N,N′-Bis(2-pyridyl­ethyl)­pyromellitic di­imide

Lü, X.; Su, C.; Kang, B.; Ng, S.W.

doi:10.1107/S1600536804005409

N,N′-Bis(2-pyridylethyl)pyromellitic diimide

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 C_pyridyl—C $_{\rm methylene}$ —C $_{\rm methylene}$ —N_imido fragment is in an anti conformation [torsion angle = 168.3 (2)°].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804005409/su6084sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804005409/su6084Isup2.hkl Contains datablock I

CCDC reference: 238787

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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

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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

C₂₄H₁₈N₄O₄	F(000) = 444
M_r = 426.42	D_x = 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	R_int = 0.023
Graphite monochromator	θ_max = 27.0°, θ_min = 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(F_o²) + (0.0666P)² + 0.0976P] where P = (F_o² + 2F_c²)/3
2171 reflections	(Δ/σ)_max = 0.001
145 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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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N,N′-Bis(2-pyridyl­ethyl)­pyromellitic di­imide

Supporting information

Key indicators

checkCIF/PLATON results

N,N′-Bis(2-pyridylethyl)pyromellitic diimide