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

In the title mol­ecule, C₂₀H₂₂N₂O, the pyridine heterocycle has an envelope conformation. The crystal packing is stabilized by inter­molecular N—H...O hydrogen bonds, which link the mol­ecules into chains along the [10] direction.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.090
• Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12    -   C13     ..       5.26 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C12
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C19

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               1757
           Count of symmetry unique reflns         1761
           Completeness (_total/calc)             99.77%
           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
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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-[1(S)-phenylethylamino]-5,6-dihydropyridin-2(1H)-one

Crystal data

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) Å^3	0.48 × 0.40 × 0.16 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: geom and difmap
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.090	w = 1/[σ^2(Fo^2) + (0.0444P)^2 + 0.0309P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/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 (Ų)

	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 (Ų)

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

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)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7A···O1^i	0.90 (3)	1.96 (3)	2.850 (3)	171 (3)

Symmetry code: (i) x−1, y+1, z.