7-Pivaloyl-5,6-dihydro-4H-naphtho[3,2,1-de]isoquinoline-4,6-dione.

In the crystal structure of the title compound, C(21)H(17)NO(3), the dibenzo-isoquinoline-dione unit has a planar structure, the maximum atomic deviation being 0.091 (3) Å. The crystal structure is stabilized by π-π stacking [centroid-centroid distance = 3.851 (2) Å] and inter-molecular N-H⋯O hydrogen bonding.

Related literature

The title compound is an azonafide analogue. For the bio­logical activity of 1,3,4(2H)-isoquinoline­trione derivatives, see: Malamas et al. (1994 ▶); Hall et al. (1994 ▶). For the anti­tumor properties of azonafide and analogues, see: Sami et al. (2000 ▶); Hutchings et al. (1988 ▶). For the synthesis, see: Zhang et al. (2000 ▶).

Experimental

Crystal data

C21H17NO3

M = 331.36

Monoclinic,

a = 11.569 (2) Å

b = 9.1150 (18) Å

c = 15.746 (3) Å

β = 101.12 (3)°

V = 1629.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.10 × 0.10 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (CAD-4 EXPRESS; Enraf–Nonius, 1994 ▶) T min = 0.991, T max = 0.996

3103 measured reflections

2950 independent reflections

1264 reflections with I > 2σ(I)

R int = 0.056

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.077

S = 1.00

2950 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810008378/xu2713sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008378/xu2713Isup2.hkl

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

C21H17NO3	F(000) = 696
Mr = 331.36	Dx = 1.351 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.569 (2) Å	θ = 9–12°
b = 9.1150 (18) Å	µ = 0.09 mm−1
c = 15.746 (3) Å	T = 298 K
β = 101.12 (3)°	Block, light-yellow
V = 1629.3 (6) Å3	0.10 × 0.10 × 0.05 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1264 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
graphite	θmax = 25.3°, θmin = 1.8°
ω/2θ scans	h = 0→13
Absorption correction: ψ scan (CAD-4 EXPRESS; Enraf–Nonius, 1994)	k = 0→10
Tmin = 0.991, Tmax = 0.996	l = −18→18
3103 measured reflections	3 standard reflections every 200 reflections
2950 independent reflections	intensity decay: 1%

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.001P)2] where P = (Fo2 + 2Fc2)/3
2950 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.18 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
N	0.9224 (2)	0.3212 (3)	0.52319 (16)	0.0380 (8)
H0A	0.9433	0.4046	0.5467	0.046*
O1	0.7998 (2)	−0.0308 (3)	0.72692 (14)	0.0517 (7)
O2	0.9979 (2)	0.3921 (2)	0.40785 (14)	0.0494 (7)
O3	0.8470 (2)	0.2652 (2)	0.64021 (14)	0.0508 (7)
C1	0.5388 (3)	−0.0139 (4)	0.6829 (2)	0.0769 (14)
H1A	0.5228	−0.0812	0.6352	0.115*
H1B	0.4670	0.0333	0.6897	0.115*
H1C	0.5713	−0.0664	0.7349	0.115*
C2	0.5766 (3)	0.1815 (4)	0.5817 (2)	0.0675 (13)
H2A	0.5630	0.1123	0.5349	0.101*
H2B	0.6310	0.2552	0.5704	0.101*
H2C	0.5035	0.2271	0.5870	0.101*
C3	0.6483 (3)	0.2081 (4)	0.7420 (2)	0.0781 (15)
H3A	0.7027	0.2832	0.7326	0.117*
H3B	0.6803	0.1551	0.7939	0.117*
H3C	0.5750	0.2524	0.7478	0.117*
C4	0.6277 (3)	0.1027 (4)	0.6652 (2)	0.0461 (10)
C5	0.7422 (3)	0.0215 (4)	0.6623 (2)	0.0358 (9)
C6	0.7748 (3)	−0.0144 (4)	0.5757 (2)	0.0337 (9)
C7	0.7494 (3)	−0.1610 (4)	0.5410 (2)	0.0358 (9)
C8	0.7003 (3)	−0.2677 (4)	0.5887 (2)	0.0504 (11)
H8A	0.6861	−0.2445	0.6433	0.061*
C9	0.6734 (3)	−0.4046 (4)	0.5553 (3)	0.0584 (12)
H9A	0.6409	−0.4736	0.5874	0.070*
C10	0.6942 (3)	−0.4420 (4)	0.4742 (2)	0.0560 (12)
H10A	0.6738	−0.5346	0.4514	0.067*
C11	0.7448 (3)	−0.3419 (4)	0.4277 (2)	0.0457 (11)
H11A	0.7606	−0.3690	0.3742	0.055*
C12	0.7736 (3)	−0.1988 (4)	0.4589 (2)	0.0351 (9)
C13	0.8287 (3)	−0.0921 (4)	0.4115 (2)	0.0361 (9)
C14	0.8587 (3)	0.0469 (4)	0.4492 (2)	0.0314 (9)
C15	0.8305 (3)	0.0825 (4)	0.5310 (2)	0.0320 (9)
C16	0.8571 (3)	−0.1202 (4)	0.3306 (2)	0.0430 (10)
H16A	0.8379	−0.2110	0.3048	0.052*
C17	0.9120 (3)	−0.0188 (4)	0.2882 (2)	0.0480 (11)
H17A	0.9299	−0.0415	0.2346	0.058*
C18	0.9412 (3)	0.1181 (4)	0.3250 (2)	0.0417 (10)
H18A	0.9782	0.1872	0.2959	0.050*
C19	0.9154 (3)	0.1513 (4)	0.4046 (2)	0.0324 (9)
C20	0.9491 (3)	0.2966 (4)	0.4427 (2)	0.0358 (9)
C21	0.8659 (3)	0.2269 (4)	0.5700 (2)	0.0364 (9)

	U11	U22	U33	U12	U13	U23
N	0.052 (2)	0.0271 (19)	0.0377 (18)	−0.0090 (16)	0.0150 (16)	−0.0042 (15)
O1	0.0629 (19)	0.0489 (18)	0.0445 (16)	0.0042 (15)	0.0135 (14)	0.0078 (14)
O2	0.070 (2)	0.0339 (16)	0.0499 (16)	−0.0110 (14)	0.0247 (14)	0.0060 (13)
O3	0.073 (2)	0.0420 (17)	0.0425 (15)	−0.0127 (15)	0.0247 (15)	−0.0123 (13)
C1	0.061 (3)	0.071 (3)	0.109 (4)	−0.017 (3)	0.044 (3)	0.007 (3)
C2	0.058 (3)	0.052 (3)	0.090 (3)	0.008 (2)	0.009 (3)	0.009 (3)
C3	0.079 (3)	0.070 (3)	0.094 (3)	0.002 (3)	0.040 (3)	−0.031 (3)
C4	0.046 (3)	0.041 (3)	0.054 (3)	−0.001 (2)	0.017 (2)	−0.004 (2)
C5	0.050 (3)	0.024 (2)	0.035 (2)	−0.004 (2)	0.011 (2)	0.0057 (18)
C6	0.044 (2)	0.027 (2)	0.030 (2)	0.0027 (19)	0.0083 (18)	−0.0013 (18)
C7	0.044 (3)	0.022 (2)	0.042 (2)	0.0019 (19)	0.010 (2)	0.0068 (19)
C8	0.067 (3)	0.032 (2)	0.056 (3)	0.002 (2)	0.020 (2)	0.005 (2)
C9	0.074 (3)	0.040 (3)	0.067 (3)	−0.005 (3)	0.027 (3)	0.007 (2)
C10	0.069 (3)	0.026 (2)	0.073 (3)	−0.008 (2)	0.014 (3)	0.000 (2)
C11	0.057 (3)	0.027 (2)	0.052 (3)	0.000 (2)	0.005 (2)	−0.007 (2)
C12	0.037 (2)	0.028 (2)	0.040 (2)	0.0029 (19)	0.0064 (19)	−0.0003 (19)
C13	0.039 (2)	0.035 (2)	0.034 (2)	0.002 (2)	0.0067 (19)	−0.0011 (19)
C14	0.032 (2)	0.029 (2)	0.034 (2)	0.0041 (18)	0.0072 (18)	0.0045 (18)
C15	0.036 (2)	0.026 (2)	0.036 (2)	0.0004 (18)	0.0107 (18)	−0.0004 (18)
C16	0.055 (3)	0.034 (2)	0.041 (2)	0.006 (2)	0.014 (2)	−0.004 (2)
C17	0.069 (3)	0.046 (3)	0.033 (2)	0.001 (2)	0.020 (2)	0.000 (2)
C18	0.052 (3)	0.036 (2)	0.039 (2)	−0.003 (2)	0.013 (2)	−0.001 (2)
C19	0.037 (2)	0.027 (2)	0.034 (2)	0.0038 (19)	0.0084 (18)	−0.0022 (18)
C20	0.046 (3)	0.029 (2)	0.033 (2)	0.004 (2)	0.0090 (19)	0.0032 (18)
C21	0.038 (2)	0.037 (2)	0.037 (2)	0.001 (2)	0.0119 (19)	−0.002 (2)

N—C21	1.376 (4)	C7—C12	1.417 (4)
N—C20	1.379 (3)	C8—C9	1.366 (4)
N—H0A	0.8600	C8—H8A	0.9300
O1—C5	1.201 (3)	C9—C10	1.387 (4)
O2—C20	1.224 (3)	C9—H9A	0.9300
O3—C21	1.219 (3)	C10—C11	1.369 (4)
C1—C4	1.541 (4)	C10—H10A	0.9300
C1—H1A	0.9600	C11—C12	1.410 (4)
C1—H1B	0.9600	C11—H11A	0.9300
C1—H1C	0.9600	C12—C13	1.447 (4)
C2—C4	1.514 (4)	C13—C16	1.399 (4)
C2—H2A	0.9600	C13—C14	1.413 (4)
C2—H2B	0.9600	C14—C19	1.416 (4)
C2—H2C	0.9600	C14—C15	1.426 (4)
C3—C4	1.527 (4)	C15—C21	1.476 (4)
C3—H3A	0.9600	C16—C17	1.366 (4)
C3—H3B	0.9600	C16—H16A	0.9300
C3—H3C	0.9600	C17—C18	1.390 (4)
C4—C5	1.526 (4)	C17—H17A	0.9300
C5—C6	1.520 (4)	C18—C19	1.378 (4)
C6—C15	1.365 (4)	C18—H18A	0.9300
C6—C7	1.452 (4)	C19—C20	1.475 (4)
C7—C8	1.413 (4)
C21—N—C20	127.1 (3)	C8—C9—C10	120.8 (4)
C21—N—H0A	116.4	C8—C9—H9A	119.6
C20—N—H0A	116.4	C10—C9—H9A	119.6
C4—C1—H1A	109.5	C11—C10—C9	119.7 (4)
C4—C1—H1B	109.5	C11—C10—H10A	120.1
H1A—C1—H1B	109.5	C9—C10—H10A	120.1
C4—C1—H1C	109.5	C10—C11—C12	121.8 (4)
H1A—C1—H1C	109.5	C10—C11—H11A	119.1
H1B—C1—H1C	109.5	C12—C11—H11A	119.1
C4—C2—H2A	109.5	C11—C12—C7	117.8 (3)
C4—C2—H2B	109.5	C11—C12—C13	122.7 (3)
H2A—C2—H2B	109.5	C7—C12—C13	119.4 (3)
C4—C2—H2C	109.5	C16—C13—C14	117.7 (3)
H2A—C2—H2C	109.5	C16—C13—C12	123.4 (3)
H2B—C2—H2C	109.5	C14—C13—C12	118.9 (3)
C4—C3—H3A	109.5	C13—C14—C19	119.6 (3)
C4—C3—H3B	109.5	C13—C14—C15	120.2 (3)
H3A—C3—H3B	109.5	C19—C14—C15	120.2 (3)
C4—C3—H3C	109.5	C6—C15—C14	122.1 (3)
H3A—C3—H3C	109.5	C6—C15—C21	118.9 (3)
H3B—C3—H3C	109.5	C14—C15—C21	119.0 (3)
C2—C4—C5	113.6 (3)	C17—C16—C13	122.3 (3)
C2—C4—C3	111.3 (3)	C17—C16—H16A	118.8
C5—C4—C3	108.9 (3)	C13—C16—H16A	118.8
C2—C4—C1	108.8 (3)	C16—C17—C18	120.1 (3)
C5—C4—C1	106.5 (3)	C16—C17—H17A	120.0
C3—C4—C1	107.4 (3)	C18—C17—H17A	120.0
O1—C5—C6	118.8 (3)	C19—C18—C17	119.9 (3)
O1—C5—C4	120.7 (3)	C19—C18—H18A	120.0
C6—C5—C4	119.9 (3)	C17—C18—H18A	120.0
C15—C6—C7	118.9 (3)	C18—C19—C14	120.4 (3)
C15—C6—C5	123.1 (3)	C18—C19—C20	118.7 (3)
C7—C6—C5	117.9 (3)	C14—C19—C20	120.9 (3)
C8—C7—C12	119.2 (3)	O2—C20—N	120.0 (3)
C8—C7—C6	120.4 (3)	O2—C20—C19	124.4 (3)
C12—C7—C6	120.4 (3)	N—C20—C19	115.5 (3)
C9—C8—C7	120.6 (4)	O3—C21—N	119.6 (3)
C9—C8—H8A	119.7	O3—C21—C15	123.3 (3)
C7—C8—H8A	119.7	N—C21—C15	117.2 (3)
C2—C4—C5—O1	170.9 (3)	C12—C13—C14—C15	−2.5 (5)
C3—C4—C5—O1	46.3 (4)	C7—C6—C15—C14	3.4 (5)
C1—C4—C5—O1	−69.3 (4)	C5—C6—C15—C14	−179.1 (3)
C2—C4—C5—C6	−18.5 (5)	C7—C6—C15—C21	−174.6 (3)
C3—C4—C5—C6	−143.2 (3)	C5—C6—C15—C21	2.9 (5)
C1—C4—C5—C6	101.2 (4)	C13—C14—C15—C6	0.2 (5)
O1—C5—C6—C15	−105.0 (4)	C19—C14—C15—C6	179.3 (3)
C4—C5—C6—C15	84.3 (4)	C13—C14—C15—C21	178.3 (3)
O1—C5—C6—C7	72.5 (4)	C19—C14—C15—C21	−2.7 (5)
C4—C5—C6—C7	−98.2 (4)	C14—C13—C16—C17	0.1 (5)
C15—C6—C7—C8	175.1 (3)	C12—C13—C16—C17	−178.2 (3)
C5—C6—C7—C8	−2.5 (5)	C13—C16—C17—C18	−0.3 (6)
C15—C6—C7—C12	−4.9 (5)	C16—C17—C18—C19	0.4 (5)
C5—C6—C7—C12	177.5 (3)	C17—C18—C19—C14	−0.3 (5)
C12—C7—C8—C9	−1.7 (6)	C17—C18—C19—C20	179.0 (3)
C6—C7—C8—C9	178.3 (4)	C13—C14—C19—C18	0.1 (5)
C7—C8—C9—C10	0.2 (6)	C15—C14—C19—C18	−179.0 (3)
C8—C9—C10—C11	1.6 (6)	C13—C14—C19—C20	−179.2 (3)
C9—C10—C11—C12	−2.0 (6)	C15—C14—C19—C20	1.7 (5)
C10—C11—C12—C7	0.5 (5)	C21—N—C20—O2	178.6 (3)
C10—C11—C12—C13	179.0 (4)	C21—N—C20—C19	−1.6 (5)
C8—C7—C12—C11	1.3 (5)	C18—C19—C20—O2	0.9 (6)
C6—C7—C12—C11	−178.7 (3)	C14—C19—C20—O2	−179.8 (3)
C8—C7—C12—C13	−177.3 (3)	C18—C19—C20—N	−178.9 (3)
C6—C7—C12—C13	2.7 (5)	C14—C19—C20—N	0.4 (5)
C11—C12—C13—C16	0.7 (5)	C20—N—C21—O3	−179.0 (3)
C7—C12—C13—C16	179.3 (3)	C20—N—C21—C15	0.6 (5)
C11—C12—C13—C14	−177.6 (3)	C6—C15—C21—O3	−0.7 (5)
C7—C12—C13—C14	1.0 (5)	C14—C15—C21—O3	−178.8 (3)
C16—C13—C14—C19	0.0 (5)	C6—C15—C21—N	179.6 (3)
C12—C13—C14—C19	178.4 (3)	C14—C15—C21—N	1.6 (5)
C16—C13—C14—C15	179.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O2i	0.86	2.05	2.911 (3)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯O2i	0.86	2.05	2.911 (3)	174

Symmetry code: (i) .