Crystal structure of 14-methyl-11-(3-methyl-phen-yl)-12-oxa-8,14-di-aza-tetra-cyclo-[8.3.3.0(1,10).0(2,7)]hexa-deca-2(7),3,5-triene-9,13-dione.

In the title compound, C21H20N2O3, the lactone ring adopts an envelope conformation with the quaternary C atom bonded to two other C atoms as the flap. The fused pyrrolidine ring adopts a twisted conformation about the Cq-N (q = quaternary) bond. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R 2 (2)(8) loops. The dimers are linked into [110] chains by pairs of C-H⋯O inter-actions, which generate R 2 (2)(14) loops.

Related literature

For related structures, see: Ramesh et al. (2008 ▸); Zhao & Teng (2008 ▸); Bai et al. (2009 ▸); Du et al. (2010 ▸); Wang et al. (2010 ▸). For puckering parameters, see: Cremer & Pople (1975 ▸).

Experimental

Crystal data

C21H20N2O3

M = 348.39

Monoclinic,

a = 10.4772 (7) Å

b = 8.6834 (6) Å

c = 19.1123 (13) Å

β = 92.490 (2)°

V = 1737.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.35 × 0.30 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.969, T max = 0.974

25650 measured reflections

3787 independent reflections

2875 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.137

S = 1.09

3787 reflections

239 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAINT; 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 ▸); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015008129/hb7360sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015008129/hb7360Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015008129/hb7360Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015008129/hb7360fig1.tif

The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015008129/hb7360fig2.tif

The mol­ecular packing is viewed along the b axis. Dashed lines shows the inter­molecular C-H⋯O and N-H⋯O hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted for clarity.

CCDC reference: 1061495

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

C21H20N2O3	F(000) = 736
Mr = 348.39	Dx = 1.332 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3787 reflections
a = 10.4772 (7) Å	θ = 2.1–27.0°
b = 8.6834 (6) Å	µ = 0.09 mm−1
c = 19.1123 (13) Å	T = 293 K
β = 92.490 (2)°	Block, colourless
V = 1737.2 (2) Å3	0.35 × 0.30 × 0.30 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3787 independent reflections
Radiation source: fine-focus sealed tube	2875 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω and φ scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→13
Tmin = 0.969, Tmax = 0.974	k = −11→11
25650 measured reflections	l = −24→24

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0557P)2 + 0.7606P] where P = (Fo2 + 2Fc2)/3
3787 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.05279 (11)	0.22692 (16)	0.53826 (6)	0.0458 (3)
O3	0.43975 (13)	0.34579 (16)	0.45820 (6)	0.0505 (4)
O2	0.04279 (13)	0.03341 (17)	0.61440 (7)	0.0557 (4)
N1	0.32532 (15)	−0.00285 (17)	0.57673 (7)	0.0427 (4)
N2	0.43155 (15)	0.38257 (19)	0.57461 (8)	0.0454 (4)
C9	0.25355 (16)	0.13927 (19)	0.58542 (8)	0.0342 (4)
C7	0.15071 (16)	0.32733 (19)	0.51218 (8)	0.0368 (4)
H7	0.1649	0.4112	0.5459	0.044*
C10	0.27021 (15)	0.22222 (19)	0.51571 (8)	0.0334 (4)
C13	0.29625 (17)	0.2330 (2)	0.64871 (8)	0.0381 (4)
C19	0.38880 (16)	0.3193 (2)	0.51367 (8)	0.0378 (4)
C18	0.38303 (17)	0.3521 (2)	0.64055 (9)	0.0404 (4)
C11	0.27058 (18)	0.0894 (2)	0.46208 (9)	0.0401 (4)
H11A	0.1898	0.0847	0.4353	0.048*
H11B	0.3389	0.1028	0.4300	0.048*
C14	0.2508 (2)	0.2060 (3)	0.71465 (9)	0.0522 (5)
H14	0.1914	0.1280	0.7206	0.063*
C6	0.11100 (17)	0.3972 (2)	0.44276 (9)	0.0400 (4)
C1	0.17662 (19)	0.5259 (2)	0.42071 (9)	0.0436 (4)
H1	0.2427	0.5654	0.4494	0.052*
C8	0.10628 (17)	0.1232 (2)	0.58346 (9)	0.0403 (4)
C12	0.2914 (2)	−0.0568 (2)	0.50569 (10)	0.0496 (5)
H12A	0.2141	−0.1184	0.5052	0.059*
H12B	0.3598	−0.1184	0.4876	0.059*
C2	0.1465 (2)	0.5974 (2)	0.35712 (9)	0.0483 (5)
C17	0.4237 (2)	0.4417 (2)	0.69755 (10)	0.0534 (5)
H17	0.4813	0.5217	0.6918	0.064*
C5	0.0112 (2)	0.3400 (2)	0.40112 (10)	0.0530 (5)
H5	−0.0334	0.2535	0.4150	0.064*
C3	0.0451 (2)	0.5388 (3)	0.31651 (10)	0.0568 (5)
H3	0.0221	0.5854	0.2740	0.068*
C16	0.3779 (2)	0.4109 (3)	0.76275 (10)	0.0624 (6)
H16	0.4051	0.4704	0.8010	0.075*
C20	0.2201 (3)	0.7356 (3)	0.33399 (12)	0.0682 (6)
H20A	0.1865	0.7692	0.2890	0.102*
H20B	0.3085	0.7086	0.3307	0.102*
H20C	0.2123	0.8171	0.3674	0.102*
C4	−0.0220 (2)	0.4130 (3)	0.33825 (11)	0.0627 (6)
H4	−0.0905	0.3761	0.3105	0.075*
C15	0.2922 (2)	0.2928 (3)	0.77163 (10)	0.0639 (6)
H15	0.2624	0.2719	0.8158	0.077*
C21	0.3205 (2)	−0.1220 (2)	0.63015 (11)	0.0571 (5)
H21A	0.3721	−0.2079	0.6171	0.086*
H21B	0.2338	−0.1553	0.6343	0.086*
H21C	0.3524	−0.0814	0.6742	0.086*
H2A	0.488 (2)	0.461 (3)	0.5713 (11)	0.058 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0362 (6)	0.0560 (8)	0.0455 (7)	−0.0010 (6)	0.0058 (5)	0.0056 (6)
O3	0.0578 (8)	0.0531 (8)	0.0422 (7)	−0.0136 (6)	0.0208 (6)	−0.0003 (6)
O2	0.0497 (8)	0.0598 (9)	0.0586 (8)	−0.0169 (7)	0.0140 (6)	0.0077 (7)
N1	0.0495 (9)	0.0392 (8)	0.0393 (8)	0.0024 (7)	0.0011 (6)	0.0039 (6)
N2	0.0459 (9)	0.0520 (9)	0.0384 (8)	−0.0206 (8)	0.0050 (6)	0.0006 (7)
C9	0.0368 (9)	0.0367 (8)	0.0294 (7)	−0.0049 (7)	0.0052 (6)	0.0018 (6)
C7	0.0386 (9)	0.0372 (9)	0.0350 (8)	−0.0003 (7)	0.0050 (7)	−0.0011 (7)
C10	0.0368 (8)	0.0365 (9)	0.0273 (7)	−0.0028 (7)	0.0051 (6)	−0.0004 (6)
C13	0.0397 (9)	0.0444 (9)	0.0306 (8)	−0.0034 (7)	0.0040 (7)	0.0009 (7)
C19	0.0403 (9)	0.0380 (9)	0.0356 (8)	−0.0039 (7)	0.0085 (7)	0.0025 (7)
C18	0.0421 (9)	0.0465 (10)	0.0326 (8)	−0.0052 (8)	0.0014 (7)	−0.0011 (7)
C11	0.0482 (10)	0.0398 (9)	0.0325 (8)	−0.0019 (8)	0.0048 (7)	−0.0033 (7)
C14	0.0586 (12)	0.0651 (13)	0.0335 (9)	−0.0121 (10)	0.0087 (8)	0.0021 (8)
C6	0.0464 (10)	0.0385 (9)	0.0349 (8)	0.0074 (8)	0.0008 (7)	−0.0044 (7)
C1	0.0537 (11)	0.0389 (9)	0.0378 (9)	0.0048 (8)	−0.0012 (8)	−0.0021 (7)
C8	0.0418 (9)	0.0436 (10)	0.0360 (8)	−0.0073 (8)	0.0067 (7)	−0.0022 (7)
C12	0.0635 (12)	0.0413 (10)	0.0439 (10)	0.0054 (9)	0.0022 (9)	−0.0039 (8)
C2	0.0645 (12)	0.0422 (10)	0.0385 (9)	0.0111 (9)	0.0053 (8)	−0.0008 (8)
C17	0.0569 (12)	0.0552 (12)	0.0475 (11)	−0.0128 (10)	−0.0047 (9)	−0.0069 (9)
C5	0.0566 (12)	0.0515 (11)	0.0500 (11)	−0.0028 (9)	−0.0066 (9)	−0.0009 (9)
C3	0.0751 (14)	0.0579 (12)	0.0368 (10)	0.0158 (11)	−0.0030 (9)	0.0020 (9)
C16	0.0726 (15)	0.0767 (15)	0.0374 (10)	−0.0030 (12)	−0.0059 (9)	−0.0158 (10)
C20	0.0925 (18)	0.0582 (13)	0.0540 (12)	0.0012 (12)	0.0053 (12)	0.0138 (10)
C4	0.0667 (14)	0.0691 (15)	0.0507 (12)	0.0009 (12)	−0.0169 (10)	−0.0063 (11)
C15	0.0738 (15)	0.0882 (17)	0.0303 (9)	−0.0080 (13)	0.0075 (9)	−0.0051 (10)
C21	0.0636 (13)	0.0513 (12)	0.0559 (12)	0.0000 (10)	−0.0032 (10)	0.0159 (9)

O1—C8	1.353 (2)	C14—H14	0.9300
O1—C7	1.451 (2)	C6—C5	1.378 (3)
O3—C19	1.2292 (19)	C6—C1	1.387 (3)
O2—C8	1.197 (2)	C1—C2	1.389 (2)
N1—C21	1.456 (2)	C1—H1	0.9300
N1—C9	1.458 (2)	C12—H12A	0.9700
N1—C12	1.465 (2)	C12—H12B	0.9700
N2—C19	1.347 (2)	C2—C3	1.385 (3)
N2—C18	1.404 (2)	C2—C20	1.503 (3)
N2—H2A	0.91 (2)	C17—C16	1.381 (3)
C9—C13	1.510 (2)	C17—H17	0.9300
C9—C10	1.531 (2)	C5—C4	1.389 (3)
C9—C8	1.548 (2)	C5—H5	0.9300
C7—C6	1.501 (2)	C3—C4	1.374 (3)
C7—C10	1.548 (2)	C3—H3	0.9300
C7—H7	0.9800	C16—C15	1.378 (3)
C10—C19	1.504 (2)	C16—H16	0.9300
C10—C11	1.543 (2)	C20—H20A	0.9600
C13—C14	1.386 (2)	C20—H20B	0.9600
C13—C18	1.390 (2)	C20—H20C	0.9600
C18—C17	1.390 (2)	C4—H4	0.9300
C11—C12	1.529 (3)	C15—H15	0.9300
C11—H11A	0.9700	C21—H21A	0.9600
C11—H11B	0.9700	C21—H21B	0.9600
C14—C15	1.379 (3)	C21—H21C	0.9600
C8—O1—C7	109.89 (13)	C6—C1—C2	121.97 (18)
C21—N1—C9	119.19 (15)	C6—C1—H1	119.0
C21—N1—C12	114.09 (16)	C2—C1—H1	119.0
C9—N1—C12	105.69 (13)	O2—C8—O1	121.69 (17)
C19—N2—C18	125.42 (15)	O2—C8—C9	128.41 (17)
C19—N2—H2A	116.1 (14)	O1—C8—C9	109.88 (14)
C18—N2—H2A	117.9 (14)	N1—C12—C11	105.24 (14)
N1—C9—C13	114.29 (14)	N1—C12—H12A	110.7
N1—C9—C10	102.71 (12)	C11—C12—H12A	110.7
C13—C9—C10	113.74 (13)	N1—C12—H12B	110.7
N1—C9—C8	116.04 (14)	C11—C12—H12B	110.7
C13—C9—C8	109.18 (13)	H12A—C12—H12B	108.8
C10—C9—C8	99.93 (13)	C3—C2—C1	117.75 (19)
O1—C7—C6	111.93 (14)	C3—C2—C20	121.27 (18)
O1—C7—C10	102.31 (13)	C1—C2—C20	120.97 (19)
C6—C7—C10	117.98 (13)	C16—C17—C18	119.49 (19)
O1—C7—H7	108.1	C16—C17—H17	120.3
C6—C7—H7	108.1	C18—C17—H17	120.3
C10—C7—H7	108.1	C6—C5—C4	119.4 (2)
C19—C10—C9	114.33 (13)	C6—C5—H5	120.3
C19—C10—C11	112.09 (13)	C4—C5—H5	120.3
C9—C10—C11	103.29 (13)	C4—C3—C2	120.85 (19)
C19—C10—C7	109.63 (14)	C4—C3—H3	119.6
C9—C10—C7	101.11 (12)	C2—C3—H3	119.6
C11—C10—C7	115.91 (14)	C15—C16—C17	120.59 (19)
C14—C13—C18	118.69 (16)	C15—C16—H16	119.7
C14—C13—C9	122.39 (16)	C17—C16—H16	119.7
C18—C13—C9	118.92 (14)	C2—C20—H20A	109.5
O3—C19—N2	121.95 (16)	C2—C20—H20B	109.5
O3—C19—C10	121.17 (15)	H20A—C20—H20B	109.5
N2—C19—C10	116.77 (14)	C2—C20—H20C	109.5
C13—C18—C17	120.52 (16)	H20A—C20—H20C	109.5
C13—C18—N2	120.33 (15)	H20B—C20—H20C	109.5
C17—C18—N2	119.15 (17)	C3—C4—C5	120.8 (2)
C12—C11—C10	105.24 (13)	C3—C4—H4	119.6
C12—C11—H11A	110.7	C5—C4—H4	119.6
C10—C11—H11A	110.7	C16—C15—C14	119.58 (19)
C12—C11—H11B	110.7	C16—C15—H15	120.2
C10—C11—H11B	110.7	C14—C15—H15	120.2
H11A—C11—H11B	108.8	N1—C21—H21A	109.5
C15—C14—C13	121.12 (19)	N1—C21—H21B	109.5
C15—C14—H14	119.4	H21A—C21—H21B	109.5
C13—C14—H14	119.4	N1—C21—H21C	109.5
C5—C6—C1	119.21 (17)	H21A—C21—H21C	109.5
C5—C6—C7	122.61 (17)	H21B—C21—H21C	109.5
C1—C6—C7	118.17 (16)
C21—N1—C9—C13	63.0 (2)	C14—C13—C18—N2	179.77 (18)
C12—N1—C9—C13	−167.01 (14)	C9—C13—C18—N2	−1.1 (3)
C21—N1—C9—C10	−173.31 (15)	C19—N2—C18—C13	9.7 (3)
C12—N1—C9—C10	−43.33 (17)	C19—N2—C18—C17	−170.84 (18)
C21—N1—C9—C8	−65.4 (2)	C19—C10—C11—C12	108.42 (17)
C12—N1—C9—C8	64.55 (18)	C9—C10—C11—C12	−15.13 (18)
C8—O1—C7—C6	156.13 (14)	C7—C10—C11—C12	−124.70 (16)
C8—O1—C7—C10	28.85 (16)	C18—C13—C14—C15	−1.3 (3)
N1—C9—C10—C19	−86.79 (16)	C9—C13—C14—C15	179.6 (2)
C13—C9—C10—C19	37.3 (2)	O1—C7—C6—C5	−16.5 (2)
C8—C9—C10—C19	153.46 (14)	C10—C7—C6—C5	101.8 (2)
N1—C9—C10—C11	35.28 (16)	O1—C7—C6—C1	162.34 (14)
C13—C9—C10—C11	159.32 (14)	C10—C7—C6—C1	−79.3 (2)
C8—C9—C10—C11	−84.48 (15)	C5—C6—C1—C2	−1.3 (3)
N1—C9—C10—C7	155.54 (13)	C7—C6—C1—C2	179.75 (16)
C13—C9—C10—C7	−80.42 (16)	C7—O1—C8—O2	176.05 (16)
C8—C9—C10—C7	35.78 (15)	C7—O1—C8—C9	−5.39 (18)
O1—C7—C10—C19	−161.30 (12)	N1—C9—C8—O2	48.4 (2)
C6—C7—C10—C19	75.41 (18)	C13—C9—C8—O2	−82.4 (2)
O1—C7—C10—C9	−40.25 (15)	C10—C9—C8—O2	157.98 (18)
C6—C7—C10—C9	−163.54 (14)	N1—C9—C8—O1	−129.98 (15)
O1—C7—C10—C11	70.59 (16)	C13—C9—C8—O1	99.13 (16)
C6—C7—C10—C11	−52.7 (2)	C10—C9—C8—O1	−20.45 (17)
N1—C9—C13—C14	−85.5 (2)	C21—N1—C12—C11	166.51 (16)
C10—C9—C13—C14	156.99 (17)	C9—N1—C12—C11	33.62 (19)
C8—C9—C13—C14	46.3 (2)	C10—C11—C12—N1	−10.3 (2)
N1—C9—C13—C18	95.38 (19)	C6—C1—C2—C3	1.9 (3)
C10—C9—C13—C18	−22.2 (2)	C6—C1—C2—C20	−179.25 (18)
C8—C9—C13—C18	−132.79 (17)	C13—C18—C17—C16	0.4 (3)
C18—N2—C19—O3	−176.51 (18)	N2—C18—C17—C16	−179.0 (2)
C18—N2—C19—C10	7.3 (3)	C1—C6—C5—C4	−0.4 (3)
C9—C10—C19—O3	153.12 (16)	C7—C6—C5—C4	178.49 (19)
C11—C10—C19—O3	36.0 (2)	C1—C2—C3—C4	−0.9 (3)
C7—C10—C19—O3	−94.19 (19)	C20—C2—C3—C4	−179.7 (2)
C9—C10—C19—N2	−30.6 (2)	C18—C17—C16—C15	−0.2 (3)
C11—C10—C19—N2	−147.74 (16)	C2—C3—C4—C5	−0.8 (3)
C7—C10—C19—N2	82.07 (18)	C6—C5—C4—C3	1.4 (3)
C14—C13—C18—C17	0.3 (3)	C17—C16—C15—C14	−0.8 (4)
C9—C13—C18—C17	179.47 (17)	C13—C14—C15—C16	1.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3i	0.91 (2)	1.93 (2)	2.802 (2)	159.6 (19)
C5—H5···O2ii	0.93	2.55	3.303 (3)	138

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N2H2AO3i	0.91(2)	1.93(2)	2.802(2)	159.6(19)
C5H5O2ii	0.93	2.55	3.303(3)	138

Symmetry codes: (i) ; (ii) .