5-(Diphenyl-methyl-idene)pyrrolidin-2-one.

In the title compound, C(17)H(15)NO, the dihedral angle between the phenyl rings is 80.1 (2)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers.

Related literature

The title compound is a pyrrolidin-2-one derivative. For the preparation of related structures, see: Fujihara & Tomioka (1999 ▶); Enders & Han (2008 ▶). For a related structure containing inter­molecular N—H⋯O=C hydrogen bonds, see: Asiri et al. (2012 ▶).

Experimental

Crystal data

C17H15NO

M = 249.30

Triclinic,

a = 7.135 (2) Å

b = 7.885 (2) Å

c = 12.184 (4) Å

α = 89.76 (3)°

β = 75.09 (3)°

γ = 85.65 (2)°

V = 660.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.70 × 0.50 × 0.35 mm

Data collection

Agilent Xcalibur (Sapphire3, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.542, T max = 1.000

5549 measured reflections

2999 independent reflections

1951 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.225

S = 1.06

2999 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812043851/lh5547sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043851/lh5547Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043851/lh5547Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H15NO	Z = 2
Mr = 249.30	F(000) = 264
Triclinic, P1	Dx = 1.254 Mg m−3
Hall symbol: -P 1	Melting point: 472 K
a = 7.135 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.885 (2) Å	Cell parameters from 1065 reflections
c = 12.184 (4) Å	θ = 3.0–29.0°
α = 89.76 (3)°	µ = 0.08 mm−1
β = 75.09 (3)°	T = 293 K
γ = 85.65 (2)°	Parallelpiped, colourless
V = 660.4 (4) Å3	0.70 × 0.50 × 0.35 mm

Agilent Xcalibur (Sapphire3, Gemini) diffractometer	2999 independent reflections
Radiation source: fine-focus sealed tube	1951 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 16.0690 pixels mm-1	θmax = 29.1°, θmin = 3.0°
ω scans	h = −8→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→10
Tmin = 0.542, Tmax = 1.000	l = −16→16
5549 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.225	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.120P)2] where P = (Fo2 + 2Fc2)/3
2999 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
O	−0.0325 (2)	0.7022 (2)	0.55977 (15)	0.0575 (5)
N	0.2544 (2)	0.5943 (2)	0.44030 (15)	0.0405 (5)
H0A	0.2224	0.4921	0.4353	0.049*
C1	0.1353 (3)	0.7169 (3)	0.50609 (19)	0.0420 (5)
C2	0.2440 (3)	0.8758 (3)	0.4967 (2)	0.0473 (6)
H2A	0.2382	0.9216	0.5714	0.057*
H2B	0.1898	0.9622	0.4543	0.057*
C3	0.4522 (3)	0.8183 (3)	0.4343 (2)	0.0451 (6)
H3A	0.5058	0.8992	0.3766	0.054*
H3B	0.5342	0.8050	0.4865	0.054*
C4	0.4348 (3)	0.6490 (3)	0.38089 (18)	0.0375 (5)
C5	0.5618 (3)	0.5669 (3)	0.29326 (18)	0.0384 (5)
C6	0.5291 (3)	0.3990 (3)	0.24831 (18)	0.0389 (5)
C7	0.3610 (3)	0.3647 (3)	0.2184 (2)	0.0505 (6)
H7A	0.2597	0.4492	0.2276	0.061*
C8	0.3409 (4)	0.2072 (4)	0.1751 (3)	0.0627 (7)
H8A	0.2263	0.1873	0.1560	0.075*
C9	0.4876 (4)	0.0803 (3)	0.1600 (2)	0.0590 (7)
H9A	0.4736	−0.0256	0.1310	0.071*
C10	0.6556 (4)	0.1125 (3)	0.1885 (2)	0.0543 (7)
H10A	0.7564	0.0274	0.1785	0.065*
C11	0.6774 (3)	0.2689 (3)	0.2319 (2)	0.0455 (6)
H11A	0.7927	0.2878	0.2504	0.055*
C12	0.7457 (3)	0.6416 (3)	0.23349 (19)	0.0398 (5)
C13	0.8740 (3)	0.7062 (3)	0.2886 (2)	0.0477 (6)
H13A	0.8460	0.7022	0.3675	0.057*
C14	1.0422 (3)	0.7762 (3)	0.2293 (2)	0.0554 (7)
H14A	1.1248	0.8193	0.2684	0.066*
C15	1.0873 (3)	0.7819 (3)	0.1129 (2)	0.0581 (7)
H15A	1.1997	0.8295	0.0728	0.070*
C16	0.9655 (4)	0.7170 (3)	0.0561 (2)	0.0577 (7)
H16A	0.9962	0.7195	−0.0228	0.069*
C17	0.7963 (3)	0.6473 (3)	0.1157 (2)	0.0499 (6)
H17A	0.7153	0.6036	0.0758	0.060*

	U11	U22	U33	U12	U13	U23
O	0.0476 (10)	0.0429 (10)	0.0693 (12)	−0.0101 (7)	0.0101 (8)	−0.0171 (8)
N	0.0425 (10)	0.0255 (9)	0.0486 (11)	−0.0054 (7)	−0.0022 (8)	−0.0062 (8)
C1	0.0452 (13)	0.0324 (12)	0.0446 (12)	−0.0053 (9)	−0.0039 (10)	−0.0067 (9)
C2	0.0496 (14)	0.0324 (12)	0.0553 (14)	−0.0083 (10)	−0.0036 (10)	−0.0102 (10)
C3	0.0464 (13)	0.0327 (12)	0.0519 (14)	−0.0048 (9)	−0.0045 (10)	−0.0102 (10)
C4	0.0385 (11)	0.0258 (11)	0.0471 (12)	−0.0032 (8)	−0.0089 (9)	−0.0018 (9)
C5	0.0414 (12)	0.0249 (11)	0.0464 (12)	0.0024 (8)	−0.0084 (9)	−0.0025 (9)
C6	0.0439 (12)	0.0270 (11)	0.0409 (11)	0.0011 (8)	−0.0030 (9)	−0.0027 (9)
C7	0.0465 (14)	0.0396 (14)	0.0648 (16)	0.0055 (10)	−0.0153 (11)	−0.0127 (11)
C8	0.0571 (16)	0.0543 (17)	0.0803 (19)	−0.0059 (12)	−0.0232 (14)	−0.0149 (14)
C9	0.0744 (18)	0.0344 (14)	0.0628 (17)	−0.0023 (12)	−0.0083 (13)	−0.0152 (11)
C10	0.0607 (16)	0.0270 (12)	0.0652 (16)	0.0085 (10)	−0.0016 (12)	−0.0015 (11)
C11	0.0450 (13)	0.0302 (12)	0.0581 (14)	0.0008 (9)	−0.0088 (10)	−0.0010 (10)
C12	0.0401 (12)	0.0241 (11)	0.0509 (13)	0.0065 (8)	−0.0062 (9)	−0.0026 (9)
C13	0.0438 (13)	0.0441 (14)	0.0544 (14)	0.0011 (10)	−0.0124 (10)	0.0026 (11)
C14	0.0420 (14)	0.0516 (16)	0.0744 (19)	−0.0060 (11)	−0.0176 (12)	0.0064 (13)
C15	0.0418 (13)	0.0478 (15)	0.0752 (19)	−0.0010 (11)	0.0012 (12)	0.0058 (13)
C16	0.0631 (16)	0.0500 (16)	0.0502 (15)	−0.0026 (12)	0.0026 (12)	−0.0028 (12)
C17	0.0515 (14)	0.0410 (14)	0.0532 (14)	−0.0054 (10)	−0.0055 (11)	−0.0088 (11)

O—C1	1.222 (3)	C8—C9	1.369 (4)
N—C1	1.353 (3)	C8—H8A	0.9300
N—C4	1.404 (3)	C9—C10	1.373 (3)
N—H0A	0.8600	C9—H9A	0.9300
C1—C2	1.512 (3)	C10—C11	1.379 (3)
C2—C3	1.520 (3)	C10—H10A	0.9300
C2—H2A	0.9700	C11—H11A	0.9300
C2—H2B	0.9700	C12—C17	1.389 (3)
C3—C4	1.515 (3)	C12—C13	1.393 (3)
C3—H3A	0.9700	C13—C14	1.385 (3)
C3—H3B	0.9700	C13—H13A	0.9300
C4—C5	1.341 (3)	C14—C15	1.373 (4)
C5—C12	1.490 (3)	C14—H14A	0.9300
C5—C6	1.492 (3)	C15—C16	1.369 (4)
C6—C7	1.386 (3)	C15—H15A	0.9300
C6—C11	1.393 (3)	C16—C17	1.390 (3)
C7—C8	1.383 (4)	C16—H16A	0.9300
C7—H7A	0.9300	C17—H17A	0.9300
C1—N—C4	113.85 (18)	C9—C8—C7	120.8 (2)
C1—N—H0A	123.1	C9—C8—H8A	119.6
C4—N—H0A	123.1	C7—C8—H8A	119.6
O—C1—N	125.5 (2)	C8—C9—C10	118.6 (2)
O—C1—C2	126.6 (2)	C8—C9—H9A	120.7
N—C1—C2	107.83 (19)	C10—C9—H9A	120.7
C1—C2—C3	104.76 (19)	C9—C10—C11	121.1 (2)
C1—C2—H2A	110.8	C9—C10—H10A	119.4
C3—C2—H2A	110.8	C11—C10—H10A	119.4
C1—C2—H2B	110.8	C10—C11—C6	120.9 (2)
C3—C2—H2B	110.8	C10—C11—H11A	119.5
H2A—C2—H2B	108.9	C6—C11—H11A	119.5
C4—C3—C2	103.89 (16)	C17—C12—C13	116.8 (2)
C4—C3—H3A	111.0	C17—C12—C5	119.22 (19)
C2—C3—H3A	111.0	C13—C12—C5	123.9 (2)
C4—C3—H3B	111.0	C14—C13—C12	121.8 (2)
C2—C3—H3B	111.0	C14—C13—H13A	119.1
H3A—C3—H3B	109.0	C12—C13—H13A	119.1
C5—C4—N	125.92 (19)	C15—C14—C13	120.1 (2)
C5—C4—C3	128.01 (19)	C15—C14—H14A	120.0
N—C4—C3	106.06 (18)	C13—C14—H14A	120.0
C4—C5—C12	121.04 (19)	C16—C15—C14	119.5 (2)
C4—C5—C6	123.16 (19)	C16—C15—H15A	120.2
C12—C5—C6	115.79 (19)	C14—C15—H15A	120.2
C7—C6—C11	117.2 (2)	C15—C16—C17	120.5 (2)
C7—C6—C5	124.03 (19)	C15—C16—H16A	119.8
C11—C6—C5	118.74 (18)	C17—C16—H16A	119.8
C8—C7—C6	121.3 (2)	C12—C17—C16	121.3 (2)
C8—C7—H7A	119.4	C12—C17—H17A	119.3
C6—C7—H7A	119.4	C16—C17—H17A	119.3

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···Oi	0.86	2.11	2.921 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯Oi	0.86	2.11	2.921 (2)	157

Symmetry code: (i) .