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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
CCDC reference: 146066
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).
Crystal data top
C8H11N·C10H2N4 | Z = 2 |
Mr = 299.33 | F(000) = 312 |
Triclinic, P1 | Dx = 1.331 Mg m−3 Dm = not mesured Mg m−3 Dm measured by not measured |
a = 7.325 (3) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 7.982 (4) Å | Cell parameters from 25 reflections |
c = 13.452 (6) Å | θ = 6.5–13.1° |
α = 74.44 (4)° | µ = 0.08 mm−1 |
β = 87.05 (3)° | T = 100 K |
γ = 80.30 (3)° | Plate, brown |
V = 746.8 (6) Å3 | 0.45 × 0.35 × 0.15 mm |
Data collection top
Enraf-Nonius CAD4 diffractometer | 2501 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
Graphite monochromator | θmax = 28.0°, θmin = 1.6° |
ω–2θ scans | h = 0→9 |
Absorption correction: gaussian Platon (Spek, 1998) | k = −10→10 |
Tmin = 0.973, Tmax = 0.988 | l = −17→17 |
3648 measured reflections | 3 standard reflections every 60 min |
3603 independent reflections | intensity decay: 12% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.150 | Calculated w = 1/[σ2(Fo2) + (0.0806P)2 + 0.2695P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.002 |
3603 reflections | Δρmax = 0.33 e Å−3 |
211 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.4545 (2) | 0.2873 (2) | 0.28746 (12) | 0.0178 (3) | |
C2 | 0.5234 (2) | 0.3766 (2) | 0.19209 (12) | 0.0194 (3) | |
H2 | 0.5195 | 0.5005 | 0.1761 | 0.023* | |
C3 | 0.5966 (2) | 0.2858 (2) | 0.12149 (13) | 0.0242 (4) | |
H3 | 0.6413 | 0.3487 | 0.0571 | 0.029* | |
C4 | 0.6065 (2) | 0.1056 (3) | 0.14221 (15) | 0.0267 (4) | |
H4 | 0.6552 | 0.0445 | 0.0925 | 0.032* | |
C5 | 0.5440 (2) | 0.0163 (2) | 0.23684 (15) | 0.0265 (4) | |
H5 | 0.5526 | −0.1081 | 0.2528 | 0.032* | |
C6 | 0.4688 (2) | 0.1038 (2) | 0.30913 (14) | 0.0225 (4) | |
H6 | 0.4268 | 0.0391 | 0.3738 | 0.027* | |
N1 | 0.3672 (2) | 0.37941 (19) | 0.35501 (11) | 0.0221 (3) | |
C7 | 0.4002 (3) | 0.5574 (2) | 0.34391 (16) | 0.0293 (4) | |
H71 | 0.3288 | 0.6057 | 0.3964 | 0.041* | |
H72 | 0.3616 | 0.6308 | 0.2751 | 0.041* | |
H73 | 0.5324 | 0.5562 | 0.3527 | 0.041* | |
C8 | 0.3250 (3) | 0.2832 (3) | 0.45917 (14) | 0.0307 (4) | |
H81 | 0.2578 | 0.1883 | 0.4565 | 0.043* | |
H82 | 0.2481 | 0.3636 | 0.4940 | 0.043* | |
H83 | 0.4404 | 0.2329 | 0.4974 | 0.043* | |
C11 | −0.0416 (2) | 0.2050 (2) | 0.30765 (12) | 0.0160 (3) | |
C12 | −0.0001 (2) | 0.3693 (2) | 0.25121 (12) | 0.0164 (3) | |
C13 | 0.0828 (2) | 0.3884 (2) | 0.15502 (12) | 0.0172 (3) | |
H13 | 0.1122 | 0.4995 | 0.1171 | 0.021* | |
C14 | 0.1226 (2) | 0.2436 (2) | 0.11426 (12) | 0.0161 (3) | |
C15 | 0.0794 (2) | 0.0804 (2) | 0.17050 (12) | 0.0160 (3) | |
C16 | −0.0017 (2) | 0.0604 (2) | 0.26718 (12) | 0.0167 (3) | |
H16 | −0.0297 | −0.0510 | 0.3054 | 0.020* | |
C17 | −0.1242 (2) | 0.1861 (2) | 0.40830 (13) | 0.0187 (3) | |
C18 | −0.0433 (2) | 0.5188 (2) | 0.29338 (13) | 0.0199 (3) | |
C19 | 0.2067 (2) | 0.2641 (2) | 0.01405 (13) | 0.0184 (3) | |
C20 | 0.1214 (2) | −0.0682 (2) | 0.12705 (12) | 0.0190 (3) | |
N11 | −0.1864 (2) | 0.1714 (2) | 0.48905 (11) | 0.0257 (3) | |
N12 | −0.0801 (2) | 0.63783 (19) | 0.32639 (12) | 0.0247 (3) | |
N13 | 0.2700 (2) | 0.2827 (2) | −0.06665 (11) | 0.0252 (3) | |
N14 | 0.1545 (2) | −0.18553 (19) | 0.09263 (12) | 0.0259 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0142 (7) | 0.0209 (8) | 0.0182 (8) | −0.0039 (6) | −0.0020 (6) | −0.0038 (6) |
C2 | 0.0178 (8) | 0.0182 (7) | 0.0206 (8) | −0.0036 (6) | 0.0000 (6) | −0.0021 (6) |
C3 | 0.0183 (8) | 0.0349 (10) | 0.0189 (8) | −0.0061 (7) | 0.0024 (6) | −0.0056 (7) |
C4 | 0.0200 (8) | 0.0333 (10) | 0.0308 (10) | −0.0009 (7) | 0.0003 (7) | −0.0174 (8) |
C5 | 0.0219 (8) | 0.0181 (8) | 0.0400 (11) | −0.0020 (6) | −0.0046 (7) | −0.0085 (7) |
C6 | 0.0200 (8) | 0.0198 (8) | 0.0246 (8) | −0.0051 (6) | −0.0019 (6) | 0.0010 (6) |
N1 | 0.0219 (7) | 0.0255 (7) | 0.0196 (7) | −0.0048 (6) | 0.0032 (5) | −0.0072 (6) |
C7 | 0.0291 (9) | 0.0283 (9) | 0.0356 (10) | −0.0046 (7) | −0.0006 (8) | −0.0169 (8) |
C8 | 0.0271 (9) | 0.0465 (11) | 0.0183 (8) | −0.0077 (8) | 0.0043 (7) | −0.0078 (8) |
C11 | 0.0151 (7) | 0.0172 (7) | 0.0157 (7) | −0.0039 (6) | 0.0013 (6) | −0.0037 (6) |
C12 | 0.0147 (7) | 0.0162 (7) | 0.0181 (7) | −0.0031 (6) | −0.0001 (6) | −0.0039 (6) |
C13 | 0.0166 (7) | 0.0151 (7) | 0.0190 (8) | −0.0046 (6) | −0.0013 (6) | −0.0012 (6) |
C14 | 0.0154 (7) | 0.0172 (7) | 0.0154 (7) | −0.0039 (6) | −0.0001 (6) | −0.0028 (6) |
C15 | 0.0164 (7) | 0.0146 (7) | 0.0176 (7) | −0.0032 (6) | −0.0009 (6) | −0.0045 (6) |
C16 | 0.0167 (7) | 0.0138 (7) | 0.0189 (8) | −0.0036 (6) | 0.0008 (6) | −0.0028 (6) |
C17 | 0.0179 (7) | 0.0157 (7) | 0.0224 (8) | −0.0030 (6) | 0.0011 (6) | −0.0051 (6) |
C18 | 0.0201 (8) | 0.0183 (8) | 0.0202 (8) | −0.0055 (6) | 0.0026 (6) | −0.0023 (6) |
C19 | 0.0202 (8) | 0.0153 (7) | 0.0202 (8) | −0.0051 (6) | −0.0008 (6) | −0.0038 (6) |
C20 | 0.0224 (8) | 0.0162 (7) | 0.0175 (7) | −0.0061 (6) | 0.0017 (6) | −0.0016 (6) |
N11 | 0.0271 (8) | 0.0268 (8) | 0.0230 (8) | −0.0055 (6) | 0.0051 (6) | −0.0064 (6) |
N12 | 0.0292 (8) | 0.0185 (7) | 0.0266 (8) | −0.0046 (6) | 0.0059 (6) | −0.0070 (6) |
N13 | 0.0315 (8) | 0.0239 (7) | 0.0205 (7) | −0.0091 (6) | 0.0035 (6) | −0.0043 (6) |
N14 | 0.0342 (8) | 0.0196 (7) | 0.0255 (8) | −0.0083 (6) | 0.0061 (6) | −0.0071 (6) |
Geometric parameters (Å, º) top
C1—N1 | 1.384 (2) | C12—C13 | 1.382 (2) |
C1—C6 | 1.401 (2) | C12—C18 | 1.437 (2) |
C1—C2 | 1.404 (2) | C13—C14 | 1.390 (2) |
C2—C3 | 1.379 (2) | C14—C15 | 1.398 (2) |
C3—C4 | 1.380 (3) | C14—C19 | 1.433 (2) |
C4—C5 | 1.379 (3) | C15—C16 | 1.382 (2) |
C5—C6 | 1.384 (3) | C15—C20 | 1.440 (2) |
N1—C7 | 1.448 (2) | C17—N11 | 1.140 (2) |
N1—C8 | 1.451 (2) | C18—N12 | 1.140 (2) |
C11—C16 | 1.386 (2) | C19—N13 | 1.140 (2) |
C11—C12 | 1.401 (2) | C20—N14 | 1.138 (2) |
C11—C17 | 1.435 (2) | | |
| | | |
N1—C1—C6 | 121.48 (15) | C13—C12—C18 | 119.63 (14) |
N1—C1—C2 | 120.69 (15) | C11—C12—C18 | 119.99 (15) |
C6—C1—C2 | 117.75 (16) | C12—C13—C14 | 119.33 (15) |
C3—C2—C1 | 120.50 (16) | C13—C14—C15 | 120.08 (15) |
C4—C3—C2 | 121.51 (17) | C13—C14—C19 | 119.31 (14) |
C3—C4—C5 | 118.33 (17) | C15—C14—C19 | 120.61 (14) |
C4—C5—C6 | 121.52 (17) | C16—C15—C14 | 120.71 (15) |
C5—C6—C1 | 120.34 (16) | C16—C15—C20 | 119.95 (14) |
C1—N1—C7 | 118.76 (15) | C14—C15—C20 | 119.34 (15) |
C1—N1—C8 | 119.20 (15) | C15—C16—C11 | 119.15 (15) |
C7—N1—C8 | 115.22 (15) | N11—C17—C11 | 178.58 (18) |
C16—C11—C12 | 120.35 (15) | N12—C18—C12 | 179.04 (18) |
C16—C11—C17 | 119.82 (14) | N13—C19—C14 | 178.44 (18) |
C12—C11—C17 | 119.82 (14) | N14—C20—C15 | 179.91 (18) |
C13—C12—C11 | 120.38 (15) | | |
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