3-Acetyl-7-(diethyl­amino)coumarin

The title compound, C₁₅H₁₇NO₃, is nearly planar with a dihedral angle of 1.55 (10)° between the lactone and benzene rings. The mol­ecules form chains through weak C—H...O hydrogen bonds and the chains are dimerized by type-II carbon­yl–carbonyl inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.051
• wR factor = 0.199
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

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Computing details

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: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Mercury (Bruno et al., 2002) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-Acetyl-7-(diethylamino)coumarin

Crystal data

C15H17NO3	F(000) = 1104
Mr = 259.3	Dx = 1.266 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 17.269 (2) Å	θ = 7.3–13.9°
b = 7.5203 (8) Å	µ = 0.09 mm^−1
c = 22.0868 (10) Å	T = 297 K
β = 108.524 (7)°	Prism, red
V = 2719.8 (5) Å^3	0.50 × 0.50 × 0.27 mm
Z = 8

Data collection

Enraf–Nonius CAD-4 diffractometer	θmax = 27.5°, θmin = 1.9°
non–profiled ω/2θ scans	h = 0→22
3217 measured reflections	k = 0→9
3118 independent reflections	l = −28→27
1984 reflections with I > 2σ(I)	3 standard reflections every 120 min
Rint = 0.018	intensity decay: 3%

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.051	w = 1/[σ^2(Fo^2) + (0.1085P)^2 + 0.3073P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.199	(Δ/σ)max < 0.001
S = 1.18	Δρmax = 0.32 e Å^−3
3118 reflections	Δρmin = −0.22 e Å^−3
173 parameters

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C2	0.24645 (12)	−0.0212 (3)	0.50400 (10)	0.0411 (4)
C3	0.24620 (12)	0.0570 (3)	0.44395 (9)	0.0406 (4)
C4	0.31476 (12)	0.1420 (3)	0.44062 (9)	0.0417 (5)
H4	0.3136	0.1941	0.4022	0.05*
C5	0.46020 (12)	0.2355 (3)	0.49209 (10)	0.0440 (5)
H5	0.462	0.2898	0.4547	0.053*
C6	0.52837 (12)	0.2375 (3)	0.54421 (10)	0.0435 (5)
H6	0.5755	0.2927	0.5419	0.052*
C7	0.52814 (12)	0.1553 (3)	0.60256 (9)	0.0393 (4)
C8	0.45510 (12)	0.0734 (3)	0.60396 (9)	0.0413 (5)
H8	0.4528	0.0189	0.6411	0.05*
C9	0.38745 (11)	0.0744 (2)	0.55036 (9)	0.0367 (4)
C10	0.38671 (12)	0.1539 (2)	0.49277 (9)	0.0384 (4)
C12	0.17408 (13)	0.0451 (3)	0.38463 (10)	0.0496 (5)
C14	0.09845 (15)	−0.0521 (4)	0.38423 (13)	0.0640 (7)
H14A	0.0756	0.0028	0.414	0.096*
H14B	0.1117	−0.1738	0.3963	0.096*
H14C	0.0594	−0.0478	0.3421	0.096*
C16	0.67185 (12)	0.2468 (3)	0.65512 (11)	0.0498 (5)
H16A	0.6791	0.2333	0.6136	0.06*
H16B	0.718	0.191	0.6865	0.06*
C17	0.67079 (17)	0.4430 (3)	0.67040 (13)	0.0681 (7)
H17A	0.7212	0.4965	0.6703	0.102*
H17B	0.6644	0.4571	0.7117	0.102*
H17C	0.6261	0.4995	0.6388	0.102*
C18	0.59596 (15)	0.0824 (3)	0.71587 (10)	0.0565 (6)
H18A	0.5433	0.1062	0.7213	0.068*
H18B	0.6374	0.1419	0.7502	0.068*
C19	0.6117 (2)	−0.1152 (4)	0.72090 (14)	0.0796 (9)
H19A	0.6102	−0.1569	0.7616	0.119*
H19B	0.6644	−0.1394	0.7168	0.119*
H19C	0.5704	−0.1751	0.6875	0.119*
N15	0.59663 (10)	0.1560 (2)	0.65482 (8)	0.0468 (4)
O1	0.31849 (8)	−0.00729 (18)	0.55500 (6)	0.0431 (4)
O11	0.19136 (9)	−0.0979 (2)	0.51581 (8)	0.0592 (5)
O13	0.17832 (11)	0.1158 (3)	0.33609 (8)	0.0806 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0404 (10)	0.0390 (10)	0.0475 (10)	0.0018 (8)	0.0190 (8)	0.0020 (8)
C3	0.0414 (10)	0.0375 (10)	0.0449 (10)	0.0033 (8)	0.0167 (8)	0.0008 (8)
C4	0.0468 (11)	0.0417 (11)	0.0404 (9)	0.0029 (9)	0.0190 (8)	0.0061 (8)
C5	0.0470 (11)	0.0455 (11)	0.0457 (10)	−0.0031 (9)	0.0232 (9)	0.0078 (9)
C6	0.0400 (10)	0.0449 (11)	0.0503 (11)	−0.0055 (9)	0.0211 (9)	0.0023 (9)
C7	0.0403 (10)	0.0366 (10)	0.0437 (10)	−0.0001 (8)	0.0173 (8)	−0.0015 (8)
C8	0.0447 (11)	0.0427 (11)	0.0406 (9)	−0.0029 (9)	0.0192 (8)	0.0033 (8)
C9	0.0393 (10)	0.0328 (9)	0.0437 (10)	−0.0003 (8)	0.0214 (8)	0.0020 (8)
C10	0.0400 (10)	0.0368 (10)	0.0424 (9)	0.0025 (8)	0.0187 (8)	0.0043 (8)
C12	0.0477 (12)	0.0486 (12)	0.0511 (12)	0.0044 (10)	0.0139 (9)	−0.0006 (9)
C14	0.0522 (13)	0.0619 (15)	0.0683 (15)	−0.0081 (12)	0.0055 (11)	−0.0002 (12)
C16	0.0397 (11)	0.0545 (13)	0.0530 (11)	−0.0063 (10)	0.0115 (9)	0.0000 (10)
C17	0.0761 (17)	0.0526 (14)	0.0675 (15)	−0.0144 (12)	0.0113 (13)	−0.0020 (11)
C18	0.0560 (13)	0.0713 (15)	0.0405 (10)	−0.0070 (11)	0.0131 (9)	−0.0009 (10)
C19	0.087 (2)	0.0729 (18)	0.0666 (16)	−0.0062 (16)	0.0075 (14)	0.0216 (14)
N15	0.0435 (9)	0.0510 (10)	0.0448 (9)	−0.0058 (8)	0.0127 (7)	0.0002 (8)
O1	0.0400 (7)	0.0485 (8)	0.0442 (7)	−0.0060 (6)	0.0182 (6)	0.0069 (6)
O11	0.0469 (9)	0.0717 (11)	0.0638 (10)	−0.0131 (8)	0.0244 (7)	0.0105 (8)
O13	0.0672 (12)	0.1156 (16)	0.0515 (10)	−0.0086 (11)	0.0081 (8)	0.0209 (10)

Geometric parameters (Å, º)

C2—O11	1.210 (2)	C12—C14	1.494 (3)
C2—O1	1.392 (2)	C14—H14A	0.96
C2—C3	1.450 (3)	C14—H14B	0.96
C2—O11^i	3.139 (3)	C14—H14C	0.96
C3—C4	1.368 (3)	C16—N15	1.466 (3)
C3—C12	1.496 (3)	C16—C17	1.515 (3)
C4—C10	1.403 (3)	C16—H16A	0.97
C4—H4	0.93	C16—H16B	0.97
C5—C6	1.360 (3)	C17—H17A	0.96
C5—C10	1.414 (3)	C17—H17B	0.96
C5—H5	0.93	C17—H17C	0.96
C6—C7	1.431 (3)	C18—N15	1.461 (3)
C6—H6	0.93	C18—C19	1.508 (4)
C7—N15	1.365 (2)	C18—H18A	0.97
C7—C8	1.413 (3)	C18—H18B	0.97
C8—C9	1.374 (3)	C19—H19A	0.96
C8—H8	0.93	C19—H19B	0.96
C9—O1	1.373 (2)	C19—H19C	0.96
C9—C10	1.402 (3)	O11—C2^i	3.139 (3)
C12—O13	1.220 (3)
O11—C2—O1	115.04 (18)	C12—C14—H14B	109.5
O11—C2—C3	128.1 (2)	H14A—C14—H14B	109.5
O1—C2—C3	116.88 (17)	C12—C14—H14C	109.5
O11—C2—O11^i	85.53 (13)	H14A—C14—H14C	109.5
O1—C2—O11^i	85.63 (11)	H14B—C14—H14C	109.5
C3—C2—O11^i	98.30 (12)	N15—C16—C17	112.4 (2)
C4—C3—C2	119.19 (18)	N15—C16—H16A	109.1
C4—C3—C12	118.36 (18)	C17—C16—H16A	109.1
C2—C3—C12	122.44 (18)	N15—C16—H16B	109.1
C3—C4—C10	122.78 (18)	C17—C16—H16B	109.1
C3—C4—H4	118.6	H16A—C16—H16B	107.9
C10—C4—H4	118.6	C16—C17—H17A	109.5
C6—C5—C10	122.28 (18)	C16—C17—H17B	109.5
C6—C5—H5	118.9	H17A—C17—H17B	109.5
C10—C5—H5	118.9	C16—C17—H17C	109.5
C5—C6—C7	120.55 (18)	H17A—C17—H17C	109.5
C5—C6—H6	119.7	H17B—C17—H17C	109.5
C7—C6—H6	119.7	N15—C18—C19	112.8 (2)
N15—C7—C8	121.54 (17)	N15—C18—H18A	109
N15—C7—C6	120.69 (17)	C19—C18—H18A	109
C8—C7—C6	117.78 (17)	N15—C18—H18B	109
C9—C8—C7	119.98 (17)	C19—C18—H18B	109
C9—C8—H8	120	H18A—C18—H18B	107.8
C7—C8—H8	120	C18—C19—H19A	109.5
O1—C9—C8	116.98 (16)	C18—C19—H19B	109.5
O1—C9—C10	120.05 (17)	H19A—C19—H19B	109.5
C8—C9—C10	122.97 (17)	C18—C19—H19C	109.5
C9—C10—C4	117.91 (17)	H19A—C19—H19C	109.5
C9—C10—C5	116.44 (17)	H19B—C19—H19C	109.5
C4—C10—C5	125.62 (17)	C7—N15—C18	121.34 (17)
O13—C12—C14	120.3 (2)	C7—N15—C16	122.29 (17)
O13—C12—C3	118.5 (2)	C18—N15—C16	116.05 (17)
C14—C12—C3	121.2 (2)	C9—O1—C2	123.15 (15)
C12—C14—H14A	109.5	C2—O11—C2^i	94.47 (13)
O11—C2—C3—C4	178.6 (2)	C6—C5—C10—C4	−178.11 (19)
O1—C2—C3—C4	−1.2 (3)	C4—C3—C12—O13	−2.0 (3)
O11^i—C2—C3—C4	−90.54 (18)	C2—C3—C12—O13	179.3 (2)
O11—C2—C3—C12	−2.7 (3)	C4—C3—C12—C14	177.5 (2)
O1—C2—C3—C12	177.38 (17)	C2—C3—C12—C14	−1.1 (3)
O11^i—C2—C3—C12	88.09 (19)	C8—C7—N15—C18	−4.1 (3)
C2—C3—C4—C10	1.4 (3)	C6—C7—N15—C18	176.2 (2)
C12—C3—C4—C10	−177.24 (18)	C8—C7—N15—C16	−177.30 (18)
C10—C5—C6—C7	0.1 (3)	C6—C7—N15—C16	3.0 (3)
C5—C6—C7—N15	179.57 (19)	C19—C18—N15—C7	85.9 (3)
C5—C6—C7—C8	−0.2 (3)	C19—C18—N15—C16	−100.5 (3)
N15—C7—C8—C9	−179.64 (18)	C17—C16—N15—C7	84.1 (2)
C6—C7—C8—C9	0.1 (3)	C17—C16—N15—C18	−89.4 (2)
C7—C8—C9—O1	−179.93 (17)	C8—C9—O1—C2	−177.95 (17)
C7—C8—C9—C10	0.1 (3)	C10—C9—O1—C2	2.0 (3)
O1—C9—C10—C4	−1.8 (3)	O11—C2—O1—C9	179.62 (17)
C8—C9—C10—C4	178.17 (18)	C3—C2—O1—C9	−0.5 (3)
O1—C9—C10—C5	179.83 (17)	O11^i—C2—O1—C9	96.62 (16)
C8—C9—C10—C5	−0.2 (3)	O1—C2—O11—C2^i	−83.06 (16)
C3—C4—C10—C9	0.1 (3)	C3—C2—O11—C2^i	97.0 (2)
C3—C4—C10—C5	178.28 (19)	O11^i—C2—O11—C2^i	0
C6—C5—C10—C9	0.1 (3)

Symmetry code: (i) −x+1/2, −y−1/2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O11^ii	0.93	2.40	3.312 (2)	168

Symmetry code: (ii) x+1/2, y+1/2, z.