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

Both olefinic bonds in the title compound, C₂₁H₁₉NO₃, possess an E configuration, while the cyclo­hexyl ring adopts a sofa conformation. The aryl rings are not coplanar with the adjacent olefinic groups due to non-bonded interactions between the ortho H atoms of the aryl rings and the equatorial H atoms at positions 3 and 5 of the cyclo­hexyl ring.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.130
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

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Computing details

Data collection: COLLECT (Nonius, 2000); 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-Methylphenylmethylene)-6-(4-nitrophenylmethylene)cyclohexanone

Crystal data

C21H19NO3	F(000) = 704
Mr = 333.37	Dx = 1.354 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4997 reflections
a = 7.5713 (3) Å	θ = 1.0–30.0°
b = 10.9972 (4) Å	µ = 0.09 mm^−1
c = 20.0451 (6) Å	T = 173 K
β = 101.550 (2)°	Chip, yellow
V = 1635.22 (10) Å^3	0.25 × 0.15 × 0.10 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2252 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Horizonally mounted graphite crystal monochromator	θmax = 26.4°, θmin = 2.8°
Detector resolution: 9 pixels mm^-1	h = −9→9
φ scans and ω scans with κ offsets	k = −13→13
6518 measured reflections	l = −24→24
3354 independent reflections

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)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.0621P)^2 + 0.3697P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3354 reflections	Δρmax = 0.26 e Å^−3
228 parameters	Δρmin = −0.24 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: 0.0110 (18)

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
N1	1.0235 (2)	0.92058 (17)	0.85261 (8)	0.0387 (4)
O1	0.7513 (2)	1.02782 (14)	0.43299 (7)	0.0503 (4)
O2	1.1505 (2)	0.98567 (15)	0.87954 (7)	0.0514 (4)
O3	0.9576 (2)	0.84253 (17)	0.88339 (8)	0.0577 (5)
C1	0.6773 (3)	0.93328 (17)	0.44521 (9)	0.0308 (4)
C2	0.5697 (2)	0.85971 (17)	0.38862 (9)	0.0274 (4)
C3	0.4876 (3)	0.74196 (17)	0.40561 (9)	0.0328 (5)
H3A	0.4835	0.6841	0.3675	0.039*
H3B	0.3622	0.7570	0.4109	0.039*
C4	0.5940 (3)	0.68561 (18)	0.47078 (9)	0.0362 (5)
H4A	0.5331	0.6102	0.4810	0.043*
H4B	0.7159	0.6635	0.4640	0.043*
C5	0.6108 (3)	0.77195 (17)	0.53077 (9)	0.0327 (5)
H5A	0.4897	0.7860	0.5409	0.039*
H5B	0.6866	0.7336	0.5713	0.039*
C6	0.6921 (2)	0.89241 (17)	0.51783 (9)	0.0282 (4)
C7	0.7803 (2)	0.96795 (17)	0.56568 (9)	0.0289 (4)
H7	0.8190	1.0418	0.5486	0.035*
C8	0.8266 (2)	0.95536 (17)	0.63999 (9)	0.0276 (4)
C9	0.9636 (2)	1.03177 (18)	0.67446 (10)	0.0314 (4)
H9	1.0144	1.0910	0.6494	0.038*
C10	1.0262 (2)	1.02299 (18)	0.74380 (9)	0.0321 (5)
H10	1.1188	1.0754	0.7665	0.039*
C11	0.9512 (2)	0.93627 (18)	0.77961 (9)	0.0295 (4)
C12	0.8099 (3)	0.86285 (18)	0.74860 (9)	0.0322 (5)
H12	0.7573	0.8059	0.7745	0.039*
C13	0.7467 (2)	0.87400 (18)	0.67903 (9)	0.0312 (5)
H13	0.6475	0.8258	0.6574	0.037*
C14	0.5531 (2)	0.90804 (17)	0.32576 (9)	0.0270 (4)
H14	0.6214	0.9802	0.3247	0.032*
C15	0.4507 (2)	0.87149 (16)	0.25886 (9)	0.0254 (4)
C16	0.4833 (3)	0.93674 (17)	0.20244 (9)	0.0310 (5)
H16	0.5752	0.9969	0.2091	0.037*
C17	0.3858 (3)	0.91613 (18)	0.13736 (9)	0.0322 (5)
H17	0.4130	0.9617	0.1005	0.039*
C18	0.2491 (2)	0.83030 (17)	0.12487 (9)	0.0292 (4)
C19	0.2194 (3)	0.76272 (18)	0.18041 (10)	0.0331 (5)
H19	0.1298	0.7010	0.1732	0.040*
C20	0.3160 (2)	0.78244 (18)	0.24571 (9)	0.0314 (4)
H20	0.2906	0.7348	0.2822	0.038*
C21	0.1338 (3)	0.8143 (2)	0.05507 (10)	0.0380 (5)
H21A	0.1065	0.7279	0.0469	0.046*
H21B	0.1986	0.8449	0.0208	0.046*
H21C	0.0212	0.8599	0.0521	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0393 (10)	0.0483 (11)	0.0271 (9)	0.0083 (9)	0.0036 (8)	−0.0035 (8)
O1	0.0737 (11)	0.0446 (10)	0.0299 (8)	−0.0294 (8)	0.0040 (7)	0.0013 (7)
O2	0.0465 (9)	0.0682 (11)	0.0333 (8)	−0.0032 (8)	−0.0065 (7)	−0.0062 (7)
O3	0.0703 (11)	0.0708 (12)	0.0306 (8)	−0.0078 (9)	0.0069 (8)	0.0103 (8)
C1	0.0337 (10)	0.0302 (11)	0.0283 (10)	−0.0029 (8)	0.0056 (8)	0.0000 (8)
C2	0.0282 (9)	0.0284 (10)	0.0251 (9)	0.0013 (8)	0.0043 (8)	−0.0024 (8)
C3	0.0432 (11)	0.0275 (11)	0.0262 (10)	−0.0048 (8)	0.0035 (9)	−0.0026 (8)
C4	0.0526 (13)	0.0274 (11)	0.0278 (10)	−0.0028 (9)	0.0062 (9)	0.0014 (8)
C5	0.0415 (11)	0.0309 (11)	0.0255 (10)	−0.0027 (9)	0.0061 (8)	−0.0001 (8)
C6	0.0274 (9)	0.0322 (11)	0.0247 (9)	0.0019 (8)	0.0045 (8)	0.0005 (8)
C7	0.0294 (9)	0.0296 (10)	0.0268 (10)	0.0012 (8)	0.0039 (8)	0.0009 (8)
C8	0.0278 (9)	0.0275 (10)	0.0265 (10)	0.0049 (8)	0.0030 (8)	−0.0026 (8)
C9	0.0334 (10)	0.0303 (11)	0.0303 (10)	−0.0016 (8)	0.0059 (8)	−0.0001 (8)
C10	0.0314 (10)	0.0338 (11)	0.0297 (10)	0.0008 (8)	0.0028 (8)	−0.0063 (8)
C11	0.0303 (10)	0.0347 (11)	0.0228 (9)	0.0078 (8)	0.0040 (8)	−0.0025 (8)
C12	0.0348 (10)	0.0370 (11)	0.0263 (10)	0.0024 (9)	0.0093 (8)	−0.0011 (8)
C13	0.0305 (10)	0.0349 (11)	0.0285 (10)	0.0008 (8)	0.0066 (8)	−0.0035 (8)
C14	0.0256 (9)	0.0261 (10)	0.0288 (10)	−0.0002 (7)	0.0042 (8)	0.0009 (8)
C15	0.0256 (9)	0.0251 (10)	0.0243 (9)	0.0031 (7)	0.0027 (7)	0.0004 (7)
C16	0.0328 (10)	0.0296 (11)	0.0297 (10)	−0.0025 (8)	0.0038 (8)	0.0018 (8)
C17	0.0381 (11)	0.0324 (11)	0.0261 (10)	0.0019 (9)	0.0063 (8)	0.0034 (8)
C18	0.0314 (10)	0.0288 (10)	0.0260 (10)	0.0052 (8)	0.0024 (8)	−0.0011 (8)
C19	0.0317 (10)	0.0332 (11)	0.0325 (11)	−0.0047 (8)	0.0019 (8)	−0.0009 (8)
C20	0.0317 (10)	0.0332 (11)	0.0288 (10)	−0.0030 (8)	0.0043 (8)	0.0042 (8)
C21	0.0404 (11)	0.0400 (12)	0.0304 (11)	0.0041 (9)	−0.0007 (9)	−0.0031 (9)

Geometric parameters (Å, º)

N1—O3	1.220 (2)	C9—H9	0.9500
N1—O2	1.233 (2)	C10—C11	1.382 (3)
N1—C11	1.466 (2)	C10—H10	0.9500
O1—C1	1.229 (2)	C11—C12	1.385 (3)
C1—C2	1.495 (3)	C12—C13	1.386 (3)
C1—C6	1.506 (3)	C12—H12	0.9500
C2—C14	1.350 (3)	C13—H13	0.9500
C2—C3	1.505 (3)	C14—C15	1.464 (2)
C3—C4	1.523 (3)	C14—H14	0.9500
C3—H3A	0.9900	C15—C20	1.400 (3)
C3—H3B	0.9900	C15—C16	1.402 (3)
C4—C5	1.517 (3)	C16—C17	1.383 (3)
C4—H4A	0.9900	C16—H16	0.9500
C4—H4B	0.9900	C17—C18	1.386 (3)
C5—C6	1.505 (3)	C17—H17	0.9500
C5—H5A	0.9900	C18—C19	1.394 (3)
C5—H5B	0.9900	C18—C21	1.504 (3)
C6—C7	1.341 (3)	C19—C20	1.383 (3)
C7—C8	1.467 (2)	C19—H19	0.9500
C7—H7	0.9500	C20—H20	0.9500
C8—C13	1.403 (3)	C21—H21A	0.9800
C8—C9	1.404 (3)	C21—H21B	0.9800
C9—C10	1.379 (3)	C21—H21C	0.9800
O3—N1—O2	123.29 (17)	C9—C10—C11	118.54 (17)
O3—N1—C11	118.60 (17)	C9—C10—H10	120.7
O2—N1—C11	118.09 (18)	C11—C10—H10	120.7
O1—C1—C2	120.51 (17)	C10—C11—C12	122.01 (17)
O1—C1—C6	119.77 (17)	C10—C11—N1	119.32 (17)
C2—C1—C6	119.71 (16)	C12—C11—N1	118.67 (18)
C14—C2—C1	115.47 (17)	C11—C12—C13	118.70 (18)
C14—C2—C3	125.76 (16)	C11—C12—H12	120.6
C1—C2—C3	118.76 (16)	C13—C12—H12	120.6
C2—C3—C4	111.88 (15)	C12—C13—C8	121.11 (17)
C2—C3—H3A	109.2	C12—C13—H13	119.4
C4—C3—H3A	109.2	C8—C13—H13	119.4
C2—C3—H3B	109.2	C2—C14—C15	132.85 (18)
C4—C3—H3B	109.2	C2—C14—H14	113.6
H3A—C3—H3B	107.9	C15—C14—H14	113.6
C5—C4—C3	111.79 (16)	C20—C15—C16	116.43 (16)
C5—C4—H4A	109.3	C20—C15—C14	126.62 (16)
C3—C4—H4A	109.3	C16—C15—C14	116.85 (16)
C5—C4—H4B	109.3	C17—C16—C15	121.99 (18)
C3—C4—H4B	109.3	C17—C16—H16	119.0
H4A—C4—H4B	107.9	C15—C16—H16	119.0
C6—C5—C4	112.73 (15)	C16—C17—C18	121.36 (18)
C6—C5—H5A	109.0	C16—C17—H17	119.3
C4—C5—H5A	109.0	C18—C17—H17	119.3
C6—C5—H5B	109.0	C17—C18—C19	116.93 (17)
C4—C5—H5B	109.0	C17—C18—C21	121.39 (17)
H5A—C5—H5B	107.8	C19—C18—C21	121.64 (17)
C7—C6—C5	125.73 (17)	C20—C19—C18	122.23 (18)
C7—C6—C1	115.88 (17)	C20—C19—H19	118.9
C5—C6—C1	118.39 (16)	C18—C19—H19	118.9
C6—C7—C8	130.65 (18)	C19—C20—C15	121.01 (17)
C6—C7—H7	114.7	C19—C20—H20	119.5
C8—C7—H7	114.7	C15—C20—H20	119.5
C13—C8—C9	117.76 (16)	C18—C21—H21A	109.5
C13—C8—C7	125.74 (16)	C18—C21—H21B	109.5
C9—C8—C7	116.50 (17)	H21A—C21—H21B	109.5
C10—C9—C8	121.66 (18)	C18—C21—H21C	109.5
C10—C9—H9	119.2	H21A—C21—H21C	109.5
C8—C9—H9	119.2	H21B—C21—H21C	109.5
O1—C1—C2—C14	−3.5 (3)	O3—N1—C11—C10	−179.01 (18)
C6—C1—C2—C14	175.30 (16)	O2—N1—C11—C10	−0.4 (3)
O1—C1—C2—C3	177.55 (19)	O3—N1—C11—C12	0.7 (3)
C6—C1—C2—C3	−3.6 (3)	O2—N1—C11—C12	179.32 (17)
C14—C2—C3—C4	154.16 (18)	C10—C11—C12—C13	2.4 (3)
C1—C2—C3—C4	−27.1 (2)	N1—C11—C12—C13	−177.26 (16)
C2—C3—C4—C5	56.9 (2)	C11—C12—C13—C8	1.8 (3)
C3—C4—C5—C6	−55.5 (2)	C9—C8—C13—C12	−4.8 (3)
C4—C5—C6—C7	−155.15 (19)	C7—C8—C13—C12	175.02 (18)
C4—C5—C6—C1	24.0 (2)	C1—C2—C14—C15	−174.69 (18)
O1—C1—C6—C7	3.4 (3)	C3—C2—C14—C15	4.1 (3)
C2—C1—C6—C7	−175.43 (16)	C2—C14—C15—C20	11.5 (3)
O1—C1—C6—C5	−175.85 (18)	C2—C14—C15—C16	−172.4 (2)
C2—C1—C6—C5	5.3 (3)	C20—C15—C16—C17	1.2 (3)
C5—C6—C7—C8	2.3 (3)	C14—C15—C16—C17	−175.38 (17)
C1—C6—C7—C8	−176.94 (17)	C15—C16—C17—C18	0.7 (3)
C6—C7—C8—C13	−18.2 (3)	C16—C17—C18—C19	−2.4 (3)
C6—C7—C8—C9	161.64 (19)	C16—C17—C18—C21	175.36 (18)
C13—C8—C9—C10	3.9 (3)	C17—C18—C19—C20	2.4 (3)
C7—C8—C9—C10	−175.98 (17)	C21—C18—C19—C20	−175.34 (18)
C8—C9—C10—C11	0.1 (3)	C18—C19—C20—C15	−0.6 (3)
C9—C10—C11—C12	−3.4 (3)	C16—C15—C20—C19	−1.2 (3)
C9—C10—C11—N1	176.32 (17)	C14—C15—C20—C19	174.99 (18)