4,4'-Bis(2,6-dichloro­benzyl­ideneamino)biphen­yl

The title mol­ecule, C₂₆H₁₆Cl₄N₂, lies on a crystallographic inversion centre and is disordered. The dihedral angle between the two benzene rings of the central biphenyl unit is 34.4 (3)°. The unique benzene ring of the biphenyl group is essentially coplanar with the -C(H)=N- unit, whereas the 2,6-dichloro­phenyl substituent is twisted with respect to it. The reason for the twisted conformation is attributed to steric crowding by the Cl atoms.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.052
• wR factor = 0.167
• Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT301_ALERT_3_B Main Residue  Disorder .........................      45.00 Perc.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C2     ..  C6      ..       3.07 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C3     ..  C6      ..       2.90 Ang.

Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT432_ALERT_2_C Short Inter X...Y Contact  C3     ..  C5      ..       3.10 Ang.

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   2 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
   4 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.

4,4'-Bis(2,6-dichlorobenzylideneamino)biphenyl

Crystal data

C26H16Cl4N2	F(000) = 508
Mr = 498.21	Dx = 1.449 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5455 reflections
a = 4.7801 (3) Å	θ = 2.5–25.6°
b = 10.9874 (6) Å	µ = 0.54 mm^−1
c = 21.778 (1) Å	T = 291 K
β = 93.230 (1)°	Block, colourless
V = 1142.0 (1) Å^3	0.36 × 0.25 × 0.13 mm
Z = 2

Data collection

Bruker APEX area-detector diffractometer	1932 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 27.5°, θmin = 2.6°
φ and ω scans	h = −6→6
9739 measured reflections	k = −14→14
2623 independent reflections	l = −28→27

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.167	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0751P)^2 + 0.4894P] where P = (Fo^2 + 2Fc^2)/3
2623 reflections	(Δ/σ)max = 0.001
229 parameters	Δρmax = 0.32 e Å^−3
98 restraints	Δρmin = −0.30 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.4695 (4)	−0.0005 (2)	0.7354 (1)	0.0659 (4)	0.50
Cl2	1.1491 (4)	−0.1341 (2)	0.5554 (1)	0.0744 (5)	0.50
Cl1'	0.4553 (5)	−0.0033 (2)	0.7660 (1)	0.0816 (6)	0.50
Cl2'	1.0306 (5)	−0.0907 (2)	0.5639 (1)	0.0879 (6)	0.50
N1	0.7846 (5)	0.1451 (2)	0.6305 (1)	0.0619 (6)
C1	0.6868 (5)	0.2460 (2)	0.5945 (1)	0.0501 (5)
C2	0.440 (1)	0.2456 (5)	0.5603 (2)	0.051 (1)	0.50
C3	0.367 (1)	0.3451 (4)	0.5244 (2)	0.052 (1)	0.50
C4	0.5376 (4)	0.4471 (2)	0.5204 (1)	0.0468 (5)
C5	0.788 (1)	0.4437 (5)	0.5580 (2)	0.056 (1)	0.50
C6	0.869 (1)	0.3443 (5)	0.5944 (2)	0.054 (1)	0.50
C2'	0.537 (1)	0.2314 (5)	0.5380 (2)	0.062 (2)	0.50
C3'	0.461 (1)	0.3300 (5)	0.5007 (3)	0.059 (1)	0.50
C5'	0.681 (1)	0.4637 (5)	0.5750 (2)	0.054 (1)	0.50
C6'	0.753 (1)	0.3652 (4)	0.6114 (3)	0.054 (1)	0.50
C7	0.748 (1)	0.0407 (3)	0.6118 (2)	0.047 (1)	0.50
C8	0.8021 (8)	−0.0674 (3)	0.6533 (2)	0.077 (1)	0.50
C9	0.715 (2)	−0.0996 (5)	0.7109 (2)	0.058 (2)	0.50
C10	0.815 (2)	−0.2057 (6)	0.7392 (3)	0.055 (2)	0.50
C11	1.002 (2)	−0.2796 (5)	0.7098 (3)	0.060 (2)	0.50
C12	1.089 (2)	−0.2474 (6)	0.6522 (3)	0.074 (2)	0.50
C13	0.989 (2)	−0.1413 (6)	0.6240 (3)	0.077 (2)	0.50
C7'	0.6465 (8)	0.0567 (3)	0.6390 (3)	0.059 (1)	0.50
C8'	0.772 (1)	−0.0609 (4)	0.6627 (2)	0.077 (1)	0.50
C9'	0.673 (2)	−0.0860 (5)	0.7201 (3)	0.076 (2)	0.50
C10'	0.758 (2)	−0.1910 (7)	0.7514 (3)	0.057 (2)	0.50
C11'	0.943 (2)	−0.2709 (5)	0.7252 (3)	0.053 (2)	0.50
C12'	1.042 (2)	−0.2458 (6)	0.6678 (3)	0.064 (2)	0.50
C13'	0.957 (2)	−0.1407 (7)	0.6365 (2)	0.079 (3)	0.50
H2	0.3208	0.1786	0.5612	0.061*	0.50
H3	0.1958	0.3441	0.5019	0.063*	0.50
H5	0.9055	0.5113	0.5584	0.067*	0.50
H6	1.0376	0.3438	0.6177	0.065*	0.50
H2'	0.4863	0.1535	0.5250	0.075*	0.50
H3'	0.3607	0.3183	0.4633	0.071*	0.50
H5'	0.7310	0.5418	0.5879	0.065*	0.50
H6'	0.8506	0.3787	0.6489	0.065*	0.50
H7	0.6864	0.0280	0.5711	0.056*	0.50
H10	0.7561	−0.2273	0.7777	0.066*	0.50
H11	1.0686	−0.3506	0.7287	0.072*	0.50
H12	1.2145	−0.2968	0.6326	0.088*	0.50
H7'	0.4538	0.0608	0.6307	0.070*	0.50
H10'	0.6920	−0.2079	0.7898	0.068*	0.50
H11'	1.0005	−0.3412	0.7461	0.063*	0.50
H12'	1.1660	−0.2992	0.6503	0.076*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.071 (1)	0.061 (1)	0.067 (1)	−0.008 (1)	0.017 (1)	0.001 (1)
Cl2	0.082 (1)	0.074 (1)	0.069 (1)	0.004 (1)	0.019 (1)	−0.013 (1)
Cl1'	0.086 (1)	0.077 (1)	0.084 (1)	−0.011 (1)	0.022 (1)	0.000 (1)
Cl2'	0.119 (2)	0.077 (1)	0.070 (1)	−0.009 (1)	0.024 (1)	−0.006 (1)
N1	0.083 (1)	0.041 (1)	0.060 (1)	−0.003 (1)	−0.014 (1)	0.010 (1)
C1	0.066 (1)	0.039 (1)	0.046 (1)	0.002 (1)	0.002 (1)	0.008 (1)
C4	0.054 (1)	0.036 (1)	0.050 (1)	0.004 (1)	0.006 (1)	0.006 (1)
C2	0.049 (3)	0.035 (2)	0.070 (4)	−0.002 (2)	0.006 (2)	0.014 (2)
C3	0.046 (3)	0.044 (3)	0.066 (4)	0.003 (2)	0.003 (2)	0.011 (2)
C5	0.076 (4)	0.041 (3)	0.050 (3)	−0.009 (3)	−0.001 (3)	0.007 (2)
C6	0.063 (4)	0.046 (3)	0.052 (3)	−0.002 (2)	−0.006 (2)	0.008 (2)
C2'	0.085 (5)	0.036 (2)	0.065 (4)	0.001 (3)	−0.005 (3)	0.003 (2)
C3'	0.081 (4)	0.044 (3)	0.051 (3)	0.000 (3)	−0.009 (3)	0.007 (2)
C5'	0.079 (4)	0.031 (2)	0.051 (3)	−0.001 (3)	−0.005 (3)	0.000 (2)
C6'	0.074 (4)	0.040 (2)	0.047 (3)	0.002 (3)	−0.011 (3)	0.003 (2)
C7	0.051 (3)	0.051 (2)	0.039 (2)	−0.003 (2)	0.006 (2)	0.012 (2)
C8	0.082 (2)	0.049 (1)	0.095 (2)	−0.025 (1)	−0.047 (2)	0.029 (2)
C9	0.050 (3)	0.034 (3)	0.087 (4)	0.000 (2)	−0.019 (3)	−0.006 (3)
C10	0.062 (5)	0.050 (3)	0.054 (3)	−0.004 (3)	0.004 (3)	0.007 (3)
C11	0.066 (4)	0.047 (3)	0.067 (5)	0.002 (2)	0.009 (3)	0.015 (3)
C12	0.084 (5)	0.065 (4)	0.072 (5)	−0.013 (3)	0.012 (4)	−0.001 (4)
C13	0.096 (5)	0.058 (4)	0.075 (4)	−0.023 (4)	−0.018 (4)	0.006 (3)
C7'	0.053 (3)	0.057 (3)	0.064 (3)	−0.016 (2)	−0.011 (2)	0.022 (2)
C8'	0.082 (2)	0.049 (1)	0.095 (2)	−0.025 (1)	−0.047 (2)	0.029 (2)
C9'	0.064 (4)	0.047 (4)	0.114 (6)	−0.018 (3)	−0.032 (4)	0.025 (4)
C10'	0.056 (4)	0.052 (3)	0.061 (3)	0.000 (2)	−0.001 (3)	0.007 (3)
C11'	0.063 (4)	0.046 (3)	0.050 (3)	0.006 (2)	0.009 (3)	0.012 (2)
C12'	0.083 (4)	0.054 (3)	0.055 (4)	−0.017 (3)	0.014 (3)	0.001 (3)
C13'	0.103 (5)	0.087 (6)	0.043 (3)	−0.057 (4)	−0.027 (3)	0.037 (3)

Geometric parameters (Å, º)

Cl1—C9	1.708 (3)	C11—C12	1.39
Cl2—C13	1.716 (3)	C12—C13	1.39
Cl1'—C9'	1.738 (3)	C7'—C8'	1.502 (4)
Cl2'—C13'	1.729 (3)	C8'—C9'	1.39
N1—C7'	1.195 (4)	C8'—C13'	1.39
N1—C7	1.226 (4)	C9'—C10'	1.39
N1—C1	1.422 (3)	C10'—C11'	1.39
C1—C2	1.361 (6)	C11'—C12'	1.39
C1—C6'	1.391 (5)	C12'—C13'	1.39
C1—C6	1.386 (6)	C2—H2	0.93
C1—C2'	1.399 (6)	C3—H3	0.93
C4—C5'	1.351 (6)	C5—H5	0.93
C4—C3	1.392 (5)	C6—H6	0.93
C4—C3'	1.398 (6)	C2'—H2'	0.93
C4—C5	1.414 (6)	C3'—H3'	0.93
C4—C4^i	1.493 (4)	C5'—H5'	0.93
C2—C3	1.377 (6)	C6'—H6'	0.93
C5—C6	1.391 (6)	C7—H7	0.93
C2'—C3'	1.389 (6)	C10—H10	0.93
C5'—C6'	1.374 (6)	C11—H11	0.93
C7—C8	1.506 (3)	C12—H12	0.93
C8—C9	1.39	C7'—H7'	0.93
C8—C13	1.39	C10'—H10'	0.93
C9—C10	1.39	C11'—H11'	0.93
C10—C11	1.39	C12'—H12'	0.93
C7'—N1—C1	123.5 (2)	C8'—C9'—C10'	120.0
C7—N1—C1	120.7 (3)	C8'—C9'—Cl1'	131.2 (3)
C2—C1—C6'	109.0 (3)	C10'—C9'—Cl1'	108.7 (3)
C2—C1—C6	121.8 (4)	C9'—C10'—C11'	120.0
C6'—C1—C2'	116.0 (4)	C11'—C12'—C13'	120.0
C6—C1—C2'	112.2 (3)	C12'—C13'—C8'	120.0
C2—C1—N1	123.2 (3)	C12'—C13'—Cl2'	130.0 (4)
C6'—C1—N1	121.7 (3)	C8'—C13'—Cl2'	109.9 (4)
C6—C1—N1	115.0 (3)	C1—C2—H2	120.3
C2'—C1—N1	122.1 (3)	C3—C2—H2	120.3
C5'—C4—C3	108.8 (3)	C2—C3—H3	118.5
C5'—C4—C3'	120.3 (4)	C4—C3—H3	118.5
C3—C4—C5	115.0 (4)	C6—C5—H5	118.4
C3'—C4—C5	110.6 (3)	C4—C5—H5	118.4
C5'—C4—C4^i	120.7 (3)	C1—C6—H6	121.3
C3—C4—C4^i	122.8 (3)	C5—C6—H6	121.3
C3'—C4—C4^i	119.0 (3)	C3'—C2'—H2'	119.0
C5—C4—C4^i	122.2 (3)	C1—C2'—H2'	119.0
C1—C2—C3	119.4 (5)	C2'—C3'—H3'	120.5
C2—C3—C4	123.0 (5)	C4—C3'—H3'	120.5
C6—C5—C4	123.3 (5)	C4—C5'—H5'	120.0
C1—C6—C5	117.4 (5)	C6'—C5'—H5'	120.0
C3'—C2'—C1	121.9 (5)	C5'—C6'—H6'	118.6
C2'—C3'—C4	118.9 (5)	C1—C6'—H6'	118.6
C4—C5'—C6'	120.0 (5)	N1—C7—H7	119.2
C5'—C6'—C1	122.9 (5)	C8—C7—H7	119.2
N1—C7—C8	121.5 (3)	C11—C10—H10	120.0
C9—C8—C13	120.0	C9—C10—H10	120.0
C9—C8—C7	133.8 (2)	C10—C11—H11	120.0
C13—C8—C7	106.1 (2)	C12—C11—H11	120.0
C8—C9—C10	120.0	C13—C12—C11	120.0
C8—C9—Cl1	111.5 (2)	C13—C12—H12	120.0
C10—C9—Cl1	128.4 (2)	C11—C12—H12	120.0
C11—C10—C9	120.0	N1—C7'—H7'	118.7
C10—C11—C12	120.0	C8'—C7'—H7'	118.7
C12—C13—C8	120.0	C9'—C10'—H10'	120.0
C12—C13—Cl2	105.4 (2)	C11'—C10'—H10'	120.0
C8—C13—Cl2	134.6 (2)	C12'—C11'—C10'	120.0
N1—C7'—C8'	122.6 (4)	C12'—C11'—H11'	120.0
C9'—C8'—C13'	120.0	C10'—C11'—H11'	120.0
C9'—C8'—C7'	109.2 (5)	C11'—C12'—H12'	120.0
C13'—C8'—C7'	130.8 (5)	C13'—C12'—H12'	120.0
C7'—N1—C1—C2	−8.2 (5)	C2'—C1—C6'—C5'	−0.9 (5)
C7—N1—C1—C2	38.0 (4)	N1—C1—C6'—C5'	174.5 (4)
C7'—N1—C1—C6'	141.3 (5)	C7'—N1—C7—C8	−62.0 (3)
C7—N1—C1—C6'	−172.5 (4)	C1—N1—C7—C8	−168.7 (3)
C7'—N1—C1—C6	174.7 (4)	N1—C7—C8—C9	51.9 (9)
C7—N1—C1—C6	−139.1 (4)	N1—C7—C8—C13	−125.1 (5)
C7'—N1—C1—C2'	−43.6 (5)	C7—C8—C9—C10	−176.7 (5)
C7—N1—C1—C2'	2.6 (4)	C13—C8—C9—Cl1	−176.2 (6)
C6—C1—C2—C3	0.1 (2)	C7—C8—C9—Cl1	7 (1)
N1—C1—C2—C3	−176.9 (2)	Cl1—C9—C10—C11	175.5 (8)
C1—C2—C3—C4	1.1 (2)	C11—C12—C13—Cl2	179.2 (8)
C5—C4—C3—C2	−2.5 (4)	C7—C8—C13—C12	177.5 (3)
C4^i—C4—C3—C2	177.7 (3)	C9—C8—C13—Cl2	−179 (1)
C3—C4—C5—C6	3.0 (6)	C7—C8—C13—Cl2	−1.4 (9)
C4^i—C4—C5—C6	−177.3 (4)	C7—N1—C7'—C8'	64.8 (5)
C2—C1—C6—C5	0.4 (5)	C1—N1—C7'—C8'	163.8 (5)
N1—C1—C6—C5	177.5 (3)	N1—C7'—C8'—C9'	115.6 (7)
C4—C5—C6—C1	−2.0 (6)	N1—C7'—C8'—C13'	−64.8 (9)
C6'—C1—C2'—C3'	0.5 (2)	C7'—C8'—C9'—C10'	179.7 (4)
C6—C1—C2'—C3'	−32.2 (3)	C13'—C8'—C9'—Cl1'	177.0 (9)
N1—C1—C2'—C3'	−174.8 (2)	C7'—C8'—C9'—Cl1'	−3.3 (9)
C1—C2'—C3'—C4	0.2 (2)	Cl1'—C9'—C10'—C11'	−177.6 (7)
C4^i—C4—C3'—C2'	178.5 (2)	C11'—C12'—C13'—Cl2'	−176.4 (9)
C3'—C4—C5'—C6'	0.3 (6)	C7'—C8'—C13'—C12'	−179.6 (5)
C4^i—C4—C5'—C6'	−178.8 (4)	C9'—C8'—C13'—Cl2'	177.1 (7)
C4—C5'—C6'—C1	0.5 (7)	C7'—C8'—C13'—Cl2'	−2.6 (8)

Symmetry code: (i) −x+1, −y+1, −z+1.