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N,N′-Bis(2-pyridyl­ethyl)­pyromellitic di­imide, C24H18N4O4, exists as a centrosymmetric monomeric mol­ecule. Adjacent mol­ecules are linked by weak C—H...O and C—H...N interactions into a linear ribbon-like structure. The Cpyridyl—C_{\rm methylene}—C_{\rm methylene}—Nimido fragment is in an anti conformation [torsion angle = 168.3 (2)°].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804005409/su6084sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804005409/su6084Isup2.hkl
Contains datablock I

CCDC reference: 238787

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.124
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

N,N'-bis(2-pyridylethyl)pyromellitic diimide top
Crystal data top
C24H18N4O4F(000) = 444
Mr = 426.42Dx = 1.422 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 748 reflections
a = 5.2484 (7) Åθ = 2.7–26.5°
b = 8.125 (1) ŵ = 0.10 mm1
c = 23.398 (3) ÅT = 298 K
β = 93.422 (2)°Block, colourless
V = 996.0 (2) Å30.50 × 0.17 × 0.15 mm
Z = 2
Data collection top
Bruker SMART area-detector
diffractometer
1469 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 27.0°, θmin = 1.7°
φ and ω scansh = 66
6073 measured reflectionsk = 810
2171 independent reflectionsl = 2929
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0666P)2 + 0.0976P]
where P = (Fo2 + 2Fc2)/3
2171 reflections(Δ/σ)max = 0.001
145 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.26 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0045 (2)0.17145 (15)0.51859 (5)0.0599 (3)
O20.7230 (2)0.26283 (16)0.63290 (5)0.0621 (4)
N10.2161 (3)0.3535 (2)0.63783 (6)0.0608 (4)
N20.3532 (3)0.18215 (17)0.58342 (5)0.0503 (4)
C10.1989 (4)0.4709 (2)0.67734 (8)0.0655 (5)
H10.06470.54550.67290.079*
C20.3662 (4)0.4881 (2)0.72391 (7)0.0652 (5)
H20.34650.57190.75040.078*
C30.5629 (4)0.3792 (3)0.73054 (8)0.0737 (6)
H30.67950.38630.76200.088*
C40.5862 (4)0.2585 (2)0.69008 (8)0.0638 (5)
H40.72070.18390.69370.077*
C50.4101 (3)0.2483 (2)0.64420 (7)0.0468 (4)
C60.4265 (4)0.1141 (2)0.60021 (7)0.0556 (4)
H6a0.34630.15110.56400.067*
H6b0.60430.09070.59440.067*
C70.2959 (3)0.0416 (2)0.61904 (7)0.0533 (4)
H7a0.11280.02410.61730.064*
H7b0.35090.06540.65850.064*
C80.2041 (3)0.2325 (2)0.53506 (7)0.0465 (4)
C90.3415 (3)0.37443 (19)0.51135 (6)0.0433 (4)
C100.5570 (3)0.40575 (19)0.54686 (6)0.0430 (4)
C110.5664 (3)0.2803 (2)0.59351 (7)0.0483 (4)
C120.7227 (3)0.5330 (2)0.53708 (6)0.0457 (4)
H120.86630.55490.56110.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0585 (8)0.0573 (7)0.0624 (7)0.0036 (6)0.0093 (6)0.0007 (6)
O20.0650 (8)0.0714 (8)0.0477 (7)0.0018 (6)0.0143 (6)0.0123 (6)
N10.0574 (9)0.0709 (10)0.0527 (8)0.0103 (7)0.0079 (7)0.0060 (7)
N20.0529 (8)0.0496 (8)0.0479 (7)0.0037 (7)0.0017 (6)0.0072 (6)
C10.0649 (12)0.0669 (12)0.0643 (11)0.0148 (10)0.0015 (9)0.0050 (10)
C20.0798 (14)0.0610 (12)0.0545 (10)0.0048 (10)0.0033 (9)0.0108 (8)
C30.0793 (14)0.0744 (13)0.0636 (12)0.0056 (11)0.0266 (10)0.0083 (10)
C40.0591 (11)0.0563 (11)0.0729 (12)0.0065 (9)0.0213 (9)0.0034 (9)
C50.0484 (9)0.0463 (9)0.0454 (8)0.0053 (7)0.0010 (7)0.0039 (7)
C60.0621 (11)0.0552 (10)0.0495 (9)0.0033 (9)0.0032 (8)0.0015 (8)
C70.0554 (10)0.0533 (10)0.0512 (9)0.0060 (8)0.0039 (7)0.0088 (8)
C80.0485 (9)0.0453 (9)0.0453 (8)0.0078 (7)0.0008 (7)0.0030 (7)
C90.0456 (9)0.0415 (8)0.0422 (8)0.0078 (7)0.0022 (6)0.0043 (6)
C100.0460 (9)0.0441 (9)0.0382 (7)0.0099 (7)0.0021 (6)0.0011 (6)
C110.0500 (9)0.0525 (10)0.0418 (8)0.0096 (8)0.0021 (7)0.0000 (7)
C120.0447 (9)0.0507 (9)0.0404 (8)0.0078 (7)0.0080 (6)0.0025 (7)
Geometric parameters (Å, º) top
O1—C81.201 (2)C9—C101.386 (2)
O2—C111.206 (2)C9—C12i1.385 (2)
N1—C11.335 (2)C10—C111.492 (2)
N1—C51.331 (2)C10—C121.379 (2)
N2—C111.383 (2)C1—H10.93
N2—C71.456 (2)C2—H20.93
N2—C81.398 (2)C3—H30.93
C1—C21.365 (2)C4—H40.93
C2—C31.362 (3)C6—H6a0.97
C3—C41.373 (3)C6—H6b0.97
C4—C51.377 (2)C7—H7a0.97
C5—C61.505 (2)C7—H7b0.97
C6—C71.517 (2)C12—H120.93
C8—C91.485 (2)
C1—N1—C5117.7 (2)O2—C11—C10129.1 (2)
C7—N2—C8124.6 (1)N2—C11—C10106.1 (1)
C7—N2—C11123.2 (1)N1—C1—H1118.0
C8—N2—C11112.2 (1)C2—C1—H1118.0
N1—C1—C2124.0 (2)C3—C2—H2120.9
C1—C2—C3118.1 (2)C1—C2—H2120.9
C2—C3—C4118.9 (2)C2—C3—H3120.5
C3—C4—C5119.8 (2)C4—C3—H3120.5
N1—C5—C4121.5 (2)C3—C4—H4120.1
N1—C5—C6117.6 (2)C5—C4—H4120.1
C4—C5—C6120.9 (2)C5—C6—H6a109.4
C5—C6—C7111.1 (1)C7—C6—H6a109.4
N2—C7—C6112.1 (1)C5—C6—H6b109.4
O1—C8—N2125.0 (2)C7—C6—H6b109.4
O1—C8—C9129.4 (2)H6a—C6—H6b108.0
N2—C8—C9105.6 (1)N2—C7—H7a109.2
C8—C9—C10108.4 (1)C6—C7—H7a109.2
C8—C9—C12i128.9 (2)N2—C7—H7b109.2
C10—C9—C12i122.7 (2)C6—C7—H7b109.2
C9—C10—C11107.7 (1)H7a—C7—H7b107.9
C9—C10—C12122.6 (1)C10—C12—H12122.7
C11—C10—C12129.8 (1)C9i—C12—H12122.7
O2—C11—N2124.8 (2)
C5—N1—C1—C20.7 (3)N2—C8—C9—C12i178.6 (2)
N1—C1—C2—C30.0 (3)O1—C8—C9—C10176.5 (2)
C1—C2—C3—C40.7 (3)N2—C8—C9—C102.0 (2)
C2—C3—C4—C50.8 (3)C12i—C9—C10—C120.8 (2)
C1—N1—C5—C40.5 (3)C8—C9—C10—C12178.6 (1)
C1—N1—C5—C6178.9 (2)C12i—C9—C10—C11178.9 (1)
C3—C4—C5—N10.2 (3)C8—C9—C10—C111.7 (2)
C3—C4—C5—C6178.1 (2)C8—N2—C11—O2179.3 (2)
N1—C5—C6—C793.2 (2)C7—N2—C11—O21.6 (2)
C4—C5—C6—C785.2 (2)C8—N2—C11—C100.6 (2)
C11—N2—C7—C686.3 (2)C7—N2—C11—C10178.5 (1)
C8—N2—C7—C692.7 (2)C12—C10—C11—O20.3 (3)
C5—C6—C7—N2168.3 (2)C9—C10—C11—O2179.4 (2)
C11—N2—C8—O1177.0 (2)C12—C10—C11—N2179.6 (1)
C7—N2—C8—O13.9 (3)C9—C10—C11—N20.7 (2)
C11—N2—C8—C91.6 (2)C9—C10—C12—C9i0.8 (2)
C7—N2—C8—C9177.5 (1)C11—C10—C12—C9i178.9 (1)
O1—C8—C9—C12i2.9 (3)
Symmetry code: (i) x+1, y+1, z+1.
 

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