Acta Cryst. (2009). E65, o2163 [ doi:10.1107/S1600536809031572 ]
In the title molecule, C20H22N2O2Se4, the dihedral angle between the pendant aromatic rings is 67.1 (2)°. The conformation is stabilized by two intramolecular O-H
N hydrogen bonds.
A mixture of 3,5-dihydroseleno-2-hydroxybenzaldehyde (564 mg, 2 mmol) and cyclohexane-1,2-diamine (114 mg, 1 mmol) in methanol (10 ml) was stirred for 2 h. After keeping the filtrate in air for 5 d, yellow blocks of (I) were formed.
The Se bound H atoms were located in a difference map and refined as riding in their as-found relative positions. The C-bound H atoms were positioned geometrically (C—H = 0.93 Å for the aromatic H atoms and C—H = 0.96 Å for the aliphatic H atoms) and were refined as riding, with Uiso(H) = 1.2Ueq(C).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
| C20H22N2O2Se4 | F(000) = 1232 |
| Mr = 638.24 | Dx = 1.914 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
| a = 15.493 (2) Å | θ = 9–12° |
| b = 9.2975 (15) Å | µ = 6.64 mm−1 |
| c = 16.353 (2) Å | T = 296 K |
| β = 109.865 (5)° | Block, yellow |
| V = 2215.4 (5) Å3 | 0.32 × 0.28 × 0.24 mm |
| Z = 4 |
| Enraf–Nonius CAD-4 diffractometer | 2743 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.048 |
| graphite | θmax = 25.7°, θmin = 1.4° |
| ω/2θ scans | h = −18→18 |
| Absorption correction: ψ scan (North et al., 1968) | k = −9→11 |
| Tmin = 0.225, Tmax = 0.299 | l = −19→19 |
| 11901 measured reflections | 3 standard reflections every 200 reflections |
| 4196 independent reflections | intensity decay: 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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.105 | H-atom parameters constrained |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0494P)2] where P = (Fo2 + 2Fc2)/3 |
| 4196 reflections | (Δ/σ)max = 0.001 |
| 255 parameters | Δρmax = 0.84 e Å−3 |
| 0 restraints | Δρmin = −0.54 e Å−3 |
| C20H22N2O2Se4 | V = 2215.4 (5) Å3 |
| Mr = 638.24 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 15.493 (2) Å | µ = 6.64 mm−1 |
| b = 9.2975 (15) Å | T = 296 K |
| c = 16.353 (2) Å | 0.32 × 0.28 × 0.24 mm |
| β = 109.865 (5)° |
| Enraf–Nonius CAD-4 diffractometer | 2743 reflections with I > 2σ(I) |
| Absorption correction: ψ scan (North et al., 1968) | Rint = 0.048 |
| Tmin = 0.225, Tmax = 0.299 | θmax = 25.7° |
| 11901 measured reflections | 3 standard reflections every 200 reflections |
| 4196 independent reflections | intensity decay: 1% |
| R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
| wR(F2) = 0.105 | Δρmax = 0.84 e Å−3 |
| S = 1.06 | Δρmin = −0.54 e Å−3 |
| 4196 reflections | Absolute structure: ? |
| 255 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| Se1 | 1.08983 (4) | 0.95743 (7) | 1.27220 (3) | 0.0629 (2) | |
| Se2 | 0.64176 (5) | 0.45492 (8) | 1.21754 (4) | 0.0694 (2) | |
| Se3 | 0.87275 (4) | 1.30994 (6) | 1.00077 (4) | 0.0618 (2) | |
| Se4 | 0.38089 (4) | 0.88004 (8) | 1.06267 (4) | 0.0683 (2) | |
| O2 | 0.8152 (2) | 1.0256 (4) | 0.9129 (2) | 0.0464 (9) | |
| H2A | 0.8043 | 0.9482 | 0.8874 | 0.070* | |
| C20 | 0.8744 (3) | 0.7422 (5) | 0.9727 (3) | 0.0397 (11) | |
| H20 | 0.8937 | 0.6520 | 0.9965 | 0.048* | |
| N2 | 0.8211 (2) | 0.7512 (4) | 0.8942 (2) | 0.0400 (10) | |
| N1 | 0.6651 (3) | 0.5930 (4) | 0.8980 (2) | 0.0414 (10) | |
| O1 | 0.6862 (2) | 0.4896 (4) | 1.0525 (2) | 0.0544 (9) | |
| H1 | 0.6915 | 0.4905 | 1.0043 | 0.082* | |
| C8 | 0.9110 (3) | 1.1261 (5) | 1.0457 (3) | 0.0373 (11) | |
| C2 | 0.5888 (3) | 0.5808 (5) | 1.1248 (3) | 0.0414 (12) | |
| C17 | 0.6070 (3) | 0.6798 (6) | 0.9083 (3) | 0.0412 (12) | |
| H17 | 0.5811 | 0.7480 | 0.8654 | 0.049* | |
| C9 | 0.9725 (3) | 1.1108 (5) | 1.1272 (3) | 0.0399 (12) | |
| H9 | 0.9948 | 1.1914 | 1.1616 | 0.048* | |
| C10 | 1.0019 (3) | 0.9748 (6) | 1.1593 (3) | 0.0388 (12) | |
| C11 | 0.9058 (3) | 0.8696 (5) | 1.0263 (3) | 0.0341 (11) | |
| C3 | 0.6196 (3) | 0.5804 (5) | 1.0534 (3) | 0.0384 (12) | |
| C18 | 0.7924 (3) | 0.6202 (5) | 0.8436 (3) | 0.0383 (11) | |
| H18 | 0.8229 | 0.5374 | 0.8786 | 0.046* | |
| C4 | 0.4792 (3) | 0.7638 (6) | 1.0590 (3) | 0.0441 (13) | |
| C5 | 0.5092 (3) | 0.7665 (6) | 0.9892 (3) | 0.0448 (13) | |
| H5 | 0.4822 | 0.8297 | 0.9435 | 0.054* | |
| C6 | 0.5190 (3) | 0.6701 (6) | 1.1264 (3) | 0.0431 (13) | |
| H6 | 0.4983 | 0.6672 | 1.1735 | 0.052* | |
| C7 | 0.5788 (3) | 0.6770 (5) | 0.9855 (3) | 0.0384 (12) | |
| C12 | 0.8760 (3) | 1.0062 (5) | 0.9929 (3) | 0.0343 (11) | |
| C19 | 0.6881 (3) | 0.6039 (5) | 0.8186 (3) | 0.0381 (12) | |
| H19 | 0.6579 | 0.6888 | 0.7856 | 0.046* | |
| C13 | 0.9695 (3) | 0.8555 (5) | 1.1101 (3) | 0.0391 (11) | |
| H13 | 0.9899 | 0.7648 | 1.1322 | 0.047* | |
| C21 | 0.8179 (3) | 0.6275 (6) | 0.7615 (3) | 0.0564 (15) | |
| H21A | 0.7892 | 0.7109 | 0.7275 | 0.068* | |
| H21B | 0.8839 | 0.6378 | 0.7773 | 0.068* | |
| C22 | 0.6558 (4) | 0.4706 (6) | 0.7630 (3) | 0.0545 (15) | |
| H22A | 0.6815 | 0.3860 | 0.7974 | 0.065* | |
| H22B | 0.5895 | 0.4642 | 0.7454 | 0.065* | |
| C23 | 0.7866 (3) | 0.4919 (6) | 0.7072 (4) | 0.0566 (16) | |
| H23A | 0.8183 | 0.4091 | 0.7398 | 0.068* | |
| H23B | 0.8021 | 0.4990 | 0.6546 | 0.068* | |
| C24 | 0.6834 (3) | 0.4719 (6) | 0.6833 (3) | 0.0553 (15) | |
| H24A | 0.6517 | 0.5494 | 0.6451 | 0.066* | |
| H24B | 0.6652 | 0.3819 | 0.6521 | 0.066* | |
| H2D | 0.6487 | 0.3556 | 1.1959 | 0.066* | |
| H3D | 0.8639 | 1.2980 | 0.9337 | 0.066* | |
| H1D | 1.0891 | 0.9500 | 1.3302 | 0.066* | |
| H4D | 0.3812 | 0.8789 | 1.1309 | 0.066* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Se1 | 0.0686 (4) | 0.0697 (5) | 0.0371 (3) | −0.0124 (3) | 0.0004 (3) | 0.0052 (3) |
| Se2 | 0.0850 (5) | 0.0807 (5) | 0.0424 (3) | 0.0074 (4) | 0.0217 (3) | 0.0183 (3) |
| Se3 | 0.0805 (4) | 0.0374 (3) | 0.0620 (4) | 0.0104 (3) | 0.0170 (3) | 0.0004 (3) |
| Se4 | 0.0677 (4) | 0.0887 (5) | 0.0628 (4) | 0.0210 (4) | 0.0410 (3) | −0.0011 (3) |
| O2 | 0.049 (2) | 0.046 (2) | 0.0379 (19) | 0.0044 (19) | 0.0062 (17) | −0.0063 (16) |
| C20 | 0.043 (3) | 0.031 (3) | 0.048 (3) | 0.002 (2) | 0.019 (3) | 0.002 (2) |
| N2 | 0.035 (2) | 0.045 (3) | 0.042 (2) | −0.003 (2) | 0.0160 (19) | −0.005 (2) |
| N1 | 0.042 (2) | 0.054 (3) | 0.034 (2) | −0.001 (2) | 0.0202 (19) | −0.003 (2) |
| O1 | 0.055 (2) | 0.067 (3) | 0.046 (2) | 0.014 (2) | 0.0226 (19) | 0.0060 (19) |
| C8 | 0.042 (3) | 0.037 (3) | 0.036 (3) | 0.000 (2) | 0.017 (2) | 0.002 (2) |
| C2 | 0.043 (3) | 0.052 (3) | 0.028 (2) | −0.012 (3) | 0.011 (2) | −0.001 (2) |
| C17 | 0.040 (3) | 0.057 (4) | 0.028 (2) | −0.002 (3) | 0.013 (2) | 0.001 (2) |
| C9 | 0.046 (3) | 0.035 (3) | 0.047 (3) | −0.005 (3) | 0.026 (3) | −0.006 (2) |
| C10 | 0.034 (3) | 0.052 (3) | 0.033 (3) | −0.003 (3) | 0.013 (2) | 0.001 (2) |
| C11 | 0.032 (2) | 0.038 (3) | 0.035 (3) | −0.003 (2) | 0.014 (2) | −0.005 (2) |
| C3 | 0.034 (3) | 0.048 (3) | 0.033 (3) | −0.008 (2) | 0.011 (2) | −0.006 (2) |
| C18 | 0.036 (3) | 0.037 (3) | 0.043 (3) | −0.002 (2) | 0.015 (2) | −0.009 (2) |
| C4 | 0.044 (3) | 0.055 (3) | 0.042 (3) | −0.003 (3) | 0.025 (2) | −0.005 (3) |
| C5 | 0.043 (3) | 0.060 (4) | 0.034 (3) | 0.005 (3) | 0.016 (2) | 0.003 (2) |
| C6 | 0.045 (3) | 0.057 (4) | 0.033 (3) | −0.011 (3) | 0.021 (2) | −0.006 (3) |
| C7 | 0.033 (3) | 0.054 (3) | 0.030 (2) | −0.003 (2) | 0.013 (2) | −0.005 (2) |
| C12 | 0.033 (3) | 0.040 (3) | 0.036 (3) | 0.005 (2) | 0.019 (2) | −0.001 (2) |
| C19 | 0.036 (3) | 0.052 (3) | 0.030 (2) | −0.005 (2) | 0.015 (2) | −0.004 (2) |
| C13 | 0.043 (3) | 0.037 (3) | 0.039 (3) | 0.000 (3) | 0.015 (2) | 0.003 (2) |
| C21 | 0.047 (3) | 0.073 (4) | 0.065 (3) | −0.020 (3) | 0.040 (3) | −0.023 (3) |
| C22 | 0.052 (3) | 0.071 (4) | 0.049 (3) | −0.023 (3) | 0.029 (3) | −0.018 (3) |
| C23 | 0.056 (3) | 0.070 (4) | 0.055 (3) | −0.012 (3) | 0.034 (3) | −0.027 (3) |
| C24 | 0.057 (3) | 0.074 (4) | 0.043 (3) | −0.018 (3) | 0.028 (3) | −0.019 (3) |
| Se1—C10 | 1.893 (5) | C10—C13 | 1.362 (7) |
| Se1—H1D | 0.9542 | C11—C13 | 1.396 (6) |
| Se2—C2 | 1.869 (5) | C11—C12 | 1.398 (6) |
| Se2—H2D | 1.0078 | C3—C7 | 1.400 (6) |
| Se3—C8 | 1.875 (5) | C18—C21 | 1.524 (6) |
| Se3—H3D | 1.0645 | C18—C19 | 1.534 (6) |
| Se4—C4 | 1.885 (5) | C18—H18 | 0.9800 |
| Se4—H4D | 1.1136 | C4—C5 | 1.372 (6) |
| O2—C12 | 1.340 (5) | C4—C6 | 1.376 (7) |
| O2—H2A | 0.8200 | C5—C7 | 1.380 (6) |
| C20—N2 | 1.271 (6) | C5—H5 | 0.9300 |
| C20—C11 | 1.455 (7) | C6—H6 | 0.9300 |
| C20—H20 | 0.9300 | C19—C22 | 1.518 (7) |
| N2—C18 | 1.455 (6) | C19—H19 | 0.9800 |
| N1—C17 | 1.262 (6) | C13—H13 | 0.9300 |
| N1—C19 | 1.461 (5) | C21—C23 | 1.523 (7) |
| O1—C3 | 1.337 (6) | C21—H21A | 0.9700 |
| O1—H1 | 0.8200 | C21—H21B | 0.9700 |
| C8—C9 | 1.357 (6) | C22—C24 | 1.503 (6) |
| C8—C12 | 1.402 (6) | C22—H22A | 0.9700 |
| C2—C6 | 1.371 (6) | C22—H22B | 0.9700 |
| C2—C3 | 1.404 (6) | C23—C24 | 1.524 (7) |
| C17—C7 | 1.470 (6) | C23—H23A | 0.9700 |
| C17—H17 | 0.9300 | C23—H23B | 0.9700 |
| C9—C10 | 1.385 (7) | C24—H24A | 0.9700 |
| C9—H9 | 0.9300 | C24—H24B | 0.9700 |
| C10—Se1—H1D | 136.7 | C7—C5—H5 | 119.4 |
| C2—Se2—H2D | 111.0 | C2—C6—C4 | 120.7 (4) |
| C8—Se3—H3D | 102.8 | C2—C6—H6 | 119.7 |
| C4—Se4—H4D | 107.3 | C4—C6—H6 | 119.7 |
| C12—O2—H2A | 109.5 | C5—C7—C3 | 120.1 (4) |
| N2—C20—C11 | 121.6 (5) | C5—C7—C17 | 119.4 (4) |
| N2—C20—H20 | 119.2 | C3—C7—C17 | 120.4 (4) |
| C11—C20—H20 | 119.2 | O2—C12—C11 | 122.2 (4) |
| C20—N2—C18 | 119.2 (4) | O2—C12—C8 | 119.4 (4) |
| C17—N1—C19 | 118.3 (4) | C11—C12—C8 | 118.3 (4) |
| C3—O1—H1 | 109.5 | N1—C19—C22 | 110.2 (4) |
| C9—C8—C12 | 121.1 (5) | N1—C19—C18 | 108.9 (4) |
| C9—C8—Se3 | 120.3 (4) | C22—C19—C18 | 110.1 (4) |
| C12—C8—Se3 | 118.6 (3) | N1—C19—H19 | 109.2 |
| C6—C2—C3 | 120.7 (4) | C22—C19—H19 | 109.2 |
| C6—C2—Se2 | 119.7 (3) | C18—C19—H19 | 109.2 |
| C3—C2—Se2 | 119.6 (4) | C10—C13—C11 | 120.0 (5) |
| N1—C17—C7 | 122.5 (4) | C10—C13—H13 | 120.0 |
| N1—C17—H17 | 118.8 | C11—C13—H13 | 120.0 |
| C7—C17—H17 | 118.8 | C23—C21—C18 | 110.5 (4) |
| C8—C9—C10 | 119.9 (5) | C23—C21—H21A | 109.5 |
| C8—C9—H9 | 120.0 | C18—C21—H21A | 109.5 |
| C10—C9—H9 | 120.0 | C23—C21—H21B | 109.5 |
| C13—C10—C9 | 120.8 (4) | C18—C21—H21B | 109.5 |
| C13—C10—Se1 | 120.4 (4) | H21A—C21—H21B | 108.1 |
| C9—C10—Se1 | 118.8 (4) | C24—C22—C19 | 112.3 (4) |
| C13—C11—C12 | 119.9 (4) | C24—C22—H22A | 109.1 |
| C13—C11—C20 | 119.7 (5) | C19—C22—H22A | 109.1 |
| C12—C11—C20 | 120.4 (4) | C24—C22—H22B | 109.1 |
| O1—C3—C7 | 122.6 (4) | C19—C22—H22B | 109.1 |
| O1—C3—C2 | 119.4 (4) | H22A—C22—H22B | 107.9 |
| C7—C3—C2 | 118.0 (4) | C21—C23—C24 | 110.4 (4) |
| N2—C18—C21 | 110.1 (4) | C21—C23—H23A | 109.6 |
| N2—C18—C19 | 108.9 (4) | C24—C23—H23A | 109.6 |
| C21—C18—C19 | 109.6 (4) | C21—C23—H23B | 109.6 |
| N2—C18—H18 | 109.4 | C24—C23—H23B | 109.6 |
| C21—C18—H18 | 109.4 | H23A—C23—H23B | 108.1 |
| C19—C18—H18 | 109.4 | C22—C24—C23 | 111.2 (4) |
| C5—C4—C6 | 119.5 (4) | C22—C24—H24A | 109.4 |
| C5—C4—Se4 | 121.5 (4) | C23—C24—H24A | 109.4 |
| C6—C4—Se4 | 119.0 (3) | C22—C24—H24B | 109.4 |
| C4—C5—C7 | 121.1 (5) | C23—C24—H24B | 109.4 |
| C4—C5—H5 | 119.4 | H24A—C24—H24B | 108.0 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2A···N2 | 0.82 | 1.85 | 2.575 (5) | 147 |
| O1—H1···N1 | 0.82 | 1.90 | 2.619 (5) | 145 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2A···N2 | 0.82 | 1.85 | 2.575 (5) | 147 |
| O1—H1···N1 | 0.82 | 1.90 | 2.619 (5) | 145 |
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Shi, L., Ge, H.-M., Tan, S.-H., Li, H.-Q., Song, Y.-C., Zhu, H.-L. & Tan, R.-X. (2007). Eur. J. Med. Chem. 42, 558–564.
![[Figure 1]](./hb5041fig1thm.gif)
There has been much research interest in Schiff base compounds due to their biological activities (Shi et al., 2007). In this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). There are two intramolecular O—H···N hydrogen bonds in (I) (Table 1).