Crystal structure of 14-methyl-11-(3-methyl­phen­yl)-12-oxa-8,14-di­aza­tetra­cyclo­[8.3.3.01,10.02,7]hexa­deca-2(7),3,5-triene-9,13-dione

Savithri, M.P.; Suresh, M.; Raghunathan, R.; Raja, R.; SubbiahPandi, A.

doi:10.1107/S2056989015008129

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 71| Part 6| June 2015| Pages o379-o380

doi:10.1107/S2056989015008129

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Crystal structure of 14-methyl-11-(3-methylphenyl)-12-oxa-8,14-diazatetracyclo[8.3.3.0^1,10.0^2,7]hexadeca-2(7),3,5-triene-9,13-dione

M. P. Savithri,^a M. Suresh,^b R. Raghunathan,^b R. Raja ^c and A. SubbiahPandi ^c ^*

^aDepartment of Physics, Queen Mary's College (Autonomous), Chennai 600 004, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
^*Correspondence e-mail: aspandian59@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 28 January 2015; accepted 23 April 2015; online 7 May 2015)

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 C_q—N (q = quaternary) bond. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R₂²(8) loops. The dimers are linked into [110] chains by pairs of C—H⋯O interactions, which generate R₂²(14) loops.

Keywords: crystal structure; tetracyclo; hexadecatrienedione; hydrogen bonding.

CCDC reference: 1061495

1. 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 ).

2. Experimental

2.1. Crystal data

C₂₁H₂₀N₂O₃
M_r = 348.39
Monoclinic, P 2₁ /c
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.137
S = 1.09
3787 reflections
239 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y, -z+1.

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 ).

Supporting information

CCDC reference: 1061495

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015008129/hb7360sup1.cif

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

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

checkCIF report

Comment top

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structures (Ramesh et al., 2008; Zhao & Teng, 2008; Bai et al., 2009; Du et al., 2010; Wang et al., 2010). The five-membered furan ring (atoms O1/C7–C10) adopts an envelope conformation, with atom C10 as the flap, with puckering parameters (Cremer & Pople, 1975), q₂ = 0.4062 (2) Å and ϕ₂ = 246.5 (2)° and the pyrrolidine ring (atoms N1/C9–C12) exhibits a twisted conformation as indicated by the puckering parameters q₂ = 0.3981 (2) Å and ϕ₂ = 22.4 (3)°. The quinoline ring system is roughly planar, with a maximum deviation of 0.315 (2) Å for atom C10 and the plane of the furan ring is oriented at dihedral angles of 72.5 (8) and 77.9 (1)° with respect to the quinoline and pyrrolidine rings, respectively.

In the crystal, hydrogen-bonded chains running along [110] are generated by connecting neighbouring molecules via C—H···O and N—H···O hydrogen bonds, forming a chain. Intermolecular C5—H5···O2 hydrohen bonding forms an R₂²(14) graph-set dimer (Fig. 2 and Table 1). In addition to this, another graph-set dimer of R₂²(8) forms in the unit cell involving N2—H2A···O3 hydrogen bonds (Fig. 2).

Related literature top

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 top

A mixture of methyl 2-(hydroxy(m-tolyl)methyl)acrylate (1 mmol), isatin (1.1 mmol) and sarcosine (1.1 mmol) was placed in a round bottom flask and melted at 180°C until completion of the reaction was evidenced by TLC analysis. After completion of the reaction, the crude product was washed with 5ml of ethylacetate and hexane mixture (1:4 ratio) which successfully provided the pure product as colorless solid. The product was dissolved in ethyl acetate and heated for two minutes. The resulting solution was subjected to crystallization by slow evaporation of the solvent for 48 hours resulting in the formation of colourless blocks.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. 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.

14-Methyl-11-(3-methylphenyl)-12-oxa-8,14-diazatetracyclo[8.3.3.0^1,10.0^2,7]hexadeca-2(7),3,5-triene-9,13-dione top

Crystal data top

C₂₁H₂₀N₂O₃	F(000) = 736
M_r = 348.39	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0557P)² + 0.7606P] where P = (F_o² + 2F_c²)/3
3787 reflections	(Δ/σ)_max < 0.001
239 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₁H₂₀N₂O₃	V = 1737.2 (2) Å³
M_r = 348.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.4772 (7) Å	µ = 0.09 mm⁻¹
b = 8.6834 (6) Å	T = 293 K
c = 19.1123 (13) Å	0.35 × 0.30 × 0.30 mm
β = 92.490 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3787 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2875 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.974	R_int = 0.024
25650 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.29 e Å⁻³
3787 reflections	Δρ_min = −0.21 e Å⁻³
239 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

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

Hydrogen-bond geometry (Å, º) top

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)	137.8

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

Acknowledgements

MPS and ASP thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for the data collection.

References

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Volume 71| Part 6| June 2015| Pages o379-o380

doi:10.1107/S2056989015008129

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 14-methyl-11-(3-methyl­phen­yl)-12-oxa-8,14-di­aza­tetra­cyclo­[8.3.3.01,10.02,7]hexa­deca-2(7),3,5-triene-9,13-dione

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 14-methyl-11-(3-methylphenyl)-12-oxa-8,14-diazatetracyclo[8.3.3.0^1,10.0^2,7]hexadeca-2(7),3,5-triene-9,13-dione