Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803009814/fl6035sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803009814/fl6035IIsup2.hkl |
CCDC reference: 214831
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.092
- Data-to-parameter ratio = 11.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title compound, (II), was prepared as follows: in the presence of p-CH3C6H4SO3H, an intramolecular hydrogen-transfer cyclization of 1-N-(phenyl-5-chloro-2-hydroxylphenyl)methylene-2-N-(pyridin-2-yl)methylene −1,2-phenylenedimine was carried out between the two C═N bonds of the asymmetrical difunctional Schiff base (I) to give a cyclozation product, (II). The hydrogen on the carbon atom of the aldimine transferred to the carbon atom of ketoimine and formed a chiral center. The specific rotation of the products is 0°. A single-crystal of the title compound was obtained by slow diffusion (1:1 MeOH-MeCN) over a period of one month.
All the C—H and O—H H atoms were found in difference maps and refined isotropically. The bond lengths for C—H are from 0.952 (13)–1.058 (15) Å. The bond length for O—H is 0.99 (2) Å.
Data collection: XSCANS (Bruker, 2000); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C25H18ClN3O | F(000) = 856 |
Mr = 411.87 | Dx = 1.330 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 13.515 (2) Å | θ = 2.1–23.2° |
b = 9.597 (2) Å | µ = 0.21 mm−1 |
c = 16.875 (2) Å | T = 293 K |
β = 110.01 (1)° | Block, colorless |
V = 2056.6 (6) Å3 | 0.3 × 0.2 × 0.2 mm |
Z = 4 |
Bruker P4 diffractometer | 3129 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.045 |
Graphite monochromator | θmax = 26.0°, θmin = 1.6° |
ω scans | h = −16→16 |
Absorption correction: ψ scan (XPREP; Bruker, 2000) | k = −11→11 |
Tmin = 0.95, Tmax = 0.96 | l = −19→19 |
10228 measured reflections | 3 standard reflections every 97 reflections |
3982 independent reflections | intensity decay: 0.005% |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | All H-atom parameters refined |
S = 1.01 | w = 1/[σ2(Fo2) + (0.02P)2] where P = (Fo2 + 2Fc2)/3 |
3982 reflections | (Δ/σ)max < 0.001 |
343 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C25H18ClN3O | V = 2056.6 (6) Å3 |
Mr = 411.87 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.515 (2) Å | µ = 0.21 mm−1 |
b = 9.597 (2) Å | T = 293 K |
c = 16.875 (2) Å | 0.3 × 0.2 × 0.2 mm |
β = 110.01 (1)° |
Bruker P4 diffractometer | 3129 reflections with I > 2σ(I) |
Absorption correction: ψ scan (XPREP; Bruker, 2000) | Rint = 0.045 |
Tmin = 0.95, Tmax = 0.96 | 3 standard reflections every 97 reflections |
10228 measured reflections | intensity decay: 0.005% |
3982 independent reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.092 | All H-atom parameters refined |
S = 1.01 | Δρmax = 0.20 e Å−3 |
3982 reflections | Δρmin = −0.15 e Å−3 |
343 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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 3.8274 (0.0129) x + 7.9081 (0.0035) y + 6.1455 (0.0090) z = 3.1747 (0.0027) * −0.0810 (0.0013) C8 * −0.0222 (0.0016) C9 * 0.0426 (0.0017) C10 * 0.0368 (0.0017) C11 * −0.0277 (0.0012) C12 * 0.0515 (0.0007) N2 Rms deviation of fitted atoms = 0.0477 8.7556 (0.0051) x + 6.5746 (0.0035) y + 1.5415 (0.0053) z = 3.5549 (0.0013) Angle to previous plane (with approximate e.s.d.) = 24.29 (0.08) * 0.0174 (0.0013) C1 * −0.0006 (0.0012) C2 * −0.0131 (0.0012) C3 * −0.0076 (0.0012) C4 * 0.0068 (0.0011) C5 * 0.0174 (0.0012) C6 * −0.0196 (0.0010) C7 * 0.0068 (0.0010) N1 * −0.0075 (0.0010) N2 Rms deviation of fitted atoms =0.0123 |
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 | ||
N2 | 0.27370 (8) | 0.13167 (11) | 0.18508 (6) | 0.0471 (3) | |
N1 | 0.39468 (9) | −0.02686 (12) | 0.18339 (7) | 0.0547 (3) | |
C6 | 0.28406 (11) | 0.14024 (14) | 0.10580 (8) | 0.0493 (3) | |
C7 | 0.34144 (11) | 0.02950 (14) | 0.22825 (8) | 0.0504 (3) | |
C1 | 0.35919 (11) | 0.04011 (15) | 0.10617 (9) | 0.0534 (3) | |
C8 | 0.35184 (12) | −0.02258 (15) | 0.31334 (9) | 0.0567 (4) | |
C14 | 0.09869 (11) | 0.18864 (14) | 0.19490 (8) | 0.0518 (3) | |
C20 | 0.23141 (11) | 0.37906 (13) | 0.19685 (8) | 0.0490 (3) | |
C13 | 0.21320 (11) | 0.22933 (13) | 0.21886 (9) | 0.0473 (3) | |
C21 | 0.15082 (13) | 0.46110 (15) | 0.14484 (9) | 0.0559 (4) | |
N3 | 0.26999 (11) | −0.00367 (14) | 0.33936 (8) | 0.0674 (4) | |
C5 | 0.23442 (13) | 0.22136 (16) | 0.03491 (9) | 0.0578 (4) | |
C25 | 0.33245 (11) | 0.43563 (15) | 0.23018 (9) | 0.0536 (3) | |
C15 | 0.05079 (12) | 0.08976 (17) | 0.13415 (9) | 0.0604 (4) | |
C23 | 0.26988 (14) | 0.65271 (18) | 0.15976 (10) | 0.0671 (4) | |
C2 | 0.38656 (13) | 0.01773 (17) | 0.03450 (10) | 0.0613 (4) | |
C22 | 0.17066 (13) | 0.59602 (16) | 0.12594 (9) | 0.0621 (4) | |
C3 | 0.33773 (13) | 0.09732 (18) | −0.03571 (10) | 0.0652 (4) | |
C19 | 0.03843 (12) | 0.25473 (18) | 0.23605 (10) | 0.0640 (4) | |
C4 | 0.26306 (14) | 0.19749 (17) | −0.03527 (10) | 0.0637 (4) | |
C24 | 0.35072 (14) | 0.57270 (17) | 0.21221 (11) | 0.0649 (4) | |
C18 | −0.06732 (13) | 0.2243 (2) | 0.21586 (12) | 0.0741 (5) | |
C16 | −0.05565 (14) | 0.0605 (2) | 0.11388 (12) | 0.0749 (5) | |
C10 | 0.4456 (2) | −0.1491 (2) | 0.43792 (13) | 0.0946 (6) | |
C9 | 0.44085 (16) | −0.0947 (2) | 0.36024 (12) | 0.0807 (5) | |
C17 | −0.11394 (15) | 0.1269 (2) | 0.15494 (12) | 0.0777 (5) | |
C12 | 0.27714 (17) | −0.0583 (2) | 0.41450 (11) | 0.0792 (5) | |
C11 | 0.36287 (19) | −0.1305 (2) | 0.46453 (13) | 0.0883 (6) | |
Cl1 | 0.06903 (5) | 0.69575 (5) | 0.05804 (3) | 0.0996 (2) | |
O1 | 0.41034 (8) | 0.35159 (11) | 0.28005 (6) | 0.0625 (3) | |
H13 | 0.2429 (10) | 0.2156 (13) | 0.2782 (8) | 0.047 (3)* | |
H5 | 0.1811 (12) | 0.2929 (16) | 0.0350 (9) | 0.065 (4)* | |
H21 | 0.0784 (13) | 0.4275 (16) | 0.1212 (9) | 0.068 (4)* | |
H15 | 0.0938 (13) | 0.0354 (16) | 0.1066 (9) | 0.067 (4)* | |
H19 | 0.0747 (13) | 0.3327 (17) | 0.2798 (10) | 0.075 (5)* | |
H23 | 0.2850 (14) | 0.749 (2) | 0.1481 (11) | 0.090 (6)* | |
H24 | 0.4235 (14) | 0.6024 (18) | 0.2399 (10) | 0.085 (5)* | |
H2 | 0.4402 (14) | −0.0545 (18) | 0.0399 (10) | 0.082 (5)* | |
H4 | 0.2233 (13) | 0.2518 (17) | −0.0894 (10) | 0.079 (5)* | |
H3 | 0.3580 (12) | 0.0765 (16) | −0.0898 (10) | 0.071 (4)* | |
H16 | −0.0850 (16) | −0.008 (2) | 0.0682 (11) | 0.096 (6)* | |
H17 | −0.1927 (18) | 0.110 (2) | 0.1410 (13) | 0.119 (7)* | |
H12 | 0.2131 (16) | −0.044 (2) | 0.4339 (11) | 0.102 (6)* | |
H11 | 0.3677 (18) | −0.169 (2) | 0.5182 (14) | 0.125 (8)* | |
H18 | −0.1087 (19) | 0.271 (2) | 0.2452 (14) | 0.126 (8)* | |
H9 | 0.4990 (17) | −0.091 (2) | 0.3391 (12) | 0.108 (7)* | |
H10 | 0.516 (2) | −0.191 (3) | 0.4730 (17) | 0.171 (11)* | |
H1' | 0.4802 (18) | 0.397 (2) | 0.2964 (12) | 0.114 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.0459 (6) | 0.0445 (6) | 0.0516 (6) | 0.0016 (5) | 0.0177 (5) | −0.0012 (4) |
N1 | 0.0484 (7) | 0.0516 (7) | 0.0644 (7) | 0.0020 (5) | 0.0196 (6) | −0.0009 (5) |
C6 | 0.0480 (8) | 0.0499 (8) | 0.0513 (7) | −0.0029 (6) | 0.0188 (6) | −0.0042 (6) |
C7 | 0.0470 (8) | 0.0454 (8) | 0.0588 (8) | 0.0012 (6) | 0.0183 (6) | 0.0003 (6) |
C1 | 0.0488 (8) | 0.0528 (8) | 0.0605 (8) | −0.0038 (6) | 0.0213 (7) | −0.0061 (6) |
C8 | 0.0595 (9) | 0.0488 (8) | 0.0624 (8) | 0.0043 (6) | 0.0217 (7) | 0.0060 (6) |
C14 | 0.0484 (8) | 0.0490 (8) | 0.0595 (8) | −0.0019 (6) | 0.0204 (6) | 0.0019 (6) |
C20 | 0.0507 (8) | 0.0446 (8) | 0.0538 (7) | −0.0006 (6) | 0.0206 (6) | −0.0025 (5) |
C13 | 0.0468 (8) | 0.0445 (7) | 0.0522 (8) | 0.0009 (6) | 0.0189 (6) | −0.0011 (5) |
C21 | 0.0579 (10) | 0.0475 (8) | 0.0603 (8) | 0.0013 (7) | 0.0176 (7) | 0.0005 (6) |
N3 | 0.0707 (9) | 0.0674 (9) | 0.0703 (8) | 0.0051 (7) | 0.0320 (7) | 0.0139 (6) |
C5 | 0.0618 (10) | 0.0575 (9) | 0.0534 (8) | −0.0012 (7) | 0.0187 (7) | −0.0022 (6) |
C25 | 0.0543 (9) | 0.0494 (8) | 0.0594 (8) | −0.0026 (6) | 0.0226 (7) | −0.0026 (6) |
C15 | 0.0549 (9) | 0.0562 (9) | 0.0685 (9) | −0.0083 (7) | 0.0192 (7) | −0.0014 (7) |
C23 | 0.0719 (11) | 0.0509 (9) | 0.0784 (10) | −0.0044 (8) | 0.0256 (9) | 0.0013 (8) |
C2 | 0.0573 (9) | 0.0646 (10) | 0.0663 (9) | −0.0051 (8) | 0.0268 (8) | −0.0113 (7) |
C22 | 0.0686 (10) | 0.0491 (9) | 0.0665 (9) | 0.0032 (7) | 0.0204 (8) | 0.0019 (6) |
C3 | 0.0657 (10) | 0.0713 (11) | 0.0622 (9) | −0.0102 (8) | 0.0266 (8) | −0.0103 (7) |
C19 | 0.0516 (9) | 0.0682 (10) | 0.0745 (10) | 0.0013 (7) | 0.0247 (8) | 0.0001 (8) |
C4 | 0.0678 (10) | 0.0676 (10) | 0.0560 (8) | −0.0080 (8) | 0.0216 (8) | −0.0038 (7) |
C24 | 0.0621 (11) | 0.0532 (9) | 0.0796 (10) | −0.0078 (8) | 0.0244 (9) | −0.0022 (7) |
C18 | 0.0539 (10) | 0.0790 (12) | 0.0927 (12) | 0.0012 (8) | 0.0292 (9) | 0.0058 (9) |
C16 | 0.0585 (10) | 0.0737 (12) | 0.0859 (12) | −0.0151 (8) | 0.0163 (9) | −0.0003 (9) |
C10 | 0.1062 (18) | 0.0905 (15) | 0.0810 (13) | 0.0247 (12) | 0.0240 (13) | 0.0258 (10) |
C9 | 0.0744 (13) | 0.0865 (13) | 0.0786 (12) | 0.0221 (10) | 0.0227 (10) | 0.0205 (9) |
C17 | 0.0543 (11) | 0.0797 (13) | 0.0956 (13) | −0.0102 (9) | 0.0212 (10) | 0.0090 (10) |
C12 | 0.0928 (14) | 0.0755 (12) | 0.0767 (11) | 0.0073 (10) | 0.0385 (11) | 0.0171 (9) |
C11 | 0.1121 (18) | 0.0791 (14) | 0.0758 (12) | 0.0114 (11) | 0.0349 (12) | 0.0224 (10) |
Cl1 | 0.1077 (4) | 0.0630 (3) | 0.1041 (4) | 0.0179 (3) | 0.0054 (3) | 0.0200 (2) |
O1 | 0.0479 (6) | 0.0586 (6) | 0.0760 (7) | −0.0054 (5) | 0.0149 (5) | 0.0055 (5) |
N2—C7 | 1.3688 (17) | C15—H15 | 1.005 (15) |
N2—C6 | 1.3945 (16) | C23—C22 | 1.377 (2) |
N2—C13 | 1.4802 (16) | C23—C24 | 1.380 (2) |
N1—C7 | 1.3252 (17) | C23—H23 | 0.977 (19) |
N1—C1 | 1.3833 (17) | C2—C3 | 1.374 (2) |
C6—C5 | 1.392 (2) | C2—H2 | 0.984 (17) |
C6—C1 | 1.3965 (19) | C22—Cl1 | 1.7431 (16) |
C7—C8 | 1.4810 (19) | C3—C4 | 1.396 (2) |
C1—C2 | 1.397 (2) | C3—H3 | 1.058 (15) |
C8—N3 | 1.3348 (19) | C19—C18 | 1.382 (2) |
C8—C9 | 1.379 (2) | C19—H19 | 1.047 (16) |
C14—C15 | 1.384 (2) | C4—H4 | 1.029 (17) |
C14—C19 | 1.3909 (19) | C24—H24 | 0.975 (18) |
C14—C13 | 1.5109 (19) | C18—C17 | 1.373 (3) |
C20—C21 | 1.3865 (19) | C18—H18 | 0.97 (2) |
C20—C25 | 1.3965 (19) | C16—C17 | 1.371 (3) |
C20—C13 | 1.5251 (18) | C16—H16 | 0.988 (18) |
C13—H13 | 0.952 (13) | C10—C11 | 1.352 (3) |
C21—C22 | 1.382 (2) | C10—C9 | 1.392 (3) |
C21—H21 | 0.976 (16) | C10—H10 | 1.01 (3) |
N3—C12 | 1.345 (2) | C9—H9 | 0.97 (2) |
C5—C4 | 1.385 (2) | C17—H17 | 1.02 (2) |
C5—H5 | 0.996 (15) | C12—C11 | 1.366 (3) |
C25—O1 | 1.3640 (17) | C12—H12 | 1.03 (2) |
C25—C24 | 1.391 (2) | C11—H11 | 0.96 (2) |
C15—C16 | 1.389 (2) | O1—H1' | 0.99 (2) |
C7—N2—C6 | 106.53 (10) | C22—C23—H23 | 122.0 (11) |
C7—N2—C13 | 127.27 (11) | C24—C23—H23 | 118.6 (11) |
C6—N2—C13 | 125.60 (11) | C3—C2—C1 | 118.02 (15) |
C7—N1—C1 | 105.52 (11) | C3—C2—H2 | 126.4 (9) |
C5—C6—N2 | 132.88 (13) | C1—C2—H2 | 115.6 (9) |
C5—C6—C1 | 121.64 (12) | C23—C22—C21 | 120.87 (15) |
N2—C6—C1 | 105.46 (12) | C23—C22—Cl1 | 119.47 (12) |
N1—C7—N2 | 112.54 (12) | C21—C22—Cl1 | 119.66 (13) |
N1—C7—C8 | 121.75 (12) | C2—C3—C4 | 120.87 (15) |
N2—C7—C8 | 125.59 (12) | C2—C3—H3 | 116.7 (8) |
N1—C1—C6 | 109.95 (11) | C4—C3—H3 | 122.4 (8) |
N1—C1—C2 | 129.42 (14) | C18—C19—C14 | 120.87 (16) |
C6—C1—C2 | 120.62 (14) | C18—C19—H19 | 121.3 (9) |
N3—C8—C9 | 122.55 (14) | C14—C19—H19 | 117.7 (9) |
N3—C8—C7 | 117.30 (13) | C5—C4—C3 | 122.18 (16) |
C9—C8—C7 | 120.04 (14) | C5—C4—H4 | 117.5 (9) |
C15—C14—C19 | 118.49 (14) | C3—C4—H4 | 120.2 (9) |
C15—C14—C13 | 123.49 (12) | C23—C24—C25 | 120.35 (16) |
C19—C14—C13 | 118.01 (12) | C23—C24—H24 | 126.3 (11) |
C21—C20—C25 | 118.84 (13) | C25—C24—H24 | 113.4 (11) |
C21—C20—C13 | 122.13 (12) | C17—C18—C19 | 119.97 (18) |
C25—C20—C13 | 119.03 (12) | C17—C18—H18 | 120.0 (14) |
N2—C13—C14 | 112.56 (11) | C19—C18—H18 | 120.0 (14) |
N2—C13—C20 | 110.27 (10) | C17—C16—C15 | 120.49 (18) |
C14—C13—C20 | 114.47 (11) | C17—C16—H16 | 123.9 (11) |
N2—C13—H13 | 103.2 (8) | C15—C16—H16 | 115.6 (12) |
C14—C13—H13 | 105.7 (8) | C11—C10—C9 | 119.1 (2) |
C20—C13—H13 | 110.0 (8) | C11—C10—H10 | 124.9 (16) |
C22—C21—C20 | 120.39 (15) | C9—C10—H10 | 115.6 (16) |
C22—C21—H21 | 117.5 (9) | C8—C9—C10 | 118.63 (19) |
C20—C21—H21 | 122.1 (9) | C8—C9—H9 | 115.3 (12) |
C8—N3—C12 | 117.19 (15) | C10—C9—H9 | 125.5 (12) |
C4—C5—C6 | 116.67 (15) | C16—C17—C18 | 119.93 (17) |
C4—C5—H5 | 122.0 (8) | C16—C17—H17 | 123.0 (12) |
C6—C5—H5 | 121.3 (8) | C18—C17—H17 | 117.0 (12) |
O1—C25—C24 | 122.46 (14) | N3—C12—C11 | 123.55 (19) |
O1—C25—C20 | 117.42 (13) | N3—C12—H12 | 116.6 (11) |
C24—C25—C20 | 120.13 (14) | C11—C12—H12 | 119.8 (11) |
C14—C15—C16 | 120.23 (16) | C10—C11—C12 | 119.00 (19) |
C14—C15—H15 | 120.0 (9) | C10—C11—H11 | 117.7 (14) |
C16—C15—H15 | 119.7 (9) | C12—C11—H11 | 123.3 (14) |
C22—C23—C24 | 119.40 (16) | C25—O1—H1' | 112.0 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1′···N1i | 0.99 (2) | 1.77 (2) | 2.7520 (16) | 174.8 (17) |
C13—H13···N3 | 0.952 (13) | 2.317 (13) | 2.9422 (19) | 122.6 (9) |
C15—H15···N2 | 1.005 (15) | 2.513 (15) | 2.8643 (19) | 100.0 (10) |
C23—H23···N1ii | 0.977 (19) | 2.568 (19) | 3.464 (2) | 152.5 (14) |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C25H18ClN3O |
Mr | 411.87 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 13.515 (2), 9.597 (2), 16.875 (2) |
β (°) | 110.01 (1) |
V (Å3) | 2056.6 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.3 × 0.2 × 0.2 |
Data collection | |
Diffractometer | Bruker P4 diffractometer |
Absorption correction | ψ scan (XPREP; Bruker, 2000) |
Tmin, Tmax | 0.95, 0.96 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10228, 3982, 3129 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.092, 1.01 |
No. of reflections | 3982 |
No. of parameters | 343 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.20, −0.15 |
Computer programs: XSCANS (Bruker, 2000), XSCANS, SHELXTL (Bruker, 2000), SHELXTL.
N2—C13 | 1.4802 (16) | C20—C13 | 1.5251 (18) |
C14—C13 | 1.5109 (19) | C13—H13 | 0.952 (13) |
N2—C13—C14 | 112.56 (11) | N2—C13—H13 | 103.2 (8) |
N2—C13—C20 | 110.27 (10) | C14—C13—H13 | 105.7 (8) |
C14—C13—C20 | 114.47 (11) | C20—C13—H13 | 110.0 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1'···N1i | 0.99 (2) | 1.77 (2) | 2.7520 (16) | 174.8 (17) |
C13—H13···N3 | 0.952 (13) | 2.317 (13) | 2.9422 (19) | 122.6 (9) |
C15—H15···N2 | 1.005 (15) | 2.513 (15) | 2.8643 (19) | 100.0 (10) |
C23—H23···N1ii | 0.977 (19) | 2.568 (19) | 3.464 (2) | 152.5 (14) |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, y+1, z. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
The preparation of benzimidazoles has attracted some attention due to their variable physiological characteristics, such as anticancer agents, fungicides, antichagasic drugs, inhibitors, and plant-growth regulators (Zhou & Hassner, 2001; Matsuno et al., 2000; Kucukbay et al., 2001; Purygin et al., 2000; Bag et al., 1996).
In general, benzimidazole derivatives are obtained by the reaction of an o-phenylenediamine with a carboxylic acid, ester, amide, nitrile etc., or by the palladium-catalyzed carbonylation, coupling and cyclization of haloaromatics and o-phenylenediamines. Recently, Alajarin and co-workers (Alajarin et al., 1999) described a [4 + 2] intramolecular cycloaddition of ketimines with imines to form benzimidazo[1,2-b]isoquinolines, but it is a tedious procedure requiring expensive reagents. This paper reports a novel method for the synthesis of 1,2-benzimidazoles in good yields by hydrogen transfer cyclization between azomethine groups in the presence of acidic catalysts under mild conditions.
The structure analysis of the title compound, (II), shows that there is a chiral carbon atom in the molecule; however, it crystallizes in the centrosymmetric space group P21/c so its specific rotation is zero. The dihedral angle between the benzimidazole ring and the pyridyl ring is 24.29 (8)°. The bond angles H13—C13—N2, H13—C13—C20 and H13—C13—C14 are 103.2 (8), 110.0 (8) and 105.7 (8)°, respectively. There is one strong intermolecular O—H···N hydrogen bond and three weak C—H···N interactions (two intra- and one intermolecular), leading to the formation of a helical chain of molecules (see Fig. 3).