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N,
N′-Bis(2-pyridylethyl)pyromellitic diimide, C
24H
18N
4O
4, 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 C
pyridyl—C
—C
—N
imido fragment is in an
anti conformation [torsion angle = 168.3 (2)°].
Supporting information
CCDC reference: 238787
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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
C24H18N4O4 | F(000) = 444 |
Mr = 426.42 | Dx = 1.422 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 748 reflections |
a = 5.2484 (7) Å | θ = 2.7–26.5° |
b = 8.125 (1) Å | µ = 0.10 mm−1 |
c = 23.398 (3) Å | T = 298 K |
β = 93.422 (2)° | Block, colourless |
V = 996.0 (2) Å3 | 0.50 × 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 tube | Rint = 0.023 |
Graphite monochromator | θmax = 27.0°, θmin = 1.7° |
φ and ω scans | h = −6→6 |
6073 measured reflections | k = −8→10 |
2171 independent reflections | l = −29→29 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-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 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.0045 (2) | 0.17145 (15) | 0.51859 (5) | 0.0599 (3) | |
O2 | 0.7230 (2) | 0.26283 (16) | 0.63290 (5) | 0.0621 (4) | |
N1 | 0.2161 (3) | −0.3535 (2) | 0.63783 (6) | 0.0608 (4) | |
N2 | 0.3532 (3) | 0.18215 (17) | 0.58342 (5) | 0.0503 (4) | |
C1 | 0.1989 (4) | −0.4709 (2) | 0.67734 (8) | 0.0655 (5) | |
H1 | 0.0647 | −0.5455 | 0.6729 | 0.079* | |
C2 | 0.3662 (4) | −0.4881 (2) | 0.72391 (7) | 0.0652 (5) | |
H2 | 0.3465 | −0.5719 | 0.7504 | 0.078* | |
C3 | 0.5629 (4) | −0.3792 (3) | 0.73054 (8) | 0.0737 (6) | |
H3 | 0.6795 | −0.3863 | 0.7620 | 0.088* | |
C4 | 0.5862 (4) | −0.2585 (2) | 0.69008 (8) | 0.0638 (5) | |
H4 | 0.7207 | −0.1839 | 0.6937 | 0.077* | |
C5 | 0.4101 (3) | −0.2483 (2) | 0.64420 (7) | 0.0468 (4) | |
C6 | 0.4265 (4) | −0.1141 (2) | 0.60021 (7) | 0.0556 (4) | |
H6a | 0.3463 | −0.1511 | 0.5640 | 0.067* | |
H6b | 0.6043 | −0.0907 | 0.5944 | 0.067* | |
C7 | 0.2959 (3) | 0.0416 (2) | 0.61904 (7) | 0.0533 (4) | |
H7a | 0.1128 | 0.0241 | 0.6173 | 0.064* | |
H7b | 0.3509 | 0.0654 | 0.6585 | 0.064* | |
C8 | 0.2041 (3) | 0.2325 (2) | 0.53506 (7) | 0.0465 (4) | |
C9 | 0.3415 (3) | 0.37443 (19) | 0.51135 (6) | 0.0433 (4) | |
C10 | 0.5570 (3) | 0.40575 (19) | 0.54686 (6) | 0.0430 (4) | |
C11 | 0.5664 (3) | 0.2803 (2) | 0.59351 (7) | 0.0483 (4) | |
C12 | 0.7227 (3) | 0.5330 (2) | 0.53708 (6) | 0.0457 (4) | |
H12 | 0.8663 | 0.5549 | 0.5611 | 0.055* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0585 (8) | 0.0573 (7) | 0.0624 (7) | −0.0036 (6) | −0.0093 (6) | −0.0007 (6) |
O2 | 0.0650 (8) | 0.0714 (8) | 0.0477 (7) | 0.0018 (6) | −0.0143 (6) | 0.0123 (6) |
N1 | 0.0574 (9) | 0.0709 (10) | 0.0527 (8) | −0.0103 (7) | −0.0079 (7) | 0.0060 (7) |
N2 | 0.0529 (8) | 0.0496 (8) | 0.0479 (7) | 0.0037 (7) | −0.0017 (6) | 0.0072 (6) |
C1 | 0.0649 (12) | 0.0669 (12) | 0.0643 (11) | −0.0148 (10) | 0.0015 (9) | 0.0050 (10) |
C2 | 0.0798 (14) | 0.0610 (12) | 0.0545 (10) | 0.0048 (10) | 0.0033 (9) | 0.0108 (8) |
C3 | 0.0793 (14) | 0.0744 (13) | 0.0636 (12) | 0.0056 (11) | −0.0266 (10) | 0.0083 (10) |
C4 | 0.0591 (11) | 0.0563 (11) | 0.0729 (12) | −0.0065 (9) | −0.0213 (9) | 0.0034 (9) |
C5 | 0.0484 (9) | 0.0463 (9) | 0.0454 (8) | 0.0053 (7) | 0.0010 (7) | −0.0039 (7) |
C6 | 0.0621 (11) | 0.0552 (10) | 0.0495 (9) | 0.0033 (9) | 0.0032 (8) | 0.0015 (8) |
C7 | 0.0554 (10) | 0.0533 (10) | 0.0512 (9) | 0.0060 (8) | 0.0039 (7) | 0.0088 (8) |
C8 | 0.0485 (9) | 0.0453 (9) | 0.0453 (8) | 0.0078 (7) | −0.0008 (7) | −0.0030 (7) |
C9 | 0.0456 (9) | 0.0415 (8) | 0.0422 (8) | 0.0078 (7) | −0.0022 (6) | −0.0043 (6) |
C10 | 0.0460 (9) | 0.0441 (9) | 0.0382 (7) | 0.0099 (7) | −0.0021 (6) | −0.0011 (6) |
C11 | 0.0500 (9) | 0.0525 (10) | 0.0418 (8) | 0.0096 (8) | −0.0021 (7) | 0.0000 (7) |
C12 | 0.0447 (9) | 0.0507 (9) | 0.0404 (8) | 0.0078 (7) | −0.0080 (6) | −0.0025 (7) |
Geometric parameters (Å, º) top
O1—C8 | 1.201 (2) | C9—C10 | 1.386 (2) |
O2—C11 | 1.206 (2) | C9—C12i | 1.385 (2) |
N1—C1 | 1.335 (2) | C10—C11 | 1.492 (2) |
N1—C5 | 1.331 (2) | C10—C12 | 1.379 (2) |
N2—C11 | 1.383 (2) | C1—H1 | 0.93 |
N2—C7 | 1.456 (2) | C2—H2 | 0.93 |
N2—C8 | 1.398 (2) | C3—H3 | 0.93 |
C1—C2 | 1.365 (2) | C4—H4 | 0.93 |
C2—C3 | 1.362 (3) | C6—H6a | 0.97 |
C3—C4 | 1.373 (3) | C6—H6b | 0.97 |
C4—C5 | 1.377 (2) | C7—H7a | 0.97 |
C5—C6 | 1.505 (2) | C7—H7b | 0.97 |
C6—C7 | 1.517 (2) | C12—H12 | 0.93 |
C8—C9 | 1.485 (2) | | |
| | | |
C1—N1—C5 | 117.7 (2) | O2—C11—C10 | 129.1 (2) |
C7—N2—C8 | 124.6 (1) | N2—C11—C10 | 106.1 (1) |
C7—N2—C11 | 123.2 (1) | N1—C1—H1 | 118.0 |
C8—N2—C11 | 112.2 (1) | C2—C1—H1 | 118.0 |
N1—C1—C2 | 124.0 (2) | C3—C2—H2 | 120.9 |
C1—C2—C3 | 118.1 (2) | C1—C2—H2 | 120.9 |
C2—C3—C4 | 118.9 (2) | C2—C3—H3 | 120.5 |
C3—C4—C5 | 119.8 (2) | C4—C3—H3 | 120.5 |
N1—C5—C4 | 121.5 (2) | C3—C4—H4 | 120.1 |
N1—C5—C6 | 117.6 (2) | C5—C4—H4 | 120.1 |
C4—C5—C6 | 120.9 (2) | C5—C6—H6a | 109.4 |
C5—C6—C7 | 111.1 (1) | C7—C6—H6a | 109.4 |
N2—C7—C6 | 112.1 (1) | C5—C6—H6b | 109.4 |
O1—C8—N2 | 125.0 (2) | C7—C6—H6b | 109.4 |
O1—C8—C9 | 129.4 (2) | H6a—C6—H6b | 108.0 |
N2—C8—C9 | 105.6 (1) | N2—C7—H7a | 109.2 |
C8—C9—C10 | 108.4 (1) | C6—C7—H7a | 109.2 |
C8—C9—C12i | 128.9 (2) | N2—C7—H7b | 109.2 |
C10—C9—C12i | 122.7 (2) | C6—C7—H7b | 109.2 |
C9—C10—C11 | 107.7 (1) | H7a—C7—H7b | 107.9 |
C9—C10—C12 | 122.6 (1) | C10—C12—H12 | 122.7 |
C11—C10—C12 | 129.8 (1) | C9i—C12—H12 | 122.7 |
O2—C11—N2 | 124.8 (2) | | |
| | | |
C5—N1—C1—C2 | 0.7 (3) | N2—C8—C9—C12i | 178.6 (2) |
N1—C1—C2—C3 | 0.0 (3) | O1—C8—C9—C10 | 176.5 (2) |
C1—C2—C3—C4 | −0.7 (3) | N2—C8—C9—C10 | −2.0 (2) |
C2—C3—C4—C5 | 0.8 (3) | C12i—C9—C10—C12 | 0.8 (2) |
C1—N1—C5—C4 | −0.5 (3) | C8—C9—C10—C12 | −178.6 (1) |
C1—N1—C5—C6 | −178.9 (2) | C12i—C9—C10—C11 | −178.9 (1) |
C3—C4—C5—N1 | −0.2 (3) | C8—C9—C10—C11 | 1.7 (2) |
C3—C4—C5—C6 | 178.1 (2) | C8—N2—C11—O2 | 179.3 (2) |
N1—C5—C6—C7 | 93.2 (2) | C7—N2—C11—O2 | −1.6 (2) |
C4—C5—C6—C7 | −85.2 (2) | C8—N2—C11—C10 | −0.6 (2) |
C11—N2—C7—C6 | −86.3 (2) | C7—N2—C11—C10 | 178.5 (1) |
C8—N2—C7—C6 | 92.7 (2) | C12—C10—C11—O2 | −0.3 (3) |
C5—C6—C7—N2 | 168.3 (2) | C9—C10—C11—O2 | 179.4 (2) |
C11—N2—C8—O1 | −177.0 (2) | C12—C10—C11—N2 | 179.6 (1) |
C7—N2—C8—O1 | 3.9 (3) | C9—C10—C11—N2 | −0.7 (2) |
C11—N2—C8—C9 | 1.6 (2) | C9—C10—C12—C9i | −0.8 (2) |
C7—N2—C8—C9 | −177.5 (1) | C11—C10—C12—C9i | 178.9 (1) |
O1—C8—C9—C12i | −2.9 (3) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
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