Ethyl 4-(1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)benzoate.

The title compound, C(21)H(15)NO(4), was synthesized by reducing the Schiff base obtained from acenaphthenequinone and ethyl-4-aminobenzoate. The dihedral angle between the essentially planar 1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline ring system [maximum deviation = 0.061 (2) Å] and the benzene ring is 75.08 (10)°. In the crystal, mol-ecules are connected via weak inter-molecular C-H⋯O hydrogen bonds, forming a two-dimensional network. The ethyl group is disordered over two sets of sites with a refined occupancy ratio of 0.502 (12):0.498 (12).

Related literature

For details and applications of acenaphthenquinone-based Schiff bases, see: Maldanis et al. (2002 ▶); Son et al. (2006 ▶); Mhaidat et al. (2009 ▶); Rodriguez-Argüelles et al. (1997 ▶); McDavid et al. (1951 ▶); Salhin et al. (2007 ▶, 2008 ▶, 2009 ▶); Tameem et al. (2006 ▶, 2007 ▶, 2008 ▶); Shalash et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H15NO4

M = 345.34

Monoclinic,

a = 5.2025 (7) Å

b = 18.066 (3) Å

c = 17.560 (2) Å

β = 98.365 (2)°

V = 1632.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.49 × 0.21 × 0.08 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.953, T max = 0.992

15726 measured reflections

2393 independent reflections

2157 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.171

S = 1.07

2393 reflections

256 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681005049X/lh5180sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005049X/lh5180Isup2.hkl

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

C21H15NO4	F(000) = 720
Mr = 345.34	Dx = 1.405 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5950 reflections
a = 5.2025 (7) Å	θ = 2.5–30.0°
b = 18.066 (3) Å	µ = 0.10 mm−1
c = 17.560 (2) Å	T = 100 K
β = 98.365 (2)°	Needle, colourless
V = 1632.8 (4) Å3	0.49 × 0.21 × 0.08 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	2393 independent reflections
Radiation source: fine-focus sealed tube	2157 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 30.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
Tmin = 0.953, Tmax = 0.992	k = −25→25
15726 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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0659P)2 + 3.4903P] where P = (Fo2 + 2Fc2)/3
2393 reflections	(Δ/σ)max < 0.001
256 parameters	Δρmax = 0.56 e Å−3
4 restraints	Δρmin = −0.38 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
O1	0.6572 (6)	0.08698 (16)	0.20848 (18)	0.0348 (6)
O2	1.3670 (6)	−0.02019 (16)	0.3453 (2)	0.0378 (7)
O3	0.9558 (11)	0.3058 (3)	0.5083 (2)	0.0746 (15)
O4	1.2949 (12)	0.3339 (3)	0.4533 (4)	0.105 (2)
C1	0.7860 (7)	0.0310 (2)	0.2216 (2)	0.0259 (7)
C2	0.7297 (7)	−0.0388 (2)	0.1797 (2)	0.0271 (7)
C3	0.5174 (8)	−0.0424 (2)	0.1229 (2)	0.0336 (8)
H3A	0.4150	−0.0007	0.1106	0.040*
C4	0.4555 (9)	−0.1099 (3)	0.0835 (3)	0.0386 (9)
H4A	0.3117	−0.1125	0.0453	0.046*
C5	0.6070 (8)	−0.1716 (2)	0.1013 (2)	0.0334 (8)
H5A	0.5639	−0.2158	0.0753	0.040*
C6	0.8256 (7)	−0.1689 (2)	0.1583 (2)	0.0293 (8)
C7	0.9882 (8)	−0.2308 (2)	0.1776 (2)	0.0332 (8)
H7A	0.9477	−0.2756	0.1527	0.040*
C8	1.2041 (9)	−0.2262 (2)	0.2323 (3)	0.0338 (8)
H8A	1.3093	−0.2674	0.2440	0.041*
C9	1.2662 (8)	−0.1586 (2)	0.2707 (2)	0.0293 (7)
H9A	1.4141	−0.1554	0.3073	0.035*
C10	1.1111 (7)	−0.09719 (19)	0.2547 (2)	0.0254 (7)
C11	0.8898 (7)	−0.1011 (2)	0.1980 (2)	0.0245 (7)
C12	1.1773 (7)	−0.0277 (2)	0.2972 (2)	0.0267 (7)
N1	1.0028 (6)	0.03130 (17)	0.27965 (19)	0.0254 (6)
C13	1.0402 (7)	0.0969 (2)	0.3273 (2)	0.0262 (7)
C14	1.2342 (7)	0.1468 (2)	0.3184 (2)	0.0290 (7)
H14A	1.3454	0.1382	0.2824	0.035*
C15	1.2614 (8)	0.2100 (2)	0.3639 (3)	0.0345 (9)
H15A	1.3917	0.2440	0.3587	0.041*
C16	1.0928 (9)	0.2223 (2)	0.4175 (2)	0.0358 (9)
C17	0.9001 (8)	0.1711 (3)	0.4258 (2)	0.0363 (9)
H17A	0.7891	0.1793	0.4619	0.044*
C18	0.8716 (8)	0.1078 (2)	0.3807 (2)	0.0322 (8)
H18A	0.7424	0.0735	0.3861	0.039*
C19	1.1063 (12)	0.2905 (3)	0.4660 (3)	0.0525 (14)
C20	1.244 (3)	0.4000 (7)	0.5078 (9)	0.065 (4)	0.493 (17)
H20A	1.0810	0.4252	0.4906	0.078*	0.493 (17)
H20B	1.2509	0.3847	0.5610	0.078*	0.493 (17)
C21	1.483 (3)	0.4465 (6)	0.4943 (9)	0.066 (4)	0.493 (17)
H21A	1.4944	0.4896	0.5267	0.098*	0.493 (17)
H21B	1.4645	0.4615	0.4414	0.098*	0.493 (17)
H21C	1.6374	0.4173	0.5066	0.098*	0.493 (17)
C20A	1.343 (4)	0.4184 (10)	0.4745 (8)	0.074 (5)	0.507 (17)
H20C	1.4622	0.4431	0.4452	0.088*	0.507 (17)
H20D	1.1854	0.4470	0.4749	0.088*	0.507 (17)
C21A	1.470 (3)	0.3911 (11)	0.5553 (10)	0.103 (7)	0.507 (17)
H21D	1.4901	0.4322	0.5904	0.155*	0.507 (17)
H21E	1.6372	0.3701	0.5517	0.155*	0.507 (17)
H21F	1.3610	0.3543	0.5737	0.155*	0.507 (17)

	U11	U22	U33	U12	U13	U23
O1	0.0360 (15)	0.0291 (14)	0.0376 (15)	0.0107 (12)	−0.0006 (12)	−0.0021 (11)
O2	0.0347 (15)	0.0267 (14)	0.0483 (17)	0.0047 (11)	−0.0064 (13)	−0.0026 (12)
O3	0.126 (4)	0.056 (2)	0.043 (2)	0.035 (3)	0.014 (2)	−0.0126 (18)
O4	0.102 (4)	0.056 (3)	0.152 (6)	−0.014 (3)	0.003 (4)	−0.071 (3)
C1	0.0237 (15)	0.0251 (17)	0.0286 (17)	0.0035 (12)	0.0027 (13)	−0.0016 (13)
C2	0.0257 (16)	0.0246 (17)	0.0311 (18)	−0.0002 (13)	0.0050 (14)	−0.0010 (13)
C3	0.0293 (19)	0.034 (2)	0.036 (2)	0.0037 (15)	−0.0017 (16)	−0.0033 (16)
C4	0.034 (2)	0.042 (2)	0.037 (2)	0.0004 (17)	−0.0010 (17)	−0.0098 (18)
C5	0.0343 (19)	0.0318 (19)	0.0340 (19)	−0.0042 (16)	0.0048 (16)	−0.0082 (15)
C6	0.0308 (18)	0.0262 (18)	0.0315 (18)	−0.0034 (14)	0.0069 (15)	−0.0025 (14)
C7	0.042 (2)	0.0202 (16)	0.039 (2)	−0.0004 (15)	0.0101 (17)	−0.0030 (14)
C8	0.041 (2)	0.0174 (16)	0.043 (2)	0.0069 (15)	0.0071 (17)	−0.0006 (15)
C9	0.0309 (18)	0.0197 (15)	0.0367 (19)	0.0027 (13)	0.0023 (15)	0.0004 (14)
C10	0.0268 (17)	0.0191 (15)	0.0306 (17)	0.0019 (12)	0.0053 (14)	0.0026 (13)
C11	0.0241 (16)	0.0217 (15)	0.0283 (16)	−0.0006 (12)	0.0054 (13)	−0.0006 (12)
C12	0.0269 (16)	0.0202 (15)	0.0324 (17)	0.0021 (13)	0.0024 (13)	0.0033 (13)
N1	0.0261 (14)	0.0195 (13)	0.0302 (15)	0.0014 (11)	0.0028 (12)	−0.0017 (11)
C13	0.0255 (16)	0.0226 (16)	0.0295 (17)	0.0059 (13)	0.0008 (13)	−0.0019 (13)
C14	0.0282 (17)	0.0219 (16)	0.0370 (19)	0.0033 (13)	0.0052 (14)	−0.0028 (14)
C15	0.0288 (18)	0.0224 (17)	0.051 (2)	0.0011 (14)	0.0009 (17)	−0.0081 (16)
C16	0.041 (2)	0.0303 (19)	0.0328 (19)	0.0131 (16)	−0.0068 (16)	−0.0080 (15)
C17	0.039 (2)	0.041 (2)	0.0277 (18)	0.0122 (17)	0.0023 (16)	−0.0033 (16)
C18	0.0335 (19)	0.033 (2)	0.0305 (18)	0.0038 (15)	0.0059 (15)	0.0003 (15)
C19	0.075 (4)	0.032 (2)	0.044 (2)	0.021 (2)	−0.013 (2)	−0.0114 (19)
C20	0.092 (11)	0.041 (6)	0.058 (8)	−0.012 (6)	0.003 (7)	−0.022 (6)
C21	0.079 (9)	0.033 (5)	0.085 (10)	−0.031 (6)	0.014 (8)	−0.014 (5)
C20A	0.082 (12)	0.074 (11)	0.068 (9)	0.014 (9)	0.023 (8)	−0.015 (8)
C21A	0.068 (11)	0.102 (14)	0.15 (2)	0.012 (9)	0.047 (12)	0.023 (13)

O1—C1	1.217 (5)	C12—N1	1.405 (4)
O2—C12	1.210 (5)	N1—C13	1.448 (5)
O3—C19	1.188 (7)	C13—C14	1.379 (5)
O4—C19	1.300 (9)	C13—C18	1.387 (5)
O4—C20	1.576 (14)	C14—C15	1.389 (5)
O4—C20A	1.581 (19)	C14—H14A	0.9300
C1—N1	1.406 (5)	C15—C16	1.394 (6)
C1—C2	1.468 (5)	C15—H15A	0.9300
C2—C3	1.377 (5)	C16—C17	1.387 (7)
C2—C11	1.410 (5)	C16—C19	1.494 (6)
C3—C4	1.417 (6)	C17—C18	1.386 (6)
C3—H3A	0.9300	C17—H17A	0.9300
C4—C5	1.375 (6)	C18—H18A	0.9300
C4—H4A	0.9300	C20—C21	1.546 (10)
C5—C6	1.402 (6)	C20—H20A	0.9700
C5—H5A	0.9300	C20—H20B	0.9700
C6—C7	1.415 (6)	C21—H21A	0.9600
C6—C11	1.424 (5)	C21—H21B	0.9600
C7—C8	1.370 (6)	C21—H21C	0.9600
C7—H7A	0.9300	C20A—C21A	1.555 (10)
C8—C9	1.409 (5)	C20A—H20C	0.9700
C8—H8A	0.9300	C20A—H20D	0.9700
C9—C10	1.376 (5)	C21A—H21D	0.9600
C9—H9A	0.9300	C21A—H21E	0.9600
C10—C11	1.410 (5)	C21A—H21F	0.9600
C10—C12	1.476 (5)
C19—O4—C20	98.9 (7)	C1—N1—C13	116.7 (3)
C19—O4—C20A	129.7 (8)	C14—C13—C18	122.0 (4)
C20—O4—C20A	33.0 (6)	C14—C13—N1	120.5 (3)
O1—C1—N1	119.7 (3)	C18—C13—N1	117.5 (3)
O1—C1—C2	123.7 (3)	C13—C14—C15	119.1 (4)
N1—C1—C2	116.6 (3)	C13—C14—H14A	120.5
C3—C2—C11	120.8 (3)	C15—C14—H14A	120.5
C3—C2—C1	118.9 (3)	C14—C15—C16	119.9 (4)
C11—C2—C1	120.2 (3)	C14—C15—H15A	120.1
C2—C3—C4	119.7 (4)	C16—C15—H15A	120.1
C2—C3—H3A	120.1	C17—C16—C15	120.0 (4)
C4—C3—H3A	120.1	C17—C16—C19	117.7 (4)
C5—C4—C3	120.3 (4)	C15—C16—C19	122.3 (5)
C5—C4—H4A	119.8	C18—C17—C16	120.6 (4)
C3—C4—H4A	119.8	C18—C17—H17A	119.7
C4—C5—C6	120.8 (4)	C16—C17—H17A	119.7
C4—C5—H5A	119.6	C17—C18—C13	118.5 (4)
C6—C5—H5A	119.6	C17—C18—H18A	120.8
C5—C6—C7	122.5 (4)	C13—C18—H18A	120.8
C5—C6—C11	119.3 (3)	O3—C19—O4	123.3 (5)
C7—C6—C11	118.2 (3)	O3—C19—C16	124.6 (6)
C8—C7—C6	121.4 (4)	O4—C19—C16	112.0 (5)
C8—C7—H7A	119.3	C21—C20—O4	96.2 (9)
C6—C7—H7A	119.3	C21—C20—H20A	112.5
C7—C8—C9	119.7 (4)	O4—C20—H20A	112.5
C7—C8—H8A	120.1	C21—C20—H20B	112.5
C9—C8—H8A	120.1	O4—C20—H20B	112.5
C10—C9—C8	121.0 (4)	H20A—C20—H20B	110.0
C10—C9—H9A	119.5	C21A—C20A—O4	86.6 (13)
C8—C9—H9A	119.5	C21A—C20A—H20C	114.2
C9—C10—C11	119.8 (3)	O4—C20A—H20C	114.2
C9—C10—C12	119.7 (3)	C21A—C20A—H20D	114.2
C11—C10—C12	120.4 (3)	O4—C20A—H20D	114.2
C2—C11—C10	121.0 (3)	H20C—C20A—H20D	111.4
C2—C11—C6	119.1 (3)	C20A—C21A—H21D	109.5
C10—C11—C6	119.9 (3)	C20A—C21A—H21E	109.5
O2—C12—N1	120.3 (3)	H21D—C21A—H21E	109.5
O2—C12—C10	123.7 (3)	C20A—C21A—H21F	109.5
N1—C12—C10	116.0 (3)	H21D—C21A—H21F	109.5
C12—N1—C1	125.5 (3)	H21E—C21A—H21F	109.5
C12—N1—C13	117.8 (3)
O1—C1—C2—C3	−1.1 (6)	C10—C12—N1—C1	−5.3 (5)
N1—C1—C2—C3	179.1 (4)	O2—C12—N1—C13	−7.6 (5)
O1—C1—C2—C11	179.5 (4)	C10—C12—N1—C13	171.5 (3)
N1—C1—C2—C11	−0.3 (5)	O1—C1—N1—C12	−175.6 (4)
C11—C2—C3—C4	1.3 (6)	C2—C1—N1—C12	4.3 (5)
C1—C2—C3—C4	−178.1 (4)	O1—C1—N1—C13	7.6 (5)
C2—C3—C4—C5	−0.3 (7)	C2—C1—N1—C13	−172.6 (3)
C3—C4—C5—C6	−0.4 (7)	C12—N1—C13—C14	76.6 (4)
C4—C5—C6—C7	−179.1 (4)	C1—N1—C13—C14	−106.3 (4)
C4—C5—C6—C11	0.1 (6)	C12—N1—C13—C18	−104.4 (4)
C5—C6—C7—C8	178.5 (4)	C1—N1—C13—C18	72.7 (4)
C11—C6—C7—C8	−0.8 (6)	C18—C13—C14—C15	−0.3 (6)
C6—C7—C8—C9	0.4 (6)	N1—C13—C14—C15	178.6 (3)
C7—C8—C9—C10	0.8 (6)	C13—C14—C15—C16	−0.2 (6)
C8—C9—C10—C11	−1.4 (6)	C14—C15—C16—C17	0.7 (6)
C8—C9—C10—C12	178.5 (4)	C14—C15—C16—C19	−177.7 (4)
C3—C2—C11—C10	178.4 (4)	C15—C16—C17—C18	−0.6 (6)
C1—C2—C11—C10	−2.2 (5)	C19—C16—C17—C18	177.9 (4)
C3—C2—C11—C6	−1.6 (5)	C16—C17—C18—C13	0.1 (6)
C1—C2—C11—C6	177.8 (3)	C14—C13—C18—C17	0.3 (6)
C9—C10—C11—C2	−179.0 (4)	N1—C13—C18—C17	−178.6 (3)
C12—C10—C11—C2	1.1 (5)	C20—O4—C19—O3	0.3 (10)
C9—C10—C11—C6	1.0 (5)	C20A—O4—C19—O3	−13.0 (13)
C12—C10—C11—C6	−179.0 (3)	C20—O4—C19—C16	176.7 (7)
C5—C6—C11—C2	0.8 (5)	C20A—O4—C19—C16	163.4 (9)
C7—C6—C11—C2	−179.9 (4)	C17—C16—C19—O3	−4.0 (7)
C5—C6—C11—C10	−179.1 (4)	C15—C16—C19—O3	174.4 (5)
C7—C6—C11—C10	0.2 (5)	C17—C16—C19—O4	179.7 (5)
C9—C10—C12—O2	1.7 (6)	C15—C16—C19—O4	−1.9 (7)
C11—C10—C12—O2	−178.4 (4)	C19—O4—C20—C21	176.4 (10)
C9—C10—C12—N1	−177.4 (3)	C20A—O4—C20—C21	−22.5 (12)
C11—C10—C12—N1	2.5 (5)	C19—O4—C20A—C21A	84.2 (13)
O2—C12—N1—C1	175.5 (4)	C20—O4—C20A—C21A	59.5 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O3i	0.93	2.60	3.249 (4)	127
C14—H14A···O1ii	0.93	2.41	3.312 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O3i	0.93	2.60	3.249 (4)	127
C14—H14A⋯O1ii	0.93	2.41	3.312 (3)	165

Symmetry codes: (i) ; (ii) .