Bis(dimethyl-ammonium) 2,2'-(1,3,6,8-tetra-oxo-2,7-diaza-pyrene-2,7-di-yl)diacetate.

The asymmetric unit of title compound, 2C(2)H(8)N(+)·C(18)H(8)N(2)O(8) (2-), comprises one crystallographically independent dimethyl-ammonium cation and half of a 2,2'-(1,3,6,8-tetra-oxo-2,7-diaza-pyrene-2,7-di-yl)diacetate dianion. The anion lies on an inversion centre and the two carboxyl-ate groups are in trans positions based on the naphthaleneteracarb-oxy-lic diimide group. The crystal packing is stabilized by N-H⋯O hydrogen bonds between cations and anions, as well as by π-π inter-actions between the naph-thaleneteracarb-oxy-lic 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+·C18H8N2O8 2−

M = 472.45

Triclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.114

S = 1.04

2298 reflections

202 parameters

All H-atom parameters refined

Δρmax = 0.50 e Å−3

Δρmin = −0.23 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811026511/om2439sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811026511/om2439Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

2C2H8N+·C18H8N2O82−	Z = 1
Mr = 472.45	F(000) = 248
Triclinic, P1	Dx = 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

Rigaku Saturn724+ diffractometer	2298 independent reflections
Radiation source: fine-focus sealed tube	1969 reflections with I > 2σ(I)
Confocal	Rint = 0.018
Detector resolution: 28.57 pixels mm-1	θmax = 27.5°, θmin = 2.9°
ω scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008)	k = −11→11
Tmin = 0.976, Tmax = 0.983	l = −16→16
4207 measured reflections

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(Fo2) + (0.069P)2 + 0.126P] where P = (Fo2 + 2Fc2)/3
2298 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) ; (ii) .