(1SR,3RS,5SR)-3-Hydr­oxy-3-(2-hydroxy­ethyl)-N-phenyl-5-(p-tolyl)­pyrrolidin-2-one

The title compound, C₁₉H₂₁NO₃, is a new functionalized γ-lactam obtained in the cyclo­addition reaction of C-(4-methyl­phen­yl)-N-phenyl­nitrone with tulipalin A. Mol­ecules are connected by O—H...O hydrogen bonds, forming two crossing chain motifs, C(6) and C(7), and generate layers parallel to the (001) plane.

Key indicators

• Single-crystal X-ray study
• T = 180 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.055
• wR factor = 0.170
• Data-to-parameter ratio = 15.6

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED (Oxford Diffraction, 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

(1SR,3RS,5SR)-3-Hydroxy-3-(2-hydroxyethyl)-N-phenyl-5-tolylpyrrolidin-2-one

Crystal data

C19H21NO3	F(000) = 664
Mr = 311.37	Dx = 1.288 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1615 reflections
a = 5.7403 (9) Å	θ = 2.9–32.2°
b = 9.0806 (11) Å	µ = 0.09 mm^−1
c = 30.836 (4) Å	T = 180 K
β = 92.980 (11)°	Needle, colorless
V = 1605.2 (4) Å^3	0.59 × 0.08 × 0.08 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur diffractometer	2044 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.060
Graphite monochromator	θmax = 26.3°, θmin = 3.0°
Detector resolution: 8.2632 pixels mm^-1	h = −5→7
ω and φ scans	k = −11→11
12229 measured reflections	l = −38→38
3291 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.170	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0768P)^2] where P = (Fo^2 + 2Fc^2)/3
3291 reflections	(Δ/σ)max = 0.002
211 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

Experimental. 4a PF=170°C (éthanol), rendement = 60% NMR dans CDCl₃

¹H RMN δ(p.p.m.): 7.32–7.20 (m, 10H, H aromatiques); 5.0 (dd, 1H, J = 6.9 Hz; 8,2 Hz); 4.06 (s, 1H); 4.02 (t, 1H, J = 5.4 Hz); 2.8 (dd, 1H, J = 6.9 Hz; 13.4 Hz); 2.74 (t, 1H, J = 5.4 Hz); 2.2 (dd, 1H, J = 8.2 Hz; 13.4 Hz); 2.1 (m, 2H). ¹³C RMN δ (p.p.m.): 176.8 (C=O); 124 (C3); 60.8 (C5); 59.8 (CH₂O); 44.7(CH₂); 39.2 (C4).

4 b PF=172°C (ethanol), rendement = 60.5% ¹H RMN δ (p.p.m.): 7.0–6.96 (m, 9H, H aromatiques); 5,0 (dd, 1H, J = 6.9 Hz; 8,2 Hz); 3.9 (t, 1H, J = 5.4 Hz); 3.76 (s, 1H); 2.7 (dd,1H, J = 6.9 Hz; 13.4 Hz); 2.66 (t, 1H, J = 5,4 Hz); 2.24 (dd, 1H, J = 8,2 Hz; 13.4 Hz); 2.2 (s, 3H); 2.02 (m, 2H). ¹³C RMN δ (p.p.m.): 176,5 (C=O); 123 (C3); 60.2 (C5); 59,8 (CH₂O); 44,4 (CH₂); 38.8 (C4); 30,2 (CH₃)

4c PF1=164°C(ethanol), rendement = 62% ¹H RMN δ (p.p.m.): 7.34–6.78 (m, 9H, H aromatiques); 5.0 dd, 1H, J = 6.9 Hz; 8,2 Hz); 4.0 (t, 1H, = 5,4 Hz); 3.94 (s, 1H); 3.76 (s, 3H); 2.8 (dd, 1H, J = 6.9 Hz; 13.4 Hz); 2.77 (t, 1H, J = 5,4 Hz), 2.24 (dd, 1H, J = 8,2 Hz; 13.4 Hz); 2.09 (m, 2H). ¹³C RMN δ (p.p.m.): 176,5 (C=O); 124 (C3); 60.2 (C5); 59,8 (CH₂O); 44,4 (CH₂); 38.8 (C4); 55.3 (OCH₃).

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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.4274 (4)	0.4096 (2)	0.65441 (7)	0.0188 (5)
O1	0.7526 (3)	0.3432 (2)	0.69634 (6)	0.0236 (5)
O2	0.7831 (3)	0.6477 (2)	0.70648 (6)	0.0268 (5)
H2	0.7865	0.7229	0.7224	0.040*
O3	0.1805 (3)	0.3870 (2)	0.74263 (6)	0.0257 (5)
H3	0.0441	0.3956	0.7317	0.039*
C1	0.5951 (5)	0.4304 (3)	0.68631 (9)	0.0204 (6)
C2	0.5617 (5)	0.5790 (3)	0.70784 (9)	0.0200 (6)
C3	0.3783 (5)	0.6531 (3)	0.67776 (9)	0.0231 (7)
H3A	0.4528	0.7221	0.6578	0.028*
H3B	0.2661	0.7087	0.6948	0.028*
C4	0.2534 (5)	0.5285 (3)	0.65201 (9)	0.0189 (6)
H4	0.1117	0.4973	0.6672	0.023*
C21	0.4992 (5)	0.5585 (3)	0.75537 (9)	0.0235 (7)
H21A	0.5986	0.4788	0.7681	0.028*
H21B	0.5416	0.6501	0.7713	0.028*
C22	0.2500 (5)	0.5227 (3)	0.76379 (10)	0.0267 (7)
H22A	0.2325	0.5135	0.7954	0.032*
H22B	0.1475	0.6037	0.7528	0.032*
C111	0.3902 (5)	0.2681 (3)	0.63444 (9)	0.0200 (6)
C112	0.5592 (5)	0.2091 (3)	0.60981 (10)	0.0275 (7)
H112	0.6968	0.2638	0.6051	0.033*
C113	0.5300 (6)	0.0695 (4)	0.59164 (11)	0.0339 (8)
H113	0.6470	0.0290	0.5745	0.041*
C114	0.3309 (6)	−0.0095 (3)	0.59858 (10)	0.0327 (8)
H114	0.3102	−0.1051	0.5865	0.039*
C115	0.1618 (6)	0.0509 (3)	0.62322 (10)	0.0324 (8)
H115	0.0246	−0.0040	0.6280	0.039*
C116	0.1880 (5)	0.1902 (3)	0.64113 (10)	0.0270 (7)
H116	0.0693	0.2315	0.6577	0.032*
C411	0.1834 (5)	0.5747 (3)	0.60595 (9)	0.0199 (6)
C412	−0.0339 (5)	0.6402 (3)	0.59822 (10)	0.0271 (7)
H412	−0.1395	0.6463	0.6209	0.033*
C413	−0.0968 (5)	0.6971 (3)	0.55729 (10)	0.0304 (8)
H413	−0.2453	0.7421	0.5525	0.036*
C414	0.0513 (6)	0.6895 (3)	0.52351 (10)	0.0280 (7)
C415	0.2641 (5)	0.6223 (3)	0.53144 (10)	0.0272 (7)
H415	0.3679	0.6142	0.5086	0.033*
C416	0.3305 (5)	0.5662 (3)	0.57196 (9)	0.0243 (7)
H416	0.4793	0.5213	0.5765	0.029*
C417	−0.0190 (6)	0.7536 (4)	0.47962 (10)	0.0451 (9)
H41A	0.0536	0.8505	0.4767	0.068*
H41B	−0.1890	0.7638	0.4769	0.068*
H41C	0.0329	0.6881	0.4568	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0200 (13)	0.0173 (12)	0.0190 (12)	0.0011 (10)	−0.0001 (10)	−0.0023 (10)
O1	0.0205 (11)	0.0217 (11)	0.0281 (11)	0.0033 (9)	−0.0031 (9)	−0.0010 (9)
O2	0.0237 (11)	0.0273 (12)	0.0296 (12)	−0.0059 (9)	0.0032 (9)	−0.0097 (9)
O3	0.0235 (12)	0.0262 (11)	0.0270 (11)	0.0001 (9)	−0.0026 (9)	0.0023 (9)
C1	0.0211 (16)	0.0221 (15)	0.0181 (15)	−0.0030 (13)	0.0020 (13)	0.0011 (13)
C2	0.0181 (15)	0.0188 (14)	0.0230 (15)	−0.0021 (12)	−0.0003 (12)	−0.0014 (12)
C3	0.0269 (17)	0.0218 (15)	0.0203 (15)	0.0028 (13)	−0.0014 (13)	−0.0003 (12)
C4	0.0186 (15)	0.0211 (15)	0.0170 (14)	0.0017 (12)	0.0003 (12)	−0.0001 (12)
C21	0.0242 (16)	0.0264 (16)	0.0198 (15)	0.0013 (14)	−0.0016 (13)	−0.0027 (13)
C22	0.0317 (18)	0.0276 (17)	0.0212 (16)	0.0003 (14)	0.0054 (14)	−0.0044 (13)
C111	0.0236 (16)	0.0172 (14)	0.0186 (14)	−0.0005 (12)	−0.0035 (13)	0.0004 (12)
C112	0.0254 (17)	0.0264 (16)	0.0311 (17)	−0.0019 (14)	0.0050 (14)	−0.0067 (14)
C113	0.0313 (19)	0.0316 (18)	0.0388 (19)	0.0060 (15)	0.0027 (16)	−0.0132 (16)
C114	0.043 (2)	0.0226 (16)	0.0318 (18)	0.0005 (15)	−0.0074 (16)	−0.0063 (14)
C115	0.0327 (19)	0.0279 (17)	0.0364 (19)	−0.0075 (15)	0.0004 (16)	−0.0041 (15)
C116	0.0257 (17)	0.0288 (17)	0.0265 (16)	−0.0030 (14)	0.0001 (14)	−0.0018 (14)
C411	0.0232 (16)	0.0180 (14)	0.0184 (15)	−0.0012 (12)	−0.0006 (12)	−0.0017 (12)
C412	0.0245 (17)	0.0320 (17)	0.0254 (16)	0.0032 (14)	0.0050 (14)	0.0035 (14)
C413	0.0233 (17)	0.0346 (18)	0.0324 (18)	0.0001 (14)	−0.0069 (15)	0.0090 (15)
C414	0.0346 (19)	0.0257 (16)	0.0234 (16)	−0.0096 (14)	−0.0025 (14)	0.0035 (13)
C415	0.0331 (18)	0.0282 (17)	0.0207 (15)	0.0008 (15)	0.0060 (14)	−0.0001 (13)
C416	0.0218 (16)	0.0265 (16)	0.0248 (16)	−0.0006 (13)	0.0021 (13)	−0.0002 (13)
C417	0.055 (2)	0.050 (2)	0.0296 (18)	−0.0068 (19)	−0.0084 (17)	0.0144 (17)

Geometric parameters (Å, º)

N1—C1	1.353 (4)	C112—C113	1.393 (4)
N1—C111	1.436 (3)	C112—H112	0.9500
N1—C4	1.470 (3)	C113—C114	1.375 (4)
O1—C1	1.229 (3)	C113—H113	0.9500
O2—C2	1.419 (3)	C114—C115	1.377 (4)
O2—H2	0.8400	C114—H114	0.9500
O3—C22	1.441 (3)	C115—C116	1.385 (4)
O3—H3	0.8400	C115—H115	0.9500
C1—C2	1.520 (4)	C116—H116	0.9500
C2—C3	1.523 (4)	C411—C416	1.382 (4)
C2—C21	1.538 (4)	C411—C412	1.392 (4)
C3—C4	1.539 (4)	C412—C413	1.394 (4)
C3—H3A	0.9900	C412—H412	0.9500
C3—H3B	0.9900	C413—C414	1.380 (4)
C4—C411	1.515 (4)	C413—H413	0.9500
C4—H4	1.0000	C414—C415	1.376 (4)
C21—C22	1.503 (4)	C414—C417	1.509 (4)
C21—H21A	0.9900	C415—C416	1.384 (4)
C21—H21B	0.9900	C415—H415	0.9500
C22—H22A	0.9900	C416—H416	0.9500
C22—H22B	0.9900	C417—H41A	0.9800
C111—C112	1.372 (4)	C417—H41B	0.9800
C111—C116	1.384 (4)	C417—H41C	0.9800
C1—N1—C111	121.4 (2)	C116—C111—N1	120.0 (2)
C1—N1—C4	113.0 (2)	C111—C112—C113	120.3 (3)
C111—N1—C4	123.4 (2)	C111—C112—H112	119.9
C2—O2—H2	109.5	C113—C112—H112	119.9
C22—O3—H3	109.5	C114—C113—C112	119.7 (3)
O1—C1—N1	125.4 (3)	C114—C113—H113	120.1
O1—C1—C2	124.7 (2)	C112—C113—H113	120.1
N1—C1—C2	109.9 (2)	C113—C114—C115	119.6 (3)
O2—C2—C1	104.1 (2)	C113—C114—H114	120.2
O2—C2—C3	112.3 (2)	C115—C114—H114	120.2
C1—C2—C3	103.0 (2)	C114—C115—C116	121.2 (3)
O2—C2—C21	109.6 (2)	C114—C115—H115	119.4
C1—C2—C21	110.5 (2)	C116—C115—H115	119.4
C3—C2—C21	116.5 (2)	C111—C116—C115	118.8 (3)
C2—C3—C4	106.1 (2)	C111—C116—H116	120.6
C2—C3—H3A	110.5	C115—C116—H116	120.6
C4—C3—H3A	110.5	C416—C411—C412	118.1 (3)
C2—C3—H3B	110.5	C416—C411—C4	123.6 (3)
C4—C3—H3B	110.5	C412—C411—C4	118.1 (3)
H3A—C3—H3B	108.7	C411—C412—C413	120.1 (3)
N1—C4—C411	113.4 (2)	C411—C412—H412	120.0
N1—C4—C3	102.5 (2)	C413—C412—H412	120.0
C411—C4—C3	111.9 (2)	C414—C413—C412	121.6 (3)
N1—C4—H4	109.6	C414—C413—H413	119.2
C411—C4—H4	109.6	C412—C413—H413	119.2
C3—C4—H4	109.6	C415—C414—C413	117.7 (3)
C22—C21—C2	117.5 (2)	C415—C414—C417	121.6 (3)
C22—C21—H21A	107.9	C413—C414—C417	120.7 (3)
C2—C21—H21A	107.9	C414—C415—C416	121.6 (3)
C22—C21—H21B	107.9	C414—C415—H415	119.2
C2—C21—H21B	107.9	C416—C415—H415	119.2
H21A—C21—H21B	107.2	C411—C416—C415	120.9 (3)
O3—C22—C21	110.5 (2)	C411—C416—H416	119.5
O3—C22—H22A	109.6	C415—C416—H416	119.5
C21—C22—H22A	109.6	C414—C417—H41A	109.5
O3—C22—H22B	109.6	C414—C417—H41B	109.5
C21—C22—H22B	109.6	H41A—C417—H41B	109.5
H22A—C22—H22B	108.1	C414—C417—H41C	109.5
C112—C111—C116	120.4 (3)	H41A—C417—H41C	109.5
C112—C111—N1	119.5 (2)	H41B—C417—H41C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1^i	0.84	2.01	2.804 (3)	159
O2—H2···O3^ii	0.84	1.84	2.682 (3)	175

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+3/2.