Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041000/ww6443sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041000/ww6443Isup2.hkl |
CCDC reference: 296700
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.051
- wR factor = 0.156
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 43 Perc. PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 1 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
For the preparation of 3-(4-imidazole-1-yl-phenyl)-1-(pyridin-2-yl)-prop-2-en-1-one, a flask charged with a mixture of 4-imidazole-1-benzaldehyde (8.6 g, 50 mmol), 2-acetylpyridine (6.1 g, 50 mmol) and 2% aqueous sodium hydroxide (150 ml) was stirred vigorously at room temperature for 30 min, and was then heated to about 333 K for 6 h. The reaction was monitored by TLC. After the reaction was complete, the reaction mixture was cooled to room temperature. A light-yellow solid was precipitated which was then filtered, washed thoroughly with water and air-dried to give 13.6 g of 3-(4-imidazole-1-yl-phenyl)-1-(pyridin-2-yl)-prop-2-en-1-one (yield: 98.0%).
For the preparation of IPTP, 2-acetylpyridine (1.8 g, 15 mmol) and 3-(4-imidazole-1-yl-phenyl)-1- (pyridin-2-yl)-prop-2-en-1-one (4.1 g, 15 mmol) and NaOH (2.4 g, 60 mmol) powder were crushed together with a pestle and mortar for 2 h. The yellow powder was added to a stirred solution of ammonium acetate (10 g, excess) in ethanol (100 ml). The reaction mixture was heated at reflux for 10 h. Upon cooling to room temperature, the precipitate was filtered, washed with water three times and dried to afford the product. Recrystallization from ethanol afforded white needle crystals. 1H NMR (CDCl3): δ 7.27 (t, 1H), 7.37 (m, 3H), 7.55 (d, 2H), 7.90 (m, 2H), 7.98 (s, 1H), 8.04 (d, 2H), 8.67 (s, 1H), 8.70 (s, 1H), 8.74 (m, 2H), 8.76 (s, 2H). 13C NMR (CDCl3): δ 117.7, 118.2, 120.9, 121.2, 123.5, 128.5, 129.9, 134.9, 136.3, 136.5, 148.5, 148.7, 155.3, 155.5, 155.7.
All H atoms were positioned geometricallyd and allowed to ride on their attached atoms, with C—H = 0.93 Å and Uiso(H)= 1.2Ueq(C).
Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure of IPTP showing 50% probability displacement ellipsoids. | |
Fig. 2. The packing diagram of IPTP. Hydrogen bonds are shown as dashed lines. |
C24H17N5 | F(000) = 784 |
Mr = 375.43 | Dx = 1.352 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 41 reflections |
a = 5.4807 (5) Å | θ = 5.2–12.5° |
b = 38.653 (5) Å | µ = 0.08 mm−1 |
c = 8.953 (1) Å | T = 293 K |
β = 103.470 (9)° | Plate, pale yellow |
V = 1844.5 (4) Å3 | 0.45 × 0.34 × 0.10 mm |
Z = 4 |
Bruker P4 diffractometer | 1574 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 26.0°, θmin = 2.4° |
ω scans | h = −6→1 |
Absorption correction: ψ scan (North et al., 1968) | k = −1→47 |
Tmin = 0.918, Tmax = 0.992 | l = −11→11 |
4935 measured reflections | 3 standard reflections every 97 reflections |
3625 independent reflections | intensity decay: none |
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)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.156 | w = 1/[σ2(Fo2) + (0.0662P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.93 | (Δ/σ)max < 0.001 |
3625 reflections | Δρmax = 0.19 e Å−3 |
263 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.025 (2) |
C24H17N5 | V = 1844.5 (4) Å3 |
Mr = 375.43 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 5.4807 (5) Å | µ = 0.08 mm−1 |
b = 38.653 (5) Å | T = 293 K |
c = 8.953 (1) Å | 0.45 × 0.34 × 0.10 mm |
β = 103.470 (9)° |
Bruker P4 diffractometer | 1574 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.035 |
Tmin = 0.918, Tmax = 0.992 | 3 standard reflections every 97 reflections |
4935 measured reflections | intensity decay: none |
3625 independent reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 0.93 | Δρmax = 0.19 e Å−3 |
3625 reflections | Δρmin = −0.18 e Å−3 |
263 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 > 2σ(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 | ||
C1 | −0.4512 (7) | −0.04771 (9) | 0.2268 (3) | 0.0733 (10) | |
H1A | −0.4764 | −0.0707 | 0.1969 | 0.088* | |
C2 | −0.2582 (7) | −0.02841 (9) | 0.2078 (4) | 0.0804 (11) | |
H2A | −0.1282 | −0.0354 | 0.1640 | 0.096* | |
C3 | −0.4990 (6) | 0.00118 (9) | 0.3178 (4) | 0.0744 (10) | |
H3A | −0.5633 | 0.0193 | 0.3654 | 0.089* | |
C4 | −0.1317 (5) | 0.03304 (7) | 0.2661 (3) | 0.0499 (7) | |
C5 | −0.0669 (6) | 0.04179 (7) | 0.1325 (3) | 0.0613 (8) | |
H5A | −0.1328 | 0.0295 | 0.0428 | 0.074* | |
C6 | 0.0977 (6) | 0.06907 (7) | 0.1314 (3) | 0.0605 (8) | |
H6A | 0.1413 | 0.0748 | 0.0401 | 0.073* | |
C7 | 0.1989 (5) | 0.08803 (7) | 0.2626 (3) | 0.0482 (7) | |
C8 | 0.1219 (6) | 0.07932 (7) | 0.3943 (3) | 0.0591 (8) | |
H8A | 0.1809 | 0.0921 | 0.4834 | 0.071* | |
C9 | −0.0417 (6) | 0.05193 (7) | 0.3969 (3) | 0.0584 (8) | |
H9A | −0.0897 | 0.0465 | 0.4871 | 0.070* | |
C10 | 0.3796 (5) | 0.11633 (6) | 0.2575 (3) | 0.0468 (7) | |
C11 | 0.5083 (5) | 0.11794 (7) | 0.1412 (3) | 0.0528 (7) | |
H11A | 0.4864 | 0.1006 | 0.0674 | 0.063* | |
C12 | 0.6693 (5) | 0.14529 (7) | 0.1343 (3) | 0.0499 (7) | |
C13 | 0.7993 (5) | 0.14817 (7) | 0.0071 (3) | 0.0517 (7) | |
C14 | 0.9829 (6) | 0.17280 (8) | 0.0081 (3) | 0.0639 (8) | |
H14A | 1.0220 | 0.1888 | 0.0876 | 0.077* | |
C15 | 1.1069 (6) | 0.17355 (9) | −0.1083 (4) | 0.0754 (10) | |
H15A | 1.2316 | 0.1899 | −0.1079 | 0.090* | |
C16 | 1.0451 (7) | 0.15002 (10) | −0.2246 (4) | 0.0747 (10) | |
H16A | 1.1280 | 0.1497 | −0.3042 | 0.090* | |
C17 | 0.8564 (7) | 0.12678 (9) | −0.2208 (4) | 0.0780 (10) | |
H17A | 0.8114 | 0.1111 | −0.3012 | 0.094* | |
C18 | 0.4279 (5) | 0.14264 (7) | 0.3670 (3) | 0.0519 (7) | |
H18A | 0.3462 | 0.1428 | 0.4471 | 0.062* | |
C19 | 0.5981 (5) | 0.16861 (6) | 0.3561 (3) | 0.0475 (7) | |
C20 | 0.6595 (5) | 0.19635 (6) | 0.4745 (3) | 0.0463 (7) | |
C21 | 0.8600 (6) | 0.21828 (7) | 0.4796 (3) | 0.0570 (8) | |
H21A | 0.9587 | 0.2160 | 0.4086 | 0.068* | |
C22 | 0.9126 (6) | 0.24360 (7) | 0.5913 (4) | 0.0637 (8) | |
H22A | 1.0456 | 0.2588 | 0.5957 | 0.076* | |
C23 | 0.7665 (6) | 0.24595 (8) | 0.6951 (4) | 0.0641 (8) | |
H23A | 0.7980 | 0.2625 | 0.7726 | 0.077* | |
C24 | 0.5715 (6) | 0.22305 (8) | 0.6814 (4) | 0.0674 (9) | |
H24A | 0.4714 | 0.2249 | 0.7519 | 0.081* | |
N1 | −0.6040 (5) | −0.02951 (7) | 0.2949 (3) | 0.0787 (9) | |
N2 | −0.2893 (4) | 0.00369 (6) | 0.2655 (3) | 0.0545 (6) | |
N3 | 0.7155 (4) | 0.17048 (5) | 0.2408 (2) | 0.0508 (6) | |
N4 | 0.5142 (5) | 0.19843 (6) | 0.5750 (3) | 0.0593 (7) | |
N5 | 0.7345 (5) | 0.12550 (6) | −0.1082 (3) | 0.0659 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.080 (2) | 0.071 (2) | 0.072 (2) | −0.024 (2) | 0.0217 (19) | −0.0142 (17) |
C2 | 0.093 (3) | 0.070 (2) | 0.093 (2) | −0.030 (2) | 0.051 (2) | −0.0287 (19) |
C3 | 0.066 (2) | 0.065 (2) | 0.102 (3) | 0.0005 (19) | 0.040 (2) | 0.0008 (19) |
C4 | 0.0511 (18) | 0.0487 (16) | 0.0517 (16) | −0.0092 (14) | 0.0154 (14) | −0.0025 (13) |
C5 | 0.071 (2) | 0.0618 (19) | 0.0518 (17) | −0.0178 (17) | 0.0145 (16) | −0.0059 (15) |
C6 | 0.072 (2) | 0.0613 (18) | 0.0507 (17) | −0.0102 (17) | 0.0201 (16) | 0.0041 (14) |
C7 | 0.0536 (17) | 0.0434 (15) | 0.0487 (15) | −0.0021 (14) | 0.0140 (14) | 0.0004 (13) |
C8 | 0.070 (2) | 0.0538 (17) | 0.0575 (17) | −0.0168 (16) | 0.0222 (16) | −0.0091 (14) |
C9 | 0.069 (2) | 0.0574 (17) | 0.0548 (17) | −0.0132 (17) | 0.0257 (16) | −0.0057 (14) |
C10 | 0.0520 (18) | 0.0400 (14) | 0.0490 (15) | 0.0001 (13) | 0.0132 (14) | 0.0047 (12) |
C11 | 0.0589 (19) | 0.0441 (15) | 0.0578 (17) | −0.0037 (15) | 0.0186 (15) | −0.0014 (13) |
C12 | 0.0527 (18) | 0.0448 (15) | 0.0544 (16) | 0.0037 (14) | 0.0169 (14) | 0.0043 (13) |
C13 | 0.0541 (18) | 0.0457 (16) | 0.0581 (17) | 0.0031 (15) | 0.0186 (15) | 0.0062 (14) |
C14 | 0.067 (2) | 0.0626 (19) | 0.0672 (19) | −0.0034 (18) | 0.0263 (17) | 0.0092 (16) |
C15 | 0.069 (2) | 0.083 (2) | 0.083 (2) | −0.008 (2) | 0.034 (2) | 0.016 (2) |
C16 | 0.078 (2) | 0.088 (2) | 0.068 (2) | 0.013 (2) | 0.037 (2) | 0.022 (2) |
C17 | 0.095 (3) | 0.079 (2) | 0.070 (2) | 0.002 (2) | 0.039 (2) | 0.0034 (18) |
C18 | 0.0560 (18) | 0.0473 (15) | 0.0556 (16) | −0.0013 (15) | 0.0196 (15) | 0.0024 (13) |
C19 | 0.0502 (17) | 0.0400 (14) | 0.0539 (16) | 0.0007 (14) | 0.0155 (14) | 0.0020 (13) |
C20 | 0.0441 (16) | 0.0408 (14) | 0.0536 (16) | 0.0020 (13) | 0.0103 (14) | 0.0044 (13) |
C21 | 0.0561 (19) | 0.0532 (17) | 0.0654 (19) | −0.0051 (15) | 0.0218 (16) | 0.0035 (15) |
C22 | 0.062 (2) | 0.0505 (17) | 0.078 (2) | −0.0080 (16) | 0.0142 (18) | −0.0019 (16) |
C23 | 0.062 (2) | 0.0540 (18) | 0.075 (2) | −0.0015 (17) | 0.0126 (18) | −0.0120 (16) |
C24 | 0.064 (2) | 0.0657 (19) | 0.078 (2) | −0.0029 (18) | 0.0260 (18) | −0.0155 (17) |
N1 | 0.0642 (19) | 0.0696 (18) | 0.107 (2) | −0.0169 (16) | 0.0293 (17) | 0.0019 (17) |
N2 | 0.0526 (15) | 0.0550 (15) | 0.0579 (14) | −0.0115 (13) | 0.0173 (12) | −0.0058 (12) |
N3 | 0.0514 (14) | 0.0448 (13) | 0.0584 (14) | 0.0010 (12) | 0.0175 (12) | 0.0017 (11) |
N4 | 0.0579 (16) | 0.0551 (15) | 0.0701 (16) | −0.0050 (13) | 0.0252 (14) | −0.0100 (13) |
N5 | 0.082 (2) | 0.0620 (16) | 0.0618 (15) | −0.0047 (15) | 0.0334 (15) | −0.0008 (13) |
C1—C2 | 1.338 (4) | C12—C13 | 1.482 (4) |
C1—N1 | 1.343 (4) | C13—N5 | 1.338 (3) |
C1—H1A | 0.9300 | C13—C14 | 1.384 (4) |
C2—N2 | 1.370 (4) | C14—C15 | 1.370 (4) |
C2—H2A | 0.9300 | C14—H14A | 0.9300 |
C3—N1 | 1.314 (4) | C15—C16 | 1.365 (4) |
C3—N2 | 1.342 (3) | C15—H15A | 0.9300 |
C3—H3A | 0.9300 | C16—C17 | 1.376 (4) |
C4—C5 | 1.367 (3) | C16—H16A | 0.9300 |
C4—C9 | 1.371 (3) | C17—N5 | 1.333 (3) |
C4—N2 | 1.425 (3) | C17—H17A | 0.9300 |
C5—C6 | 1.389 (4) | C18—C19 | 1.389 (3) |
C5—H5A | 0.9300 | C18—H18A | 0.9300 |
C6—C7 | 1.386 (4) | C19—N3 | 1.339 (3) |
C6—H6A | 0.9300 | C19—C20 | 1.490 (3) |
C7—C8 | 1.384 (3) | C20—N4 | 1.336 (3) |
C7—C10 | 1.484 (4) | C20—C21 | 1.380 (4) |
C8—C9 | 1.391 (4) | C21—C22 | 1.381 (4) |
C8—H8A | 0.9300 | C21—H21A | 0.9300 |
C9—H9A | 0.9300 | C22—C23 | 1.364 (4) |
C10—C11 | 1.388 (3) | C22—H22A | 0.9300 |
C10—C18 | 1.394 (3) | C23—C24 | 1.371 (4) |
C11—C12 | 1.388 (4) | C23—H23A | 0.9300 |
C11—H11A | 0.9300 | C24—N4 | 1.331 (3) |
C12—N3 | 1.345 (3) | C24—H24A | 0.9300 |
C2—C1—N1 | 111.1 (3) | C15—C14—H14A | 120.1 |
C2—C1—H1A | 124.4 | C13—C14—H14A | 120.1 |
N1—C1—H1A | 124.4 | C16—C15—C14 | 119.2 (3) |
C1—C2—N2 | 106.6 (3) | C16—C15—H15A | 120.4 |
C1—C2—H2A | 126.7 | C14—C15—H15A | 120.4 |
N2—C2—H2A | 126.7 | C15—C16—C17 | 118.0 (3) |
N1—C3—N2 | 113.0 (3) | C15—C16—H16A | 121.0 |
N1—C3—H3A | 123.5 | C17—C16—H16A | 121.0 |
N2—C3—H3A | 123.5 | N5—C17—C16 | 123.7 (3) |
C5—C4—C9 | 120.0 (3) | N5—C17—H17A | 118.1 |
C5—C4—N2 | 118.3 (2) | C16—C17—H17A | 118.1 |
C9—C4—N2 | 121.7 (2) | C19—C18—C10 | 119.9 (3) |
C4—C5—C6 | 119.7 (3) | C19—C18—H18A | 120.1 |
C4—C5—H5A | 120.2 | C10—C18—H18A | 120.1 |
C6—C5—H5A | 120.2 | N3—C19—C18 | 122.9 (2) |
C7—C6—C5 | 121.8 (3) | N3—C19—C20 | 116.1 (2) |
C7—C6—H6A | 119.1 | C18—C19—C20 | 120.9 (2) |
C5—C6—H6A | 119.1 | N4—C20—C21 | 122.4 (3) |
C8—C7—C6 | 116.9 (3) | N4—C20—C19 | 116.8 (2) |
C8—C7—C10 | 123.0 (2) | C21—C20—C19 | 120.8 (3) |
C6—C7—C10 | 120.1 (2) | C20—C21—C22 | 119.3 (3) |
C7—C8—C9 | 121.7 (3) | C20—C21—H21A | 120.3 |
C7—C8—H8A | 119.1 | C22—C21—H21A | 120.3 |
C9—C8—H8A | 119.1 | C23—C22—C21 | 118.9 (3) |
C4—C9—C8 | 119.8 (3) | C23—C22—H22A | 120.5 |
C4—C9—H9A | 120.1 | C21—C22—H22A | 120.5 |
C8—C9—H9A | 120.1 | C22—C23—C24 | 117.7 (3) |
C11—C10—C18 | 116.6 (3) | C22—C23—H23A | 121.1 |
C11—C10—C7 | 121.0 (2) | C24—C23—H23A | 121.1 |
C18—C10—C7 | 122.3 (2) | N4—C24—C23 | 125.1 (3) |
C12—C11—C10 | 120.5 (3) | N4—C24—H24A | 117.5 |
C12—C11—H11A | 119.8 | C23—C24—H24A | 117.5 |
C10—C11—H11A | 119.8 | C3—N1—C1 | 104.3 (3) |
N3—C12—C11 | 122.5 (2) | C3—N2—C2 | 104.9 (3) |
N3—C12—C13 | 116.5 (2) | C3—N2—C4 | 128.6 (3) |
C11—C12—C13 | 121.1 (3) | C2—N2—C4 | 126.4 (2) |
N5—C13—C14 | 121.2 (3) | C19—N3—C12 | 117.5 (2) |
N5—C13—C12 | 117.1 (3) | C24—N4—C20 | 116.5 (3) |
C14—C13—C12 | 121.7 (3) | C17—N5—C13 | 118.0 (3) |
C15—C14—C13 | 119.9 (3) | ||
N1—C1—C2—N2 | −0.4 (4) | C10—C18—C19—C20 | −177.9 (2) |
C9—C4—C5—C6 | 2.4 (4) | N3—C19—C20—N4 | 168.8 (2) |
N2—C4—C5—C6 | −176.4 (3) | C18—C19—C20—N4 | −11.1 (4) |
C4—C5—C6—C7 | −0.3 (4) | N3—C19—C20—C21 | −12.1 (4) |
C5—C6—C7—C8 | −2.1 (4) | C18—C19—C20—C21 | 168.1 (2) |
C5—C6—C7—C10 | 178.3 (3) | N4—C20—C21—C22 | −0.6 (4) |
C6—C7—C8—C9 | 2.5 (4) | C19—C20—C21—C22 | −179.7 (2) |
C10—C7—C8—C9 | −177.9 (3) | C20—C21—C22—C23 | 0.9 (4) |
C5—C4—C9—C8 | −2.0 (4) | C21—C22—C23—C24 | −0.8 (5) |
N2—C4—C9—C8 | 176.8 (3) | C22—C23—C24—N4 | 0.5 (5) |
C7—C8—C9—C4 | −0.5 (5) | N2—C3—N1—C1 | 1.1 (4) |
C8—C7—C10—C11 | 160.8 (3) | C2—C1—N1—C3 | −0.4 (4) |
C6—C7—C10—C11 | −19.7 (4) | N1—C3—N2—C2 | −1.3 (4) |
C8—C7—C10—C18 | −19.7 (4) | N1—C3—N2—C4 | 177.9 (3) |
C6—C7—C10—C18 | 159.8 (3) | C1—C2—N2—C3 | 1.0 (4) |
C18—C10—C11—C12 | −2.1 (4) | C1—C2—N2—C4 | −178.3 (3) |
C7—C10—C11—C12 | 177.5 (2) | C5—C4—N2—C3 | −130.4 (3) |
C10—C11—C12—N3 | 2.5 (4) | C9—C4—N2—C3 | 50.8 (4) |
C10—C11—C12—C13 | −177.3 (2) | C5—C4—N2—C2 | 48.7 (4) |
N3—C12—C13—N5 | −172.9 (2) | C9—C4—N2—C2 | −130.1 (3) |
C11—C12—C13—N5 | 6.9 (4) | C18—C19—N3—C12 | −2.0 (4) |
N3—C12—C13—C14 | 8.2 (4) | C20—C19—N3—C12 | 178.2 (2) |
C11—C12—C13—C14 | −172.0 (3) | C11—C12—N3—C19 | −0.4 (4) |
N5—C13—C14—C15 | −2.0 (4) | C13—C12—N3—C19 | 179.3 (2) |
C12—C13—C14—C15 | 176.9 (3) | C23—C24—N4—C20 | −0.2 (5) |
C13—C14—C15—C16 | 0.6 (5) | C21—C20—N4—C24 | 0.3 (4) |
C14—C15—C16—C17 | 1.0 (5) | C19—C20—N4—C24 | 179.4 (2) |
C15—C16—C17—N5 | −1.5 (5) | C16—C17—N5—C13 | 0.1 (5) |
C11—C10—C18—C19 | −0.2 (4) | C14—C13—N5—C17 | 1.6 (4) |
C7—C10—C18—C19 | −179.7 (2) | C12—C13—N5—C17 | −177.4 (3) |
C10—C18—C19—N3 | 2.3 (4) |
Experimental details
Crystal data | |
Chemical formula | C24H17N5 |
Mr | 375.43 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 5.4807 (5), 38.653 (5), 8.953 (1) |
β (°) | 103.470 (9) |
V (Å3) | 1844.5 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.45 × 0.34 × 0.10 |
Data collection | |
Diffractometer | Bruker P4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.918, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4935, 3625, 1574 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.156, 0.93 |
No. of reflections | 3625 |
No. of parameters | 263 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.18 |
Computer programs: XSCANS (Bruker, 1996), XSCANS, SHELXTL (Bruker, 1997), SHELXTL.
C1—N1 | 1.343 (4) | C12—N3 | 1.345 (3) |
C2—N2 | 1.370 (4) | C13—N5 | 1.338 (3) |
C3—N1 | 1.314 (4) | C17—N5 | 1.333 (3) |
C3—N2 | 1.342 (3) | C19—N3 | 1.339 (3) |
C4—N2 | 1.425 (3) | C20—N4 | 1.336 (3) |
C7—C10 | 1.484 (4) | C24—N4 | 1.331 (3) |
C3—N1—C1 | 104.3 (3) | C19—N3—C12 | 117.5 (2) |
C3—N2—C2 | 104.9 (3) | C24—N4—C20 | 116.5 (3) |
C3—N2—C4 | 128.6 (3) | C17—N5—C13 | 118.0 (3) |
C2—N2—C4 | 126.4 (2) |
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Polypyridine ligands have played an important role in many areas. In particular, the chelating ligand terpyridine (terpy) and its functionalized derivatives have been studied extensively as outstanding complexing agents for a wide range of transition metal ions (Heller & Schubert, 2003). This property has been widely used in analytical chemistry (Schubert & Eschbaumer, 2002), photochemistry for the design of luminescent devices (Harriman & Ziessel, 1998) and biochemistry (Trawick et al., 1998). Although the number of publications or investigations of terpyridine complexes has increased enormously, comparably few preparations of functionalized terpyridine derivatives have been reported as yet. 4-(4-Imidazole-1-yl-phenyl)-[2,2':6',2"] terpyridine is a novel compound containing terpyridine and imidazole coordination sites. We report here the synthesis, characterization and crystal structure of the title compound, IPTP or (I).
The molecular structure of the title compound was determined by single-crystal X-ray diffraction and shown in Fig. 1. The packing diagram is shown in Fig. 2. Bond lengths and angles in the compound are given in Table 1. The three pyridyl rings are almost co-planar, with interplanar angles of 7.1 (su?), 171 (su?) and 168.3 (su?)°, respectively. The benzene ring forms dihedral angles of 49.6 (su?) and 19.2 (su?)° with the medial pyridyl ring and imidazole ring.