In the title molecule, C
20H
22N
2O
2, the pyridine heterocycle has an envelope conformation and is stabilized as an enamine tautomer. The crystal packing is stabilized by strong intermolecular O—H
O hydrogen bonds, which link the molecules into chains along the
b axis.
Supporting information
CCDC reference: 283787
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.120
- Data-to-parameter ratio = 9.2
checkCIF/PLATON results
No syntax errors found
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 26.25
From the CIF: _reflns_number_total 2080
Count of symmetry unique reflns 2081
Completeness (_total/calc) 99.95%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
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
R)-2-hydroxy-1-phenylethylamino]-5,6-dihydropyridin-2(1
H)-one
top
Crystal data top
C20H22N2O2 | Dx = 1.218 Mg m−3 |
Mr = 322.40 | Melting point: 449 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 68 reflections |
a = 5.5309 (10) Å | θ = 4.6–12.5° |
b = 12.172 (2) Å | µ = 0.08 mm−1 |
c = 26.121 (4) Å | T = 296 K |
V = 1758.5 (5) Å3 | Plate, colourless |
Z = 4 | 0.6 × 0.4 × 0.1 mm |
F(000) = 688 | |
Data collection top
Bruker P4 diffractometer | Rint = 0.061 |
Radiation source: fine-focus sealed tube, FN4 | θmax = 26.3°, θmin = 1.9° |
Graphite monochromator | h = −6→6 |
ω scans | k = −1→15 |
4260 measured reflections | l = −1→32 |
2080 independent reflections | 3 standard reflections every 97 reflections |
1590 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 + difmap |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0628P)2 + 0.1481P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
2080 reflections | Δρmax = 0.18 e Å−3 |
226 parameters | Δρmin = −0.16 e Å−3 |
0 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: 0.027 (3) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.3467 (4) | 0.33046 (16) | 0.14718 (7) | 0.0475 (5) | |
C2 | 0.5061 (5) | 0.27495 (19) | 0.17659 (9) | 0.0465 (6) | |
O1 | 0.6040 (4) | 0.18840 (15) | 0.16118 (7) | 0.0633 (6) | |
C3 | 0.5648 (5) | 0.32040 (18) | 0.22651 (8) | 0.0461 (6) | |
H3A | 0.6485 | 0.2770 | 0.2499 | 0.055* | |
C4 | 0.5017 (5) | 0.42410 (18) | 0.24017 (8) | 0.0412 (5) | |
C5 | 0.3416 (5) | 0.4897 (2) | 0.20548 (9) | 0.0472 (6) | |
H5A | 0.4397 | 0.5393 | 0.1852 | 0.057* | |
H5B | 0.2314 | 0.5336 | 0.2259 | 0.057* | |
C6 | 0.1975 (5) | 0.4154 (2) | 0.17013 (9) | 0.0505 (6) | |
H6A | 0.0678 | 0.3812 | 0.1894 | 0.061* | |
H6B | 0.1251 | 0.4594 | 0.1432 | 0.061* | |
N7 | 0.5878 (5) | 0.47466 (18) | 0.28278 (8) | 0.0483 (6) | |
H7A | 0.545 (8) | 0.541 (3) | 0.2865 (13) | 0.087 (12)* | |
C8 | 0.8128 (5) | 0.44070 (19) | 0.30709 (9) | 0.0456 (6) | |
H8A | 0.9240 | 0.4173 | 0.2800 | 0.055* | |
C9 | 0.9260 (6) | 0.53853 (18) | 0.33407 (9) | 0.0515 (6) | |
H9A | 0.8183 | 0.5643 | 0.3608 | 0.062* | |
H9B | 1.0769 | 0.5163 | 0.3499 | 0.062* | |
O2 | 0.9704 (4) | 0.62498 (15) | 0.29877 (7) | 0.0652 (6) | |
H2 | 1.117 (7) | 0.659 (3) | 0.3132 (12) | 0.083 (11)* | |
C10 | 0.7906 (5) | 0.3468 (2) | 0.34503 (9) | 0.0484 (6) | |
C11 | 0.6045 (6) | 0.3419 (2) | 0.37986 (10) | 0.0652 (8) | |
H11A | 0.4775 | 0.3918 | 0.3780 | 0.078* | |
C12 | 0.6072 (8) | 0.2610 (3) | 0.41833 (14) | 0.0884 (12) | |
H12A | 0.4817 | 0.2571 | 0.4419 | 0.106* | |
C13 | 0.7957 (9) | 0.1877 (3) | 0.42093 (14) | 0.0895 (12) | |
H13A | 0.7987 | 0.1352 | 0.4468 | 0.107* | |
C14 | 0.9771 (8) | 0.1912 (3) | 0.38621 (14) | 0.0842 (11) | |
H14A | 1.1029 | 0.1406 | 0.3880 | 0.101* | |
C15 | 0.9754 (6) | 0.2703 (2) | 0.34804 (12) | 0.0652 (8) | |
H15A | 1.0999 | 0.2720 | 0.3241 | 0.078* | |
C16 | 0.2749 (6) | 0.2890 (2) | 0.09698 (8) | 0.0533 (7) | |
H16A | 0.1012 | 0.2782 | 0.0966 | 0.064* | |
H16B | 0.3506 | 0.2181 | 0.0914 | 0.064* | |
C17 | 0.3441 (5) | 0.3657 (2) | 0.05360 (9) | 0.0453 (6) | |
C18 | 0.2045 (6) | 0.3688 (2) | 0.01002 (9) | 0.0630 (8) | |
H18A | 0.0660 | 0.3257 | 0.0080 | 0.076* | |
C19 | 0.2676 (8) | 0.4350 (3) | −0.03080 (11) | 0.0842 (11) | |
H19A | 0.1728 | 0.4353 | −0.0602 | 0.101* | |
C20 | 0.4686 (8) | 0.5004 (3) | −0.02825 (11) | 0.0791 (10) | |
H20A | 0.5084 | 0.5465 | −0.0554 | 0.095* | |
C21 | 0.6105 (7) | 0.4970 (3) | 0.01475 (12) | 0.0750 (9) | |
H21A | 0.7494 | 0.5399 | 0.0166 | 0.090* | |
C22 | 0.5482 (6) | 0.4300 (3) | 0.05551 (10) | 0.0613 (8) | |
H22A | 0.6456 | 0.4285 | 0.0845 | 0.074* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0596 (13) | 0.0452 (10) | 0.0378 (9) | 0.0071 (11) | −0.0076 (10) | −0.0038 (9) |
C2 | 0.0528 (14) | 0.0404 (12) | 0.0464 (12) | 0.0041 (13) | −0.0069 (12) | −0.0035 (11) |
O1 | 0.0721 (13) | 0.0541 (10) | 0.0638 (11) | 0.0216 (11) | −0.0189 (10) | −0.0223 (9) |
C3 | 0.0586 (16) | 0.0390 (12) | 0.0409 (11) | 0.0063 (13) | −0.0095 (12) | −0.0029 (10) |
C4 | 0.0440 (12) | 0.0405 (12) | 0.0391 (11) | −0.0023 (11) | −0.0023 (11) | 0.0010 (10) |
C5 | 0.0572 (15) | 0.0396 (12) | 0.0448 (12) | 0.0062 (13) | −0.0015 (12) | 0.0005 (10) |
C6 | 0.0544 (15) | 0.0507 (14) | 0.0463 (12) | 0.0099 (13) | −0.0074 (13) | −0.0010 (11) |
N7 | 0.0546 (13) | 0.0424 (11) | 0.0478 (11) | 0.0037 (11) | −0.0085 (10) | −0.0083 (9) |
C8 | 0.0487 (14) | 0.0459 (13) | 0.0421 (11) | −0.0022 (13) | −0.0027 (11) | −0.0031 (11) |
C9 | 0.0595 (15) | 0.0473 (13) | 0.0476 (13) | −0.0105 (14) | −0.0072 (13) | 0.0018 (11) |
O2 | 0.0750 (14) | 0.0571 (11) | 0.0635 (11) | −0.0167 (12) | −0.0125 (12) | 0.0146 (10) |
C10 | 0.0532 (15) | 0.0450 (13) | 0.0469 (13) | −0.0093 (12) | −0.0121 (13) | −0.0037 (11) |
C11 | 0.0643 (18) | 0.0716 (18) | 0.0597 (16) | −0.0092 (17) | −0.0027 (15) | 0.0042 (15) |
C12 | 0.092 (3) | 0.100 (3) | 0.073 (2) | −0.032 (3) | 0.003 (2) | 0.022 (2) |
C13 | 0.102 (3) | 0.076 (2) | 0.090 (2) | −0.030 (3) | −0.032 (2) | 0.031 (2) |
C14 | 0.090 (3) | 0.0579 (18) | 0.105 (3) | −0.005 (2) | −0.031 (2) | 0.0185 (19) |
C15 | 0.0702 (19) | 0.0518 (14) | 0.0736 (17) | −0.0006 (16) | −0.0109 (17) | 0.0023 (14) |
C16 | 0.0659 (17) | 0.0507 (14) | 0.0433 (12) | −0.0023 (15) | −0.0123 (13) | −0.0037 (11) |
C17 | 0.0534 (15) | 0.0452 (12) | 0.0374 (11) | 0.0078 (13) | 0.0002 (12) | −0.0068 (11) |
C18 | 0.0719 (19) | 0.0701 (17) | 0.0470 (13) | −0.0142 (18) | −0.0116 (15) | 0.0002 (14) |
C19 | 0.111 (3) | 0.099 (2) | 0.0427 (14) | −0.022 (3) | −0.0167 (19) | 0.0086 (17) |
C20 | 0.105 (3) | 0.087 (2) | 0.0452 (15) | −0.016 (3) | 0.0179 (18) | −0.0019 (16) |
C21 | 0.073 (2) | 0.083 (2) | 0.0690 (19) | −0.020 (2) | 0.0169 (17) | −0.0087 (17) |
C22 | 0.0559 (16) | 0.0750 (18) | 0.0530 (14) | −0.0081 (17) | −0.0060 (14) | −0.0053 (15) |
Geometric parameters (Å, º) top
N1—C2 | 1.350 (3) | C10—C15 | 1.385 (4) |
N1—C6 | 1.453 (3) | C11—C12 | 1.407 (5) |
N1—C16 | 1.460 (3) | C11—H11A | 0.9300 |
C2—O1 | 1.251 (3) | C12—C13 | 1.374 (6) |
C2—C3 | 1.453 (3) | C12—H12A | 0.9300 |
C3—C4 | 1.357 (3) | C13—C14 | 1.353 (6) |
C3—H3A | 0.9300 | C13—H13A | 0.9300 |
C4—N7 | 1.358 (3) | C14—C15 | 1.386 (4) |
C4—C5 | 1.498 (3) | C14—H14A | 0.9300 |
C5—C6 | 1.518 (3) | C15—H15A | 0.9300 |
C5—H5A | 0.9700 | C16—C17 | 1.518 (3) |
C5—H5B | 0.9700 | C16—H16A | 0.9700 |
C6—H6A | 0.9700 | C16—H16B | 0.9700 |
C6—H6B | 0.9700 | C17—C22 | 1.374 (4) |
N7—C8 | 1.457 (3) | C17—C18 | 1.376 (4) |
N7—H7A | 0.85 (4) | C18—C19 | 1.382 (4) |
C8—C10 | 1.517 (3) | C18—H18A | 0.9300 |
C8—C9 | 1.519 (3) | C19—C20 | 1.368 (5) |
C8—H8A | 0.9800 | C19—H19A | 0.9300 |
C9—O2 | 1.421 (3) | C20—C21 | 1.371 (5) |
C9—H9A | 0.9700 | C20—H20A | 0.9300 |
C9—H9B | 0.9700 | C21—C22 | 1.384 (4) |
O2—H2 | 0.99 (4) | C21—H21A | 0.9300 |
C10—C11 | 1.375 (4) | C22—H22A | 0.9300 |
| | | |
C2—N1—C6 | 119.49 (19) | C11—C10—C8 | 121.7 (3) |
C2—N1—C16 | 121.0 (2) | C15—C10—C8 | 118.9 (3) |
C6—N1—C16 | 117.5 (2) | C10—C11—C12 | 119.7 (3) |
O1—C2—N1 | 121.4 (2) | C10—C11—H11A | 120.1 |
O1—C2—C3 | 120.8 (2) | C12—C11—H11A | 120.1 |
N1—C2—C3 | 117.8 (2) | C13—C12—C11 | 119.8 (4) |
C4—C3—C2 | 122.2 (2) | C13—C12—H12A | 120.1 |
C4—C3—H3A | 118.9 | C11—C12—H12A | 120.1 |
C2—C3—H3A | 118.9 | C14—C13—C12 | 120.6 (3) |
N7—C4—C3 | 123.1 (2) | C14—C13—H13A | 119.7 |
N7—C4—C5 | 117.5 (2) | C12—C13—H13A | 119.7 |
C3—C4—C5 | 119.3 (2) | C13—C14—C15 | 120.0 (4) |
C4—C5—C6 | 111.15 (19) | C13—C14—H14A | 120.0 |
C4—C5—H5A | 109.4 | C15—C14—H14A | 120.0 |
C6—C5—H5A | 109.4 | C10—C15—C14 | 120.9 (3) |
C4—C5—H5B | 109.4 | C10—C15—H15A | 119.6 |
C6—C5—H5B | 109.4 | C14—C15—H15A | 119.6 |
H5A—C5—H5B | 108.0 | N1—C16—C17 | 112.9 (2) |
N1—C6—C5 | 112.1 (2) | N1—C16—H16A | 109.0 |
N1—C6—H6A | 109.2 | C17—C16—H16A | 109.0 |
C5—C6—H6A | 109.2 | N1—C16—H16B | 109.0 |
N1—C6—H6B | 109.2 | C17—C16—H16B | 109.0 |
C5—C6—H6B | 109.2 | H16A—C16—H16B | 107.8 |
H6A—C6—H6B | 107.9 | C22—C17—C18 | 118.4 (3) |
C4—N7—C8 | 121.9 (2) | C22—C17—C16 | 122.0 (2) |
C4—N7—H7A | 115 (3) | C18—C17—C16 | 119.5 (2) |
C8—N7—H7A | 117 (3) | C17—C18—C19 | 120.8 (3) |
N7—C8—C10 | 115.4 (2) | C17—C18—H18A | 119.6 |
N7—C8—C9 | 109.4 (2) | C19—C18—H18A | 119.6 |
C10—C8—C9 | 108.69 (19) | C20—C19—C18 | 120.4 (3) |
N7—C8—H8A | 107.7 | C20—C19—H19A | 119.8 |
C10—C8—H8A | 107.7 | C18—C19—H19A | 119.8 |
C9—C8—H8A | 107.7 | C19—C20—C21 | 119.2 (3) |
O2—C9—C8 | 110.53 (19) | C19—C20—H20A | 120.4 |
O2—C9—H9A | 109.5 | C21—C20—H20A | 120.4 |
C8—C9—H9A | 109.5 | C20—C21—C22 | 120.3 (3) |
O2—C9—H9B | 109.5 | C20—C21—H21A | 119.8 |
C8—C9—H9B | 109.5 | C22—C21—H21A | 119.8 |
H9A—C9—H9B | 108.1 | C17—C22—C21 | 120.8 (3) |
C9—O2—H2 | 102.0 (19) | C17—C22—H22A | 119.6 |
C11—C10—C15 | 119.0 (2) | C21—C22—H22A | 119.6 |
| | | |
C6—N1—C2—O1 | 166.3 (2) | C9—C8—C10—C15 | −92.9 (3) |
C16—N1—C2—O1 | 2.6 (4) | C15—C10—C11—C12 | 1.2 (4) |
C6—N1—C2—C3 | −15.1 (4) | C8—C10—C11—C12 | −172.2 (3) |
C16—N1—C2—C3 | −178.8 (2) | C10—C11—C12—C13 | 0.2 (5) |
O1—C2—C3—C4 | 166.3 (3) | C11—C12—C13—C14 | −1.2 (6) |
N1—C2—C3—C4 | −12.4 (4) | C12—C13—C14—C15 | 0.9 (5) |
C2—C3—C4—N7 | −168.8 (2) | C11—C10—C15—C14 | −1.6 (4) |
C2—C3—C4—C5 | 7.3 (4) | C8—C10—C15—C14 | 172.1 (3) |
N7—C4—C5—C6 | −161.8 (2) | C13—C14—C15—C10 | 0.5 (5) |
C3—C4—C5—C6 | 21.9 (3) | C2—N1—C16—C17 | −117.7 (3) |
C2—N1—C6—C5 | 44.4 (3) | C6—N1—C16—C17 | 78.2 (3) |
C16—N1—C6—C5 | −151.3 (2) | N1—C16—C17—C22 | 32.4 (4) |
C4—C5—C6—N1 | −45.9 (3) | N1—C16—C17—C18 | −150.0 (3) |
C3—C4—N7—C8 | 22.3 (4) | C22—C17—C18—C19 | −0.2 (4) |
C5—C4—N7—C8 | −153.9 (2) | C16—C17—C18—C19 | −177.8 (3) |
C4—N7—C8—C10 | −85.4 (3) | C17—C18—C19—C20 | −1.0 (5) |
C4—N7—C8—C9 | 151.7 (2) | C18—C19—C20—C21 | 1.8 (6) |
N7—C8—C9—O2 | −58.5 (3) | C19—C20—C21—C22 | −1.4 (5) |
C10—C8—C9—O2 | 174.7 (2) | C18—C17—C22—C21 | 0.6 (4) |
N7—C8—C10—C11 | −42.7 (3) | C16—C17—C22—C21 | 178.2 (3) |
C9—C8—C10—C11 | 80.5 (3) | C20—C21—C22—C17 | 0.2 (5) |
N7—C8—C10—C15 | 143.8 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.99 (4) | 1.72 (4) | 2.689 (3) | 167 (3) |
N7—H7A···O1ii | 0.85 (4) | 2.40 (4) | 3.168 (3) | 151 (3) |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2. |