C0.8494 (2)0.22109 (11)0.35083 (6)0.0228 (3)
H4BA0.83580.27980.31650.034*
H4BB0.97250.22600.36100.034*
H4BC0.75970.23040.38400.034*
C5C0.82652 (18)0.01580 (11)0.39142 (6)0.0162 (3)
C6C0.98873 (17)0.01730 (11)0.41187 (6)0.0165 (3)
C7C0.99507 (18)0.09414 (11)0.46391 (6)0.0177 (3)
C8C0.83463 (19)0.13805 (11)0.49805 (6)0.0177 (3)
C9C0.67011 (17)0.10710 (11)0.47922 (6)0.0176 (3)
C10C0.66826 (17)0.03215 (11)0.42642 (6)0.0169 (3)
C1D0.3735 (2)0.17005 (14)0.31920 (6)0.0286 (3)
H1CB0.34390.23290.35270.043*
H1CC0.27670.11570.31950.043*
H1CD0.48940.13460.32200.043*
C2D0.38942 (19)0.21133 (11)0.26321 (6)0.0203 (3)
C3D0.56865 (18)0.21205 (11)0.16838 (6)0.0186 (3)
H3CA0.50280.28500.17270.022*
C4D0.77017 (19)0.22809 (12)0.14862 (6)0.0230 (3)
H4CA0.81420.29070.17600.034*
H4CB0.84010.16010.14800.034*
H4CC0.78550.24380.10920.034*
C5D0.48162 (18)0.12537 (11)0.12463 (6)0.0183 (3)
C6D0.54882 (19)0.01582 (12)0.10681 (6)0.0200 (3)
C7D0.4712 (2)0.06430 (12)0.06789 (6)0.0225 (3)
C8D0.3183 (2)0.03716 (12)0.04591 (6)0.0240 (3)
C9D0.24684 (19)0.07019 (13)0.06250 (6)0.0242 (3)
C10D0.32836 (19)0.14905 (12)0.10133 (6)0.0206 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.0122 (4)0.0277 (4)0.0273 (4)0.0017 (3)0.0017 (3)0.0059 (3)
F2A0.0223 (4)0.0251 (4)0.0237 (4)0.0048 (3)0.0094 (3)0.0060 (3)
F3A0.0301 (5)0.0211 (4)0.0185 (4)0.0019 (3)0.0010 (3)0.0025 (3)
F4A0.0138 (4)0.0248 (4)0.0305 (4)0.0044 (3)0.0031 (3)0.0072 (4)
F5A0.0148 (4)0.0253 (4)0.0273 (4)0.0023 (3)0.0066 (3)0.0048 (3)
F1B0.0303 (5)0.0206 (4)0.0307 (5)0.0067 (3)0.0123 (4)0.0028 (4)
F2B0.0388 (5)0.0174 (4)0.0272 (4)0.0024 (4)0.0060 (4)0.0000 (3)
F3B0.0351 (5)0.0345 (5)0.0264 (5)0.0067 (4)0.0102 (4)0.0042 (4)
F4B0.0245 (5)0.0454 (6)0.0329 (5)0.0054 (4)0.0134 (4)0.0006 (4)
F5B0.0246 (4)0.0251 (4)0.0283 (4)0.0087 (3)0.0055 (3)0.0029 (4)
F1C0.0126 (4)0.0239 (4)0.0242 (4)0.0022 (3)0.0009 (3)0.0033 (3)
F2C0.0165 (4)0.0229 (4)0.0279 (4)0.0033 (3)0.0085 (3)0.0040 (3)
F3C0.0276 (4)0.0213 (4)0.0178 (4)0.0006 (3)0.0040 (3)0.0009 (3)
F4C0.0172 (4)0.0237 (4)0.0231 (4)0.0046 (3)0.0031 (3)0.0050 (3)
F5C0.0121 (4)0.0273 (4)0.0261 (4)0.0006 (3)0.0048 (3)0.0060 (3)
F1D0.0302 (5)0.0207 (4)0.0316 (5)0.0067 (3)0.0131 (4)0.0030 (4)
F2D0.0386 (5)0.0183 (4)0.0278 (4)0.0022 (4)0.0062 (4)0.0002 (3)
F3D0.0345 (5)0.0378 (5)0.0276 (5)0.0066 (4)0.0111 (4)0.0042 (4)
F4D0.0248 (5)0.0489 (6)0.0334 (5)0.0066 (4)0.0136 (4)0.0023 (4)
F5D0.0245 (4)0.0259 (4)0.0288 (5)0.0087 (3)0.0048 (3)0.0052 (4)
O1A0.0232 (5)0.0221 (5)0.0239 (5)0.0062 (4)0.0035 (4)0.0045 (4)
O1B0.0252 (6)0.0414 (7)0.0302 (6)0.0165 (5)0.0029 (4)0.0122 (5)
O1C0.0247 (5)0.0255 (5)0.0255 (5)0.0090 (4)0.0035 (4)0.0073 (4)
O1D0.0241 (5)0.0375 (6)0.0284 (6)0.0136 (5)0.0009 (4)0.0093 (5)
N1A0.0160 (6)0.0213 (6)0.0194 (6)0.0047 (5)0.0003 (4)0.0046 (5)
N1B0.0180 (6)0.0199 (6)0.0170 (6)0.0058 (4)0.0025 (4)0.0029 (4)
N1C0.0156 (6)0.0220 (6)0.0181 (6)0.0050 (5)0.0016 (4)0.0036 (5)
N1D0.0196 (6)0.0203 (6)0.0176 (6)0.0050 (5)0.0040 (4)0.0042 (5)
C1A0.0274 (8)0.0260 (8)0.0234 (7)0.0016 (6)0.0014 (6)0.0071 (6)
C2A0.0216 (7)0.0164 (6)0.0166 (6)0.0010 (5)0.0038 (5)0.0009 (5)
C3A0.0171 (7)0.0187 (7)0.0201 (7)0.0003 (5)0.0014 (5)0.0032 (5)
C4A0.0322 (8)0.0182 (7)0.0271 (8)0.0018 (6)0.0009 (6)0.0053 (6)
C5A0.0170 (6)0.0153 (6)0.0186 (6)0.0002 (5)0.0013 (5)0.0067 (5)
C6A0.0135 (6)0.0185 (7)0.0222 (7)0.0017 (5)0.0014 (5)0.0078 (5)
C7A0.0189 (7)0.0181 (7)0.0207 (7)0.0037 (5)0.0063 (5)0.0081 (5)
C8A0.0223 (7)0.0152 (6)0.0161 (6)0.0012 (5)0.0005 (5)0.0050 (5)
C9A0.0142 (6)0.0173 (7)0.0237 (7)0.0029 (5)0.0018 (5)0.0088 (5)
C10A0.0167 (6)0.0163 (6)0.0206 (7)0.0026 (5)0.0047 (5)0.0079 (5)
C1B0.0254 (8)0.0406 (9)0.0232 (8)0.0085 (7)0.0014 (6)0.0093 (7)
C2B0.0196 (7)0.0227 (7)0.0212 (7)0.0035 (6)0.0019 (5)0.0025 (6)
C3B0.0192 (7)0.0172 (7)0.0183 (6)0.0027 (5)0.0026 (5)0.0034 (5)
C4B0.0216 (7)0.0223 (7)0.0228 (7)0.0018 (6)0.0025 (6)0.0034 (6)
C5B0.0191 (7)0.0201 (7)0.0154 (6)0.0001 (5)0.0001 (5)0.0053 (5)
C6B0.0206 (7)0.0208 (7)0.0183 (6)0.0008 (5)0.0035 (5)0.0061 (5)
C7B0.0279 (7)0.0176 (7)0.0188 (7)0.0000 (6)0.0002 (6)0.0031 (5)
C8B0.0254 (7)0.0271 (8)0.0161 (7)0.0068 (6)0.0030 (5)0.0009 (6)
C9B0.0180 (7)0.0341 (8)0.0189 (7)0.0003 (6)0.0029 (5)0.0063 (6)
C10B0.0198 (7)0.0206 (7)0.0181 (7)0.0033 (5)0.0012 (5)0.0043 (5)
C1C0.0252 (7)0.0246 (7)0.0211 (7)0.0008 (6)0.0015 (6)0.0053 (6)
C2C0.0204 (7)0.0161 (6)0.0178 (6)0.0002 (5)0.0060 (5)0.0002 (5)
C3C0.0159 (6)0.0191 (7)0.0193 (7)0.0003 (5)0.0043 (5)0.0035 (5)
C4C0.0255 (7)0.0177 (7)0.0255 (7)0.0009 (6)0.0056 (6)0.0040 (6)
C5C0.0175 (6)0.0143 (6)0.0183 (6)0.0000 (5)0.0026 (5)0.0065 (5)
C6C0.0136 (6)0.0164 (6)0.0200 (6)0.0016 (5)0.0001 (5)0.0065 (5)
C7C0.0160 (6)0.0171 (6)0.0226 (7)0.0028 (5)0.0059 (5)0.0081 (5)
C8C0.0227 (7)0.0141 (6)0.0168 (6)0.0001 (5)0.0034 (5)0.0043 (5)
C9C0.0142 (6)0.0174 (7)0.0214 (7)0.0035 (5)0.0018 (5)0.0077 (5)
C10C0.0131 (6)0.0182 (6)0.0217 (7)0.0013 (5)0.0040 (5)0.0085 (5)
C1D0.0271 (8)0.0368 (9)0.0215 (7)0.0050 (7)0.0016 (6)0.0065 (6)
C2D0.0202 (7)0.0191 (7)0.0205 (7)0.0014 (5)0.0044 (5)0.0005 (5)
C3D0.0195 (7)0.0168 (7)0.0193 (7)0.0027 (5)0.0026 (5)0.0038 (5)
C4D0.0210 (7)0.0225 (7)0.0249 (7)0.0011 (6)0.0029 (6)0.0041 (6)
C5D0.0188 (7)0.0207 (7)0.0160 (6)0.0005 (5)0.0009 (5)0.0060 (5)
C6D0.0209 (7)0.0223 (7)0.0185 (7)0.0011 (5)0.0042 (5)0.0069 (5)
C7D0.0274 (7)0.0198 (7)0.0194 (7)0.0003 (6)0.0002 (6)0.0041 (5)
C8D0.0248 (7)0.0291 (8)0.0168 (7)0.0061 (6)0.0038 (5)0.0015 (6)
C9D0.0182 (7)0.0364 (9)0.0192 (7)0.0009 (6)0.0033 (5)0.0083 (6)
C10D0.0201 (7)0.0223 (7)0.0193 (7)0.0034 (5)0.0010 (5)0.0066 (6)
Geometric parameters (Å, º) top
F1A—C6A1.3434 (15)C8A—C9A1.3797 (19)
F2A—C7A1.3402 (15)C9A—C10A1.3804 (19)
F3A—C8A1.3371 (15)C1B—C2B1.501 (2)
F4A—C9A1.3412 (15)C1B—H1AB0.9800
F5A—C10A1.3460 (15)C1B—H1AC0.9800
F1B—C6B1.3456 (15)C1B—H1AD0.9800
F2B—C7B1.3403 (16)C3B—C5B1.5246 (19)
F3B—C8B1.3372 (16)C3B—C4B1.5266 (19)
F4B—C9B1.3372 (16)C3B—H3AA1.0000
F5B—C10B1.3435 (16)C4B—H4AA0.9800
F1C—C6C1.3456 (15)C4B—H4AB0.9800
F2C—C7C1.3391 (15)C4B—H4AC0.9800
F3C—C8C1.3365 (15)C5B—C10B1.3860 (19)
F4C—C9C1.3406 (15)C5B—C6B1.3904 (19)
F5C—C10C1.3447 (15)C6B—C7B1.379 (2)
F1D—C6D1.3458 (15)C7B—C8B1.379 (2)
F2D—C7D1.3408 (16)C8B—C9B1.377 (2)
F3D—C8D1.3382 (16)C9B—C10B1.385 (2)
F4D—C9D1.3371 (16)C1C—C2C1.5078 (19)
F5D—C10D1.3455 (16)C1C—H1BB0.9800
O1A—C2A1.2352 (17)C1C—H1BC0.9800
O1B—C2B1.2307 (17)C1C—H1BD0.9800
O1C—C2C1.2314 (17)C3C—C5C1.5255 (18)
O1D—C2D1.2303 (17)C3C—C4C1.5259 (18)
N1A—C2A1.3374 (17)C3C—H3BA1.0000
N1A—C3A1.4570 (17)C4C—H4BA0.9800
N1A—H1A0.8800C4C—H4BB0.9800
N1B—C2B1.3406 (18)C4C—H4BC0.9800
N1B—C3B1.4607 (17)C5C—C6C1.3851 (19)
N1B—H1AA0.8800C5C—C10C1.3895 (19)
N1C—C2C1.3384 (17)C6C—C7C1.3853 (19)
N1C—C3C1.4564 (17)C7C—C8C1.3803 (19)
N1C—H1BA0.8800C8C—C9C1.3803 (19)
N1D—C2D1.3433 (18)C9C—C10C1.3828 (19)
N1D—C3D1.4581 (17)C1D—C2D1.501 (2)
N1D—H1CA0.8800C1D—H1CB0.9800
C1A—C2A1.5076 (19)C1D—H1CC0.9800
C1A—H1B0.9800C1D—H1CD0.9800
C1A—H1C0.9800C3D—C5D1.5255 (19)
C1A—H1D0.9800C3D—C4D1.5276 (19)
C3A—C5A1.5223 (18)C3D—H3CA1.0000
C3A—C4A1.5286 (19)C4D—H4CA0.9800
C3A—H3A1.0000C4D—H4CB0.9800
C4A—H4A0.9800C4D—H4CC0.9800
C4A—H4B0.9800C5D—C10D1.3847 (19)
C4A—H4C0.9800C5D—C6D1.3925 (19)
C5A—C10A1.3881 (19)C6D—C7D1.378 (2)
C5A—C6A1.3896 (19)C7D—C8D1.379 (2)
C6A—C7A1.3845 (19)C8D—C9D1.378 (2)
C7A—C8A1.3793 (19)C9D—C10D1.384 (2)
C2A—N1A—C3A120.90 (11)F4B—C9B—C8B119.76 (13)
C2A—N1A—H1A119.5F4B—C9B—C10B120.51 (13)
C3A—N1A—H1A119.5C8B—C9B—C10B119.72 (13)
C2B—N1B—C3B121.05 (11)F5B—C10B—C9B117.01 (12)
C2B—N1B—H1AA119.5F5B—C10B—C5B120.34 (12)
C3B—N1B—H1AA119.5C9B—C10B—C5B122.64 (13)
C2C—N1C—C3C121.35 (11)C2C—C1C—H1BB109.5
C2C—N1C—H1BA119.3C2C—C1C—H1BC109.5
C3C—N1C—H1BA119.3H1BB—C1C—H1BC109.5
C2D—N1D—C3D120.96 (11)C2C—C1C—H1BD109.5
C2D—N1D—H1CA119.5H1BB—C1C—H1BD109.5
C3D—N1D—H1CA119.5H1BC—C1C—H1BD109.5
C2A—C1A—H1B109.5O1C—C2C—N1C121.64 (13)
C2A—C1A—H1C109.5O1C—C2C—C1C121.98 (12)
H1B—C1A—H1C109.5N1C—C2C—C1C116.38 (12)
C2A—C1A—H1D109.5N1C—C3C—C5C111.96 (11)
H1B—C1A—H1D109.5N1C—C3C—C4C110.10 (11)
H1C—C1A—H1D109.5C5C—C3C—C4C109.82 (11)
O1A—C2A—N1A121.45 (13)N1C—C3C—H3BA108.3
O1A—C2A—C1A121.82 (12)C5C—C3C—H3BA108.3
N1A—C2A—C1A116.73 (12)C4C—C3C—H3BA108.3
N1A—C3A—C5A112.61 (11)C3C—C4C—H4BA109.5
N1A—C3A—C4A109.83 (11)C3C—C4C—H4BB109.5
C5A—C3A—C4A109.74 (11)H4BA—C4C—H4BB109.5
N1A—C3A—H3A108.2C3C—C4C—H4BC109.5
C5A—C3A—H3A108.2H4BA—C4C—H4BC109.5
C4A—C3A—H3A108.2H4BB—C4C—H4BC109.5
C3A—C4A—H4A109.5C6C—C5C—C10C116.12 (12)
C3A—C4A—H4B109.5C6C—C5C—C3C122.59 (12)
H4A—C4A—H4B109.5C10C—C5C—C3C121.05 (12)
C3A—C4A—H4C109.5F1C—C6C—C5C120.19 (12)
H4A—C4A—H4C109.5F1C—C6C—C7C117.20 (11)
H4B—C4A—H4C109.5C5C—C6C—C7C122.58 (12)
C10A—C5A—C6A116.07 (12)F2C—C7C—C8C119.76 (12)
C10A—C5A—C3A120.70 (12)F2C—C7C—C6C120.67 (12)
C6A—C5A—C3A122.93 (12)C8C—C7C—C6C119.52 (12)
F1A—C6A—C7A117.60 (12)F3C—C8C—C9C120.32 (12)
F1A—C6A—C5A119.89 (12)F3C—C8C—C7C120.00 (12)
C7A—C6A—C5A122.48 (12)C9C—C8C—C7C119.65 (12)
F2A—C7A—C8A119.78 (12)F4C—C9C—C8C119.58 (12)
F2A—C7A—C6A120.62 (12)F4C—C9C—C10C120.90 (12)
C8A—C7A—C6A119.57 (12)C8C—C9C—C10C119.50 (12)
F3A—C8A—C7A120.35 (12)F5C—C10C—C9C117.61 (11)
F3A—C8A—C9A120.03 (12)F5C—C10C—C5C119.76 (12)
C7A—C8A—C9A119.57 (12)C9C—C10C—C5C122.61 (12)
F4A—C9A—C8A119.52 (12)C2D—C1D—H1CB109.5
F4A—C9A—C10A120.74 (12)C2D—C1D—H1CC109.5
C8A—C9A—C10A119.70 (12)H1CB—C1D—H1CC109.5
F5A—C10A—C9A117.58 (12)C2D—C1D—H1CD109.5
F5A—C10A—C5A119.81 (12)H1CB—C1D—H1CD109.5
C9A—C10A—C5A122.58 (12)H1CC—C1D—H1CD109.5
C2B—C1B—H1AB109.5O1D—C2D—N1D121.68 (13)
C2B—C1B—H1AC109.5O1D—C2D—C1D121.94 (13)
H1AB—C1B—H1AC109.5N1D—C2D—C1D116.37 (12)
C2B—C1B—H1AD109.5N1D—C3D—C5D109.78 (11)
H1AB—C1B—H1AD109.5N1D—C3D—C4D110.45 (11)
H1AC—C1B—H1AD109.5C5D—C3D—C4D113.39 (11)
O1B—C2B—N1B121.89 (13)N1D—C3D—H3CA107.7
O1B—C2B—C1B121.86 (13)C5D—C3D—H3CA107.7
N1B—C2B—C1B116.26 (12)C4D—C3D—H3CA107.7
N1B—C3B—C5B110.00 (11)C3D—C4D—H4CA109.5
N1B—C3B—C4B110.39 (11)C3D—C4D—H4CB109.5
C5B—C3B—C4B113.43 (11)H4CA—C4D—H4CB109.5
N1B—C3B—H3AA107.6C3D—C4D—H4CC109.5
C5B—C3B—H3AA107.6H4CA—C4D—H4CC109.5
C4B—C3B—H3AA107.6H4CB—C4D—H4CC109.5
C3B—C4B—H4AA109.5C10D—C5D—C6D115.57 (13)
C3B—C4B—H4AB109.5C10D—C5D—C3D122.58 (12)
H4AA—C4B—H4AB109.5C6D—C5D—C3D121.82 (12)
C3B—C4B—H4AC109.5F1D—C6D—C7D117.22 (12)
H4AA—C4B—H4AC109.5F1D—C6D—C5D119.88 (12)
H4AB—C4B—H4AC109.5C7D—C6D—C5D122.89 (13)
C10B—C5B—C6B115.69 (13)F2D—C7D—C6D120.17 (13)
C10B—C5B—C3B122.30 (12)F2D—C7D—C8D120.23 (13)
C6B—C5B—C3B122.00 (12)C6D—C7D—C8D119.59 (13)
F1B—C6B—C7B117.28 (12)F3D—C8D—C9D120.46 (13)
F1B—C6B—C5B119.84 (12)F3D—C8D—C7D120.07 (13)
C7B—C6B—C5B122.88 (13)C9D—C8D—C7D119.46 (13)
F2B—C7B—C8B120.15 (13)F4D—C9D—C8D119.73 (13)
F2B—C7B—C6B120.20 (13)F4D—C9D—C10D120.61 (13)
C8B—C7B—C6B119.65 (13)C8D—C9D—C10D119.66 (13)
F3B—C8B—C9B120.43 (13)F5D—C10D—C9D117.09 (12)
F3B—C8B—C7B120.15 (13)F5D—C10D—C5D120.10 (13)
C9B—C8B—C7B119.41 (13)C9D—C10D—C5D122.81 (13)
C3A—N1A—C2A—O1A4.2 (2)C3C—N1C—C2C—O1C0.3 (2)
C3A—N1A—C2A—C1A175.77 (12)C3C—N1C—C2C—C1C179.29 (12)
C2A—N1A—C3A—C5A74.23 (15)C2C—N1C—C3C—C5C81.32 (15)
C2A—N1A—C3A—C4A163.15 (12)C2C—N1C—C3C—C4C156.20 (12)
N1A—C3A—C5A—C10A131.37 (13)N1C—C3C—C5C—C6C47.80 (16)
C4A—C3A—C5A—C10A105.96 (14)C4C—C3C—C5C—C6C74.83 (15)
N1A—C3A—C5A—C6A55.23 (17)N1C—C3C—C5C—C10C138.10 (12)
C4A—C3A—C5A—C6A67.44 (16)C4C—C3C—C5C—C10C99.26 (14)
C10A—C5A—C6A—F1A179.78 (11)C10C—C5C—C6C—F1C177.58 (11)
C3A—C5A—C6A—F1A6.10 (19)C3C—C5C—C6C—F1C3.22 (19)
C10A—C5A—C6A—C7A1.80 (19)C10C—C5C—C6C—C7C0.37 (19)
C3A—C5A—C6A—C7A171.89 (12)C3C—C5C—C6C—C7C174.73 (12)
F1A—C6A—C7A—F2A1.45 (18)F1C—C6C—C7C—F2C1.05 (18)
C5A—C6A—C7A—F2A176.58 (11)C5C—C6C—C7C—F2C179.06 (11)
F1A—C6A—C7A—C8A179.34 (11)F1C—C6C—C7C—C8C176.22 (11)
C5A—C6A—C7A—C8A1.3 (2)C5C—C6C—C7C—C8C1.79 (19)
F2A—C7A—C8A—F3A0.80 (18)F2C—C7C—C8C—F3C0.91 (18)
C6A—C7A—C8A—F3A177.10 (11)C6C—C7C—C8C—F3C176.39 (11)
F2A—C7A—C8A—C9A178.32 (11)F2C—C7C—C8C—C9C178.97 (11)
C6A—C7A—C8A—C9A0.42 (19)C6C—C7C—C8C—C9C1.68 (19)
F3A—C8A—C9A—F4A1.68 (18)F3C—C8C—C9C—F4C0.35 (18)
C7A—C8A—C9A—F4A179.20 (11)C7C—C8C—C9C—F4C178.41 (11)
F3A—C8A—C9A—C10A176.00 (11)F3C—C8C—C9C—C10C177.85 (11)
C7A—C8A—C9A—C10A1.53 (19)C7C—C8C—C9C—C10C0.21 (19)
F4A—C9A—C10A—F5A0.57 (18)F4C—C9C—C10C—F5C1.42 (18)
C8A—C9A—C10A—F5A177.07 (11)C8C—C9C—C10C—F5C179.60 (11)
F4A—C9A—C10A—C5A178.64 (11)F4C—C9C—C10C—C5C176.91 (11)
C8A—C9A—C10A—C5A1.0 (2)C8C—C9C—C10C—C5C1.26 (19)
C6A—C5A—C10A—F5A178.67 (11)C6C—C5C—C10C—F5C179.46 (11)
C3A—C5A—C10A—F5A4.83 (18)C3C—C5C—C10C—F5C5.01 (18)
C6A—C5A—C10A—C9A0.64 (19)C6C—C5C—C10C—C9C1.16 (19)
C3A—C5A—C10A—C9A173.20 (12)C3C—C5C—C10C—C9C173.29 (12)
C3B—N1B—C2B—O1B0.5 (2)C3D—N1D—C2D—O1D3.1 (2)
C3B—N1B—C2B—C1B179.40 (12)C3D—N1D—C2D—C1D176.07 (12)
C2B—N1B—C3B—C5B87.95 (15)C2D—N1D—C3D—C5D84.22 (15)
C2B—N1B—C3B—C4B146.12 (13)C2D—N1D—C3D—C4D150.02 (12)
N1B—C3B—C5B—C10B111.38 (14)N1D—C3D—C5D—C10D111.70 (14)
C4B—C3B—C5B—C10B124.43 (14)C4D—C3D—C5D—C10D124.24 (14)
N1B—C3B—C5B—C6B67.47 (16)N1D—C3D—C5D—C6D66.39 (16)
C4B—C3B—C5B—C6B56.73 (17)C4D—C3D—C5D—C6D57.67 (17)
C10B—C5B—C6B—F1B178.78 (12)C10D—C5D—C6D—F1D178.71 (12)
C3B—C5B—C6B—F1B0.14 (19)C3D—C5D—C6D—F1D0.50 (19)
C10B—C5B—C6B—C7B0.9 (2)C10D—C5D—C6D—C7D1.0 (2)
C3B—C5B—C6B—C7B179.81 (12)C3D—C5D—C6D—C7D179.19 (13)
F1B—C6B—C7B—F2B2.61 (19)F1D—C6D—C7D—F2D2.58 (19)
C5B—C6B—C7B—F2B177.70 (12)C5D—C6D—C7D—F2D177.72 (12)
F1B—C6B—C7B—C8B178.39 (12)F1D—C6D—C7D—C8D178.46 (12)
C5B—C6B—C7B—C8B1.3 (2)C5D—C6D—C7D—C8D1.2 (2)
F2B—C7B—C8B—F3B1.0 (2)F2D—C7D—C8D—F3D0.9 (2)
C6B—C7B—C8B—F3B179.99 (12)C6D—C7D—C8D—F3D179.87 (12)
F2B—C7B—C8B—C9B177.89 (12)F2D—C7D—C8D—C9D177.97 (12)
C6B—C7B—C8B—C9B1.1 (2)C6D—C7D—C8D—C9D1.0 (2)
F3B—C8B—C9B—F4B0.1 (2)F3D—C8D—C9D—F4D0.3 (2)
C7B—C8B—C9B—F4B179.03 (12)C7D—C8D—C9D—F4D179.19 (13)
F3B—C8B—C9B—C10B179.50 (12)F3D—C8D—C9D—C10D179.44 (12)
C7B—C8B—C9B—C10B0.6 (2)C7D—C8D—C9D—C10D0.6 (2)
F4B—C9B—C10B—F5B0.73 (19)F4D—C9D—C10D—F5D0.7 (2)
C8B—C9B—C10B—F5B179.64 (12)C8D—C9D—C10D—F5D179.57 (12)
F4B—C9B—C10B—C5B179.38 (12)F4D—C9D—C10D—C5D179.40 (12)
C8B—C9B—C10B—C5B0.2 (2)C8D—C9D—C10D—C5D0.3 (2)
C6B—C5B—C10B—F5B179.52 (11)C6D—C5D—C10D—F5D179.39 (11)
C3B—C5B—C10B—F5B0.6 (2)C3D—C5D—C10D—F5D1.2 (2)
C6B—C5B—C10B—C9B0.4 (2)C6D—C5D—C10D—C9D0.5 (2)
C3B—C5B—C10B—C9B179.28 (12)C3D—C5D—C10D—C9D178.73 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1Di0.882.022.8443 (15)156
N1B—H1AA···O1A0.882.032.8855 (15)165
N1C—H1BA···O1Bii0.881.962.8380 (15)172
N1D—H1CA···O1C0.882.002.8569 (15)164
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC10H8F5NO
Mr253.17
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.4129 (5), 12.2875 (8), 23.5594 (15)
α, β, γ (°)77.694 (2), 82.070 (2), 89.936 (2)
V3)2075.7 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.17
Crystal size (mm)0.49 × 0.38 × 0.26
Data collection
DiffractometerBruker CCD-1000 area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2003)
Tmin, Tmax0.923, 0.958
No. of measured, independent and
observed [I > 2σ(I)] reflections
30498, 8472, 6949
Rint0.024
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.089, 1.04
No. of reflections8472
No. of parameters621
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.23

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SAINT, SHELXTL (Bruker, 2003), SHELXTL.

Selected geometric parameters (Å, º) top
O1A—C2A1.2352 (17)N1B—C2B1.3406 (18)
O1B—C2B1.2307 (17)N1B—C3B1.4607 (17)
O1C—C2C1.2314 (17)N1C—C2C1.3384 (17)
O1D—C2D1.2303 (17)N1C—C3C1.4564 (17)
N1A—C2A1.3374 (17)N1D—C2D1.3433 (18)
N1A—C3A1.4570 (17)N1D—C3D1.4581 (17)
C2A—N1A—C3A120.90 (11)C2C—N1C—C3C121.35 (11)
C2B—N1B—C3B121.05 (11)C2D—N1D—C3D120.96 (11)
C3A—N1A—C2A—O1A4.2 (2)C3C—N1C—C2C—O1C0.3 (2)
C3A—N1A—C2A—C1A175.77 (12)C3C—N1C—C2C—C1C179.29 (12)
C2A—N1A—C3A—C5A74.23 (15)C2C—N1C—C3C—C5C81.32 (15)
C2A—N1A—C3A—C4A163.15 (12)C2C—N1C—C3C—C4C156.20 (12)
C3B—N1B—C2B—O1B0.5 (2)C3D—N1D—C2D—O1D3.1 (2)
C3B—N1B—C2B—C1B179.40 (12)C3D—N1D—C2D—C1D176.07 (12)
C2B—N1B—C3B—C5B87.95 (15)C2D—N1D—C3D—C5D84.22 (15)
C2B—N1B—C3B—C4B146.12 (13)C2D—N1D—C3D—C4D150.02 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1Di0.882.022.8443 (15)156
N1B—H1AA···O1A0.882.032.8855 (15)165
N1C—H1BA···O1Bii0.881.962.8380 (15)172
N1D—H1CA···O1C0.882.002.8569 (15)164
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.
 

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