Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803001235/ci6195sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803001235/ci6195Isup2.hkl |
CCDC reference: 192315
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.067
- wR factor = 0.196
- Data-to-parameter ratio = 15.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.100 PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(8) - C(12) = 1.43 Ang. PLAT_420 Alert C D-H Without Acceptor N(11) - H(11B) ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check
Refluxing a solution of 3-(4-dimethylaminophenyl)-1-(4-methoxyphenyl)-prop-2-en-1-one (0.5 g, 1.77 mmol), malononitrile (0.23 g, 3.48 mmol) and pyrrolidine (0.25 g, 3.52 mmol) in ethanol for 19 h gave the title compound. Single crystals were grown by slow evaporation of a solution in ethanol–ethylacetate (1:1). The melting point of the title compound is 491–493 K.
After checking their presence in the difference map, all H atoms were positioned geometrically and allowed to ride on their attached atoms using SHELXL97 (Sheldrick, 1997) defaults for bond lengths and displacement parameters. The high Rint value (0.1) and low ratio (0.3) of observed to unique reflections may be as a result of the poor diffraction quality of the crystal.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 35% probability level. | |
Fig. 2. The molecular packing, viewed down the a axis. |
C28H28N6O | Z = 2 |
Mr = 464.56 | F(000) = 492 |
Triclinic, P1 | Dx = 1.266 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54180 Å |
a = 10.671 (2) Å | Cell parameters from 25 reflections |
b = 10.974 (1) Å | θ = 10–35° |
c = 11.826 (2) Å | µ = 0.64 mm−1 |
α = 82.82 (1)° | T = 293 K |
β = 64.04 (1)° | Parallelepiped, yellow |
γ = 78.32 (1)° | 0.48 × 0.34 × 0.28 mm |
V = 1218.3 (3) Å3 |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.100 |
Radiation source: fine-focus sealed tube | θmax = 71.9°, θmin = 4.1° |
Graphite monochromator | h = −12→13 |
ω/2θ scans | k = 0→13 |
5192 measured reflections | l = −14→14 |
4789 independent reflections | 3 standard reflections every 200 reflections |
1438 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.196 | H-atom parameters constrained |
S = 0.90 | w = 1/[σ2(Fo2) + (0.0694P)2] where P = (Fo2 + 2Fc2)/3 |
4789 reflections | (Δ/σ)max < 0.001 |
319 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C28H28N6O | γ = 78.32 (1)° |
Mr = 464.56 | V = 1218.3 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.671 (2) Å | Cu Kα radiation |
b = 10.974 (1) Å | µ = 0.64 mm−1 |
c = 11.826 (2) Å | T = 293 K |
α = 82.82 (1)° | 0.48 × 0.34 × 0.28 mm |
β = 64.04 (1)° |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.100 |
5192 measured reflections | 3 standard reflections every 200 reflections |
4789 independent reflections | intensity decay: none |
1438 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.196 | H-atom parameters constrained |
S = 0.90 | Δρmax = 0.22 e Å−3 |
4789 reflections | Δρmin = −0.26 e Å−3 |
319 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | −0.1258 (4) | 0.3095 (4) | 0.3983 (4) | 0.0395 (11) | |
C2 | −0.0682 (5) | 0.2280 (5) | 0.3085 (5) | 0.0377 (13) | |
C3 | 0.0578 (5) | 0.1435 (5) | 0.2921 (5) | 0.0471 (15) | |
H3 | 0.0950 | 0.0862 | 0.2291 | 0.057* | |
C4 | 0.1256 (5) | 0.1444 (5) | 0.3667 (5) | 0.0396 (14) | |
C5 | 0.1185 (5) | 0.2460 (5) | 0.5528 (5) | 0.0476 (15) | |
N6 | 0.0516 (4) | 0.3237 (4) | 0.6466 (4) | 0.0461 (12) | |
C7 | −0.0733 (5) | 0.3979 (5) | 0.6606 (5) | 0.0393 (14) | |
C8 | −0.1323 (5) | 0.3958 (5) | 0.5763 (5) | 0.0413 (14) | |
C9 | −0.0623 (5) | 0.3109 (5) | 0.4767 (5) | 0.0389 (13) | |
C10 | 0.0656 (5) | 0.2302 (5) | 0.4630 (4) | 0.0353 (13) | |
N11 | 0.2410 (4) | 0.1791 (4) | 0.5484 (4) | 0.0754 (18) | |
H11A | 0.2698 | 0.1888 | 0.6037 | 0.091* | |
H11B | 0.2905 | 0.1267 | 0.4903 | 0.091* | |
C12 | −0.2571 (6) | 0.4760 (5) | 0.5797 (5) | 0.0441 (14) | |
N13 | −0.3585 (5) | 0.5369 (4) | 0.5805 (4) | 0.0650 (16) | |
N14 | −0.1300 (4) | 0.4681 (4) | 0.7612 (4) | 0.0453 (12) | |
C15 | −0.0572 (5) | 0.4688 (5) | 0.8414 (5) | 0.0502 (15) | |
H15A | 0.0350 | 0.4929 | 0.7929 | 0.060* | |
H15B | −0.0458 | 0.3875 | 0.8819 | 0.060* | |
C16 | −0.1536 (6) | 0.5640 (6) | 0.9369 (5) | 0.0670 (19) | |
H16A | −0.1533 | 0.5388 | 1.0184 | 0.080* | |
H16B | −0.1231 | 0.6444 | 0.9111 | 0.080* | |
C17 | −0.2976 (6) | 0.5709 (6) | 0.9436 (6) | 0.077 (2) | |
H17A | −0.3528 | 0.6532 | 0.9664 | 0.093* | |
H17B | −0.3472 | 0.5098 | 1.0049 | 0.093* | |
C18 | −0.2713 (5) | 0.5431 (5) | 0.8119 (5) | 0.0544 (16) | |
H18A | −0.3411 | 0.4969 | 0.8145 | 0.065* | |
H18B | −0.2744 | 0.6194 | 0.7614 | 0.065* | |
C19 | −0.1433 (5) | 0.2290 (5) | 0.2281 (5) | 0.0403 (13) | |
C20 | −0.2803 (5) | 0.2950 (5) | 0.2640 (5) | 0.0487 (15) | |
H20 | −0.3246 | 0.3376 | 0.3384 | 0.058* | |
C21 | −0.3494 (6) | 0.2968 (5) | 0.1899 (5) | 0.0550 (16) | |
H21 | −0.4408 | 0.3408 | 0.2149 | 0.066* | |
C22 | −0.2866 (6) | 0.2346 (5) | 0.0782 (5) | 0.0481 (15) | |
C23 | −0.1529 (6) | 0.1696 (5) | 0.0417 (5) | 0.0536 (16) | |
H23 | −0.1089 | 0.1275 | −0.0330 | 0.064* | |
C24 | −0.0831 (5) | 0.1669 (5) | 0.1174 (5) | 0.0515 (16) | |
H24 | 0.0077 | 0.1216 | 0.0925 | 0.062* | |
O25 | −0.3679 (4) | 0.2459 (4) | 0.0125 (4) | 0.0654 (12) | |
C26 | −0.3065 (6) | 0.1823 (6) | −0.1023 (5) | 0.084 (2) | |
H26A | −0.2186 | 0.2093 | −0.1572 | 0.126* | |
H26B | −0.3698 | 0.2005 | −0.1424 | 0.126* | |
H26C | −0.2900 | 0.0942 | −0.0848 | 0.126* | |
C27 | 0.2579 (5) | 0.0528 (5) | 0.3403 (4) | 0.0368 (13) | |
C28 | 0.2544 (5) | −0.0629 (5) | 0.4007 (5) | 0.0473 (15) | |
H28 | 0.1681 | −0.0825 | 0.4601 | 0.057* | |
C29 | 0.3749 (5) | −0.1511 (5) | 0.3763 (5) | 0.0464 (15) | |
H29 | 0.3678 | −0.2289 | 0.4177 | 0.056* | |
C30 | 0.5056 (5) | −0.1246 (5) | 0.2910 (5) | 0.0381 (13) | |
C31 | 0.5092 (5) | −0.0098 (5) | 0.2276 (6) | 0.0667 (19) | |
H31 | 0.5950 | 0.0094 | 0.1667 | 0.080* | |
C32 | 0.3872 (5) | 0.0773 (5) | 0.2532 (6) | 0.0649 (19) | |
H32 | 0.3933 | 0.1543 | 0.2100 | 0.078* | |
N33 | 0.6291 (4) | −0.2099 (4) | 0.2697 (4) | 0.0451 (12) | |
C34 | 0.7566 (5) | −0.1850 (5) | 0.1593 (5) | 0.072 (2) | |
H34A | 0.7421 | −0.1845 | 0.0847 | 0.108* | |
H34B | 0.8347 | −0.2487 | 0.1551 | 0.108* | |
H34C | 0.7768 | −0.1054 | 0.1658 | 0.108* | |
C35 | 0.6193 (6) | −0.3416 (5) | 0.2978 (5) | 0.0638 (18) | |
H35A | 0.5567 | −0.3536 | 0.3848 | 0.096* | |
H35B | 0.7114 | −0.3885 | 0.2816 | 0.096* | |
H35C | 0.5835 | −0.3694 | 0.2457 | 0.096* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.035 (2) | 0.038 (3) | 0.040 (3) | 0.001 (2) | −0.015 (2) | −0.003 (2) |
C2 | 0.030 (3) | 0.040 (3) | 0.038 (3) | 0.002 (3) | −0.012 (2) | −0.006 (3) |
C3 | 0.041 (3) | 0.050 (4) | 0.051 (4) | 0.005 (3) | −0.021 (3) | −0.019 (3) |
C4 | 0.033 (3) | 0.037 (3) | 0.045 (3) | 0.003 (3) | −0.014 (3) | −0.013 (3) |
C5 | 0.040 (3) | 0.044 (4) | 0.066 (4) | 0.001 (3) | −0.030 (3) | −0.011 (3) |
N6 | 0.043 (3) | 0.048 (3) | 0.052 (3) | 0.005 (2) | −0.026 (2) | −0.016 (2) |
C7 | 0.036 (3) | 0.033 (3) | 0.047 (3) | −0.005 (3) | −0.016 (3) | −0.002 (3) |
C8 | 0.033 (3) | 0.038 (3) | 0.046 (3) | 0.009 (3) | −0.014 (3) | −0.011 (3) |
C9 | 0.032 (3) | 0.042 (4) | 0.036 (3) | −0.006 (3) | −0.010 (2) | 0.002 (3) |
C10 | 0.031 (3) | 0.035 (3) | 0.039 (3) | 0.002 (2) | −0.016 (2) | −0.005 (3) |
N11 | 0.057 (3) | 0.091 (4) | 0.094 (4) | 0.033 (3) | −0.052 (3) | −0.058 (3) |
C12 | 0.046 (3) | 0.045 (4) | 0.038 (3) | −0.002 (3) | −0.015 (3) | −0.011 (3) |
N13 | 0.050 (3) | 0.079 (4) | 0.065 (3) | 0.022 (3) | −0.032 (3) | −0.025 (3) |
N14 | 0.041 (3) | 0.051 (3) | 0.048 (3) | 0.007 (2) | −0.024 (2) | −0.019 (2) |
C15 | 0.052 (3) | 0.044 (4) | 0.054 (4) | 0.004 (3) | −0.025 (3) | −0.013 (3) |
C16 | 0.072 (4) | 0.066 (5) | 0.067 (4) | −0.008 (4) | −0.030 (4) | −0.023 (4) |
C17 | 0.060 (4) | 0.095 (5) | 0.066 (4) | 0.022 (4) | −0.025 (3) | −0.025 (4) |
C18 | 0.054 (3) | 0.055 (4) | 0.046 (4) | 0.006 (3) | −0.017 (3) | −0.013 (3) |
C19 | 0.042 (3) | 0.035 (3) | 0.037 (3) | −0.007 (3) | −0.011 (3) | 0.000 (3) |
C20 | 0.044 (3) | 0.060 (4) | 0.044 (3) | 0.006 (3) | −0.023 (3) | −0.012 (3) |
C21 | 0.050 (4) | 0.062 (4) | 0.057 (4) | 0.007 (3) | −0.029 (3) | −0.018 (3) |
C22 | 0.055 (4) | 0.048 (4) | 0.049 (4) | −0.010 (3) | −0.030 (3) | 0.004 (3) |
C23 | 0.060 (4) | 0.061 (4) | 0.044 (3) | −0.008 (3) | −0.024 (3) | −0.012 (3) |
C24 | 0.038 (3) | 0.057 (4) | 0.054 (4) | 0.006 (3) | −0.015 (3) | −0.017 (3) |
O25 | 0.071 (3) | 0.082 (3) | 0.058 (3) | −0.008 (2) | −0.041 (2) | −0.009 (2) |
C26 | 0.088 (5) | 0.113 (6) | 0.067 (5) | −0.018 (5) | −0.042 (4) | −0.023 (4) |
C27 | 0.032 (3) | 0.039 (3) | 0.036 (3) | −0.007 (3) | −0.010 (2) | −0.005 (3) |
C28 | 0.030 (3) | 0.048 (4) | 0.050 (4) | −0.006 (3) | −0.004 (3) | −0.001 (3) |
C29 | 0.034 (3) | 0.043 (3) | 0.052 (3) | 0.004 (3) | −0.015 (3) | 0.005 (3) |
C30 | 0.030 (3) | 0.036 (3) | 0.046 (3) | −0.003 (3) | −0.014 (3) | −0.009 (3) |
C31 | 0.033 (3) | 0.047 (4) | 0.086 (5) | 0.004 (3) | −0.002 (3) | 0.008 (4) |
C32 | 0.039 (3) | 0.034 (4) | 0.092 (5) | −0.005 (3) | −0.004 (3) | 0.009 (3) |
N33 | 0.031 (2) | 0.045 (3) | 0.051 (3) | 0.003 (2) | −0.013 (2) | −0.004 (2) |
C34 | 0.046 (4) | 0.066 (4) | 0.077 (5) | 0.013 (3) | −0.009 (3) | −0.007 (4) |
C35 | 0.058 (4) | 0.048 (4) | 0.085 (5) | 0.004 (3) | −0.034 (4) | −0.007 (3) |
N1—C2 | 1.322 (5) | C19—C20 | 1.395 (6) |
N1—C9 | 1.370 (6) | C20—C21 | 1.367 (6) |
C2—C3 | 1.420 (6) | C20—H20 | 0.93 |
C2—C19 | 1.486 (6) | C21—C22 | 1.387 (7) |
C3—C4 | 1.366 (6) | C21—H21 | 0.93 |
C3—H3 | 0.93 | C22—C23 | 1.363 (6) |
C4—C10 | 1.407 (6) | C22—O25 | 1.376 (6) |
C4—C27 | 1.490 (6) | C23—C24 | 1.387 (7) |
C5—N6 | 1.329 (6) | C23—H23 | 0.93 |
C5—N11 | 1.346 (6) | C24—H24 | 0.93 |
C5—C10 | 1.445 (7) | O25—C26 | 1.427 (6) |
N6—C7 | 1.367 (6) | C26—H26A | 0.96 |
C7—N14 | 1.336 (6) | C26—H26B | 0.96 |
C7—C8 | 1.399 (6) | C26—H26C | 0.96 |
C8—C12 | 1.426 (7) | C27—C32 | 1.369 (6) |
C8—C9 | 1.427 (6) | C27—C28 | 1.376 (6) |
C9—C10 | 1.423 (6) | C28—C29 | 1.383 (6) |
N11—H11A | 0.86 | C28—H28 | 0.93 |
N11—H11B | 0.86 | C29—C30 | 1.380 (6) |
C12—N13 | 1.148 (6) | C29—H29 | 0.93 |
N14—C18 | 1.463 (6) | C30—C31 | 1.382 (6) |
N14—C15 | 1.466 (6) | C30—N33 | 1.395 (5) |
C15—C16 | 1.506 (6) | C31—C32 | 1.387 (6) |
C15—H15A | 0.97 | C31—H31 | 0.93 |
C15—H15B | 0.97 | C32—H32 | 0.93 |
C16—C17 | 1.490 (7) | N33—C35 | 1.456 (6) |
C16—H16A | 0.97 | N33—C34 | 1.461 (6) |
C16—H16B | 0.97 | C34—H34A | 0.96 |
C17—C18 | 1.517 (7) | C34—H34B | 0.96 |
C17—H17A | 0.97 | C34—H34C | 0.96 |
C17—H17B | 0.97 | C35—H35A | 0.96 |
C18—H18A | 0.97 | C35—H35B | 0.96 |
C18—H18B | 0.97 | C35—H35C | 0.96 |
C19—C24 | 1.378 (6) | ||
C2—N1—C9 | 118.8 (4) | C24—C19—C2 | 122.7 (5) |
N1—C2—C3 | 121.1 (5) | C20—C19—C2 | 119.7 (5) |
N1—C2—C19 | 116.5 (4) | C21—C20—C19 | 119.9 (5) |
C3—C2—C19 | 122.4 (5) | C21—C20—H20 | 120.0 |
C4—C3—C2 | 121.5 (5) | C19—C20—H20 | 120.0 |
C4—C3—H3 | 119.2 | C20—C21—C22 | 121.7 (5) |
C2—C3—H3 | 119.2 | C20—C21—H21 | 119.2 |
C3—C4—C10 | 118.1 (4) | C22—C21—H21 | 119.2 |
C3—C4—C27 | 117.1 (4) | C23—C22—O25 | 125.5 (5) |
C10—C4—C27 | 124.8 (5) | C23—C22—C21 | 119.2 (5) |
N6—C5—N11 | 114.5 (5) | O25—C22—C21 | 115.3 (5) |
N6—C5—C10 | 124.0 (5) | C22—C23—C24 | 119.2 (5) |
N11—C5—C10 | 121.5 (5) | C22—C23—H23 | 120.4 |
C5—N6—C7 | 120.2 (5) | C24—C23—H23 | 120.4 |
N14—C7—N6 | 113.3 (5) | C19—C24—C23 | 122.5 (5) |
N14—C7—C8 | 125.4 (5) | C19—C24—H24 | 118.8 |
N6—C7—C8 | 121.3 (5) | C23—C24—H24 | 118.8 |
C7—C8—C12 | 124.6 (5) | C22—O25—C26 | 116.6 (4) |
C7—C8—C9 | 118.7 (5) | O25—C26—H26A | 109.5 |
C12—C8—C9 | 116.7 (5) | O25—C26—H26B | 109.5 |
N1—C9—C10 | 122.5 (5) | H26A—C26—H26B | 109.5 |
N1—C9—C8 | 116.8 (4) | O25—C26—H26C | 109.5 |
C10—C9—C8 | 120.7 (5) | H26A—C26—H26C | 109.5 |
C4—C10—C9 | 117.9 (5) | H26B—C26—H26C | 109.5 |
C4—C10—C5 | 127.2 (4) | C32—C27—C28 | 116.8 (5) |
C9—C10—C5 | 114.9 (5) | C32—C27—C4 | 122.2 (5) |
C5—N11—H11A | 120.0 | C28—C27—C4 | 120.9 (5) |
C5—N11—H11B | 120.0 | C27—C28—C29 | 122.3 (5) |
H11A—N11—H11B | 120.0 | C27—C28—H28 | 118.8 |
N13—C12—C8 | 177.3 (6) | C29—C28—H28 | 118.8 |
C7—N14—C18 | 126.4 (5) | C30—C29—C28 | 120.6 (5) |
C7—N14—C15 | 121.7 (4) | C30—C29—H29 | 119.7 |
C18—N14—C15 | 111.7 (4) | C28—C29—H29 | 119.7 |
N14—C15—C16 | 103.7 (4) | C29—C30—C31 | 117.2 (5) |
N14—C15—H15A | 111.0 | C29—C30—N33 | 121.6 (5) |
C16—C15—H15A | 111.0 | C31—C30—N33 | 121.2 (5) |
N14—C15—H15B | 111.0 | C30—C31—C32 | 121.2 (5) |
C16—C15—H15B | 111.0 | C30—C31—H31 | 119.4 |
H15A—C15—H15B | 109.0 | C32—C31—H31 | 119.4 |
C17—C16—C15 | 106.4 (5) | C27—C32—C31 | 121.7 (5) |
C17—C16—H16A | 110.4 | C27—C32—H32 | 119.1 |
C15—C16—H16A | 110.4 | C31—C32—H32 | 119.1 |
C17—C16—H16B | 110.4 | C30—N33—C35 | 118.7 (4) |
C15—C16—H16B | 110.4 | C30—N33—C34 | 116.9 (4) |
H16A—C16—H16B | 108.6 | C35—N33—C34 | 114.2 (4) |
C16—C17—C18 | 104.4 (5) | N33—C34—H34A | 109.5 |
C16—C17—H17A | 110.9 | N33—C34—H34B | 109.5 |
C18—C17—H17A | 110.9 | H34A—C34—H34B | 109.5 |
C16—C17—H17B | 110.9 | N33—C34—H34C | 109.5 |
C18—C17—H17B | 110.9 | H34A—C34—H34C | 109.5 |
H17A—C17—H17B | 108.9 | H34B—C34—H34C | 109.5 |
N14—C18—C17 | 104.3 (4) | N33—C35—H35A | 109.5 |
N14—C18—H18A | 110.9 | N33—C35—H35B | 109.5 |
C17—C18—H18A | 110.9 | H35A—C35—H35B | 109.5 |
N14—C18—H18B | 110.9 | N33—C35—H35C | 109.5 |
C17—C18—H18B | 110.9 | H35A—C35—H35C | 109.5 |
H18A—C18—H18B | 108.9 | H35B—C35—H35C | 109.5 |
C24—C19—C20 | 117.6 (5) | ||
C9—N1—C2—C3 | −0.5 (7) | C15—C16—C17—C18 | −31.4 (6) |
C9—N1—C2—C19 | 178.8 (5) | C7—N14—C18—C17 | 163.6 (5) |
N1—C2—C3—C4 | −1.1 (8) | C15—N14—C18—C17 | −11.3 (6) |
C19—C2—C3—C4 | 179.7 (5) | C16—C17—C18—N14 | 25.9 (6) |
C2—C3—C4—C10 | 1.3 (8) | N1—C2—C19—C24 | 167.4 (5) |
C2—C3—C4—C27 | −179.3 (5) | C3—C2—C19—C24 | −13.4 (8) |
N11—C5—N6—C7 | 179.3 (5) | N1—C2—C19—C20 | −12.5 (7) |
C10—C5—N6—C7 | −2.0 (8) | C3—C2—C19—C20 | 166.7 (5) |
C5—N6—C7—N14 | 178.0 (5) | C24—C19—C20—C21 | −0.3 (8) |
C5—N6—C7—C8 | −1.1 (8) | C2—C19—C20—C21 | 179.6 (5) |
N14—C7—C8—C12 | 5.2 (9) | C19—C20—C21—C22 | −0.2 (9) |
N6—C7—C8—C12 | −175.7 (5) | C20—C21—C22—C23 | 0.3 (9) |
N14—C7—C8—C9 | −176.8 (5) | C20—C21—C22—O25 | −179.2 (5) |
N6—C7—C8—C9 | 2.3 (8) | O25—C22—C23—C24 | 179.6 (5) |
C2—N1—C9—C10 | 1.8 (7) | C21—C22—C23—C24 | 0.2 (9) |
C2—N1—C9—C8 | −176.7 (5) | C20—C19—C24—C23 | 0.8 (8) |
C7—C8—C9—N1 | 178.3 (5) | C2—C19—C24—C23 | −179.1 (5) |
C12—C8—C9—N1 | −3.6 (7) | C22—C23—C24—C19 | −0.8 (9) |
C7—C8—C9—C10 | −0.3 (8) | C23—C22—O25—C26 | 0.9 (8) |
C12—C8—C9—C10 | 177.9 (5) | C21—C22—O25—C26 | −179.6 (5) |
C3—C4—C10—C9 | 0.0 (7) | C3—C4—C27—C32 | 86.5 (7) |
C27—C4—C10—C9 | −179.4 (5) | C10—C4—C27—C32 | −94.1 (7) |
C3—C4—C10—C5 | 179.3 (6) | C3—C4—C27—C28 | −91.5 (6) |
C27—C4—C10—C5 | 0.0 (9) | C10—C4—C27—C28 | 87.8 (7) |
N1—C9—C10—C4 | −1.6 (8) | C32—C27—C28—C29 | 0.3 (8) |
C8—C9—C10—C4 | 176.9 (5) | C4—C27—C28—C29 | 178.5 (5) |
N1—C9—C10—C5 | 179.0 (5) | C27—C28—C29—C30 | 1.6 (8) |
C8—C9—C10—C5 | −2.5 (7) | C28—C29—C30—C31 | −3.2 (8) |
N6—C5—C10—C4 | −175.6 (6) | C28—C29—C30—N33 | 176.8 (5) |
N11—C5—C10—C4 | 3.0 (9) | C29—C30—C31—C32 | 3.0 (9) |
N6—C5—C10—C9 | 3.8 (8) | N33—C30—C31—C32 | −176.9 (5) |
N11—C5—C10—C9 | −177.6 (5) | C28—C27—C32—C31 | −0.5 (9) |
N6—C7—N14—C18 | −170.6 (5) | C4—C27—C32—C31 | −178.7 (6) |
C8—C7—N14—C18 | 8.5 (9) | C30—C31—C32—C27 | −1.2 (10) |
N6—C7—N14—C15 | 3.8 (7) | C29—C30—N33—C35 | 23.6 (7) |
C8—C7—N14—C15 | −177.0 (5) | C31—C30—N33—C35 | −156.5 (5) |
C7—N14—C15—C16 | 177.1 (5) | C29—C30—N33—C34 | 166.9 (5) |
C18—N14—C15—C16 | −7.8 (6) | C31—C30—N33—C34 | −13.2 (7) |
N14—C15—C16—C17 | 24.3 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11A···N33i | 0.86 | 2.25 | 3.106 (6) | 173 |
Symmetry code: (i) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C28H28N6O |
Mr | 464.56 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 10.671 (2), 10.974 (1), 11.826 (2) |
α, β, γ (°) | 82.82 (1), 64.04 (1), 78.32 (1) |
V (Å3) | 1218.3 (3) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 0.64 |
Crystal size (mm) | 0.48 × 0.34 × 0.28 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5192, 4789, 1438 |
Rint | 0.100 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.196, 0.90 |
No. of reflections | 4789 |
No. of parameters | 319 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.26 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990), SHELXL97 and PARST (Nardelli, 1995).
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Naphthyridine derivatives have a wide range of biological activities, such as anti-inflammatory, anticonvulsant (Balogh et al., 1986), insecticidal (Takeuchi & Hamada, 1975), antitumour (El-Subbagh et al., 1999), tuberculostatic (Ferrarini et al., 1998), cardiotonic (Mohan & Mishra, 1997) and antibacterial (Datta et al., 1995). They have been reported as potential drugs for the treatment of bladder function disorders (Natsugari et al., 1999). The naphthyridine derivatives also act as dyes (Irikawa & Iijima, 1998). Since naphthyridine derivatives come under the class of heterocyclic compounds, it is expected that they possess laser and non-linear optical properties (Lowe, 1984; Shanmugasundaram et al., 1993; Murugan et al., 1998). 1,6-Naphthyridine derivatives have been tested pharmacologically as antagonists at adrenoreceptors (Brown et al., 1993) and are also used as novel potent adenosine 3',5'-cyclic phosphate phosphodiesterase III inhibitors (Singh et al., 1995). The structure analysis of the title compound, (I), was carried out as part of our studies on 1,6-naphthyridine derivatives (Sankaranarayanan et al., 1999, 2001; Govindasamy et al., 2000).
The five rings of the molecules are identified as A (C5/N6/C7–C10), B (N1/C2–C4/C10/C9), C (C19–C24), D (N14/C15–C18) and E (C27–C32). The pyrrolidine ring adopts a half-chair conformation, which was confirmed using ring-puckering parameters (Cremer & Pople, 1975); q2 = 0.296 (6) Å and ϕ = 93.2 (9)°, and the asymmetry parameters ΔC2(N14) = 0.009 (2) (Nardelli, 1983). The naphthyridine moiety is planar with the fused pyridine rings (rings A and B) form a dihedral angle of 2.9 (1)°. The mean planes passing through phenyl rings C and E make diheral angles of 12.7 (1) and 87.0 (2)°, respectively, with ring B. The best plane through the pyrrolidine ring (D) makes a dihedral angle of 13.7 (4)° with the pyridine ring (A). The orientation of the substituents on the 1,6-naphthyridine ring may be determined by using the the following torsion angels at C2, C4 and C7: N1—C2—C19—C20 [−12.5 (7)°], C3—C2—C19—C24 [−13.4 (8)°], C3—C4—C27—C28 [−91.5 (6)°], C10—C4—C27—C32 [−94.1 (7)°], N6—C7—N14—C15 [3.8 (7)°] and C8—C7—N14—C18 [8.5 (9)°]. Methoxy group is coplanar [C21—C22—O25—C26 = −179.6 (5)°] with the attched phenyl ring (C).
The bond distances and angles are comparable with the related structures studied previously (Chinnakali et al., 1998; Sankaranarayanan et al., 1999, 2001; Govindasamy et al., 2000; Thirumurugan et al., 1999). The bond distance C5—N11 [1.346 (6) Å] is shorter than the typical C—N single bond distance (1.47 Å) as in the other related strucutres, indicating conjugation of the amino group with the aromatic naphthyridine moiety. The sum of the bond angles around atom N14 is 359.8 (4)°, indicating sp2 hybridization. The sum of the bond angles around atom N33 is 349.8 (4)°, indicating pyramidalization. The cyano bond distance C12—N13 [1.148 (6) Å] and the angle C8—C12—N13 [177.3 (6)°] are comparable with the related structures. Due to steric interactions, the bond angles C4—C10—C5 [127.2 (4)°], C8—C7—N14 [125.4 (5)°] and C3—C2—C19 [122.4 (5)°] are widened from 120°, while angles N1—C9—C8 [116.8 (4)°], N14—C7—N6 [113.3 (5)°] and N1—C2—C19 [116.5 (4)°] are narrowed from 120°.
One of the amino H atoms, H11B, is involved in an intramolecular N—H···π interaction [N11—H11B = 0.86 Å, H11B···Cg(E) = 2.63 Å, N11···Cg(E) = 3.470 (3) Å and N11—H11B···Cg(E) = 166°, where Cg(E) is the centroid of ring E]. The other H atom, H11A, is involved in the formation of centrosymmetrically hydrogen-bonded (N11—H11A···N33) dimers in the solid state [N11—H11A = 0.86 Å, H11A···N33i = 2.25 Å, N11···N33i = 3.106 (6) Å and N11—H11A···N33i = 173°; symmetry code: (i) 1 − x, −y, 1 − z]. The B ring of the molecules at (x, y, z) and E ring of the molecules at (-x, −y, 1 − z) are arranged in a face-to-edge manner, with their centroids separated by 4.741 (3) Å. Apart from these interactions, the molecular packing is stablized by weak C—H···π interactions [C28—H28 = 0.93 Å, H28···Cg(A) = 2.58 Å, C28···Cg(A) = 3.443 (6) Å and C28—H28···Cg(A) = 155°, where Cg(A) is the centroid of ring A at (-x, −y, 1 − z)].