Mol­ecular and crystal structure, optical properties and DFT studies of 1,4-dimeth­oxy-2,5-bis­[2-(4-nitro­phen­yl)ethen­yl]benzene

In the title mol­ecule, which is based on a 1,4-distyryl-2,5-di­meth­oxy­benzene core with p-nitro-substituted terminal benzene rings, the dihedral angle between mean planes of the central fragment and the terminal phenyl ring is 16.46 (6)°. The crystal packing is stabilized by π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.048
• wR factor = 0.145
• Data-to-parameter ratio = 23.7

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Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.29 Report
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.928 Report

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

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


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PUBL024_ALERT_1_A The number of authors is greater than 5.
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   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2017/1 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015b), OLEX2 (Dolomanov et al., 2009); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: Mercury (Macrae et al., 2020).

1,4-Dimethoxy-2,5-bis[2-(4-nitrophenyl)ethenyl]benzene

Crystal data

C24H20N2O6	F(000) = 452
Mr = 432.42	Dx = 1.403 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.9074 (10) Å	Cell parameters from 6481 reflections
b = 12.4794 (16) Å	θ = 2.6–31.3°
c = 10.6248 (14) Å	µ = 0.10 mm^−1
β = 102.394 (3)°	T = 100 K
V = 1024.0 (2) Å^3	Block, red
Z = 2	0.22 × 0.15 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer	2542 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.055
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 31.7°, θmin = 2.6°
Tmin = 0.653, Tmax = 0.746	h = −11→11
32090 measured reflections	k = −18→18
3460 independent reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0723P)^2 + 0.3749P] where P = (Fo^2 + 2Fc^2)/3
3460 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O1	1.12432 (11)	0.50902 (7)	0.27624 (8)	0.0223 (2)
O2	−0.13219 (13)	0.91355 (10)	0.42105 (12)	0.0423 (3)
O3	−0.08612 (15)	0.85312 (11)	0.61675 (12)	0.0453 (3)
N1	−0.04597 (14)	0.86252 (10)	0.51181 (12)	0.0301 (3)
C1	1.05803 (14)	0.50680 (9)	0.38485 (11)	0.0176 (2)
C2	0.90285 (14)	0.55533 (9)	0.39523 (11)	0.0185 (2)
H2	0.836944	0.592801	0.323366	0.022*
C3	0.84235 (14)	0.54988 (9)	0.50948 (11)	0.0178 (2)
C10	0.18811 (15)	0.73214 (10)	0.58176 (12)	0.0215 (2)
H10	0.137655	0.713154	0.652137	0.026*
C4	0.67887 (14)	0.59782 (10)	0.52387 (11)	0.0202 (2)
H4	0.640701	0.580352	0.600263	0.024*
C6	0.41503 (15)	0.71106 (10)	0.46101 (11)	0.0196 (2)
C11	0.33818 (15)	0.68241 (9)	0.56370 (11)	0.0198 (2)
H11	0.389852	0.627975	0.621909	0.024*
C9	0.11358 (14)	0.81049 (10)	0.49411 (12)	0.0217 (2)
C5	0.57748 (16)	0.66340 (10)	0.44141 (12)	0.0225 (2)
H5	0.613011	0.680685	0.363923	0.027*
C8	0.18426 (16)	0.84114 (11)	0.39171 (12)	0.0249 (3)
H8	0.131401	0.895451	0.333775	0.030*
C7	0.33514 (17)	0.79047 (11)	0.37539 (12)	0.0252 (3)
H7	0.384749	0.810152	0.304835	0.030*
C12	1.03435 (16)	0.57061 (12)	0.16982 (12)	0.0269 (3)
H12A	1.097995	0.568337	0.100234	0.040*
H12B	1.025026	0.645017	0.197031	0.040*
H12C	0.918153	0.540834	0.138992	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0212 (4)	0.0287 (5)	0.0177 (4)	0.0069 (3)	0.0058 (3)	0.0033 (3)
O2	0.0253 (5)	0.0519 (7)	0.0485 (7)	0.0170 (5)	0.0054 (5)	0.0069 (5)
O3	0.0363 (6)	0.0580 (8)	0.0491 (7)	0.0163 (5)	0.0260 (5)	0.0067 (6)
N1	0.0192 (5)	0.0331 (6)	0.0387 (6)	0.0057 (4)	0.0082 (4)	−0.0013 (5)
C1	0.0175 (5)	0.0183 (5)	0.0172 (5)	0.0007 (4)	0.0040 (4)	−0.0014 (4)
C2	0.0168 (5)	0.0200 (5)	0.0180 (5)	0.0027 (4)	0.0018 (4)	0.0010 (4)
C3	0.0152 (5)	0.0181 (5)	0.0198 (5)	0.0018 (4)	0.0029 (4)	−0.0014 (4)
C10	0.0191 (5)	0.0228 (6)	0.0237 (5)	−0.0025 (4)	0.0071 (4)	−0.0014 (4)
C4	0.0180 (5)	0.0234 (5)	0.0195 (5)	0.0026 (4)	0.0049 (4)	−0.0007 (4)
C6	0.0167 (5)	0.0211 (5)	0.0206 (5)	0.0023 (4)	0.0033 (4)	−0.0012 (4)
C11	0.0180 (5)	0.0199 (5)	0.0212 (5)	0.0000 (4)	0.0034 (4)	0.0003 (4)
C9	0.0148 (5)	0.0246 (6)	0.0257 (6)	0.0028 (4)	0.0045 (4)	−0.0043 (4)
C5	0.0211 (5)	0.0250 (6)	0.0235 (6)	0.0059 (4)	0.0092 (4)	0.0036 (4)
C8	0.0227 (6)	0.0284 (6)	0.0235 (6)	0.0083 (5)	0.0044 (4)	0.0030 (5)
C7	0.0247 (6)	0.0301 (6)	0.0225 (6)	0.0085 (5)	0.0091 (5)	0.0052 (5)
C12	0.0212 (5)	0.0388 (7)	0.0211 (6)	0.0048 (5)	0.0055 (4)	0.0086 (5)

Geometric parameters (Å, º)

O1—C1	1.3663 (14)	C4—C5	1.3337 (16)
O1—C12	1.4248 (15)	C6—C11	1.4043 (16)
O2—N1	1.2321 (16)	C6—C5	1.4704 (16)
O3—N1	1.2287 (16)	C6—C7	1.4007 (17)
N1—C9	1.4665 (16)	C11—H11	0.9500
C1—C2	1.3938 (15)	C9—C8	1.3796 (18)
C1—C3^i	1.4148 (16)	C5—H5	0.9500
C2—H2	0.9500	C8—H8	0.9500
C2—C3	1.3986 (16)	C8—C7	1.3936 (17)
C3—C4	1.4619 (15)	C7—H7	0.9500
C10—H10	0.9500	C12—H12A	0.9800
C10—C11	1.3885 (16)	C12—H12B	0.9800
C10—C9	1.3910 (17)	C12—H12C	0.9800
C4—H4	0.9500
C1—O1—C12	117.68 (9)	C10—C11—C6	121.25 (11)
O2—N1—C9	118.37 (12)	C10—C11—H11	119.4
O3—N1—O2	123.52 (12)	C6—C11—H11	119.4
O3—N1—C9	118.11 (11)	C10—C9—N1	118.55 (11)
O1—C1—C2	124.19 (10)	C8—C9—N1	118.92 (11)
O1—C1—C3^i	115.54 (10)	C8—C9—C10	122.53 (11)
C2—C1—C3^i	120.27 (10)	C4—C5—C6	125.13 (11)
C1—C2—H2	119.4	C4—C5—H5	117.4
C1—C2—C3	121.23 (10)	C6—C5—H5	117.4
C3—C2—H2	119.4	C9—C8—H8	120.8
C1^i—C3—C4	118.41 (10)	C9—C8—C7	118.35 (11)
C2—C3—C1^i	118.50 (10)	C7—C8—H8	120.8
C2—C3—C4	123.08 (10)	C6—C7—H7	119.4
C11—C10—H10	120.9	C8—C7—C6	121.27 (11)
C11—C10—C9	118.26 (11)	C8—C7—H7	119.4
C9—C10—H10	120.9	O1—C12—H12A	109.5
C3—C4—H4	116.5	O1—C12—H12B	109.5
C5—C4—C3	127.07 (11)	O1—C12—H12C	109.5
C5—C4—H4	116.5	H12A—C12—H12B	109.5
C11—C6—C5	122.95 (11)	H12A—C12—H12C	109.5
C7—C6—C11	118.34 (10)	H12B—C12—H12C	109.5
C7—C6—C5	118.69 (11)
O1—C1—C2—C3	179.95 (11)	C11—C10—C9—N1	179.35 (11)
O2—N1—C9—C10	−164.27 (12)	C11—C10—C9—C8	−0.84 (19)
O2—N1—C9—C8	15.92 (19)	C11—C6—C5—C4	−7.6 (2)
O3—N1—C9—C10	15.98 (19)	C11—C6—C7—C8	0.74 (19)
O3—N1—C9—C8	−163.83 (13)	C9—C10—C11—C6	0.93 (18)
N1—C9—C8—C7	−179.49 (12)	C9—C8—C7—C6	−0.6 (2)
C1—C2—C3—C1^i	−0.34 (18)	C5—C6—C11—C10	177.54 (11)
C1—C2—C3—C4	−178.81 (11)	C5—C6—C7—C8	−177.76 (12)
C1^i—C3—C4—C5	172.08 (12)	C7—C6—C11—C10	−0.89 (18)
C2—C3—C4—C5	−9.4 (2)	C7—C6—C5—C4	170.84 (13)
C3^i—C1—C2—C3	0.34 (19)	C12—O1—C1—C2	4.15 (17)
C3—C4—C5—C6	−179.01 (12)	C12—O1—C1—C3^i	−176.23 (11)
C10—C9—C8—C7	0.7 (2)

Symmetry code: (i) −x+2, −y+1, −z+1.