Acta Cryst. (2008). E64, o1725 [ doi:10.1107/S1600536808025026 ]
The title compound, C20H19NO, was prepared from 2,6-lutidine and benzophenone. There are two symmetry-independent molecules in the asymmetric unit. Each molecule is involved in one intramolecular O-H
N hydrogen bond. In the crystal structure, helical chains are formed along the b axis by weak ![[pi]](/logos/entities/pi_rmgif.gif)
- interactions between neighbouring molecules [centroid-centroid distances between the pyridyl rings of the two independent molecules = 4.041 (3) and 4.051 (3) Å].
2-(6-Methyl-pyridin-2-yl)-1,1-diphenyl-ethanol was prepared from 2,6-lutidine and benzophenone according to a procedure described in the literature (Berg & Holm, 1985, yield: 60%). Colorless crystals were obtained by recrystallization from light petroleum-ethyl acetate(vol. ratio: 5:1) at room temperature.
1H-NMR (CDCl3, 400 MHz): δ = 8.1 (1 H, s, OH), 6.8–7.5 (13 H, 2 Ph + 3H), 3.7 (2 H, s, CH2), 2.5 (3 H, s, CH3).
The H atoms were placed in calculated positions except O—H atoms and included as part of a riding model, with C—H = 0.93–0.97 Å, and with Uequiv values set at 1.2–1.5 Uequiv of the parent atoms. The O—H atoms were located in the Fourier difference map and refined with a given isotropic thermal parameters 1.2 times the Uequiv for the parent atom.
Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./im2078fig1thm.gif)
| Fig. 1. A view of the title compound showing the atom-numbering scheme and displacement ellipsoids drawn at 30% probability level. Dashed lines indicate hydrogen bonds and all H atoms except those involved in hydrogen bonding have been omitted for clarity. |
![[Figure 2]](./im2078fig2thm.gif)
| Fig. 2. A view of the helical chain-like structure along the b axis. (i: x,1 + y,z; ii:x,-1 + y,z). |
| C20H19NO | F000 = 1232 |
| Mr = 289.36 | Dx = 1.208 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 9992 reflections |
| a = 13.466 (2) Å | θ = 2.3–27.7º |
| b = 8.022 (1) Å | µ = 0.07 mm−1 |
| c = 30.220 (3) Å | T = 291 (2) K |
| β = 102.874 (3)º | Bloc, colourless |
| V = 3182.4 (7) Å3 | 0.30 × 0.26 × 0.24 mm |
| Z = 8 |
| Bruker SMART APEX CCD diffractometer | 6247 independent reflections |
| Radiation source: sealed tube | 4901 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.039 |
| T = 291(2) K | θmax = 26.0º |
| φ and ω scans | θmin = 1.6º |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −16→16 |
| Tmin = 0.98, Tmax = 0.98 | k = −9→9 |
| 24109 measured reflections | l = −36→37 |
| 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)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.05P)2 + 0.55P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max < 0.001 |
| 6247 reflections | Δρmax = 0.12 e Å−3 |
| 405 parameters | Δρmin = −0.12 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C20H19NO | V = 3182.4 (7) Å3 |
| Mr = 289.36 | Z = 8 |
| Monoclinic, P21/c | Mo Kα |
| a = 13.466 (2) Å | µ = 0.07 mm−1 |
| b = 8.022 (1) Å | T = 291 (2) K |
| c = 30.220 (3) Å | 0.30 × 0.26 × 0.24 mm |
| β = 102.874 (3)º |
| Bruker SMART APEX CCD diffractometer | 6247 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | 4901 reflections with I > 2σ(I) |
| Tmin = 0.98, Tmax = 0.98 | Rint = 0.039 |
| 24109 measured reflections |
| R[F2 > 2σ(F2)] = 0.049 | 405 parameters |
| wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.03 | Δρmax = 0.12 e Å−3 |
| 6247 reflections | Δρmin = −0.12 e Å−3 |
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) 7.9264 (0.0081) x + 2.5384 (0.0055) y + 17.9519 (0.0173) z = 7.2409 (0.0023) * 0.0041 (0.0011) C2 * -0.0032 (0.0012) C3 * 0.0016 (0.0013) C4 * -0.0007 (0.0013) C5 * 0.0017 (0.0013) C6 * -0.0033 (0.0012) C7 Rms deviation of fitted atoms = 0.0027 8.6157 (0.0075) x - 6.1646 (0.0038) y - 4.0922 (0.0231) z = 2.4746 (0.0072) Angle to previous plane (with approximate e.s.d.) = 82.02 (0.06) * -0.0038 (0.0011) C8 * 0.0059 (0.0011) C9 * -0.0038 (0.0013) C10 * -0.0004 (0.0014) C11 * 0.0025 (0.0014) C12 * -0.0004 (0.0012) C13 Rms deviation of fitted atoms = 0.0034 - 0.0031 (0.0098) x + 7.0734 (0.0030) y - 13.8930 (0.0198) z = 1.4744 (0.0034) Angle to previous plane (with approximate e.s.d.) = 47.06 (0.06) * 0.0019 (0.0011) N1 * 0.0034 (0.0011) C15 * -0.0039 (0.0012) C16 * -0.0005 (0.0014) C17 * 0.0056 (0.0014) C18 * -0.0064 (0.0012) C19 Rms deviation of fitted atoms = 0.0041 7.9264 (0.0081) x + 2.5384 (0.0055) y + 17.9519 (0.0173) z = 7.2409 (0.0023) Angle to previous plane (with approximate e.s.d.) = 85.87 (0.05) * 0.0041 (0.0011) C2 * -0.0032 (0.0012) C3 * 0.0016 (0.0013) C4 * -0.0007 (0.0013) C5 * 0.0017 (0.0013) C6 * -0.0033 (0.0012) C7 Rms deviation of fitted atoms = 0.0027 8.6502 (0.0076) x + 6.1357 (0.0039) y - 2.9169 (0.0234) z = 5.1262 (0.0059) Angle to previous plane (with approximate e.s.d.) = 49.02 (0.07) * -0.0040 (0.0011) C22 * 0.0029 (0.0013) C23 * -0.0003 (0.0014) C24 * -0.0010 (0.0014) C25 * -0.0002 (0.0013) C26 * 0.0028 (0.0012) C27 Rms deviation of fitted atoms = 0.0024 - 8.0302 (0.0080) x + 2.4726 (0.0054) y + 25.8511 (0.0117) z = 4.4687 (0.0039) Angle to previous plane (with approximate e.s.d.) = 83.58 (0.06) * 0.0063 (0.0011) C28 * -0.0023 (0.0012) C29 * -0.0051 (0.0013) C30 * 0.0085 (0.0014) C31 * -0.0043 (0.0013) C32 * -0.0032 (0.0012) C33 Rms deviation of fitted atoms = 0.0053 - 0.0603 (0.0094) x + 7.0521 (0.0030) y - 14.0087 (0.0195) z = 4.9759 (0.0037) Angle to previous plane (with approximate e.s.d.) = 85.44 (0.05) * -0.0024 (0.0011) N2 * 0.0054 (0.0011) C35 * -0.0025 (0.0012) C36 * -0.0031 (0.0013) C37 * 0.0060 (0.0013) C38 * -0.0034 (0.0012) C39 Rms deviation of fitted atoms = 0.0040 8.6502 (0.0076) x + 6.1357 (0.0039) y - 2.9169 (0.0234) z = 5.1262 (0.0059) Angle to previous plane (with approximate e.s.d.) = 49.70 (0.06) * -0.0040 (0.0011) C22 * 0.0029 (0.0013) C23 * -0.0003 (0.0014) C24 * -0.0010 (0.0014) C25 * -0.0002 (0.0013) C26 * 0.0028 (0.0012) C27 Rms deviation of fitted atoms = 0.0024 |
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 | ||
| C1 | 0.55525 (11) | 0.30363 (18) | 0.12015 (5) | 0.0333 (3) | |
| C2 | 0.52945 (10) | 0.15683 (18) | 0.14763 (5) | 0.0333 (3) | |
| C3 | 0.46070 (12) | 0.1698 (2) | 0.17575 (5) | 0.0432 (4) | |
| H3 | 0.4257 | 0.2692 | 0.1767 | 0.052* | |
| C4 | 0.44374 (14) | 0.0364 (3) | 0.20236 (6) | 0.0552 (5) | |
| H4 | 0.3981 | 0.0474 | 0.2212 | 0.066* | |
| C5 | 0.49408 (16) | −0.1119 (3) | 0.20098 (7) | 0.0631 (5) | |
| H5 | 0.4823 | −0.2014 | 0.2187 | 0.076* | |
| C6 | 0.56142 (15) | −0.1273 (2) | 0.17356 (7) | 0.0606 (5) | |
| H6 | 0.5959 | −0.2274 | 0.1728 | 0.073* | |
| C7 | 0.57882 (12) | 0.0055 (2) | 0.14681 (6) | 0.0458 (4) | |
| H7 | 0.6244 | −0.0072 | 0.1280 | 0.055* | |
| C8 | 0.64575 (11) | 0.40377 (18) | 0.14754 (5) | 0.0364 (3) | |
| C9 | 0.67094 (12) | 0.4062 (2) | 0.19461 (6) | 0.0428 (4) | |
| H9 | 0.6339 | 0.3416 | 0.2108 | 0.051* | |
| C10 | 0.75135 (13) | 0.5046 (2) | 0.21792 (7) | 0.0546 (5) | |
| H10 | 0.7665 | 0.5063 | 0.2495 | 0.065* | |
| C11 | 0.80791 (14) | 0.5984 (2) | 0.19495 (8) | 0.0640 (6) | |
| H11 | 0.8616 | 0.6630 | 0.2107 | 0.077* | |
| C12 | 0.78427 (14) | 0.5961 (3) | 0.14796 (9) | 0.0674 (6) | |
| H12 | 0.8224 | 0.6593 | 0.1320 | 0.081* | |
| C13 | 0.70373 (13) | 0.4996 (2) | 0.12451 (7) | 0.0517 (4) | |
| H13 | 0.6885 | 0.4992 | 0.0929 | 0.062* | |
| C14 | 0.46541 (11) | 0.42749 (19) | 0.10506 (5) | 0.0381 (3) | |
| H14A | 0.4463 | 0.4708 | 0.1320 | 0.046* | |
| H14B | 0.4889 | 0.5207 | 0.0897 | 0.046* | |
| C15 | 0.37153 (11) | 0.35434 (19) | 0.07395 (5) | 0.0395 (3) | |
| C16 | 0.27485 (13) | 0.3698 (2) | 0.08237 (6) | 0.0511 (4) | |
| H16 | 0.2649 | 0.4206 | 0.1087 | 0.061* | |
| C17 | 0.19352 (14) | 0.3071 (3) | 0.05024 (8) | 0.0628 (5) | |
| H17 | 0.1277 | 0.3158 | 0.0548 | 0.075* | |
| C18 | 0.20984 (15) | 0.2327 (3) | 0.01190 (7) | 0.0642 (5) | |
| H18 | 0.1552 | 0.1917 | −0.0098 | 0.077* | |
| C19 | 0.30793 (15) | 0.2184 (2) | 0.00548 (6) | 0.0542 (5) | |
| C20 | 0.3320 (2) | 0.1393 (3) | −0.03588 (7) | 0.0780 (7) | |
| H20A | 0.3601 | 0.2215 | −0.0527 | 0.117* | |
| H20B | 0.2708 | 0.0944 | −0.0546 | 0.117* | |
| H20C | 0.3806 | 0.0512 | −0.0268 | 0.117* | |
| C21 | 0.06735 (10) | 0.80270 (18) | 0.12103 (5) | 0.0333 (3) | |
| C22 | 0.00363 (11) | 0.90017 (18) | 0.14826 (5) | 0.0356 (3) | |
| C23 | −0.07527 (13) | 1.0013 (2) | 0.12473 (7) | 0.0519 (4) | |
| H23 | −0.0884 | 1.0060 | 0.0932 | 0.062* | |
| C24 | −0.13383 (15) | 1.0943 (3) | 0.14768 (9) | 0.0668 (6) | |
| H24 | −0.1863 | 1.1604 | 0.1316 | 0.080* | |
| C25 | −0.11486 (15) | 1.0896 (3) | 0.19424 (8) | 0.0659 (6) | |
| H25 | −0.1544 | 1.1524 | 0.2097 | 0.079* | |
| C26 | −0.03709 (15) | 0.9914 (3) | 0.21801 (7) | 0.0578 (5) | |
| H26 | −0.0241 | 0.9879 | 0.2495 | 0.069* | |
| C27 | 0.02182 (12) | 0.8979 (2) | 0.19507 (6) | 0.0424 (4) | |
| H27 | 0.0744 | 0.8326 | 0.2114 | 0.051* | |
| C28 | 0.12469 (11) | 0.65852 (18) | 0.14885 (5) | 0.0350 (3) | |
| C29 | 0.07775 (13) | 0.5045 (2) | 0.14868 (6) | 0.0471 (4) | |
| H29 | 0.0135 | 0.4876 | 0.1302 | 0.057* | |
| C30 | 0.12589 (15) | 0.3745 (2) | 0.17595 (7) | 0.0566 (5) | |
| H30 | 0.0939 | 0.2716 | 0.1754 | 0.068* | |
| C31 | 0.22188 (17) | 0.3991 (3) | 0.20394 (7) | 0.0643 (6) | |
| H31 | 0.2533 | 0.3132 | 0.2226 | 0.077* | |
| C32 | 0.26986 (14) | 0.5481 (3) | 0.20410 (6) | 0.0576 (5) | |
| H32 | 0.3346 | 0.5633 | 0.2224 | 0.069* | |
| C33 | 0.22213 (12) | 0.6781 (2) | 0.17688 (6) | 0.0453 (4) | |
| H33 | 0.2555 | 0.7798 | 0.1773 | 0.054* | |
| C34 | 0.14015 (11) | 0.92662 (19) | 0.10486 (5) | 0.0382 (3) | |
| H34A | 0.1001 | 1.0187 | 0.0895 | 0.046* | |
| H34B | 0.1868 | 0.9716 | 0.1313 | 0.046* | |
| C35 | 0.20135 (12) | 0.85435 (19) | 0.07364 (5) | 0.0396 (3) | |
| C36 | 0.30642 (13) | 0.8702 (2) | 0.08174 (6) | 0.0502 (4) | |
| H36 | 0.3428 | 0.9219 | 0.1079 | 0.060* | |
| C37 | 0.35558 (15) | 0.8070 (3) | 0.04974 (7) | 0.0596 (5) | |
| H37 | 0.4260 | 0.8155 | 0.0542 | 0.072* | |
| C38 | 0.29968 (16) | 0.7313 (3) | 0.01125 (7) | 0.0600 (5) | |
| H38 | 0.3320 | 0.6899 | −0.0106 | 0.072* | |
| C39 | 0.19560 (14) | 0.7175 (2) | 0.00542 (6) | 0.0482 (4) | |
| C40 | 0.12872 (14) | 0.6369 (3) | −0.03596 (6) | 0.0563 (5) | |
| H40A | 0.0893 | 0.5496 | −0.0265 | 0.084* | |
| H40B | 0.1707 | 0.5909 | −0.0548 | 0.084* | |
| H40C | 0.0838 | 0.7190 | −0.0528 | 0.084* | |
| N1 | 0.38751 (11) | 0.28000 (18) | 0.03621 (5) | 0.0465 (3) | |
| N2 | 0.14697 (11) | 0.77822 (18) | 0.03610 (4) | 0.0443 (3) | |
| O1 | 0.58575 (9) | 0.24349 (15) | 0.08070 (4) | 0.0458 (3) | |
| H1A | 0.5263 (15) | 0.224 (2) | 0.0571 (7) | 0.055* | |
| O2 | −0.00304 (8) | 0.73711 (15) | 0.08224 (4) | 0.0461 (3) | |
| H2A | 0.0333 (14) | 0.704 (2) | 0.0597 (7) | 0.055* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0323 (7) | 0.0332 (8) | 0.0356 (8) | 0.0010 (6) | 0.0103 (6) | −0.0029 (6) |
| C2 | 0.0291 (7) | 0.0338 (8) | 0.0351 (7) | −0.0038 (6) | 0.0027 (6) | −0.0047 (6) |
| C3 | 0.0417 (8) | 0.0466 (9) | 0.0436 (9) | −0.0030 (7) | 0.0146 (7) | −0.0015 (7) |
| C4 | 0.0530 (10) | 0.0646 (12) | 0.0495 (10) | −0.0135 (9) | 0.0148 (8) | 0.0080 (9) |
| C5 | 0.0647 (12) | 0.0560 (12) | 0.0610 (12) | −0.0183 (10) | −0.0023 (10) | 0.0204 (9) |
| C6 | 0.0569 (11) | 0.0378 (10) | 0.0798 (14) | 0.0043 (8) | −0.0008 (10) | 0.0102 (9) |
| C7 | 0.0401 (8) | 0.0391 (9) | 0.0561 (10) | 0.0027 (7) | 0.0065 (7) | −0.0017 (8) |
| C8 | 0.0307 (7) | 0.0302 (8) | 0.0489 (9) | 0.0009 (6) | 0.0102 (6) | −0.0020 (6) |
| C9 | 0.0385 (8) | 0.0392 (9) | 0.0494 (9) | −0.0045 (7) | 0.0068 (7) | −0.0033 (7) |
| C10 | 0.0436 (9) | 0.0513 (11) | 0.0611 (11) | −0.0020 (8) | −0.0049 (8) | −0.0105 (9) |
| C11 | 0.0385 (9) | 0.0465 (11) | 0.0987 (17) | −0.0098 (8) | −0.0023 (10) | −0.0058 (11) |
| C12 | 0.0469 (10) | 0.0524 (12) | 0.1050 (18) | −0.0139 (9) | 0.0211 (11) | 0.0117 (11) |
| C13 | 0.0443 (9) | 0.0479 (10) | 0.0662 (11) | −0.0051 (8) | 0.0193 (8) | 0.0040 (9) |
| C14 | 0.0393 (8) | 0.0325 (8) | 0.0418 (8) | 0.0032 (6) | 0.0075 (6) | −0.0001 (6) |
| C15 | 0.0403 (8) | 0.0361 (8) | 0.0392 (8) | 0.0003 (7) | 0.0028 (6) | 0.0067 (7) |
| C16 | 0.0428 (9) | 0.0538 (11) | 0.0550 (11) | 0.0043 (8) | 0.0069 (8) | 0.0088 (8) |
| C17 | 0.0388 (9) | 0.0658 (13) | 0.0780 (14) | 0.0004 (9) | 0.0004 (9) | 0.0173 (11) |
| C18 | 0.0563 (12) | 0.0600 (12) | 0.0630 (13) | −0.0040 (9) | −0.0149 (10) | 0.0084 (10) |
| C19 | 0.0618 (11) | 0.0499 (10) | 0.0410 (9) | −0.0058 (8) | −0.0094 (8) | 0.0105 (8) |
| C20 | 0.0978 (17) | 0.0816 (16) | 0.0469 (11) | −0.0147 (13) | 0.0000 (11) | −0.0097 (11) |
| C21 | 0.0297 (7) | 0.0333 (8) | 0.0354 (8) | −0.0033 (6) | 0.0039 (6) | −0.0029 (6) |
| C22 | 0.0314 (7) | 0.0322 (8) | 0.0436 (8) | −0.0046 (6) | 0.0089 (6) | −0.0031 (6) |
| C23 | 0.0426 (9) | 0.0504 (10) | 0.0614 (11) | 0.0094 (8) | 0.0088 (8) | 0.0026 (9) |
| C24 | 0.0529 (11) | 0.0522 (11) | 0.0984 (17) | 0.0163 (9) | 0.0234 (11) | 0.0044 (11) |
| C25 | 0.0562 (11) | 0.0584 (12) | 0.0924 (16) | 0.0027 (10) | 0.0364 (11) | −0.0182 (11) |
| C26 | 0.0574 (11) | 0.0637 (12) | 0.0583 (11) | −0.0056 (9) | 0.0255 (9) | −0.0131 (10) |
| C27 | 0.0399 (8) | 0.0429 (9) | 0.0448 (9) | −0.0023 (7) | 0.0107 (7) | −0.0035 (7) |
| C28 | 0.0368 (7) | 0.0336 (8) | 0.0365 (8) | 0.0025 (6) | 0.0126 (6) | −0.0010 (6) |
| C29 | 0.0468 (9) | 0.0380 (9) | 0.0607 (11) | −0.0035 (7) | 0.0208 (8) | −0.0030 (8) |
| C30 | 0.0602 (11) | 0.0348 (9) | 0.0875 (14) | 0.0008 (8) | 0.0433 (11) | 0.0106 (9) |
| C31 | 0.0749 (13) | 0.0558 (12) | 0.0683 (13) | 0.0251 (10) | 0.0294 (11) | 0.0240 (10) |
| C32 | 0.0510 (10) | 0.0640 (12) | 0.0543 (11) | 0.0131 (9) | 0.0043 (8) | 0.0124 (9) |
| C33 | 0.0422 (9) | 0.0409 (9) | 0.0497 (10) | 0.0003 (7) | 0.0039 (7) | 0.0012 (7) |
| C34 | 0.0397 (8) | 0.0325 (8) | 0.0428 (8) | −0.0022 (6) | 0.0100 (6) | 0.0030 (6) |
| C35 | 0.0454 (8) | 0.0351 (8) | 0.0398 (8) | 0.0023 (7) | 0.0129 (7) | 0.0083 (7) |
| C36 | 0.0449 (9) | 0.0533 (10) | 0.0542 (10) | −0.0025 (8) | 0.0150 (8) | 0.0075 (8) |
| C37 | 0.0516 (10) | 0.0627 (12) | 0.0719 (13) | 0.0062 (9) | 0.0295 (10) | 0.0160 (10) |
| C38 | 0.0701 (13) | 0.0600 (12) | 0.0604 (12) | 0.0077 (10) | 0.0368 (10) | 0.0079 (10) |
| C39 | 0.0636 (11) | 0.0471 (10) | 0.0393 (9) | 0.0075 (8) | 0.0228 (8) | 0.0078 (7) |
| C40 | 0.0629 (11) | 0.0618 (12) | 0.0479 (10) | 0.0086 (9) | 0.0201 (9) | −0.0079 (9) |
| N1 | 0.0483 (8) | 0.0476 (8) | 0.0400 (8) | −0.0026 (6) | 0.0021 (6) | 0.0045 (6) |
| N2 | 0.0500 (8) | 0.0452 (8) | 0.0385 (7) | 0.0026 (6) | 0.0118 (6) | 0.0039 (6) |
| O1 | 0.0480 (6) | 0.0527 (7) | 0.0404 (6) | 0.0015 (5) | 0.0181 (5) | −0.0076 (5) |
| O2 | 0.0388 (6) | 0.0544 (7) | 0.0406 (6) | −0.0086 (5) | −0.0007 (5) | −0.0098 (5) |
| C1—O1 | 1.4286 (17) | C21—C22 | 1.529 (2) |
| C1—C2 | 1.525 (2) | C21—C28 | 1.533 (2) |
| C1—C8 | 1.538 (2) | C21—C34 | 1.550 (2) |
| C1—C14 | 1.553 (2) | C22—C27 | 1.381 (2) |
| C2—C7 | 1.387 (2) | C22—C23 | 1.399 (2) |
| C2—C3 | 1.393 (2) | C23—C24 | 1.379 (3) |
| C3—C4 | 1.388 (2) | C23—H23 | 0.9300 |
| C3—H3 | 0.9300 | C24—C25 | 1.373 (3) |
| C4—C5 | 1.375 (3) | C24—H24 | 0.9300 |
| C4—H4 | 0.9300 | C25—C26 | 1.378 (3) |
| C5—C6 | 1.363 (3) | C25—H25 | 0.9300 |
| C5—H5 | 0.9300 | C26—C27 | 1.385 (2) |
| C6—C7 | 1.389 (3) | C26—H26 | 0.9300 |
| C6—H6 | 0.9300 | C27—H27 | 0.9300 |
| C7—H7 | 0.9300 | C28—C29 | 1.387 (2) |
| C8—C9 | 1.387 (2) | C28—C33 | 1.403 (2) |
| C8—C13 | 1.388 (2) | C29—C30 | 1.396 (3) |
| C9—C10 | 1.398 (2) | C29—H29 | 0.9300 |
| C9—H9 | 0.9300 | C30—C31 | 1.392 (3) |
| C10—C11 | 1.365 (3) | C30—H30 | 0.9300 |
| C10—H10 | 0.9300 | C31—C32 | 1.358 (3) |
| C11—C12 | 1.384 (3) | C31—H31 | 0.9300 |
| C11—H11 | 0.9300 | C32—C33 | 1.394 (2) |
| C12—C13 | 1.391 (3) | C32—H32 | 0.9300 |
| C12—H12 | 0.9300 | C33—H33 | 0.9300 |
| C13—H13 | 0.9300 | C34—C35 | 1.501 (2) |
| C14—C15 | 1.515 (2) | C34—H34A | 0.9700 |
| C14—H14A | 0.9700 | C34—H34B | 0.9700 |
| C14—H14B | 0.9700 | C35—N2 | 1.351 (2) |
| C15—N1 | 1.346 (2) | C35—C36 | 1.387 (2) |
| C15—C16 | 1.387 (2) | C36—C37 | 1.384 (3) |
| C16—C17 | 1.386 (3) | C36—H36 | 0.9300 |
| C16—H16 | 0.9300 | C37—C38 | 1.377 (3) |
| C17—C18 | 1.364 (3) | C37—H37 | 0.9300 |
| C17—H17 | 0.9300 | C38—C39 | 1.377 (3) |
| C18—C19 | 1.382 (3) | C38—H38 | 0.9300 |
| C18—H18 | 0.9300 | C39—N2 | 1.340 (2) |
| C19—N1 | 1.346 (2) | C39—C40 | 1.514 (3) |
| C19—C20 | 1.500 (3) | C40—H40A | 0.9600 |
| C20—H20A | 0.9600 | C40—H40B | 0.9600 |
| C20—H20B | 0.9600 | C40—H40C | 0.9600 |
| C20—H20C | 0.9600 | O1—H1A | 0.96 (2) |
| C21—O2 | 1.4334 (17) | O2—H2A | 0.96 (2) |
| O1—C1—C2 | 109.66 (11) | C22—C21—C28 | 111.41 (12) |
| O1—C1—C8 | 106.55 (11) | O2—C21—C34 | 109.08 (12) |
| C2—C1—C8 | 111.07 (12) | C22—C21—C34 | 108.18 (11) |
| O1—C1—C14 | 108.72 (12) | C28—C21—C34 | 112.34 (12) |
| C2—C1—C14 | 113.37 (12) | C27—C22—C23 | 118.02 (15) |
| C8—C1—C14 | 107.20 (12) | C27—C22—C21 | 123.47 (14) |
| C7—C2—C3 | 117.55 (15) | C23—C22—C21 | 118.48 (14) |
| C7—C2—C1 | 119.86 (13) | C24—C23—C22 | 120.83 (18) |
| C3—C2—C1 | 122.52 (14) | C24—C23—H23 | 119.6 |
| C4—C3—C2 | 120.90 (16) | C22—C23—H23 | 119.6 |
| C4—C3—H3 | 119.5 | C25—C24—C23 | 120.24 (19) |
| C2—C3—H3 | 119.5 | C25—C24—H24 | 119.9 |
| C5—C4—C3 | 120.25 (17) | C23—C24—H24 | 119.9 |
| C5—C4—H4 | 119.9 | C24—C25—C26 | 119.75 (17) |
| C3—C4—H4 | 119.9 | C24—C25—H25 | 120.1 |
| C6—C5—C4 | 119.74 (17) | C26—C25—H25 | 120.1 |
| C6—C5—H5 | 120.1 | C25—C26—C27 | 120.15 (19) |
| C4—C5—H5 | 120.1 | C25—C26—H26 | 119.9 |
| C5—C6—C7 | 120.37 (18) | C27—C26—H26 | 119.9 |
| C5—C6—H6 | 119.8 | C22—C27—C26 | 121.00 (16) |
| C7—C6—H6 | 119.8 | C22—C27—H27 | 119.5 |
| C2—C7—C6 | 121.17 (16) | C26—C27—H27 | 119.5 |
| C2—C7—H7 | 119.4 | C29—C28—C33 | 117.78 (15) |
| C6—C7—H7 | 119.4 | C29—C28—C21 | 119.76 (14) |
| C9—C8—C13 | 118.06 (15) | C33—C28—C21 | 122.37 (13) |
| C9—C8—C1 | 122.85 (13) | C28—C29—C30 | 120.78 (17) |
| C13—C8—C1 | 119.07 (14) | C28—C29—H29 | 119.6 |
| C8—C9—C10 | 120.65 (16) | C30—C29—H29 | 119.6 |
| C8—C9—H9 | 119.7 | C31—C30—C29 | 119.95 (17) |
| C10—C9—H9 | 119.7 | C31—C30—H30 | 120.0 |
| C11—C10—C9 | 120.83 (19) | C29—C30—H30 | 120.0 |
| C11—C10—H10 | 119.6 | C32—C31—C30 | 120.22 (17) |
| C9—C10—H10 | 119.6 | C32—C31—H31 | 119.9 |
| C10—C11—C12 | 119.17 (17) | C30—C31—H31 | 119.9 |
| C10—C11—H11 | 120.4 | C31—C32—C33 | 120.01 (18) |
| C12—C11—H11 | 120.4 | C31—C32—H32 | 120.0 |
| C11—C12—C13 | 120.33 (18) | C33—C32—H32 | 120.0 |
| C11—C12—H12 | 119.8 | C32—C33—C28 | 121.25 (16) |
| C13—C12—H12 | 119.8 | C32—C33—H33 | 119.4 |
| C8—C13—C12 | 120.95 (18) | C28—C33—H33 | 119.4 |
| C8—C13—H13 | 119.5 | C35—C34—C21 | 115.16 (12) |
| C12—C13—H13 | 119.5 | C35—C34—H34A | 108.5 |
| C15—C14—C1 | 114.95 (12) | C21—C34—H34A | 108.5 |
| C15—C14—H14A | 108.5 | C35—C34—H34B | 108.5 |
| C1—C14—H14A | 108.5 | C21—C34—H34B | 108.5 |
| C15—C14—H14B | 108.5 | H34A—C34—H34B | 107.5 |
| C1—C14—H14B | 108.5 | N2—C35—C36 | 122.03 (15) |
| H14A—C14—H14B | 107.5 | N2—C35—C34 | 115.57 (13) |
| N1—C15—C16 | 121.93 (15) | C36—C35—C34 | 122.35 (15) |
| N1—C15—C14 | 115.37 (13) | C37—C36—C35 | 118.10 (18) |
| C16—C15—C14 | 122.62 (15) | C37—C36—H36 | 121.0 |
| C17—C16—C15 | 117.81 (18) | C35—C36—H36 | 121.0 |
| C17—C16—H16 | 121.1 | C38—C37—C36 | 119.67 (18) |
| C15—C16—H16 | 121.1 | C38—C37—H37 | 120.2 |
| C18—C17—C16 | 120.15 (19) | C36—C37—H37 | 120.2 |
| C18—C17—H17 | 119.9 | C37—C38—C39 | 119.50 (17) |
| C16—C17—H17 | 119.9 | C37—C38—H38 | 120.2 |
| C17—C18—C19 | 119.70 (18) | C39—C38—H38 | 120.2 |
| C17—C18—H18 | 120.2 | N2—C39—C38 | 121.49 (18) |
| C19—C18—H18 | 120.2 | N2—C39—C40 | 115.73 (16) |
| N1—C19—C18 | 120.77 (18) | C38—C39—C40 | 122.77 (16) |
| N1—C19—C20 | 116.34 (18) | C39—C40—H40A | 109.5 |
| C18—C19—C20 | 122.87 (18) | C39—C40—H40B | 109.5 |
| C19—C20—H20A | 109.5 | H40A—C40—H40B | 109.5 |
| C19—C20—H20B | 109.5 | C39—C40—H40C | 109.5 |
| H20A—C20—H20B | 109.5 | H40A—C40—H40C | 109.5 |
| C19—C20—H20C | 109.5 | H40B—C40—H40C | 109.5 |
| H20A—C20—H20C | 109.5 | C19—N1—C15 | 119.63 (16) |
| H20B—C20—H20C | 109.5 | C39—N2—C35 | 119.21 (15) |
| O2—C21—C22 | 106.24 (11) | C1—O1—H1A | 109.3 (11) |
| O2—C21—C28 | 109.39 (12) | C21—O2—H2A | 109.5 (11) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1A···N1 | 0.96 (2) | 1.89 (2) | 2.724 (2) | 144 (2) |
| O2—H2A···N2 | 0.96 (2) | 1.92 (2) | 2.718 (2) | 139 (2) |
| C18—H18···O2i | 0.93 | 2.70 | 3.518 (2) | 147 |
| C38—H38···O1ii | 0.93 | 2.65 | 3.472 (2) | 147 |
| Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1A···N1 | 0.96 (2) | 1.89 (2) | 2.724 (2) | 144 (2) |
| O2—H2A···N2 | 0.96 (2) | 1.92 (2) | 2.718 (2) | 139 (2) |
| C18—H18···O2i | 0.93 | 2.70 | 3.518 (2) | 147 |
| C38—H38···O1ii | 0.93 | 2.65 | 3.472 (2) | 147 |
| Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z. |
We thank the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (grant No. 07KJD150101) for financial support.
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There is a growing interest in the chemistry of metal-nitrido complexes, particularly those of late transition metals (Dehnicke et al., 2001). 2-(6-Methyl-pyridin-2-yl)-1,1-diphenyl-ethanol has been used as a multianionic chelating (N, O) ligand and coordinated with transition metals and main group elements, such as Ru, Os, Mo, B, Si etc. (Yip et al., 2003; Gibson et al., 2007). It can be prepared from 2,6-lutidine in moderate yield (Koning et al., 2000). During our studies, we obtained single crystals of the title compound report its crystal structure herein.
The crystal structure of title compound, C20H19NO, shows that all the bond lengths and angles have normal values. In an asymmetric unit there are two symmetry independent molecules I and II. Each molecule has one intramolecular O—H···N hydrogen bond (O1—H1A···N1, O2—H2A···N2)(Fig. 1).
Molecule I exhibits two benzene rings A (C2—C7) and B (C8—C13) as well as a pyridine ring C (N1/C15—C19) that are not coplanar with respect to each other. The dihedral angles between rings A and B, B and C, and C and A measure to 82.02 (6)°, 47.06 (6)°, and 85.87 (5)°, respectively.
Molecule II looks pretty much the same as molecule I, but the dihedral angles are significantly different. The angles between rings D(C22—C27) and E(C28—C33), E and F(N2/C35—C39), and F and D are 83.58 (6)°, 85.44 (5)°, and 49.70 (6)°, respectively.
In the crystal packing weak π–π interactions between neighbouring molecules I and II are observed, the distance of g1-g2 being 4.041 (3) and 4.051 (3) Å (g1 is center of mass of N1/C15—C19, g2 is center of mass of N2/C35—C39). Helical chains along the b axis are formed by these interactions (Fig. 2).
The additional weak intermolecular C18—H18···O2iii and C38—H38···O1iv (iii: -x,1 - y,-z; iv: 1 - x,1 - y,-z) hydrogen bonds play part an important role linking the helical chains to form the three-dimensional crystal structure.