4,4'-Bis(4-nitro­phen­oxy)biphen­yl

The asymmetric unit of the title compound, C₂₄H₁₆N₂O₆, contains one half-mol­ecule; there is a crystallographic inversion centreat the mid-point of the central C-C bond, constraining the central biphenyl group to be planar.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.024
• wR factor = 0.073
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O3     -   N1      ..       8.37 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C11    -   C16     ..       7.24 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C21    -   C22     ..       8.55 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C22    -   C23     ..       8.29 su

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   C21     ..       5.17 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C24     ..       6.07 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12    -   C13     ..       5.09 su

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
   3 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
   7 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

4,4'-Bis(4-nitrophenoxy)biphenyl

Crystal data

C24H16N2O6	F(000) = 444
Mr = 428.39	Dx = 1.428 Mg m^−3
Monoclinic, P21/c	Melting point: 418 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.6245 (17) Å	Cell parameters from 2164 reflections
b = 9.0387 (14) Å	θ = 3.8–25.4°
c = 10.4509 (16) Å	µ = 0.10 mm^−1
β = 97.042 (13)°	T = 173 K
V = 996.0 (3) Å^3	Block, light brown
Z = 2	0.35 × 0.32 × 0.29 mm

Data collection

Stoe IPDS-II two-circle diffractometer	1556 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
ω scans	h = −12→12
3482 measured reflections	k = 0→10
1766 independent reflections	l = 0→12

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0553P)^2] where P = (Fo^2 + 2Fc^2)/3
1766 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.13 e Å^−3
0 restraints	Δρmin = −0.13 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.74680 (6)	0.27835 (4)	0.67480 (5)	0.03616 (19)
N1	0.88059 (7)	0.57912 (5)	0.24384 (6)	0.03155 (19)
O2	0.82727 (6)	0.69709 (4)	0.21113 (5)	0.0437 (2)
O3	0.96227 (7)	0.52261 (5)	0.18511 (6)	0.04579 (19)
C11	0.67598 (9)	0.34822 (6)	0.76328 (7)	0.0302 (2)
C12	0.56139 (9)	0.28363 (6)	0.78233 (7)	0.0361 (2)
H12	0.5299	0.2001	0.7333	0.043*
C13	0.49339 (9)	0.34526 (6)	0.87603 (7)	0.0348 (2)
H13	0.4143	0.3025	0.8892	0.042*
C14	0.53699 (7)	0.46618 (5)	0.95022 (6)	0.0240 (2)
C15	0.65561 (9)	0.52604 (6)	0.92945 (7)	0.0305 (2)
H15	0.6893	0.6075	0.9800	0.037*
C16	0.72385 (9)	0.46709 (6)	0.83579 (8)	0.0339 (2)
H16	0.8031	0.5088	0.8221	0.041*
C21	0.77757 (8)	0.36068 (6)	0.57130 (6)	0.0289 (2)
C22	0.70996 (9)	0.48531 (5)	0.52442 (7)	0.0320 (2)
H22	0.6412	0.5208	0.5659	0.038*
C23	0.74410 (9)	0.55714 (6)	0.41632 (7)	0.0319 (2)
H23	0.6994	0.6425	0.3828	0.038*
C24	0.84550 (8)	0.50122 (6)	0.35796 (6)	0.0262 (2)
C25	0.91284 (8)	0.37689 (5)	0.40397 (6)	0.0282 (2)
H25	0.9813	0.3413	0.3621	0.034*
C26	0.87901 (8)	0.30550 (5)	0.51147 (6)	0.0290 (2)
H26	0.9239	0.2201	0.5445	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0499 (5)	0.0307 (2)	0.0312 (3)	0.0137 (2)	0.0184 (3)	0.00445 (17)
N1	0.0311 (4)	0.0326 (3)	0.0316 (3)	−0.0063 (3)	0.0065 (3)	−0.0004 (2)
O2	0.0469 (5)	0.0394 (2)	0.0466 (3)	−0.0005 (2)	0.0126 (3)	0.0107 (2)
O3	0.0455 (5)	0.0518 (3)	0.0453 (3)	−0.0029 (3)	0.0261 (3)	−0.0021 (2)
C11	0.0355 (5)	0.0319 (3)	0.0248 (3)	0.0096 (3)	0.0098 (3)	0.0032 (2)
C12	0.0371 (6)	0.0377 (3)	0.0338 (4)	−0.0045 (4)	0.0052 (4)	−0.0110 (3)
C13	0.0307 (5)	0.0398 (3)	0.0350 (4)	−0.0058 (3)	0.0086 (3)	−0.0097 (3)
C14	0.0270 (5)	0.0229 (3)	0.0220 (3)	0.0027 (3)	0.0029 (3)	0.0047 (2)
C15	0.0311 (5)	0.0277 (3)	0.0340 (4)	−0.0044 (3)	0.0088 (3)	−0.0024 (2)
C16	0.0318 (5)	0.0337 (3)	0.0384 (4)	−0.0021 (3)	0.0138 (3)	−0.0013 (3)
C21	0.0325 (5)	0.0308 (2)	0.0242 (3)	0.0020 (3)	0.0062 (3)	−0.0032 (2)
C22	0.0338 (5)	0.0339 (3)	0.0299 (4)	0.0104 (3)	0.0108 (3)	0.0008 (2)
C23	0.0352 (5)	0.0291 (2)	0.0322 (4)	0.0069 (3)	0.0067 (3)	−0.0017 (2)
C24	0.0271 (5)	0.0287 (3)	0.0229 (3)	−0.0046 (3)	0.0037 (3)	−0.0033 (2)
C25	0.0249 (5)	0.0305 (3)	0.0301 (4)	0.0002 (3)	0.0064 (3)	−0.0074 (2)
C26	0.0288 (5)	0.0252 (3)	0.0332 (4)	0.0050 (3)	0.0043 (3)	−0.0053 (2)

Geometric parameters (Å, º)

O1—C21	1.3847 (9)	C15—C16	1.3934 (12)
O1—C11	1.4109 (10)	C15—H15	0.9500
N1—O3	1.2334 (10)	C16—H16	0.9500
N1—O2	1.2357 (8)	C21—C22	1.3923 (9)
N1—C24	1.4718 (10)	C21—C26	1.4024 (13)
C11—C16	1.3758 (10)	C22—C23	1.3893 (11)
C11—C12	1.3864 (13)	C22—H22	0.9500
C12—C13	1.4017 (13)	C23—C24	1.3961 (12)
C12—H12	0.9500	C23—H23	0.9500
C13—C14	1.3865 (8)	C24—C25	1.3862 (9)
C13—H13	0.9500	C25—C26	1.3808 (11)
C14—C15	1.4125 (12)	C25—H25	0.9500
C14—C14^i	1.5081 (15)	C26—H26	0.9500
C21—O1—C11	117.86 (4)	C11—C16—H16	120.1
O3—N1—O2	123.11 (7)	C15—C16—H16	120.1
O3—N1—C24	117.95 (5)	O1—C21—C22	123.28 (8)
O2—N1—C24	118.94 (7)	O1—C21—C26	115.16 (6)
C16—C11—C12	121.44 (8)	C22—C21—C26	121.49 (7)
C16—C11—O1	121.32 (8)	C23—C22—C21	119.30 (8)
C12—C11—O1	116.99 (6)	C23—C22—H22	120.4
C11—C12—C13	118.03 (5)	C21—C22—H22	120.4
C11—C12—H12	121.0	C22—C23—C24	118.59 (6)
C13—C12—H12	121.0	C22—C23—H23	120.7
C14—C13—C12	122.58 (8)	C24—C23—H23	120.7
C14—C13—H13	118.7	C25—C24—C23	122.35 (7)
C12—C13—H13	118.7	C25—C24—N1	119.85 (7)
C13—C14—C15	117.34 (8)	C23—C24—N1	117.81 (6)
C13—C14—C14^i	122.60 (9)	C26—C25—C24	119.10 (7)
C15—C14—C14^i	120.07 (6)	C26—C25—H25	120.5
C16—C15—C14	120.82 (6)	C24—C25—H25	120.5
C16—C15—H15	119.6	C25—C26—C21	119.17 (6)
C14—C15—H15	119.6	C25—C26—H26	120.4
C11—C16—C15	119.77 (8)	C21—C26—H26	120.4
C21—O1—C11—C16	−63.32 (8)	O1—C21—C22—C23	−177.03 (6)
C21—O1—C11—C12	122.38 (7)	C26—C21—C22—C23	−0.32 (10)
C16—C11—C12—C13	1.53 (10)	C21—C22—C23—C24	0.14 (10)
O1—C11—C12—C13	175.82 (5)	C22—C23—C24—C25	0.09 (10)
C11—C12—C13—C14	−0.66 (10)	C22—C23—C24—N1	−179.77 (5)
C12—C13—C14—C15	−0.79 (10)	O3—N1—C24—C25	6.63 (9)
C12—C13—C14—C14^i	179.14 (6)	O2—N1—C24—C25	−173.51 (5)
C13—C14—C15—C16	1.43 (9)	O3—N1—C24—C23	−173.51 (6)
C14^i—C14—C15—C16	−178.49 (6)	O2—N1—C24—C23	6.36 (9)
C12—C11—C16—C15	−0.91 (10)	C23—C24—C25—C26	−0.13 (9)
O1—C11—C16—C15	−174.95 (5)	N1—C24—C25—C26	179.72 (5)
C14—C15—C16—C11	−0.62 (9)	C24—C25—C26—C21	−0.05 (8)
C11—O1—C21—C22	−22.77 (9)	O1—C21—C26—C25	177.24 (5)
C11—O1—C21—C26	160.33 (6)	C22—C21—C26—C25	0.28 (9)

Symmetry code: (i) −x+1, −y+1, −z+2.