Literature DB >> 23424566

The charge-transfer complex 1-amino-anthraquinone-7,7',8,8'-tetra-cyano-quinodimethane (1/1).

Adriano Bof de Oliveira1, Johannes Beck, Jörg Daniels, Jaciara Nascimento Santos, Bárbara Regina Santos Feitosa.   

Abstract

The reaction of 1-amino-anthraquinone with 7,7',8,8'-tetra-cyano-quinodimethane yielded the title charge-transfer complex, C(14)H(9)NO(2)·C(12)H(4)N(4). The mol-ecules 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, mol-ecules are stacked into columns along the a-axis direction. Pairs of N-H⋯N and N-H⋯O inter-actions connect the mol-ecules perpendicular to the stacking direction. Additionally, an intra-molecular N-H⋯O hydrogen-bond inter-action is observed for 1-amino-anthraquinone.

Entities:  

Year:  2013        PMID： 23424566      PMCID： PMC3569820          DOI： 10.1107/S1600536813002195

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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 = 427.41 Monoclinic, 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[F 2 > 2σ(F 2)] = 0.052 wR(F 2) = 0.135 S = 1.01 3972 reflections 350 parameters All H-atom parameters refined Δρmax = 0.16 e Å−3 Δρmin = −0.16 e Å−3 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 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813002195/bt6884sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002195/bt6884Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813002195/bt6884Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C12H4N4·C14H9NO2F(000) = 880
Mr = 427.41Dx = 1.402 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 14532 reflections
a = 7.4916 (2) Åθ = 2.9–27.5°
b = 9.4321 (3) ŵ = 0.09 mm−1
c = 28.8093 (8) ÅT = 293 K
β = 95.8785 (15)°Needle, dark brown
V = 2025.00 (10) Å30.29 × 0.05 × 0.04 mm
Z = 4
Nonius KappaCCD diffractometer3972 independent reflections
Radiation source: fine-focus sealed tube2324 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.147
Detector resolution: 9 pixels mm-1θmax = 26.0°, θmin = 3.0°
CCD rotation images, thick slices scansh = −9→9
Absorption correction: analytical (Alcock, 1970)k = −11→11
Tmin = 0.974, Tmax = 0.996l = −32→35
19055 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135All H-atom parameters refined
S = 1.01w = 1/[σ2(Fo2) + (0.0558P)2 + 0.1436P] where P = (Fo2 + 2Fc2)/3
3972 reflections(Δ/σ)max < 0.001
350 parametersΔρmax = 0.16 e Å−3
0 restraintsΔρmin = −0.16 e Å−3
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.
xyzUiso*/Ueq
N10.6301 (3)0.2662 (3)0.00915 (7)0.0621 (6)
HN10.586 (3)0.358 (3)0.0048 (9)0.086 (9)*
HN20.625 (3)0.195 (3)−0.0176 (11)0.110 (10)*
N20.0775 (3)0.2756 (2)−0.02511 (7)0.0705 (6)
N30.3548 (3)−0.0224 (2)0.06905 (7)0.0707 (6)
N40.4265 (3)0.6007 (2)0.28057 (7)0.0688 (6)
N50.1954 (3)0.9047 (2)0.17933 (8)0.0739 (6)
O10.9414 (2)0.33407 (19)0.20941 (6)0.0763 (5)
O20.58619 (19)0.51563 (15)0.04905 (5)0.0586 (4)
C10.7206 (2)0.2324 (2)0.05065 (7)0.0438 (5)
C20.7953 (3)0.0950 (2)0.05632 (8)0.0513 (6)
H20.776 (3)0.028 (2)0.0292 (8)0.070 (7)*
C30.8834 (3)0.0533 (3)0.09792 (8)0.0525 (6)
H30.936 (3)−0.040 (3)0.1011 (8)0.066 (7)*
C40.9037 (3)0.1446 (2)0.13595 (8)0.0485 (6)
H40.971 (3)0.122 (2)0.1661 (9)0.069 (7)*
C50.8342 (2)0.2799 (2)0.13162 (7)0.0407 (5)
C60.7425 (2)0.3273 (2)0.08894 (7)0.0376 (5)
C70.8617 (2)0.3753 (2)0.17276 (7)0.0473 (5)
C80.6729 (2)0.4722 (2)0.08494 (7)0.0397 (5)
C90.7950 (2)0.5229 (2)0.16781 (7)0.0413 (5)
C100.8227 (3)0.6157 (3)0.20549 (8)0.0524 (6)
H100.895 (2)0.5807 (18)0.2367 (7)0.039 (5)*
C110.7634 (3)0.7541 (3)0.20053 (9)0.0574 (6)
H110.785 (3)0.822 (2)0.2272 (9)0.072 (7)*
C120.6755 (3)0.8007 (3)0.15876 (9)0.0536 (6)
H120.631 (3)0.900 (2)0.1552 (7)0.061 (6)*
C130.6477 (3)0.7089 (2)0.12139 (8)0.0486 (5)
H130.591 (3)0.740 (2)0.0917 (8)0.052 (6)*
C140.7067 (2)0.5693 (2)0.12546 (7)0.0393 (5)
C150.2500 (2)0.3339 (2)0.09187 (7)0.0412 (5)
C160.3302 (3)0.3018 (2)0.13811 (7)0.0443 (5)
C170.3431 (3)0.4023 (2)0.17152 (8)0.0429 (5)
C180.2788 (2)0.5444 (2)0.16208 (7)0.0402 (5)
C190.1987 (3)0.5751 (2)0.11561 (7)0.0461 (5)
C200.1842 (3)0.4753 (2)0.08236 (8)0.0472 (5)
C210.2352 (2)0.2327 (2)0.05729 (7)0.0450 (5)
C220.1486 (3)0.2588 (2)0.01153 (8)0.0507 (6)
C230.3026 (3)0.0910 (3)0.06488 (7)0.0510 (6)
C240.2928 (2)0.6472 (2)0.19600 (7)0.0420 (5)
C250.3679 (3)0.6194 (2)0.24281 (8)0.0491 (5)
C260.2367 (3)0.7900 (3)0.18669 (8)0.0502 (5)
H160.375 (2)0.208 (2)0.1455 (7)0.053 (6)*
H170.400 (3)0.380 (2)0.2023 (8)0.055 (6)*
H190.152 (3)0.668 (2)0.1072 (7)0.059 (6)*
H200.128 (3)0.496 (2)0.0507 (7)0.054 (6)*
U11U22U33U12U13U23
N10.0828 (14)0.0546 (14)0.0455 (12)0.0161 (11)−0.0105 (10)−0.0057 (11)
N20.0853 (14)0.0770 (15)0.0468 (12)0.0103 (11)−0.0045 (11)0.0014 (11)
N30.0914 (14)0.0511 (13)0.0672 (14)0.0174 (12)−0.0032 (11)−0.0074 (11)
N40.0893 (14)0.0639 (14)0.0503 (13)−0.0007 (11)−0.0069 (11)−0.0034 (10)
N50.0883 (14)0.0552 (14)0.0758 (16)0.0161 (12)−0.0025 (12)−0.0010 (12)
O10.0967 (12)0.0819 (13)0.0449 (10)0.0278 (10)−0.0190 (9)0.0017 (9)
O20.0776 (10)0.0491 (10)0.0442 (9)0.0158 (8)−0.0171 (8)0.0003 (7)
C10.0457 (11)0.0459 (13)0.0391 (12)0.0034 (10)0.0006 (9)0.0000 (10)
C20.0595 (13)0.0401 (14)0.0534 (14)0.0049 (10)0.0016 (11)−0.0044 (12)
C30.0567 (13)0.0410 (14)0.0598 (16)0.0089 (11)0.0060 (11)0.0048 (12)
C40.0493 (12)0.0493 (14)0.0466 (13)0.0059 (10)0.0030 (10)0.0084 (11)
C50.0384 (10)0.0451 (13)0.0383 (12)0.0035 (9)0.0029 (9)0.0038 (10)
C60.0379 (10)0.0387 (12)0.0361 (11)0.0022 (8)0.0032 (9)0.0009 (9)
C70.0444 (11)0.0601 (15)0.0363 (12)0.0043 (10)−0.0014 (9)0.0034 (11)
C80.0396 (10)0.0426 (12)0.0363 (11)0.0019 (9)0.0006 (9)0.0014 (10)
C90.0365 (10)0.0484 (13)0.0389 (12)−0.0020 (9)0.0040 (9)−0.0044 (10)
C100.0470 (12)0.0660 (17)0.0432 (13)0.0014 (11)−0.0004 (10)−0.0101 (12)
C110.0544 (13)0.0640 (17)0.0546 (15)−0.0077 (12)0.0082 (12)−0.0193 (14)
C120.0574 (13)0.0459 (15)0.0588 (16)−0.0040 (11)0.0119 (12)−0.0095 (12)
C130.0533 (12)0.0455 (14)0.0469 (14)0.0005 (10)0.0042 (11)0.0012 (11)
C140.0372 (10)0.0422 (13)0.0386 (11)−0.0023 (9)0.0039 (9)−0.0011 (9)
C150.0412 (10)0.0406 (12)0.0415 (12)0.0033 (9)0.0024 (9)0.0020 (10)
C160.0485 (12)0.0387 (13)0.0447 (13)0.0048 (10)0.0000 (10)0.0025 (11)
C170.0456 (11)0.0413 (13)0.0406 (12)0.0030 (9)−0.0011 (10)0.0041 (11)
C180.0390 (10)0.0396 (12)0.0422 (12)0.0006 (9)0.0054 (9)0.0006 (10)
C190.0511 (12)0.0402 (13)0.0460 (13)0.0069 (10)0.0005 (10)0.0047 (11)
C200.0520 (12)0.0484 (14)0.0394 (12)0.0052 (10)−0.0047 (10)0.0020 (11)
C210.0460 (11)0.0444 (13)0.0439 (12)0.0036 (10)0.0013 (9)−0.0019 (10)
C220.0588 (13)0.0481 (14)0.0454 (14)0.0050 (11)0.0059 (11)−0.0020 (11)
C230.0585 (13)0.0515 (15)0.0417 (12)0.0050 (11)−0.0016 (10)−0.0072 (11)
C240.0418 (11)0.0397 (12)0.0441 (12)0.0028 (9)0.0021 (9)0.0011 (10)
C250.0563 (13)0.0400 (13)0.0504 (14)−0.0011 (10)0.0028 (11)−0.0045 (11)
C260.0533 (12)0.0491 (15)0.0473 (13)0.0052 (11)0.0013 (10)−0.0023 (11)
N1—C11.351 (3)C10—C111.381 (3)
N1—HN10.93 (3)C10—H101.055 (19)
N1—HN21.02 (3)C11—C121.383 (3)
N2—C221.144 (3)C11—H111.00 (2)
N3—C231.141 (3)C12—C131.380 (3)
N4—C251.144 (3)C12—H121.00 (2)
N5—C261.140 (3)C13—C141.390 (3)
O1—C71.222 (2)C13—H130.96 (2)
O2—C81.234 (2)C15—C211.376 (3)
C1—C21.414 (3)C15—C161.436 (3)
C1—C61.417 (3)C15—C201.438 (3)
C2—C31.366 (3)C16—C171.347 (3)
C2—H21.00 (2)C16—H160.96 (2)
C3—C41.390 (3)C17—C181.441 (3)
C3—H30.97 (2)C17—H170.97 (2)
C4—C51.379 (3)C18—C241.373 (3)
C4—H40.98 (2)C18—C191.439 (3)
C5—C61.418 (3)C19—C201.340 (3)
C5—C71.485 (3)C19—H190.96 (2)
C6—C81.463 (3)C20—H200.98 (2)
C7—C91.481 (3)C21—C221.430 (3)
C8—O21.234 (2)C21—C231.437 (3)
C8—C141.485 (3)C24—C261.428 (3)
C9—C101.393 (3)C24—C251.431 (3)
C9—C141.398 (3)
C1—N1—HN1118.7 (17)C13—C12—C11120.0 (2)
C1—N1—HN2119.4 (17)C13—C12—H12119.2 (13)
HN1—N1—HN2121 (2)C11—C12—H12120.8 (13)
N1—C1—C2118.4 (2)C12—C13—C14120.5 (2)
N1—C1—C6123.2 (2)C12—C13—H13121.5 (12)
C2—C1—C6118.42 (19)C14—C13—H13118.0 (12)
C3—C2—C1121.0 (2)C13—C14—C9119.24 (19)
C3—C2—H2121.3 (13)C13—C14—C8119.39 (18)
C1—C2—H2117.6 (13)C9—C14—C8121.37 (18)
C2—C3—C4121.2 (2)C21—C15—C16121.35 (19)
C2—C3—H3120.2 (13)C21—C15—C20120.32 (19)
C4—C3—H3118.6 (13)C16—C15—C20118.33 (19)
C5—C4—C3119.5 (2)C17—C16—C15120.5 (2)
C5—C4—H4115.9 (13)C17—C16—H16119.3 (12)
C3—C4—H4124.6 (13)C15—C16—H16120.2 (12)
C4—C5—C6120.99 (19)C16—C17—C18121.4 (2)
C4—C5—C7117.90 (18)C16—C17—H17119.6 (12)
C6—C5—C7121.10 (18)C18—C17—H17118.9 (12)
C1—C6—C5118.88 (18)C24—C18—C19120.93 (19)
C1—C6—C8121.13 (17)C24—C18—C17121.53 (19)
C5—C6—C8119.99 (18)C19—C18—C17117.54 (19)
O1—C7—C9120.8 (2)C20—C19—C18121.3 (2)
O1—C7—C5120.8 (2)C20—C19—H19117.4 (13)
C9—C7—C5118.33 (17)C18—C19—H19121.4 (13)
O2—C8—C6121.95 (18)C19—C20—C15121.0 (2)
O2—C8—C6121.95 (18)C19—C20—H20121.3 (12)
O2—C8—C14119.13 (18)C15—C20—H20117.7 (12)
O2—C8—C14119.13 (18)C15—C21—C22122.92 (19)
C6—C8—C14118.91 (17)C15—C21—C23122.28 (19)
C10—C9—C14120.2 (2)C22—C21—C23114.79 (19)
C10—C9—C7119.60 (19)N2—C22—C21178.0 (2)
C14—C9—C7120.23 (18)N3—C23—C21177.3 (2)
C11—C10—C9119.5 (2)C18—C24—C26122.18 (19)
C11—C10—H10121.0 (10)C18—C24—C25122.36 (18)
C9—C10—H10119.4 (10)C26—C24—C25115.45 (18)
C10—C11—C12120.6 (2)N4—C25—C24178.2 (2)
C10—C11—H11120.1 (13)N5—C26—C24178.6 (2)
C12—C11—H11119.2 (13)
N1—C1—C2—C3−178.0 (2)C10—C11—C12—C13−0.6 (3)
C6—C1—C2—C31.3 (3)C11—C12—C13—C140.3 (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—C8179.16 (18)
C3—C4—C5—C60.0 (3)C10—C9—C14—C130.3 (3)
C3—C4—C5—C7−178.83 (19)C7—C9—C14—C13−179.00 (17)
N1—C1—C6—C5177.71 (19)C10—C9—C14—C8−179.07 (17)
C2—C1—C6—C5−1.5 (3)C7—C9—C14—C81.7 (3)
N1—C1—C6—C8−2.6 (3)O2—C8—C14—C13−3.1 (3)
C2—C1—C6—C8178.24 (17)O2—C8—C14—C13−3.1 (3)
C4—C5—C6—C10.9 (3)C6—C8—C14—C13177.34 (16)
C7—C5—C6—C1179.67 (17)O2—C8—C14—C9176.20 (17)
C4—C5—C6—C8−178.84 (17)O2—C8—C14—C9176.20 (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—C9177.21 (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—C60.00 (9)C16—C17—C18—C190.4 (3)
O2—O2—C8—C140.00 (10)C24—C18—C19—C20−179.88 (19)
C1—C6—C8—O23.2 (3)C17—C18—C19—C200.1 (3)
C5—C6—C8—O2−177.04 (18)C18—C19—C20—C15−0.6 (3)
C1—C6—C8—O23.2 (3)C21—C15—C20—C19−179.6 (2)
C5—C6—C8—O2−177.04 (18)C16—C15—C20—C190.6 (3)
C1—C6—C8—C14−177.26 (17)C16—C15—C21—C22176.89 (18)
C5—C6—C8—C142.5 (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—C23178.58 (18)
O1—C7—C9—C14178.94 (19)C19—C18—C24—C26−2.7 (3)
C5—C7—C9—C140.8 (3)C17—C18—C24—C26177.26 (18)
C14—C9—C10—C11−0.5 (3)C19—C18—C24—C25178.53 (18)
C7—C9—C10—C11178.78 (18)C17—C18—C24—C25−1.5 (3)
C9—C10—C11—C120.6 (3)
D—H···AD—HH···AD···AD—H···A
N1—HN1···O20.93 (3)1.96 (3)2.654 (3)130 (2)
N1—HN1···O2i0.93 (3)2.25 (3)3.019 (3)139 (2)
N1—HN2···N3ii1.02 (3)2.22 (3)3.229 (3)171 (2)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1—HN1⋯O20.93 (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) ; (ii) .

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