organic compounds
2-Chloro-3-[(2-oxo-2H-chromen-6-yl)amino]naphthalene-1,4-dione
aDepartamento de Química Inorgânica, Universidade Federal Fluminense, Niterói, CEP 24-020-140, Rio de Janeiro, Brazil
*Correspondence e-mail: jagomez@vm.uff.br
In the title compound, C19H10ClNO4, the dihedral angle between the naphthoquinone and coumarin rings is 48.99 (6)°. In the crystal, molecules are linked by strong N—H⋯O hydrogen bonds into chains with graph-set motif C(6) along [101]. The packing also features π–π stacking interactions between naphthoquinone and coumarin rings [centroid-to-centroid distances = 3.7679 (12) and 3.6180 (13) Å].
Related literature
For related compounds see: Rózsa et al. (1989); Ito et al. (1993); Ishikawa et al. (1995); Padwal et al. (2011). For reference structural data, see: Ibis & Deniz (2012); Resende & Gomez (2012). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; 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: WinGX (Farrugia, 2012).
Supporting information
10.1107/S1600536813019922/bx2446sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813019922/bx2446Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813019922/bx2446Isup3.cml
2,3-Dichloro-1,4-naphthoquinone (681 mg, 3 mmol) was added to a solution of 6-aminocoumarin (579.6 mg, 3.6 mmol) in DMF (10 ml). The mixture was stirred at 60–70°C for 72 h. The solvent was evaporated under reduced pressure and the crude product was purified through recrystallization in hexane, resulting in a red solid. Yield: 833.8 mg, 79%. Single crystals suitable for a study of X-ray diffraction of compound (I) were obtained at 4°C by slow evaporation of an acetonitrile–dichloromethane (1:1) solution. m.p. 301°C. Found: C, 64.12; H, 2.91; N, 4.14. Calc. for C19H10ClNO4: C, 64.51; H, 3.42; N, 3.96%. 1H NMR (300 MHz, d6-DMSO): δ 8.16 (d, J = 7.5 Hz, 2H), 8.13 (d, J = 9.6 Hz, 1H), 8.00 (t, J = 7.5 Hz, 1H), 7.94 (t, J = 7.5 Hz, 1H), 7.58–7.52 (m, 2H), 7.48 (d, J = 8.7 Hz, 1H), 6.62 (d, J = 9.6 Hz, 1H). 13 C NMR - APT (d6-DMSO, 75 MHz): δ 180.0, 176.8, 160.0, 150.4, 144.0, 143.3, 135.5, 134.8, 133.4, 131.9, 130.3, 128.0, 126.7, 126.2, 122.7, 118.2, 116.7, 116.0, 114.7. IR (KBr): νC═O (quin.) = 1672, νC═O (ester) = 1720, νC—O (ester) = 1568, 1290, νN—H = 3294, νC—H (arom.) = 3080. UV–Vis [CH3CN; λ/nm (log ε)]: 277 (4.10), 333 (3.28), 469 (3.10).
All C-bound H atoms were placed in calculated idealized positions. The N-bound H atom was placed in the calculated idealized position. All H atoms were refined with fixed individual displacement parameters [Uiso(H) = 1.2Ueq using a riding model.
Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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: WinGX (Farrugia, 2012).C19H10ClNO4 | F(000) = 720 |
Mr = 351.73 | Dx = 1.596 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 5237 reflections |
a = 10.9371 (5) Å | θ = 2.0–29.5° |
b = 10.4462 (5) Å | µ = 0.29 mm−1 |
c = 13.5104 (7) Å | T = 150 K |
β = 108.533 (5)° | Prism, violet |
V = 1463.53 (12) Å3 | 0.23 × 0.13 × 0.07 mm |
Z = 4 |
Oxford Xcalibur Gemini Ultra diffractometer with Atlas detector | 3527 independent reflections |
Graphite monochromator | 2714 reflections with I > 2σ(I) |
Detector resolution: 10.4186 pixels mm-1 | Rint = 0.055 |
ω scans | θmax = 28.5°, θmin = 2.8° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | h = −14→14 |
Tmin = 0.947, Tmax = 1 | k = −13→13 |
15281 measured reflections | l = −18→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.065 | w = 1/[σ2(Fo2) + (0.029P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.91 | (Δ/σ)max < 0.001 |
3527 reflections | Δρmax = 0.23 e Å−3 |
226 parameters | Δρmin = −0.21 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 1217 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.07 (5) |
C19H10ClNO4 | V = 1463.53 (12) Å3 |
Mr = 351.73 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 10.9371 (5) Å | µ = 0.29 mm−1 |
b = 10.4462 (5) Å | T = 150 K |
c = 13.5104 (7) Å | 0.23 × 0.13 × 0.07 mm |
β = 108.533 (5)° |
Oxford Xcalibur Gemini Ultra diffractometer with Atlas detector | 3527 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 2714 reflections with I > 2σ(I) |
Tmin = 0.947, Tmax = 1 | Rint = 0.055 |
15281 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.065 | Δρmax = 0.23 e Å−3 |
S = 0.91 | Δρmin = −0.21 e Å−3 |
3527 reflections | Absolute structure: Flack (1983), 1217 Friedel pairs |
226 parameters | Absolute structure parameter: −0.07 (5) |
2 restraints |
Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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 | ||
Cl | 0.31971 (5) | 0.30204 (5) | 0.61162 (4) | 0.02411 (12) | |
O4 | 0.57743 (16) | −0.02583 (15) | 0.22630 (13) | 0.0366 (4) | |
O3 | 0.39509 (13) | 0.03816 (14) | 0.24617 (11) | 0.0246 (4) | |
O1 | −0.11020 (14) | 0.09274 (14) | 0.55900 (12) | 0.0292 (4) | |
O2 | 0.31861 (14) | 0.29316 (15) | 0.82346 (11) | 0.0279 (4) | |
N1 | 0.07529 (16) | 0.14446 (17) | 0.48249 (13) | 0.0208 (4) | |
H1 | −0.0048 | 0.1431 | 0.4453 | 0.025* | |
C2 | 0.20172 (19) | 0.23128 (19) | 0.65296 (15) | 0.0182 (5) | |
C3 | 0.09915 (19) | 0.17092 (18) | 0.58553 (15) | 0.0179 (5) | |
C14 | 0.3192 (2) | 0.0628 (2) | 0.30908 (16) | 0.0197 (5) | |
C9 | 0.11248 (18) | 0.2050 (2) | 0.80240 (15) | 0.0182 (4) | |
C1 | 0.2201 (2) | 0.2472 (2) | 0.76414 (17) | 0.0187 (4) | |
C11 | 0.16331 (19) | 0.11893 (19) | 0.42803 (15) | 0.0183 (4) | |
C10 | −0.00065 (19) | 0.1522 (2) | 0.73331 (16) | 0.0192 (5) | |
C13 | 0.2008 (2) | 0.1182 (2) | 0.26179 (16) | 0.0214 (5) | |
H13 | 0.173 | 0.1363 | 0.1891 | 0.026* | |
C4 | −0.0132 (2) | 0.13481 (18) | 0.62218 (16) | 0.0191 (5) | |
C12 | 0.1236 (2) | 0.14658 (19) | 0.32122 (16) | 0.0211 (5) | |
H12 | 0.042 | 0.1856 | 0.2895 | 0.025* | |
C15 | 0.36188 (19) | 0.03463 (19) | 0.41469 (17) | 0.0195 (5) | |
C16 | 0.28168 (19) | 0.06194 (19) | 0.47438 (16) | 0.0202 (5) | |
H16 | 0.3085 | 0.0414 | 0.5466 | 0.024* | |
C19 | 0.5182 (2) | −0.0122 (2) | 0.28635 (19) | 0.0269 (5) | |
C18 | 0.5609 (2) | −0.0425 (2) | 0.39665 (18) | 0.0258 (5) | |
H18 | 0.6438 | −0.0795 | 0.4265 | 0.031* | |
C8 | 0.1236 (2) | 0.2211 (2) | 0.90669 (17) | 0.0240 (5) | |
H8 | 0.1993 | 0.258 | 0.9536 | 0.029* | |
C5 | −0.1001 (2) | 0.1138 (2) | 0.76989 (17) | 0.0243 (5) | |
H5 | −0.1765 | 0.0775 | 0.7235 | 0.029* | |
C6 | −0.0869 (2) | 0.1289 (2) | 0.87452 (18) | 0.0265 (5) | |
H6 | −0.1543 | 0.1017 | 0.9 | 0.032* | |
C7 | 0.0230 (2) | 0.1829 (2) | 0.94223 (17) | 0.0264 (5) | |
H7 | 0.0301 | 0.1942 | 1.0136 | 0.032* | |
C17 | 0.4889 (2) | −0.0209 (2) | 0.45813 (18) | 0.0249 (5) | |
H17 | 0.5209 | −0.0419 | 0.5302 | 0.03* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.0214 (2) | 0.0303 (3) | 0.0225 (2) | −0.0092 (3) | 0.0095 (2) | −0.0010 (3) |
O4 | 0.0313 (10) | 0.0461 (11) | 0.0399 (10) | 0.0050 (8) | 0.0221 (8) | −0.0034 (8) |
O3 | 0.0222 (8) | 0.0287 (9) | 0.0246 (9) | 0.0013 (7) | 0.0101 (7) | −0.0018 (6) |
O1 | 0.0234 (9) | 0.0360 (10) | 0.0286 (9) | −0.0082 (7) | 0.0091 (7) | −0.0020 (7) |
O2 | 0.0187 (8) | 0.0391 (10) | 0.0252 (8) | −0.0062 (7) | 0.0060 (7) | −0.0032 (7) |
N1 | 0.0147 (9) | 0.0263 (10) | 0.0214 (10) | −0.0009 (7) | 0.0055 (8) | −0.0011 (7) |
C2 | 0.0175 (11) | 0.0185 (12) | 0.0225 (12) | −0.0010 (8) | 0.0120 (9) | 0.0029 (8) |
C3 | 0.0188 (11) | 0.0156 (11) | 0.0196 (11) | 0.0036 (9) | 0.0065 (9) | 0.0045 (8) |
C14 | 0.0191 (11) | 0.0205 (11) | 0.0206 (11) | −0.0041 (9) | 0.0079 (9) | −0.0025 (9) |
C9 | 0.0186 (11) | 0.0159 (10) | 0.0226 (11) | 0.0040 (9) | 0.0099 (9) | 0.0033 (9) |
C1 | 0.0152 (10) | 0.0172 (11) | 0.0231 (11) | 0.0033 (8) | 0.0053 (9) | 0.0011 (8) |
C11 | 0.0190 (10) | 0.0176 (11) | 0.0199 (11) | −0.0042 (9) | 0.0085 (9) | −0.0047 (9) |
C10 | 0.0170 (11) | 0.0149 (11) | 0.0279 (12) | 0.0057 (8) | 0.0103 (9) | 0.0041 (9) |
C13 | 0.0230 (11) | 0.0235 (12) | 0.0165 (11) | −0.0028 (9) | 0.0045 (9) | −0.0022 (9) |
C4 | 0.0177 (11) | 0.0140 (11) | 0.0253 (12) | 0.0014 (9) | 0.0066 (10) | 0.0015 (9) |
C12 | 0.0166 (10) | 0.0204 (12) | 0.0235 (12) | −0.0001 (9) | 0.0027 (9) | −0.0007 (9) |
C15 | 0.0160 (11) | 0.0161 (11) | 0.0261 (12) | −0.0014 (8) | 0.0065 (9) | −0.0005 (8) |
C16 | 0.0210 (11) | 0.0207 (12) | 0.0186 (11) | 0.0007 (9) | 0.0060 (9) | −0.0004 (8) |
C19 | 0.0231 (12) | 0.0208 (12) | 0.0390 (14) | 0.0007 (10) | 0.0127 (11) | −0.0014 (10) |
C18 | 0.0183 (12) | 0.0252 (13) | 0.0328 (13) | 0.0053 (9) | 0.0067 (10) | 0.0037 (10) |
C8 | 0.0224 (12) | 0.0268 (13) | 0.0231 (12) | 0.0055 (9) | 0.0076 (10) | 0.0029 (9) |
C5 | 0.0201 (11) | 0.0201 (12) | 0.0360 (14) | 0.0017 (9) | 0.0135 (10) | 0.0020 (10) |
C6 | 0.0232 (12) | 0.0298 (14) | 0.0338 (14) | 0.0067 (10) | 0.0194 (11) | 0.0070 (10) |
C7 | 0.0270 (12) | 0.0339 (15) | 0.0230 (12) | 0.0098 (11) | 0.0146 (10) | 0.0059 (10) |
C17 | 0.0245 (13) | 0.0222 (12) | 0.0262 (12) | 0.0014 (10) | 0.0054 (11) | 0.0028 (10) |
Cl—C2 | 1.7268 (19) | C10—C5 | 1.389 (3) |
O4—C19 | 1.197 (2) | C10—C4 | 1.475 (3) |
O3—C19 | 1.385 (3) | C13—C12 | 1.370 (3) |
O3—C14 | 1.387 (2) | C13—H13 | 0.95 |
O1—C4 | 1.213 (2) | C12—H12 | 0.95 |
O2—C1 | 1.219 (3) | C15—C16 | 1.397 (3) |
N1—C3 | 1.361 (2) | C15—C17 | 1.446 (3) |
N1—C11 | 1.411 (2) | C16—H16 | 0.95 |
N1—H1 | 0.86 | C19—C18 | 1.448 (3) |
C2—C3 | 1.355 (3) | C18—C17 | 1.333 (3) |
C2—C1 | 1.460 (3) | C18—H18 | 0.95 |
C3—C4 | 1.511 (3) | C8—C7 | 1.391 (3) |
C14—C13 | 1.376 (3) | C8—H8 | 0.95 |
C14—C15 | 1.385 (3) | C5—C6 | 1.384 (3) |
C9—C8 | 1.386 (3) | C5—H5 | 0.95 |
C9—C10 | 1.404 (3) | C6—C7 | 1.379 (3) |
C9—C1 | 1.494 (3) | C6—H6 | 0.95 |
C11—C16 | 1.381 (3) | C7—H7 | 0.95 |
C11—C12 | 1.399 (3) | C17—H17 | 0.95 |
C19—O3—C14 | 121.75 (17) | C13—C12—C11 | 120.85 (19) |
C3—N1—C11 | 129.15 (18) | C13—C12—H12 | 119.6 |
C3—N1—H1 | 115.4 | C11—C12—H12 | 119.6 |
C11—N1—H1 | 115.4 | C14—C15—C16 | 118.94 (18) |
C3—C2—C1 | 123.94 (18) | C14—C15—C17 | 117.96 (18) |
C3—C2—Cl | 121.72 (15) | C16—C15—C17 | 123.1 (2) |
C1—C2—Cl | 114.29 (15) | C11—C16—C15 | 119.77 (19) |
C2—C3—N1 | 129.12 (18) | C11—C16—H16 | 120.1 |
C2—C3—C4 | 118.78 (17) | C15—C16—H16 | 120.1 |
N1—C3—C4 | 111.90 (17) | O4—C19—O3 | 116.6 (2) |
C13—C14—C15 | 121.78 (18) | O4—C19—C18 | 127.2 (2) |
C13—C14—O3 | 116.84 (18) | O3—C19—C18 | 116.22 (18) |
C15—C14—O3 | 121.37 (18) | C17—C18—C19 | 122.9 (2) |
C8—C9—C10 | 119.83 (18) | C17—C18—H18 | 118.6 |
C8—C9—C1 | 119.46 (18) | C19—C18—H18 | 118.6 |
C10—C9—C1 | 120.69 (17) | C9—C8—C7 | 119.5 (2) |
O2—C1—C2 | 121.67 (19) | C9—C8—H8 | 120.2 |
O2—C1—C9 | 121.19 (19) | C7—C8—H8 | 120.2 |
C2—C1—C9 | 117.14 (18) | C6—C5—C10 | 119.4 (2) |
C16—C11—C12 | 119.73 (18) | C6—C5—H5 | 120.3 |
C16—C11—N1 | 122.81 (18) | C10—C5—H5 | 120.3 |
C12—C11—N1 | 117.36 (18) | C7—C6—C5 | 120.7 (2) |
C5—C10—C9 | 120.07 (19) | C7—C6—H6 | 119.7 |
C5—C10—C4 | 119.79 (19) | C5—C6—H6 | 119.7 |
C9—C10—C4 | 120.13 (18) | C6—C7—C8 | 120.4 (2) |
C12—C13—C14 | 118.92 (19) | C6—C7—H7 | 119.8 |
C12—C13—H13 | 120.5 | C8—C7—H7 | 119.8 |
C14—C13—H13 | 120.5 | C18—C17—C15 | 119.8 (2) |
O1—C4—C10 | 122.55 (18) | C18—C17—H17 | 120.1 |
O1—C4—C3 | 118.71 (18) | C15—C17—H17 | 120.1 |
C10—C4—C3 | 118.74 (18) | ||
C1—C2—C3—N1 | −176.13 (19) | N1—C3—C4—O1 | −2.7 (3) |
Cl—C2—C3—N1 | 6.5 (3) | C2—C3—C4—C10 | −7.3 (3) |
C1—C2—C3—C4 | 9.5 (3) | N1—C3—C4—C10 | 177.40 (17) |
Cl—C2—C3—C4 | −167.80 (14) | C14—C13—C12—C11 | −0.6 (3) |
C11—N1—C3—C2 | 30.9 (3) | C16—C11—C12—C13 | −0.2 (3) |
C11—N1—C3—C4 | −154.41 (19) | N1—C11—C12—C13 | −176.49 (18) |
C19—O3—C14—C13 | 177.18 (19) | C13—C14—C15—C16 | 0.7 (3) |
C19—O3—C14—C15 | −1.9 (3) | O3—C14—C15—C16 | 179.77 (18) |
C3—C2—C1—O2 | 174.1 (2) | C13—C14—C15—C17 | −178.7 (2) |
Cl—C2—C1—O2 | −8.4 (3) | O3—C14—C15—C17 | 0.4 (3) |
C3—C2—C1—C9 | −6.0 (3) | C12—C11—C16—C15 | 1.2 (3) |
Cl—C2—C1—C9 | 171.51 (14) | N1—C11—C16—C15 | 177.35 (18) |
C8—C9—C1—O2 | 1.6 (3) | C14—C15—C16—C11 | −1.5 (3) |
C10—C9—C1—O2 | 179.98 (19) | C17—C15—C16—C11 | 177.8 (2) |
C8—C9—C1—C2 | −178.30 (18) | C14—O3—C19—O4 | −177.49 (19) |
C10—C9—C1—C2 | 0.1 (3) | C14—O3—C19—C18 | 2.5 (3) |
C3—N1—C11—C16 | 29.8 (3) | O4—C19—C18—C17 | 178.2 (2) |
C3—N1—C11—C12 | −154.0 (2) | O3—C19—C18—C17 | −1.8 (3) |
C8—C9—C10—C5 | −1.4 (3) | C10—C9—C8—C7 | 1.0 (3) |
C1—C9—C10—C5 | −179.75 (18) | C1—C9—C8—C7 | 179.39 (19) |
C8—C9—C10—C4 | 179.97 (18) | C9—C10—C5—C6 | 0.5 (3) |
C1—C9—C10—C4 | 1.6 (3) | C4—C10—C5—C6 | 179.15 (19) |
C15—C14—C13—C12 | 0.4 (3) | C10—C5—C6—C7 | 0.8 (3) |
O3—C14—C13—C12 | −178.74 (18) | C5—C6—C7—C8 | −1.2 (3) |
C5—C10—C4—O1 | 3.3 (3) | C9—C8—C7—C6 | 0.3 (3) |
C9—C10—C4—O1 | −178.1 (2) | C19—C18—C17—C15 | 0.4 (3) |
C5—C10—C4—C3 | −176.81 (17) | C14—C15—C17—C18 | 0.4 (3) |
C9—C10—C4—C3 | 1.9 (3) | C16—C15—C17—C18 | −179.0 (2) |
C2—C3—C4—O1 | 172.59 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.21 | 3.015 (2) | 157 |
Symmetry code: (i) x−1/2, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.21 | 3.015 (2) | 156.7 |
Symmetry code: (i) x−1/2, −y+1/2, z−1/2. |
Acknowledgements
This work was supported by the Brazilian agencies Proppi–UFF, FAPERJ, Scholarship Postgraduate Students Agreement Program – PEC-PG, CAPES/CNPq – Brazil and CAPES. The authors thank the X-ray diffraction laboratory LabCri-UFMG for the data collection, Professor Jackson A. L. C. Resende (IQ-UFF), and Professor M. D. Vargas (IQ-UFF) for her help and encouragement.
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There are very few examples in the literature of coumarin–naphthoquinone conjugates, most of them (direct C—C bond) are from natural sources (Rózsa et al., 1989; Ito et al., 1993; Ishikawa et al., 1995; Padwal et al., 2011) and only one synthetic, the coumarin–naphthoquinone hybrid linked through sulfur spacer attached at 7-position of the coumarin ring and 2-position of the naphthoquinone [2-(7-sulphanyl-4-methyl-coumarinyl)-3-(1-ethoxy)-1,4-naphthoquinone; Ibis & Deniz, 2012]. The title compound (I) is the product of the reaction of 2,3-dicloro-1,4-naphtoquionone with 6-aminocoumarin. The average C—C, C—O, C═O and C—N bond distances are in agreement with those observed in tert-butyl N-{3-[(3-chloro-1,4-dioxo-1,4-dihydronaphthalen2-yl)amino]propyl}carbamate (Resende & Gomez, 2012). The angle between the naphthoquinone and coumarin planes is 48.99 (6)°. The molecular structure is stabilized by one intramolecular N—H···O hydrogen bond. In the crystal, molecules are linked by strong N—H···O hydrogen bonds into chains with graph-set notation C(6) along [101] (Bernstein et al., 1995). The packing also features π–π stacking interactions between naphthoquinone and coumarin rings [centroid–centroid distances = 3.7679 (12) and 3.6180 (13) Å]. The dihedral angle between naphthoquinone and coumarin rings is 48.99 (6)°.