9-Penta­fluoro­phenyl­methyl­ene-9H-fluorene

The principal structural feature of the title compound, C₂₀H₉F₅, is the dihedral angle of 51.22 (5)° between the substituent phenyl ring and the fluorene fragment of the mol­ecule. This results in the close approach of an F atom to the plane of the fluorene fragment, compromising the planarity of the latter. The conformation also permits virtually complete overlap and π–π interaction of the phenyl ring of one mol­ecule with the five-membered ring of the fluorene of another, in infinite chains of head-to-tail mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.113
• Data-to-parameter ratio = 11.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

---

Computing details

Data collection: P3 Software (Nicolet, 1980); cell refinement: P3 Software; data reduction: RDNIC (Howie, 1980); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1990).

9-Pentafluorophenylmethylene-9H-fluorene

Crystal data

C20H9F5	F(000) = 696
Mr = 344.27	Dx = 1.524 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.931 (6) Å	Cell parameters from 14 reflections
b = 7.448 (3) Å	θ = 8.2–12.3°
c = 15.647 (6) Å	µ = 0.13 mm^−1
β = 95.29 (3)°	T = 298 K
V = 1500.5 (11) Å^3	Block, green-yellow
Z = 4	0.50 × 0.30 × 0.30 mm

Data collection

Nicolet P3 diffractometer	Rint = 0.031
Radiation source: normal-focus sealed tube	θmax = 25.1°, θmin = 2.1°
Graphite monochromator	h = 0→15
θ–2θ scans	k = 0→8
2772 measured reflections	l = −18→18
2656 independent reflections	2 standard reflections every 50 reflections
1580 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0485P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
2656 reflections	Δρmax = 0.19 e Å^−3
227 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.036 (2)

Special details

Experimental. Scan rates, dependent on prescan intensity (Ip), were in the range 58.6 (Ip>2500) to 5.33 (Ip<150) ° 2θ min^-1. Scan widths, dependent on 2θ, were in the range 2.4 to 2.7 ° 2θ. Stationary crystal, stationary counter background counts were taken on either side of the peak each for 25% of the total (peak plus background) count time.

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 1.6060 (0.0083) x - 6.7213 (0.0039) y + 6.6070 (0.0072) z = 1.5455 (0.0022)

* 0.0081 (0.0022) C1 * -0.0473 (0.0022) C2 * -0.0580 (0.0025) C3 * -0.0052 (0.0024) C4 * 0.0346 (0.0025) C5 * 0.0387 (0.0023) C6 * 0.0455 (0.0024) C7 * 0.0043 (0.0025) C8 * -0.0404 (0.0026) C9 * -0.0532 (0.0027) C10 * -0.0113 (0.0023) C11 * 0.0434 (0.0022) C12 * 0.0409 (0.0020) C13 0.0296 (0.0032) C14 0.0972 (0.0037) C15 1.0583 (0.0039) C16 1.1003 (0.0047) C17 0.1904 (0.0053) C18 - 0.7410 (0.0050) C19 - 0.7708 (0.0044) C20 2.0138 (0.0031) F1 2.0311 (0.0043) F2 0.2086 (0.0054) F3 - 1.6265 (0.0053) F4 - 1.7048 (0.0039) F5

Rms deviation of fitted atoms = 0.0379

- 1.8028 (0.0132) x + 6.7109 (0.0048) y + 6.6005 (0.0148) z = 0.9296 (0.0073)

Angle to previous plane (with approximate e.s.d.) = 51.22 (0.05)

* 0.0213 (0.0017) C15 * -0.0172 (0.0018) C16 * -0.0010 (0.0019) C17 * 0.0150 (0.0019) C18 * -0.0100 (0.0019) C19 * -0.0081 (0.0018) C20 - 0.0969 (0.0033) F1 - 0.0133 (0.0035) F2 0.0504 (0.0035) F3 - 0.0083 (0.0034) F4 - 0.0186 (0.0033) F5

Rms deviation of fitted atoms = 0.0138

- 1.6476 (0.0067) x - 6.7140 (0.0038) y + 6.6294 (0.0067) z = 1.5535 (0.0020)

Angle to previous plane (with approximate e.s.d.) = 51.35 (0.05)

* 0.0035 (0.0022) C1 * -0.0529 (0.0023) C2 * -0.0599 (0.0025) C3 * -0.0025 (0.0024) C4 * 0.0385 (0.0025) C5 * 0.0389 (0.0023) C6 * 0.0457 (0.0024) C7 * 0.0082 (0.0025) C8 * -0.0374 (0.0027) C9 * -0.0548 (0.0027) C10 * -0.0167 (0.0024) C11 * 0.0388 (0.0023) C12 * 0.0332 (0.0021) C13 * 0.0172 (0.0019) C14 0.0810 (0.0032) C15 1.0419 (0.0035) C16 1.0804 (0.0041) C17 0.1669 (0.0046) C18 - 0.7646 (0.0043) C19 - 0.7907 (0.0038) C20 2.0008 (0.0027) F1 2.0112 (0.0036) F2 0.1816 (0.0046) F3 - 1.6536 (0.0043) F4 - 1.7248 (0.0032) F5

Rms deviation of fitted atoms = 0.0370

- 1.5233 (0.0140) x - 6.8362 (0.0049) y + 6.0754 (0.0165) z = 1.4282 (0.0037)

Angle to previous plane (with approximate e.s.d.) = 2.27 (0.10)

* 0.0059 (0.0018) C1 * -0.0012 (0.0019) C2 * -0.0051 (0.0021) C3 * 0.0066 (0.0021) C4 * -0.0017 (0.0020) C5 * -0.0045 (0.0019) C6

Rms deviation of fitted atoms = 0.0047

- 1.6265 (0.0158) x - 6.7580 (0.0052) y + 6.4308 (0.0176) z = 1.5238 (0.0056)

Angle to previous plane (with approximate e.s.d.) = 1.47 (0.13)

* -0.0118 (0.0015) C1 * 0.0088 (0.0016) C6 * -0.0021 (0.0016) C7 * -0.0050 (0.0015) C12 * 0.0100 (0.0015) C13 - 0.0499 (0.0043) C2 - 0.0533 (0.0052) C3 - 0.0106 (0.0052) C4 0.0120 (0.0045) C5 - 0.0577 (0.0045) C8 - 0.1178 (0.0055) C9 - 0.1315 (0.0055) C10 - 0.0752 (0.0043) C11 0.0635 (0.0053) C15 1.0127 (0.0059) C16 1.0472 (0.0074) C17 0.1418 (0.0084) C18 - 0.7773 (0.0080) C19 - 0.7999 (0.0065) C20 1.9639 (0.0047) F1 1.9663 (0.0077) F2 0.1526 (0.0097) F3 - 1.6581 (0.0087) F4 - 1.7220 (0.0061) F5

Rms deviation of fitted atoms = 0.0083

- 1.4974 (0.0141) x - 6.6061 (0.0053) y + 7.1327 (0.0169) z = 1.8010 (0.0078)

Angle to previous plane (with approximate e.s.d.) = 2.94 (0.14)

* -0.0019 (0.0018) C7 * -0.0014 (0.0020) C8 * 0.0033 (0.0023) C9 * -0.0018 (0.0022) C10 * -0.0015 (0.0020) C11 * 0.0033 (0.0018) C12

Rms deviation of fitted atoms = 0.0023

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.

Anisotropic displacement parameters refined for all non-H atoms. H atoms placed in calculated positions and refined with a riding model.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1	0.30765 (12)	−0.1983 (2)	0.41178 (9)	0.0625 (5)
F2	0.50868 (13)	−0.1904 (2)	0.47131 (9)	0.0698 (5)
F3	0.65148 (11)	−0.0479 (3)	0.37512 (11)	0.0786 (6)
F4	0.59190 (12)	0.0834 (2)	0.21646 (11)	0.0726 (5)
F5	0.39028 (11)	0.0855 (2)	0.15771 (9)	0.0566 (5)
C1	0.04055 (18)	−0.0113 (3)	0.23347 (15)	0.0402 (6)
C2	0.01064 (19)	−0.0760 (4)	0.15201 (17)	0.0509 (7)
H2	0.0599	−0.1177	0.1171	0.061*
C3	−0.0944 (2)	−0.0776 (4)	0.1233 (2)	0.0625 (8)
H3	−0.1158	−0.1199	0.0686	0.075*
C4	−0.1673 (2)	−0.0162 (4)	0.1759 (2)	0.0659 (9)
H4	−0.2374	−0.0201	0.1562	0.079*
C5	−0.1385 (2)	0.0503 (4)	0.2567 (2)	0.0611 (8)
H5	−0.1881	0.0925	0.2911	0.073*
C6	−0.03374 (19)	0.0529 (3)	0.28539 (16)	0.0455 (7)
C7	0.0205 (2)	0.1180 (3)	0.36578 (16)	0.0464 (7)
C8	−0.0183 (2)	0.2013 (4)	0.43491 (18)	0.0640 (8)
H8	−0.0893	0.2190	0.4360	0.077*
C9	0.0503 (3)	0.2578 (4)	0.50226 (19)	0.0744 (10)
H9	0.0251	0.3134	0.5494	0.089*
C10	0.1562 (3)	0.2327 (4)	0.50053 (18)	0.0679 (9)
H10	0.2013	0.2724	0.5463	0.081*
C11	0.1955 (2)	0.1493 (4)	0.43159 (16)	0.0532 (7)
H11	0.2668	0.1329	0.4309	0.064*
C12	0.12806 (19)	0.0904 (3)	0.36354 (15)	0.0428 (6)
C13	0.14509 (18)	0.0049 (3)	0.28036 (14)	0.0379 (6)
C14	0.23204 (18)	−0.0475 (3)	0.24647 (16)	0.0424 (6)
H14	0.2221	−0.0912	0.1906	0.051*
C15	0.34053 (18)	−0.0464 (3)	0.28422 (15)	0.0388 (6)
C16	0.37518 (19)	−0.1202 (3)	0.36296 (16)	0.0446 (6)
C17	0.4783 (2)	−0.1206 (4)	0.39399 (16)	0.0485 (7)
C18	0.55114 (19)	−0.0507 (4)	0.34516 (18)	0.0506 (7)
C19	0.52104 (19)	0.0163 (4)	0.26503 (17)	0.0475 (7)
C20	0.41770 (19)	0.0172 (3)	0.23625 (15)	0.0422 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0609 (10)	0.0719 (11)	0.0558 (9)	−0.0026 (8)	0.0119 (8)	0.0146 (9)
F2	0.0768 (11)	0.0778 (12)	0.0513 (10)	0.0100 (9)	−0.0127 (8)	0.0093 (9)
F3	0.0440 (10)	0.0941 (14)	0.0937 (13)	0.0022 (9)	−0.0153 (9)	0.0025 (11)
F4	0.0443 (9)	0.0943 (13)	0.0819 (12)	−0.0020 (9)	0.0208 (8)	0.0096 (10)
F5	0.0532 (9)	0.0736 (11)	0.0438 (9)	0.0072 (8)	0.0093 (7)	0.0080 (8)
C1	0.0401 (14)	0.0378 (15)	0.0431 (15)	−0.0002 (12)	0.0064 (11)	0.0029 (12)
C2	0.0437 (16)	0.0548 (18)	0.0537 (17)	0.0019 (14)	0.0020 (13)	−0.0011 (14)
C3	0.0547 (18)	0.063 (2)	0.067 (2)	−0.0006 (16)	−0.0093 (15)	−0.0042 (16)
C4	0.0404 (17)	0.070 (2)	0.085 (2)	0.0016 (15)	−0.0019 (16)	0.0063 (19)
C5	0.0419 (17)	0.065 (2)	0.077 (2)	0.0031 (15)	0.0131 (15)	0.0032 (17)
C6	0.0422 (16)	0.0414 (16)	0.0542 (17)	0.0019 (12)	0.0122 (13)	0.0082 (13)
C7	0.0525 (16)	0.0424 (16)	0.0463 (15)	0.0042 (13)	0.0163 (13)	0.0063 (13)
C8	0.067 (2)	0.073 (2)	0.0548 (18)	0.0154 (17)	0.0218 (16)	0.0055 (17)
C9	0.098 (3)	0.074 (2)	0.0537 (19)	0.025 (2)	0.0229 (19)	−0.0038 (17)
C10	0.089 (2)	0.069 (2)	0.0437 (17)	0.0103 (18)	−0.0012 (16)	−0.0109 (15)
C11	0.0599 (18)	0.0549 (18)	0.0444 (16)	0.0073 (14)	0.0031 (13)	−0.0059 (14)
C12	0.0491 (16)	0.0388 (15)	0.0415 (15)	0.0031 (12)	0.0094 (12)	0.0016 (12)
C13	0.0370 (13)	0.0379 (14)	0.0390 (14)	−0.0015 (11)	0.0050 (11)	0.0026 (11)
C14	0.0405 (15)	0.0488 (16)	0.0374 (13)	−0.0005 (12)	0.0010 (11)	−0.0015 (12)
C15	0.0392 (14)	0.0396 (15)	0.0379 (14)	0.0033 (12)	0.0052 (11)	−0.0040 (12)
C16	0.0443 (16)	0.0448 (16)	0.0455 (15)	0.0022 (13)	0.0083 (12)	0.0019 (13)
C17	0.0521 (17)	0.0504 (17)	0.0417 (15)	0.0083 (14)	−0.0024 (13)	−0.0015 (13)
C18	0.0360 (15)	0.0533 (18)	0.0606 (18)	0.0037 (13)	−0.0061 (13)	−0.0078 (15)
C19	0.0382 (15)	0.0487 (17)	0.0571 (17)	0.0017 (13)	0.0127 (13)	−0.0024 (14)
C20	0.0456 (15)	0.0444 (16)	0.0372 (14)	0.0040 (13)	0.0063 (12)	0.0001 (12)

Geometric parameters (Å, º)

F1—C16	1.344 (3)	C8—C9	1.379 (4)
F2—C17	1.342 (3)	C8—H8	0.930
F3—C18	1.338 (3)	C9—C10	1.384 (4)
F4—C19	1.340 (3)	C9—H9	0.930
F5—C20	1.347 (3)	C10—C11	1.382 (4)
C1—C2	1.384 (3)	C10—H10	0.930
C1—C6	1.399 (3)	C11—C12	1.384 (3)
C1—C13	1.482 (3)	C11—H11	0.930
C2—C3	1.391 (4)	C12—C13	1.483 (3)
C2—H2	0.930	C13—C14	1.345 (3)
C3—C4	1.385 (4)	C14—C15	1.471 (3)
C3—H3	0.930	C14—H14	0.930
C4—C5	1.376 (4)	C15—C16	1.385 (3)
C4—H4	0.930	C15—C20	1.386 (3)
C5—C6	1.388 (4)	C16—C17	1.376 (4)
C5—H5	0.930	C17—C18	1.369 (4)
C6—C7	1.465 (4)	C18—C19	1.372 (4)
C7—C8	1.381 (3)	C19—C20	1.370 (3)
C7—C12	1.409 (3)
C2—C1—C6	120.4 (2)	C10—C11—C12	119.4 (3)
C2—C1—C13	130.5 (2)	C10—C11—H11	120.3
C6—C1—C13	109.2 (2)	C12—C11—H11	120.3
C1—C2—C3	118.8 (3)	C11—C12—C7	119.2 (2)
C1—C2—H2	120.6	C11—C12—C13	132.6 (2)
C3—C2—H2	120.6	C7—C12—C13	108.1 (2)
C4—C3—C2	120.2 (3)	C14—C13—C1	122.6 (2)
C4—C3—H3	119.9	C14—C13—C12	131.9 (2)
C2—C3—H3	119.9	C1—C13—C12	105.48 (19)
C5—C4—C3	121.6 (3)	C13—C14—C15	129.9 (2)
C5—C4—H4	119.2	C13—C14—H14	115.1
C3—C4—H4	119.2	C15—C14—H14	115.1
C4—C5—C6	118.4 (3)	C16—C15—C20	115.3 (2)
C4—C5—H5	120.8	C16—C15—C14	125.0 (2)
C6—C5—H5	120.8	C20—C15—C14	119.5 (2)
C5—C6—C1	120.6 (3)	F1—C16—C17	117.2 (2)
C5—C6—C7	131.2 (3)	F1—C16—C15	120.2 (2)
C1—C6—C7	108.2 (2)	C17—C16—C15	122.5 (2)
C8—C7—C12	121.0 (3)	F2—C17—C18	119.4 (2)
C8—C7—C6	129.9 (3)	F2—C17—C16	120.8 (2)
C12—C7—C6	109.0 (2)	C18—C17—C16	119.7 (2)
C9—C8—C7	118.8 (3)	F3—C18—C17	120.3 (2)
C9—C8—H8	120.6	F3—C18—C19	119.9 (2)
C7—C8—H8	120.6	C17—C18—C19	119.8 (2)
C8—C9—C10	120.7 (3)	F4—C19—C20	120.6 (2)
C8—C9—H9	119.6	F4—C19—C18	120.2 (2)
C10—C9—H9	119.6	C20—C19—C18	119.2 (2)
C11—C10—C9	120.8 (3)	F5—C20—C19	117.9 (2)
C11—C10—H10	119.6	F5—C20—C15	118.7 (2)
C9—C10—H10	119.6	C19—C20—C15	123.3 (2)
C6—C1—C2—C3	−0.6 (4)	C7—C12—C13—C14	179.5 (3)
C13—C1—C2—C3	179.5 (3)	C11—C12—C13—C1	−175.5 (3)
C1—C2—C3—C4	−0.4 (4)	C7—C12—C13—C1	1.4 (3)
C2—C3—C4—C5	1.2 (5)	C1—C13—C14—C15	−178.0 (2)
C3—C4—C5—C6	−0.8 (4)	C12—C13—C14—C15	4.1 (5)
C4—C5—C6—C1	−0.2 (4)	C13—C14—C15—C16	51.8 (4)
C4—C5—C6—C7	178.4 (3)	C13—C14—C15—C20	−134.6 (3)
C2—C1—C6—C5	1.0 (4)	C20—C15—C16—F1	−174.9 (2)
C13—C1—C6—C5	−179.2 (2)	C14—C15—C16—F1	−1.0 (4)
C2—C1—C6—C7	−177.9 (2)	C20—C15—C16—C17	3.9 (4)
C13—C1—C6—C7	1.9 (3)	C14—C15—C16—C17	177.8 (2)
C5—C6—C7—C8	−2.5 (5)	F1—C16—C17—F2	−2.5 (4)
C1—C6—C7—C8	176.3 (3)	C15—C16—C17—F2	178.7 (2)
C5—C6—C7—C12	−179.8 (3)	F1—C16—C17—C18	176.9 (2)
C1—C6—C7—C12	−1.1 (3)	C15—C16—C17—C18	−1.9 (4)
C12—C7—C8—C9	0.1 (4)	F2—C17—C18—F3	−1.6 (4)
C6—C7—C8—C9	−177.0 (3)	C16—C17—C18—F3	179.0 (2)
C7—C8—C9—C10	0.4 (5)	F2—C17—C18—C19	178.2 (2)
C8—C9—C10—C11	−0.5 (5)	C16—C17—C18—C19	−1.2 (4)
C9—C10—C11—C12	0.0 (5)	F3—C18—C19—F4	0.5 (4)
C10—C11—C12—C7	0.4 (4)	C17—C18—C19—F4	−179.3 (2)
C10—C11—C12—C13	177.1 (3)	F3—C18—C19—C20	−178.2 (2)
C8—C7—C12—C11	−0.5 (4)	C17—C18—C19—C20	2.0 (4)
C6—C7—C12—C11	177.1 (2)	F4—C19—C20—F5	0.7 (4)
C8—C7—C12—C13	−177.9 (2)	C18—C19—C20—F5	179.3 (2)
C6—C7—C12—C13	−0.2 (3)	F4—C19—C20—C15	−178.5 (2)
C2—C1—C13—C14	−0.5 (4)	C18—C19—C20—C15	0.2 (4)
C6—C1—C13—C14	179.6 (2)	C16—C15—C20—F5	177.8 (2)
C2—C1—C13—C12	177.8 (3)	C14—C15—C20—F5	3.6 (3)
C6—C1—C13—C12	−2.0 (3)	C16—C15—C20—C19	−3.0 (4)
C11—C12—C13—C14	2.6 (5)	C14—C15—C20—C19	−177.3 (2)