N-[1-(Penta­fluoro­phenyl)­ethyl]­acetamide

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.

S1. Comment

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 π–π 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 (A–D) 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 A–D 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 A–D 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—C═O unit due to the n(N1) → π*(C2═O1) donation is more prominent in the experimental data [N1—C2 = 1.340 (3) and C2═O1 = 1.232 (2) Å] than in the theoretical model [N1—C2 = 1.37 and C2═O1 = 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 C═O 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 C2═O1 to be 1.1 and 1.9, respectively.

S2. Experimental

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.

S3. Refinement

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 U_iso(H) = 1.2 (for N1 and C3) or 1.5 (for Me groups) times U_eq(parent).

Computing details

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

	Fig. 1. The molecular structure of (II), showing the four symmetry-independent molecules (suffixes A–D). 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.
	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.
	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

Crystal data

C10H8F5NO	Z = 8
Mr = 253.17	F(000) = 1024
Triclinic, P1	Dx = 1.620 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4129 (5) Å	Cell parameters from 13370 reflections
b = 12.2875 (8) Å	θ = 2.7–26.4°
c = 23.5594 (15) Å	µ = 0.17 mm^−1
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) Å^3

Data collection

Bruker CCD-1000 area-detector diffractometer	8472 independent reflections
Radiation source: fine-focus sealed tube	6949 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
0.30° ω scans	θmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −9→9
Tmin = 0.923, Tmax = 0.958	k = −15→15
30498 measured reflections	l = −29→29

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0417P)^2 + 0.8749P] where P = (Fo^2 + 2Fc^2)/3
8472 reflections	(Δ/σ)max = 0.001
621 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1A	1.06643 (10)	0.50505 (7)	0.40483 (4)	0.02252 (18)
F2A	0.97022 (11)	0.35949 (7)	0.50744 (3)	0.02302 (18)
F3A	0.61370 (11)	0.29898 (7)	0.54514 (3)	0.02392 (18)
F4A	0.35502 (10)	0.38302 (7)	0.47850 (4)	0.02346 (18)
F5A	0.44685 (10)	0.53412 (7)	0.37763 (4)	0.02226 (18)
F1B	0.69967 (12)	0.51779 (7)	0.12690 (4)	0.02687 (19)
F2B	0.55073 (12)	0.67126 (7)	0.05021 (4)	0.0284 (2)
F3B	0.24491 (12)	0.62035 (8)	0.00789 (4)	0.0330 (2)
F4B	0.10046 (12)	0.40931 (8)	0.04012 (4)	0.0345 (2)
F5B	0.25184 (11)	0.25286 (7)	0.11489 (4)	0.02624 (19)
F1C	1.14838 (10)	0.02785 (7)	0.38191 (3)	0.02067 (17)
F2C	1.15477 (10)	−0.12271 (7)	0.48251 (4)	0.02213 (18)
F3C	0.83890 (11)	−0.20761 (7)	0.54984 (3)	0.02262 (18)
F4C	0.51429 (10)	−0.14774 (7)	0.51308 (3)	0.02189 (18)
F5C	0.50512 (10)	−0.00369 (7)	0.40986 (3)	0.02160 (18)
F1D	0.69529 (12)	0.01565 (7)	0.12802 (4)	0.02705 (19)
F2D	0.54576 (12)	0.16749 (7)	0.05083 (4)	0.0288 (2)
F3D	0.24210 (13)	0.11426 (8)	0.00802 (4)	0.0344 (2)
F4D	0.09986 (12)	−0.09733 (8)	0.04077 (4)	0.0358 (2)
F5D	0.25207 (11)	−0.25233 (7)	0.11628 (4)	0.02640 (19)
O1A	0.77024 (13)	0.47169 (8)	0.26288 (4)	0.0231 (2)
O1B	0.27619 (14)	0.22532 (10)	0.25183 (5)	0.0322 (3)
O1C	0.77357 (14)	−0.03317 (8)	0.26310 (4)	0.0250 (2)
O1D	0.26714 (14)	−0.26742 (9)	0.25192 (5)	0.0301 (2)
N1A	0.95159 (15)	0.59065 (9)	0.29087 (5)	0.0191 (2)
H1A	1.0615	0.6205	0.2874	0.023*
N1B	0.54684 (15)	0.31722 (9)	0.22434 (5)	0.0185 (2)
H1AA	0.6315	0.3572	0.2340	0.022*
N1C	0.95098 (15)	0.09232 (9)	0.28767 (5)	0.0188 (2)
H1BA	1.0551	0.1304	0.2799	0.023*
N1D	0.54369 (16)	−0.18251 (9)	0.22565 (5)	0.0190 (2)
H1CA	0.6310	−0.1453	0.2358	0.023*
C1A	1.0748 (2)	0.50318 (13)	0.21144 (6)	0.0258 (3)
H1B	1.1047	0.4242	0.2182	0.039*
H1C	1.1817	0.5476	0.2142	0.039*
H1D	1.0389	0.5267	0.1723	0.039*
C2A	0.91969 (19)	0.52021 (11)	0.25700 (6)	0.0187 (3)
C3A	0.80692 (18)	0.61858 (11)	0.33344 (6)	0.0189 (3)
H3A	0.6952	0.6343	0.3140	0.023*
C4A	0.8617 (2)	0.72385 (12)	0.35244 (7)	0.0263 (3)
H4A	0.8843	0.7855	0.3180	0.039*
H4B	0.9726	0.7107	0.3709	0.039*
H4C	0.7631	0.7429	0.3806	0.039*
C5A	0.76033 (18)	0.52429 (11)	0.38713 (6)	0.0166 (3)
C6A	0.88934 (17)	0.47591 (11)	0.42151 (6)	0.0177 (3)
C7A	0.84258 (18)	0.39995 (11)	0.47412 (6)	0.0183 (3)
C8A	0.66213 (18)	0.36852 (11)	0.49325 (6)	0.0179 (3)
C9A	0.53068 (18)	0.41262 (11)	0.45952 (6)	0.0182 (3)
C10A	0.58058 (18)	0.48965 (11)	0.40773 (6)	0.0171 (3)
C1B	0.3872 (2)	0.31577 (14)	0.32105 (6)	0.0298 (3)
H1AB	0.2769	0.3581	0.3273	0.045*
H1AC	0.4946	0.3622	0.3210	0.045*
H1AD	0.3833	0.2490	0.3526	0.045*
C2B	0.39776 (19)	0.28200 (12)	0.26312 (6)	0.0216 (3)
C3B	0.57094 (18)	0.29032 (11)	0.16634 (6)	0.0183 (3)
H3AA	0.5049	0.2177	0.1699	0.022*
C4B	0.77208 (19)	0.27450 (12)	0.14615 (6)	0.0225 (3)
H4AA	0.8163	0.2112	0.1731	0.034*
H4AB	0.8423	0.3421	0.1460	0.034*
H4AC	0.7868	0.2600	0.1065	0.034*
C5B	0.48369 (18)	0.37840 (11)	0.12342 (6)	0.0182 (3)
C6B	0.55220 (19)	0.48749 (11)	0.10580 (6)	0.0195 (3)
C7B	0.4750 (2)	0.56842 (11)	0.06717 (6)	0.0219 (3)
C8B	0.3209 (2)	0.54252 (12)	0.04537 (6)	0.0234 (3)
C9B	0.24824 (19)	0.43548 (13)	0.06175 (6)	0.0235 (3)
C10B	0.32946 (19)	0.35560 (11)	0.10027 (6)	0.0199 (3)
C1C	1.0663 (2)	0.01226 (12)	0.20488 (6)	0.0237 (3)
H1BB	1.1058	−0.0649	0.2101	0.036*
H1BC	1.1699	0.0614	0.2054	0.036*
H1BD	1.0199	0.0343	0.1672	0.036*
C2C	0.91760 (18)	0.02164 (11)	0.25403 (6)	0.0183 (3)
C3C	0.81841 (18)	0.10743 (11)	0.33688 (6)	0.0180 (3)
H3BA	0.6939	0.1050	0.3253	0.022*
C4C	0.8494 (2)	0.22109 (11)	0.35083 (6)	0.0228 (3)
H4BA	0.8358	0.2798	0.3165	0.034*
H4BB	0.9725	0.2260	0.3610	0.034*
H4BC	0.7597	0.2304	0.3840	0.034*
C5C	0.82652 (18)	0.01580 (11)	0.39142 (6)	0.0162 (3)
C6C	0.98873 (17)	−0.01730 (11)	0.41187 (6)	0.0165 (3)
C7C	0.99507 (18)	−0.09414 (11)	0.46391 (6)	0.0177 (3)
C8C	0.83463 (19)	−0.13805 (11)	0.49805 (6)	0.0177 (3)
C9C	0.67011 (17)	−0.10710 (11)	0.47922 (6)	0.0176 (3)
C10C	0.66826 (17)	−0.03215 (11)	0.42642 (6)	0.0169 (3)
C1D	0.3735 (2)	−0.17005 (14)	0.31920 (6)	0.0286 (3)
H1CB	0.3439	−0.2329	0.3527	0.043*
H1CC	0.2767	−0.1157	0.3195	0.043*
H1CD	0.4894	−0.1346	0.3220	0.043*
C2D	0.38942 (19)	−0.21133 (11)	0.26321 (6)	0.0203 (3)
C3D	0.56865 (18)	−0.21205 (11)	0.16838 (6)	0.0186 (3)
H3CA	0.5028	−0.2850	0.1727	0.022*
C4D	0.77017 (19)	−0.22809 (12)	0.14862 (6)	0.0230 (3)
H4CA	0.8142	−0.2907	0.1760	0.034*
H4CB	0.8401	−0.1601	0.1480	0.034*
H4CC	0.7855	−0.2438	0.1092	0.034*
C5D	0.48162 (18)	−0.12537 (11)	0.12463 (6)	0.0183 (3)
C6D	0.54882 (19)	−0.01582 (12)	0.10681 (6)	0.0200 (3)
C7D	0.4712 (2)	0.06430 (12)	0.06789 (6)	0.0225 (3)
C8D	0.3183 (2)	0.03716 (12)	0.04591 (6)	0.0240 (3)
C9D	0.24684 (19)	−0.07019 (13)	0.06250 (6)	0.0242 (3)
C10D	0.32836 (19)	−0.14905 (12)	0.10133 (6)	0.0206 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1A	0.0122 (4)	0.0277 (4)	0.0273 (4)	−0.0017 (3)	−0.0017 (3)	−0.0059 (3)
F2A	0.0223 (4)	0.0251 (4)	0.0237 (4)	0.0048 (3)	−0.0094 (3)	−0.0060 (3)
F3A	0.0301 (5)	0.0211 (4)	0.0185 (4)	−0.0019 (3)	0.0010 (3)	−0.0025 (3)
F4A	0.0138 (4)	0.0248 (4)	0.0305 (4)	−0.0044 (3)	0.0031 (3)	−0.0072 (4)
F5A	0.0148 (4)	0.0253 (4)	0.0273 (4)	0.0023 (3)	−0.0066 (3)	−0.0048 (3)
F1B	0.0303 (5)	0.0206 (4)	0.0307 (5)	−0.0067 (3)	−0.0123 (4)	−0.0028 (4)
F2B	0.0388 (5)	0.0174 (4)	0.0272 (4)	−0.0024 (4)	−0.0060 (4)	0.0000 (3)
F3B	0.0351 (5)	0.0345 (5)	0.0264 (5)	0.0067 (4)	−0.0102 (4)	0.0042 (4)
F4B	0.0245 (5)	0.0454 (6)	0.0329 (5)	−0.0054 (4)	−0.0134 (4)	−0.0006 (4)
F5B	0.0246 (4)	0.0251 (4)	0.0283 (4)	−0.0087 (3)	−0.0055 (3)	−0.0029 (4)
F1C	0.0126 (4)	0.0239 (4)	0.0242 (4)	−0.0022 (3)	−0.0009 (3)	−0.0033 (3)
F2C	0.0165 (4)	0.0229 (4)	0.0279 (4)	0.0033 (3)	−0.0085 (3)	−0.0040 (3)
F3C	0.0276 (4)	0.0213 (4)	0.0178 (4)	−0.0006 (3)	−0.0040 (3)	−0.0009 (3)
F4C	0.0172 (4)	0.0237 (4)	0.0231 (4)	−0.0046 (3)	0.0031 (3)	−0.0050 (3)
F5C	0.0121 (4)	0.0273 (4)	0.0261 (4)	0.0006 (3)	−0.0048 (3)	−0.0060 (3)
F1D	0.0302 (5)	0.0207 (4)	0.0316 (5)	−0.0067 (3)	−0.0131 (4)	−0.0030 (4)
F2D	0.0386 (5)	0.0183 (4)	0.0278 (4)	−0.0022 (4)	−0.0062 (4)	0.0002 (3)
F3D	0.0345 (5)	0.0378 (5)	0.0276 (5)	0.0066 (4)	−0.0111 (4)	0.0042 (4)
F4D	0.0248 (5)	0.0489 (6)	0.0334 (5)	−0.0066 (4)	−0.0136 (4)	−0.0023 (4)
F5D	0.0245 (4)	0.0259 (4)	0.0288 (5)	−0.0087 (3)	−0.0048 (3)	−0.0052 (4)
O1A	0.0232 (5)	0.0221 (5)	0.0239 (5)	−0.0062 (4)	−0.0035 (4)	−0.0045 (4)
O1B	0.0252 (6)	0.0414 (7)	0.0302 (6)	−0.0165 (5)	0.0029 (4)	−0.0122 (5)
O1C	0.0247 (5)	0.0255 (5)	0.0255 (5)	−0.0090 (4)	−0.0035 (4)	−0.0073 (4)
O1D	0.0241 (5)	0.0375 (6)	0.0284 (6)	−0.0136 (5)	0.0009 (4)	−0.0093 (5)
N1A	0.0160 (6)	0.0213 (6)	0.0194 (6)	−0.0047 (5)	−0.0003 (4)	−0.0046 (5)
N1B	0.0180 (6)	0.0199 (6)	0.0170 (6)	−0.0058 (4)	−0.0025 (4)	−0.0029 (4)
N1C	0.0156 (6)	0.0220 (6)	0.0181 (6)	−0.0050 (5)	−0.0016 (4)	−0.0036 (5)
N1D	0.0196 (6)	0.0203 (6)	0.0176 (6)	−0.0050 (5)	−0.0040 (4)	−0.0042 (5)
C1A	0.0274 (8)	0.0260 (8)	0.0234 (7)	−0.0016 (6)	0.0014 (6)	−0.0071 (6)
C2A	0.0216 (7)	0.0164 (6)	0.0166 (6)	−0.0010 (5)	−0.0038 (5)	0.0009 (5)
C3A	0.0171 (7)	0.0187 (7)	0.0201 (7)	−0.0003 (5)	−0.0014 (5)	−0.0032 (5)
C4A	0.0322 (8)	0.0182 (7)	0.0271 (8)	−0.0018 (6)	0.0009 (6)	−0.0053 (6)
C5A	0.0170 (6)	0.0153 (6)	0.0186 (6)	−0.0002 (5)	−0.0013 (5)	−0.0067 (5)
C6A	0.0135 (6)	0.0185 (7)	0.0222 (7)	−0.0017 (5)	−0.0014 (5)	−0.0078 (5)
C7A	0.0189 (7)	0.0181 (7)	0.0207 (7)	0.0037 (5)	−0.0063 (5)	−0.0081 (5)
C8A	0.0223 (7)	0.0152 (6)	0.0161 (6)	−0.0012 (5)	0.0005 (5)	−0.0050 (5)
C9A	0.0142 (6)	0.0173 (7)	0.0237 (7)	−0.0029 (5)	0.0018 (5)	−0.0088 (5)
C10A	0.0167 (6)	0.0163 (6)	0.0206 (7)	0.0026 (5)	−0.0047 (5)	−0.0079 (5)
C1B	0.0254 (8)	0.0406 (9)	0.0232 (8)	−0.0085 (7)	0.0014 (6)	−0.0093 (7)
C2B	0.0196 (7)	0.0227 (7)	0.0212 (7)	−0.0035 (6)	−0.0019 (5)	−0.0025 (6)
C3B	0.0192 (7)	0.0172 (7)	0.0183 (6)	−0.0027 (5)	−0.0026 (5)	−0.0034 (5)
C4B	0.0216 (7)	0.0223 (7)	0.0228 (7)	0.0018 (6)	−0.0025 (6)	−0.0034 (6)
C5B	0.0191 (7)	0.0201 (7)	0.0154 (6)	0.0001 (5)	0.0001 (5)	−0.0053 (5)
C6B	0.0206 (7)	0.0208 (7)	0.0183 (6)	−0.0008 (5)	−0.0035 (5)	−0.0061 (5)
C7B	0.0279 (7)	0.0176 (7)	0.0188 (7)	0.0000 (6)	0.0002 (6)	−0.0031 (5)
C8B	0.0254 (7)	0.0271 (8)	0.0161 (7)	0.0068 (6)	−0.0030 (5)	−0.0009 (6)
C9B	0.0180 (7)	0.0341 (8)	0.0189 (7)	−0.0003 (6)	−0.0029 (5)	−0.0063 (6)
C10B	0.0198 (7)	0.0206 (7)	0.0181 (7)	−0.0033 (5)	0.0012 (5)	−0.0043 (5)
C1C	0.0252 (7)	0.0246 (7)	0.0211 (7)	−0.0008 (6)	−0.0015 (6)	−0.0053 (6)
C2C	0.0204 (7)	0.0161 (6)	0.0178 (6)	−0.0002 (5)	−0.0060 (5)	−0.0002 (5)
C3C	0.0159 (6)	0.0191 (7)	0.0193 (7)	−0.0003 (5)	−0.0043 (5)	−0.0035 (5)
C4C	0.0255 (7)	0.0177 (7)	0.0255 (7)	0.0009 (6)	−0.0056 (6)	−0.0040 (6)
C5C	0.0175 (6)	0.0143 (6)	0.0183 (6)	0.0000 (5)	−0.0026 (5)	−0.0065 (5)
C6C	0.0136 (6)	0.0164 (6)	0.0200 (6)	−0.0016 (5)	0.0001 (5)	−0.0065 (5)
C7C	0.0160 (6)	0.0171 (6)	0.0226 (7)	0.0028 (5)	−0.0059 (5)	−0.0081 (5)
C8C	0.0227 (7)	0.0141 (6)	0.0168 (6)	−0.0001 (5)	−0.0034 (5)	−0.0043 (5)
C9C	0.0142 (6)	0.0174 (7)	0.0214 (7)	−0.0035 (5)	0.0018 (5)	−0.0077 (5)
C10C	0.0131 (6)	0.0182 (6)	0.0217 (7)	0.0013 (5)	−0.0040 (5)	−0.0085 (5)
C1D	0.0271 (8)	0.0368 (9)	0.0215 (7)	−0.0050 (7)	−0.0016 (6)	−0.0065 (6)
C2D	0.0202 (7)	0.0191 (7)	0.0205 (7)	−0.0014 (5)	−0.0044 (5)	−0.0005 (5)
C3D	0.0195 (7)	0.0168 (7)	0.0193 (7)	−0.0027 (5)	−0.0026 (5)	−0.0038 (5)
C4D	0.0210 (7)	0.0225 (7)	0.0249 (7)	0.0011 (6)	−0.0029 (6)	−0.0041 (6)
C5D	0.0188 (7)	0.0207 (7)	0.0160 (6)	0.0005 (5)	−0.0009 (5)	−0.0060 (5)
C6D	0.0209 (7)	0.0223 (7)	0.0185 (7)	−0.0011 (5)	−0.0042 (5)	−0.0069 (5)
C7D	0.0274 (7)	0.0198 (7)	0.0194 (7)	0.0003 (6)	−0.0002 (6)	−0.0041 (5)
C8D	0.0248 (7)	0.0291 (8)	0.0168 (7)	0.0061 (6)	−0.0038 (5)	−0.0015 (6)
C9D	0.0182 (7)	0.0364 (9)	0.0192 (7)	−0.0009 (6)	−0.0033 (5)	−0.0083 (6)
C10D	0.0201 (7)	0.0223 (7)	0.0193 (7)	−0.0034 (5)	0.0010 (5)	−0.0066 (6)

Geometric parameters (Å, º)

F1A—C6A	1.3434 (15)	C8A—C9A	1.3797 (19)
F2A—C7A	1.3402 (15)	C9A—C10A	1.3804 (19)
F3A—C8A	1.3371 (15)	C1B—C2B	1.501 (2)
F4A—C9A	1.3412 (15)	C1B—H1AB	0.9800
F5A—C10A	1.3460 (15)	C1B—H1AC	0.9800
F1B—C6B	1.3456 (15)	C1B—H1AD	0.9800
F2B—C7B	1.3403 (16)	C3B—C5B	1.5246 (19)
F3B—C8B	1.3372 (16)	C3B—C4B	1.5266 (19)
F4B—C9B	1.3372 (16)	C3B—H3AA	1.0000
F5B—C10B	1.3435 (16)	C4B—H4AA	0.9800
F1C—C6C	1.3456 (15)	C4B—H4AB	0.9800
F2C—C7C	1.3391 (15)	C4B—H4AC	0.9800
F3C—C8C	1.3365 (15)	C5B—C10B	1.3860 (19)
F4C—C9C	1.3406 (15)	C5B—C6B	1.3904 (19)
F5C—C10C	1.3447 (15)	C6B—C7B	1.379 (2)
F1D—C6D	1.3458 (15)	C7B—C8B	1.379 (2)
F2D—C7D	1.3408 (16)	C8B—C9B	1.377 (2)
F3D—C8D	1.3382 (16)	C9B—C10B	1.385 (2)
F4D—C9D	1.3371 (16)	C1C—C2C	1.5078 (19)
F5D—C10D	1.3455 (16)	C1C—H1BB	0.9800
O1A—C2A	1.2352 (17)	C1C—H1BC	0.9800
O1B—C2B	1.2307 (17)	C1C—H1BD	0.9800
O1C—C2C	1.2314 (17)	C3C—C5C	1.5255 (18)
O1D—C2D	1.2303 (17)	C3C—C4C	1.5259 (18)
N1A—C2A	1.3374 (17)	C3C—H3BA	1.0000
N1A—C3A	1.4570 (17)	C4C—H4BA	0.9800
N1A—H1A	0.8800	C4C—H4BB	0.9800
N1B—C2B	1.3406 (18)	C4C—H4BC	0.9800
N1B—C3B	1.4607 (17)	C5C—C6C	1.3851 (19)
N1B—H1AA	0.8800	C5C—C10C	1.3895 (19)
N1C—C2C	1.3384 (17)	C6C—C7C	1.3853 (19)
N1C—C3C	1.4564 (17)	C7C—C8C	1.3803 (19)
N1C—H1BA	0.8800	C8C—C9C	1.3803 (19)
N1D—C2D	1.3433 (18)	C9C—C10C	1.3828 (19)
N1D—C3D	1.4581 (17)	C1D—C2D	1.501 (2)
N1D—H1CA	0.8800	C1D—H1CB	0.9800
C1A—C2A	1.5076 (19)	C1D—H1CC	0.9800
C1A—H1B	0.9800	C1D—H1CD	0.9800
C1A—H1C	0.9800	C3D—C5D	1.5255 (19)
C1A—H1D	0.9800	C3D—C4D	1.5276 (19)
C3A—C5A	1.5223 (18)	C3D—H3CA	1.0000
C3A—C4A	1.5286 (19)	C4D—H4CA	0.9800
C3A—H3A	1.0000	C4D—H4CB	0.9800
C4A—H4A	0.9800	C4D—H4CC	0.9800
C4A—H4B	0.9800	C5D—C10D	1.3847 (19)
C4A—H4C	0.9800	C5D—C6D	1.3925 (19)
C5A—C10A	1.3881 (19)	C6D—C7D	1.378 (2)
C5A—C6A	1.3896 (19)	C7D—C8D	1.379 (2)
C6A—C7A	1.3845 (19)	C8D—C9D	1.378 (2)
C7A—C8A	1.3793 (19)	C9D—C10D	1.384 (2)
C2A—N1A—C3A	120.90 (11)	F4B—C9B—C8B	119.76 (13)
C2A—N1A—H1A	119.5	F4B—C9B—C10B	120.51 (13)
C3A—N1A—H1A	119.5	C8B—C9B—C10B	119.72 (13)
C2B—N1B—C3B	121.05 (11)	F5B—C10B—C9B	117.01 (12)
C2B—N1B—H1AA	119.5	F5B—C10B—C5B	120.34 (12)
C3B—N1B—H1AA	119.5	C9B—C10B—C5B	122.64 (13)
C2C—N1C—C3C	121.35 (11)	C2C—C1C—H1BB	109.5
C2C—N1C—H1BA	119.3	C2C—C1C—H1BC	109.5
C3C—N1C—H1BA	119.3	H1BB—C1C—H1BC	109.5
C2D—N1D—C3D	120.96 (11)	C2C—C1C—H1BD	109.5
C2D—N1D—H1CA	119.5	H1BB—C1C—H1BD	109.5
C3D—N1D—H1CA	119.5	H1BC—C1C—H1BD	109.5
C2A—C1A—H1B	109.5	O1C—C2C—N1C	121.64 (13)
C2A—C1A—H1C	109.5	O1C—C2C—C1C	121.98 (12)
H1B—C1A—H1C	109.5	N1C—C2C—C1C	116.38 (12)
C2A—C1A—H1D	109.5	N1C—C3C—C5C	111.96 (11)
H1B—C1A—H1D	109.5	N1C—C3C—C4C	110.10 (11)
H1C—C1A—H1D	109.5	C5C—C3C—C4C	109.82 (11)
O1A—C2A—N1A	121.45 (13)	N1C—C3C—H3BA	108.3
O1A—C2A—C1A	121.82 (12)	C5C—C3C—H3BA	108.3
N1A—C2A—C1A	116.73 (12)	C4C—C3C—H3BA	108.3
N1A—C3A—C5A	112.61 (11)	C3C—C4C—H4BA	109.5
N1A—C3A—C4A	109.83 (11)	C3C—C4C—H4BB	109.5
C5A—C3A—C4A	109.74 (11)	H4BA—C4C—H4BB	109.5
N1A—C3A—H3A	108.2	C3C—C4C—H4BC	109.5
C5A—C3A—H3A	108.2	H4BA—C4C—H4BC	109.5
C4A—C3A—H3A	108.2	H4BB—C4C—H4BC	109.5
C3A—C4A—H4A	109.5	C6C—C5C—C10C	116.12 (12)
C3A—C4A—H4B	109.5	C6C—C5C—C3C	122.59 (12)
H4A—C4A—H4B	109.5	C10C—C5C—C3C	121.05 (12)
C3A—C4A—H4C	109.5	F1C—C6C—C5C	120.19 (12)
H4A—C4A—H4C	109.5	F1C—C6C—C7C	117.20 (11)
H4B—C4A—H4C	109.5	C5C—C6C—C7C	122.58 (12)
C10A—C5A—C6A	116.07 (12)	F2C—C7C—C8C	119.76 (12)
C10A—C5A—C3A	120.70 (12)	F2C—C7C—C6C	120.67 (12)
C6A—C5A—C3A	122.93 (12)	C8C—C7C—C6C	119.52 (12)
F1A—C6A—C7A	117.60 (12)	F3C—C8C—C9C	120.32 (12)
F1A—C6A—C5A	119.89 (12)	F3C—C8C—C7C	120.00 (12)
C7A—C6A—C5A	122.48 (12)	C9C—C8C—C7C	119.65 (12)
F2A—C7A—C8A	119.78 (12)	F4C—C9C—C8C	119.58 (12)
F2A—C7A—C6A	120.62 (12)	F4C—C9C—C10C	120.90 (12)
C8A—C7A—C6A	119.57 (12)	C8C—C9C—C10C	119.50 (12)
F3A—C8A—C7A	120.35 (12)	F5C—C10C—C9C	117.61 (11)
F3A—C8A—C9A	120.03 (12)	F5C—C10C—C5C	119.76 (12)
C7A—C8A—C9A	119.57 (12)	C9C—C10C—C5C	122.61 (12)
F4A—C9A—C8A	119.52 (12)	C2D—C1D—H1CB	109.5
F4A—C9A—C10A	120.74 (12)	C2D—C1D—H1CC	109.5
C8A—C9A—C10A	119.70 (12)	H1CB—C1D—H1CC	109.5
F5A—C10A—C9A	117.58 (12)	C2D—C1D—H1CD	109.5
F5A—C10A—C5A	119.81 (12)	H1CB—C1D—H1CD	109.5
C9A—C10A—C5A	122.58 (12)	H1CC—C1D—H1CD	109.5
C2B—C1B—H1AB	109.5	O1D—C2D—N1D	121.68 (13)
C2B—C1B—H1AC	109.5	O1D—C2D—C1D	121.94 (13)
H1AB—C1B—H1AC	109.5	N1D—C2D—C1D	116.37 (12)
C2B—C1B—H1AD	109.5	N1D—C3D—C5D	109.78 (11)
H1AB—C1B—H1AD	109.5	N1D—C3D—C4D	110.45 (11)
H1AC—C1B—H1AD	109.5	C5D—C3D—C4D	113.39 (11)
O1B—C2B—N1B	121.89 (13)	N1D—C3D—H3CA	107.7
O1B—C2B—C1B	121.86 (13)	C5D—C3D—H3CA	107.7
N1B—C2B—C1B	116.26 (12)	C4D—C3D—H3CA	107.7
N1B—C3B—C5B	110.00 (11)	C3D—C4D—H4CA	109.5
N1B—C3B—C4B	110.39 (11)	C3D—C4D—H4CB	109.5
C5B—C3B—C4B	113.43 (11)	H4CA—C4D—H4CB	109.5
N1B—C3B—H3AA	107.6	C3D—C4D—H4CC	109.5
C5B—C3B—H3AA	107.6	H4CA—C4D—H4CC	109.5
C4B—C3B—H3AA	107.6	H4CB—C4D—H4CC	109.5
C3B—C4B—H4AA	109.5	C10D—C5D—C6D	115.57 (13)
C3B—C4B—H4AB	109.5	C10D—C5D—C3D	122.58 (12)
H4AA—C4B—H4AB	109.5	C6D—C5D—C3D	121.82 (12)
C3B—C4B—H4AC	109.5	F1D—C6D—C7D	117.22 (12)
H4AA—C4B—H4AC	109.5	F1D—C6D—C5D	119.88 (12)
H4AB—C4B—H4AC	109.5	C7D—C6D—C5D	122.89 (13)
C10B—C5B—C6B	115.69 (13)	F2D—C7D—C6D	120.17 (13)
C10B—C5B—C3B	122.30 (12)	F2D—C7D—C8D	120.23 (13)
C6B—C5B—C3B	122.00 (12)	C6D—C7D—C8D	119.59 (13)
F1B—C6B—C7B	117.28 (12)	F3D—C8D—C9D	120.46 (13)
F1B—C6B—C5B	119.84 (12)	F3D—C8D—C7D	120.07 (13)
C7B—C6B—C5B	122.88 (13)	C9D—C8D—C7D	119.46 (13)
F2B—C7B—C8B	120.15 (13)	F4D—C9D—C8D	119.73 (13)
F2B—C7B—C6B	120.20 (13)	F4D—C9D—C10D	120.61 (13)
C8B—C7B—C6B	119.65 (13)	C8D—C9D—C10D	119.66 (13)
F3B—C8B—C9B	120.43 (13)	F5D—C10D—C9D	117.09 (12)
F3B—C8B—C7B	120.15 (13)	F5D—C10D—C5D	120.10 (13)
C9B—C8B—C7B	119.41 (13)	C9D—C10D—C5D	122.81 (13)
C3A—N1A—C2A—O1A	−4.2 (2)	C3C—N1C—C2C—O1C	0.3 (2)
C3A—N1A—C2A—C1A	175.77 (12)	C3C—N1C—C2C—C1C	−179.29 (12)
C2A—N1A—C3A—C5A	74.23 (15)	C2C—N1C—C3C—C5C	81.32 (15)
C2A—N1A—C3A—C4A	−163.15 (12)	C2C—N1C—C3C—C4C	−156.20 (12)
N1A—C3A—C5A—C10A	−131.37 (13)	N1C—C3C—C5C—C6C	47.80 (16)
C4A—C3A—C5A—C10A	105.96 (14)	C4C—C3C—C5C—C6C	−74.83 (15)
N1A—C3A—C5A—C6A	55.23 (17)	N1C—C3C—C5C—C10C	−138.10 (12)
C4A—C3A—C5A—C6A	−67.44 (16)	C4C—C3C—C5C—C10C	99.26 (14)
C10A—C5A—C6A—F1A	−179.78 (11)	C10C—C5C—C6C—F1C	−177.58 (11)
C3A—C5A—C6A—F1A	−6.10 (19)	C3C—C5C—C6C—F1C	−3.22 (19)
C10A—C5A—C6A—C7A	−1.80 (19)	C10C—C5C—C6C—C7C	0.37 (19)
C3A—C5A—C6A—C7A	171.89 (12)	C3C—C5C—C6C—C7C	174.73 (12)
F1A—C6A—C7A—F2A	1.45 (18)	F1C—C6C—C7C—F2C	−1.05 (18)
C5A—C6A—C7A—F2A	−176.58 (11)	C5C—C6C—C7C—F2C	−179.06 (11)
F1A—C6A—C7A—C8A	179.34 (11)	F1C—C6C—C7C—C8C	176.22 (11)
C5A—C6A—C7A—C8A	1.3 (2)	C5C—C6C—C7C—C8C	−1.79 (19)
F2A—C7A—C8A—F3A	0.80 (18)	F2C—C7C—C8C—F3C	0.91 (18)
C6A—C7A—C8A—F3A	−177.10 (11)	C6C—C7C—C8C—F3C	−176.39 (11)
F2A—C7A—C8A—C9A	178.32 (11)	F2C—C7C—C8C—C9C	178.97 (11)
C6A—C7A—C8A—C9A	0.42 (19)	C6C—C7C—C8C—C9C	1.68 (19)
F3A—C8A—C9A—F4A	−1.68 (18)	F3C—C8C—C9C—F4C	−0.35 (18)
C7A—C8A—C9A—F4A	−179.20 (11)	C7C—C8C—C9C—F4C	−178.41 (11)
F3A—C8A—C9A—C10A	176.00 (11)	F3C—C8C—C9C—C10C	177.85 (11)
C7A—C8A—C9A—C10A	−1.53 (19)	C7C—C8C—C9C—C10C	−0.21 (19)
F4A—C9A—C10A—F5A	0.57 (18)	F4C—C9C—C10C—F5C	−1.42 (18)
C8A—C9A—C10A—F5A	−177.07 (11)	C8C—C9C—C10C—F5C	−179.60 (11)
F4A—C9A—C10A—C5A	178.64 (11)	F4C—C9C—C10C—C5C	176.91 (11)
C8A—C9A—C10A—C5A	1.0 (2)	C8C—C9C—C10C—C5C	−1.26 (19)
C6A—C5A—C10A—F5A	178.67 (11)	C6C—C5C—C10C—F5C	179.46 (11)
C3A—C5A—C10A—F5A	4.83 (18)	C3C—C5C—C10C—F5C	5.01 (18)
C6A—C5A—C10A—C9A	0.64 (19)	C6C—C5C—C10C—C9C	1.16 (19)
C3A—C5A—C10A—C9A	−173.20 (12)	C3C—C5C—C10C—C9C	−173.29 (12)
C3B—N1B—C2B—O1B	0.5 (2)	C3D—N1D—C2D—O1D	3.1 (2)
C3B—N1B—C2B—C1B	−179.40 (12)	C3D—N1D—C2D—C1D	−176.07 (12)
C2B—N1B—C3B—C5B	87.95 (15)	C2D—N1D—C3D—C5D	84.22 (15)
C2B—N1B—C3B—C4B	−146.12 (13)	C2D—N1D—C3D—C4D	−150.02 (12)
N1B—C3B—C5B—C10B	−111.38 (14)	N1D—C3D—C5D—C10D	−111.70 (14)
C4B—C3B—C5B—C10B	124.43 (14)	C4D—C3D—C5D—C10D	124.24 (14)
N1B—C3B—C5B—C6B	67.47 (16)	N1D—C3D—C5D—C6D	66.39 (16)
C4B—C3B—C5B—C6B	−56.73 (17)	C4D—C3D—C5D—C6D	−57.67 (17)
C10B—C5B—C6B—F1B	178.78 (12)	C10D—C5D—C6D—F1D	178.71 (12)
C3B—C5B—C6B—F1B	−0.14 (19)	C3D—C5D—C6D—F1D	0.50 (19)
C10B—C5B—C6B—C7B	−0.9 (2)	C10D—C5D—C6D—C7D	−1.0 (2)
C3B—C5B—C6B—C7B	−179.81 (12)	C3D—C5D—C6D—C7D	−179.19 (13)
F1B—C6B—C7B—F2B	2.61 (19)	F1D—C6D—C7D—F2D	2.58 (19)
C5B—C6B—C7B—F2B	−177.70 (12)	C5D—C6D—C7D—F2D	−177.72 (12)
F1B—C6B—C7B—C8B	−178.39 (12)	F1D—C6D—C7D—C8D	−178.46 (12)
C5B—C6B—C7B—C8B	1.3 (2)	C5D—C6D—C7D—C8D	1.2 (2)
F2B—C7B—C8B—F3B	−1.0 (2)	F2D—C7D—C8D—F3D	−0.9 (2)
C6B—C7B—C8B—F3B	179.99 (12)	C6D—C7D—C8D—F3D	−179.87 (12)
F2B—C7B—C8B—C9B	177.89 (12)	F2D—C7D—C8D—C9D	177.97 (12)
C6B—C7B—C8B—C9B	−1.1 (2)	C6D—C7D—C8D—C9D	−1.0 (2)
F3B—C8B—C9B—F4B	−0.1 (2)	F3D—C8D—C9D—F4D	−0.3 (2)
C7B—C8B—C9B—F4B	−179.03 (12)	C7D—C8D—C9D—F4D	−179.19 (13)
F3B—C8B—C9B—C10B	179.50 (12)	F3D—C8D—C9D—C10D	179.44 (12)
C7B—C8B—C9B—C10B	0.6 (2)	C7D—C8D—C9D—C10D	0.6 (2)
F4B—C9B—C10B—F5B	−0.73 (19)	F4D—C9D—C10D—F5D	−0.7 (2)
C8B—C9B—C10B—F5B	179.64 (12)	C8D—C9D—C10D—F5D	179.57 (12)
F4B—C9B—C10B—C5B	179.38 (12)	F4D—C9D—C10D—C5D	179.40 (12)
C8B—C9B—C10B—C5B	−0.2 (2)	C8D—C9D—C10D—C5D	−0.3 (2)
C6B—C5B—C10B—F5B	−179.52 (11)	C6D—C5D—C10D—F5D	−179.39 (11)
C3B—C5B—C10B—F5B	−0.6 (2)	C3D—C5D—C10D—F5D	−1.2 (2)
C6B—C5B—C10B—C9B	0.4 (2)	C6D—C5D—C10D—C9D	0.5 (2)
C3B—C5B—C10B—C9B	179.28 (12)	C3D—C5D—C10D—C9D	178.73 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O1D^i	0.88	2.02	2.8443 (15)	156
N1B—H1AA···O1A	0.88	2.03	2.8855 (15)	165
N1C—H1BA···O1B^ii	0.88	1.96	2.8380 (15)	172
N1D—H1CA···O1C	0.88	2.00	2.8569 (15)	164

Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.