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The salicyl­idene­aniline moiety in the centrosymmetric title compound, C28H24N2O2, is a phenol–imine tautomer which is non-planar and photochromic. A strong intramolecular hydrogen-bonding interaction, which is a common feature in related imine–phenol compounds, stabilizes the molecular structure. The π system in the salicyl­idene­aniline moiety interacts with symmetry-related π systems through face-to-face π–π interactions and C—H...π interactions, to stabilize the mol­ecules in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804012073/ci6383sup1.cif
Contains datablocks I, global, publication_text

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804012073/ci6383Isup2.hkl
Contains datablock I

CCDC reference: 242354

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.057
  • wR factor = 0.199
  • Data-to-parameter ratio = 21.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C10 .. 5.38 su
0 ALERT level A = In general: serious problem 0 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 1 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: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990) and ORTEP-3 (Farrugia, 1997).

2,2'-{(Z)-Ethane-1,2-diylbis[(Z)-o-phenylenenitrilomethylidyne]}diphenol top
Crystal data top
C28H24N2O2F(000) = 444
Mr = 420.49Dx = 1.273 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 11.817 (3) Åθ = 8–15°
b = 13.762 (6) ŵ = 0.08 mm1
c = 6.873 (2) ÅT = 293 K
β = 101.15 (3)°Block, yellow
V = 1096.6 (6) Å30.25 × 0.22 × 0.20 mm
Z = 2
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.042
Radiation source: fine-focus sealed tubeθmax = 30.0°, θmin = 1.8°
Graphite monochromatorh = 1616
non–profiled ω/2θ scansk = 019
3425 measured reflectionsl = 09
3179 independent reflections3 standard reflections every 120 min
1504 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.199 w = 1/[σ2(Fo2) + (0.0961P)2 + 0.0403P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.005
3179 reflectionsΔρmax = 0.19 e Å3
147 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.039 (7)
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.95547 (17)0.12126 (14)0.3165 (3)0.0384 (5)
C21.03434 (17)0.05488 (14)0.2642 (3)0.0392 (5)
C31.14800 (19)0.06032 (17)0.3620 (3)0.0477 (5)
H31.20140.01710.32800.057*
C41.1842 (2)0.1278 (2)0.5082 (3)0.0552 (6)
H41.26090.12910.57320.066*
C51.1068 (2)0.19376 (18)0.5584 (3)0.0536 (6)
H51.13130.24020.65580.064*
C60.99255 (19)0.19053 (17)0.4633 (3)0.0473 (5)
H60.94010.23470.49730.057*
C70.99653 (18)0.01933 (15)0.1034 (3)0.0429 (5)
H7A0.91770.03860.10480.051*
H7B1.04490.07660.13090.051*
N80.84017 (14)0.11922 (12)0.2103 (3)0.0425 (4)
C90.75664 (19)0.13183 (16)0.3012 (3)0.0475 (5)
H90.77320.14160.43760.057*
C100.63706 (18)0.13139 (16)0.1995 (3)0.0481 (5)
C110.60639 (19)0.12047 (17)0.0074 (4)0.0523 (6)
C120.4916 (2)0.1182 (2)0.0978 (4)0.0694 (8)
H120.47120.11040.23450.083*
C130.4078 (2)0.1272 (2)0.0120 (5)0.0766 (8)
H130.33070.12510.05090.092*
C140.4352 (2)0.1392 (2)0.2140 (5)0.0805 (9)
H140.37720.14620.28700.097*
C150.5490 (2)0.1408 (2)0.3073 (4)0.0697 (8)
H150.56770.14830.44420.084*
O160.68777 (14)0.11178 (16)0.1208 (2)0.0698 (6)
H160.75130.10490.04900.105*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0443 (11)0.0406 (11)0.0315 (9)0.0013 (9)0.0105 (8)0.0024 (9)
C20.0497 (12)0.0380 (11)0.0322 (10)0.0014 (9)0.0136 (9)0.0031 (9)
C30.0490 (12)0.0553 (14)0.0401 (11)0.0086 (10)0.0118 (9)0.0024 (10)
C40.0483 (13)0.0761 (17)0.0397 (11)0.0018 (12)0.0041 (10)0.0006 (12)
C50.0591 (15)0.0656 (16)0.0365 (11)0.0103 (12)0.0104 (10)0.0101 (11)
C60.0576 (13)0.0467 (13)0.0409 (11)0.0005 (10)0.0181 (10)0.0060 (10)
C70.0527 (12)0.0385 (11)0.0396 (11)0.0021 (9)0.0145 (9)0.0009 (9)
N80.0424 (9)0.0422 (10)0.0444 (10)0.0006 (7)0.0119 (8)0.0025 (8)
C90.0564 (14)0.0455 (13)0.0434 (12)0.0015 (10)0.0167 (10)0.0028 (10)
C100.0432 (11)0.0464 (13)0.0571 (14)0.0002 (9)0.0162 (10)0.0033 (11)
C110.0471 (12)0.0529 (14)0.0575 (14)0.0014 (10)0.0112 (11)0.0021 (11)
C120.0500 (15)0.083 (2)0.0719 (17)0.0012 (13)0.0032 (13)0.0050 (16)
C130.0468 (14)0.084 (2)0.098 (2)0.0002 (14)0.0098 (15)0.0024 (18)
C140.0496 (16)0.098 (2)0.101 (2)0.0068 (14)0.0332 (16)0.0195 (19)
C150.0556 (15)0.089 (2)0.0704 (17)0.0088 (14)0.0279 (13)0.0167 (15)
O160.0537 (10)0.1074 (16)0.0493 (10)0.0072 (11)0.0127 (8)0.0000 (10)
Geometric parameters (Å, º) top
C1—C61.396 (3)N8—C91.278 (3)
C1—C21.401 (3)C9—C101.450 (3)
C1—N81.416 (3)C9—H90.93
C2—C31.383 (3)C10—C151.395 (3)
C2—C71.508 (3)C10—C111.405 (3)
C3—C41.375 (3)C11—O161.355 (3)
C3—H30.93C11—C121.379 (3)
C4—C51.379 (3)C12—C131.361 (4)
C4—H40.93C12—H120.93
C5—C61.382 (3)C13—C141.373 (4)
C5—H50.93C13—H130.93
C6—H60.93C14—C151.374 (3)
C7—C7i1.534 (4)C14—H140.93
C7—H7A0.97C15—H150.93
C7—H7B0.97O16—H160.82
C6—C1—C2119.98 (19)C9—N8—C1120.15 (18)
C6—C1—N8121.50 (18)N8—C9—C10122.4 (2)
C2—C1—N8118.43 (18)N8—C9—H9118.8
C3—C2—C1118.13 (19)C10—C9—H9118.8
C3—C2—C7121.03 (18)C15—C10—C11118.3 (2)
C1—C2—C7120.83 (18)C15—C10—C9120.0 (2)
C4—C3—C2121.9 (2)C11—C10—C9121.6 (2)
C4—C3—H3119.1O16—C11—C12119.0 (2)
C2—C3—H3119.1O16—C11—C10121.2 (2)
C3—C4—C5120.0 (2)C12—C11—C10119.8 (2)
C3—C4—H4120.0C13—C12—C11120.4 (3)
C5—C4—H4120.0C13—C12—H12119.8
C4—C5—C6119.7 (2)C11—C12—H12119.8
C4—C5—H5120.2C12—C13—C14121.1 (3)
C6—C5—H5120.2C12—C13—H13119.4
C5—C6—C1120.3 (2)C14—C13—H13119.4
C5—C6—H6119.8C13—C14—C15119.5 (3)
C1—C6—H6119.8C13—C14—H14120.3
C2—C7—C7i112.5 (2)C15—C14—H14120.3
C2—C7—H7A109.1C14—C15—C10120.9 (3)
C7i—C7—H7A109.1C14—C15—H15119.5
C2—C7—H7B109.1C10—C15—H15119.5
C7i—C7—H7B109.1C11—O16—H16109.5
H7A—C7—H7B107.8
C6—C1—C2—C30.2 (3)C1—N8—C9—C10179.39 (18)
N8—C1—C2—C3176.95 (18)N8—C9—C10—C15176.9 (2)
C6—C1—C2—C7178.86 (18)N8—C9—C10—C112.3 (4)
N8—C1—C2—C72.1 (3)C15—C10—C11—O16179.4 (2)
C1—C2—C3—C40.5 (3)C9—C10—C11—O161.3 (3)
C7—C2—C3—C4179.62 (19)C15—C10—C11—C120.8 (3)
C2—C3—C4—C51.2 (3)C9—C10—C11—C12178.5 (2)
C3—C4—C5—C61.0 (3)O16—C11—C12—C13179.7 (3)
C4—C5—C6—C10.3 (3)C10—C11—C12—C130.5 (4)
C2—C1—C6—C50.4 (3)C11—C12—C13—C140.4 (5)
N8—C1—C6—C5176.99 (19)C12—C13—C14—C150.9 (5)
C3—C2—C7—C7i91.0 (3)C13—C14—C15—C100.7 (5)
C1—C2—C7—C7i88.1 (3)C11—C10—C15—C140.2 (4)
C6—C1—N8—C942.4 (3)C9—C10—C15—C14179.1 (3)
C2—C1—N8—C9140.9 (2)
Symmetry code: (i) x+2, y, z.
 

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