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The partner mol­ecules of N,N-di­methyl­aniline-1,2,4,5-tetra­cyano­benzene (1/1), C8H11N·C10H2N4, are stacked alternately in infinite columns. The N atom of the N,N-di­methyl­aniline mol­ecule has a partially tetrahedral character and the distance between neighbouring mol­ecules in the stack is relatively short on the side where the lone-pair electrons of this atom are located. Molecular-packing analysis of this and three other complexes of N,N-di­methyl­aniline shows that there is a close relationship between the strength of the intermolecular interaction on this side and the tetrahedral character of the N atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100003590/os1110sup1.cif
Contains datablocks global, DMA-TCNB

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100003590/os1110DMA-TCNBsup2.hkl
Contains datablock DMA-FA

CCDC reference: 146066

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998).

(DMA-TCNB) top
Crystal data top
C8H11N·C10H2N4Z = 2
Mr = 299.33F(000) = 312
Triclinic, P1Dx = 1.331 Mg m3
Dm = not mesured Mg m3
Dm measured by not measured
a = 7.325 (3) ÅMo Kα radiation, λ = 0.71069 Å
b = 7.982 (4) ÅCell parameters from 25 reflections
c = 13.452 (6) Åθ = 6.5–13.1°
α = 74.44 (4)°µ = 0.08 mm1
β = 87.05 (3)°T = 100 K
γ = 80.30 (3)°Plate, brown
V = 746.8 (6) Å30.45 × 0.35 × 0.15 mm
Data collection top
Enraf-Nonius CAD4
diffractometer
2501 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
Graphite monochromatorθmax = 28.0°, θmin = 1.6°
ω–2θ scansh = 09
Absorption correction: gaussian
Platon (Spek, 1998)
k = 1010
Tmin = 0.973, Tmax = 0.988l = 1717
3648 measured reflections3 standard reflections every 60 min
3603 independent reflections intensity decay: 12%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.150Calculated w = 1/[σ2(Fo2) + (0.0806P)2 + 0.2695P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.002
3603 reflectionsΔρmax = 0.33 e Å3
211 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.013 (4)
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
xyzUiso*/Ueq
C10.4545 (2)0.2873 (2)0.28746 (12)0.0178 (3)
C20.5234 (2)0.3766 (2)0.19209 (12)0.0194 (3)
H20.51950.50050.17610.023*
C30.5966 (2)0.2858 (2)0.12149 (13)0.0242 (4)
H30.64130.34870.05710.029*
C40.6065 (2)0.1056 (3)0.14221 (15)0.0267 (4)
H40.65520.04450.09250.032*
C50.5440 (2)0.0163 (2)0.23684 (15)0.0265 (4)
H50.55260.10810.25280.032*
C60.4688 (2)0.1038 (2)0.30913 (14)0.0225 (4)
H60.42680.03910.37380.027*
N10.3672 (2)0.37941 (19)0.35501 (11)0.0221 (3)
C70.4002 (3)0.5574 (2)0.34391 (16)0.0293 (4)
H710.32880.60570.39640.041*
H720.36160.63080.27510.041*
H730.53240.55620.35270.041*
C80.3250 (3)0.2832 (3)0.45917 (14)0.0307 (4)
H810.25780.18830.45650.043*
H820.24810.36360.49400.043*
H830.44040.23290.49740.043*
C110.0416 (2)0.2050 (2)0.30765 (12)0.0160 (3)
C120.0001 (2)0.3693 (2)0.25121 (12)0.0164 (3)
C130.0828 (2)0.3884 (2)0.15502 (12)0.0172 (3)
H130.11220.49950.11710.021*
C140.1226 (2)0.2436 (2)0.11426 (12)0.0161 (3)
C150.0794 (2)0.0804 (2)0.17050 (12)0.0160 (3)
C160.0017 (2)0.0604 (2)0.26718 (12)0.0167 (3)
H160.02970.05100.30540.020*
C170.1242 (2)0.1861 (2)0.40830 (13)0.0187 (3)
C180.0433 (2)0.5188 (2)0.29338 (13)0.0199 (3)
C190.2067 (2)0.2641 (2)0.01405 (13)0.0184 (3)
C200.1214 (2)0.0682 (2)0.12705 (12)0.0190 (3)
N110.1864 (2)0.1714 (2)0.48905 (11)0.0257 (3)
N120.0801 (2)0.63783 (19)0.32639 (12)0.0247 (3)
N130.2700 (2)0.2827 (2)0.06665 (11)0.0252 (3)
N140.1545 (2)0.18553 (19)0.09263 (12)0.0259 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0142 (7)0.0209 (8)0.0182 (8)0.0039 (6)0.0020 (6)0.0038 (6)
C20.0178 (8)0.0182 (7)0.0206 (8)0.0036 (6)0.0000 (6)0.0021 (6)
C30.0183 (8)0.0349 (10)0.0189 (8)0.0061 (7)0.0024 (6)0.0056 (7)
C40.0200 (8)0.0333 (10)0.0308 (10)0.0009 (7)0.0003 (7)0.0174 (8)
C50.0219 (8)0.0181 (8)0.0400 (11)0.0020 (6)0.0046 (7)0.0085 (7)
C60.0200 (8)0.0198 (8)0.0246 (8)0.0051 (6)0.0019 (6)0.0010 (6)
N10.0219 (7)0.0255 (7)0.0196 (7)0.0048 (6)0.0032 (5)0.0072 (6)
C70.0291 (9)0.0283 (9)0.0356 (10)0.0046 (7)0.0006 (8)0.0169 (8)
C80.0271 (9)0.0465 (11)0.0183 (8)0.0077 (8)0.0043 (7)0.0078 (8)
C110.0151 (7)0.0172 (7)0.0157 (7)0.0039 (6)0.0013 (6)0.0037 (6)
C120.0147 (7)0.0162 (7)0.0181 (7)0.0031 (6)0.0001 (6)0.0039 (6)
C130.0166 (7)0.0151 (7)0.0190 (8)0.0046 (6)0.0013 (6)0.0012 (6)
C140.0154 (7)0.0172 (7)0.0154 (7)0.0039 (6)0.0001 (6)0.0028 (6)
C150.0164 (7)0.0146 (7)0.0176 (7)0.0032 (6)0.0009 (6)0.0045 (6)
C160.0167 (7)0.0138 (7)0.0189 (8)0.0036 (6)0.0008 (6)0.0028 (6)
C170.0179 (7)0.0157 (7)0.0224 (8)0.0030 (6)0.0011 (6)0.0051 (6)
C180.0201 (8)0.0183 (8)0.0202 (8)0.0055 (6)0.0026 (6)0.0023 (6)
C190.0202 (8)0.0153 (7)0.0202 (8)0.0051 (6)0.0008 (6)0.0038 (6)
C200.0224 (8)0.0162 (7)0.0175 (7)0.0061 (6)0.0017 (6)0.0016 (6)
N110.0271 (8)0.0268 (8)0.0230 (8)0.0055 (6)0.0051 (6)0.0064 (6)
N120.0292 (8)0.0185 (7)0.0266 (8)0.0046 (6)0.0059 (6)0.0070 (6)
N130.0315 (8)0.0239 (7)0.0205 (7)0.0091 (6)0.0035 (6)0.0043 (6)
N140.0342 (8)0.0196 (7)0.0255 (8)0.0083 (6)0.0061 (6)0.0071 (6)
Geometric parameters (Å, º) top
C1—N11.384 (2)C12—C131.382 (2)
C1—C61.401 (2)C12—C181.437 (2)
C1—C21.404 (2)C13—C141.390 (2)
C2—C31.379 (2)C14—C151.398 (2)
C3—C41.380 (3)C14—C191.433 (2)
C4—C51.379 (3)C15—C161.382 (2)
C5—C61.384 (3)C15—C201.440 (2)
N1—C71.448 (2)C17—N111.140 (2)
N1—C81.451 (2)C18—N121.140 (2)
C11—C161.386 (2)C19—N131.140 (2)
C11—C121.401 (2)C20—N141.138 (2)
C11—C171.435 (2)
N1—C1—C6121.48 (15)C13—C12—C18119.63 (14)
N1—C1—C2120.69 (15)C11—C12—C18119.99 (15)
C6—C1—C2117.75 (16)C12—C13—C14119.33 (15)
C3—C2—C1120.50 (16)C13—C14—C15120.08 (15)
C4—C3—C2121.51 (17)C13—C14—C19119.31 (14)
C3—C4—C5118.33 (17)C15—C14—C19120.61 (14)
C4—C5—C6121.52 (17)C16—C15—C14120.71 (15)
C5—C6—C1120.34 (16)C16—C15—C20119.95 (14)
C1—N1—C7118.76 (15)C14—C15—C20119.34 (15)
C1—N1—C8119.20 (15)C15—C16—C11119.15 (15)
C7—N1—C8115.22 (15)N11—C17—C11178.58 (18)
C16—C11—C12120.35 (15)N12—C18—C12179.04 (18)
C16—C11—C17119.82 (14)N13—C19—C14178.44 (18)
C12—C11—C17119.82 (14)N14—C20—C15179.91 (18)
C13—C12—C11120.38 (15)
 

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