6-Fluoro­indan-1-one

Slaw, B.R.; Tanski, J.M.

doi:10.1107/S1600536814015049

organic compounds

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ISSN: 2056-9890

Volume 70| Part 8| August 2014| Page o841

doi:10.1107/S1600536814015049

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6-Fluoroindan-1-one

Benjamin R. Slaw ^a and Joseph M. Tanski ^a ^*

^aDepartment of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA
^*Correspondence e-mail: jotanski@vassar.edu

(Received 6 June 2014; accepted 26 June 2014; online 2 July 2014)

The title compound, C₉H₇FO, crystallizes with two independent molecules in the asymmetric unit, in which corresponding bond lengths are the same within experimental error. The five-membered ring in each molecule is almost planar, with r.m.s. deviations of 0.016 and 0.029 Å. In the crystal, molecules form sheets parallel to (1 0 0) via C—H⋯O and C—H⋯F interactions with F⋯F contacts [3.1788 (16) and 3.2490 (16) Å] between the sheets.

Keywords: crystal structure.

CCDC reference: 1010372

Related literature

For the synthesis of 6-fluoroindan-1-one, see: Cui et al. (2004 ) and for its use in synthesis, see: Musso et al. (2003 ); Ślusarczyk et al. (2007 ); Yin et al. (2013 ). For the structure of the parent comound, 1-indanone, see: Morin et al. (1974 ) and Ruiz et al. (2004 ), the later containing a detailed analysis of the hydrogen bonding. For a related isomeric structure, 5-fluoroindan-1-one, see: Garcia et al. (1995 ). For more information on C—H⋯X interactions, see Desiraju & Steiner (1999 ) and on fluorine–fluorine interactions in the solid state, see: Baker et al. (2012 ). For van der Waals radii, see: Bondi (1964 ).

Experimental

Crystal data

C₉H₇FO
M_r = 150.15
Monoclinic, P 2₁ /n
a = 7.1900 (4) Å
b = 12.4811 (6) Å
c = 15.8685 (8) Å
β = 99.453 (1)°
V = 1404.69 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 125 K
0.37 × 0.26 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 2007 ) T_min = 0.91, T_max = 1.00
22840 measured reflections
4298 independent reflections
3345 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.121
S = 1.03
4298 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.95	2.47	3.3873 (14)	161
C14—H14⋯O2ⁱⁱ	0.95	2.65	3.5107 (14)	150
C2—H2B⋯F2ⁱⁱⁱ	0.99	2.46	3.2062 (13)	132
C6—H6⋯O2^iv	0.95	2.65	3.5338 (14)	154
C11—H11B⋯O1^v	0.99	2.52	3.3348 (13)	140
C15—H15⋯F1^vi	0.95	2.52	3.3664 (13)	148
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (v) -x+1, -y+1, -z+1; (vi) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, OLEX2 (Dolomanov et al., 2009 ) and Mercury (Macrae et al., 2006 ).

Supporting information

CCDC reference: 1010372

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814015049/kj2241sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814015049/kj2241Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814015049/kj2241Isup3.cml

checkCIF report

Comment top

The titular compound 6-fluoroindan-1-one may be synthesized by the Tb(OTf)₃-catalyzed cyclization of 3-(4-fluorophenyl)propanoic acid (Cui et al., 2004). The substance has found laboratory applications in the synthesis of α-arylated compounds (Yin et al., 2013), the synthesis of ethyl 2-(6-fluoro-1-hydroxy-1-indanyl)acetate, a potent muscle relaxant derivative (Musso et al., 2003), and in the creation of methylene-bridged biologically active pteridine derivatives for potential hepatitis C treatments (Ślusarczyk et al., 2007). The crystal structure of the parent compound, 1-indanone, has been reported previously (Morin et al., 1974; Ruiz et al., 2004), as has the structure of an isomer of the title compound, 5-fluoroindan-1-one (Garcia et al., 1995).

The titular compound crystallizes with two molecules of 6-fluoroindan-1-one in the asymmetric unit (Figure 1). The carbonyl C—O bond lengths of 1.2172 (13) and 1.2179 (13) Å, as for the other bond lengths, are the same within the experimental error between the two independent molecules. These carbonyl C—O bond lengths are similar to those found in the structure of the parent comound, 1-indanone, 1.217 (2) Å (Ruiz et al., 2004), and in the structure of the isomeric compound 5-fluoroindan-1-one, 1.218 (2) Å (Garcia et al.,1995). The C—F bond lengths in 6-fluoroindan-1-one, 1.3592 (12) and 1.3596 (11) Å, are also very similar to that found in the structure of the isomeric compound 5-fluoroindan-1-one, 1.354 (2) Å.

The molecules pack together in the solid state to form a two-dimensional sheet parallel to the 1 0 0 plane via several intermolecular C—H···O and C—F···H interactions (Figure 2, Table 2) measuring slightly less than the sum of the van der Waals radii (Bondi, 1964). The oxygen atom in each independent molecule forms two C—H···O interactions, while each independent molecule also forms one C—F···H interaction. For a discussion of C—H···X interactions, see Desiraju & Steiner (1999). There are also two long F···F interactions linking the two-dimensional sheets, (Figure 3, Table 1), which are somewhat longer than the sum of the van der Waals radii, 2.94 Å (Bondi, 1964). For a discussion of fluorine-fluorine interactions, which can vary widely in their metrical parameters and strength, see Baker et al. (2012).

Related literature top

For the synthesis of 6-fluoroindan-1-one, see: Cui et al. (2004) and for its use in synthesis, see: Musso et al. (2003); Ślusarczyk et al. (2007); Yin et al. (2013). For the structure of the parent comound, 1-indanone, see: Morin et al. (1974) and Ruiz et al. (2004), the later containing a detailed analysis of the hydrogen bonding. For a related isomeric structure, 5-fluoroindan-1-one, see: Garcia et al. (1995). For more information on C—H···X interactions, see Desiraju & Steiner (1999) and on fluorine–fluorine interactions in the solid state, see: Baker et al. (2012). For van der Waals radii, see: Bondi (1964).

Experimental top

Crystalline 6-fluoroindan-1-one (I) was purchased from Aldrich Chemical Company, USA.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006).

Figures top

	Fig. 1. A view of the two independent molecules of the title compound, with atom numbering scheme. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. A view of the C—H···O and C—H···F interactions in the packing of 6-fluoroindan-1-one forming a sheet parallel to the 1 0 0 plane. Displacement ellipsoids are shown at the 50% probability level. Symmetry codes: (i) -x + 1, -y + 1, -z; (iii) -x + 3/2, y + 1/2, -z + 1/2; (iv) -x + 1/2, y - 1/2, -z + 1/2; (v) x + 1/2, -y + 3/2, z + 1/2; (vi) x + 1/2, -y + 3/2, z - 1/2; (vii) -x + 1, -y + 1, -z + 1.
	Fig. 3. A view of the intermolecular F···F interactions in the packing of 6-fluoroindan-1-one. Distances F1···F1ⁱ 3.1788 (16) Å, F2···F2ⁱⁱ 3.2490 (16) Å. Displacement ellipsoids are shown at the 50% probability level; hydrogen atoms removed for clarity. Symmetry codes: (i) -x + 1, -y + 1, -z; (ii) -x, -y + 1, -z.

6-Fluoroindan-1-one top

Crystal data top

C₉H₇FO	F(000) = 624
M_r = 150.15	D_x = 1.420 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.1900 (4) Å	Cell parameters from 9796 reflections
b = 12.4811 (6) Å	θ = 2.6–30.5°
c = 15.8685 (8) Å	µ = 0.11 mm⁻¹
β = 99.453 (1)°	T = 125 K
V = 1404.69 (13) Å³	Plate, colourless
Z = 8	0.37 × 0.26 × 0.04 mm

Data collection top

Bruker APEXII CCD diffractometer	4298 independent reflections
Radiation source: fine-focus sealed tube	3345 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 8.3333 pixels mm^-1	θ_max = 30.5°, θ_min = 2.1°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker 2007)	k = −17→17
T_min = 0.91, T_max = 1.00	l = −22→22
22840 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0654P)² + 0.2949P] where P = (F_o² + 2F_c²)/3
4298 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₉H₇FO	V = 1404.69 (13) Å³
M_r = 150.15	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.1900 (4) Å	µ = 0.11 mm⁻¹
b = 12.4811 (6) Å	T = 125 K
c = 15.8685 (8) Å	0.37 × 0.26 × 0.04 mm
β = 99.453 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4298 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2007)	3345 reflections with I > 2σ(I)
T_min = 0.91, T_max = 1.00	R_int = 0.029
22840 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.03	Δρ_max = 0.40 e Å⁻³
4298 reflections	Δρ_min = −0.21 e Å⁻³
199 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

	x	y	z	U_iso*/U_eq
F1	0.57983 (11)	0.61035 (7)	0.04096 (4)	0.03306 (19)
F2	0.08173 (11)	0.60328 (6)	0.05655 (4)	0.03227 (19)
O1	0.58188 (12)	0.56668 (7)	0.37571 (5)	0.02425 (18)
O2	0.10060 (13)	0.64991 (7)	0.39289 (5)	0.0290 (2)
C1	0.63562 (14)	0.65257 (8)	0.35245 (6)	0.01661 (19)
C2	0.69797 (16)	0.74848 (9)	0.40858 (7)	0.0209 (2)
H2A	0.8032	0.7285	0.4543	0.025*
H2B	0.5922	0.7756	0.4354	0.025*
C3	0.76215 (15)	0.83443 (8)	0.35003 (7)	0.0198 (2)
H3A	0.6904	0.9017	0.3526	0.024*
H3B	0.8983	0.8498	0.3666	0.024*
C4	0.72154 (14)	0.78578 (8)	0.26152 (7)	0.0170 (2)
C5	0.74667 (15)	0.83033 (9)	0.18320 (7)	0.0217 (2)
H5	0.7957	0.9007	0.1806	0.026*
C6	0.69871 (16)	0.76990 (10)	0.10921 (7)	0.0238 (2)
H6	0.7148	0.7986	0.0555	0.029*
C7	0.62701 (15)	0.66714 (9)	0.11444 (7)	0.0218 (2)
C8	0.60039 (14)	0.62037 (9)	0.19016 (7)	0.0188 (2)
H8	0.5513	0.5499	0.1923	0.023*
C9	0.64971 (14)	0.68253 (8)	0.26346 (6)	0.01567 (19)
C10	0.14218 (14)	0.56199 (9)	0.36835 (6)	0.0184 (2)
C11	0.19726 (16)	0.46437 (9)	0.42394 (7)	0.0214 (2)
H11A	0.0886	0.4385	0.4493	0.026*
H11B	0.3016	0.4821	0.4707	0.026*
C12	0.26009 (15)	0.37845 (9)	0.36496 (7)	0.0195 (2)
H12A	0.3964	0.363	0.381	0.023*
H12B	0.1884	0.3112	0.3678	0.023*
C13	0.21781 (14)	0.42705 (8)	0.27662 (6)	0.01607 (19)
C14	0.24187 (15)	0.38210 (9)	0.19853 (7)	0.0195 (2)
H14	0.2889	0.3112	0.196	0.023*
C15	0.19576 (15)	0.44297 (9)	0.12451 (7)	0.0212 (2)
H15	0.2117	0.4142	0.0707	0.025*
C16	0.12627 (15)	0.54614 (9)	0.13004 (6)	0.0204 (2)
C17	0.10060 (15)	0.59323 (8)	0.20572 (7)	0.0189 (2)
H17	0.0525	0.6639	0.2079	0.023*
C18	0.14943 (14)	0.53097 (8)	0.27900 (6)	0.01578 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0391 (4)	0.0439 (5)	0.0154 (3)	0.0011 (3)	0.0024 (3)	−0.0091 (3)
F2	0.0434 (4)	0.0365 (4)	0.0151 (3)	−0.0035 (3)	−0.0006 (3)	0.0100 (3)
O1	0.0307 (4)	0.0212 (4)	0.0204 (4)	−0.0055 (3)	0.0027 (3)	0.0036 (3)
O2	0.0401 (5)	0.0244 (4)	0.0227 (4)	0.0082 (4)	0.0053 (3)	−0.0045 (3)
C1	0.0165 (4)	0.0173 (5)	0.0158 (4)	0.0016 (4)	0.0022 (3)	−0.0003 (3)
C2	0.0274 (5)	0.0192 (5)	0.0165 (5)	−0.0002 (4)	0.0044 (4)	−0.0029 (4)
C3	0.0217 (5)	0.0158 (5)	0.0220 (5)	−0.0010 (4)	0.0041 (4)	−0.0034 (4)
C4	0.0163 (4)	0.0160 (5)	0.0192 (5)	0.0021 (3)	0.0039 (4)	0.0005 (4)
C5	0.0210 (5)	0.0195 (5)	0.0254 (5)	0.0013 (4)	0.0067 (4)	0.0051 (4)
C6	0.0224 (5)	0.0307 (6)	0.0193 (5)	0.0050 (4)	0.0070 (4)	0.0061 (4)
C7	0.0214 (5)	0.0287 (6)	0.0149 (5)	0.0047 (4)	0.0018 (4)	−0.0040 (4)
C8	0.0184 (5)	0.0195 (5)	0.0179 (5)	0.0009 (4)	0.0013 (4)	−0.0024 (4)
C9	0.0166 (4)	0.0154 (4)	0.0151 (4)	0.0010 (3)	0.0027 (3)	−0.0008 (3)
C10	0.0187 (5)	0.0205 (5)	0.0159 (4)	0.0010 (4)	0.0026 (3)	−0.0004 (4)
C11	0.0262 (5)	0.0234 (5)	0.0147 (4)	0.0006 (4)	0.0037 (4)	0.0026 (4)
C12	0.0214 (5)	0.0191 (5)	0.0182 (5)	0.0026 (4)	0.0040 (4)	0.0048 (4)
C13	0.0156 (4)	0.0166 (5)	0.0160 (4)	−0.0011 (3)	0.0027 (3)	0.0012 (3)
C14	0.0189 (5)	0.0195 (5)	0.0206 (5)	−0.0004 (4)	0.0044 (4)	−0.0027 (4)
C15	0.0212 (5)	0.0270 (5)	0.0159 (5)	−0.0047 (4)	0.0045 (4)	−0.0039 (4)
C16	0.0209 (5)	0.0258 (5)	0.0135 (4)	−0.0047 (4)	0.0003 (4)	0.0049 (4)
C17	0.0200 (5)	0.0178 (5)	0.0178 (5)	0.0000 (4)	−0.0002 (4)	0.0029 (4)
C18	0.0157 (4)	0.0169 (5)	0.0145 (4)	−0.0007 (3)	0.0019 (3)	0.0002 (3)

Geometric parameters (Å, º) top

F1—C7	1.3592 (12)	C7—C8	1.3772 (15)
F1—F1ⁱ	3.1788 (16)	C8—C9	1.3947 (14)
F2—C16	1.3596 (11)	C8—H8	0.95
F2—F2ⁱⁱ	3.2490 (16)	C10—C18	1.4790 (14)
O1—C1	1.2172 (13)	C10—C11	1.5181 (15)
O2—C10	1.2179 (13)	C11—C12	1.5392 (15)
C1—C9	1.4802 (14)	C11—H11A	0.99
C1—C2	1.5152 (14)	C11—H11B	0.99
C2—C3	1.5387 (15)	C12—C13	1.5118 (14)
C2—H2A	0.99	C12—H12A	0.99
C2—H2B	0.99	C12—H12B	0.99
C3—C4	1.5140 (14)	C13—C18	1.3898 (14)
C3—H3A	0.99	C13—C14	1.3967 (14)
C3—H3B	0.99	C14—C15	1.3924 (15)
C4—C9	1.3905 (14)	C14—H14	0.95
C4—C5	1.4000 (14)	C15—C16	1.3892 (16)
C5—C6	1.3904 (16)	C15—H15	0.95
C5—H5	0.95	C16—C17	1.3764 (15)
C6—C7	1.3898 (17)	C17—C18	1.3946 (14)
C6—H6	0.95	C17—H17	0.95

F1···F1ⁱ	3.1788 (16)	F2···F2ⁱⁱ	3.2490 (16)

C7—F1—F1ⁱ	145.61 (8)	C8—C9—C1	127.39 (9)
C16—F2—F2ⁱⁱ	94.04 (6)	O2—C10—C18	126.26 (10)
O1—C1—C9	125.92 (9)	O2—C10—C11	126.27 (10)
O1—C1—C2	126.55 (9)	C18—C10—C11	107.46 (9)
C9—C1—C2	107.53 (8)	C10—C11—C12	106.29 (8)
C1—C2—C3	106.56 (8)	C10—C11—H11A	110.5
C1—C2—H2A	110.4	C12—C11—H11A	110.5
C3—C2—H2A	110.4	C10—C11—H11B	110.5
C1—C2—H2B	110.4	C12—C11—H11B	110.5
C3—C2—H2B	110.4	H11A—C11—H11B	108.7
H2A—C2—H2B	108.6	C13—C12—C11	104.47 (8)
C4—C3—C2	104.43 (8)	C13—C12—H12A	110.9
C4—C3—H3A	110.9	C11—C12—H12A	110.9
C2—C3—H3A	110.9	C13—C12—H12B	110.9
C4—C3—H3B	110.9	C11—C12—H12B	110.9
C2—C3—H3B	110.9	H12A—C12—H12B	108.9
H3A—C3—H3B	108.9	C18—C13—C14	119.66 (9)
C9—C4—C5	119.36 (10)	C18—C13—C12	111.56 (9)
C9—C4—C3	111.52 (9)	C14—C13—C12	128.76 (10)
C5—C4—C3	129.12 (10)	C15—C14—C13	118.83 (10)
C6—C5—C4	118.94 (10)	C15—C14—H14	120.6
C6—C5—H5	120.5	C13—C14—H14	120.6
C4—C5—H5	120.5	C16—C15—C14	119.39 (9)
C7—C6—C5	119.55 (10)	C16—C15—H15	120.3
C7—C6—H6	120.2	C14—C15—H15	120.3
C5—C6—H6	120.2	F2—C16—C17	118.56 (10)
F1—C7—C8	118.46 (10)	F2—C16—C15	117.94 (9)
F1—C7—C6	118.21 (10)	C17—C16—C15	123.51 (9)
C8—C7—C6	123.32 (10)	C16—C17—C18	115.98 (10)
C7—C8—C9	116.05 (10)	C16—C17—H17	122.0
C7—C8—H8	122.0	C18—C17—H17	122.0
C9—C8—H8	122.0	C13—C18—C17	122.62 (9)
C4—C9—C8	122.78 (9)	C13—C18—C10	109.79 (9)
C4—C9—C1	109.83 (9)	C17—C18—C10	127.58 (10)

O2—C10—C18—C17	−3.94 (18)	C3—C4—C5—C6	−179.93 (10)
O2—C10—C18—C13	174.94 (11)	C2—C3—C4—C9	−2.21 (11)
O2—C10—C11—C12	−173.07 (11)	C2—C3—C4—C5	177.79 (10)
O1—C1—C9—C8	1.81 (17)	C2—C1—C9—C8	−177.56 (10)
O1—C1—C9—C4	−178.32 (10)	C2—C1—C9—C4	2.31 (11)
O1—C1—C2—C3	177.04 (10)	C1—C2—C3—C4	3.48 (11)
F2ⁱⁱ—F2—C16—C17	−142.91 (9)	C18—C13—C14—C15	−0.21 (15)
F2ⁱⁱ—F2—C16—C15	37.18 (10)	C18—C10—C11—C12	6.57 (11)
F2—C16—C17—C18	−179.74 (9)	C16—C17—C18—C13	−0.78 (15)
F1ⁱ—F1—C7—C8	−1.14 (19)	C16—C17—C18—C10	177.97 (10)
F1ⁱ—F1—C7—C6	179.25 (9)	C15—C16—C17—C18	0.17 (16)
F1—C7—C8—C9	−179.49 (9)	C14—C15—C16—F2	−179.69 (9)
C9—C4—C5—C6	0.07 (15)	C14—C15—C16—C17	0.40 (16)
C9—C1—C2—C3	−3.60 (11)	C14—C13—C18—C17	0.82 (15)
C7—C8—C9—C4	0.06 (15)	C14—C13—C18—C10	−178.13 (9)
C7—C8—C9—C1	179.91 (10)	C13—C14—C15—C16	−0.38 (15)
C6—C7—C8—C9	0.10 (16)	C12—C13—C18—C17	179.76 (9)
C5—C6—C7—F1	179.42 (9)	C12—C13—C18—C10	0.81 (12)
C5—C6—C7—C8	−0.16 (17)	C12—C13—C14—C15	−178.95 (10)
C5—C4—C9—C8	−0.14 (15)	C11—C12—C13—C18	3.30 (11)
C5—C4—C9—C1	179.98 (9)	C11—C12—C13—C14	−177.87 (10)
C4—C5—C6—C7	0.07 (16)	C11—C10—C18—C17	176.42 (10)
C3—C4—C9—C8	179.86 (9)	C11—C10—C18—C13	−4.70 (12)
C3—C4—C9—C1	−0.02 (12)	C10—C11—C12—C13	−5.93 (11)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱⁱⁱ	0.95	2.47	3.3873 (14)	161
C14—H14···O2^iv	0.95	2.65	3.5107 (14)	150
C2—H2B···F2^v	0.99	2.46	3.2062 (13)	132
C6—H6···O2^vi	0.95	2.65	3.5338 (14)	154
C11—H11B···O1^vii	0.99	2.52	3.3348 (13)	140
C15—H15···F1ⁱ	0.95	2.52	3.3664 (13)	148

Symmetry codes: (i) −x+1, −y+1, −z; (iii) −x+3/2, y+1/2, −z+1/2; (iv) −x+1/2, y−1/2, −z+1/2; (v) x+1/2, −y+3/2, z+1/2; (vi) x+1/2, −y+3/2, z−1/2; (vii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.95	2.47	3.3873 (14)	161.1
C14—H14···O2ⁱⁱ	0.95	2.65	3.5107 (14)	150.3
C2—H2B···F2ⁱⁱⁱ	0.99	2.46	3.2062 (13)	132.2
C6—H6···O2^iv	0.95	2.65	3.5338 (14)	154.2
C11—H11B···O1^v	0.99	2.52	3.3348 (13)	139.7
C15—H15···F1^vi	0.95	2.52	3.3664 (13)	148.3

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x+1/2, −y+3/2, z+1/2; (iv) x+1/2, −y+3/2, z−1/2; (v) −x+1, −y+1, −z+1; (vi) −x+1, −y+1, −z.

Acknowledgements

This work was supported by Vassar College. X-ray facilities were provided by the US National Science Foundation (grant No. 0521237 to JMT).

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