Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058953/xu2353sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058953/xu2353Isup2.hkl |
CCDC reference: 665647
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.113
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general background, see: Franzen (2000); Gelen et al. (2003); Hu et al. (2001); Kong et al. (2004); Krchna & Holladay (2002); Phoon & Sim (2002).
A mixture of 1-pyridin-2-yl-ethanone (0.02 mol) and pyridine-2-carbaldehyde (0.01 mol) and sodium hydroxide (0.034 mol) in ethanol (30 ml) was stirred at 293 K for 3 h. The hydrochloric acid solution (0.05 M) was dropped into the above solution to pH = 6 to get the title compound (1.0 g, yield 30%). Single crystals were obtained by recrystallization from an ethanol solution at room temperature.
H atoms were positioned geometrically and allowed to ride on their parent atoms with C—H = 0.93–0.98 Å, Uiso(H) = 1.2Ueq(C).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).
Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. |
C20H17N3O2 | Z = 2 |
Mr = 331.37 | F(000) = 348 |
Triclinic, P1 | Dx = 1.314 Mg m−3 |
Hall symbol: -P 1 | Melting point: 124 K |
a = 8.3830 (17) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.750 (2) Å | Cell parameters from 25 reflections |
c = 10.950 (2) Å | θ = 4–14° |
α = 101.92 (3)° | µ = 0.09 mm−1 |
β = 104.71 (3)° | T = 295 K |
γ = 111.51 (3)° | Block, colourless |
V = 837.3 (3) Å3 | 0.20 × 0.15 × 0.11 mm |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.018 |
Radiation source: fine-focus sealed tube | θmax = 25.5°, θmin = 2.0° |
Graphite monochromator | h = −10→9 |
ω/2θ scans | k = −7→13 |
4623 measured reflections | l = −13→13 |
3084 independent reflections | 3 standard reflections every 100 reflections |
2353 reflections with I > 2σ(I) | intensity decay: 0.1% |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0477P)2 + 0.1482P] where P = (Fo2 + 2Fc2)/3 |
3084 reflections | (Δ/σ)max < 0.001 |
226 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C20H17N3O2 | γ = 111.51 (3)° |
Mr = 331.37 | V = 837.3 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.3830 (17) Å | Mo Kα radiation |
b = 10.750 (2) Å | µ = 0.09 mm−1 |
c = 10.950 (2) Å | T = 295 K |
α = 101.92 (3)° | 0.20 × 0.15 × 0.11 mm |
β = 104.71 (3)° |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.018 |
4623 measured reflections | 3 standard reflections every 100 reflections |
3084 independent reflections | intensity decay: 0.1% |
2353 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.13 e Å−3 |
3084 reflections | Δρmin = −0.21 e Å−3 |
226 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 | ||
O1 | 0.57178 (18) | −0.27893 (12) | 0.07393 (13) | 0.0640 (4) | |
O2 | 0.78779 (19) | 0.19726 (12) | 0.04347 (12) | 0.0612 (4) | |
N1 | 0.41992 (19) | −0.30815 (15) | 0.34078 (14) | 0.0560 (4) | |
N2 | 0.8417 (2) | 0.45083 (15) | 0.32752 (14) | 0.0557 (4) | |
N3 | 0.97442 (18) | 0.09329 (14) | 0.36515 (13) | 0.0478 (3) | |
C1 | 0.3457 (3) | −0.4064 (2) | 0.3933 (2) | 0.0721 (6) | |
H1B | 0.3208 | −0.3782 | 0.4697 | 0.087* | |
C2 | 0.3047 (3) | −0.5456 (2) | 0.3409 (3) | 0.0811 (7) | |
H2B | 0.2529 | −0.6102 | 0.3810 | 0.097* | |
C3 | 0.3399 (3) | −0.5888 (2) | 0.2301 (3) | 0.0846 (7) | |
H3B | 0.3126 | −0.6835 | 0.1927 | 0.101* | |
C4 | 0.4162 (3) | −0.49125 (19) | 0.1741 (2) | 0.0672 (5) | |
H4A | 0.4424 | −0.5181 | 0.0980 | 0.081* | |
C5 | 0.4536 (2) | −0.35289 (16) | 0.23193 (16) | 0.0453 (4) | |
C6 | 0.5366 (2) | −0.24400 (16) | 0.17207 (16) | 0.0440 (4) | |
C7 | 0.5694 (2) | −0.09482 (16) | 0.23362 (16) | 0.0423 (4) | |
H7A | 0.6284 | −0.0657 | 0.3300 | 0.051* | |
H7B | 0.4520 | −0.0912 | 0.2152 | 0.051* | |
C8 | 0.6889 (2) | 0.00837 (15) | 0.18096 (15) | 0.0383 (3) | |
H8A | 0.6417 | −0.0323 | 0.0831 | 0.046* | |
C9 | 0.8847 (2) | 0.02844 (14) | 0.23367 (14) | 0.0360 (3) | |
C10 | 0.9652 (2) | −0.01886 (17) | 0.15183 (16) | 0.0453 (4) | |
H10A | 0.8993 | −0.0647 | 0.0605 | 0.054* | |
C11 | 1.1434 (2) | 0.00199 (19) | 0.20588 (19) | 0.0542 (4) | |
H11A | 1.2002 | −0.0286 | 0.1516 | 0.065* | |
C12 | 1.2357 (2) | 0.06803 (18) | 0.34003 (19) | 0.0555 (5) | |
H12A | 1.3565 | 0.0834 | 0.3795 | 0.067* | |
C13 | 1.1469 (2) | 0.11107 (19) | 0.41502 (18) | 0.0544 (4) | |
H13A | 1.2104 | 0.1557 | 0.5068 | 0.065* | |
C14 | 0.6836 (2) | 0.15105 (16) | 0.21789 (16) | 0.0433 (4) | |
H14A | 0.5566 | 0.1351 | 0.1969 | 0.052* | |
H14B | 0.7474 | 0.1990 | 0.3136 | 0.052* | |
C15 | 0.7697 (2) | 0.24470 (16) | 0.14624 (15) | 0.0417 (4) | |
C16 | 0.8333 (2) | 0.40088 (16) | 0.20360 (15) | 0.0416 (4) | |
C17 | 0.8833 (3) | 0.48560 (18) | 0.12857 (18) | 0.0564 (5) | |
H17A | 0.8748 | 0.4463 | 0.0418 | 0.068* | |
C18 | 0.9460 (3) | 0.62891 (19) | 0.1835 (2) | 0.0691 (6) | |
H18A | 0.9799 | 0.6887 | 0.1347 | 0.083* | |
C19 | 0.9575 (3) | 0.68178 (19) | 0.3110 (2) | 0.0690 (6) | |
H19A | 0.9998 | 0.7787 | 0.3511 | 0.083* | |
C20 | 0.9062 (3) | 0.59109 (19) | 0.3790 (2) | 0.0690 (6) | |
H20A | 0.9167 | 0.6290 | 0.4667 | 0.083* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0827 (9) | 0.0397 (7) | 0.0708 (9) | 0.0201 (6) | 0.0441 (7) | 0.0133 (6) |
O2 | 0.0957 (10) | 0.0497 (7) | 0.0500 (7) | 0.0367 (7) | 0.0365 (7) | 0.0185 (6) |
N1 | 0.0529 (9) | 0.0523 (9) | 0.0566 (9) | 0.0150 (7) | 0.0204 (7) | 0.0205 (7) |
N2 | 0.0775 (10) | 0.0419 (8) | 0.0516 (9) | 0.0264 (7) | 0.0299 (8) | 0.0148 (7) |
N3 | 0.0463 (8) | 0.0487 (8) | 0.0425 (8) | 0.0206 (6) | 0.0123 (6) | 0.0094 (6) |
C1 | 0.0720 (13) | 0.0758 (15) | 0.0686 (13) | 0.0214 (11) | 0.0322 (11) | 0.0367 (11) |
C2 | 0.0843 (15) | 0.0638 (14) | 0.0990 (18) | 0.0202 (12) | 0.0395 (14) | 0.0501 (13) |
C3 | 0.1021 (18) | 0.0452 (11) | 0.1096 (19) | 0.0241 (12) | 0.0468 (15) | 0.0376 (12) |
C4 | 0.0813 (14) | 0.0426 (10) | 0.0817 (14) | 0.0249 (10) | 0.0372 (11) | 0.0238 (10) |
C5 | 0.0383 (8) | 0.0394 (9) | 0.0525 (10) | 0.0130 (7) | 0.0130 (7) | 0.0162 (7) |
C6 | 0.0394 (8) | 0.0369 (8) | 0.0507 (10) | 0.0137 (7) | 0.0159 (7) | 0.0116 (7) |
C7 | 0.0408 (8) | 0.0378 (8) | 0.0492 (9) | 0.0171 (7) | 0.0183 (7) | 0.0145 (7) |
C8 | 0.0416 (8) | 0.0340 (8) | 0.0394 (8) | 0.0174 (7) | 0.0143 (7) | 0.0113 (6) |
C9 | 0.0417 (8) | 0.0261 (7) | 0.0396 (8) | 0.0133 (6) | 0.0156 (7) | 0.0122 (6) |
C10 | 0.0515 (9) | 0.0423 (9) | 0.0436 (9) | 0.0210 (8) | 0.0204 (7) | 0.0133 (7) |
C11 | 0.0514 (10) | 0.0532 (10) | 0.0703 (12) | 0.0281 (9) | 0.0328 (9) | 0.0222 (9) |
C12 | 0.0428 (9) | 0.0536 (10) | 0.0694 (12) | 0.0219 (8) | 0.0165 (9) | 0.0226 (9) |
C13 | 0.0492 (10) | 0.0532 (10) | 0.0482 (10) | 0.0195 (8) | 0.0070 (8) | 0.0114 (8) |
C14 | 0.0481 (9) | 0.0390 (8) | 0.0500 (9) | 0.0231 (7) | 0.0212 (7) | 0.0175 (7) |
C15 | 0.0473 (9) | 0.0408 (9) | 0.0398 (9) | 0.0233 (7) | 0.0138 (7) | 0.0143 (7) |
C16 | 0.0464 (9) | 0.0387 (8) | 0.0425 (9) | 0.0211 (7) | 0.0155 (7) | 0.0153 (7) |
C17 | 0.0724 (12) | 0.0475 (10) | 0.0527 (10) | 0.0242 (9) | 0.0280 (9) | 0.0210 (8) |
C18 | 0.0915 (15) | 0.0420 (10) | 0.0781 (14) | 0.0245 (10) | 0.0367 (12) | 0.0298 (10) |
C19 | 0.0864 (15) | 0.0355 (10) | 0.0810 (14) | 0.0229 (10) | 0.0340 (12) | 0.0145 (10) |
C20 | 0.1003 (16) | 0.0443 (11) | 0.0637 (12) | 0.0304 (11) | 0.0393 (11) | 0.0116 (9) |
O1—C6 | 1.2078 (19) | C8—C14 | 1.523 (2) |
O2—C15 | 1.2066 (18) | C8—H8A | 0.9800 |
N1—C5 | 1.329 (2) | C9—C10 | 1.374 (2) |
N1—C1 | 1.336 (2) | C10—C11 | 1.372 (2) |
N2—C16 | 1.325 (2) | C10—H10A | 0.9300 |
N2—C20 | 1.334 (2) | C11—C12 | 1.360 (3) |
N3—C9 | 1.332 (2) | C11—H11A | 0.9300 |
N3—C13 | 1.334 (2) | C12—C13 | 1.360 (2) |
C1—C2 | 1.362 (3) | C12—H12A | 0.9300 |
C1—H1B | 0.9300 | C13—H13A | 0.9300 |
C2—C3 | 1.351 (3) | C14—C15 | 1.494 (2) |
C2—H2B | 0.9300 | C14—H14A | 0.9700 |
C3—C4 | 1.364 (3) | C14—H14B | 0.9700 |
C3—H3B | 0.9300 | C15—C16 | 1.495 (2) |
C4—C5 | 1.371 (2) | C16—C17 | 1.373 (2) |
C4—H4A | 0.9300 | C17—C18 | 1.369 (2) |
C5—C6 | 1.495 (2) | C17—H17A | 0.9300 |
C6—C7 | 1.496 (2) | C18—C19 | 1.358 (3) |
C7—C8 | 1.520 (2) | C18—H18A | 0.9300 |
C7—H7A | 0.9700 | C19—C20 | 1.358 (3) |
C7—H7B | 0.9700 | C19—H19A | 0.9300 |
C8—C9 | 1.510 (2) | C20—H20A | 0.9300 |
C5—N1—C1 | 116.29 (17) | C11—C10—C9 | 119.52 (16) |
C16—N2—C20 | 116.38 (15) | C11—C10—H10A | 120.2 |
C9—N3—C13 | 117.34 (14) | C9—C10—H10A | 120.2 |
N1—C1—C2 | 123.4 (2) | C12—C11—C10 | 118.97 (16) |
N1—C1—H1B | 118.3 | C12—C11—H11A | 120.5 |
C2—C1—H1B | 118.3 | C10—C11—H11A | 120.5 |
C3—C2—C1 | 119.29 (19) | C13—C12—C11 | 118.30 (16) |
C3—C2—H2B | 120.4 | C13—C12—H12A | 120.9 |
C1—C2—H2B | 120.4 | C11—C12—H12A | 120.9 |
C2—C3—C4 | 118.8 (2) | N3—C13—C12 | 124.06 (17) |
C2—C3—H3B | 120.6 | N3—C13—H13A | 118.0 |
C4—C3—H3B | 120.6 | C12—C13—H13A | 118.0 |
C3—C4—C5 | 118.7 (2) | C15—C14—C8 | 112.94 (13) |
C3—C4—H4A | 120.6 | C15—C14—H14A | 109.0 |
C5—C4—H4A | 120.6 | C8—C14—H14A | 109.0 |
N1—C5—C4 | 123.38 (16) | C15—C14—H14B | 109.0 |
N1—C5—C6 | 116.83 (14) | C8—C14—H14B | 109.0 |
C4—C5—C6 | 119.79 (16) | H14A—C14—H14B | 107.8 |
O1—C6—C5 | 119.43 (14) | O2—C15—C14 | 121.65 (14) |
O1—C6—C7 | 121.65 (14) | O2—C15—C16 | 119.61 (14) |
C5—C6—C7 | 118.90 (14) | C14—C15—C16 | 118.74 (13) |
C6—C7—C8 | 112.50 (13) | N2—C16—C17 | 123.20 (15) |
C6—C7—H7A | 109.1 | N2—C16—C15 | 117.27 (14) |
C8—C7—H7A | 109.1 | C17—C16—C15 | 119.52 (14) |
C6—C7—H7B | 109.1 | C18—C17—C16 | 118.98 (17) |
C8—C7—H7B | 109.1 | C18—C17—H17A | 120.5 |
H7A—C7—H7B | 107.8 | C16—C17—H17A | 120.5 |
C9—C8—C7 | 110.17 (12) | C19—C18—C17 | 118.47 (18) |
C9—C8—C14 | 110.11 (13) | C19—C18—H18A | 120.8 |
C7—C8—C14 | 111.77 (12) | C17—C18—H18A | 120.8 |
C9—C8—H8A | 108.2 | C20—C19—C18 | 119.05 (17) |
C7—C8—H8A | 108.2 | C20—C19—H19A | 120.5 |
C14—C8—H8A | 108.2 | C18—C19—H19A | 120.5 |
N3—C9—C10 | 121.81 (14) | N2—C20—C19 | 123.91 (18) |
N3—C9—C8 | 115.90 (13) | N2—C20—H20A | 118.0 |
C10—C9—C8 | 122.28 (14) | C19—C20—H20A | 118.0 |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O1i | 0.93 | 2.51 | 3.322 (3) | 146 |
C11—H11A···O2ii | 0.93 | 2.55 | 3.415 (2) | 155 |
C14—H14B···N2 | 0.97 | 2.48 | 2.836 (2) | 101 |
C14—H14B···N3 | 0.97 | 2.56 | 2.908 (2) | 101 |
Symmetry codes: (i) −x+1, −y−1, −z; (ii) −x+2, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C20H17N3O2 |
Mr | 331.37 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 8.3830 (17), 10.750 (2), 10.950 (2) |
α, β, γ (°) | 101.92 (3), 104.71 (3), 111.51 (3) |
V (Å3) | 837.3 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.20 × 0.15 × 0.11 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4623, 3084, 2353 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.113, 1.04 |
No. of reflections | 3084 |
No. of parameters | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.13, −0.21 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1990), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O1i | 0.93 | 2.51 | 3.322 (3) | 145.5 |
C11—H11A···O2ii | 0.93 | 2.55 | 3.415 (2) | 154.9 |
C14—H14B···N2 | 0.97 | 2.48 | 2.836 (2) | 101.1 |
C14—H14B···N3 | 0.97 | 2.56 | 2.908 (2) | 101.3 |
Symmetry codes: (i) −x+1, −y−1, −z; (ii) −x+2, −y, −z. |
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In the previous research on Dracena cochinchinensit, we found that chalcone and it derivative have significant antifungal activities (Hu et al., 2001). They are important constituents commonly existing in biologically active natural products and synthetic compounds of medicinal interest (Kong et al., 2004). In recent years, various protocols for the construction of the compounds via solid-phase strategies have been reported (Gelen et al., 2003; Krchna & Holladay, 2002; Phoon & Sim, 2002; Franzen, 2000). The title compound has been synthesized and its crystal structure is presented here.
In the molecular structure (Fig. 1), the dihedral angles between pyridine (N1, C1, C2, C3, C4 and C5) and pyridine (N2, C16, C17, C18, C19 and C20) rings with the plane through the pyridine ring (N3, C9, C10, C11, C12 and C13) are 87.13 (10) and 89.15 (10)°, respectively. The C6═O1 bond length of 1.2078 (19) Å and C15═O2 bond length of 1.2066 (18) Å indicate the typical double bonds. Intramolecular C—H···N as well as intermolecular C—H···O hydrogen bonds are observed in the crystal structure.