organic compounds
In the title molecule, C20H22N2O, the pyridine heterocycle has an envelope conformation. The crystal packing is stabilized by intermolecular N—HO hydrogen bonds, which link the molecules into chains along the [10] direction.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680502413X/cv6556sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680502413X/cv6556Isup2.hkl |
CCDC reference: 283786
Computing details top
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.
(-)-1-Benzyl-4-[1(S)-phenylethylamino]-5,6-dihydropyridin-2(1H)-one top
Crystal data top
C20H22N2O | Z = 1 |
Mr = 306.40 | F(000) = 164 |
Triclinic, P1 | Dx = 1.168 Mg m−3 |
Hall symbol: P 1 | Melting point: 434 K |
a = 6.0091 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 6.4829 (8) Å | Cell parameters from 77 reflections |
c = 12.2030 (15) Å | θ = 3.6–14.1° |
α = 81.136 (10)° | µ = 0.07 mm−1 |
β = 80.67 (1)° | T = 296 K |
γ = 69.04 (1)° | Prism, colourless |
V = 435.67 (9) Å3 | 0.48 × 0.40 × 0.16 mm |
Data collection top
Bruker P4 diffractometer | Rint = 0.020 |
Radiation source: fine-focus sealed tube, FN4 | θmax = 26.3°, θmin = 3.4° |
Graphite monochromator | h = −7→7 |
ω scans | k = −8→7 |
3488 measured reflections | l = −15→15 |
1757 independent reflections | 3 standard reflections every 97 reflections |
1481 reflections with I > 2σ(I) | intensity decay: 1% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: geom and difmap |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0444P)2 + 0.0309P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
1757 reflections | Δρmax = 0.11 e Å−3 |
214 parameters | Δρmin = −0.09 e Å−3 |
3 restraints | Extinction correction: SHELXTL-Plus (Sheldrick, 1998), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.091 (12) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
N1 | 0.5371 (3) | 0.0310 (3) | 0.79695 (16) | 0.0506 (5) | |
O1 | 0.8481 (3) | −0.1208 (3) | 0.89904 (16) | 0.0681 (5) | |
C2 | 0.6715 (4) | 0.0429 (4) | 0.87423 (18) | 0.0463 (5) | |
C3 | 0.5983 (4) | 0.2452 (4) | 0.92672 (18) | 0.0451 (5) | |
H3A | 0.7045 | 0.2687 | 0.9669 | 0.054* | |
C4 | 0.3778 (4) | 0.4027 (3) | 0.91891 (17) | 0.0429 (5) | |
C5 | 0.2177 (4) | 0.3773 (4) | 0.8433 (2) | 0.0547 (6) | |
H5A | 0.1050 | 0.3118 | 0.8869 | 0.066* | |
H5B | 0.1264 | 0.5227 | 0.8097 | 0.066* | |
C6 | 0.3584 (5) | 0.2339 (4) | 0.7527 (2) | 0.0607 (7) | |
H6A | 0.2496 | 0.1951 | 0.7159 | 0.073* | |
H6B | 0.4384 | 0.3168 | 0.6975 | 0.073* | |
N7 | 0.2809 (4) | 0.5786 (3) | 0.97903 (17) | 0.0505 (5) | |
H7A | 0.139 (6) | 0.676 (5) | 0.961 (3) | 0.067 (8)* | |
C8 | 0.4060 (5) | 0.6408 (4) | 1.0536 (2) | 0.0536 (6) | |
H8A | 0.5501 | 0.6623 | 1.0107 | 0.064* | |
C9 | 0.2412 (8) | 0.8635 (5) | 1.0945 (3) | 0.0897 (11) | |
H9A | 0.2002 | 0.9726 | 1.0315 | 0.135* | |
H9B | 0.3226 | 0.9110 | 1.1418 | 0.135* | |
H9C | 0.0976 | 0.8462 | 1.1358 | 0.135* | |
C10 | 0.4819 (4) | 0.4702 (4) | 1.15329 (19) | 0.0489 (5) | |
C11 | 0.6715 (6) | 0.4612 (6) | 1.2054 (3) | 0.0812 (9) | |
H11A | 0.7563 | 0.5571 | 1.1782 | 0.097* | |
C12 | 0.7384 (7) | 0.3101 (8) | 1.2986 (3) | 0.1045 (13) | |
H12A | 0.8658 | 0.3079 | 1.3336 | 0.125* | |
C13 | 0.6194 (6) | 0.1652 (6) | 1.3392 (3) | 0.0876 (10) | |
H13A | 0.6664 | 0.0628 | 1.4007 | 0.105* | |
C14 | 0.4310 (6) | 0.1728 (5) | 1.2883 (2) | 0.0738 (8) | |
H14A | 0.3476 | 0.0757 | 1.3156 | 0.089* | |
C15 | 0.3624 (5) | 0.3236 (4) | 1.1963 (2) | 0.0561 (6) | |
H15A | 0.2329 | 0.3265 | 1.1627 | 0.067* | |
C16 | 0.6019 (4) | −0.1712 (4) | 0.7444 (2) | 0.0539 (6) | |
H16A | 0.4595 | −0.1762 | 0.7187 | 0.065* | |
H16B | 0.6533 | −0.2966 | 0.8005 | 0.065* | |
C17 | 0.7982 (4) | −0.1998 (4) | 0.6465 (2) | 0.0495 (5) | |
C18 | 0.8451 (6) | −0.3710 (5) | 0.5818 (3) | 0.0778 (9) | |
H18A | 0.7493 | −0.4596 | 0.5952 | 0.093* | |
C19 | 1.0351 (8) | −0.4111 (6) | 0.4969 (3) | 0.0999 (12) | |
H19A | 1.0672 | −0.5289 | 0.4550 | 0.120* | |
C20 | 1.1742 (6) | −0.2818 (6) | 0.4742 (3) | 0.0892 (11) | |
H20A | 1.3000 | −0.3092 | 0.4167 | 0.107* | |
C21 | 1.1270 (6) | −0.1114 (6) | 0.5367 (2) | 0.0797 (9) | |
H21A | 1.2208 | −0.0209 | 0.5214 | 0.096* | |
C22 | 0.9425 (5) | −0.0713 (5) | 0.6220 (2) | 0.0619 (7) | |
H22A | 0.9145 | 0.0452 | 0.6642 | 0.074* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0448 (11) | 0.0449 (10) | 0.0539 (11) | −0.0005 (9) | −0.0104 (9) | −0.0127 (9) |
O1 | 0.0551 (10) | 0.0567 (10) | 0.0717 (11) | 0.0155 (8) | −0.0209 (9) | −0.0155 (9) |
C2 | 0.0383 (12) | 0.0448 (12) | 0.0455 (12) | −0.0017 (10) | −0.0061 (10) | −0.0036 (9) |
C3 | 0.0367 (11) | 0.0482 (12) | 0.0467 (12) | −0.0062 (9) | −0.0109 (9) | −0.0078 (10) |
C4 | 0.0433 (11) | 0.0372 (11) | 0.0418 (11) | −0.0058 (9) | −0.0065 (9) | −0.0030 (9) |
C5 | 0.0424 (12) | 0.0484 (12) | 0.0648 (15) | 0.0019 (10) | −0.0193 (11) | −0.0097 (11) |
C6 | 0.0588 (15) | 0.0539 (14) | 0.0622 (15) | −0.0005 (12) | −0.0260 (12) | −0.0112 (12) |
N7 | 0.0487 (11) | 0.0379 (9) | 0.0565 (11) | 0.0005 (8) | −0.0168 (9) | −0.0067 (8) |
C8 | 0.0623 (14) | 0.0453 (12) | 0.0552 (14) | −0.0207 (11) | −0.0055 (11) | −0.0075 (10) |
C9 | 0.133 (3) | 0.0442 (14) | 0.091 (2) | −0.0166 (17) | −0.028 (2) | −0.0201 (14) |
C10 | 0.0462 (12) | 0.0512 (12) | 0.0478 (12) | −0.0127 (10) | −0.0027 (10) | −0.0135 (10) |
C11 | 0.0653 (17) | 0.112 (3) | 0.077 (2) | −0.0432 (18) | −0.0171 (15) | −0.0012 (18) |
C12 | 0.071 (2) | 0.158 (4) | 0.083 (2) | −0.029 (2) | −0.0369 (19) | −0.004 (2) |
C13 | 0.084 (2) | 0.097 (2) | 0.0600 (18) | −0.006 (2) | −0.0152 (17) | 0.0027 (17) |
C14 | 0.094 (2) | 0.0690 (17) | 0.0522 (15) | −0.0261 (16) | −0.0017 (15) | 0.0014 (13) |
C15 | 0.0622 (15) | 0.0568 (14) | 0.0498 (13) | −0.0207 (12) | −0.0073 (11) | −0.0054 (11) |
C16 | 0.0544 (14) | 0.0470 (12) | 0.0583 (14) | −0.0131 (11) | −0.0034 (11) | −0.0130 (10) |
C17 | 0.0531 (13) | 0.0414 (11) | 0.0461 (12) | −0.0041 (10) | −0.0113 (10) | −0.0050 (9) |
C18 | 0.094 (2) | 0.0629 (17) | 0.077 (2) | −0.0249 (16) | 0.0023 (17) | −0.0271 (15) |
C19 | 0.129 (3) | 0.077 (2) | 0.079 (2) | −0.016 (2) | 0.013 (2) | −0.0381 (18) |
C20 | 0.084 (2) | 0.096 (3) | 0.0637 (18) | −0.010 (2) | 0.0135 (17) | −0.0116 (18) |
C21 | 0.0720 (19) | 0.106 (2) | 0.0581 (16) | −0.0329 (17) | −0.0007 (14) | −0.0007 (17) |
C22 | 0.0675 (16) | 0.0691 (17) | 0.0491 (14) | −0.0221 (14) | −0.0054 (12) | −0.0107 (12) |
Geometric parameters (Å, º) top
N1—C2 | 1.364 (3) | C11—C12 | 1.391 (5) |
N1—C16 | 1.447 (3) | C11—H11A | 0.9300 |
N1—C6 | 1.461 (3) | C12—C13 | 1.364 (6) |
O1—C2 | 1.242 (3) | C12—H12A | 0.9300 |
C2—C3 | 1.442 (3) | C13—C14 | 1.360 (5) |
C3—C4 | 1.360 (3) | C13—H13A | 0.9300 |
C3—H3A | 0.9300 | C14—C15 | 1.381 (4) |
C4—N7 | 1.350 (3) | C14—H14A | 0.9300 |
C4—C5 | 1.501 (3) | C15—H15A | 0.9300 |
C5—C6 | 1.500 (3) | C16—C17 | 1.520 (3) |
C5—H5A | 0.9700 | C16—H16A | 0.9700 |
C5—H5B | 0.9700 | C16—H16B | 0.9700 |
C6—H6A | 0.9700 | C17—C22 | 1.375 (4) |
C6—H6B | 0.9700 | C17—C18 | 1.381 (4) |
N7—C8 | 1.451 (3) | C18—C19 | 1.390 (5) |
N7—H7A | 0.90 (3) | C18—H18A | 0.9300 |
C8—C10 | 1.522 (3) | C19—C20 | 1.354 (6) |
C8—C9 | 1.534 (4) | C19—H19A | 0.9300 |
C8—H8A | 0.9800 | C20—C21 | 1.360 (5) |
C9—H9A | 0.9600 | C20—H20A | 0.9300 |
C9—H9B | 0.9600 | C21—C22 | 1.373 (4) |
C9—H9C | 0.9600 | C21—H21A | 0.9300 |
C10—C11 | 1.372 (4) | C22—H22A | 0.9300 |
C10—C15 | 1.381 (3) | ||
C2—N1—C16 | 119.82 (18) | C15—C10—C8 | 122.2 (2) |
C2—N1—C6 | 119.26 (18) | C10—C11—C12 | 120.8 (3) |
C16—N1—C6 | 119.90 (19) | C10—C11—H11A | 119.6 |
O1—C2—N1 | 119.5 (2) | C12—C11—H11A | 119.6 |
O1—C2—C3 | 122.2 (2) | C13—C12—C11 | 120.8 (3) |
N1—C2—C3 | 118.27 (17) | C13—C12—H12A | 119.6 |
C4—C3—C2 | 121.65 (19) | C11—C12—H12A | 119.6 |
C4—C3—H3A | 119.2 | C14—C13—C12 | 118.9 (3) |
C2—C3—H3A | 119.2 | C14—C13—H13A | 120.5 |
N7—C4—C3 | 125.4 (2) | C12—C13—H13A | 120.5 |
N7—C4—C5 | 115.44 (18) | C13—C14—C15 | 120.5 (3) |
C3—C4—C5 | 119.07 (18) | C13—C14—H14A | 119.7 |
C6—C5—C4 | 111.75 (19) | C15—C14—H14A | 119.7 |
C6—C5—H5A | 109.3 | C14—C15—C10 | 121.4 (3) |
C4—C5—H5A | 109.3 | C14—C15—H15A | 119.3 |
C6—C5—H5B | 109.3 | C10—C15—H15A | 119.3 |
C4—C5—H5B | 109.3 | N1—C16—C17 | 115.6 (2) |
H5A—C5—H5B | 107.9 | N1—C16—H16A | 108.4 |
N1—C6—C5 | 111.6 (2) | C17—C16—H16A | 108.4 |
N1—C6—H6A | 109.3 | N1—C16—H16B | 108.4 |
C5—C6—H6A | 109.3 | C17—C16—H16B | 108.4 |
N1—C6—H6B | 109.3 | H16A—C16—H16B | 107.4 |
C5—C6—H6B | 109.3 | C22—C17—C18 | 117.6 (2) |
H6A—C6—H6B | 108.0 | C22—C17—C16 | 123.4 (2) |
C4—N7—C8 | 124.88 (19) | C18—C17—C16 | 118.9 (2) |
C4—N7—H7A | 116.2 (19) | C17—C18—C19 | 120.1 (3) |
C8—N7—H7A | 117.9 (19) | C17—C18—H18A | 119.9 |
N7—C8—C10 | 114.32 (19) | C19—C18—H18A | 119.9 |
N7—C8—C9 | 107.9 (2) | C20—C19—C18 | 121.2 (3) |
C10—C8—C9 | 109.7 (2) | C20—C19—H19A | 119.4 |
N7—C8—H8A | 108.3 | C18—C19—H19A | 119.4 |
C10—C8—H8A | 108.3 | C19—C20—C21 | 118.9 (3) |
C9—C8—H8A | 108.3 | C19—C20—H20A | 120.5 |
C8—C9—H9A | 109.5 | C21—C20—H20A | 120.5 |
C8—C9—H9B | 109.5 | C20—C21—C22 | 120.7 (3) |
H9A—C9—H9B | 109.5 | C20—C21—H21A | 119.6 |
C8—C9—H9C | 109.5 | C22—C21—H21A | 119.6 |
H9A—C9—H9C | 109.5 | C21—C22—C17 | 121.4 (3) |
H9B—C9—H9C | 109.5 | C21—C22—H22A | 119.3 |
C11—C10—C15 | 117.5 (2) | C17—C22—H22A | 119.3 |
C11—C10—C8 | 120.3 (2) | ||
C16—N1—C2—O1 | −0.2 (3) | C15—C10—C11—C12 | −0.4 (5) |
C6—N1—C2—O1 | −168.7 (2) | C8—C10—C11—C12 | 178.2 (3) |
C16—N1—C2—C3 | −178.6 (2) | C10—C11—C12—C13 | 1.0 (6) |
C6—N1—C2—C3 | 13.0 (3) | C11—C12—C13—C14 | −1.1 (6) |
O1—C2—C3—C4 | −164.6 (2) | C12—C13—C14—C15 | 0.5 (5) |
N1—C2—C3—C4 | 13.7 (3) | C13—C14—C15—C10 | 0.1 (4) |
C2—C3—C4—N7 | 169.0 (2) | C11—C10—C15—C14 | −0.2 (4) |
C2—C3—C4—C5 | −7.1 (3) | C8—C10—C15—C14 | −178.7 (2) |
N7—C4—C5—C6 | 160.0 (2) | C2—N1—C16—C17 | −82.3 (3) |
C3—C4—C5—C6 | −23.6 (3) | C6—N1—C16—C17 | 86.1 (3) |
C2—N1—C6—C5 | −43.3 (3) | N1—C16—C17—C22 | 13.3 (3) |
C16—N1—C6—C5 | 148.3 (2) | N1—C16—C17—C18 | −170.5 (2) |
C4—C5—C6—N1 | 46.8 (3) | C22—C17—C18—C19 | 1.1 (4) |
C3—C4—N7—C8 | 6.6 (3) | C16—C17—C18—C19 | −175.3 (3) |
C5—C4—N7—C8 | −177.2 (2) | C17—C18—C19—C20 | −1.4 (6) |
C4—N7—C8—C10 | −64.0 (3) | C18—C19—C20—C21 | 0.6 (6) |
C4—N7—C8—C9 | 173.7 (2) | C19—C20—C21—C22 | 0.4 (5) |
N7—C8—C10—C11 | 155.3 (2) | C20—C21—C22—C17 | −0.7 (5) |
C9—C8—C10—C11 | −83.3 (3) | C18—C17—C22—C21 | −0.1 (4) |
N7—C8—C10—C15 | −26.2 (3) | C16—C17—C22—C21 | 176.1 (3) |
C9—C8—C10—C15 | 95.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7A···O1i | 0.90 (3) | 1.96 (3) | 2.850 (3) | 171 (3) |
Symmetry code: (i) x−1, y+1, z. |