The charge-transfer complex 1-amino­anthraquinone–7,7′,8,8′-tetra­cyano­quinodimethane (1/1)

Oliveira, A.B. de; Beck, J.; Daniels, J.; Santos, J.N.; Feitosa, B.R.S.

doi:10.1107/S1600536813002195

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o301

doi:10.1107/S1600536813002195

Open

access

The charge-transfer complex 1-aminoanthraquinone–7,7′,8,8′-tetracyanoquinodimethane (1/1)

Adriano Bof de Oliveira,^a ^* Johannes Beck,^b Jörg Daniels,^b Jaciara Nascimento Santos ^a and Bárbara Regina Santos Feitosa ^a

^aDepartamento de Química, Universidade Federal de Sergipe, Av. Marechal Rondon s/n, Campus, 49100-000 São Cristóvão-SE, Brazil, and ^bInstitut für Anorganische Chemie, Universität Bonn, Gerhard-Domagk-Strasse 1, D-53121 Bonn, Germany
^*Correspondence e-mail: adriano@daad-alumni.de

(Received 21 January 2013; accepted 22 January 2013; online 26 January 2013)

The reaction of 1-aminoanthraquinone with 7,7′,8,8′-tetracyanoquinodimethane yielded the title charge-transfer complex, C₁₄H₉NO₂·C₁₂H₄N₄. The molecules have maximum deviations from the mean planes through the non-H atoms of 0.0769 (14) Å for an oxo O atom and 0.1175 (17) Å for a cyano N atom, respectively. The dihedral angle between the two planes is 3.55 (3)°. In the crystal, molecules are stacked into columns along the a-axis direction. Pairs of N—H⋯N and N—H⋯O interactions connect the molecules perpendicular to the stacking direction. Additionally, an intramolecular N—H⋯O hydrogen-bond interaction is observed for 1-aminoanthraquinone.

Related literature

For a revised structure of 1-aminoanthraquinone, see: Milić et al. (2012 ). For charge-transfer complexes of aromatic derivatives with 7,7′,8,8′-tetracyanoquinodimethane, see: Press et al. (2012 ). For the conductivity of organic salts, see: Jérome (2004 ). For the coordination chemistry of 7,7′,8,8′-tetracyanoquinodimethane, see: Kaim & Moscherosch (1994 ).

Experimental

Crystal data

C₁₂H₄N₄·C₁₄H₉NO₂
M_r = 427.41
Monoclinic, P 2₁ /c
a = 7.4916 (2) Å
b = 9.4321 (3) Å
c = 28.8093 (8) Å
β = 95.8785 (15)°
V = 2025.00 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.29 × 0.05 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: analytical (Alcock, 1970 ) T_min = 0.974, T_max = 0.996
19055 measured reflections
3972 independent reflections
2324 reflections with I > 2σ(I)
R_int = 0.147

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.135
S = 1.01
3972 reflections
350 parameters
All H-atom parameters refined
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O2	0.93 (3)	1.96 (3)	2.654 (3)	130 (2)
N1—HN1⋯O2ⁱ	0.93 (3)	2.25 (3)	3.019 (3)	139 (2)
N1—HN2⋯N3ⁱⁱ	1.02 (3)	2.22 (3)	3.229 (3)	171 (2)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y, -z.

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813002195/bt6884sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813002195/bt6884Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813002195/bt6884Isup3.cml

checkCIF report

Comment top

Charge transfer compounds with 7,7',8,8'-tetracyanoquinodimethane (TCNQ) as the acceptor component have a wide range of properties, such as paramagnetism, cooperative magnetism or electrical conductivity. TCNQ can be easily reduced to the anionic form. The single unpaired electron occupies the lowest unoccupied molecular orbitals, that are mainly located at the terminal dicyanomethylene fragments. When the TCNQ units stack and the intermolecular spacings are shorter than the van der Waals distances for carbon, the π orbitals will contribute to electrical conductivity (Jérome, 2004). Additionally, TCNQ compounds have a very interesting coordination chemistry (Kaim & Moscherosch, 1994). As part of our study of charge transfer complex structures, we report herein the synthesis and the crystal structure of a new TCNQ-acceptor compound with 1-aminoanthraquinone-donor (Milić et al., 2012).

In the title compound, the molecular structure unit matches the asymmetric unit (Fig. 1). Both molecules show only a slight deviation from planarity. The maximal deviation from the least squares plane through all non-hydrogen atoms for the 1-aminoanthraquinone and the 7,7',8,8'-tetracyanoquinodimethane molecule amount to 0.0769 (14) Å for O2 and 0.1175 (17) Å for N5, respectively, and the dihedral angle between the two planes is 3.55 (03)°. The bond angles suggest sp² hybridization for the C atoms and explain the planarity of both molecules. The structure is built from mixed stacks of donor and acceptor molecules. The stacks run the crystallographic a axis (Fig. 3). The mean distance between the molecules within the stack amounts to one half of the length of the a axis, i.e. 3.7456 (2) Å. This explains the low electrical conductivity of the compound. Above room temperature, however, a detectable electrical conductivity was observed, which reaches 4.4 × 10^-8 S/cm at 370 K. In the temperature range between 2 K and 300 K the title compound turned out as diamagnetic. The bond lengths within the dicyanomethylene groups suggest that the TCNQ units are neutral, comparing with crystal and infrared literature data (Kaim & Moscherosch, 1994). However, a small charge transfer is apparently present, since the electrical resistivity falls with increasing temperature indicating semiconducting characteristics. From the resistivity data, an Arrhenius development –ln(1/R) versus. 1/T gives a mainly linear behaviour, from which a small barrier for the thermally activated transport of 1.25 eV can be derived, according with dark brown colour of the crystals.

The crystal packing is stabilized by intermolecular hydrogen interactions. The molecules are connected by pairs of centrosymmetrical N—H···O and N—H···N hydrogen interactions, building dimers (Table 1; N1—HN1···O2ⁱ_; N1—HN2···N3ⁱⁱ and Fig. 2). Additionally, an intramolecular N—H···O hydrogen interaction is observed for the 1-aminoanthraquinone (Table 1; N1—HN1···O2 and Fig. 2).

Related literature top

For a revised structure of 1-aminoanthraquinone, see: Milić et al. (2012). For charge-transfer complexes of aromatic derivatives with 7,7',8,8'-tetracyanoquinodimethane, see: Press et al. (2012). For the conductivity of organic salts, see: Jérome (2004). For the coordination chemistry of 7,7',8,8'-tetracyanoquinodimethane, see: Kaim & Moscherosch (1994).

Experimental top

Starting materials were commercially available and were used without further purification. 1-Aminoanthraquinone and 7,7',8,8'-tetracyanoquinodimethane were dissolved in CH₂Cl₂ separately at room temperature and equimolar concentrations. The solutions were combined and maintained for 4 h under continuous stirring. Dark brown crystals, suitable for X-ray analysis, were obtained by the slow evaporation of the solvent. Elemental analysis: Calc. 73.1 C, 3.1 H, 16.4 N; found 72.8 C, 3.4 H, 16.6 N. The melting point was determined by differential scanning calorimetry to 520 K. Exothermic decomposition occurs at 555 K.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. : The molecular structure of the title compound with labelling and displacement ellipsoids drawn at the 40% probability level.
	Fig. 2. : Crystal structure of the title compound showing the dimeric arrangement. Intermolecular and Intramolecular hydrogen interactions are indicated as dashed lines. Symmetry codes: (i) -x + 1, -y + 1, -z; (ii) -x + 1, -y, -z; (iii) x, 1 + y, z.
	Fig. 3. : Crystal structure of the title compound showing the mixed stacks of donor and acceptor molecules. The stacks run the crystallographic a axis. The graphical representation is simplified for clarity.

1-Aminoanthraquinone–2-[4-(dicyanomethylidene)cyclohexa-2,5-dien-1-ylidene]propanedinitrile (1/1) top

Crystal data top

C₁₂H₄N₄·C₁₄H₉NO₂	F(000) = 880
M_r = 427.41	D_x = 1.402 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14532 reflections
a = 7.4916 (2) Å	θ = 2.9–27.5°
b = 9.4321 (3) Å	µ = 0.09 mm⁻¹
c = 28.8093 (8) Å	T = 293 K
β = 95.8785 (15)°	Needle, dark brown
V = 2025.00 (10) Å³	0.29 × 0.05 × 0.04 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	3972 independent reflections
Radiation source: fine-focus sealed tube	2324 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.147
Detector resolution: 9 pixels mm^-1	θ_max = 26.0°, θ_min = 3.0°
CCD rotation images, thick slices scans	h = −9→9
Absorption correction: analytical (Alcock, 1970)	k = −11→11
T_min = 0.974, T_max = 0.996	l = −32→35
19055 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	All H-atom parameters refined
S = 1.01	w = 1/[σ²(F_o²) + (0.0558P)² + 0.1436P] where P = (F_o² + 2F_c²)/3
3972 reflections	(Δ/σ)_max < 0.001
350 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₂H₄N₄·C₁₄H₉NO₂	V = 2025.00 (10) Å³
M_r = 427.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4916 (2) Å	µ = 0.09 mm⁻¹
b = 9.4321 (3) Å	T = 293 K
c = 28.8093 (8) Å	0.29 × 0.05 × 0.04 mm
β = 95.8785 (15)°

Data collection top

Nonius KappaCCD diffractometer	3972 independent reflections
Absorption correction: analytical (Alcock, 1970)	2324 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.996	R_int = 0.147
19055 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.135	All H-atom parameters refined
S = 1.01	Δρ_max = 0.16 e Å⁻³
3972 reflections	Δρ_min = −0.16 e Å⁻³
350 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
N1	0.6301 (3)	0.2662 (3)	0.00915 (7)	0.0621 (6)
HN1	0.586 (3)	0.358 (3)	0.0048 (9)	0.086 (9)*
HN2	0.625 (3)	0.195 (3)	−0.0176 (11)	0.110 (10)*
N2	0.0775 (3)	0.2756 (2)	−0.02511 (7)	0.0705 (6)
N3	0.3548 (3)	−0.0224 (2)	0.06905 (7)	0.0707 (6)
N4	0.4265 (3)	0.6007 (2)	0.28057 (7)	0.0688 (6)
N5	0.1954 (3)	0.9047 (2)	0.17933 (8)	0.0739 (6)
O1	0.9414 (2)	0.33407 (19)	0.20941 (6)	0.0763 (5)
O2	0.58619 (19)	0.51563 (15)	0.04905 (5)	0.0586 (4)
C1	0.7206 (2)	0.2324 (2)	0.05065 (7)	0.0438 (5)
C2	0.7953 (3)	0.0950 (2)	0.05632 (8)	0.0513 (6)
H2	0.776 (3)	0.028 (2)	0.0292 (8)	0.070 (7)*
C3	0.8834 (3)	0.0533 (3)	0.09792 (8)	0.0525 (6)
H3	0.936 (3)	−0.040 (3)	0.1011 (8)	0.066 (7)*
C4	0.9037 (3)	0.1446 (2)	0.13595 (8)	0.0485 (6)
H4	0.971 (3)	0.122 (2)	0.1661 (9)	0.069 (7)*
C5	0.8342 (2)	0.2799 (2)	0.13162 (7)	0.0407 (5)
C6	0.7425 (2)	0.3273 (2)	0.08894 (7)	0.0376 (5)
C7	0.8617 (2)	0.3753 (2)	0.17276 (7)	0.0473 (5)
C8	0.6729 (2)	0.4722 (2)	0.08494 (7)	0.0397 (5)
C9	0.7950 (2)	0.5229 (2)	0.16781 (7)	0.0413 (5)
C10	0.8227 (3)	0.6157 (3)	0.20549 (8)	0.0524 (6)
H10	0.895 (2)	0.5807 (18)	0.2367 (7)	0.039 (5)*
C11	0.7634 (3)	0.7541 (3)	0.20053 (9)	0.0574 (6)
H11	0.785 (3)	0.822 (2)	0.2272 (9)	0.072 (7)*
C12	0.6755 (3)	0.8007 (3)	0.15876 (9)	0.0536 (6)
H12	0.631 (3)	0.900 (2)	0.1552 (7)	0.061 (6)*
C13	0.6477 (3)	0.7089 (2)	0.12139 (8)	0.0486 (5)
H13	0.591 (3)	0.740 (2)	0.0917 (8)	0.052 (6)*
C14	0.7067 (2)	0.5693 (2)	0.12546 (7)	0.0393 (5)
C15	0.2500 (2)	0.3339 (2)	0.09187 (7)	0.0412 (5)
C16	0.3302 (3)	0.3018 (2)	0.13811 (7)	0.0443 (5)
C17	0.3431 (3)	0.4023 (2)	0.17152 (8)	0.0429 (5)
C18	0.2788 (2)	0.5444 (2)	0.16208 (7)	0.0402 (5)
C19	0.1987 (3)	0.5751 (2)	0.11561 (7)	0.0461 (5)
C20	0.1842 (3)	0.4753 (2)	0.08236 (8)	0.0472 (5)
C21	0.2352 (2)	0.2327 (2)	0.05729 (7)	0.0450 (5)
C22	0.1486 (3)	0.2588 (2)	0.01153 (8)	0.0507 (6)
C23	0.3026 (3)	0.0910 (3)	0.06488 (7)	0.0510 (6)
C24	0.2928 (2)	0.6472 (2)	0.19600 (7)	0.0420 (5)
C25	0.3679 (3)	0.6194 (2)	0.24281 (8)	0.0491 (5)
C26	0.2367 (3)	0.7900 (3)	0.18669 (8)	0.0502 (5)
H16	0.375 (2)	0.208 (2)	0.1455 (7)	0.053 (6)*
H17	0.400 (3)	0.380 (2)	0.2023 (8)	0.055 (6)*
H19	0.152 (3)	0.668 (2)	0.1072 (7)	0.059 (6)*
H20	0.128 (3)	0.496 (2)	0.0507 (7)	0.054 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0828 (14)	0.0546 (14)	0.0455 (12)	0.0161 (11)	−0.0105 (10)	−0.0057 (11)
N2	0.0853 (14)	0.0770 (15)	0.0468 (12)	0.0103 (11)	−0.0045 (11)	0.0014 (11)
N3	0.0914 (14)	0.0511 (13)	0.0672 (14)	0.0174 (12)	−0.0032 (11)	−0.0074 (11)
N4	0.0893 (14)	0.0639 (14)	0.0503 (13)	−0.0007 (11)	−0.0069 (11)	−0.0034 (10)
N5	0.0883 (14)	0.0552 (14)	0.0758 (16)	0.0161 (12)	−0.0025 (12)	−0.0010 (12)
O1	0.0967 (12)	0.0819 (13)	0.0449 (10)	0.0278 (10)	−0.0190 (9)	0.0017 (9)
O2	0.0776 (10)	0.0491 (10)	0.0442 (9)	0.0158 (8)	−0.0171 (8)	0.0003 (7)
C1	0.0457 (11)	0.0459 (13)	0.0391 (12)	0.0034 (10)	0.0006 (9)	0.0000 (10)
C2	0.0595 (13)	0.0401 (14)	0.0534 (14)	0.0049 (10)	0.0016 (11)	−0.0044 (12)
C3	0.0567 (13)	0.0410 (14)	0.0598 (16)	0.0089 (11)	0.0060 (11)	0.0048 (12)
C4	0.0493 (12)	0.0493 (14)	0.0466 (13)	0.0059 (10)	0.0030 (10)	0.0084 (11)
C5	0.0384 (10)	0.0451 (13)	0.0383 (12)	0.0035 (9)	0.0029 (9)	0.0038 (10)
C6	0.0379 (10)	0.0387 (12)	0.0361 (11)	0.0022 (8)	0.0032 (9)	0.0009 (9)
C7	0.0444 (11)	0.0601 (15)	0.0363 (12)	0.0043 (10)	−0.0014 (9)	0.0034 (11)
C8	0.0396 (10)	0.0426 (12)	0.0363 (11)	0.0019 (9)	0.0006 (9)	0.0014 (10)
C9	0.0365 (10)	0.0484 (13)	0.0389 (12)	−0.0020 (9)	0.0040 (9)	−0.0044 (10)
C10	0.0470 (12)	0.0660 (17)	0.0432 (13)	0.0014 (11)	−0.0004 (10)	−0.0101 (12)
C11	0.0544 (13)	0.0640 (17)	0.0546 (15)	−0.0077 (12)	0.0082 (12)	−0.0193 (14)
C12	0.0574 (13)	0.0459 (15)	0.0588 (16)	−0.0040 (11)	0.0119 (12)	−0.0095 (12)
C13	0.0533 (12)	0.0455 (14)	0.0469 (14)	0.0005 (10)	0.0042 (11)	0.0012 (11)
C14	0.0372 (10)	0.0422 (13)	0.0386 (11)	−0.0023 (9)	0.0039 (9)	−0.0011 (9)
C15	0.0412 (10)	0.0406 (12)	0.0415 (12)	0.0033 (9)	0.0024 (9)	0.0020 (10)
C16	0.0485 (12)	0.0387 (13)	0.0447 (13)	0.0048 (10)	0.0000 (10)	0.0025 (11)
C17	0.0456 (11)	0.0413 (13)	0.0406 (12)	0.0030 (9)	−0.0011 (10)	0.0041 (11)
C18	0.0390 (10)	0.0396 (12)	0.0422 (12)	0.0006 (9)	0.0054 (9)	0.0006 (10)
C19	0.0511 (12)	0.0402 (13)	0.0460 (13)	0.0069 (10)	0.0005 (10)	0.0047 (11)
C20	0.0520 (12)	0.0484 (14)	0.0394 (12)	0.0052 (10)	−0.0047 (10)	0.0020 (11)
C21	0.0460 (11)	0.0444 (13)	0.0439 (12)	0.0036 (10)	0.0013 (9)	−0.0019 (10)
C22	0.0588 (13)	0.0481 (14)	0.0454 (14)	0.0050 (11)	0.0059 (11)	−0.0020 (11)
C23	0.0585 (13)	0.0515 (15)	0.0417 (12)	0.0050 (11)	−0.0016 (10)	−0.0072 (11)
C24	0.0418 (11)	0.0397 (12)	0.0441 (12)	0.0028 (9)	0.0021 (9)	0.0011 (10)
C25	0.0563 (13)	0.0400 (13)	0.0504 (14)	−0.0011 (10)	0.0028 (11)	−0.0045 (11)
C26	0.0533 (12)	0.0491 (15)	0.0473 (13)	0.0052 (11)	0.0013 (10)	−0.0023 (11)

Geometric parameters (Å, º) top

N1—C1	1.351 (3)	C10—C11	1.381 (3)
N1—HN1	0.93 (3)	C10—H10	1.055 (19)
N1—HN2	1.02 (3)	C11—C12	1.383 (3)
N2—C22	1.144 (3)	C11—H11	1.00 (2)
N3—C23	1.141 (3)	C12—C13	1.380 (3)
N4—C25	1.144 (3)	C12—H12	1.00 (2)
N5—C26	1.140 (3)	C13—C14	1.390 (3)
O1—C7	1.222 (2)	C13—H13	0.96 (2)
O2—C8	1.234 (2)	C15—C21	1.376 (3)
C1—C2	1.414 (3)	C15—C16	1.436 (3)
C1—C6	1.417 (3)	C15—C20	1.438 (3)
C2—C3	1.366 (3)	C16—C17	1.347 (3)
C2—H2	1.00 (2)	C16—H16	0.96 (2)
C3—C4	1.390 (3)	C17—C18	1.441 (3)
C3—H3	0.97 (2)	C17—H17	0.97 (2)
C4—C5	1.379 (3)	C18—C24	1.373 (3)
C4—H4	0.98 (2)	C18—C19	1.439 (3)
C5—C6	1.418 (3)	C19—C20	1.340 (3)
C5—C7	1.485 (3)	C19—H19	0.96 (2)
C6—C8	1.463 (3)	C20—H20	0.98 (2)
C7—C9	1.481 (3)	C21—C22	1.430 (3)
C8—O2	1.234 (2)	C21—C23	1.437 (3)
C8—C14	1.485 (3)	C24—C26	1.428 (3)
C9—C10	1.393 (3)	C24—C25	1.431 (3)
C9—C14	1.398 (3)

C1—N1—HN1	118.7 (17)	C13—C12—C11	120.0 (2)
C1—N1—HN2	119.4 (17)	C13—C12—H12	119.2 (13)
HN1—N1—HN2	121 (2)	C11—C12—H12	120.8 (13)
N1—C1—C2	118.4 (2)	C12—C13—C14	120.5 (2)
N1—C1—C6	123.2 (2)	C12—C13—H13	121.5 (12)
C2—C1—C6	118.42 (19)	C14—C13—H13	118.0 (12)
C3—C2—C1	121.0 (2)	C13—C14—C9	119.24 (19)
C3—C2—H2	121.3 (13)	C13—C14—C8	119.39 (18)
C1—C2—H2	117.6 (13)	C9—C14—C8	121.37 (18)
C2—C3—C4	121.2 (2)	C21—C15—C16	121.35 (19)
C2—C3—H3	120.2 (13)	C21—C15—C20	120.32 (19)
C4—C3—H3	118.6 (13)	C16—C15—C20	118.33 (19)
C5—C4—C3	119.5 (2)	C17—C16—C15	120.5 (2)
C5—C4—H4	115.9 (13)	C17—C16—H16	119.3 (12)
C3—C4—H4	124.6 (13)	C15—C16—H16	120.2 (12)
C4—C5—C6	120.99 (19)	C16—C17—C18	121.4 (2)
C4—C5—C7	117.90 (18)	C16—C17—H17	119.6 (12)
C6—C5—C7	121.10 (18)	C18—C17—H17	118.9 (12)
C1—C6—C5	118.88 (18)	C24—C18—C19	120.93 (19)
C1—C6—C8	121.13 (17)	C24—C18—C17	121.53 (19)
C5—C6—C8	119.99 (18)	C19—C18—C17	117.54 (19)
O1—C7—C9	120.8 (2)	C20—C19—C18	121.3 (2)
O1—C7—C5	120.8 (2)	C20—C19—H19	117.4 (13)
C9—C7—C5	118.33 (17)	C18—C19—H19	121.4 (13)
O2—C8—C6	121.95 (18)	C19—C20—C15	121.0 (2)
O2—C8—C6	121.95 (18)	C19—C20—H20	121.3 (12)
O2—C8—C14	119.13 (18)	C15—C20—H20	117.7 (12)
O2—C8—C14	119.13 (18)	C15—C21—C22	122.92 (19)
C6—C8—C14	118.91 (17)	C15—C21—C23	122.28 (19)
C10—C9—C14	120.2 (2)	C22—C21—C23	114.79 (19)
C10—C9—C7	119.60 (19)	N2—C22—C21	178.0 (2)
C14—C9—C7	120.23 (18)	N3—C23—C21	177.3 (2)
C11—C10—C9	119.5 (2)	C18—C24—C26	122.18 (19)
C11—C10—H10	121.0 (10)	C18—C24—C25	122.36 (18)
C9—C10—H10	119.4 (10)	C26—C24—C25	115.45 (18)
C10—C11—C12	120.6 (2)	N4—C25—C24	178.2 (2)
C10—C11—H11	120.1 (13)	N5—C26—C24	178.6 (2)
C12—C11—H11	119.2 (13)

N1—C1—C2—C3	−178.0 (2)	C10—C11—C12—C13	−0.6 (3)
C6—C1—C2—C3	1.3 (3)	C11—C12—C13—C14	0.3 (3)
C1—C2—C3—C4	−0.4 (3)	C12—C13—C14—C9	−0.2 (3)
C2—C3—C4—C5	−0.2 (3)	C12—C13—C14—C8	179.16 (18)
C3—C4—C5—C6	0.0 (3)	C10—C9—C14—C13	0.3 (3)
C3—C4—C5—C7	−178.83 (19)	C7—C9—C14—C13	−179.00 (17)
N1—C1—C6—C5	177.71 (19)	C10—C9—C14—C8	−179.07 (17)
C2—C1—C6—C5	−1.5 (3)	C7—C9—C14—C8	1.7 (3)
N1—C1—C6—C8	−2.6 (3)	O2—C8—C14—C13	−3.1 (3)
C2—C1—C6—C8	178.24 (17)	O2—C8—C14—C13	−3.1 (3)
C4—C5—C6—C1	0.9 (3)	C6—C8—C14—C13	177.34 (16)
C7—C5—C6—C1	179.67 (17)	O2—C8—C14—C9	176.20 (17)
C4—C5—C6—C8	−178.84 (17)	O2—C8—C14—C9	176.20 (17)
C7—C5—C6—C8	−0.1 (3)	C6—C8—C14—C9	−3.3 (3)
C4—C5—C7—O1	−0.9 (3)	C21—C15—C16—C17	−179.88 (19)
C6—C5—C7—O1	−179.75 (19)	C20—C15—C16—C17	−0.1 (3)
C4—C5—C7—C9	177.21 (16)	C15—C16—C17—C18	−0.4 (3)
C6—C5—C7—C9	−1.6 (3)	C16—C17—C18—C24	−179.60 (19)
O2—O2—C8—C6	0.00 (9)	C16—C17—C18—C19	0.4 (3)
O2—O2—C8—C14	0.00 (10)	C24—C18—C19—C20	−179.88 (19)
C1—C6—C8—O2	3.2 (3)	C17—C18—C19—C20	0.1 (3)
C5—C6—C8—O2	−177.04 (18)	C18—C19—C20—C15	−0.6 (3)
C1—C6—C8—O2	3.2 (3)	C21—C15—C20—C19	−179.6 (2)
C5—C6—C8—O2	−177.04 (18)	C16—C15—C20—C19	0.6 (3)
C1—C6—C8—C14	−177.26 (17)	C16—C15—C21—C22	176.89 (18)
C5—C6—C8—C14	2.5 (3)	C20—C15—C21—C22	−2.9 (3)
O1—C7—C9—C10	−0.3 (3)	C16—C15—C21—C23	−1.7 (3)
C5—C7—C9—C10	−178.49 (17)	C20—C15—C21—C23	178.58 (18)
O1—C7—C9—C14	178.94 (19)	C19—C18—C24—C26	−2.7 (3)
C5—C7—C9—C14	0.8 (3)	C17—C18—C24—C26	177.26 (18)
C14—C9—C10—C11	−0.5 (3)	C19—C18—C24—C25	178.53 (18)
C7—C9—C10—C11	178.78 (18)	C17—C18—C24—C25	−1.5 (3)
C9—C10—C11—C12	0.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O2	0.93 (3)	1.96 (3)	2.654 (3)	130 (2)
N1—HN1···O2ⁱ	0.93 (3)	2.25 (3)	3.019 (3)	139 (2)
N1—HN2···N3ⁱⁱ	1.02 (3)	2.22 (3)	3.229 (3)	171 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₄N₄·C₁₄H₉NO₂
M_r	427.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.4916 (2), 9.4321 (3), 28.8093 (8)
β (°)	95.8785 (15)
V (Å³)	2025.00 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.29 × 0.05 × 0.04

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Analytical (Alcock, 1970)
T_min, T_max	0.974, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	19055, 3972, 2324
R_int	0.147
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.135, 1.01
No. of reflections	3972
No. of parameters	350
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.16

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O2	0.93 (3)	1.96 (3)	2.654 (3)	130 (2)
N1—HN1···O2ⁱ	0.93 (3)	2.25 (3)	3.019 (3)	139 (2)
N1—HN2···N3ⁱⁱ	1.02 (3)	2.22 (3)	3.229 (3)	171 (2)

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

Acknowledgements

We gratefully acknowledge financial support by the German Research Foundation (DFG) through the Collaborative Research Center SFB 813, Chemistry at Spin Centers, and by FAPITEC/SE/FUNTEC/CNPq through the PPP Program 04/2011. JNS also acknowledges CAPES for the award of a scholarship.

References

Alcock, N. W. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, p. 271. Copenhagen: Munksgaard. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Jérome, D. (2004). Chem. Rev. 104, 5565–5591. Web of Science PubMed Google Scholar
Kaim, W. & Moscherosch, M. (1994). Coord. Chem. Rev. 129, 157–193. CrossRef CAS Web of Science Google Scholar
Milić, D., Džolić, Z., Cametti, M., Prugovečki, B. & Žinić, M. (2012). J. Mol. Struct. 920, 178–182. Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Press, D. J., Back, T. G. & Sutherland, T. C. (2012). Tetrahedron Lett. 53, 1603–1605. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o301

doi:10.1107/S1600536813002195

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

The charge-transfer complex 1-amino­anthra­quinone–7,7′,8,8′-tetra­cyano­quinodi­methane (1/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

The charge-transfer complex 1-aminoanthraquinone–7,7′,8,8′-tetracyanoquinodimethane (1/1)