(E,E,E)-1,6-Bis(4-nitro­phen­yl)hexa-1,3,5-triene

In the title compound, C₁₈H₁₄N₂O₄, the torsion angles of the single bonds between the hexa­triene chain and 4-nitro­phen­yl rings are 18.0 (2) and −0.7 (2)°. The mol­ecules are linked weakly via inter­molecular C—H...O hydrogen bonds to form sheets. These sheets are linked further by N...O dipole inter­actions between the nitro groups and aromatic π–π stacking inter­actions, to form a three-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.126
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15    ..  O1      ..       2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  O1      ..       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  O4      ..       2.97 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  O4      ..       2.92 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: TEXSAN (Molecular Structure Corporation, 1999); software used to prepare material for publication: SHELXTL.

(E,E,E)-1,6-Bis(4-nitrophenyl)hexa-1,3,5-triene

Crystal data

C18H14N2O4	Dx = 1.385 Mg m^−3
Mr = 322.31	Melting point: 513-514 K K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 3.8710 (4) Å	Cell parameters from 3502 reflections
b = 21.440 (2) Å	θ = 2.2–28.1°
c = 18.7091 (19) Å	µ = 0.10 mm^−1
β = 95.555 (2)°	T = 183 K
V = 1545.4 (3) Å^3	Needle, yellow
Z = 4	0.30 × 0.25 × 0.02 mm
F(000) = 672

Data collection

Bruker SMART CCD area-detector diffractometer	3490 independent reflections
Radiation source: rotating anode	2640 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.366 pixels mm^-1	θmax = 28.2°, θmin = 1.5°
φ and ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −28→20
Tmin = 0.909, Tmax = 0.998	l = −22→23
9325 measured 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)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.126	w = 1/[σ^2(Fo^2) + (0.0743P)^2 + 0.088P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.002
3490 reflections	Δρmax = 0.24 e Å^−3
218 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2000), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0075 (15)

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
C1	1.3424 (3)	0.59348 (6)	0.59861 (8)	0.0368 (3)
C2	1.2112 (4)	0.57741 (7)	0.52994 (8)	0.0411 (3)
H2	1.2433	0.5365	0.5122	0.049*
C3	1.0328 (4)	0.62165 (6)	0.48752 (8)	0.0383 (3)
H3	0.9380	0.6107	0.4404	0.046*
C4	0.9889 (3)	0.68226 (6)	0.51257 (7)	0.0312 (3)
C5	1.1238 (3)	0.69624 (6)	0.58283 (7)	0.0351 (3)
H5	1.0933	0.7370	0.6010	0.042*
C6	1.2997 (3)	0.65251 (6)	0.62640 (7)	0.0376 (3)
H6	1.3889	0.6626	0.6741	0.045*
C7	0.8069 (3)	0.72819 (6)	0.46529 (7)	0.0342 (3)
H7	0.6665	0.7127	0.4247	0.041*
C8	0.8196 (3)	0.79021 (6)	0.47386 (7)	0.0351 (3)
H8	0.9540	0.8061	0.5151	0.042*
C9	0.6449 (3)	0.83450 (7)	0.42533 (7)	0.0366 (3)
H9	0.5023	0.8192	0.3850	0.044*
C10	0.6736 (3)	0.89643 (6)	0.43431 (7)	0.0364 (3)
H10	0.8143	0.9109	0.4754	0.044*
C11	0.5088 (3)	0.94263 (6)	0.38688 (7)	0.0356 (3)
H11	0.3669	0.9289	0.3456	0.043*
C12	0.5458 (3)	1.00413 (6)	0.39816 (7)	0.0348 (3)
H12	0.6851	1.0162	0.4405	0.042*
C13	0.3969 (3)	1.05453 (6)	0.35289 (7)	0.0309 (3)
C14	0.1893 (3)	1.04421 (6)	0.28848 (7)	0.0335 (3)
H14	0.1388	1.0026	0.2733	0.040*
C15	0.0565 (3)	1.09322 (6)	0.24656 (7)	0.0346 (3)
H15	−0.0838	1.0857	0.2029	0.042*
C16	0.1322 (3)	1.15352 (6)	0.26948 (7)	0.0330 (3)
C17	0.3357 (3)	1.16595 (6)	0.33257 (7)	0.0346 (3)
H17	0.3859	1.2077	0.3472	0.042*
C18	0.4648 (3)	1.11635 (6)	0.37400 (7)	0.0338 (3)
H18	0.6029	1.1243	0.4178	0.041*
N1	1.5364 (3)	0.54706 (6)	0.64365 (8)	0.0488 (3)
N2	−0.0165 (3)	1.20575 (6)	0.22655 (6)	0.0422 (3)
O1	1.5715 (4)	0.49480 (6)	0.61881 (8)	0.0742 (4)
O2	1.6594 (3)	0.56252 (6)	0.70385 (7)	0.0640 (4)
O3	−0.2134 (3)	1.19414 (6)	0.17311 (6)	0.0576 (3)
O4	0.0580 (4)	1.25883 (5)	0.24665 (7)	0.0678 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0332 (6)	0.0355 (7)	0.0426 (8)	0.0036 (5)	0.0078 (6)	0.0109 (6)
C2	0.0471 (8)	0.0300 (7)	0.0470 (8)	0.0017 (6)	0.0094 (6)	0.0010 (6)
C3	0.0423 (7)	0.0356 (7)	0.0368 (7)	−0.0023 (6)	0.0033 (6)	−0.0020 (6)
C4	0.0262 (6)	0.0329 (7)	0.0347 (7)	−0.0017 (5)	0.0038 (5)	0.0021 (5)
C5	0.0339 (6)	0.0331 (7)	0.0378 (7)	0.0021 (5)	0.0004 (5)	−0.0014 (5)
C6	0.0362 (7)	0.0410 (8)	0.0349 (7)	0.0011 (6)	0.0006 (5)	0.0031 (6)
C7	0.0296 (6)	0.0392 (8)	0.0331 (7)	−0.0001 (5)	−0.0009 (5)	0.0003 (5)
C8	0.0298 (6)	0.0382 (7)	0.0366 (7)	−0.0002 (5)	0.0002 (5)	0.0031 (6)
C9	0.0317 (6)	0.0418 (8)	0.0360 (7)	0.0021 (6)	0.0011 (5)	0.0044 (6)
C10	0.0324 (6)	0.0392 (8)	0.0373 (7)	0.0012 (5)	0.0015 (5)	0.0051 (6)
C11	0.0316 (6)	0.0402 (8)	0.0349 (7)	0.0008 (6)	0.0024 (5)	0.0036 (6)
C12	0.0302 (6)	0.0399 (8)	0.0336 (7)	−0.0014 (5)	−0.0002 (5)	0.0021 (5)
C13	0.0254 (5)	0.0366 (7)	0.0310 (6)	0.0007 (5)	0.0038 (5)	0.0018 (5)
C14	0.0333 (6)	0.0344 (7)	0.0326 (7)	−0.0011 (5)	0.0027 (5)	−0.0032 (5)
C15	0.0331 (6)	0.0440 (8)	0.0262 (6)	0.0002 (6)	0.0006 (5)	−0.0018 (5)
C16	0.0319 (6)	0.0370 (7)	0.0308 (6)	0.0043 (5)	0.0057 (5)	0.0048 (5)
C17	0.0329 (6)	0.0331 (7)	0.0378 (7)	−0.0025 (5)	0.0038 (5)	−0.0017 (5)
C18	0.0306 (6)	0.0380 (7)	0.0319 (6)	−0.0020 (5)	−0.0011 (5)	−0.0018 (5)
N1	0.0472 (7)	0.0461 (8)	0.0546 (9)	0.0099 (6)	0.0122 (6)	0.0195 (6)
N2	0.0456 (7)	0.0441 (7)	0.0374 (7)	0.0088 (5)	0.0070 (5)	0.0073 (5)
O1	0.1054 (11)	0.0459 (7)	0.0723 (9)	0.0311 (7)	0.0135 (8)	0.0148 (6)
O2	0.0669 (8)	0.0649 (8)	0.0577 (8)	0.0122 (6)	−0.0070 (6)	0.0217 (6)
O3	0.0610 (7)	0.0662 (8)	0.0425 (6)	0.0087 (6)	−0.0101 (5)	0.0134 (5)
O4	0.0983 (10)	0.0381 (7)	0.0641 (8)	0.0119 (6)	−0.0067 (7)	0.0049 (5)

Geometric parameters (Å, º)

C1—C2	1.379 (2)	C11—C12	1.341 (2)
C1—C6	1.384 (2)	C11—H11	0.950
C1—N1	1.463 (2)	C12—C13	1.457 (2)
C2—C3	1.379 (2)	C12—H12	0.950
C2—H2	0.950	C13—C14	1.400 (2)
C3—C4	1.398 (2)	C13—C18	1.401 (2)
C3—H3	0.950	C14—C15	1.381 (2)
C4—C5	1.399 (2)	C14—H14	0.950
C4—C7	1.459 (2)	C15—C16	1.384 (2)
C5—C6	1.378 (2)	C15—H15	0.950
C5—H5	0.950	C16—C17	1.381 (2)
C6—H6	0.950	C16—N2	1.463 (2)
C7—C8	1.340 (2)	C17—C18	1.381 (2)
C7—H7	0.950	C17—H17	0.950
C8—C9	1.437 (2)	C18—H18	0.950
C8—H8	0.950	N1—O2	1.225 (2)
C9—C10	1.342 (2)	N1—O1	1.226 (2)
C9—H9	0.950	N2—O3	1.223 (2)
C10—C11	1.437 (2)	N2—O4	1.224 (2)
C10—H10	0.950
C2—C1—C6	122.1 (1)	C12—C11—C10	123.1 (1)
C2—C1—N1	119.3 (1)	C12—C11—H11	118.4
C6—C1—N1	118.6 (1)	C10—C11—H11	118.4
C3—C2—C1	118.9 (1)	C11—C12—C13	127.4 (1)
C3—C2—H2	120.5	C11—C12—H12	116.3
C1—C2—H2	120.5	C13—C12—H12	116.3
C2—C3—C4	121.2 (1)	C14—C13—C18	118.0 (1)
C2—C3—H3	119.4	C14—C13—C12	123.0 (1)
C4—C3—H3	119.4	C18—C13—C12	119.0 (1)
C3—C4—C5	117.9 (1)	C15—C14—C13	121.3 (1)
C3—C4—C7	119.5 (1)	C15—C14—H14	119.3
C5—C4—C7	122.7 (1)	C13—C14—H14	119.3
C6—C5—C4	121.9 (1)	C14—C15—C16	118.6 (1)
C6—C5—H5	119.1	C14—C15—H15	120.7
C4—C5—H5	119.1	C16—C15—H15	120.7
C5—C6—C1	118.0 (1)	C17—C16—C15	122.1 (1)
C5—C6—H6	121.0	C17—C16—N2	118.9 (1)
C1—C6—H6	121.0	C15—C16—N2	119.0 (1)
C8—C7—C4	126.0 (1)	C16—C17—C18	118.5 (1)
C8—C7—H7	117.0	C16—C17—H17	120.8
C4—C7—H7	117.0	C18—C17—H17	120.8
C7—C8—C9	124.8 (1)	C17—C18—C13	121.5 (1)
C7—C8—H8	117.6	C17—C18—H18	119.2
C9—C8—H8	117.6	C13—C18—H18	119.2
C10—C9—C8	123.2 (1)	O2—N1—O1	123.3 (1)
C10—C9—H9	118.4	O2—N1—C1	118.5 (1)
C8—C9—H9	118.4	O1—N1—C1	118.2 (1)
C9—C10—C11	125.3 (1)	O3—N2—O4	123.4 (1)
C9—C10—H10	117.3	O3—N2—C16	118.3 (1)
C11—C10—H10	117.3	O4—N2—C16	118.3 (1)
C6—C1—C2—C3	0.2 (2)	C18—C13—C14—C15	0.4 (2)
N1—C1—C2—C3	−179.2 (1)	C12—C13—C14—C15	−179.2 (1)
C1—C2—C3—C4	1.1 (2)	C13—C14—C15—C16	−0.1 (2)
C2—C3—C4—C5	−1.7 (2)	C14—C15—C16—C17	0.1 (2)
C2—C3—C4—C7	178.3 (1)	C14—C15—C16—N2	−178.1 (1)
C3—C4—C5—C6	1.0 (2)	C15—C16—C17—C18	−0.4 (2)
C7—C4—C5—C6	−179.0 (1)	N2—C16—C17—C18	177.8 (1)
C4—C5—C6—C1	0.3 (2)	C16—C17—C18—C13	0.8 (2)
C2—C1—C6—C5	−0.9 (2)	C14—C13—C18—C17	−0.7 (2)
N1—C1—C6—C5	178.5 (1)	C12—C13—C18—C17	178.8 (1)
C3—C4—C7—C8	−162.0 (1)	C2—C1—N1—O2	178.1 (1)
C5—C4—C7—C8	18.0 (2)	C6—C1—N1—O2	−1.4 (2)
C4—C7—C8—C9	178.2 (1)	C2—C1—N1—O1	−1.0 (2)
C7—C8—C9—C10	−177.5 (1)	C6—C1—N1—O1	179.6 (1)
C8—C9—C10—C11	179.0 (1)	C17—C16—N2—O3	−175.6 (1)
C9—C10—C11—C12	−179.9 (1)	C15—C16—N2—O3	2.7 (2)
C10—C11—C12—C13	178.6 (1)	C17—C16—N2—O4	3.2 (2)
C11—C12—C13—C14	−0.7 (2)	C15—C16—N2—O4	−178.6 (1)
C11—C12—C13—C18	179.8 (1)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3^i	0.95	2.44	3.371 (2)	166
C14—H14···O2^ii	0.95	2.57	3.366 (2)	141
C15—H15···O1^ii	0.95	2.61	3.454 (2)	148
C2—H2···O1^iii	0.95	2.71	3.364 (2)	127
C5—H5···O4^iv	0.95	2.97	3.470 (2)	115
C6—H6···O4^iv	0.95	2.92	3.437 (2)	115

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