Bis(dimethyl­ammonium) 2,2′-(1,3,6,8-tetra­oxo-2,7-diaza­pyrene-2,7-di­yl)diacetate

Xu, L.-P.; Zhao, W.-N.; Han, L.

doi:10.1107/S1600536811026511

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1971

doi:10.1107/S1600536811026511

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Bis(dimethylammonium) 2,2′-(1,3,6,8-tetraoxo-2,7-diazapyrene-2,7-diyl)diacetate

Lan-Ping Xu,^a Wen-Na Zhao ^b and Lei Han ^a ^*

^aState Key Laboratory Base of Novel Functional Materials and Preparation Science, Faculty of Materials Science & Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, People's Republic of China, and ^bKey Laboratory for Molecular Design and Nutrition Engineering of Ningbo, Ningbo Institute of Technology, Zhejiang University, Ningbo, Zhejiang 315100, People's Republic of China
^*Correspondence e-mail: hanlei@nbu.edu.cn

(Received 12 June 2011; accepted 4 July 2011; online 9 July 2011)

The asymmetric unit of title compound, 2C₂H₈N⁺·C₁₈H₈N₂O₈²⁻, comprises one crystallographically independent dimethylammonium cation and half of a 2,2′-(1,3,6,8-tetraoxo-2,7-diazapyrene-2,7-diyl)diacetate dianion. The anion lies on an inversion centre and the two carboxylate groups are in trans positions based on the naphthaleneteracarboxylic diimide group. The crystal packing is stabilized by N—H⋯O hydrogen bonds between cations and anions, as well as by π–π interactions between the naphthaleneteracarboxylic diimide groups [centroid–centroid distance = 4.812 (3) Å].

Related literature

For organic supramolecular solids, see: Pantos et al. (2007 ). For the prediction of organic crystal structures, see: Pigge (2011 ).

Experimental

Crystal data

2C₂H₈N⁺·C₁₈H₈N₂O₈²⁻
M_r = 472.45
Triclinic, $[P \overline 1]$
a = 4.812 (3) Å
b = 8.901 (5) Å
c = 12.640 (7) Å
α = 92.361 (9)°
β = 91.512 (6)°
γ = 99.789 (9)°
V = 532.7 (5) Å³
Z = 1
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.2 × 0.2 × 0.2 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008 ) T_min = 0.976, T_max = 0.983
4207 measured reflections
2298 independent reflections
1969 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.114
S = 1.04
2298 reflections
202 parameters
All H-atom parameters refined
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H5⋯O2	1.006 (19)	1.76 (2)	2.7358 (18)	163.5 (16)
N2—H6⋯O1ⁱ	0.94 (2)	2.13 (2)	2.8419 (18)	131.8 (17)
N2—H6⋯O1ⁱⁱ	0.94 (2)	2.13 (2)	2.935 (2)	142.9 (17)
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+1, -z.

Data collection: CrystalClear (Rigaku/MSC, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811026511/om2439sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026511/om2439Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026511/om2439Isup3.cml

checkCIF report

Comment top

The assembly of functionalised organic molecules in the solid state has attracted much attention in crystal engineering and materials science (Pantos et al., 2007). The prediction of organic crystal structures is a central aim of the development of successful synthetic strategies. In general, precise control over solid state assembly processes will facilitate the synthesis of complex functional materials imbued with desirable optical, electronic, magnetic properties starting from carefully chosen yet relatively simple molecular precursors (Pigge, 2011). We are interested in utilizing acid-functionalized naphthalaleneteracarboxylic diimide derivative as starting materials in crystal engineering approaches to a range of functional organic materials. Herein we report an unexpected organic salt compound 2(C₂H₈N).(C₁₈H₈N₂O₈), (I), which is prepared under solvothermal reaction from 1,4,5,8-naphthalaleneteracarboxylic diimide-N,N'-diacetic acid and 4,4'-bipyridyl in DMF. The dimethylammonium cations come from in situ hydrolysis of DMF molecules.

The asymmetric unit of the title compound comprises one crystallographically independent dimethylammonium cation and half of 1,4,5,8-naphthalaleneteracarboxylic diimide-N,N'-diacetate anion. As shown in Figure 1, the anion lies on an inversion centre, and the two carboxylate groups of the anion are in trans positions based on naphthalaleneteracarboxylic diimide plane. There are strong N—H···O hydrogen bonds between dimethylammonium cations and the carboxylate groups of anions, which are listed in Table 1. The overall hydrogen bonding interaction makes a 12-atom ring and a 4-atom ring, as shown in Figure 2. On the other hand, because of the large π–conjugated skeleton in the naphthalaleneteracarboxylic diimide moiety, the strong intermolecular π···π interactions are formed with the perpendicular distance between planes of 3.32 Å. Therefore, the crystal packing of I is stabilized both by N—H···O hydrogen bonds and π···π interactions.

Related literature top

For organic supramolecular solids, see: Pantos et al. (2007). For the prediction of organic crystal structures, see: Pigge (2011).

Experimental top

A mixture of 1,4,5,8-naphthalaleneteracarboxylic diimide-N,N'-diacetic acid (38.32 mg), 4,4'-bipyridyl (31.24 mg) in DMF (3 ml) was sealed in a 25 ml Teflon-lined stainless steel reactor and heated at 373 K for 72 h. Single crystals of the title compound were obtained after cooling the solution to room temperature, and washed with DMF. The yield is calculated 60%.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2008); cell refinement: CrystalClear (Rigaku/MSC, 2008); data reduction: CrystalClear (Rigaku/MSC, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure with displacement ellipsoids drawn at the 30% probability level and H atoms shown as small spheres of arbitrary radii.
	Fig. 2. View of N—H···O hydrogen bonds and π···π interactions.

Bis(dimethylammonium) 2,2'-(1,3,6,8-tetraoxo-2,7-diazapyrene-2,7-diyl)diacetate top

Crystal data top

2C₂H₈N⁺·C₁₈H₈N₂O₈²⁻	Z = 1
M_r = 472.45	F(000) = 248
Triclinic, P1	D_x = 1.473 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.812 (3) Å	Cell parameters from 1620 reflections
b = 8.901 (5) Å	θ = 2.3–27.5°
c = 12.640 (7) Å	µ = 0.11 mm⁻¹
α = 92.361 (9)°	T = 298 K
β = 91.512 (6)°	Prism, colorless
γ = 99.789 (9)°	0.2 × 0.2 × 0.2 mm
V = 532.7 (5) Å³

Data collection top

Rigaku Saturn724+ diffractometer	2298 independent reflections
Radiation source: fine-focus sealed tube	1969 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.018
Detector resolution: 28.57 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
ω scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008)	k = −11→11
T_min = 0.976, T_max = 0.983	l = −16→16
4207 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	All H-atom parameters refined
S = 1.04	w = 1/[σ²(F_o²) + (0.069P)² + 0.126P] where P = (F_o² + 2F_c²)/3
2298 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

2C₂H₈N⁺·C₁₈H₈N₂O₈²⁻	γ = 99.789 (9)°
M_r = 472.45	V = 532.7 (5) Å³
Triclinic, P1	Z = 1
a = 4.812 (3) Å	Mo Kα radiation
b = 8.901 (5) Å	µ = 0.11 mm⁻¹
c = 12.640 (7) Å	T = 298 K
α = 92.361 (9)°	0.2 × 0.2 × 0.2 mm
β = 91.512 (6)°

Data collection top

Rigaku Saturn724+ diffractometer	2298 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008)	1969 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.983	R_int = 0.018
4207 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.114	All H-atom parameters refined
S = 1.04	Δρ_max = 0.50 e Å⁻³
2298 reflections	Δρ_min = −0.23 e Å⁻³
202 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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

	x	y	z	U_iso*/U_eq
O1	0.4577 (2)	0.61234 (11)	0.08100 (7)	0.0248 (3)
O2	0.1971 (2)	0.79037 (11)	0.12376 (7)	0.0252 (3)
O3	0.63240 (19)	1.06673 (10)	0.27584 (7)	0.0179 (2)
O4	−0.2062 (2)	1.40383 (10)	0.63370 (7)	0.0207 (2)
N1	0.4256 (2)	0.83103 (11)	0.32377 (7)	0.0136 (2)
N2	−0.0973 (3)	0.68928 (13)	−0.06090 (8)	0.0204 (3)
H5	0.030 (4)	0.711 (2)	0.0042 (15)	0.038 (5)*
H6	−0.248 (5)	0.615 (2)	−0.0421 (16)	0.046 (6)*
C1	0.3916 (3)	0.71603 (14)	0.14037 (9)	0.0180 (3)
C2	0.5758 (3)	0.75754 (15)	0.24241 (9)	0.0160 (3)
H1	0.736 (4)	0.827 (2)	0.2294 (13)	0.029 (4)*
H2	0.634 (3)	0.6701 (19)	0.2725 (12)	0.022 (4)*
C3	0.4599 (2)	0.99015 (14)	0.32887 (9)	0.0136 (3)
C4	0.2780 (3)	1.06025 (13)	0.40288 (9)	0.0130 (3)
C5	0.2994 (3)	1.21692 (14)	0.41186 (9)	0.0151 (3)
H3	0.429 (4)	1.2802 (18)	0.3699 (13)	0.023 (4)*
C6	0.1307 (3)	1.28406 (14)	0.48269 (9)	0.0159 (3)
H4	0.150 (3)	1.3937 (19)	0.4859 (12)	0.023 (4)*
C7	−0.0576 (3)	1.19431 (13)	0.54381 (9)	0.0131 (3)
C8	−0.2309 (3)	1.26571 (14)	0.62007 (9)	0.0147 (3)
C9	0.0849 (2)	0.96643 (13)	0.46443 (8)	0.0121 (3)
C10	0.0565 (3)	0.62531 (17)	−0.14666 (11)	0.0257 (3)
H7	−0.077 (4)	0.587 (2)	−0.2030 (15)	0.034 (5)*
H8	0.156 (4)	0.544 (2)	−0.1197 (13)	0.030 (4)*
H9	0.190 (4)	0.711 (2)	−0.1699 (15)	0.042 (5)*
C11	−0.1980 (4)	0.83071 (19)	−0.09026 (12)	0.0301 (3)
H12	−0.038 (4)	0.910 (2)	−0.1036 (14)	0.033 (5)*
H11	−0.315 (4)	0.804 (2)	−0.1546 (17)	0.046 (5)*
H10	−0.309 (4)	0.866 (2)	−0.0336 (16)	0.042 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0250 (5)	0.0264 (5)	0.0221 (5)	0.0038 (4)	0.0058 (4)	−0.0082 (4)
O2	0.0258 (5)	0.0310 (6)	0.0201 (5)	0.0102 (4)	−0.0030 (4)	−0.0031 (4)
O3	0.0183 (5)	0.0194 (5)	0.0164 (4)	0.0034 (4)	0.0055 (3)	0.0028 (3)
O4	0.0297 (5)	0.0129 (4)	0.0205 (4)	0.0063 (4)	0.0062 (4)	−0.0011 (3)
N1	0.0163 (5)	0.0152 (5)	0.0102 (5)	0.0054 (4)	0.0016 (4)	−0.0011 (4)
N2	0.0210 (6)	0.0233 (6)	0.0165 (5)	0.0028 (5)	−0.0013 (4)	0.0024 (4)
C1	0.0181 (6)	0.0202 (6)	0.0150 (6)	0.0012 (5)	0.0045 (5)	−0.0003 (4)
C2	0.0177 (6)	0.0174 (6)	0.0144 (5)	0.0071 (5)	0.0042 (5)	−0.0015 (4)
C3	0.0144 (6)	0.0165 (6)	0.0103 (5)	0.0043 (5)	−0.0016 (4)	0.0008 (4)
C4	0.0144 (6)	0.0155 (6)	0.0098 (5)	0.0044 (5)	−0.0002 (4)	0.0005 (4)
C5	0.0161 (6)	0.0153 (6)	0.0137 (5)	0.0018 (5)	0.0018 (4)	0.0028 (4)
C6	0.0202 (6)	0.0120 (6)	0.0158 (6)	0.0039 (5)	0.0004 (5)	0.0004 (4)
C7	0.0153 (6)	0.0139 (6)	0.0108 (5)	0.0045 (5)	−0.0005 (4)	0.0000 (4)
C8	0.0173 (6)	0.0153 (6)	0.0122 (5)	0.0052 (5)	−0.0006 (4)	0.0008 (4)
C9	0.0134 (6)	0.0130 (6)	0.0101 (5)	0.0033 (5)	−0.0015 (4)	0.0005 (4)
C10	0.0313 (8)	0.0248 (7)	0.0201 (6)	0.0023 (7)	0.0041 (6)	0.0003 (5)
C11	0.0319 (8)	0.0319 (8)	0.0293 (7)	0.0117 (7)	0.0000 (6)	0.0078 (6)

Geometric parameters (Å, º) top

O1—C1	1.2535 (16)	C4—C9	1.4119 (18)
O2—C1	1.2529 (17)	C5—C6	1.4061 (17)
O3—C3	1.2156 (15)	C5—H3	0.954 (18)
O4—C8	1.2195 (16)	C6—C7	1.3775 (19)
N1—C8ⁱ	1.3909 (17)	C6—H4	0.963 (16)
N1—C3	1.3963 (17)	C7—C9ⁱ	1.4135 (18)
N1—C2	1.4669 (15)	C7—C8	1.4834 (16)
N2—C10	1.4771 (18)	C8—N1ⁱ	1.3909 (17)
N2—C11	1.4811 (19)	C9—C9ⁱ	1.412 (2)
N2—H5	1.006 (19)	C9—C7ⁱ	1.4135 (18)
N2—H6	0.94 (2)	C10—H7	0.958 (19)
C1—C2	1.5410 (18)	C10—H8	0.999 (18)
C2—H1	0.924 (18)	C10—H9	0.97 (2)
C2—H2	0.961 (16)	C11—H12	0.977 (19)
C3—C4	1.4872 (16)	C11—H11	0.98 (2)
C4—C5	1.3804 (19)	C11—H10	0.98 (2)

C8ⁱ—N1—C3	125.18 (10)	C6—C5—H3	119.6 (9)
C8ⁱ—N1—C2	116.13 (10)	C7—C6—C5	120.39 (12)
C3—N1—C2	118.08 (10)	C7—C6—H4	121.9 (9)
C10—N2—C11	112.51 (11)	C5—C6—H4	117.7 (9)
C10—N2—H5	108.9 (11)	C6—C7—C9ⁱ	120.41 (11)
C11—N2—H5	109.7 (10)	C6—C7—C8	120.22 (11)
C10—N2—H6	109.1 (13)	C9ⁱ—C7—C8	119.36 (11)
C11—N2—H6	110.9 (12)	O4—C8—N1ⁱ	120.54 (11)
H5—N2—H6	105.5 (16)	O4—C8—C7	121.96 (12)
O2—C1—O1	126.66 (12)	N1ⁱ—C8—C7	117.50 (11)
O2—C1—C2	117.51 (11)	C4—C9—C9ⁱ	119.72 (14)
O1—C1—C2	115.81 (11)	C4—C9—C7ⁱ	121.20 (11)
N1—C2—C1	111.40 (10)	C9ⁱ—C9—C7ⁱ	119.08 (14)
N1—C2—H1	106.2 (10)	N2—C10—H7	107.9 (11)
C1—C2—H1	110.7 (11)	N2—C10—H8	110.6 (10)
N1—C2—H2	107.6 (10)	H7—C10—H8	111.8 (14)
C1—C2—H2	112.6 (10)	N2—C10—H9	105.1 (11)
H1—C2—H2	108.1 (14)	H7—C10—H9	110.1 (15)
O3—C3—N1	121.18 (11)	H8—C10—H9	111.0 (14)
O3—C3—C4	122.08 (11)	N2—C11—H12	110.3 (11)
N1—C3—C4	116.74 (11)	N2—C11—H11	106.1 (12)
C5—C4—C9	120.10 (11)	H12—C11—H11	110.3 (15)
C5—C4—C3	119.99 (11)	N2—C11—H10	110.0 (11)
C9—C4—C3	119.92 (11)	H12—C11—H10	109.6 (15)
C4—C5—C6	120.29 (12)	H11—C11—H10	110.4 (16)
C4—C5—H3	120.1 (9)

C8ⁱ—N1—C2—C1	79.11 (13)	C3—C4—C5—C6	−179.17 (10)
C3—N1—C2—C1	−92.46 (13)	C4—C5—C6—C7	0.01 (19)
O2—C1—C2—N1	23.91 (16)	C5—C6—C7—C9ⁱ	−0.44 (19)
O1—C1—C2—N1	−157.63 (11)	C5—C6—C7—C8	178.71 (10)
C8ⁱ—N1—C3—O3	−178.82 (10)	C6—C7—C8—O4	−2.53 (19)
C2—N1—C3—O3	−8.08 (17)	C9ⁱ—C7—C8—O4	176.63 (11)
C8ⁱ—N1—C3—C4	1.85 (17)	C6—C7—C8—N1ⁱ	177.33 (10)
C2—N1—C3—C4	172.59 (9)	C9ⁱ—C7—C8—N1ⁱ	−3.50 (17)
O3—C3—C4—C5	0.90 (18)	C5—C4—C9—C9ⁱ	−0.3 (2)
N1—C3—C4—C5	−179.78 (10)	C3—C4—C9—C9ⁱ	179.21 (12)
O3—C3—C4—C9	−178.65 (10)	C5—C4—C9—C7ⁱ	179.58 (10)
N1—C3—C4—C9	0.67 (17)	C3—C4—C9—C7ⁱ	−0.87 (18)
C9—C4—C5—C6	0.38 (19)

Symmetry code: (i) −x, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H5···O2	1.006 (19)	1.76 (2)	2.7358 (18)	163.5 (16)
N2—H6···O1ⁱⁱ	0.94 (2)	2.13 (2)	2.8419 (18)	131.8 (17)
N2—H6···O1ⁱⁱⁱ	0.94 (2)	2.13 (2)	2.935 (2)	142.9 (17)

Symmetry codes: (ii) x−1, y, z; (iii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	2C₂H₈N⁺·C₁₈H₈N₂O₈²⁻
M_r	472.45
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	4.812 (3), 8.901 (5), 12.640 (7)
α, β, γ (°)	92.361 (9), 91.512 (6), 99.789 (9)
V (Å³)	532.7 (5)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.2 × 0.2 × 0.2

Data collection
Diffractometer	Rigaku Saturn724+ diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2008)
T_min, T_max	0.976, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	4207, 2298, 1969
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.114, 1.04
No. of reflections	2298
No. of parameters	202
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.23

Computer programs: CrystalClear (Rigaku/MSC, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H5···O2	1.006 (19)	1.76 (2)	2.7358 (18)	163.5 (16)
N2—H6···O1ⁱ	0.94 (2)	2.13 (2)	2.8419 (18)	131.8 (17)
N2—H6···O1ⁱⁱ	0.94 (2)	2.13 (2)	2.935 (2)	142.9 (17)

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (21071087), the Natural Science Foundation of Ningbo Municipality (2009A610129) and the K. C. Wong Magna Fund in Ningbo University.

References

Pantos, G. D., Wietor, J.-L. & Sanders, J. K. M. (2007). Angew. Chem. Int. Ed. 46, 2238–2240. CAS Google Scholar
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