exo-1,7-Dimethyl-4-phenyl-10-oxa-4-aza-tri-cyclo-[5.2.1.0(2,6)]dec-8-ene-3,5-dione.

The title compound, C16H15NO3, consists of an oxabicycle fused to an N-phenyl-substituted pyrrolidine ring anti to the double bond, affording the exo isomer. In the oxabicycle system, the six-membered ring presents a boat conformation, while the heterocyclic rings show envelope conformations with the O atom projected out of the plane. In the crystal, adjacent mol-ecules are linked via weak C-H⋯O hydrogen bonds, forming chains propagating along the a-axis direction. The chains are linked by C-H⋯π inter-actions, forming two-dimensional networks lying parallel to the ac plane.

Related literature

Monomeric norbornene derivatives synthesized by Diels–Alder reactions have attracted great attention due to the attractive optical, thermal, and electrochemical properties of the resulting polymers, see: Choi et al. (2010 ▶); Khosravi & Al-Hajaji (1998 ▶). For related structures, see: Li (2010 ▶, 2011 ▶); Jarosz et al. (2001 ▶).

Experimental

Crystal data

C16H15NO3

M = 269.29

Monoclinic,

a = 8.1267 (6) Å

b = 9.8570 (8) Å

c = 17.2099 (12) Å

β = 93.564 (7)°

V = 1375.93 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.58 × 0.54 × 0.22 mm

Data collection

Agilent Xcalibur (Atlas, Gemini) diffractometer

Absorption correction: analytical (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.958, T max = 0.983

6009 measured reflections

2709 independent reflections

2104 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.101

S = 1.02

2709 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.16 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: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813030262/bh2487sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813030262/bh2487Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813030262/bh2487Isup3.cml

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

C16H15NO3	Dx = 1.3 Mg m−3
Mr = 269.29	Melting point: 401 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.1267 (6) Å	Cell parameters from 1980 reflections
b = 9.8570 (8) Å	θ = 3.4–26.0°
c = 17.2099 (12) Å	µ = 0.09 mm−1
β = 93.564 (7)°	T = 298 K
V = 1375.93 (18) Å3	Block, colourless
Z = 4	0.58 × 0.54 × 0.22 mm
F(000) = 568

Agilent Xcalibur (Atlas, Gemini) diffractometer	2709 independent reflections
Graphite monochromator	2104 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1	Rint = 0.019
ω scans	θmax = 26.1°, θmin = 3.4°
Absorption correction: analytical (CrysAlis PRO; Agilent, 2011)	h = −10→9
Tmin = 0.958, Tmax = 0.983	k = −12→12
6009 measured reflections	l = −21→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0389P)2 + 0.4058P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
2709 reflections	Δρmax = 0.24 e Å−3
184 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.048 (3)
Primary atom site location: structure-invariant direct methods

Experimental. Absorption correction: (CrysAlis PRO; Agilent, 2011) Analytical numeric absorption correction using a multifaceted crystal model

	x	y	z	Uiso*/Ueq
C2	0.89127 (19)	0.24866 (16)	0.65338 (8)	0.0379 (4)
C3	0.81574 (19)	0.27178 (15)	0.73016 (8)	0.0375 (4)
H3	0.7482	0.3542	0.7296	0.045*
C4	0.72028 (18)	0.14469 (16)	0.75948 (8)	0.0372 (4)
C5	0.6482 (2)	0.19228 (18)	0.83406 (9)	0.0472 (4)
H5	0.5382	0.2114	0.8413	0.057*
C6	0.7726 (2)	0.20099 (18)	0.88640 (9)	0.0484 (4)
H6	0.7676	0.2279	0.938	0.058*
C7	0.92630 (19)	0.15872 (16)	0.84656 (8)	0.0386 (4)
C8	0.96335 (19)	0.27970 (16)	0.79084 (8)	0.0379 (4)
H8	0.9688	0.367	0.8181	0.045*
C9	1.1131 (2)	0.25456 (16)	0.74554 (9)	0.0393 (4)
C10	0.6092 (2)	0.06732 (19)	0.70213 (9)	0.0486 (4)
H10A	0.6726	0.033	0.6612	0.073*
H10B	0.5245	0.1265	0.6805	0.073*
H10C	0.5597	−0.007	0.7281	0.073*
C12	1.0660 (2)	0.0990 (2)	0.89652 (9)	0.0533 (5)
H12A	1.027	0.022	0.9242	0.08*
H12B	1.1084	0.1658	0.933	0.08*
H12C	1.1519	0.0708	0.8642	0.08*
C15	1.17344 (18)	0.21261 (16)	0.60751 (8)	0.0377 (4)
C16	1.1598 (2)	0.09518 (17)	0.56431 (9)	0.0478 (4)
H16	1.078	0.0322	0.5734	0.057*
C17	1.2689 (2)	0.07181 (19)	0.50718 (10)	0.0556 (5)
H17	1.2603	−0.0072	0.4776	0.067*
C18	1.3896 (2)	0.1645 (2)	0.49394 (10)	0.0543 (5)
H18	1.4629	0.1482	0.4556	0.065*
C19	1.4025 (2)	0.2812 (2)	0.53705 (10)	0.0521 (5)
H19	1.4848	0.3437	0.528	0.063*
C20	1.29349 (19)	0.30661 (18)	0.59406 (9)	0.0442 (4)
H20	1.3014	0.3863	0.6229	0.053*
O11	0.85844 (12)	0.06324 (10)	0.78944 (5)	0.0362 (3)
O13	0.82053 (14)	0.24123 (13)	0.58982 (6)	0.0525 (3)
O14	1.25472 (14)	0.24824 (14)	0.77023 (7)	0.0556 (4)
N1	1.06138 (15)	0.23679 (13)	0.66731 (7)	0.0381 (3)

	U11	U22	U33	U12	U13	U23
C2	0.0386 (8)	0.0413 (8)	0.0339 (8)	0.0014 (7)	0.0028 (6)	0.0026 (7)
C3	0.0374 (8)	0.0387 (8)	0.0365 (8)	0.0073 (7)	0.0044 (6)	−0.0010 (6)
C4	0.0337 (8)	0.0440 (9)	0.0340 (7)	0.0042 (7)	0.0029 (6)	0.0002 (7)
C5	0.0426 (9)	0.0590 (10)	0.0413 (9)	0.0037 (8)	0.0123 (7)	−0.0020 (8)
C6	0.0583 (11)	0.0552 (10)	0.0332 (8)	−0.0037 (9)	0.0136 (7)	−0.0068 (7)
C7	0.0443 (9)	0.0430 (9)	0.0284 (7)	−0.0022 (7)	0.0001 (6)	−0.0049 (6)
C8	0.0444 (9)	0.0363 (8)	0.0332 (7)	0.0005 (7)	0.0041 (6)	−0.0068 (6)
C9	0.0407 (9)	0.0407 (8)	0.0363 (8)	−0.0026 (7)	0.0006 (7)	−0.0007 (7)
C10	0.0407 (9)	0.0615 (11)	0.0430 (9)	−0.0035 (8)	−0.0035 (7)	−0.0006 (8)
C12	0.0558 (11)	0.0633 (12)	0.0390 (9)	−0.0051 (9)	−0.0111 (8)	0.0054 (8)
C15	0.0360 (8)	0.0449 (9)	0.0326 (7)	0.0037 (7)	0.0046 (6)	0.0018 (7)
C16	0.0544 (10)	0.0455 (9)	0.0448 (9)	−0.0038 (8)	0.0129 (8)	−0.0010 (8)
C17	0.0689 (12)	0.0526 (11)	0.0469 (10)	0.0084 (10)	0.0167 (9)	−0.0054 (8)
C18	0.0504 (11)	0.0691 (13)	0.0454 (9)	0.0155 (9)	0.0176 (8)	0.0068 (9)
C19	0.0401 (9)	0.0626 (12)	0.0544 (10)	−0.0001 (8)	0.0095 (8)	0.0137 (9)
C20	0.0397 (9)	0.0474 (9)	0.0457 (9)	−0.0005 (8)	0.0038 (7)	0.0006 (8)
O11	0.0379 (6)	0.0376 (6)	0.0327 (5)	0.0011 (5)	−0.0021 (4)	−0.0027 (4)
O13	0.0456 (7)	0.0792 (9)	0.0323 (6)	0.0025 (6)	−0.0016 (5)	0.0041 (6)
O14	0.0395 (7)	0.0805 (9)	0.0462 (7)	−0.0041 (6)	−0.0029 (5)	0.0001 (6)
N1	0.0358 (7)	0.0472 (8)	0.0317 (6)	0.0004 (6)	0.0051 (5)	−0.0022 (5)

C2—O13	1.2059 (18)	C9—N1	1.3962 (19)
C2—N1	1.3932 (19)	C10—H10A	0.96
C2—C3	1.508 (2)	C10—H10B	0.96
C3—C8	1.543 (2)	C10—H10C	0.96
C3—C4	1.573 (2)	C12—H12A	0.96
C3—H3	0.98	C12—H12B	0.96
C4—O11	1.4488 (17)	C12—H12C	0.96
C4—C10	1.503 (2)	C15—C20	1.375 (2)
C4—C5	1.518 (2)	C15—C16	1.376 (2)
C5—C6	1.314 (2)	C15—N1	1.4359 (18)
C5—H5	0.93	C16—C17	1.384 (2)
C6—C7	1.520 (2)	C16—H16	0.93
C6—H6	0.93	C17—C18	1.370 (3)
C7—O11	1.4454 (17)	C17—H17	0.93
C7—C12	1.501 (2)	C18—C19	1.369 (3)
C7—C8	1.571 (2)	C18—H18	0.93
C8—C9	1.506 (2)	C19—C20	1.385 (2)
C8—H8	0.98	C19—H19	0.93
C9—O14	1.2036 (19)	C20—H20	0.93
O13—C2—N1	124.26 (14)	N1—C9—C8	108.39 (13)
O13—C2—C3	127.35 (14)	C4—C10—H10A	109.5
N1—C2—C3	108.39 (12)	C4—C10—H10B	109.5
C2—C3—C8	105.01 (12)	H10A—C10—H10B	109.5
C2—C3—C4	113.35 (12)	C4—C10—H10C	109.5
C8—C3—C4	101.62 (11)	H10A—C10—H10C	109.5
C2—C3—H3	112.1	H10B—C10—H10C	109.5
C8—C3—H3	112.1	C7—C12—H12A	109.5
C4—C3—H3	112.1	C7—C12—H12B	109.5
O11—C4—C10	111.89 (13)	H12A—C12—H12B	109.5
O11—C4—C5	101.62 (11)	C7—C12—H12C	109.5
C10—C4—C5	117.68 (13)	H12A—C12—H12C	109.5
O11—C4—C3	99.72 (11)	H12B—C12—H12C	109.5
C10—C4—C3	118.77 (12)	C20—C15—C16	120.66 (14)
C5—C4—C3	104.42 (13)	C20—C15—N1	119.79 (14)
C6—C5—C4	106.20 (14)	C16—C15—N1	119.55 (14)
C6—C5—H5	126.9	C15—C16—C17	119.34 (16)
C4—C5—H5	126.9	C15—C16—H16	120.3
C5—C6—C7	106.95 (14)	C17—C16—H16	120.3
C5—C6—H6	126.5	C18—C17—C16	120.28 (17)
C7—C6—H6	126.5	C18—C17—H17	119.9
O11—C7—C12	112.15 (13)	C16—C17—H17	119.9
O11—C7—C6	101.30 (12)	C19—C18—C17	120.12 (16)
C12—C7—C6	117.55 (13)	C19—C18—H18	119.9
O11—C7—C8	99.13 (11)	C17—C18—H18	119.9
C12—C7—C8	118.73 (14)	C18—C19—C20	120.32 (17)
C6—C7—C8	105.15 (13)	C18—C19—H19	119.8
C9—C8—C3	105.10 (12)	C20—C19—H19	119.8
C9—C8—C7	112.51 (13)	C15—C20—C19	119.28 (16)
C3—C8—C7	101.79 (12)	C15—C20—H20	120.4
C9—C8—H8	112.3	C19—C20—H20	120.4
C3—C8—H8	112.3	C7—O11—C4	97.80 (11)
C7—C8—H8	112.3	C2—N1—C9	113.03 (12)
O14—C9—N1	123.91 (14)	C2—N1—C15	123.87 (12)
O14—C9—C8	127.69 (14)	C9—N1—C15	123.07 (13)
O13—C2—C3—C8	−177.05 (16)	C3—C8—C9—N1	1.13 (16)
N1—C2—C3—C8	2.91 (16)	C7—C8—C9—N1	111.06 (14)
O13—C2—C3—C4	72.9 (2)	C20—C15—C16—C17	0.4 (2)
N1—C2—C3—C4	−107.14 (14)	N1—C15—C16—C17	−179.47 (15)
C2—C3—C4—O11	78.04 (14)	C15—C16—C17—C18	0.2 (3)
C8—C3—C4—O11	−34.09 (12)	C16—C17—C18—C19	−0.3 (3)
C2—C3—C4—C10	−43.66 (18)	C17—C18—C19—C20	−0.2 (3)
C8—C3—C4—C10	−155.80 (13)	C16—C15—C20—C19	−0.8 (2)
C2—C3—C4—C5	−177.18 (13)	N1—C15—C20—C19	179.01 (14)
C8—C3—C4—C5	70.69 (14)	C18—C19—C20—C15	0.7 (2)
O11—C4—C5—C6	30.57 (17)	C12—C7—O11—C4	173.54 (12)
C10—C4—C5—C6	153.10 (16)	C6—C7—O11—C4	47.34 (13)
C3—C4—C5—C6	−72.78 (16)	C8—C7—O11—C4	−60.23 (12)
C4—C5—C6—C7	−0.22 (19)	C10—C4—O11—C7	−174.15 (12)
C5—C6—C7—O11	−30.23 (17)	C5—C4—O11—C7	−47.72 (13)
C5—C6—C7—C12	−152.76 (16)	C3—C4—O11—C7	59.33 (12)
C5—C6—C7—C8	72.58 (17)	O13—C2—N1—C9	177.59 (15)
C2—C3—C8—C9	−2.40 (16)	C3—C2—N1—C9	−2.37 (18)
C4—C3—C8—C9	115.90 (12)	O13—C2—N1—C15	−0.8 (3)
C2—C3—C8—C7	−119.87 (12)	C3—C2—N1—C15	179.28 (13)
C4—C3—C8—C7	−1.57 (13)	O14—C9—N1—C2	179.87 (15)
O11—C7—C8—C9	−75.16 (14)	C8—C9—N1—C2	0.75 (18)
C12—C7—C8—C9	46.41 (18)	O14—C9—N1—C15	−1.8 (2)
C6—C7—C8—C9	−179.58 (12)	C8—C9—N1—C15	179.11 (13)
O11—C7—C8—C3	36.83 (13)	C20—C15—N1—C2	118.53 (17)
C12—C7—C8—C3	158.40 (13)	C16—C15—N1—C2	−61.6 (2)
C6—C7—C8—C3	−67.59 (14)	C20—C15—N1—C9	−59.6 (2)
C3—C8—C9—O14	−177.95 (16)	C16—C15—N1—C9	120.18 (17)
C7—C8—C9—O14	−68.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O14i	0.93	2.57	3.362 (2)	144
C10—H10B···Cg1i	0.96	2.95	3.8029	148
C12—H12B···Cg1ii	0.96	2.79	3.7287	167

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15–C20 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O14i	0.93	2.57	3.362 (2)	144
C10—H10B⋯Cg1i	0.96	2.95	3.8029	148
C12—H12B⋯Cg1ii	0.96	2.79	3.7287	167

Symmetry codes: (i) ; (ii) .