(E,E)-2-(4-Fluoro­phenyl­methyl­ene)-6-(4-nitro­phenyl­methyl­ene)cyclo­hexa­none

Both olefinic double bonds of the title compound, C₂₀H₁₆FNO₃, have the E configuration, while the cyclo­hex­yl ring adopts the sofa conformation. Non-bonded inter­actions occur between one of the ortho H atoms of each of the ar­yl rings and the equatorial H atoms at positions 3 and 5 of the alicyclic ring.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.058
• wR factor = 0.135
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

(E,E)-2-(4-Fluorophenylmethylene)-6-(4-nitrophenylmethylene)cyclohexanone

Crystal data

C20H16FNO3	F(000) = 704
Mr = 337.34	Dx = 1.389 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3586 reflections
a = 15.5155 (7) Å	θ = 1.0–27.5°
b = 13.6328 (9) Å	µ = 0.10 mm^−1
c = 7.7777 (6) Å	T = 173 K
β = 101.344 (3)°	Plate, yellow
V = 1613.13 (18) Å^3	0.20 × 0.15 × 0.02 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer	1813 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.063
Horizonally mounted graphite crystal monochromator	θmax = 25.4°, θmin = 2.7°
Detector resolution: 9 pixels mm^-1	h = −18→18
φ scans, and ω scans with κ offsets	k = −16→16
5468 measured reflections	l = −9→9
2950 independent reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 0.7039P] where P = (Fo^2 + 2Fc^2)/3
2950 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

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
O1	0.16182 (11)	0.36457 (14)	0.4342 (3)	0.0330 (5)
O2	0.65289 (14)	0.02290 (17)	0.3809 (3)	0.0524 (7)
O3	0.57014 (15)	−0.06739 (19)	0.1874 (3)	0.0582 (7)
F1	−0.34765 (11)	0.32189 (14)	0.5951 (3)	0.0600 (6)
N1	0.58129 (16)	0.0017 (2)	0.2902 (4)	0.0392 (6)
C1	0.14283 (17)	0.2770 (2)	0.4301 (4)	0.0279 (6)
C2	0.05608 (16)	0.2433 (2)	0.4684 (4)	0.0285 (6)
C3	0.04139 (17)	0.1351 (2)	0.4915 (4)	0.0323 (7)
H3A	0.0004	0.1103	0.3866	0.039*
H3B	0.0131	0.1257	0.5938	0.039*
C4	0.12538 (18)	0.0749 (2)	0.5185 (4)	0.0341 (7)
H4A	0.1107	0.0042	0.5180	0.041*
H4B	0.1624	0.0909	0.6339	0.041*
C5	0.17620 (17)	0.0960 (2)	0.3743 (4)	0.0315 (7)
H5A	0.2280	0.0523	0.3876	0.038*
H5B	0.1384	0.0832	0.2584	0.038*
C6	0.20561 (16)	0.2014 (2)	0.3852 (4)	0.0272 (6)
C7	0.28576 (16)	0.2333 (2)	0.3697 (4)	0.0293 (7)
H7	0.2953	0.3021	0.3796	0.035*
C8	0.36036 (17)	0.1738 (2)	0.3390 (4)	0.0285 (7)
C9	0.44450 (18)	0.1996 (2)	0.4292 (4)	0.0350 (7)
H9	0.4522	0.2562	0.5018	0.042*
C10	0.51678 (18)	0.1429 (2)	0.4131 (4)	0.0370 (7)
H10	0.5738	0.1596	0.4759	0.044*
C11	0.50462 (17)	0.0625 (2)	0.3050 (4)	0.0328 (7)
C12	0.42310 (18)	0.0361 (2)	0.2096 (4)	0.0347 (7)
H12	0.4166	−0.0194	0.1343	0.042*
C13	0.35123 (18)	0.0926 (2)	0.2267 (4)	0.0320 (7)
H13	0.2948	0.0760	0.1612	0.038*
C14	−0.00263 (18)	0.3146 (2)	0.4791 (4)	0.0311 (7)
H14	0.0182	0.3789	0.4639	0.037*
C15	−0.09286 (17)	0.3113 (2)	0.5098 (4)	0.0325 (7)
C16	−0.13098 (18)	0.3994 (2)	0.5482 (4)	0.0351 (7)
H16	−0.0975	0.4581	0.5536	0.042*
C17	−0.21601 (18)	0.4041 (2)	0.5785 (4)	0.0373 (7)
H17	−0.2409	0.4644	0.6060	0.045*
C18	−0.26254 (18)	0.3185 (2)	0.5674 (4)	0.0414 (8)
C19	−0.22957 (19)	0.2305 (2)	0.5274 (5)	0.0518 (10)
H19	−0.2644	0.1727	0.5198	0.062*
C20	−0.14498 (18)	0.2270 (2)	0.4985 (5)	0.0450 (9)
H20	−0.1215	0.1661	0.4702	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0308 (10)	0.0252 (11)	0.0444 (13)	−0.0020 (8)	0.0108 (9)	0.0013 (9)
O2	0.0323 (12)	0.0538 (16)	0.0703 (18)	0.0074 (10)	0.0077 (11)	0.0088 (12)
O3	0.0586 (15)	0.0592 (17)	0.0587 (17)	0.0195 (12)	0.0163 (12)	−0.0102 (14)
F1	0.0301 (9)	0.0595 (13)	0.0954 (17)	−0.0073 (9)	0.0249 (10)	−0.0256 (11)
N1	0.0393 (16)	0.0392 (16)	0.0421 (17)	0.0095 (12)	0.0151 (13)	0.0090 (14)
C1	0.0259 (14)	0.0282 (16)	0.0282 (17)	−0.0018 (12)	0.0018 (11)	−0.0010 (12)
C2	0.0266 (14)	0.0277 (16)	0.0309 (18)	−0.0030 (12)	0.0047 (12)	−0.0014 (12)
C3	0.0327 (15)	0.0289 (16)	0.0380 (18)	−0.0053 (12)	0.0135 (13)	−0.0020 (13)
C4	0.0345 (15)	0.0260 (16)	0.0420 (19)	−0.0021 (13)	0.0081 (13)	0.0020 (13)
C5	0.0279 (14)	0.0262 (15)	0.0403 (18)	0.0006 (12)	0.0064 (12)	−0.0011 (13)
C6	0.0257 (14)	0.0272 (16)	0.0284 (17)	0.0012 (11)	0.0049 (11)	0.0027 (12)
C7	0.0305 (15)	0.0277 (15)	0.0294 (17)	0.0003 (12)	0.0053 (12)	0.0009 (12)
C8	0.0277 (14)	0.0271 (15)	0.0331 (17)	−0.0001 (12)	0.0120 (12)	0.0050 (13)
C9	0.0322 (16)	0.0333 (17)	0.042 (2)	−0.0029 (13)	0.0127 (13)	−0.0037 (14)
C10	0.0260 (15)	0.0380 (17)	0.048 (2)	−0.0034 (13)	0.0087 (13)	−0.0001 (15)
C11	0.0285 (15)	0.0349 (17)	0.0385 (19)	0.0043 (13)	0.0149 (13)	0.0071 (14)
C12	0.0389 (17)	0.0373 (17)	0.0294 (18)	0.0015 (14)	0.0103 (13)	−0.0022 (14)
C13	0.0289 (15)	0.0383 (17)	0.0289 (17)	0.0024 (13)	0.0063 (12)	−0.0015 (13)
C14	0.0298 (14)	0.0259 (15)	0.0375 (18)	−0.0020 (12)	0.0059 (12)	−0.0011 (13)
C15	0.0258 (14)	0.0321 (17)	0.0389 (19)	−0.0012 (13)	0.0047 (12)	−0.0032 (14)
C16	0.0298 (15)	0.0300 (16)	0.044 (2)	−0.0009 (13)	0.0045 (13)	0.0000 (14)
C17	0.0327 (16)	0.0315 (17)	0.047 (2)	0.0060 (13)	0.0070 (14)	−0.0050 (14)
C18	0.0225 (14)	0.051 (2)	0.053 (2)	−0.0021 (14)	0.0126 (14)	−0.0138 (16)
C19	0.0336 (17)	0.0379 (19)	0.088 (3)	−0.0117 (15)	0.0210 (17)	−0.0213 (19)
C20	0.0308 (16)	0.0318 (17)	0.074 (3)	−0.0025 (14)	0.0148 (16)	−0.0151 (17)

Geometric parameters (Å, º)

O1—C1	1.229 (3)	C8—C13	1.401 (4)
O2—N1	1.228 (3)	C9—C10	1.388 (4)
O3—N1	1.226 (3)	C9—H9	0.9500
F1—C18	1.380 (3)	C10—C11	1.372 (4)
N1—C11	1.473 (4)	C10—H10	0.9500
C1—C6	1.505 (4)	C11—C12	1.383 (4)
C1—C2	1.506 (4)	C12—C13	1.383 (4)
C2—C14	1.346 (4)	C12—H12	0.9500
C2—C3	1.509 (4)	C13—H13	0.9500
C3—C4	1.520 (4)	C14—C15	1.466 (4)
C3—H3A	0.9900	C14—H14	0.9500
C3—H3B	0.9900	C15—C16	1.397 (4)
C4—C5	1.520 (4)	C15—C20	1.398 (4)
C4—H4A	0.9900	C16—C17	1.387 (4)
C4—H4B	0.9900	C16—H16	0.9500
C5—C6	1.505 (4)	C17—C18	1.365 (4)
C5—H5A	0.9900	C17—H17	0.9500
C5—H5B	0.9900	C18—C19	1.365 (4)
C6—C7	1.345 (4)	C19—C20	1.376 (4)
C7—C8	1.471 (4)	C19—H19	0.9500
C7—H7	0.9500	C20—H20	0.9500
C8—C9	1.400 (4)
O3—N1—O2	123.4 (3)	C10—C9—C8	120.4 (3)
O3—N1—C11	118.1 (3)	C10—C9—H9	119.8
O2—N1—C11	118.4 (3)	C8—C9—H9	119.8
O1—C1—C6	120.5 (2)	C11—C10—C9	119.0 (3)
O1—C1—C2	120.7 (2)	C11—C10—H10	120.5
C6—C1—C2	118.8 (2)	C9—C10—H10	120.5
C14—C2—C1	115.7 (2)	C10—C11—C12	122.6 (3)
C14—C2—C3	125.4 (2)	C10—C11—N1	118.8 (3)
C1—C2—C3	118.9 (2)	C12—C11—N1	118.6 (3)
C2—C3—C4	113.5 (2)	C11—C12—C13	118.2 (3)
C2—C3—H3A	108.9	C11—C12—H12	120.9
C4—C3—H3A	108.9	C13—C12—H12	120.9
C2—C3—H3B	108.9	C12—C13—C8	121.1 (3)
C4—C3—H3B	108.9	C12—C13—H13	119.5
H3A—C3—H3B	107.7	C8—C13—H13	119.5
C3—C4—C5	110.5 (2)	C2—C14—C15	131.8 (3)
C3—C4—H4A	109.5	C2—C14—H14	114.1
C5—C4—H4A	109.5	C15—C14—H14	114.1
C3—C4—H4B	109.5	C16—C15—C20	117.2 (3)
C5—C4—H4B	109.5	C16—C15—C14	117.8 (2)
H4A—C4—H4B	108.1	C20—C15—C14	125.1 (3)
C6—C5—C4	109.6 (2)	C17—C16—C15	122.2 (3)
C6—C5—H5A	109.8	C17—C16—H16	118.9
C4—C5—H5A	109.8	C15—C16—H16	118.9
C6—C5—H5B	109.8	C18—C17—C16	117.3 (3)
C4—C5—H5B	109.8	C18—C17—H17	121.4
H5A—C5—H5B	108.2	C16—C17—H17	121.4
C7—C6—C5	125.4 (2)	C19—C18—C17	123.3 (3)
C7—C6—C1	116.8 (2)	C19—C18—F1	118.5 (3)
C5—C6—C1	117.6 (2)	C17—C18—F1	118.2 (3)
C6—C7—C8	127.4 (3)	C18—C19—C20	118.7 (3)
C6—C7—H7	116.3	C18—C19—H19	120.7
C8—C7—H7	116.3	C20—C19—H19	120.7
C9—C8—C13	118.8 (2)	C19—C20—C15	121.3 (3)
C9—C8—C7	117.8 (3)	C19—C20—H20	119.3
C13—C8—C7	123.4 (2)	C15—C20—H20	119.3
O1—C1—C2—C14	10.0 (4)	O3—N1—C11—C10	−176.9 (3)
C6—C1—C2—C14	−169.5 (3)	O2—N1—C11—C10	3.0 (4)
O1—C1—C2—C3	−170.0 (3)	O3—N1—C11—C12	3.3 (4)
C6—C1—C2—C3	10.5 (4)	O2—N1—C11—C12	−176.8 (3)
C14—C2—C3—C4	−165.3 (3)	C10—C11—C12—C13	−1.0 (4)
C1—C2—C3—C4	14.7 (4)	N1—C11—C12—C13	178.9 (3)
C2—C3—C4—C5	−52.2 (3)	C11—C12—C13—C8	−0.7 (4)
C3—C4—C5—C6	64.2 (3)	C9—C8—C13—C12	2.6 (4)
C4—C5—C6—C7	136.4 (3)	C7—C8—C13—C12	−176.6 (3)
C4—C5—C6—C1	−38.9 (3)	C1—C2—C14—C15	178.5 (3)
O1—C1—C6—C7	7.1 (4)	C3—C2—C14—C15	−1.5 (5)
C2—C1—C6—C7	−173.4 (2)	C2—C14—C15—C16	167.5 (3)
O1—C1—C6—C5	−177.2 (3)	C2—C14—C15—C20	−14.6 (5)
C2—C1—C6—C5	2.3 (4)	C20—C15—C16—C17	1.6 (5)
C5—C6—C7—C8	0.1 (5)	C14—C15—C16—C17	179.7 (3)
C1—C6—C7—C8	175.5 (3)	C15—C16—C17—C18	−0.8 (5)
C6—C7—C8—C9	−140.3 (3)	C16—C17—C18—C19	−0.4 (5)
C6—C7—C8—C13	38.9 (4)	C16—C17—C18—F1	−179.2 (3)
C13—C8—C9—C10	−2.8 (4)	C17—C18—C19—C20	0.7 (6)
C7—C8—C9—C10	176.4 (3)	F1—C18—C19—C20	179.5 (3)
C8—C9—C10—C11	1.2 (4)	C18—C19—C20—C15	0.2 (5)
C9—C10—C11—C12	0.7 (5)	C16—C15—C20—C19	−1.3 (5)
C9—C10—C11—N1	−179.1 (3)	C14—C15—C20—C19	−179.2 (3)