Ethyl 2-[1,3-dioxo-6-(piperidin-1-yl)-2,3-dihydro-1H-benz[de]isoquinolin-2-yl]acetate.

In the title compound, C(21)H(22)N(2)O(4), the naphthalimide unit is almost planar (r.m.s. deviation = 0.081Å). The carboximide N atom and the five C atoms of the eth-oxy-carbonyl-methyl substituent also lie close to a common plane (r.m.s. deviation = 0.119Å), which subtends an angle of 71.06 (8)° to the naphthalamide plane. The piperidine ring adopts a chair conformation. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into zigzag chains along the a axis.

Related literature

For general background to applications of 1,8-naphthalimides, see: McAdam et al. (2003 ▶); Fülöp et al. (2009 ▶). For a related structure, see: Hanton et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H22N2O4

M = 366.41

Orthorhombic,

a = 10.959 (2) Å

b = 18.037 (4) Å

c = 9.3330 (19) Å

V = 1844.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius n class="Gene">CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.973, T max = 0.991

3547 measured reflections

1808 independent reflections

1280 reflections with I > 2σ(I)

R int = 0.039

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.115

S = 1.00

1808 reflections

244 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–n class="Chemical">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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811022707/sj5150sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022707/sj5150Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811022707/sj5150Isup3.cml

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

C21H22N2O4	Dx = 1.319 Mg m−3
Mr = 366.41	Melting point: 421 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 25 reflections
a = 10.959 (2) Å	θ = 9–13°
b = 18.037 (4) Å	µ = 0.09 mm−1
c = 9.3330 (19) Å	T = 293 K
V = 1844.8 (6) Å3	Needle, brown
Z = 4	0.30 × 0.20 × 0.10 mm
F(000) = 776

Enraf–Nonius CAD-4 diffractometer	1280 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
graphite	θmax = 25.4°, θmin = 2.2°
ω/2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = −21→21
Tmin = 0.973, Tmax = 0.991	l = 0→11
3547 measured reflections	3 standard reflections every 200 reflections
1808 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.060P)2] where P = (Fo2 + 2Fc2)/3
1808 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.21 e Å−3
2 restraints	Δρmin = −0.13 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
N1	0.4405 (3)	0.21405 (16)	0.7011 (4)	0.0561 (9)
O1	0.2714 (3)	−0.10503 (17)	0.4672 (4)	0.0777 (10)
C1	0.5640 (4)	0.2215 (2)	0.7609 (5)	0.0621 (11)
H1A	0.6237	0.2174	0.6846	0.074*
H1B	0.5788	0.1818	0.8288	0.074*
N2	0.2974 (3)	−0.13210 (17)	0.7041 (4)	0.0553 (8)
O2	0.3201 (3)	−0.15994 (17)	0.9379 (4)	0.0747 (9)
C2	0.5780 (5)	0.2952 (2)	0.8348 (6)	0.0791 (15)
H2A	0.6605	0.3000	0.8713	0.095*
H2B	0.5223	0.2979	0.9154	0.095*
O3	0.3649 (3)	−0.32513 (15)	0.7198 (5)	0.0858 (11)
C3	0.5511 (5)	0.3589 (3)	0.7302 (7)	0.0898 (16)
H3A	0.5523	0.4058	0.7811	0.108*
H3B	0.6133	0.3604	0.6564	0.108*
O4	0.4935 (3)	−0.22931 (16)	0.7031 (4)	0.0705 (8)
C4	0.4263 (4)	0.3472 (2)	0.6620 (6)	0.0717 (13)
H4A	0.3635	0.3527	0.7345	0.086*
H4B	0.4129	0.3848	0.5894	0.086*
C5	0.4158 (4)	0.2712 (2)	0.5944 (5)	0.0670 (12)
H5A	0.3344	0.2645	0.5558	0.080*
H5B	0.4737	0.2669	0.5161	0.080*
C6	0.3992 (3)	0.1420 (2)	0.6730 (4)	0.0509 (10)
C7	0.3691 (4)	0.1189 (2)	0.5352 (5)	0.0601 (11)
H7A	0.3725	0.1524	0.4595	0.072*
C8	0.3337 (4)	0.0458 (3)	0.5101 (5)	0.0618 (12)
H8A	0.3136	0.0311	0.4175	0.074*
C9	0.3280 (3)	−0.0048 (2)	0.6196 (5)	0.0515 (10)
C10	0.3521 (3)	0.0175 (2)	0.7621 (4)	0.0461 (9)
C11	0.3431 (3)	−0.0331 (2)	0.8754 (5)	0.0496 (10)
C12	0.3581 (4)	−0.0101 (2)	1.0172 (5)	0.0586 (11)
H12A	0.3535	−0.0441	1.0918	0.070*
C13	0.3803 (4)	0.0646 (2)	1.0452 (5)	0.0557 (11)
H13A	0.3860	0.0809	1.1395	0.067*
C14	0.3935 (4)	0.1138 (2)	0.9362 (5)	0.0528 (10)
H14A	0.4090	0.1633	0.9577	0.063*
C15	0.3844 (3)	0.0918 (2)	0.7894 (4)	0.0460 (9)
C16	0.2971 (4)	−0.0830 (2)	0.5885 (5)	0.0570 (11)
C17	0.3207 (4)	−0.1124 (2)	0.8465 (5)	0.0538 (11)
C18	0.2784 (3)	−0.21025 (19)	0.6780 (6)	0.0623 (12)
H18A	0.2519	−0.2173	0.5797	0.075*
H18B	0.2143	−0.2283	0.7405	0.075*
C19	0.3916 (4)	−0.2541 (2)	0.7032 (5)	0.0586 (10)
C20	0.4684 (6)	−0.3749 (3)	0.7462 (10)	0.131 (3)
H20A	0.5438	−0.3514	0.7164	0.157*
H20B	0.4742	−0.3861	0.8476	0.157*
C21	0.4499 (6)	−0.4403 (3)	0.6680 (9)	0.145 (3)
H21A	0.5188	−0.4726	0.6805	0.217*
H21B	0.4409	−0.4285	0.5683	0.217*
H21C	0.3775	−0.4647	0.7017	0.217*

	U11	U22	U33	U12	U13	U23
N1	0.059 (2)	0.0473 (17)	0.062 (2)	0.0060 (15)	−0.0043 (19)	0.0084 (18)
O1	0.086 (2)	0.076 (2)	0.071 (2)	0.0046 (17)	−0.0181 (18)	−0.025 (2)
C1	0.055 (3)	0.066 (2)	0.065 (3)	−0.0010 (19)	−0.005 (2)	0.016 (2)
N2	0.0492 (18)	0.0507 (18)	0.066 (2)	−0.0017 (14)	−0.0060 (18)	−0.0060 (19)
O2	0.094 (2)	0.0614 (18)	0.069 (2)	−0.0103 (17)	0.0184 (19)	0.0068 (18)
C2	0.087 (3)	0.068 (3)	0.082 (4)	−0.017 (2)	−0.024 (3)	0.014 (3)
O3	0.076 (2)	0.0521 (16)	0.129 (3)	0.0014 (15)	−0.010 (2)	−0.008 (2)
C3	0.115 (4)	0.060 (3)	0.095 (4)	−0.020 (3)	−0.017 (4)	0.020 (3)
O4	0.0456 (15)	0.0769 (19)	0.089 (2)	0.0008 (14)	0.0091 (17)	−0.0022 (19)
C4	0.089 (3)	0.053 (2)	0.073 (3)	0.005 (2)	0.000 (3)	0.004 (2)
C5	0.077 (3)	0.060 (3)	0.064 (3)	0.009 (2)	−0.007 (2)	0.014 (2)
C6	0.047 (2)	0.057 (2)	0.049 (3)	0.0132 (17)	−0.0027 (18)	0.005 (2)
C7	0.071 (3)	0.066 (3)	0.043 (2)	0.002 (2)	−0.008 (2)	0.001 (2)
C8	0.065 (3)	0.073 (3)	0.047 (3)	0.008 (2)	−0.012 (2)	−0.005 (2)
C9	0.044 (2)	0.056 (3)	0.055 (3)	0.0060 (18)	−0.0017 (18)	0.001 (2)
C10	0.0379 (19)	0.054 (2)	0.047 (2)	0.0054 (16)	−0.0007 (18)	−0.008 (2)
C11	0.048 (2)	0.050 (2)	0.051 (3)	−0.0010 (17)	0.006 (2)	0.002 (2)
C12	0.062 (3)	0.060 (3)	0.054 (3)	0.004 (2)	0.009 (2)	0.006 (2)
C13	0.065 (3)	0.063 (3)	0.039 (2)	0.000 (2)	−0.003 (2)	−0.001 (2)
C14	0.057 (3)	0.049 (2)	0.052 (2)	−0.0009 (19)	−0.005 (2)	−0.002 (2)
C15	0.045 (2)	0.049 (2)	0.044 (2)	0.0067 (16)	0.0014 (19)	−0.0080 (19)
C16	0.041 (2)	0.063 (3)	0.067 (3)	0.0070 (19)	−0.009 (2)	−0.014 (3)
C17	0.040 (2)	0.058 (3)	0.063 (3)	−0.0011 (18)	0.009 (2)	0.001 (2)
C18	0.047 (2)	0.050 (2)	0.090 (4)	−0.0024 (17)	0.002 (2)	−0.011 (2)
C19	0.056 (2)	0.054 (2)	0.066 (3)	0.0008 (19)	0.006 (2)	−0.007 (2)
C20	0.114 (5)	0.077 (3)	0.202 (9)	0.036 (3)	−0.058 (6)	−0.030 (5)
C21	0.138 (6)	0.103 (5)	0.193 (9)	0.036 (4)	−0.019 (6)	−0.014 (6)

N1—C6	1.401 (5)	C6—C15	1.424 (6)
N1—C5	1.459 (5)	C7—C8	1.395 (6)
N1—C1	1.470 (5)	C7—H7A	0.9300
O1—C16	1.233 (5)	C8—C9	1.372 (6)
C1—C2	1.506 (6)	C8—H8A	0.9300
C1—H1A	0.9700	C9—C10	1.414 (6)
C1—H1B	0.9700	C9—C16	1.479 (6)
N2—C16	1.396 (6)	C10—C11	1.400 (5)
N2—C17	1.399 (6)	C10—C15	1.410 (5)
N2—C18	1.446 (4)	C11—C12	1.397 (6)
O2—C17	1.209 (5)	C11—C17	1.475 (5)
C2—C3	1.536 (7)	C12—C13	1.393 (6)
C2—H2A	0.9700	C12—H12A	0.9300
C2—H2B	0.9700	C13—C14	1.359 (6)
O3—C19	1.324 (5)	C13—H13A	0.9300
O3—C20	1.467 (6)	C14—C15	1.430 (6)
C3—C4	1.524 (7)	C14—H14A	0.9300
C3—H3A	0.9700	C18—C19	1.490 (6)
C3—H3B	0.9700	C18—H18A	0.9700
O4—C19	1.202 (5)	C18—H18B	0.9700
C4—C5	1.513 (6)	C20—C21	1.402 (7)
C4—H4A	0.9700	C20—H20A	0.9700
C4—H4B	0.9700	C20—H20B	0.9700
C5—H5A	0.9700	C21—H21A	0.9600
C5—H5B	0.9700	C21—H21B	0.9600
C6—C7	1.391 (6)	C21—H21C	0.9600
C6—N1—C5	117.9 (3)	C8—C9—C16	119.9 (4)
C6—N1—C1	116.9 (3)	C10—C9—C16	119.9 (4)
C5—N1—C1	111.5 (3)	C11—C10—C15	120.1 (3)
N1—C1—C2	110.4 (4)	C11—C10—C9	120.8 (3)
N1—C1—H1A	109.6	C15—C10—C9	119.1 (3)
C2—C1—H1A	109.6	C12—C11—C10	120.8 (4)
N1—C1—H1B	109.6	C12—C11—C17	118.8 (4)
C2—C1—H1B	109.6	C10—C11—C17	120.4 (4)
H1A—C1—H1B	108.1	C13—C12—C11	119.1 (4)
C16—N2—C17	125.0 (3)	C13—C12—H12A	120.4
C16—N2—C18	119.2 (4)	C11—C12—H12A	120.4
C17—N2—C18	115.7 (4)	C14—C13—C12	120.7 (4)
C1—C2—C3	110.4 (4)	C14—C13—H13A	119.7
C1—C2—H2A	109.6	C12—C13—H13A	119.7
C3—C2—H2A	109.6	C13—C14—C15	121.9 (4)
C1—C2—H2B	109.6	C13—C14—H14A	119.1
C3—C2—H2B	109.6	C15—C14—H14A	119.1
H2A—C2—H2B	108.1	C10—C15—C6	119.7 (4)
C19—O3—C20	116.2 (4)	C10—C15—C14	117.1 (4)
C4—C3—C2	109.6 (4)	C6—C15—C14	123.1 (4)
C4—C3—H3A	109.8	O1—C16—N2	120.4 (4)
C2—C3—H3A	109.8	O1—C16—C9	122.7 (4)
C4—C3—H3B	109.8	N2—C16—C9	116.9 (4)
C2—C3—H3B	109.8	O2—C17—N2	119.3 (4)
H3A—C3—H3B	108.2	O2—C17—C11	124.0 (4)
C5—C4—C3	111.6 (4)	N2—C17—C11	116.7 (4)
C5—C4—H4A	109.3	N2—C18—C19	111.7 (3)
C3—C4—H4A	109.3	N2—C18—H18A	109.3
C5—C4—H4B	109.3	C19—C18—H18A	109.3
C3—C4—H4B	109.3	N2—C18—H18B	109.3
H4A—C4—H4B	108.0	C19—C18—H18B	109.3
N1—C5—C4	110.0 (4)	H18A—C18—H18B	107.9
N1—C5—H5A	109.7	O4—C19—O3	124.4 (4)
C4—C5—H5A	109.7	O4—C19—C18	125.2 (4)
N1—C5—H5B	109.7	O3—C19—C18	110.3 (3)
C4—C5—H5B	109.7	C21—C20—O3	108.4 (5)
H5A—C5—H5B	108.2	C21—C20—H20A	110.0
C7—C6—N1	121.9 (4)	O3—C20—H20A	110.0
C7—C6—C15	119.2 (4)	C21—C20—H20B	110.0
N1—C6—C15	118.9 (4)	O3—C20—H20B	110.0
C6—C7—C8	120.3 (4)	H20A—C20—H20B	108.4
C6—C7—H7A	119.8	C20—C21—H21A	109.5
C8—C7—H7A	119.8	C20—C21—H21B	109.5
C9—C8—C7	121.1 (4)	H21A—C21—H21B	109.5
C9—C8—H8A	119.5	C20—C21—H21C	109.5
C7—C8—H8A	119.5	H21A—C21—H21C	109.5
C8—C9—C10	120.2 (4)	H21B—C21—H21C	109.5
C6—N1—C1—C2	−159.0 (4)	C11—C10—C15—C14	−6.7 (5)
C5—N1—C1—C2	61.3 (5)	C9—C10—C15—C14	172.7 (4)
N1—C1—C2—C3	−57.5 (5)	C7—C6—C15—C10	6.8 (5)
C1—C2—C3—C4	53.7 (6)	N1—C6—C15—C10	−175.1 (3)
C2—C3—C4—C5	−53.6 (6)	C7—C6—C15—C14	−169.4 (4)
C6—N1—C5—C4	160.5 (4)	N1—C6—C15—C14	8.8 (5)
C1—N1—C5—C4	−60.2 (5)	C13—C14—C15—C10	4.5 (5)
C3—C4—C5—N1	56.7 (5)	C13—C14—C15—C6	−179.3 (4)
C5—N1—C6—C7	18.9 (6)	C17—N2—C16—O1	−177.5 (4)
C1—N1—C6—C7	−118.2 (4)	C18—N2—C16—O1	5.7 (6)
C5—N1—C6—C15	−159.2 (4)	C17—N2—C16—C9	2.2 (6)
C1—N1—C6—C15	63.7 (5)	C18—N2—C16—C9	−174.6 (3)
N1—C6—C7—C8	177.0 (4)	C8—C9—C16—O1	−2.6 (6)
C15—C6—C7—C8	−4.9 (6)	C10—C9—C16—O1	177.6 (4)
C6—C7—C8—C9	−0.1 (6)	C8—C9—C16—N2	177.7 (4)
C7—C8—C9—C10	3.3 (6)	C10—C9—C16—N2	−2.1 (5)
C7—C8—C9—C16	−176.5 (4)	C16—N2—C17—O2	−179.0 (4)
C8—C9—C10—C11	178.1 (4)	C18—N2—C17—O2	−2.1 (5)
C16—C9—C10—C11	−2.1 (5)	C16—N2—C17—C11	1.8 (5)
C8—C9—C10—C15	−1.3 (6)	C18—N2—C17—C11	178.7 (3)
C16—C9—C10—C15	178.4 (3)	C12—C11—C17—O2	−3.6 (6)
C15—C10—C11—C12	4.1 (5)	C10—C11—C17—O2	174.7 (4)
C9—C10—C11—C12	−175.3 (4)	C12—C11—C17—N2	175.5 (4)
C15—C10—C11—C17	−174.2 (3)	C10—C11—C17—N2	−6.1 (5)
C9—C10—C11—C17	6.3 (5)	C16—N2—C18—C19	110.2 (4)
C10—C11—C12—C13	1.2 (6)	C17—N2—C18—C19	−66.9 (5)
C17—C11—C12—C13	179.5 (4)	C20—O3—C19—O4	2.9 (8)
C11—C12—C13—C14	−3.5 (6)	C20—O3—C19—C18	−179.7 (5)
C12—C13—C14—C15	0.6 (6)	N2—C18—C19—O4	−20.9 (7)
C11—C10—C15—C6	176.9 (3)	N2—C18—C19—O3	161.8 (4)
C9—C10—C15—C6	−3.7 (5)	C19—O3—C20—C21	−139.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2i	0.97	2.60	3.455 (6)	147
C1—H1B···O1ii	0.97	2.51	3.373 (5)	149
C5—H5A···O2iii	0.97	2.44	3.219 (6)	138
C18—H18A···O1	0.97	2.29	2.735 (6)	107
C18—H18B···O4iv	0.97	2.56	3.315 (5)	135
C20—H20A···O4	0.97	2.27	2.671 (6)	103

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2i	0.97	2.60	3.455 (6)	147
C1—H1B⋯O1ii	0.97	2.51	3.373 (5)	149
C5—H5A⋯O2iii	0.97	2.44	3.219 (6)	138
C18—H18B⋯O4iv	0.97	2.56	3.315 (5)	135

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