2,3-Di-phenyl-male-imide 1-methyl-pyrrol-idin-2-one monosolvate.

In the title compound, C16H11NO2·C5H9NO, the dihedral angles between the male-imide and phenyl rings are 34.7 (2) and 64.8 (2)°. In the crystal, the 2,3-di-phenyl-male-imide and 1-methyl-pyrrolidin-2-one mol-ecules form centrosymmetrical dimers via pairs of strong N-H⋯O hydrogen bonds and π-π stacking inter-actions between the two neighboring male-imide rings [centroid-centroid distance = 3.495 (2) Å]. The dimers are further linked by weak C-H⋯O and C-H⋯π hydrogen bonds into a three-dimensional framework.

Related literature

For general background to male­imides, see: Yeh et al. (2004 ▶); Billiet et al. (2011 ▶); Zhu et al. (2012 ▶); Parsons & Du Bois (2013 ▶). For the crystal structures of related compounds, see: Zhang et al. (2004 ▶); Mitzi & Afzali (2007 ▶).

Experimental

Crystal data

C16H11NO2·C5H9NO

M = 348.39

Monoclinic,

a = 13.1962 (3) Å

b = 10.0002 (2) Å

c = 13.5600 (3) Å

β = 100.469 (3)°

V = 1759.65 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 170 K

0.54 × 0.40 × 0.24 mm

Data collection

Agilent SuperNova (Single source at offset, Eos) diffractometer

Absorption correction: multi-scan (CrysAlis PRO, Agilent, 2013 ▶) T min = 0.815, T max = 1.000

22206 measured reflections

8818 independent reflections

5708 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.204

S = 1.03

8818 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: CrystalMaker (CrystalMaker, 2011 ▶); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ▶) and SHELXLE (Hübschle et al., 2011 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814002372/kq2011sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002372/kq2011Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002372/kq2011Isup3.cml

CCDC reference: 978501

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H11NO2·C5H9NO	F(000) = 736
Mr = 348.39	Dx = 1.315 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.1962 (3) Å	Cell parameters from 5604 reflections
b = 10.0002 (2) Å	θ = 3.7–36.7°
c = 13.5600 (3) Å	µ = 0.09 mm−1
β = 100.469 (3)°	T = 170 K
V = 1759.65 (7) Å3	Block, colourless
Z = 4	0.54 × 0.40 × 0.24 mm

Agilent SuperNova (Single source at offset, Eos) diffractometer	8818 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	5708 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.028
Detector resolution: 16.0107 pixels mm-1	θmax = 37.5°, θmin = 3.1°
φ scans and ω scans with κ offset	h = −22→22
Absorption correction: multi-scan (CrysAlis PRO, Agilent, 2013)	k = −13→16
Tmin = 0.815, Tmax = 1.000	l = −22→23
22206 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064	H-atom parameters constrained
wR(F2) = 0.204	w = 1/[σ2(Fo2) + (0.0916P)2 + 0.4242P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
8818 reflections	Δρmax = 0.63 e Å−3
236 parameters	Δρmin = −0.30 e Å−3

Experimental. Absorption correction: CrysAlis PRO (Agilent, 2013); Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

	x	y	z	Uiso*/Ueq
O1	0.06128 (8)	0.79304 (9)	0.09092 (7)	0.0333 (2)
O2	0.16449 (8)	0.38928 (10)	−0.01022 (8)	0.0365 (2)
N1	0.10893 (8)	0.60420 (10)	0.01257 (7)	0.0272 (2)
H1	0.1127	0.6383	−0.0465	0.033*
C1	0.13055 (9)	0.47257 (12)	0.04002 (9)	0.0260 (2)
C2	0.10664 (8)	0.45632 (11)	0.14421 (8)	0.0230 (2)
C3	0.12077 (8)	0.33036 (11)	0.20052 (9)	0.0240 (2)
C4	0.09962 (10)	0.20708 (12)	0.15227 (10)	0.0300 (2)
H4	0.0764	0.2042	0.0818	0.036*
C5	0.11244 (11)	0.08926 (13)	0.20683 (12)	0.0366 (3)
H5	0.0982	0.0059	0.1736	0.044*
C6	0.14610 (11)	0.09271 (14)	0.31006 (12)	0.0370 (3)
H6	0.1540	0.0118	0.3473	0.044*
C7	0.16818 (10)	0.21392 (14)	0.35876 (11)	0.0334 (3)
H7	0.1918	0.2160	0.4292	0.040*
C8	0.15569 (9)	0.33222 (13)	0.30448 (9)	0.0275 (2)
H8	0.1709	0.4152	0.3381	0.033*
C9	0.07716 (8)	0.57673 (11)	0.17357 (8)	0.02304 (19)
C10	0.04640 (8)	0.61711 (11)	0.26815 (8)	0.0232 (2)
C11	−0.04123 (10)	0.56355 (15)	0.29686 (10)	0.0324 (3)
H11	−0.0829	0.5013	0.2547	0.039*
C12	−0.06732 (11)	0.60162 (19)	0.38744 (12)	0.0418 (3)
H12	−0.1276	0.5662	0.4067	0.050*
C13	−0.00602 (12)	0.69086 (17)	0.44990 (11)	0.0406 (3)
H13	−0.0241	0.7158	0.5121	0.049*
C14	0.08136 (12)	0.74379 (15)	0.42201 (10)	0.0362 (3)
H14	0.1237	0.8042	0.4653	0.043*
C15	0.10711 (10)	0.70841 (13)	0.33056 (9)	0.0290 (2)
H15	0.1661	0.7465	0.3105	0.035*
C16	0.08056 (9)	0.67456 (12)	0.09100 (9)	0.0254 (2)
O3	0.67483 (9)	0.76077 (11)	0.35649 (9)	0.0429 (3)
N2	0.65279 (9)	0.53588 (12)	0.32844 (9)	0.0348 (2)
C17	0.66039 (10)	0.66246 (14)	0.30065 (11)	0.0333 (3)
C18	0.64860 (19)	0.66600 (18)	0.18720 (12)	0.0554 (5)
H18A	0.5915	0.7263	0.1580	0.066*
H18B	0.7129	0.6983	0.1672	0.066*
C19	0.62610 (16)	0.52685 (18)	0.15209 (12)	0.0483 (4)
H19A	0.6767	0.4966	0.1112	0.058*
H19B	0.5562	0.5208	0.1109	0.058*
C20	0.63358 (14)	0.44090 (16)	0.24659 (13)	0.0447 (4)
H20A	0.5685	0.3917	0.2467	0.054*
H20B	0.6908	0.3758	0.2514	0.054*
C21	0.65804 (14)	0.4951 (2)	0.43134 (12)	0.0479 (4)
H21A	0.5906	0.4613	0.4404	0.072*
H21B	0.6773	0.5719	0.4757	0.072*
H21C	0.7098	0.4244	0.4478	0.072*

	U11	U22	U33	U12	U13	U23
O1	0.0447 (5)	0.0228 (4)	0.0320 (4)	0.0014 (4)	0.0059 (4)	0.0003 (3)
O2	0.0443 (5)	0.0350 (5)	0.0337 (5)	0.0028 (4)	0.0161 (4)	−0.0076 (4)
N1	0.0337 (5)	0.0265 (5)	0.0219 (4)	−0.0021 (4)	0.0062 (4)	−0.0016 (4)
C1	0.0263 (5)	0.0271 (5)	0.0247 (5)	−0.0012 (4)	0.0050 (4)	−0.0041 (4)
C2	0.0235 (4)	0.0221 (5)	0.0232 (4)	−0.0005 (3)	0.0039 (4)	−0.0028 (4)
C3	0.0219 (4)	0.0218 (4)	0.0283 (5)	0.0014 (4)	0.0046 (4)	−0.0026 (4)
C4	0.0304 (5)	0.0230 (5)	0.0355 (6)	0.0006 (4)	0.0028 (5)	−0.0054 (4)
C5	0.0329 (6)	0.0221 (5)	0.0536 (8)	0.0002 (4)	0.0049 (6)	−0.0022 (5)
C6	0.0316 (6)	0.0278 (6)	0.0515 (8)	0.0042 (5)	0.0074 (6)	0.0094 (6)
C7	0.0300 (5)	0.0358 (6)	0.0341 (6)	0.0071 (5)	0.0047 (5)	0.0060 (5)
C8	0.0277 (5)	0.0254 (5)	0.0292 (5)	0.0035 (4)	0.0040 (4)	−0.0002 (4)
C9	0.0242 (4)	0.0219 (4)	0.0230 (4)	−0.0008 (4)	0.0043 (4)	−0.0018 (4)
C10	0.0249 (4)	0.0219 (4)	0.0234 (4)	0.0016 (4)	0.0054 (4)	−0.0007 (4)
C11	0.0268 (5)	0.0382 (7)	0.0331 (6)	−0.0036 (5)	0.0077 (4)	−0.0008 (5)
C12	0.0332 (6)	0.0589 (10)	0.0371 (7)	−0.0004 (6)	0.0163 (5)	0.0034 (7)
C13	0.0460 (8)	0.0513 (9)	0.0275 (6)	0.0078 (6)	0.0148 (6)	−0.0004 (6)
C14	0.0479 (7)	0.0354 (7)	0.0258 (5)	−0.0018 (6)	0.0083 (5)	−0.0061 (5)
C15	0.0345 (6)	0.0270 (5)	0.0264 (5)	−0.0047 (4)	0.0081 (4)	−0.0038 (4)
C16	0.0275 (5)	0.0244 (5)	0.0239 (5)	−0.0018 (4)	0.0036 (4)	−0.0020 (4)
O3	0.0568 (6)	0.0368 (5)	0.0397 (5)	−0.0118 (5)	0.0214 (5)	−0.0127 (4)
N2	0.0366 (5)	0.0342 (6)	0.0347 (6)	−0.0033 (4)	0.0091 (4)	−0.0007 (5)
C17	0.0317 (5)	0.0324 (6)	0.0368 (6)	−0.0018 (5)	0.0085 (5)	−0.0040 (5)
C18	0.0896 (14)	0.0413 (9)	0.0326 (7)	−0.0106 (9)	0.0043 (8)	0.0021 (6)
C19	0.0630 (10)	0.0473 (9)	0.0359 (7)	−0.0088 (8)	0.0126 (7)	−0.0103 (7)
C20	0.0566 (9)	0.0310 (7)	0.0478 (8)	−0.0027 (6)	0.0134 (7)	−0.0093 (6)
C21	0.0487 (8)	0.0598 (10)	0.0359 (7)	−0.0088 (8)	0.0098 (6)	0.0105 (7)

O1—C16	1.2118 (15)	C11—H11	0.9500
O2—C1	1.2121 (15)	C12—C13	1.385 (2)
N1—C16	1.3824 (15)	C12—H12	0.9500
N1—C1	1.3835 (16)	C13—C14	1.383 (2)
N1—H1	0.8800	C13—H13	0.9500
C1—C2	1.5113 (16)	C14—C15	1.3898 (18)
C2—C9	1.3476 (16)	C14—H14	0.9500
C2—C3	1.4672 (16)	C15—H15	0.9500
C3—C4	1.3998 (16)	O3—C17	1.2344 (17)
C3—C8	1.4013 (17)	N2—C17	1.3296 (19)
C4—C5	1.3851 (19)	N2—C21	1.4433 (19)
C4—H4	0.9500	N2—C20	1.448 (2)
C5—C6	1.390 (2)	C17—C18	1.518 (2)
C5—H5	0.9500	C18—C19	1.483 (2)
C6—C7	1.386 (2)	C18—H18A	0.9900
C6—H6	0.9500	C18—H18B	0.9900
C7—C8	1.3872 (18)	C19—C20	1.531 (2)
C7—H7	0.9500	C19—H19A	0.9900
C8—H8	0.9500	C19—H19B	0.9900
C9—C10	1.4703 (15)	C20—H20A	0.9900
C9—C16	1.4936 (16)	C20—H20B	0.9900
C10—C11	1.3926 (17)	C21—H21A	0.9800
C10—C15	1.3947 (16)	C21—H21B	0.9800
C11—C12	1.388 (2)	C21—H21C	0.9800
C16—N1—C1	110.41 (10)	C12—C13—H13	119.9
C16—N1—H1	124.8	C13—C14—C15	119.86 (13)
C1—N1—H1	124.8	C13—C14—H14	120.1
O2—C1—N1	125.57 (12)	C15—C14—H14	120.1
O2—C1—C2	127.79 (12)	C14—C15—C10	120.10 (12)
N1—C1—C2	106.62 (10)	C14—C15—H15	120.0
C9—C2—C3	129.02 (11)	C10—C15—H15	120.0
C9—C2—C1	107.49 (10)	O1—C16—N1	125.67 (12)
C3—C2—C1	123.40 (10)	O1—C16—C9	127.31 (11)
C4—C3—C8	118.88 (11)	N1—C16—C9	107.01 (10)
C4—C3—C2	121.14 (11)	C17—N2—C21	123.38 (14)
C8—C3—C2	119.97 (10)	C17—N2—C20	114.78 (13)
C5—C4—C3	120.32 (13)	C21—N2—C20	121.78 (14)
C5—C4—H4	119.8	O3—C17—N2	126.55 (14)
C3—C4—H4	119.8	O3—C17—C18	125.38 (14)
C4—C5—C6	120.16 (13)	N2—C17—C18	108.07 (13)
C4—C5—H5	119.9	C19—C18—C17	106.32 (14)
C6—C5—H5	119.9	C19—C18—H18A	110.5
C7—C6—C5	120.18 (13)	C17—C18—H18A	110.5
C7—C6—H6	119.9	C19—C18—H18B	110.5
C5—C6—H6	119.9	C17—C18—H18B	110.5
C6—C7—C8	119.91 (13)	H18A—C18—H18B	108.7
C6—C7—H7	120.0	C18—C19—C20	106.22 (13)
C8—C7—H7	120.0	C18—C19—H19A	110.5
C7—C8—C3	120.54 (12)	C20—C19—H19A	110.5
C7—C8—H8	119.7	C18—C19—H19B	110.5
C3—C8—H8	119.7	C20—C19—H19B	110.5
C2—C9—C10	130.04 (11)	H19A—C19—H19B	108.7
C2—C9—C16	108.31 (10)	N2—C20—C19	104.41 (13)
C10—C9—C16	121.64 (10)	N2—C20—H20A	110.9
C11—C10—C15	119.78 (11)	C19—C20—H20A	110.9
C11—C10—C9	120.87 (11)	N2—C20—H20B	110.9
C15—C10—C9	119.33 (10)	C19—C20—H20B	110.9
C12—C11—C10	119.61 (13)	H20A—C20—H20B	108.9
C12—C11—H11	120.2	N2—C21—H21A	109.5
C10—C11—H11	120.2	N2—C21—H21B	109.5
C13—C12—C11	120.44 (13)	H21A—C21—H21B	109.5
C13—C12—H12	119.8	N2—C21—H21C	109.5
C11—C12—H12	119.8	H21A—C21—H21C	109.5
C14—C13—C12	120.19 (13)	H21B—C21—H21C	109.5
C14—C13—H13	119.9

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.88	1.95	2.7800 (15)	156
C5—H5···O1ii	0.95	2.41	3.3639 (17)	179
C21—H21A···O1iii	0.98	2.59	3.498 (2)	154
C21—H21B···O1iv	0.98	2.73	3.436 (2)	129
C15—H15···Cg2v	0.95	2.96	3.8081 (14)	149
C20—H20A···Cg3iii	0.99	2.91	3.6508 (18)	133

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C3–C8 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.88	1.95	2.7800 (15)	156
C5—H5⋯O1ii	0.95	2.41	3.3639 (17)	179
C21—H21A⋯O1iii	0.98	2.59	3.498 (2)	154
C21—H21B⋯O1iv	0.98	2.73	3.436 (2)	129
C15—H15⋯Cg2v	0.95	2.96	3.8081 (14)	149
C20—H20A⋯Cg3iii	0.99	2.91	3.6508 (18)	133

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .