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

Xia, S.; Zheng, C.-L.; He, F.-F.; Shi, Y.-B.; Wang, H.-B.

doi:10.1107/S1600536811022707

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1717

doi:10.1107/S1600536811022707

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

Song Xia,^a,^b Chun-Ling Zheng,^a Fei-Fei He,^a,^b Ya-Bin Shi ^a,^b and Hai-Bo Wang ^a ^*

^aCollege of Food Science and Light Industry, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and ^bCollege of Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: wanghaibo@njut.edu.cn

(Received 20 May 2011; accepted 12 June 2011; online 18 June 2011)

In the title compound, C₂₁H₂₂N₂O₄, the naphthalimide unit is almost planar (r.m.s. deviation = 0.081Å). The carboximide N atom and the five C atoms of the ethoxycarbonylmethyl 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, intermolecular C—H⋯O hydrogen bonds link the molecules 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_r = 366.41
Orthorhombic, P n a 2₁
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 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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.115
S = 1.00
1808 reflections
244 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.13 e Å⁻³

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⋯O4^iv	0.97	2.56	3.315 (5)	135
Symmetry codes: (i) $[-x+1, -y, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, -y, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z]$ .

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811022707/sj5150sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811022707/sj5150Isup3.cml

checkCIF report

Comment top

1,8-naphthalimide derivatives are recognized to have an importance in dye and medicinal chemistry. They can be used as intermediates in the synthesis of organic pigments, in biological fluorescent labeling and as optical brighteners, pH-dependent sensors, laser and electroluminscent dyes and liquid crystals (McAdam et al., 2003). We have selected 4-substituted 1,8-naphthalimides to use in the synthesis of fluorophore groups, since they are highly photostable, cheap and their chemical modification is straightforward. Moreover, these dyes exhibit large Stoke's shifts due to the formation of an intramolecular charge transfer (ICT) state upon absorption of light. (Fülöp et al. 2009).

We report here the crystal structure of the title compound, N-[(2-Ethoxy)-2-oxo-ethyl]-4-piperidino-1,8-naphthalimide. In the structure of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges (Hanton et al., 2010). In the crystal structure, intermolecular C-H···O hydrogen bonds link the molecules into zig-zag chains along the a axis, to form a stable structure (Fig. 2).

Related literature top

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 top

The title compound, 1H-Benz[de]isoquinoline- 2(3H)-acetic acid, 6-(piperidin-1-yl)-1,3-dioxo-, ethyl ester was prepared by a method similar to that reported in the literature (Fülöp et al. 2009). 1H-Benz [de]isoquinoline- 2(3H)-acetic acid, 6-bromo-1,3-dioxo-, ethyl ester(3.82 g, 10.5 mmol) was dissolved in N-methylpyrrolidone (NMP, 58.5 mL) and piperidine (4.5 mL, 52.5 mmol) together with triethylamine (TEA, 14.8 mL, 105 mmol) were added. The mixture was stirred for 4 h at 383K. Then water (200 mL) was added, which induced formation of yellow precipitate. The precipitate was filtered, washed with water (150 mL), dried and re-crystallized from ethanol. Yield 3.34 g (86%). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of the title compound viewed down the c axis. Dashed lines indicate intermolecular C-H···O interactions.

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

Crystal data top

C₂₁H₂₂N₂O₄	D_x = 1.319 Mg m⁻³
M_r = 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

Data collection top

Enraf–Nonius CAD-4 diffractometer	1280 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.039
Graphite monochromator	θ_max = 25.4°, θ_min = 2.2°
ω/2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = −21→21
T_min = 0.973, T_max = 0.991	l = 0→11
3547 measured reflections	3 standard reflections every 200 reflections
1808 independent reflections	intensity decay: 1%

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) = 0.115	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.060P)²] where P = (F_o² + 2F_c²)/3
1808 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.21 e Å⁻³
2 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₂₁H₂₂N₂O₄	V = 1844.8 (6) Å³
M_r = 366.41	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 10.959 (2) Å	µ = 0.09 mm⁻¹
b = 18.037 (4) Å	T = 293 K
c = 9.3330 (19) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1280 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.039
T_min = 0.973, T_max = 0.991	3 standard reflections every 200 reflections
3547 measured reflections	intensity decay: 1%
1808 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	2 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
1808 reflections	Δρ_min = −0.13 e Å⁻³
244 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O4^iv	0.97	2.56	3.315 (5)	135
C20—H20A···O4	0.97	2.27	2.671 (6)	103

Symmetry codes: (i) −x+1, −y, z−1/2; (ii) −x+1, −y, z+1/2; (iii) −x+1/2, y+1/2, z−1/2; (iv) x−1/2, −y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₂N₂O₄
M_r	366.41
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	10.959 (2), 18.037 (4), 9.3330 (19)
V (Å³)	1844.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.973, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	3547, 1808, 1280
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.115, 1.00
No. of reflections	1808
No. of parameters	244
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.13

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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···O4^iv	0.97	2.56	3.315 (5)	135

Symmetry codes: (i) −x+1, −y, z−1/2; (ii) −x+1, −y, z+1/2; (iii) −x+1/2, y+1/2, z−1/2; (iv) x−1/2, −y−1/2, z.

Acknowledgements

This work was supported by the Higher Education Institutions Natural Science Foundation of the Jiangsu Educational Commission (grant No. 09KJB540001) and the General Program of the National Natural Science Foundation of China (grant No. 51003047).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft. The Netherlands. Google Scholar
Fülöp, A., Arian, D., Lysenko, A. & Mokhir, A. (2009). Bioorg. Med. Chem. Lett. 19, 3104–3107. Web of Science PubMed Google Scholar
Hanton, L. R., Moratti, S. C., Shi, Z. & Simpson, J. (2010). Acta Cryst. E66, o1476–o1477. Web of Science CSD CrossRef IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
McAdam, C. J., Morgan, J. L., Robinson, B. H., Simpson, J., Rieger, P. H. & Rieger, A. L. (2003). Organometallics, 22, 5126–5136. Web of Science CSD CrossRef CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

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