Three-dimensional supramolecular structures in (E,E)-N,N′-bis­(4-nitro­benzyl­idene)butane-1,4-diamine and (E,E)-N,N′-bis­(4-nitro­benzyl­idene)­hexane-1,6-diamine

Glidewell, C.; Low, J.N.; Skakle, J.M.S.; Wardell, J.L.

doi:10.1107/S0108270105035766

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 62| Part 1| January 2006| Pages o1-o4

doi:10.1107/S0108270105035766

Three-dimensional supramolecular structures in (E,E)-N,N′-bis(4-nitrobenzylidene)butane-1,4-diamine and (E,E)-N,N′-bis(4-nitrobenzylidene)hexane-1,6-diamine

Christopher Glidewell,^a ^* John N. Low,^b Janet M. S. Skakle ^b and James L. Wardell ^c

^aSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and ^cInstituto de Química, Departamento de Química Inorgânica, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ, Brazil
^*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 28 October 2005; accepted 1 November 2005; online 10 December 2005)

In both (E,E)-N,N′-bis(4-nitrobenzylidene)butane-1,4-diamine, C₁₈H₁₈N₄O₄, (III), and (E,E)-N,N′-bis(4-nitrobenzylidene)hexane-1,6-diamine, C₂₀H₂₂N₄O₄, (IV), the molecules lie across centres of inversion in space groups P $[\overline{1}]$ and P2₁/c, respectively. In (III), the three-dimensional supramolecular structure is built from π-stacked chains of edge-fused R₂²(30) rings, while in (IV), chains of edge-fused R₂²(38) rings are linked by dipolar nitro–nitro interactions.

Comment

In this paper, we describe the structures of two compounds in the series 4-O₂NC₆H₄CH=N–(CH₂)_n–N=CHC₆H₄NO₂, viz. for n = 4, compound (III), or n = 6, compound (IV) (see scheme). We have recently reported the molecular and supramolecular structures of N,N′-bis(4-nitrobenzylidene)ethane-1,2-diamine, (II), where n = 2 (Bomfim et al., 2005 ). The molecules of (II), which lie across centres of inversion in the space group P2₁/n, are linked into sheets by a single C—H⋯O hydrogen bond, and these sheets are further linked by an aromatic π–π stacking interaction. By contrast, in (E,E)-1-(3-nitrophenyl)-4-(4-nitrophenyl)-2,3-diaza-1,3-butadiene, (I), where there are no methylene groups between the two –CH=N– units, the centrosymmetric molecules are linked directly into a three-dimensional framework structure by means of two independent C—H⋯O hydrogen bonds (Glidewell et al., 2006 ). Intrigued by the differences in the aggregation patterns of these two compounds, we have now undertaken a more extended study involving compounds (III) and (IV), and report their structures here.

Compounds (I)–(IV) all lie across centres of inversion and all have the E,E configuration at the C=N double bonds. In each of compounds (III) and (IV) (Figs. 1 and 2), the reference molecule was selected, for the sake of convenience, as that centred across ( $[{1 \over 2}, {1 \over 2}, {1 \over 2}]$ ) in the space groups P $[\overline{1}]$ and P2₁/c, respectively.

In each of compounds (II)–(IV), the nitro groups are essentially coplanar with the adjacent aryl rings, as shown by the relevant torsion angles (Table 1) and, likewise, the C1—C11—N11—C12 fragments are effectively coplanar with these rings. However, the skeletons in the polymethylene spacer units adopt conformations which are very far from planar.

In compound (III) (Fig. 1), the molecules are linked into chains of edge-fused rings, which can alternatively be described as molecular ladders, by a single C—H⋯O hydrogen bond (Table 2), and these chains are further linked into a three-dimensional framework by two independent π–π stacking interactions. The methine C11 atoms at (x, y, z) and (1 − x, 1 − y, 1 − z) are parts of the molecule centred at ( $[{1 \over 2}, {1 \over 2}, {1 \over 2}]$ ). These atoms act as hydrogen-bond donors to the nitro atoms O42 at (x, y, 1 + z) and (1 − x, 1 − y, −z), respectively, which themselves are parts of the molecules centred at ( $[{1 \over 2}, {1 \over 2}, {3 \over 2}]$ ) and ( $[{1 \over 2}, {1 \over 2}, -{1 \over 2}]$ ), respectively. Propagation by translation and inversion of this single hydrogen bond then generates a chain of edge-fused R₂²(30) rings (Bernstein et al., 1995 ) running along ( $[{1 \over 2}, {1 \over 2}, z]$ ) (Fig. 3).

The aryl rings at (x, y, z) and (−x, 1 − y, −z), which form parts of molecules centred at ( $[{1 \over 2}, {1 \over 2}, {1 \over 2}]$ ) and ( $[-{1 \over 2}, {1 \over 2}, -{1 \over 2}]$ ), are strictly parallel, with an interplanar spacing of 3.738 (2) Å; the centroid separation is 3.377 (2) Å, corresponding to a ring offset of 1.602 (2) Å. Propagation by inversion of this stacking interaction then generates a chain running parallel to the [101] direction (Fig. 4). Similarly, the rings at (x, y, z) and (−x, 2 − y, −z) are parallel, with an interplanar spacing of 3.630 (2) Å, and a centroid separation and offset of 3.378 (2) and 1.327 (2) Å, respectively. This stacking interaction generates a chain parallel to the [1 $[\overline{1}]$ 1] direction (Fig. 5). The combination of the [001], [101] and [1 $[\overline{1}]$ 1] chains suffices to link all of the molecules into a single three-dimensional structure.

In compound (IV) (Fig. 2), the molecules are linked by a single C—H⋯O hydrogen bond (Table 2), but aromatic π–π stacking interactions are absent from the structure. Instead, the hydrogen-bonded chains are linked, again into a three-dimensional structure, by a single dipolar nitro–nitro interaction. The aryl C2 atoms at (x, y, z) and (1 − x, 1 − y, 1 − z) act as hydrogen-bond donors to nitro atoms O42 at (−1 + x, −1 + y, z) and (2 − x, 2 − y, 1 − z), which are themselves parts of the molecules centred at ( $[-{1 \over 2}, -{1 \over 2}, {1 \over 2}]$ ) and ( $[{3 \over 2}, {3 \over 2}, {1 \over 2}]$ ), respectively. Propagation of this single hydrogen bond thus generates a chain of edge-fused R₂²(38) rings running parallel to the [110] direction (Fig. 6).

Nitro atom O41 at (x, y, z) forms a short dipolar contact with nitro atom N4 at (3 − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z); the dimensions of this contact are N⋯O = 2.893 (2) Å, N—O⋯N = 117.2 (2)° and O⋯N—C = 118.4 (2)°; so that it is somewhat reminiscent of the type I (perpendicular) dipolar carbonyl–carbonyl interaction (Allen et al., 1998 ). In this manner, the molecule centred at ( $[{1 \over 2}, {1 \over 2}, {1 \over 2}]$ ) acts as donor to the molecules centred at ( $[{5 \over 2}, 1, 1]$ ), and ( $[-{3 \over 2}, 0, 0]$ ) and as acceptor from those centred at ( $[{5 \over 2}, 0, 1]$ ) and ( $[-{3 \over 2}, 1, 0]$ ), so generating a ( $[\overline{1}]$ 04) sheet in the form of a (4,4)-net built from a single type of R₄⁴(46) ring (Starbuck et al., 1999 ) (Fig. 7). The combination of these sheets and the hydrogen-bonded [110] chains links all the molecules into a single three-dimensional framework.

Hence, although compounds (I)–(IV) all form three-dimensional supramolecular structures, no two exhibit the same range of direction-specific intermolecular interactions, and the details of the framework formation are different for each.

Figure 1
The molecule of compound (III)

, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Atoms labelled with the suffix `a' are at the symmetry position (1 − x, 1 − y, 1 − z).

Figure 2
The molecule of compound (IV)

, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Atoms labelled with the suffix `a' are at the symmetry position (1 − x, 1 − y, 1 − z).

Figure 3
A stereoview of part of the crystal structure of (III)

, showing the formation of a chain of edge-fused R₂²(30) rings along [001]. For the sake of clarity, H atoms not involved in the motif shown have been omitted.

Figure 4
A stereoview of part of the crystal structure of (III)

, showing the formation of a π-stacked chain along [101]. For the sake of clarity, all H atoms have been omitted.

Figure 5
A stereoview of part of the crystal structure of (III)

, showing the formation of a π-stacked chain along [1 $[\overline{1}]$ 1]. For the sake of clarity, all H atoms have been omitted.

Figure 6
Part of the crystal structure of (IV)

, showing the formation of a chain of edge-fused R₂²(38) rings along [110]. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*), hash (#), ampersand (&), dollar sign ($) or `at' symbol (@) are at the symmetry positions (1 − x, 1 − y, 1 − z), (−1 + x, −1 + y, z), (1 + x, 1 + y, z), (2 − x, 2 − y, 1 − z) and (−x, −y, 1 − z), respectively.

Figure 7
A stereoview of part of the crystal structure of (IV)

, showing the formation of a ( $[\overline{1}]$ 04) sheet of R₄⁴(46) rings generated by the dipolar nitro–nitro interaction. For the sake of clarity, all H atoms have been omitted.

Experimental

A solution of 4-nitrobenzaldehyde (8 mmol) and 1,4-diaminobutane (4 mmol) in methanol (25 ml) was heated under reflux for 30 min. After cooling, the solvent was removed under reduced pressure and the product was recrystallized from methanol–1,2-dichloroethane (1:1 v/v) to yield crystals of (III) suitable for single-crystal X-ray diffraction (m.p. 438–439 K). Compound (IV) was prepared in a similar way from 4-nitrobenzaldehyde and 1,6-diaminohexane, but it was recrystallized from 1,2-dichloroethane (m.p. 408–410 K).

Compound (III)

Crystal data

C₁₈H₁₈N₄O₄
M_r = 354.36
Triclinic, $[P \overline 1]$
a = 7.1162 (4) Å
b = 7.1895 (2) Å
c = 9.1695 (4) Å
α = 83.210 (3)°
β = 78.920 (2)°
γ = 64.808 (3)°
V = 416.25 (3) Å³
Z = 1
D_x = 1.414 Mg m⁻³
Mo Kα radiation
Cell parameters from 1895 reflections
θ = 3.1–27.6°
μ = 0.10 mm⁻¹
T = 120 (2) K
Lath, colourless
0.46 × 0.34 × 0.13 mm

Data collection

Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 2003 )T_min = 0.944, T_max = 0.987
8689 measured reflections
1895 independent reflections
1589 reflections with I > 2σ(I)
R_int = 0.028
θ_max = 27.6°
h = −9 → 9
k = −9 → 9
l = −11 → 11

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.114
S = 1.05
1893 reflections
118 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0652P)² + 0.1082P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Compound (IV)

Crystal data

C₂₀H₂₂N₄O₄
M_r = 382.42
Monoclinic, P 2₁ /c
a = 6.1908 (3) Å
b = 4.9761 (2) Å
c = 30.1095 (15) Å
β = 94.331 (3)°
V = 924.91 (7) Å³
Z = 2
D_x = 1.373 Mg m⁻³
Mo Kα radiation
Cell parameters from 2083 reflections
θ = 3.3–27.6°
μ = 0.10 mm⁻¹
T = 120 (2) K
Lath, colourless
0.44 × 0.30 × 0.12 mm

Data collection

Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)T_min = 0.952, T_max = 0.988
7409 measured reflections
2083 independent reflections
1516 reflections with I > 2σ(I)
R_int = 0.041
θ_max = 27.6°
h = −8 → 7
k = −6 → 6
l = −31 → 39

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.113
S = 1.06
2083 reflections
127 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0532P)² + 0.2054P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Selected torsion angles (°) for compounds (II)–(IV)

Parameter	(II)†	(III)	(IV)
C3—C4—N4—O41	−5.86 (15)	0.96 (15)	−2.3 (2)
C2—C1—C11—N11	177.91 (9)	−171.77 (10)	172.20 (15)
C1—C11—N11—C12	−176.58 (8)	−179.54 (9)	−179.72 (12)
C11—N11—C12—C12ⁱ	118.31 (13)
C11—N11—C12—C13		111.42 (11)	111.90 (15)
N11—C12—C13—C13ⁱ		−65.67 (15)
N11—C12—C13—C14			−70.53 (15)
C12—C13—C14—C14ⁱ			−179.76 (15)
Symmetry code: (i) 1-x, 1-y, 1-z.

†Data for compound (II)

from Bomfim et al. (2005

Table 2
Hydrogen-bond geometry (Å, °) for compounds (III) and (IV)

Compound	D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
(III)	C11—H11⋯O42ⁱ	0.95	2.60	3.502 (2)	159
(IV)	C2—H2⋯O42ⁱⁱ	0.95	2.50	3.349 (2)	149
Symmetry codes: (i) x, y, 1+z; (ii) -1+x, -1+y, z.

Crystals of compound (III) are triclinic. The space group P $[\overline{1}]$ was selected and confirmed by the subsequent structure analysis. For compound (IV), the space group P2₁/c was uniquely determined from the systematic absences. All H atoms were located in difference maps and then treated as riding atoms, with C—H distances of 0.95 or 0.99 Å, and with U_iso(H) = 1.2U_eq(C).

For both compounds, data collection: COLLECT (Nonius, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003 ) and SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, III, IV. DOI: 10.1107/S0108270105035766/sk1882sup1.cif

Structure factors: contains datablock III. DOI: 10.1107/S0108270105035766/sk1882IIIsup2.hkl

Structure factors: contains datablock IV. DOI: 10.1107/S0108270105035766/sk1882IVsup3.hkl

Comment top

In this paper, we describe the structures of two compounds in the series 4-O₂NC₆H₄CH═N—(CH₂)_n—N═CHC₆H₄NO₂, where n = 4, compound (III), or n = 6, compound (IV) (see scheme). We have recently reported the molecular and supramolecular structures of N,N'-bis(4-nitrobenzylidene)ethane-1,2-diamine, (II), where n = 2 (Bomfim et al., 2005). The molecules of (II), which lie across centres of inversion in space group P2₁/n, are linked into sheets by a single C—H···O hydrogen bond, and these sheets are further linked by an aromatic π–π stacking interaction. By contrast, in (E,E)-1-(3-nitrophenyl)-4-(4-nitrophenyl)-2,3-diaza-1,3-butadiene, compound (I), where there are no methylene groups between the two –CH═N– units, the centrosymmetric molecules are linked directly into a three-dimensional framework structure by means of two independent C—H···O hydrogen bonds (Glidewell et al., 2006). Intrigued by the differences in the aggregation patterns of these two compounds, we have now undertaken a more extended study involving compounds (III) and (IV), and report their structures here.

Compounds (I)–(IV) all lie across centres of inversion and all have the (E,E) configuration at the C═N double bonds. In each of compounds (III) and (IV) (Figs. 1 and 2), the reference molecule was selected, for the sake of convenience, as that centred across (1/2, 1/2, 1/2), in space groups P1 and P2₁/c, respectively

In each of compounds (II)–(IV), the nitro groups are essentially co-planar with the adjacent aryl rings, as shown by the relevant torsion angles (Table 1) and, likewise, the C1—C11—N11—C12 fragments are effectively co-planar with these rings. However, the skeletons in the polymethylene spacer units adopt conformations which are very far from planar.

In compound (III) (Fig. 1), the molecules are linked into chains of edge-fused rings, which can alternatively be described as molecular ladders, by a single C—H···O hydrogen bond (Table 2), and these chains are further linked into a three-dimensional framework by two independent π–π stacking interactions. The methine atoms C11 at (x, y, z) and (1 - x, 1 - y, 1 - z) are parts of the molecule centred at (1/2, 1/2, 1/2). These atoms act as hydrogen-bond donors to the nitro atoms O42 at (x, y, 1 + z) and (1 - x, 1 - y, -z), respectively, which themselves are parts of the molecules centred at (1/2, 1/2, 3/2) and (1/2, 1/2, -1/2), respectively. Propagation by translation and inversion of this single hydrogen bond then generates a chain of edge-fused R²₂(30) rings (Bernstein et al., 1995) running along (1/2, 1/2, z) (Fig. 3).

The aryl rings at (x, y, z) and (-x, 1 - y, -z), which form parts of molecules centred at (1/2, 1/2, 1/2) and (-1/2, 1/2, -1/2), are strictly parallel, with an interplanar spacing of 3.738 (2) Å; the centroid separation is 3.377 (2) Å, corresponding to a ring offset of 1.602 (2) Å. Propagation by inversion of this stacking interaction then generates a chain running parallel to the [101] direction (Fig. 4). Similarly, the rings at (x, y, z) and (-x, 2 - y, -z) are parallel, with an interplanar spacing of 3.630 (2) °, and a centroid separation and offset of 3.378 (2) and 1.327 (2) Å, respectively. This stacking interaction generates a chain parallel to the [111] direction (Fig. 5). The combination of the [001], [101] and [111] chains suffices to link all of the molecules into a single three-dimensional structure.

In compound (IV) (Fig. 2), the molecules are linked by a single C—H···O hydrogen bond (Table 2), but aromatic π–π stacking interactions are absent from the structure. Instead, the hydrogen-bonded chains are linked, again into a three-dimensional structure, by a single dipolar nitro···nitro interaction. The aryl atoms C2 at (x, y, z) and (1 - x, 1 - y, 1 - z) act as hydrogen-bond donors to the nitro atoms O42 at (-1 + x, -1 + y, z) and (2 - x, 2 - y, 1 - z), which are themselves parts of the molecules centred at (-1/2, -1/2, 1/2) and (3/2, 3/2, 1/2), respectively. Propagation of this single hydrogen bond thus generates a chain of edge-fused R²₂(38) rings running parallel to the [110] direction (Fig. 6).

The nitro atom O41 at (x, y, z) forms a short dipolar contact with the nitro atom N4 at (3 - x, 1/2 + y, 3/2 - z); the dimensions of this contact are N···Oⁱ 2.893 (2) Å, N—O···Nⁱ 117.2 (2)° and O···Nⁱ—Cⁱ 118.4 (2)° [symmetry code: (i) 3 - x, 1/2 + y, 3/2 - z], so that it is somewhat reminiscent of the type I (perpendicular) dipolar carbonyl···carbonyl interaction (Allen et al., 1998). In this manner, the molecule centred at (1/2, 1/2, 1/2) acts as donor to the molecules centred at (5/2, 1, 1) and (-3/2, 0, 0) and as acceptor from those centred at (5/2, 0, 1) and (-3/2, 1, 0), so generating a (104) sheet in the form of a (4,4) net built from a single type of R⁴₄(46) ring (Starbuck et al., 1999) (Fig. 7). The combination of these sheets and the hydrogen-bonded [110] chains links all the molecules into a single three-dimensional framework.

Experimental top

A solution of 4-nitrobenzaldehyde (8 mmol) and 1,4-diaminobutane (4 mmol) in methanol (25 ml) was heated under reflux for 30 min. After cooling, the solvent was removed under reduced pressure and the resulting solid product was recrystallized from methanol–1,2-dichloroethane (1:1 v/v) to yield crystals of compound (III) suitable for single-crystal X-ray diffraction (m.p. 438–439 K). Compound (IV) was prepared in a similar way from 4-nitrobenzaldehyde and 1,6-diaminohexane, but it was recrystallized from 1,2-dichloroethane (m.p. 408–410 K).

Structure description top

Computing details top

For both compounds, data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top

	Fig. 1. The molecule of compound (III), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Atoms labelled with the suffix 'a' are at the symmetry position (1 - x, 1 - y, 1 - z).
	Fig. 2. The molecule of compound (IV), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Atoms labelled with the suffix 'a' are at the symmetry position (1 - x, 1 - y, 1 - z).
	Fig. 3. A stereoview of part of the crystal structure of (III), showing the formation of a chain of edge-fused R²₂(30) rings along [001]. For the sake of clarity, H atoms not involved in the motif shown have been omitted.
	Fig. 4. A stereoview of part of the crystal structure of (III), showing the formation of a π-stacked chain along [101]. For the sake of clarity, all H atoms have been omitted.
	Fig. 5. A stereoview of part of the crystal structure of (III), showing the formation of a π-stacked chain along [111]. For the sake of clarity, all H atoms have been omitted.
	Fig. 6. Part of the crystal structure of (IV), showing the formation of a chain of edge-fused R²₂(38) rings along [001]. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*), hash (#), ampersand (&), dollar sign ($) or `at' symbol (@) are at the symmetry positions (1 - x, 1 - y, 1 - z), (-1 + x, -1 + y, z), (1 + x, 1 + y, z), (2 - x, 2 - y, 1 - z) and (-x, -y, 1 - z), respectively.
	Fig. 7. A stereoview of part of the crystal structure of (IV), showing the formation of a (104) sheet of R⁴₄(46) rings generated by the dipolar nitro···nitro interaction. For the sake of clarity, all H atoms have been omitted.

(III) (E,E)—N,N'-bis(4-nitrobenzylidene)butane-1,4-diamine top

Crystal data top

C₁₈H₁₈N₄O₄	Z = 1
M_r = 354.36	F(000) = 186
Triclinic, P1	D_x = 1.414 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1162 (4) Å	Cell parameters from 1895 reflections
b = 7.1895 (2) Å	θ = 3.1–27.6°
c = 9.1695 (4) Å	µ = 0.10 mm⁻¹
α = 83.210 (3)°	T = 120 K
β = 78.920 (2)°	Lath, colourless
γ = 64.808 (3)°	0.46 × 0.34 × 0.13 mm
V = 416.25 (3) Å³

Data collection top

Nonius KappaCCD area-detector diffractometer	1895 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	1589 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.6°, θ_min = 3.1°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −9→9
T_min = 0.944, T_max = 0.987	l = −11→11
8689 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0652P)² + 0.1082P] where P = (F_o² + 2F_c²)/3
1893 reflections	(Δ/σ)_max < 0.001
118 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₈H₁₈N₄O₄	γ = 64.808 (3)°
M_r = 354.36	V = 416.25 (3) Å³
Triclinic, P1	Z = 1
a = 7.1162 (4) Å	Mo Kα radiation
b = 7.1895 (2) Å	µ = 0.10 mm⁻¹
c = 9.1695 (4) Å	T = 120 K
α = 83.210 (3)°	0.46 × 0.34 × 0.13 mm
β = 78.920 (2)°

Data collection top

Nonius KappaCCD area-detector diffractometer	1895 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1589 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.987	R_int = 0.028
8689 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.05	Δρ_max = 0.26 e Å⁻³
1893 reflections	Δρ_min = −0.34 e Å⁻³
118 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.04942 (18)	0.76874 (16)	0.16560 (12)	0.0166 (3)
C2	−0.16018 (18)	0.80111 (17)	0.17853 (12)	0.0180 (3)
C3	−0.24425 (18)	0.79419 (17)	0.05569 (13)	0.0182 (3)
C4	−0.11310 (18)	0.75422 (16)	−0.07985 (12)	0.0164 (3)
C5	0.09695 (18)	0.72065 (17)	−0.09719 (12)	0.0178 (3)
C6	0.17834 (18)	0.72778 (17)	0.02671 (13)	0.0175 (3)
N4	−0.20026 (16)	0.74590 (15)	−0.21094 (11)	0.0187 (2)
O41	−0.38677 (14)	0.77768 (14)	−0.19416 (10)	0.0272 (2)
O42	−0.08302 (14)	0.70788 (14)	−0.33088 (9)	0.0270 (2)
C11	0.12746 (18)	0.78186 (17)	0.30044 (12)	0.0176 (3)
N11	0.30768 (16)	0.77813 (15)	0.29785 (11)	0.0190 (2)
C12	0.36181 (19)	0.79103 (18)	0.44148 (12)	0.0195 (3)
C13	0.53546 (19)	0.58793 (17)	0.48542 (12)	0.0188 (3)
H2	−0.2472	0.8284	0.2730	0.022*
H3	−0.3873	0.8162	0.0645	0.022*
H5	0.1830	0.6934	−0.1920	0.021*
H6	0.3217	0.7048	0.0174	0.021*
H11	0.0382	0.7937	0.3936	0.021*
H12A	0.2354	0.8245	0.5187	0.023*
H12B	0.4096	0.9029	0.4353	0.023*
H13A	0.6581	0.5508	0.4048	0.023*
H13B	0.5808	0.6064	0.5762	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0197 (6)	0.0126 (5)	0.0176 (5)	−0.0072 (4)	−0.0032 (4)	0.0016 (4)
C2	0.0188 (6)	0.0181 (6)	0.0164 (5)	−0.0086 (5)	0.0008 (4)	−0.0005 (4)
C3	0.0160 (6)	0.0171 (5)	0.0218 (6)	−0.0079 (4)	−0.0023 (4)	0.0005 (4)
C4	0.0196 (6)	0.0132 (5)	0.0170 (5)	−0.0067 (4)	−0.0050 (4)	0.0010 (4)
C5	0.0185 (6)	0.0164 (5)	0.0160 (5)	−0.0065 (5)	0.0010 (4)	−0.0007 (4)
C6	0.0154 (6)	0.0161 (6)	0.0206 (6)	−0.0063 (4)	−0.0025 (4)	0.0003 (4)
N4	0.0209 (5)	0.0157 (5)	0.0192 (5)	−0.0071 (4)	−0.0039 (4)	−0.0003 (4)
O41	0.0204 (5)	0.0349 (5)	0.0287 (5)	−0.0114 (4)	−0.0072 (4)	−0.0046 (4)
O42	0.0280 (5)	0.0335 (5)	0.0177 (4)	−0.0112 (4)	−0.0020 (4)	−0.0032 (4)
C11	0.0198 (6)	0.0146 (5)	0.0163 (5)	−0.0062 (4)	−0.0011 (4)	0.0005 (4)
N11	0.0201 (5)	0.0192 (5)	0.0180 (5)	−0.0081 (4)	−0.0051 (4)	0.0019 (4)
C12	0.0213 (6)	0.0209 (6)	0.0176 (6)	−0.0095 (5)	−0.0037 (4)	−0.0009 (4)
C13	0.0194 (6)	0.0209 (6)	0.0178 (5)	−0.0094 (5)	−0.0048 (4)	−0.0002 (4)

Geometric parameters (Å, º) top

C1—C2	1.3914 (16)	N4—O42	1.2266 (13)
C1—C6	1.4000 (16)	N4—O41	1.2285 (13)
C1—C11	1.4771 (16)	C11—N11	1.2670 (16)
C2—C3	1.3880 (16)	C11—H11	0.95
C2—H2	0.95	N11—C12	1.4649 (14)
C3—C4	1.3815 (16)	C12—C13	1.5289 (16)
C3—H3	0.95	C12—H12A	0.99
C4—C5	1.3887 (16)	C12—H12B	0.99
C4—N4	1.4725 (14)	C13—C13ⁱ	1.528 (2)
C5—C6	1.3859 (16)	C13—H13A	0.99
C5—H5	0.95	C13—H13B	0.99
C6—H6	0.95

C2—C1—C6	119.64 (10)	O42—N4—C4	118.32 (10)
C2—C1—C11	118.19 (10)	O41—N4—C4	118.13 (9)
C6—C1—C11	122.17 (11)	N11—C11—C1	123.15 (10)
C3—C2—C1	121.08 (10)	N11—C11—H11	118.4
C3—C2—H2	119.5	C1—C11—H11	118.4
C1—C2—H2	119.5	C11—N11—C12	116.39 (10)
C4—C3—C2	117.85 (11)	N11—C12—C13	110.93 (9)
C4—C3—H3	121.1	N11—C12—H12A	109.5
C2—C3—H3	121.1	C13—C12—H12A	109.5
C3—C4—C5	122.77 (10)	N11—C12—H12B	109.5
C3—C4—N4	118.37 (10)	C13—C12—H12B	109.5
C5—C4—N4	118.86 (10)	H12A—C12—H12B	108.0
C6—C5—C4	118.60 (10)	C13ⁱ—C13—C12	112.57 (12)
C6—C5—H5	120.7	C13ⁱ—C13—H13A	109.1
C4—C5—H5	120.7	C12—C13—H13A	109.1
C5—C6—C1	120.06 (11)	C13ⁱ—C13—H13B	109.1
C5—C6—H6	120.0	C12—C13—H13B	109.1
C1—C6—H6	120.0	H13A—C13—H13B	107.8
O42—N4—O41	123.55 (10)

C6—C1—C2—C3	−0.22 (17)	C3—C4—N4—O42	−179.11 (10)
C11—C1—C2—C3	178.97 (10)	C5—C4—N4—O42	0.55 (15)
C1—C2—C3—C4	−0.03 (16)	C3—C4—N4—O41	0.96 (15)
C2—C3—C4—C5	0.18 (17)	C5—C4—N4—O41	−179.38 (10)
C2—C3—C4—N4	179.83 (9)	C2—C1—C11—N11	−171.77 (10)
C3—C4—C5—C6	−0.08 (17)	C6—C1—C11—N11	7.40 (17)
N4—C4—C5—C6	−179.72 (9)	C1—C11—N11—C12	−179.54 (9)
C4—C5—C6—C1	−0.19 (16)	C11—N11—C12—C13	111.42 (11)
C2—C1—C6—C5	0.33 (16)	N11—C12—C13—C13ⁱ	−65.67 (15)
C11—C1—C6—C5	−178.83 (10)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O42ⁱⁱ	0.95	2.60	3.502 (2)	159

Symmetry code: (ii) x, y, z+1.

(IV) (E,E)—N,N'-bis(4-nitrobenzylidene)hexane-1,6-diamine top

Crystal data top

C₂₀H₂₂N₄O₄	F(000) = 404
M_r = 382.42	D_x = 1.373 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2083 reflections
a = 6.1908 (3) Å	θ = 3.3–27.6°
b = 4.9761 (2) Å	µ = 0.10 mm⁻¹
c = 30.1095 (15) Å	T = 120 K
β = 94.331 (3)°	Lath, colourless
V = 924.91 (7) Å³	0.44 × 0.30 × 0.12 mm
Z = 2

Data collection top

Nonius KappaCCD area-detector diffractometer	2083 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	1516 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.6°, θ_min = 3.3°
φ and ω scans	h = −8→7
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −6→6
T_min = 0.952, T_max = 0.988	l = −31→39
7409 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0532P)² + 0.2054P] where P = (F_o² + 2F_c²)/3
2083 reflections	(Δ/σ)_max = 0.001
127 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₀H₂₂N₄O₄	V = 924.91 (7) Å³
M_r = 382.42	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.1908 (3) Å	µ = 0.10 mm⁻¹
b = 4.9761 (2) Å	T = 120 K
c = 30.1095 (15) Å	0.44 × 0.30 × 0.12 mm
β = 94.331 (3)°

Data collection top

Nonius KappaCCD area-detector diffractometer	2083 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1516 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.988	R_int = 0.041
7409 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.06	Δρ_max = 0.19 e Å⁻³
2083 reflections	Δρ_min = −0.30 e Å⁻³
127 parameters

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

	x	y	z	U_iso*/U_eq
C1	1.0614 (2)	0.6700 (3)	0.63857 (5)	0.0180 (3)
C2	0.9798 (2)	0.7860 (3)	0.67597 (5)	0.0195 (3)
C3	1.0927 (2)	0.9893 (3)	0.69923 (5)	0.0195 (3)
C4	1.2888 (2)	1.0703 (3)	0.68471 (5)	0.0172 (3)
C5	1.3742 (2)	0.9581 (3)	0.64772 (5)	0.0216 (4)
C6	1.2599 (2)	0.7585 (3)	0.62471 (5)	0.0214 (4)
N4	1.41049 (19)	1.2853 (3)	0.70893 (4)	0.0190 (3)
O41	1.32987 (17)	1.3916 (2)	0.74050 (3)	0.0251 (3)
O42	1.58791 (17)	1.3487 (2)	0.69620 (3)	0.0266 (3)
C11	0.9388 (2)	0.4543 (3)	0.61428 (5)	0.0192 (3)
N11	0.99326 (19)	0.3625 (3)	0.57753 (4)	0.0212 (3)
C12	0.8611 (2)	0.1507 (3)	0.55614 (5)	0.0217 (4)
C13	0.7409 (2)	0.2517 (3)	0.51322 (5)	0.0203 (4)
C14	0.5605 (2)	0.4499 (3)	0.52148 (5)	0.0209 (4)
H2	0.8456	0.7255	0.6856	0.023*
H3	1.0365	1.0705	0.7245	0.023*
H5	1.5093	1.0180	0.6384	0.026*
H6	1.3162	0.6803	0.5992	0.026*
H11	0.8147	0.3819	0.6267	0.023*
H12A	0.7550	0.0867	0.5768	0.026*
H12B	0.9547	−0.0028	0.5493	0.026*
H13A	0.8457	0.3398	0.4947	0.024*
H13B	0.6780	0.0961	0.4963	0.024*
H14A	0.6234	0.6058	0.5383	0.025*
H14B	0.4560	0.3620	0.5401	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0193 (7)	0.0185 (8)	0.0158 (7)	−0.0004 (6)	−0.0016 (6)	0.0025 (6)
C2	0.0183 (7)	0.0213 (8)	0.0191 (7)	−0.0021 (6)	0.0023 (6)	0.0010 (6)
C3	0.0208 (8)	0.0208 (8)	0.0171 (7)	0.0006 (7)	0.0035 (6)	−0.0006 (6)
C4	0.0187 (7)	0.0161 (8)	0.0163 (7)	−0.0009 (6)	−0.0024 (6)	0.0016 (6)
C5	0.0175 (7)	0.0271 (9)	0.0204 (7)	−0.0032 (7)	0.0029 (6)	0.0013 (7)
C6	0.0221 (8)	0.0242 (8)	0.0183 (7)	0.0008 (7)	0.0046 (6)	−0.0022 (6)
N4	0.0197 (6)	0.0176 (7)	0.0193 (6)	−0.0005 (5)	−0.0001 (5)	0.0025 (5)
O41	0.0270 (6)	0.0239 (6)	0.0245 (6)	−0.0008 (5)	0.0031 (5)	−0.0064 (5)
O42	0.0227 (6)	0.0299 (7)	0.0276 (6)	−0.0100 (5)	0.0043 (5)	0.0002 (5)
C11	0.0197 (7)	0.0186 (8)	0.0193 (7)	−0.0018 (6)	0.0010 (6)	0.0021 (6)
N11	0.0217 (7)	0.0225 (7)	0.0191 (6)	−0.0023 (6)	−0.0012 (5)	−0.0026 (6)
C12	0.0238 (8)	0.0194 (8)	0.0222 (8)	−0.0005 (7)	0.0027 (6)	−0.0034 (7)
C13	0.0213 (8)	0.0213 (8)	0.0185 (7)	−0.0038 (7)	0.0023 (6)	−0.0041 (6)
C14	0.0226 (8)	0.0217 (9)	0.0184 (7)	−0.0036 (6)	0.0020 (6)	−0.0033 (6)

Geometric parameters (Å, º) top

C1—C2	1.394 (2)	N4—O42	1.2315 (15)
C1—C6	1.398 (2)	C11—N11	1.2663 (18)
C1—C11	1.476 (2)	C11—H11	0.95
C2—C3	1.389 (2)	N11—C12	1.4546 (19)
C2—H2	0.95	C12—C13	1.527 (2)
C3—C4	1.381 (2)	C12—H12A	0.99
C3—H3	0.95	C12—H12B	0.99
C4—C5	1.386 (2)	C13—C14	1.524 (2)
C4—N4	1.4698 (19)	C13—H13A	0.99
C5—C6	1.376 (2)	C13—H13B	0.99
C5—H5	0.95	C14—C14ⁱ	1.528 (3)
C6—H6	0.95	C14—H14A	0.99
N4—O41	1.2265 (15)	C14—H14B	0.99

C2—C1—C6	119.38 (14)	N11—C11—H11	118.8
C2—C1—C11	119.83 (13)	C1—C11—H11	118.8
C6—C1—C11	120.79 (13)	C11—N11—C12	118.07 (13)
C3—C2—C1	120.68 (14)	N11—C12—C13	110.98 (13)
C3—C2—H2	119.7	N11—C12—H12A	109.4
C1—C2—H2	119.7	C13—C12—H12A	109.4
C4—C3—C2	118.28 (13)	N11—C12—H12B	109.4
C4—C3—H3	120.9	C13—C12—H12B	109.4
C2—C3—H3	120.9	H12A—C12—H12B	108.0
C3—C4—C5	122.31 (14)	C14—C13—C12	113.04 (12)
C3—C4—N4	119.02 (13)	C14—C13—H13A	109.0
C5—C4—N4	118.66 (13)	C12—C13—H13A	109.0
C6—C5—C4	118.85 (14)	C14—C13—H13B	109.0
C6—C5—H5	120.6	C12—C13—H13B	109.0
C4—C5—H5	120.6	H13A—C13—H13B	107.8
C5—C6—C1	120.49 (14)	C13—C14—C14ⁱ	113.03 (15)
C5—C6—H6	119.8	C13—C14—H14A	109.0
C1—C6—H6	119.8	C14ⁱ—C14—H14A	109.0
O41—N4—O42	123.74 (13)	C13—C14—H14B	109.0
O41—N4—C4	118.37 (12)	C14ⁱ—C14—H14B	109.0
O42—N4—C4	117.89 (12)	H14A—C14—H14B	107.8
N11—C11—C1	122.31 (14)

C6—C1—C2—C3	0.5 (2)	C3—C4—N4—O41	−2.3 (2)
C11—C1—C2—C3	−179.95 (13)	C5—C4—N4—O41	176.99 (13)
C1—C2—C3—C4	−0.9 (2)	C3—C4—N4—O42	177.87 (13)
C2—C3—C4—C5	0.7 (2)	C5—C4—N4—O42	−2.8 (2)
C2—C3—C4—N4	179.98 (13)	C2—C1—C11—N11	172.20 (15)
C3—C4—C5—C6	−0.1 (2)	C6—C1—C11—N11	−8.3 (2)
N4—C4—C5—C6	−179.41 (13)	C1—C11—N11—C12	−179.72 (12)
C4—C5—C6—C1	−0.3 (2)	C11—N11—C12—C13	111.90 (15)
C2—C1—C6—C5	0.1 (2)	N11—C12—C13—C14	−70.53 (15)
C11—C1—C6—C5	−179.45 (14)	C12—C13—C14—C14ⁱ	−179.76 (15)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O42ⁱⁱ	0.95	2.50	3.3491 (18)	149

Symmetry code: (ii) x−1, y−1, z.

Experimental details

	(III)	(IV)
Crystal data
Chemical formula	C₁₈H₁₈N₄O₄	C₂₀H₂₂N₄O₄
M_r	354.36	382.42
Crystal system, space group	Triclinic, P1	Monoclinic, P2₁/c
Temperature (K)	120	120
a, b, c (Å)	7.1162 (4), 7.1895 (2), 9.1695 (4)	6.1908 (3), 4.9761 (2), 30.1095 (15)
α, β, γ (°)	83.210 (3), 78.920 (2), 64.808 (3)	90, 94.331 (3), 90
V (Å³)	416.25 (3)	924.91 (7)
Z	1	2
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.10	0.10
Crystal size (mm)	0.46 × 0.34 × 0.13	0.44 × 0.30 × 0.12

Data collection
Diffractometer	Nonius KappaCCD area-detector	Nonius KappaCCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.944, 0.987	0.952, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	8689, 1895, 1589	7409, 2083, 1516
R_int	0.028	0.041
(sin θ/λ)_max (Å⁻¹)	0.651	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.114, 1.05	0.045, 0.113, 1.06
No. of reflections	1893	2083
No. of parameters	118	127
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.34	0.19, −0.30

Computer programs: COLLECT (Nonius, 1998), DENZO (Otwinowski & Minor, 1997) and COLLECT, DENZO and COLLECT, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected torsion angles (°) for compounds (II)–(IV) top

Parameter	(II)	(III)	(IV)
C3-C4-N4-O41	-5.86 (15)	0.96 (15)	-2.3 (2)
C2-C1-C11-N11	177.91 (9)	-171.77 (10)	172.20 (15)
C1-C11-N11-C12	-176.58 (8)	-179.54 (9)	-179.72 (12)
C11-N11-C12-C12ⁱ	118.31 (13)
C11-N11-C12-C13		111.42 (11)	111.90 (15)
N11-C12-C13-C13ⁱ		-65.67 (15)
N11-C12-C13-C14			-70.53 (15)
C12-C13-C14-C14ⁱ			-179.76 (15)

Symmetry code: (i) 1 - x, 1 - y, 1 - z. Data for compound (II) from Bomfim et al. (2005).

Hydrogen-bond geometry (Å, °) for compounds (III) and (IV) top

Compound	D-H···A	D-H	H···A	D···A	D-H···A
(III)	C11-H11···O42ⁱ	0.95	2.60	3.502 (2)	159
(IV)	C2-H2···O42ⁱⁱ	0.95	2.50	3.349 (2)	149

Symmetry codes: (i) x, y, 1 + z; (ii) -1 + x, -1 + y, z.

Acknowledgements

The X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton; the authors thank the staff for all their help and advice. JLW thanks CNPq and FAPERJ for financial support.

References

Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320–329. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
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ISSN: 2053-2296

Volume 62| Part 1| January 2006| Pages o1-o4

doi:10.1107/S0108270105035766

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Three-dimensional supramolecular structures in (E,E)-N,N′-bis­­(4-nitro­benzyl­­idene)butane-1,4-di­amine and (E,E)-N,N′-bis­­(4-nitro­benzyl­­idene)­hexane-1,6-di­amine

Comment

Experimental

Compound (III)

Crystal data

Data collection

Refinement

Compound (IV)

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Three-dimensional supramolecular structures in (E,E)-N,N′-bis(4-nitrobenzylidene)butane-1,4-diamine and (E,E)-N,N′-bis(4-nitrobenzylidene)hexane-1,6-diamine