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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013092/lh2038sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013092/lh2038Isup2.hkl
Contains datablock I

CCDC reference: 608448

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

Computing details top

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 top
Crystal data top
C26H16Cl4N2F(000) = 508
Mr = 498.21Dx = 1.449 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5455 reflections
a = 4.7801 (3) Åθ = 2.5–25.6°
b = 10.9874 (6) ŵ = 0.54 mm1
c = 21.778 (1) ÅT = 291 K
β = 93.230 (1)°Block, colourless
V = 1142.0 (1) Å30.36 × 0.25 × 0.13 mm
Z = 2
Data collection top
Bruker APEX area-detector
diffractometer
1932 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 27.5°, θmin = 2.6°
φ and ω scansh = 66
9739 measured reflectionsk = 1414
2623 independent reflectionsl = 2827
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0751P)2 + 0.4894P]
where P = (Fo2 + 2Fc2)/3
2623 reflections(Δ/σ)max = 0.001
229 parametersΔρmax = 0.32 e Å3
98 restraintsΔρmin = 0.30 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.4695 (4)0.0005 (2)0.7354 (1)0.0659 (4)0.50
Cl21.1491 (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
N10.7846 (5)0.1451 (2)0.6305 (1)0.0619 (6)
C10.6868 (5)0.2460 (2)0.5945 (1)0.0501 (5)
C20.440 (1)0.2456 (5)0.5603 (2)0.051 (1)0.50
C30.367 (1)0.3451 (4)0.5244 (2)0.052 (1)0.50
C40.5376 (4)0.4471 (2)0.5204 (1)0.0468 (5)
C50.788 (1)0.4437 (5)0.5580 (2)0.056 (1)0.50
C60.869 (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
C70.748 (1)0.0407 (3)0.6118 (2)0.047 (1)0.50
C80.8021 (8)0.0674 (3)0.6533 (2)0.077 (1)0.50
C90.715 (2)0.0996 (5)0.7109 (2)0.058 (2)0.50
C100.815 (2)0.2057 (6)0.7392 (3)0.055 (2)0.50
C111.002 (2)0.2796 (5)0.7098 (3)0.060 (2)0.50
C121.089 (2)0.2474 (6)0.6522 (3)0.074 (2)0.50
C130.989 (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
H20.32080.17860.56120.061*0.50
H30.19580.34410.50190.063*0.50
H50.90550.51130.55840.067*0.50
H61.03760.34380.61770.065*0.50
H2'0.48630.15350.52500.075*0.50
H3'0.36070.31830.46330.071*0.50
H5'0.73100.54180.58790.065*0.50
H6'0.85060.37870.64890.065*0.50
H70.68640.02800.57110.056*0.50
H100.75610.22730.77770.066*0.50
H111.06860.35060.72870.072*0.50
H121.21450.29680.63260.088*0.50
H7'0.45380.06080.63070.070*0.50
H10'0.69200.20790.78980.068*0.50
H11'1.00050.34120.74610.063*0.50
H12'1.16600.29920.65030.076*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.071 (1)0.061 (1)0.067 (1)0.008 (1)0.017 (1)0.001 (1)
Cl20.082 (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)
N10.083 (1)0.041 (1)0.060 (1)0.003 (1)0.014 (1)0.010 (1)
C10.066 (1)0.039 (1)0.046 (1)0.002 (1)0.002 (1)0.008 (1)
C40.054 (1)0.036 (1)0.050 (1)0.004 (1)0.006 (1)0.006 (1)
C20.049 (3)0.035 (2)0.070 (4)0.002 (2)0.006 (2)0.014 (2)
C30.046 (3)0.044 (3)0.066 (4)0.003 (2)0.003 (2)0.011 (2)
C50.076 (4)0.041 (3)0.050 (3)0.009 (3)0.001 (3)0.007 (2)
C60.063 (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)
C70.051 (3)0.051 (2)0.039 (2)0.003 (2)0.006 (2)0.012 (2)
C80.082 (2)0.049 (1)0.095 (2)0.025 (1)0.047 (2)0.029 (2)
C90.050 (3)0.034 (3)0.087 (4)0.000 (2)0.019 (3)0.006 (3)
C100.062 (5)0.050 (3)0.054 (3)0.004 (3)0.004 (3)0.007 (3)
C110.066 (4)0.047 (3)0.067 (5)0.002 (2)0.009 (3)0.015 (3)
C120.084 (5)0.065 (4)0.072 (5)0.013 (3)0.012 (4)0.001 (4)
C130.096 (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) top
Cl1—C91.708 (3)C11—C121.39
Cl2—C131.716 (3)C12—C131.39
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—C71.226 (4)C9'—C10'1.39
N1—C11.422 (3)C10'—C11'1.39
C1—C21.361 (6)C11'—C12'1.39
C1—C6'1.391 (5)C12'—C13'1.39
C1—C61.386 (6)C2—H20.93
C1—C2'1.399 (6)C3—H30.93
C4—C5'1.351 (6)C5—H50.93
C4—C31.392 (5)C6—H60.93
C4—C3'1.398 (6)C2'—H2'0.93
C4—C51.414 (6)C3'—H3'0.93
C4—C4i1.493 (4)C5'—H5'0.93
C2—C31.377 (6)C6'—H6'0.93
C5—C61.391 (6)C7—H70.93
C2'—C3'1.389 (6)C10—H100.93
C5'—C6'1.374 (6)C11—H110.93
C7—C81.506 (3)C12—H120.93
C8—C91.39C7'—H7'0.93
C8—C131.39C10'—H10'0.93
C9—C101.39C11'—H11'0.93
C10—C111.39C12'—H12'0.93
C7'—N1—C1123.5 (2)C8'—C9'—C10'120.0
C7—N1—C1120.7 (3)C8'—C9'—Cl1'131.2 (3)
C2—C1—C6'109.0 (3)C10'—C9'—Cl1'108.7 (3)
C2—C1—C6121.8 (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—N1123.2 (3)C12'—C13'—Cl2'130.0 (4)
C6'—C1—N1121.7 (3)C8'—C13'—Cl2'109.9 (4)
C6—C1—N1115.0 (3)C1—C2—H2120.3
C2'—C1—N1122.1 (3)C3—C2—H2120.3
C5'—C4—C3108.8 (3)C2—C3—H3118.5
C5'—C4—C3'120.3 (4)C4—C3—H3118.5
C3—C4—C5115.0 (4)C6—C5—H5118.4
C3'—C4—C5110.6 (3)C4—C5—H5118.4
C5'—C4—C4i120.7 (3)C1—C6—H6121.3
C3—C4—C4i122.8 (3)C5—C6—H6121.3
C3'—C4—C4i119.0 (3)C3'—C2'—H2'119.0
C5—C4—C4i122.2 (3)C1—C2'—H2'119.0
C1—C2—C3119.4 (5)C2'—C3'—H3'120.5
C2—C3—C4123.0 (5)C4—C3'—H3'120.5
C6—C5—C4123.3 (5)C4—C5'—H5'120.0
C1—C6—C5117.4 (5)C6'—C5'—H5'120.0
C3'—C2'—C1121.9 (5)C5'—C6'—H6'118.6
C2'—C3'—C4118.9 (5)C1—C6'—H6'118.6
C4—C5'—C6'120.0 (5)N1—C7—H7119.2
C5'—C6'—C1122.9 (5)C8—C7—H7119.2
N1—C7—C8121.5 (3)C11—C10—H10120.0
C9—C8—C13120.0C9—C10—H10120.0
C9—C8—C7133.8 (2)C10—C11—H11120.0
C13—C8—C7106.1 (2)C12—C11—H11120.0
C8—C9—C10120.0C13—C12—C11120.0
C8—C9—Cl1111.5 (2)C13—C12—H12120.0
C10—C9—Cl1128.4 (2)C11—C12—H12120.0
C11—C10—C9120.0N1—C7'—H7'118.7
C10—C11—C12120.0C8'—C7'—H7'118.7
C12—C13—C8120.0C9'—C10'—H10'120.0
C12—C13—Cl2105.4 (2)C11'—C10'—H10'120.0
C8—C13—Cl2134.6 (2)C12'—C11'—C10'120.0
N1—C7'—C8'122.6 (4)C12'—C11'—H11'120.0
C9'—C8'—C13'120.0C10'—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—C28.2 (5)C2'—C1—C6'—C5'0.9 (5)
C7—N1—C1—C238.0 (4)N1—C1—C6'—C5'174.5 (4)
C7'—N1—C1—C6'141.3 (5)C7'—N1—C7—C862.0 (3)
C7—N1—C1—C6'172.5 (4)C1—N1—C7—C8168.7 (3)
C7'—N1—C1—C6174.7 (4)N1—C7—C8—C951.9 (9)
C7—N1—C1—C6139.1 (4)N1—C7—C8—C13125.1 (5)
C7'—N1—C1—C2'43.6 (5)C7—C8—C9—C10176.7 (5)
C7—N1—C1—C2'2.6 (4)C13—C8—C9—Cl1176.2 (6)
C6—C1—C2—C30.1 (2)C7—C8—C9—Cl17 (1)
N1—C1—C2—C3176.9 (2)Cl1—C9—C10—C11175.5 (8)
C1—C2—C3—C41.1 (2)C11—C12—C13—Cl2179.2 (8)
C5—C4—C3—C22.5 (4)C7—C8—C13—C12177.5 (3)
C4i—C4—C3—C2177.7 (3)C9—C8—C13—Cl2179 (1)
C3—C4—C5—C63.0 (6)C7—C8—C13—Cl21.4 (9)
C4i—C4—C5—C6177.3 (4)C7—N1—C7'—C8'64.8 (5)
C2—C1—C6—C50.4 (5)C1—N1—C7'—C8'163.8 (5)
N1—C1—C6—C5177.5 (3)N1—C7'—C8'—C9'115.6 (7)
C4—C5—C6—C12.0 (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'—C40.2 (2)Cl1'—C9'—C10'—C11'177.6 (7)
C4i—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)
C4i—C4—C5'—C6'178.8 (4)C9'—C8'—C13'—Cl2'177.1 (7)
C4—C5'—C6'—C10.5 (7)C7'—C8'—C13'—Cl2'2.6 (8)
Symmetry code: (i) x+1, y+1, z+1.
 

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