(–)-1-Benzyl-4-[(1R)-2-hydr­oxy-1-phenyl­ethyl­amino]-5,6-dihydro­pyridin-2(1H)-one

In the title mol­ecule, C₂₀H₂₂N₂O₂, 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.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](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

---

Computing details

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-[(1R)-2-hydroxy-1-phenylethylamino]-5,6-dihydropyridin-2(1H)-one

Crystal data

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) Å^3	Plate, colourless
Z = 4	0.6 × 0.4 × 0.1 mm
F(000) = 688

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: geom + difmap
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.0628P)^2 + 0.1481P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (3)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.99 (4)	1.72 (4)	2.689 (3)	167 (3)
N7—H7A···O1^ii	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.