Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807003911/tk2126sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807003911/tk2126Isup2.hkl |
CCDC reference: 636821
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C18H18N4 | F(000) = 308 |
Mr = 290.36 | Dx = 1.272 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11055 reflections |
a = 5.6495 (4) Å | θ = 2.5–28.0° |
b = 10.6323 (7) Å | µ = 0.08 mm−1 |
c = 12.7814 (9) Å | T = 296 K |
β = 99.042 (6)° | Prism, colourless |
V = 758.20 (9) Å3 | 0.43 × 0.35 × 0.27 mm |
Z = 2 |
Stoe IPDS-2 diffractometer | 1354 reflections with I > 2σ(I) |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | Rint = 0.062 |
Plane graphite monochromator | θmax = 27.9°, θmin = 2.5° |
Detector resolution: 6.67 pixels mm-1 | h = −7→6 |
ω scans | k = −13→13 |
11438 measured reflections | l = −16→16 |
1795 independent reflections |
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)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.0449P)2 + 0.023P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
1795 reflections | Δρmax = 0.13 e Å−3 |
101 parameters | Δρmin = −0.11 e Å−3 |
0 restraints | Extinction correction: SHELXL97, fc*=kfc[1+0.001xfc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.086 (8) |
Experimental. 1H NMR (CDCl3): δ 2.37 (m, –CH2–CH2–, 2H), 4.69 (t, –CH2–N, 2H), 7.83–7.98 (m, Ar–H, 4H), 8.63 (s, N–CH–N, 1H). 13C NMR (CDCl3): δ 27.15, 52.13, 114.26, 123.14, 137.34 142.43. Analysis calculated for C18H18N4: C 74.48, H 6.21, N 19.31%; found: C 74.52, H 6.21, N 19.43%. |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
N1 | 0.48136 (15) | 0.17964 (7) | 0.69126 (6) | 0.0532 (3) | |
N2 | 0.39719 (18) | 0.19249 (9) | 0.85641 (6) | 0.0627 (3) | |
C1 | 0.5364 (2) | 0.14428 (10) | 0.79418 (8) | 0.0602 (3) | |
C2 | 0.23568 (19) | 0.26504 (9) | 0.78921 (7) | 0.0533 (3) | |
C3 | 0.0445 (2) | 0.33833 (10) | 0.81037 (8) | 0.0636 (3) | |
C4 | −0.0839 (2) | 0.40365 (10) | 0.72842 (10) | 0.0686 (4) | |
C5 | −0.0281 (2) | 0.39835 (10) | 0.62576 (9) | 0.0660 (4) | |
C6 | 0.1589 (2) | 0.32610 (9) | 0.60215 (8) | 0.0578 (3) | |
C7 | 0.28726 (18) | 0.25912 (8) | 0.68555 (7) | 0.0489 (3) | |
C8 | 0.5877 (2) | 0.13255 (9) | 0.60193 (8) | 0.0571 (3) | |
C9 | 0.44837 (18) | 0.02256 (9) | 0.54801 (7) | 0.0527 (3) | |
H1 | 0.66270 | 0.09030 | 0.81850 | 0.0720* | |
H3 | 0.00540 | 0.34270 | 0.87830 | 0.0760* | |
H4 | −0.21210 | 0.45300 | 0.74130 | 0.0820* | |
H5 | −0.11920 | 0.44460 | 0.57220 | 0.0790* | |
H6 | 0.19710 | 0.32240 | 0.53400 | 0.0690* | |
H8A | 0.75140 | 0.10650 | 0.62690 | 0.0690* | |
H8B | 0.59200 | 0.19980 | 0.55100 | 0.0690* | |
H9A | 0.28280 | 0.04750 | 0.52620 | 0.0630* | |
H9B | 0.45060 | −0.04610 | 0.59810 | 0.0630* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0630 (5) | 0.0523 (4) | 0.0463 (4) | −0.0016 (4) | 0.0151 (3) | −0.0082 (3) |
N2 | 0.0781 (7) | 0.0670 (5) | 0.0439 (4) | 0.0001 (4) | 0.0124 (4) | −0.0035 (4) |
C1 | 0.0689 (7) | 0.0593 (6) | 0.0520 (5) | 0.0017 (5) | 0.0079 (5) | −0.0029 (4) |
C2 | 0.0657 (6) | 0.0521 (5) | 0.0443 (4) | −0.0066 (4) | 0.0155 (4) | −0.0079 (4) |
C3 | 0.0744 (7) | 0.0657 (6) | 0.0559 (5) | −0.0027 (5) | 0.0260 (5) | −0.0112 (5) |
C4 | 0.0701 (7) | 0.0626 (6) | 0.0771 (7) | 0.0061 (5) | 0.0240 (6) | −0.0058 (5) |
C5 | 0.0732 (7) | 0.0596 (6) | 0.0656 (6) | 0.0028 (5) | 0.0126 (5) | 0.0047 (5) |
C6 | 0.0724 (7) | 0.0567 (5) | 0.0459 (5) | −0.0053 (5) | 0.0144 (4) | −0.0025 (4) |
C7 | 0.0590 (6) | 0.0446 (4) | 0.0453 (4) | −0.0059 (4) | 0.0149 (4) | −0.0076 (3) |
C8 | 0.0633 (6) | 0.0573 (5) | 0.0552 (5) | −0.0036 (4) | 0.0231 (5) | −0.0097 (4) |
C9 | 0.0616 (6) | 0.0506 (5) | 0.0493 (5) | 0.0002 (4) | 0.0194 (4) | −0.0044 (4) |
N1—C1 | 1.3564 (13) | C8—C9 | 1.5138 (14) |
N1—C7 | 1.3772 (13) | C9—C9i | 1.5171 (13) |
N1—C8 | 1.4597 (13) | C1—H1 | 0.9300 |
N2—C1 | 1.3079 (14) | C3—H3 | 0.9300 |
N2—C2 | 1.3853 (13) | C4—H4 | 0.9300 |
C2—C3 | 1.3924 (15) | C5—H5 | 0.9300 |
C2—C7 | 1.4020 (13) | C6—H6 | 0.9300 |
C3—C4 | 1.3663 (16) | C8—H8A | 0.9700 |
C4—C5 | 1.3980 (17) | C8—H8B | 0.9700 |
C5—C6 | 1.3775 (16) | C9—H9A | 0.9700 |
C6—C7 | 1.3879 (14) | C9—H9B | 0.9700 |
N1···C4ii | 3.4006 (14) | H1···C5viii | 2.9100 |
N2···H9Biii | 2.9400 | H3···H9Aiv | 2.5400 |
N2···H6iv | 2.6900 | H4···C1vii | 2.7300 |
N2···H8Biv | 2.8000 | H6···C8 | 3.0200 |
C1···C3ii | 3.5147 (16) | H6···H8B | 2.5600 |
C1···C4v | 3.5961 (16) | H6···N2ix | 2.6900 |
C3···C1vi | 3.5147 (16) | H8A···H1 | 2.5800 |
C4···N1vi | 3.4006 (14) | H8A···H9Ai | 2.5400 |
C4···C1vii | 3.5961 (16) | H8B···C5ii | 3.0500 |
C5···C8vi | 3.5472 (15) | H8B···C6 | 2.9500 |
C8···C5ii | 3.5472 (15) | H8B···H6 | 2.5600 |
C1···H4v | 2.7300 | H8B···H9Bi | 2.4900 |
C2···H9Biii | 2.9100 | H8B···N2ix | 2.8000 |
C5···H8Bvi | 3.0500 | H9A···C7 | 3.0300 |
C5···H1iii | 2.9100 | H9A···H8Ai | 2.5400 |
C6···H8B | 2.9500 | H9A···H3ix | 2.5400 |
C7···H9A | 3.0300 | H9B···N2viii | 2.9400 |
C8···H6 | 3.0200 | H9B···C2viii | 2.9100 |
H1···H8A | 2.5800 | H9B···H8Bi | 2.4900 |
C1—N1—C7 | 106.30 (8) | C2—C3—H3 | 121.00 |
C1—N1—C8 | 127.13 (9) | C4—C3—H3 | 121.00 |
C7—N1—C8 | 126.24 (8) | C3—C4—H4 | 119.00 |
C1—N2—C2 | 103.98 (8) | C5—C4—H4 | 119.00 |
N1—C1—N2 | 114.40 (9) | C4—C5—H5 | 119.00 |
N2—C2—C3 | 130.29 (9) | C6—C5—H5 | 119.00 |
N2—C2—C7 | 110.27 (9) | C5—C6—H6 | 122.00 |
C3—C2—C7 | 119.44 (9) | C7—C6—H6 | 122.00 |
C2—C3—C4 | 118.04 (10) | N1—C8—H8A | 109.00 |
C3—C4—C5 | 121.88 (10) | N1—C8—H8B | 109.00 |
C4—C5—C6 | 121.46 (10) | C9—C8—H8A | 109.00 |
C5—C6—C7 | 116.36 (10) | C9—C8—H8B | 109.00 |
N1—C7—C2 | 105.04 (8) | H8A—C8—H8B | 108.00 |
N1—C7—C6 | 132.15 (9) | C8—C9—H9A | 109.00 |
C2—C7—C6 | 122.80 (9) | C8—C9—H9B | 109.00 |
N1—C8—C9 | 111.88 (9) | H9A—C9—H9B | 108.00 |
C8—C9—C9i | 111.96 (8) | C9i—C9—H9A | 109.00 |
N1—C1—H1 | 123.00 | C9i—C9—H9B | 109.00 |
N2—C1—H1 | 123.00 | ||
C7—N1—C1—N2 | 0.16 (12) | N2—C2—C7—C6 | −177.86 (9) |
C8—N1—C1—N2 | −173.59 (9) | N2—C2—C3—C4 | 178.38 (11) |
C8—N1—C7—C2 | 173.15 (9) | C7—C2—C3—C4 | −0.99 (15) |
C1—N1—C7—C6 | 177.99 (11) | C3—C2—C7—N1 | −179.56 (9) |
C8—N1—C7—C6 | −8.19 (16) | C3—C2—C7—C6 | 1.63 (15) |
C1—N1—C8—C9 | 92.02 (12) | C2—C3—C4—C5 | 0.03 (17) |
C7—N1—C8—C9 | −80.54 (11) | C3—C4—C5—C6 | 0.40 (17) |
C1—N1—C7—C2 | −0.66 (10) | C4—C5—C6—C7 | 0.17 (16) |
C2—N2—C1—N1 | 0.43 (12) | C5—C6—C7—C2 | −1.18 (15) |
C1—N2—C2—C3 | 179.74 (11) | C5—C6—C7—N1 | −179.64 (10) |
C1—N2—C2—C7 | −0.85 (12) | N1—C8—C9—C9i | 177.28 (8) |
N2—C2—C7—N1 | 0.96 (11) | C8—C9—C9i—C8i | 179.98 (10) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y, z; (iii) −x+1, y+1/2, −z+3/2; (iv) x, −y+1/2, z+1/2; (v) −x, y−1/2, −z+3/2; (vi) x−1, y, z; (vii) −x, y+1/2, −z+3/2; (viii) −x+1, y−1/2, −z+3/2; (ix) x, −y+1/2, z−1/2. |