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The title compound, C17H13NO4, exists as a planar mol­ecule; adjacent mol­ecules are linked by electrostatic C-H...O [C...O = 3.318 (4) and 3.455 (4) Å] interactions into a linear chain.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100009136/qa0343sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100009136/qa0343Isup2.hkl
Contains datablock I

CCDC reference: 150392

Comment top

Our observation that the fluorescence quantum yield (relative to quinine sulfate) of 7-methoxy-3-(salicylideneamino)coumarin, (I), in methanol is twice that of unsubstituted 3-(salicylideneamino)coumarin in methanol prompted us to carry out an X-ray analysis of (I). Compound (I) exists as discrete molecules; however, adjacent molecules are linked by a pair of C—H···O interactions into chains. These interactions are not van der Waals contacts; these are electrostatic attractions, as the distances and angles compare well with values accepted for conventional C—H···X hydrogen bonding (Iyere et al., 1998; Ng, 1999). Such interactions are not present in, for example, coumarin-3-carboxylic acid (Dobson & Gerkin, 1996) and 3-(2-benzothiazolyl)-7-(diethylamino)coumarin (Jasinski & Paight, 1995); in these two compounds, the 4- and 5-positions of the coumarin unit are not substituted.

Experimental top

7-Methoxy-3-aminocoumarin (Khoo, 1999) was condensed with salicylaldehyde in chloroform to yield the Schiff base (m.p. 410–411 K) in 60% yield. CNH elemental analysis: found (calculated) for C17H13NO4: C 68.50 (69.15), H 3.56 (4.41), N 4.87% (4.75%). Yellow–orange plates were obtained upon recrystallization with benzene.

Computing details top

Data collection: XSCANS (Siemens, 1998); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

7-Methoxy-3-(salicylideneamino)coumarin top
Crystal data top
C17H13NO4F(000) = 616
Mr = 295.28Dx = 1.425 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.660 (1) ÅCell parameters from 24 reflections
b = 31.984 (8) Åθ = 3.5–12.5°
c = 7.123 (2) ŵ = 0.10 mm1
β = 114.93 (2)°T = 298 K
V = 1375.9 (6) Å3Plate, yellow
Z = 40.60 × 0.40 × 0.14 mm
Data collection top
Siemens P4 four-circle
diffractometer
1449 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
ω scansh = 17
Absorption correction: empirical (using intensity measurements)
via ψ scan (North et al., 1968)
k = 138
Tmin = 0.875, Tmax = 0.966l = 88
3194 measured reflections3 standard reflections every 97 reflections
2416 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.172 w = 1/[σ2(Fo2) + (0.0731P)2 + 0.6431P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2416 reflectionsΔρmax = 0.24 e Å3
202 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.002 (1)
Crystal data top
C17H13NO4V = 1375.9 (6) Å3
Mr = 295.28Z = 4
Monoclinic, P21/nMo Kα radiation
a = 6.660 (1) ŵ = 0.10 mm1
b = 31.984 (8) ÅT = 298 K
c = 7.123 (2) Å0.60 × 0.40 × 0.14 mm
β = 114.93 (2)°
Data collection top
Siemens P4 four-circle
diffractometer
1449 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements)
via ψ scan (North et al., 1968)
Rint = 0.027
Tmin = 0.875, Tmax = 0.9663 standard reflections every 97 reflections
3194 measured reflections intensity decay: none
2416 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.172H-atom parameters constrained
S = 1.05Δρmax = 0.24 e Å3
2416 reflectionsΔρmin = 0.24 e Å3
202 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.1196 (3)0.2142 (1)0.7412 (4)0.042 (1)
O21.2663 (4)0.2757 (1)0.7495 (5)0.057 (1)
O30.8488 (4)0.0768 (1)0.7442 (4)0.055 (1)
O40.6349 (5)0.3785 (1)0.8008 (5)0.062 (1)
N10.8780 (4)0.3180 (1)0.7586 (4)0.037 (1)
C10.9576 (5)0.3900 (1)0.7389 (5)0.040 (1)
C20.7764 (6)0.4049 (1)0.7712 (5)0.046 (1)
C30.7418 (7)0.4473 (1)0.7733 (6)0.059 (1)
C40.8810 (7)0.4753 (1)0.7440 (6)0.059 (1)
C51.0596 (6)0.4615 (1)0.7103 (6)0.056 (1)
C61.0964 (6)0.4193 (1)0.7081 (5)0.049 (1)
C71.0050 (5)0.3462 (1)0.7364 (5)0.041 (1)
C81.1100 (5)0.2570 (1)0.7495 (5)0.039 (1)
C90.9126 (5)0.2751 (1)0.7584 (4)0.035 (1)
C100.7575 (5)0.2494 (1)0.7712 (5)0.037 (1)
C110.7766 (5)0.2050 (1)0.7683 (5)0.036 (1)
C120.9594 (5)0.1882 (1)0.7502 (5)0.036 (1)
C130.9919 (5)0.1461 (1)0.7396 (5)0.042 (1)
C140.8375 (5)0.1190 (1)0.7512 (5)0.041 (1)
C150.6499 (6)0.1347 (1)0.7704 (5)0.045 (1)
C160.6213 (5)0.1766 (1)0.7782 (5)0.042 (1)
C171.0282 (6)0.0597 (1)0.7112 (7)0.060 (1)
H30.62170.45700.79500.088*
H40.66900.35430.78910.093*
H4a0.85520.50380.74680.089*
H51.15370.48060.68930.084*
H61.21670.40990.68560.074*
H71.12970.33800.71840.061*
H100.63490.26090.78230.055*
H131.11560.13600.72480.063*
H150.54510.11640.77770.068*
H160.49610.18660.79030.064*
H17a1.03320.07240.59110.090*
H17b1.00810.03010.69040.090*
H17c1.16440.06520.82990.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.029 (1)0.044 (1)0.057 (1)0.005 (1)0.022 (1)0.001 (1)
O20.036 (1)0.055 (2)0.088 (2)0.002 (1)0.035 (1)0.005 (1)
O30.053 (2)0.043 (1)0.070 (2)0.002 (1)0.026 (1)0.002 (1)
O40.060 (2)0.050 (2)0.094 (2)0.008 (1)0.051 (2)0.008 (2)
N10.033 (1)0.042 (2)0.037 (2)0.006 (1)0.014 (1)0.000 (1)
C10.038 (2)0.046 (2)0.032 (2)0.001 (1)0.011 (1)0.001 (1)
C20.048 (2)0.045 (2)0.049 (2)0.001 (2)0.025 (2)0.001 (2)
C30.067 (3)0.050 (2)0.070 (3)0.011 (2)0.039 (2)0.001 (2)
C40.071 (3)0.037 (2)0.068 (3)0.003 (2)0.028 (2)0.002 (2)
C50.053 (2)0.048 (2)0.056 (2)0.011 (2)0.014 (2)0.003 (2)
C60.041 (2)0.053 (2)0.049 (2)0.003 (2)0.014 (2)0.000 (2)
C70.031 (2)0.051 (2)0.040 (2)0.008 (2)0.014 (1)0.002 (1)
C80.028 (2)0.048 (2)0.038 (2)0.004 (1)0.013 (1)0.000 (1)
C90.029 (2)0.044 (2)0.028 (2)0.008 (1)0.009 (1)0.001 (1)
C100.030 (2)0.046 (2)0.036 (2)0.005 (1)0.016 (1)0.003 (1)
C110.026 (1)0.051 (2)0.031 (2)0.005 (1)0.012 (1)0.003 (1)
C120.025 (1)0.048 (2)0.034 (2)0.001 (1)0.011 (1)0.000 (1)
C130.032 (2)0.049 (2)0.045 (2)0.009 (2)0.016 (1)0.001 (2)
C140.039 (2)0.046 (2)0.035 (2)0.002 (2)0.011 (1)0.003 (1)
C150.038 (2)0.054 (2)0.045 (2)0.004 (2)0.019 (2)0.004 (2)
C160.032 (2)0.054 (2)0.045 (2)0.002 (2)0.020 (1)0.004 (2)
C170.053 (2)0.048 (2)0.075 (3)0.009 (2)0.022 (2)0.010 (2)
Geometric parameters (Å, º) top
O1—C121.375 (4)C11—C161.401 (4)
O1—C81.374 (4)C12—C131.373 (5)
O2—C81.201 (4)C13—C141.373 (5)
O3—C141.354 (4)C14—C151.406 (5)
O3—C171.420 (4)C15—C161.357 (5)
O4—C21.348 (4)O4—H40.8200
N1—C71.292 (4)C3—H30.9300
N1—C91.390 (4)C4—H4a0.9300
C1—C61.395 (5)C5—H50.9300
C1—C21.403 (5)C6—H60.9300
C1—C71.438 (5)C7—H70.9300
C2—C31.375 (5)C10—H100.9300
C3—C41.368 (6)C13—H130.9300
C4—C51.381 (6)C15—H150.9300
C5—C61.375 (5)C16—H160.9300
C8—C91.462 (4)C17—H17a0.9600
C9—C101.355 (4)C17—H17b0.9600
C10—C111.426 (4)C17—H17c0.9600
C11—C121.385 (4)
C12—O1—C8123.3 (2)O3—C14—C15115.2 (3)
C14—O3—C17117.0 (3)C13—C14—C15120.0 (3)
C7—N1—C9124.9 (3)C16—C15—C14120.2 (3)
C6—C1—C2118.1 (3)C15—C16—C11121.2 (3)
C6—C1—C7119.2 (3)C2—O4—H4109.5
C2—C1—C7122.7 (3)C4—C3—H3119.4
O4—C2—C3119.0 (3)C2—C3—H3119.4
O4—C2—C1121.3 (3)C3—C4—H4a119.8
C3—C2—C1119.7 (3)C5—C4—H4a119.8
C4—C3—C2121.1 (4)C6—C5—H5120.4
C3—C4—C5120.4 (4)C4—C5—H5120.4
C6—C5—C4119.1 (4)C5—C6—H6119.2
C5—C6—C1121.6 (4)C1—C6—H6119.2
N1—C7—C1121.4 (3)N1—C7—H7119.3
O2—C8—O1116.1 (3)C1—C7—H7119.3
O2—C8—C9126.7 (3)C9—C10—H10119.0
O1—C8—C9117.1 (3)C11—C10—H10119.0
C10—C9—N1118.0 (3)C12—C13—H13120.8
C10—C9—C8119.1 (3)C14—C13—H13120.8
N1—C9—C8122.9 (3)C16—C15—H15119.9
C9—C10—C11122.0 (3)C14—C15—H15119.9
C12—C11—C16116.8 (3)C15—C16—H16119.4
C12—C11—C10118.3 (3)C11—C16—H16119.4
C16—C11—C10124.9 (3)O3—C17—H17a109.5
C13—C12—O1116.6 (3)O3—C17—H17b109.5
C13—C12—C11123.4 (3)H17a—C17—H17b109.5
O1—C12—C11120.0 (3)O3—C17—H17b109.5
C12—C13—C14118.4 (3)H17a—C17—H17c109.5
O3—C14—C13124.8 (3)H17b—C17—H17c109.5
C6—C1—C2—O4179.6 (3)N1—C9—C10—C11178.8 (3)
C7—C1—C2—O40.3 (5)C8—C9—C10—C112.5 (4)
C6—C1—C2—C30.5 (5)C9—C10—C11—C120.5 (4)
C7—C1—C2—C3179.5 (3)C9—C10—C11—C16179.1 (3)
O4—C2—C3—C4180.0 (4)C8—O1—C12—C13179.8 (3)
C1—C2—C3—C40.1 (6)C8—O1—C12—C110.1 (4)
C2—C3—C4—C50.4 (7)C16—C11—C12—C130.7 (5)
C3—C4—C5—C60.5 (6)C10—C11—C12—C13178.0 (3)
C4—C5—C6—C10.1 (6)C16—C11—C12—O1179.5 (3)
C2—C1—C6—C50.4 (5)C10—C11—C12—O11.8 (4)
C7—C1—C6—C5179.6 (3)O1—C12—C13—C14179.0 (3)
C9—N1—C7—C1179.9 (3)C11—C12—C13—C141.2 (5)
C6—C1—C7—N1178.1 (3)C17—O3—C14—C133.5 (5)
C2—C1—C7—N11.9 (5)C17—O3—C14—C15176.0 (3)
C12—O1—C8—O2176.7 (3)C12—C13—C14—O3179.6 (3)
C12—O1—C8—C93.0 (4)C12—C13—C14—C150.9 (5)
C7—N1—C9—C10176.2 (3)O3—C14—C15—C16179.8 (3)
C7—N1—C9—C85.2 (5)C13—C14—C15—C160.2 (5)
O2—C8—C9—C10175.5 (3)C14—C15—C16—C110.3 (5)
O1—C8—C9—C104.1 (4)C12—C11—C16—C150.1 (5)
O2—C8—C9—N13.1 (5)C10—C11—C16—C15178.7 (3)
O1—C8—C9—N1177.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···N10.821.892.620 (3)147
C16—H16···O1i0.932.543.455 (4)168
C10—H10···O2i0.932.413.318 (4)165
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC17H13NO4
Mr295.28
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)6.660 (1), 31.984 (8), 7.123 (2)
β (°) 114.93 (2)
V3)1375.9 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.60 × 0.40 × 0.14
Data collection
DiffractometerSiemens P4 four-circle
diffractometer
Absorption correctionEmpirical (using intensity measurements)
via ψ scan (North et al., 1968)
Tmin, Tmax0.875, 0.966
No. of measured, independent and
observed [I > 2σ(I)] reflections
3194, 2416, 1449
Rint0.027
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.172, 1.05
No. of reflections2416
No. of parameters202
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.24

Computer programs: XSCANS (Siemens, 1998), XSCANS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.

Selected geometric parameters (Å, º) top
O1—C121.375 (4)C3—C41.368 (6)
O1—C81.374 (4)C4—C51.381 (6)
O2—C81.201 (4)C5—C61.375 (5)
O3—C141.354 (4)C8—C91.462 (4)
O3—C171.420 (4)C9—C101.355 (4)
O4—C21.348 (4)C10—C111.426 (4)
N1—C71.292 (4)C11—C121.385 (4)
N1—C91.390 (4)C11—C161.401 (4)
C1—C61.395 (5)C12—C131.373 (5)
C1—C21.403 (5)C13—C141.373 (5)
C1—C71.438 (5)C14—C151.406 (5)
C2—C31.375 (5)C15—C161.357 (5)
C12—O1—C8123.3 (2)C10—C9—N1118.0 (3)
C14—O3—C17117.0 (3)C10—C9—C8119.1 (3)
C7—N1—C9124.9 (3)N1—C9—C8122.9 (3)
C6—C1—C2118.1 (3)C9—C10—C11122.0 (3)
C6—C1—C7119.2 (3)C12—C11—C16116.8 (3)
C2—C1—C7122.7 (3)C12—C11—C10118.3 (3)
O4—C2—C3119.0 (3)C16—C11—C10124.9 (3)
O4—C2—C1121.3 (3)C13—C12—O1116.6 (3)
C3—C2—C1119.7 (3)C13—C12—C11123.4 (3)
C4—C3—C2121.1 (4)O1—C12—C11120.0 (3)
C3—C4—C5120.4 (4)C12—C13—C14118.4 (3)
C6—C5—C4119.1 (4)O3—C14—C13124.8 (3)
C5—C6—C1121.6 (4)O3—C14—C15115.2 (3)
N1—C7—C1121.4 (3)C13—C14—C15120.0 (3)
O2—C8—O1116.1 (3)C16—C15—C14120.2 (3)
O2—C8—C9126.7 (3)C15—C16—C11121.2 (3)
O1—C8—C9117.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···N10.821.892.620 (3)147.0
C16—H16···O1i0.932.543.455 (4)168.0
C10—H10···O2i0.932.413.318 (4)164.6
Symmetry code: (i) x1, y, z.
 

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