Menthyl 2-oxo-2H-chromene-3-carboxyl-ate.

The title compound, C(20)H(24)O(4), was synthesized from the reaction of 2-oxo-2H-chromene-3-acyl chloride and menthol. The mean plane of the ester group and that of the four essentially planar (maximum deviation 0.0112 Å) C atoms of the chair-form cyclo-hexyl ring form dihedral angles of 43.8 (3) ° and 81.8 (1)°, respectively, with the mean plane of the coumarin ring system. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds connect the mol-ecules into a two-dimensional network.

Related literature

For the applications of coumarin compounds, see: Yu et al. (2003 ▶, 2007 ▶).

Experimental

Crystal data

C20H24O4

M = 328.39

Orthorhombic,

a = 11.080 (2) Å

b = 12.408 (3) Å

c = 13.532 (3) Å

V = 1860.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 291 K

0.18 × 0.18 × 0.17 mm

Data collection

Rigaku R-AXIS-IV diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi,1995 ▶) T min = 0.986, T max = 0.986

5812 measured reflections

1943 independent reflections

1654 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.138

S = 1.09

1943 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

Data collection: R-AXIS (Rigaku, 1997 ▶); cell refinement: R-AXIS data reduction: R-AXIS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: TEXSAN (Molecular Structure Corporation & Rigaku (2000 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: TEXSAN.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809035995/lh2883sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035995/lh2883Isup2.hkl

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

C20H24O4	F(000) = 704
Mr = 328.39	Dx = 1.173 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 489 reflections
a = 11.080 (2) Å	θ = 2.2–25.5°
b = 12.408 (3) Å	µ = 0.08 mm−1
c = 13.532 (3) Å	T = 291 K
V = 1860.3 (6) Å3	Prism, colorless
Z = 4	0.18 × 0.18 × 0.17 mm

Rigaku R-AXIS-IV diffractometer	1943 independent reflections
Radiation source: fine-focus sealed tube	1654 reflections with I > 2σ(I)
graphite	Rint = 0.063
Detector resolution: 0 pixels mm-1	θmax = 25.5°, θmin = 2.2°
Oscillation frames scans	h = −13→13
Absorption correction: multi-scan (ABSCOR; Higashi,1995)	k = 0→15
Tmin = 0.986, Tmax = 0.986	l = −16→16
5812 measured reflections

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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.0742P)2 + 0.172P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
1943 reflections	Δρmax = 0.15 e Å−3
218 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (5)

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
O1	1.1789 (2)	1.01848 (18)	0.10921 (18)	0.0682 (7)
O2	1.0992 (3)	1.1284 (2)	0.2180 (2)	0.0863 (8)
O3	0.9734 (2)	1.0101 (2)	0.37733 (18)	0.0852 (8)
O4	0.83141 (18)	0.92908 (18)	0.28562 (15)	0.0591 (6)
C1	1.1825 (3)	0.9219 (3)	0.0601 (2)	0.0593 (8)
C2	1.2617 (3)	0.9135 (3)	−0.0176 (3)	0.0814 (11)
H2A	1.3124	0.9706	−0.0337	0.098*
C3	1.2651 (4)	0.8204 (4)	−0.0710 (3)	0.0929 (13)
H3A	1.3179	0.8145	−0.1242	0.111*
C4	1.1909 (5)	0.7341 (4)	−0.0468 (3)	0.0931 (14)
H4A	1.1947	0.6707	−0.0833	0.112*
C5	1.1114 (4)	0.7426 (3)	0.0315 (3)	0.0760 (10)
H5A	1.0618	0.6849	0.0478	0.091*
C6	1.1055 (3)	0.8379 (2)	0.0861 (2)	0.0545 (7)
C7	1.0247 (3)	0.8555 (2)	0.1674 (2)	0.0547 (7)
H7A	0.9738	0.8000	0.1873	0.066*
C8	1.0208 (3)	0.9499 (2)	0.2151 (2)	0.0508 (7)
C9	1.0994 (3)	1.0387 (3)	0.1849 (2)	0.0611 (8)
C10	0.9412 (3)	0.9684 (3)	0.3017 (2)	0.0571 (8)
C11	0.7426 (3)	0.9362 (2)	0.3663 (2)	0.0565 (8)
H11A	0.7545	1.0039	0.4022	0.068*
C12	0.6189 (3)	0.9375 (3)	0.3173 (2)	0.0656 (9)
H12A	0.6123	0.8708	0.2789	0.079*
C13	0.5222 (3)	0.9316 (3)	0.3989 (3)	0.0834 (11)
H13A	0.5242	0.9976	0.4373	0.100*
H13B	0.4431	0.9261	0.3685	0.100*
C14	0.5413 (4)	0.8365 (3)	0.4669 (3)	0.0853 (12)
H14A	0.4794	0.8369	0.5175	0.102*
H14B	0.5327	0.7704	0.4293	0.102*
C15	0.6634 (4)	0.8376 (3)	0.5156 (3)	0.0755 (10)
H15A	0.6690	0.9033	0.5555	0.091*
C16	0.7619 (3)	0.8429 (3)	0.4359 (3)	0.0668 (9)
H16A	0.8401	0.8502	0.4675	0.080*
H16B	0.7620	0.7761	0.3986	0.080*
C17	0.5998 (4)	1.0313 (4)	0.2444 (3)	0.0888 (12)
H17A	0.6684	1.0305	0.1987	0.107*
C18	0.4854 (5)	1.0146 (6)	0.1819 (4)	0.142 (2)
H18A	0.4882	0.9450	0.1511	0.213*
H18B	0.4811	1.0694	0.1320	0.213*
H18C	0.4156	1.0190	0.2237	0.213*
C19	0.5982 (5)	1.1416 (4)	0.2928 (4)	0.1272 (19)
H19A	0.5862	1.1959	0.2432	0.191*
H19B	0.6737	1.1539	0.3257	0.191*
H19C	0.5336	1.1447	0.3400	0.191*
C20	0.6831 (6)	0.7415 (4)	0.5839 (4)	0.1226 (19)
H20A	0.6209	0.7401	0.6332	0.184*
H20B	0.7604	0.7479	0.6154	0.184*
H20C	0.6805	0.6761	0.5461	0.184*

	U11	U22	U33	U12	U13	U23
O1	0.0560 (13)	0.0657 (14)	0.0828 (15)	−0.0095 (11)	0.0147 (13)	0.0056 (12)
O2	0.103 (2)	0.0614 (14)	0.0946 (18)	−0.0128 (13)	0.0082 (17)	−0.0075 (14)
O3	0.0623 (15)	0.122 (2)	0.0708 (15)	−0.0146 (15)	0.0000 (13)	−0.0310 (15)
O4	0.0420 (11)	0.0798 (14)	0.0556 (12)	−0.0051 (10)	0.0088 (10)	−0.0100 (11)
C1	0.0418 (16)	0.073 (2)	0.0635 (19)	0.0067 (15)	0.0045 (15)	0.0122 (17)
C2	0.060 (2)	0.097 (3)	0.087 (3)	0.012 (2)	0.026 (2)	0.012 (2)
C3	0.070 (2)	0.125 (3)	0.084 (3)	0.028 (3)	0.032 (2)	0.011 (3)
C4	0.095 (3)	0.103 (3)	0.081 (3)	0.029 (3)	0.011 (3)	−0.019 (2)
C5	0.083 (3)	0.070 (2)	0.075 (2)	0.008 (2)	0.010 (2)	−0.0050 (19)
C6	0.0466 (16)	0.0606 (17)	0.0564 (17)	0.0036 (14)	0.0032 (15)	0.0057 (15)
C7	0.0450 (16)	0.0618 (17)	0.0572 (16)	−0.0066 (14)	−0.0003 (15)	0.0057 (14)
C8	0.0407 (15)	0.0583 (17)	0.0533 (15)	−0.0003 (13)	−0.0028 (14)	0.0008 (14)
C9	0.0510 (18)	0.064 (2)	0.069 (2)	−0.0023 (15)	−0.0058 (16)	0.0037 (17)
C10	0.0445 (17)	0.0688 (19)	0.0579 (18)	0.0017 (15)	−0.0032 (15)	−0.0072 (16)
C11	0.0494 (17)	0.0660 (18)	0.0541 (17)	0.0028 (14)	0.0092 (15)	−0.0053 (15)
C12	0.0461 (17)	0.083 (2)	0.068 (2)	0.0034 (17)	0.0045 (16)	−0.0060 (18)
C13	0.0520 (19)	0.105 (3)	0.093 (3)	0.001 (2)	0.016 (2)	−0.008 (2)
C14	0.075 (3)	0.095 (3)	0.086 (3)	−0.019 (2)	0.036 (2)	−0.015 (2)
C15	0.082 (3)	0.079 (2)	0.066 (2)	−0.004 (2)	0.020 (2)	−0.0009 (19)
C16	0.063 (2)	0.074 (2)	0.0637 (19)	0.0068 (17)	0.0091 (17)	0.0003 (18)
C17	0.062 (2)	0.113 (3)	0.091 (3)	0.016 (2)	−0.002 (2)	0.019 (2)
C18	0.107 (4)	0.188 (6)	0.130 (4)	0.018 (4)	−0.044 (4)	0.027 (4)
C19	0.134 (4)	0.099 (3)	0.149 (4)	0.025 (3)	−0.001 (4)	0.023 (4)
C20	0.148 (5)	0.121 (4)	0.099 (3)	0.001 (4)	0.038 (4)	0.033 (3)

O1—C1	1.370 (4)	C12—C13	1.540 (5)
O1—C9	1.374 (4)	C12—H12A	0.9800
O2—C9	1.199 (4)	C13—C14	1.512 (6)
O3—C10	1.201 (4)	C13—H13A	0.9700
O4—C10	1.328 (4)	C13—H13B	0.9700
O4—C11	1.472 (4)	C14—C15	1.504 (6)
C1—C2	1.374 (5)	C14—H14A	0.9700
C1—C6	1.392 (4)	C14—H14B	0.9700
C2—C3	1.363 (6)	C15—C20	1.525 (6)
C2—H2A	0.9300	C15—C16	1.535 (5)
C3—C4	1.389 (6)	C15—H15A	0.9800
C3—H3A	0.9300	C16—H16A	0.9700
C4—C5	1.382 (5)	C16—H16B	0.9700
C4—H4A	0.9300	C17—C19	1.517 (7)
C5—C6	1.396 (5)	C17—C18	1.537 (7)
C5—H5A	0.9300	C17—H17A	0.9800
C6—C7	1.434 (4)	C18—H18A	0.9600
C7—C8	1.338 (4)	C18—H18B	0.9600
C7—H7A	0.9300	C18—H18C	0.9600
C8—C9	1.463 (4)	C19—H19A	0.9600
C8—C10	1.485 (4)	C19—H19B	0.9600
C11—C16	1.508 (5)	C19—H19C	0.9600
C11—C12	1.522 (4)	C20—H20A	0.9600
C11—H11A	0.9800	C20—H20B	0.9600
C12—C17	1.539 (5)	C20—H20C	0.9600
C1—O1—C9	122.7 (2)	C12—C13—H13A	109.2
C10—O4—C11	117.9 (2)	C14—C13—H13B	109.2
O1—C1—C2	117.1 (3)	C12—C13—H13B	109.2
O1—C1—C6	120.9 (3)	H13A—C13—H13B	107.9
C2—C1—C6	121.9 (3)	C15—C14—C13	112.6 (3)
C3—C2—C1	119.2 (4)	C15—C14—H14A	109.1
C3—C2—H2A	120.4	C13—C14—H14A	109.1
C1—C2—H2A	120.4	C15—C14—H14B	109.1
C2—C3—C4	120.8 (4)	C13—C14—H14B	109.1
C2—C3—H3A	119.6	H14A—C14—H14B	107.8
C4—C3—H3A	119.6	C14—C15—C20	112.8 (4)
C5—C4—C3	119.9 (4)	C14—C15—C16	109.4 (3)
C5—C4—H4A	120.1	C20—C15—C16	110.9 (4)
C3—C4—H4A	120.1	C14—C15—H15A	107.9
C4—C5—C6	120.1 (4)	C20—C15—H15A	107.9
C4—C5—H5A	120.0	C16—C15—H15A	107.9
C6—C5—H5A	120.0	C11—C16—C15	111.7 (3)
C1—C6—C5	118.1 (3)	C11—C16—H16A	109.3
C1—C6—C7	117.6 (3)	C15—C16—H16A	109.3
C5—C6—C7	124.3 (3)	C11—C16—H16B	109.3
C8—C7—C6	121.5 (3)	C15—C16—H16B	109.3
C8—C7—H7A	119.2	H16A—C16—H16B	107.9
C6—C7—H7A	119.2	C19—C17—C18	110.4 (4)
C7—C8—C9	120.4 (3)	C19—C17—C12	114.0 (4)
C7—C8—C10	122.4 (3)	C18—C17—C12	111.3 (4)
C9—C8—C10	117.2 (3)	C19—C17—H17A	106.9
O2—C9—O1	116.6 (3)	C18—C17—H17A	106.9
O2—C9—C8	126.4 (3)	C12—C17—H17A	106.9
O1—C9—C8	116.9 (3)	C17—C18—H18A	109.5
O3—C10—O4	124.8 (3)	C17—C18—H18B	109.5
O3—C10—C8	124.3 (3)	H18A—C18—H18B	109.5
O4—C10—C8	110.9 (3)	C17—C18—H18C	109.5
O4—C11—C16	108.8 (2)	H18A—C18—H18C	109.5
O4—C11—C12	106.2 (2)	H18B—C18—H18C	109.5
C16—C11—C12	114.1 (3)	C17—C19—H19A	109.5
O4—C11—H11A	109.2	C17—C19—H19B	109.5
C16—C11—H11A	109.2	H19A—C19—H19B	109.5
C12—C11—H11A	109.2	C17—C19—H19C	109.5
C11—C12—C17	114.3 (3)	H19A—C19—H19C	109.5
C11—C12—C13	108.3 (3)	H19B—C19—H19C	109.5
C17—C12—C13	113.6 (3)	C15—C20—H20A	109.5
C11—C12—H12A	106.7	C15—C20—H20B	109.5
C17—C12—H12A	106.7	H20A—C20—H20B	109.5
C13—C12—H12A	106.7	C15—C20—H20C	109.5
C14—C13—C12	112.1 (3)	H20A—C20—H20C	109.5
C14—C13—H13A	109.2	H20B—C20—H20C	109.5
C9—O1—C1—C2	176.7 (3)	C11—O4—C10—C8	177.2 (2)
C9—O1—C1—C6	−1.0 (4)	C7—C8—C10—O3	133.2 (4)
O1—C1—C2—C3	−177.6 (3)	C9—C8—C10—O3	−44.8 (5)
C6—C1—C2—C3	0.1 (5)	C7—C8—C10—O4	−44.5 (4)
C1—C2—C3—C4	−0.8 (6)	C9—C8—C10—O4	137.5 (3)
C2—C3—C4—C5	0.7 (7)	C10—O4—C11—C16	−83.0 (3)
C3—C4—C5—C6	0.1 (6)	C10—O4—C11—C12	153.7 (3)
O1—C1—C6—C5	178.3 (3)	O4—C11—C12—C17	−58.8 (4)
C2—C1—C6—C5	0.7 (5)	C16—C11—C12—C17	−178.7 (3)
O1—C1—C6—C7	−1.3 (4)	O4—C11—C12—C13	173.5 (3)
C2—C1—C6—C7	−178.9 (3)	C16—C11—C12—C13	53.6 (4)
C4—C5—C6—C1	−0.8 (5)	C11—C12—C13—C14	−53.9 (4)
C4—C5—C6—C7	178.8 (3)	C17—C12—C13—C14	178.0 (3)
C1—C6—C7—C8	1.6 (4)	C12—C13—C14—C15	57.7 (4)
C5—C6—C7—C8	−178.0 (3)	C13—C14—C15—C20	−179.8 (3)
C6—C7—C8—C9	0.3 (4)	C13—C14—C15—C16	−55.8 (4)
C6—C7—C8—C10	−177.6 (3)	O4—C11—C16—C15	−173.5 (3)
C1—O1—C9—O2	−175.3 (3)	C12—C11—C16—C15	−55.1 (4)
C1—O1—C9—C8	2.9 (4)	C14—C15—C16—C11	53.8 (4)
C7—C8—C9—O2	175.4 (3)	C20—C15—C16—C11	178.8 (4)
C10—C8—C9—O2	−6.6 (5)	C11—C12—C17—C19	−66.3 (5)
C7—C8—C9—O1	−2.5 (4)	C13—C12—C17—C19	58.5 (5)
C10—C8—C9—O1	175.5 (2)	C11—C12—C17—C18	167.9 (4)
C11—O4—C10—O3	−0.5 (5)	C13—C12—C17—C18	−67.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2i	0.93	2.43	3.288 (5)	154
C5—H5A···O3ii	0.93	2.42	3.276 (5)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O2i	0.93	2.43	3.288 (5)	154
C5—H5A⋯O3ii	0.93	2.42	3.276 (5)	152

Symmetry codes: (i) ; (ii) .