10-(4-Fluoro­benzyl­idene)­anthrone

The title compound, C₂₁H₁₃FO, was prepared from anthrone and 4-fluoro­benz­aldehyde. The central six-membered ring has an asymmetric boat conformation, in which the carbonyl C and the opposite C atom deviate from the plane of the other four atoms by 0.173 (2) and 0.319 (2) Å, respectively.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.103
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Version 1.05; Farrugia, 1999); software used to prepare material for publication: SHELXL97.

10-(4-Fluorobenzylidene)anthrone

Crystal data

C21H13FO	F(000) = 624
Mr = 300.31	Dx = 1.340 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.044 (6) Å	θ = 11.1–12.7°
b = 11.398 (3) Å	µ = 0.09 mm^−1
c = 13.820 (3) Å	T = 296 K
β = 109.79 (4)°	Prism, colorless
V = 1488.7 (10) Å^3	0.50 × 0.40 × 0.40 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.012
Radiation source: fine-focus sealed tube	θmax = 25.2°, θmin = 2.2°
Graphite monochromator	h = 0→12
ω/2θ scans	k = −1→13
3137 measured reflections	l = −16→15
2673 independent reflections	3 standard reflections every 60 min
2026 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)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0525P)^2 + 0.247P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2673 reflections	Δρmax = 0.18 e Å^−3
209 parameters	Δρmin = −0.14 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: 0.0058 (11)

Special details

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
F1	0.46323 (12)	1.13505 (10)	0.22408 (10)	0.0977 (4)
O1	0.04833 (13)	0.33472 (9)	0.13091 (9)	0.0663 (3)
C1	−0.21168 (17)	0.43485 (14)	0.01400 (11)	0.0580 (4)
H1	−0.2023	0.3541	0.0092	0.070*
C2	−0.33601 (18)	0.48835 (17)	−0.04179 (13)	0.0685 (5)
H2	−0.4111	0.4442	−0.0841	0.082*
C3	−0.34915 (17)	0.60847 (17)	−0.03479 (13)	0.0670 (5)
H3	−0.4344	0.6447	−0.0711	0.080*
C4	−0.23743 (15)	0.67491 (15)	0.02528 (11)	0.0569 (4)
H4	−0.2474	0.7559	0.0278	0.068*
C5	0.01670 (14)	0.69201 (12)	0.14295 (10)	0.0440 (3)
C6	0.20273 (15)	0.68760 (14)	0.31943 (10)	0.0522 (4)
H6	0.1967	0.7688	0.3236	0.063*
C7	0.29415 (16)	0.62594 (16)	0.40089 (11)	0.0614 (4)
H7	0.3481	0.6658	0.4598	0.074*
C8	0.30632 (17)	0.50583 (16)	0.39572 (12)	0.0637 (4)
H8	0.3696	0.4651	0.4504	0.076*
C9	0.22484 (16)	0.44651 (14)	0.30976 (12)	0.0555 (4)
H9	0.2334	0.3655	0.3061	0.067*
C10	0.03015 (15)	0.43892 (13)	0.14268 (10)	0.0481 (3)
C11	−0.09878 (15)	0.50051 (13)	0.07809 (10)	0.0469 (3)
C12	0.12921 (14)	0.50705 (13)	0.22794 (10)	0.0464 (3)
C13	0.11917 (14)	0.62930 (12)	0.23078 (10)	0.0440 (3)
C14	−0.10890 (14)	0.62261 (13)	0.08273 (10)	0.0458 (3)
C15	0.03268 (14)	0.80040 (13)	0.11125 (10)	0.0484 (3)
H15	−0.0457	0.8274	0.0579	0.058*
C16	0.14984 (15)	0.88502 (12)	0.14427 (10)	0.0465 (3)
C17	0.11758 (15)	1.00391 (13)	0.13936 (11)	0.0518 (4)
H17	0.0232	1.0269	0.1168	0.062*
C18	0.22135 (18)	1.08850 (14)	0.16698 (12)	0.0610 (4)
H18	0.1984	1.1677	0.1651	0.073*
C19	0.35952 (18)	1.05237 (15)	0.19737 (13)	0.0632 (4)
C20	0.39741 (17)	0.93670 (15)	0.20095 (13)	0.0620 (4)
H20	0.4921	0.9150	0.2209	0.074*
C21	0.29226 (15)	0.85320 (13)	0.17435 (11)	0.0528 (4)
H21	0.3165	0.7743	0.1765	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0777 (7)	0.0807 (8)	0.1135 (9)	−0.0333 (6)	0.0046 (6)	0.0053 (6)
O1	0.0806 (8)	0.0472 (7)	0.0663 (7)	0.0053 (5)	0.0185 (6)	−0.0010 (5)
C1	0.0670 (10)	0.0566 (9)	0.0463 (8)	−0.0126 (7)	0.0139 (7)	−0.0021 (7)
C2	0.0587 (10)	0.0786 (12)	0.0557 (9)	−0.0172 (9)	0.0031 (8)	−0.0046 (8)
C3	0.0474 (9)	0.0798 (12)	0.0617 (10)	0.0008 (8)	0.0025 (7)	0.0004 (9)
C4	0.0495 (8)	0.0606 (9)	0.0528 (8)	0.0037 (7)	0.0071 (7)	−0.0026 (7)
C5	0.0423 (7)	0.0470 (8)	0.0399 (7)	0.0037 (6)	0.0105 (6)	−0.0024 (6)
C6	0.0518 (8)	0.0559 (8)	0.0447 (8)	0.0007 (7)	0.0109 (6)	−0.0008 (6)
C7	0.0534 (9)	0.0759 (11)	0.0451 (8)	−0.0039 (8)	0.0040 (7)	0.0004 (7)
C8	0.0509 (8)	0.0739 (11)	0.0551 (9)	0.0044 (8)	0.0034 (7)	0.0170 (8)
C9	0.0501 (8)	0.0546 (9)	0.0588 (9)	0.0063 (7)	0.0145 (7)	0.0112 (7)
C10	0.0552 (8)	0.0460 (8)	0.0457 (8)	0.0006 (6)	0.0204 (7)	0.0023 (6)
C11	0.0510 (8)	0.0504 (8)	0.0393 (7)	−0.0046 (6)	0.0151 (6)	−0.0001 (6)
C12	0.0431 (7)	0.0522 (8)	0.0446 (7)	0.0045 (6)	0.0159 (6)	0.0057 (6)
C13	0.0408 (7)	0.0497 (8)	0.0414 (7)	0.0017 (6)	0.0137 (6)	0.0012 (6)
C14	0.0446 (7)	0.0523 (8)	0.0385 (7)	−0.0008 (6)	0.0114 (6)	−0.0008 (6)
C15	0.0442 (7)	0.0486 (8)	0.0458 (7)	0.0051 (6)	0.0067 (6)	0.0011 (6)
C16	0.0477 (7)	0.0465 (8)	0.0412 (7)	0.0025 (6)	0.0098 (6)	0.0029 (6)
C17	0.0495 (8)	0.0508 (8)	0.0516 (8)	0.0067 (7)	0.0123 (6)	0.0064 (6)
C18	0.0706 (11)	0.0441 (8)	0.0630 (10)	−0.0007 (7)	0.0157 (8)	0.0045 (7)
C19	0.0600 (10)	0.0592 (10)	0.0601 (9)	−0.0148 (8)	0.0068 (7)	0.0045 (8)
C20	0.0448 (8)	0.0708 (11)	0.0631 (10)	0.0003 (7)	0.0088 (7)	0.0092 (8)
C21	0.0501 (8)	0.0490 (8)	0.0552 (8)	0.0067 (7)	0.0124 (7)	0.0046 (6)

Geometric parameters (Å, º)

F1—C19	1.3598 (19)	C8—H8	0.9300
O1—C10	1.2209 (17)	C9—C12	1.394 (2)
C1—C2	1.369 (2)	C9—H9	0.9300
C1—C11	1.397 (2)	C10—C11	1.478 (2)
C1—H1	0.9300	C10—C12	1.479 (2)
C2—C3	1.382 (3)	C11—C14	1.398 (2)
C2—H2	0.9300	C12—C13	1.399 (2)
C3—C4	1.375 (2)	C15—C16	1.470 (2)
C3—H3	0.9300	C15—H15	0.9300
C4—C14	1.399 (2)	C16—C17	1.390 (2)
C4—H4	0.9300	C16—C21	1.396 (2)
C5—C15	1.338 (2)	C17—C18	1.376 (2)
C5—C13	1.4824 (19)	C17—H17	0.9300
C5—C14	1.483 (2)	C18—C19	1.370 (3)
C6—C7	1.380 (2)	C18—H18	0.9300
C6—C13	1.397 (2)	C19—C20	1.368 (2)
C6—H6	0.9300	C20—C21	1.376 (2)
C7—C8	1.378 (2)	C20—H20	0.9300
C7—H7	0.9300	C21—H21	0.9300
C8—C9	1.371 (2)
C2—C1—C11	120.56 (16)	C14—C11—C10	120.50 (13)
C2—C1—H1	119.7	C9—C12—C13	120.47 (14)
C11—C1—H1	119.7	C9—C12—C10	118.65 (13)
C1—C2—C3	119.50 (15)	C13—C12—C10	120.66 (13)
C1—C2—H2	120.2	C6—C13—C12	118.10 (13)
C3—C2—H2	120.2	C6—C13—C5	122.23 (13)
C4—C3—C2	120.67 (16)	C12—C13—C5	119.61 (12)
C4—C3—H3	119.7	C11—C14—C4	117.73 (13)
C2—C3—H3	119.7	C11—C14—C5	119.69 (13)
C3—C4—C14	121.03 (16)	C4—C14—C5	122.51 (14)
C3—C4—H4	119.5	C5—C15—C16	132.55 (13)
C14—C4—H4	119.5	C5—C15—H15	113.7
C15—C5—C13	125.88 (13)	C16—C15—H15	113.7
C15—C5—C14	118.82 (12)	C17—C16—C21	117.81 (14)
C13—C5—C14	115.17 (12)	C17—C16—C15	118.41 (13)
C7—C6—C13	120.63 (15)	C21—C16—C15	123.65 (13)
C7—C6—H6	119.7	C18—C17—C16	121.85 (14)
C13—C6—H6	119.7	C18—C17—H17	119.1
C8—C7—C6	120.64 (15)	C16—C17—H17	119.1
C8—C7—H7	119.7	C19—C18—C17	117.91 (15)
C6—C7—H7	119.7	C19—C18—H18	121.0
C9—C8—C7	119.82 (15)	C17—C18—H18	121.0
C9—C8—H8	120.1	F1—C19—C20	118.67 (16)
C7—C8—H8	120.1	F1—C19—C18	118.57 (16)
C8—C9—C12	120.27 (15)	C20—C19—C18	122.76 (15)
C8—C9—H9	119.9	C19—C20—C21	118.54 (15)
C12—C9—H9	119.9	C19—C20—H20	120.7
O1—C10—C11	121.44 (14)	C21—C20—H20	120.7
O1—C10—C12	121.76 (14)	C20—C21—C16	121.09 (15)
C11—C10—C12	116.57 (13)	C20—C21—H21	119.5
C1—C11—C14	120.42 (14)	C16—C21—H21	119.5
C1—C11—C10	119.07 (14)
C11—C1—C2—C3	0.3 (3)	C15—C5—C13—C12	−148.89 (14)
C1—C2—C3—C4	1.9 (3)	C14—C5—C13—C12	26.92 (18)
C2—C3—C4—C14	−1.6 (3)	C1—C11—C14—C4	3.1 (2)
C13—C6—C7—C8	1.0 (2)	C10—C11—C14—C4	−175.50 (13)
C6—C7—C8—C9	−1.4 (3)	C1—C11—C14—C5	−173.86 (13)
C7—C8—C9—C12	−0.4 (2)	C10—C11—C14—C5	7.55 (19)
C2—C1—C11—C14	−2.9 (2)	C3—C4—C14—C11	−0.9 (2)
C2—C1—C11—C10	175.75 (14)	C3—C4—C14—C5	175.94 (14)
O1—C10—C11—C1	10.5 (2)	C15—C5—C14—C11	148.10 (14)
C12—C10—C11—C1	−164.17 (13)	C13—C5—C14—C11	−28.02 (18)
O1—C10—C11—C14	−170.94 (13)	C15—C5—C14—C4	−28.7 (2)
C12—C10—C11—C14	14.44 (19)	C13—C5—C14—C4	155.18 (13)
C8—C9—C12—C13	2.5 (2)	C13—C5—C15—C16	4.4 (2)
C8—C9—C12—C10	−172.10 (14)	C14—C5—C15—C16	−171.30 (14)
O1—C10—C12—C9	−15.5 (2)	C5—C15—C16—C17	−146.85 (16)
C11—C10—C12—C9	159.09 (13)	C5—C15—C16—C21	37.3 (2)
O1—C10—C12—C13	169.87 (13)	C21—C16—C17—C18	−2.6 (2)
C11—C10—C12—C13	−15.52 (19)	C15—C16—C17—C18	−178.71 (14)
C7—C6—C13—C12	1.1 (2)	C16—C17—C18—C19	1.7 (2)
C7—C6—C13—C5	178.16 (13)	C17—C18—C19—F1	179.46 (14)
C9—C12—C13—C6	−2.8 (2)	C17—C18—C19—C20	0.1 (3)
C10—C12—C13—C6	171.68 (13)	F1—C19—C20—C21	179.70 (14)
C9—C12—C13—C5	−179.97 (13)	C18—C19—C20—C21	−1.0 (3)
C10—C12—C13—C5	−5.46 (19)	C19—C20—C21—C16	0.0 (2)
C15—C5—C13—C6	34.1 (2)	C17—C16—C21—C20	1.7 (2)
C14—C5—C13—C6	−150.10 (13)	C15—C16—C21—C20	177.59 (14)