4-(3,4-Methyl­ene­dioxy­phenyl)-7,7-di­methyl-5-oxo-3,4,5,6,7,8-hexa­hydro­coumarin

Wu, H.; Shi, D.; Chen, J.; Wang, X.; Zhuang, Q.; Hu, H.

doi:10.1107/S1600536803016945

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4-(3,4-Methylenedioxyphenyl)-7,7-dimethyl-5-oxo-3,4,5,6,7,8-hexahydrocoumarin

H. Wu, D. Shi, J. Chen, X. Wang, Q. Zhuang and H. Hu

The title compound, C₁₈H₁₈O₅, was synthesized by the reaction of 3,4-methylenedioxybenzaldehyde, 5,5-dimethyl-1,3-cyclohexanedione and isopropylidene malonate in the presence of triethylbenzylammonium chloride in water. X-ray analysis reveals that the pyran ring and the fused six-membered ring adopt distorted boat conformations.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803016945/ww6104sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803016945/ww6104Isup2.hkl Contains datablock I

CCDC reference: 217032

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R factor = 0.038
wR factor = 0.101
Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C17    =       5.94 su
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ..           C3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Coumarin and coumarin derivatives are natural compounds and are important chemicals in the perfume, cosmetic and pharmaceutical industrial production (Soine, 1964). As part of our program aimed at developing new and environmental friendly methodologies for the preparation of fine chemicals (Shi et al., 2003). We performed the synthesis of coumarin derivatives through a three-component reaction employing water as the reaction medium.

We report here the crystal structure of 4-(3,4-methylenedioxyphenyl)-7,7-dimethyl-5-oxo-3,4,5,6,7,8-hexahydrocoumarin, (I), synthesized by the reaction of 3,4-methylenedioxylbenzaldehyde, 5,5-dimethyl-1,3-cyclohexandione and isopropylidene malonate in the presence of triethylbenzylammonium chloride in water.

In (I), atoms O1, C1, C6, C7, C8 and C9 form a pyran ring, and the O1—C1, O1—C9 and C1—C6 bond lengths of 1.386 (2), 1.381 (2) and 1.341 (2) Å, respectively, are slightly longer than those of 2-amino-7,7-dimethyl-4-phenyl-5-oxo-5,6,7,8-tetrahydro- 4H-chromene-3-carbonitrile (Gao et al., 2001). In addition, this pyran ring adopts a distorted boat conformation; atoms O1, C1, C6 and C7 are on one plane, while atoms C8 and C9 deviate from the plane by 0.77 and 0.28 Å, respectively. X-Ray analysis reveals that the six-membered C1–C6 ring adopts a distorted boat conformation which is different from the envelope conformation (Tu et al., 2001).

Experimental top

The title compound, (I), was prepared by the reaction of 3,4-methylenedioxylbenzaldehyde, 5,5-dimethyl-1,3-cyclohexandione and isopropylidene malonate in the presence of triethylbenzylammonium chloride in water at 348 K for 6 h (m.p. 427–429 K). The single crystals suitable for X-ray diffraction were obtained by slow evaporation of ethanol solution.

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The molecular structure drawing for (I), showing 50% probability of displacement ellipsoids and the atom-numbering scheme.

4-(3,4-methylenedioxyphenyl)-7,7-dimethyl-5-oxo-3,4,5,6,7,8-hexahydrocoumarin top

Crystal data top

C₁₈H₁₈O₅	Z = 2
M_r = 314.32	F(000) = 332
Triclinic, P1	D_x = 1.347 Mg m⁻³
Hall symbol: -P 1	Melting point = 427–429 K
a = 6.963 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.957 (2) Å	Cell parameters from 28 reflections
c = 13.594 (3) Å	θ = 3.3–17.0°
α = 90.16 (2)°	µ = 0.10 mm⁻¹
β = 103.11 (2)°	T = 296 K
γ = 109.60 (2)°	Block, colorless
V = 775.0 (3) Å³	0.54 × 0.48 × 0.24 mm

Data collection top

Siemens P4 diffractometer	R_int = 0.014
Radiation source: normal-focus sealed tube	θ_max = 25.0°, θ_min = 1.5°
Graphite monochromator	h = 0→8
ω scans	k = −10→9
3072 measured reflections	l = −16→15
2731 independent reflections	3 standard reflections every 97 reflections
1937 reflections with I > 2σ(I)	intensity decay: 6.0%

Refinement top

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)] = 0.038	H-atom parameters constrained
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0542P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
2731 reflections	Δρ_max = 0.17 e Å⁻³
211 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.041 (5)

Crystal data top

C₁₈H₁₈O₅	γ = 109.60 (2)°
M_r = 314.32	V = 775.0 (3) Å³
Triclinic, P1	Z = 2
a = 6.963 (1) Å	Mo Kα radiation
b = 8.957 (2) Å	µ = 0.10 mm⁻¹
c = 13.594 (3) Å	T = 296 K
α = 90.16 (2)°	0.54 × 0.48 × 0.24 mm
β = 103.11 (2)°

Data collection top

Siemens P4 diffractometer	R_int = 0.014
3072 measured reflections	3 standard reflections every 97 reflections
2731 independent reflections	intensity decay: 6.0%
1937 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	Δρ_max = 0.17 e Å⁻³
2731 reflections	Δρ_min = −0.16 e Å⁻³
211 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.13514 (18)	0.54308 (14)	0.13021 (8)	0.0545 (3)
O2	0.85495 (19)	1.14456 (14)	0.50051 (9)	0.0620 (4)
O3	1.01742 (19)	1.20478 (14)	0.36817 (10)	0.0675 (4)
O4	0.5954 (2)	0.40580 (17)	0.39569 (9)	0.0783 (4)
O5	0.0147 (2)	0.73684 (16)	0.14565 (10)	0.0705 (4)
C1	0.2442 (2)	0.44709 (18)	0.17532 (12)	0.0440 (4)
C2	0.2199 (3)	0.3133 (2)	0.10370 (13)	0.0556 (5)
H2A	0.2192	0.3505	0.0367	0.067*
H2B	0.0853	0.2307	0.0999	0.067*
C3	0.3937 (3)	0.2418 (2)	0.13387 (13)	0.0532 (5)
C4	0.4296 (3)	0.2229 (2)	0.24763 (14)	0.0611 (5)
H4A	0.3063	0.1418	0.2600	0.073*
H4B	0.5473	0.1858	0.2687	0.073*
C5	0.4729 (3)	0.3733 (2)	0.31177 (13)	0.0527 (4)
C6	0.3592 (2)	0.47907 (18)	0.27140 (11)	0.0430 (4)
C7	0.3631 (2)	0.61509 (19)	0.33727 (11)	0.0451 (4)
H7	0.3727	0.5829	0.4066	0.054*
C8	0.1511 (3)	0.6401 (2)	0.30052 (12)	0.0515 (4)
H8A	0.0418	0.5526	0.3187	0.062*
H8B	0.1573	0.7374	0.3347	0.062*
C9	0.0961 (3)	0.6501 (2)	0.18920 (13)	0.0501 (4)
C10	0.5462 (2)	0.77008 (19)	0.34060 (11)	0.0423 (4)
C11	0.6075 (2)	0.88055 (19)	0.42492 (11)	0.0444 (4)
H11	0.5429	0.8588	0.4786	0.053*
C12	0.7650 (2)	1.02084 (19)	0.42544 (11)	0.0435 (4)
C13	0.8631 (2)	1.05607 (19)	0.34699 (13)	0.0488 (4)
C14	0.8088 (3)	0.9507 (2)	0.26496 (13)	0.0594 (5)
H14	0.8764	0.9739	0.2123	0.071*
C15	0.6475 (3)	0.8062 (2)	0.26271 (13)	0.0537 (5)
H15	0.6070	0.7321	0.2072	0.064*
C16	0.9975 (3)	1.2682 (2)	0.45983 (14)	0.0588 (5)
H16A	0.9450	1.3555	0.4466	0.071*
H16B	1.1334	1.3081	0.5079	0.071*
C17	0.3261 (4)	0.0808 (2)	0.07398 (17)	0.0780 (6)
H17A	0.3036	0.0949	0.0028	0.094*
H17B	0.1981	0.0114	0.0879	0.094*
H17C	0.4340	0.0349	0.0936	0.094*
C18	0.5966 (3)	0.3507 (3)	0.11116 (19)	0.0847 (7)
H18A	0.5749	0.3613	0.0396	0.102*
H18B	0.7053	0.3061	0.1328	0.102*
H18C	0.6377	0.4535	0.1468	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0605 (8)	0.0604 (7)	0.0408 (6)	0.0271 (6)	−0.0005 (5)	0.0020 (5)
O2	0.0675 (8)	0.0537 (7)	0.0547 (7)	0.0078 (6)	0.0153 (6)	−0.0092 (6)
O3	0.0609 (8)	0.0563 (8)	0.0749 (9)	0.0015 (7)	0.0253 (7)	−0.0061 (7)
O4	0.0792 (10)	0.1013 (11)	0.0519 (8)	0.0464 (9)	−0.0122 (7)	0.0011 (7)
O5	0.0756 (9)	0.0720 (9)	0.0688 (9)	0.0395 (8)	0.0057 (7)	0.0086 (7)
C1	0.0412 (9)	0.0449 (9)	0.0415 (9)	0.0121 (7)	0.0054 (7)	0.0052 (7)
C2	0.0559 (11)	0.0534 (10)	0.0482 (10)	0.0136 (9)	0.0022 (8)	−0.0037 (8)
C3	0.0522 (10)	0.0492 (10)	0.0545 (10)	0.0124 (9)	0.0136 (8)	−0.0006 (8)
C4	0.0610 (12)	0.0625 (12)	0.0646 (12)	0.0306 (10)	0.0105 (9)	0.0100 (9)
C5	0.0486 (10)	0.0636 (11)	0.0440 (10)	0.0200 (9)	0.0065 (8)	0.0089 (8)
C6	0.0392 (8)	0.0464 (9)	0.0378 (8)	0.0096 (7)	0.0066 (7)	0.0047 (7)
C7	0.0429 (9)	0.0540 (10)	0.0334 (8)	0.0123 (8)	0.0062 (7)	0.0032 (7)
C8	0.0437 (9)	0.0592 (11)	0.0492 (10)	0.0128 (8)	0.0141 (8)	0.0027 (8)
C9	0.0400 (9)	0.0520 (10)	0.0525 (10)	0.0122 (8)	0.0054 (8)	0.0014 (8)
C10	0.0388 (8)	0.0505 (10)	0.0373 (8)	0.0173 (8)	0.0056 (7)	0.0033 (7)
C11	0.0434 (9)	0.0539 (10)	0.0371 (8)	0.0178 (8)	0.0103 (7)	0.0033 (7)
C12	0.0410 (9)	0.0489 (10)	0.0399 (9)	0.0182 (8)	0.0044 (7)	−0.0006 (7)
C13	0.0397 (9)	0.0517 (10)	0.0531 (10)	0.0137 (8)	0.0108 (8)	0.0041 (8)
C14	0.0590 (12)	0.0641 (12)	0.0533 (11)	0.0110 (10)	0.0257 (9)	0.0010 (9)
C15	0.0547 (10)	0.0570 (11)	0.0441 (9)	0.0107 (9)	0.0148 (8)	−0.0060 (8)
C16	0.0488 (10)	0.0522 (11)	0.0665 (12)	0.0117 (9)	0.0053 (9)	−0.0026 (9)
C17	0.0876 (15)	0.0659 (13)	0.0806 (14)	0.0277 (12)	0.0190 (12)	−0.0068 (11)
C18	0.0732 (14)	0.0807 (15)	0.1004 (17)	0.0126 (12)	0.0430 (13)	−0.0001 (13)

Geometric parameters (Å, º) top

O1—C9	1.381 (2)	C7—C8	1.539 (2)
O1—C1	1.3864 (18)	C7—H7	0.9800
O2—C12	1.3784 (19)	C8—C9	1.485 (2)
O2—C16	1.426 (2)	C8—H8A	0.9700
O3—C13	1.382 (2)	C8—H8B	0.9700
O3—C16	1.422 (2)	C10—C15	1.382 (2)
O4—C5	1.2264 (19)	C10—C11	1.401 (2)
O5—C9	1.192 (2)	C11—C12	1.361 (2)
C1—C6	1.341 (2)	C11—H11	0.9300
C1—C2	1.482 (2)	C12—C13	1.375 (2)
C2—C3	1.529 (2)	C13—C14	1.357 (2)
C2—H2A	0.9700	C14—C15	1.395 (2)
C2—H2B	0.9700	C14—H14	0.9300
C3—C18	1.523 (3)	C15—H15	0.9300
C3—C17	1.525 (2)	C16—H16A	0.9700
C3—C4	1.529 (2)	C16—H16B	0.9700
C4—C5	1.506 (2)	C17—H17A	0.9600
C4—H4A	0.9700	C17—H17B	0.9600
C4—H4B	0.9700	C17—H17C	0.9600
C5—C6	1.461 (2)	C18—H18A	0.9600
C6—C7	1.499 (2)	C18—H18B	0.9600
C7—C10	1.530 (2)	C18—H18C	0.9600

C9—O1—C1	120.18 (12)	H8A—C8—H8B	107.9
C12—O2—C16	105.65 (13)	O5—C9—O1	116.87 (15)
C13—O3—C16	105.47 (13)	O5—C9—C8	126.67 (17)
C6—C1—O1	122.06 (14)	O1—C9—C8	116.40 (15)
C6—C1—C2	126.44 (15)	C15—C10—C11	119.43 (15)
O1—C1—C2	111.48 (13)	C15—C10—C7	122.52 (14)
C1—C2—C3	113.28 (14)	C11—C10—C7	118.02 (14)
C1—C2—H2A	108.9	C12—C11—C10	117.66 (15)
C3—C2—H2A	108.9	C12—C11—H11	121.2
C1—C2—H2B	108.9	C10—C11—H11	121.2
C3—C2—H2B	108.9	C11—C12—C13	122.35 (15)
H2A—C2—H2B	107.7	C11—C12—O2	128.05 (15)
C18—C3—C17	108.95 (16)	C13—C12—O2	109.57 (15)
C18—C3—C4	109.42 (16)	C14—C13—C12	121.28 (16)
C17—C3—C4	110.61 (15)	C14—C13—O3	128.78 (16)
C18—C3—C2	110.57 (16)	C12—C13—O3	109.92 (14)
C17—C3—C2	109.29 (15)	C13—C14—C15	117.36 (16)
C4—C3—C2	108.00 (14)	C13—C14—H14	121.3
C5—C4—C3	114.06 (15)	C15—C14—H14	121.3
C5—C4—H4A	108.7	C10—C15—C14	121.90 (16)
C3—C4—H4A	108.7	C10—C15—H15	119.1
C5—C4—H4B	108.7	C14—C15—H15	119.1
C3—C4—H4B	108.7	O3—C16—O2	108.29 (13)
H4A—C4—H4B	107.6	O3—C16—H16A	110.0
O4—C5—C6	120.57 (17)	O2—C16—H16A	110.0
O4—C5—C4	121.93 (17)	O3—C16—H16B	110.0
C6—C5—C4	117.48 (14)	O2—C16—H16B	110.0
C1—C6—C5	118.22 (15)	H16A—C16—H16B	108.4
C1—C6—C7	120.98 (15)	C3—C17—H17A	109.5
C5—C6—C7	120.74 (14)	C3—C17—H17B	109.5
C6—C7—C10	115.02 (13)	H17A—C17—H17B	109.5
C6—C7—C8	107.43 (13)	C3—C17—H17C	109.5
C10—C7—C8	110.91 (13)	H17A—C17—H17C	109.5
C6—C7—H7	107.7	H17B—C17—H17C	109.5
C10—C7—H7	107.7	C3—C18—H18A	109.5
C8—C7—H7	107.7	C3—C18—H18B	109.5
C9—C8—C7	112.28 (14)	H18A—C18—H18B	109.5
C9—C8—H8A	109.1	C3—C18—H18C	109.5
C7—C8—H8A	109.1	H18A—C18—H18C	109.5
C9—C8—H8B	109.1	H18B—C18—H18C	109.5
C7—C8—H8B	109.1

C9—O1—C1—C6	−16.9 (2)	C1—O1—C9—C8	−7.8 (2)
C9—O1—C1—C2	164.54 (14)	C7—C8—C9—O5	−140.99 (18)
C6—C1—C2—C3	−19.7 (2)	C7—C8—C9—O1	42.0 (2)
O1—C1—C2—C3	158.79 (13)	C6—C7—C10—C15	25.4 (2)
C1—C2—C3—C18	−75.18 (19)	C8—C7—C10—C15	−96.77 (18)
C1—C2—C3—C17	164.90 (15)	C6—C7—C10—C11	−156.64 (14)
C1—C2—C3—C4	44.5 (2)	C8—C7—C10—C11	81.21 (17)
C18—C3—C4—C5	66.6 (2)	C15—C10—C11—C12	0.6 (2)
C17—C3—C4—C5	−173.39 (16)	C7—C10—C11—C12	−177.43 (14)
C2—C3—C4—C5	−53.84 (19)	C10—C11—C12—C13	0.0 (2)
C3—C4—C5—O4	−144.53 (18)	C10—C11—C12—O2	−178.04 (14)
C3—C4—C5—C6	36.9 (2)	C16—O2—C12—C11	−174.70 (16)
O1—C1—C6—C5	−178.56 (13)	C16—O2—C12—C13	7.04 (18)
C2—C1—C6—C5	−0.2 (3)	C11—C12—C13—C14	−0.8 (3)
O1—C1—C6—C7	4.3 (2)	O2—C12—C13—C14	177.59 (15)
C2—C1—C6—C7	−177.43 (15)	C11—C12—C13—O3	−179.33 (14)
O4—C5—C6—C1	173.12 (17)	O2—C12—C13—O3	−0.95 (19)
C4—C5—C6—C1	−8.3 (2)	C16—O3—C13—C14	176.03 (18)
O4—C5—C6—C7	−9.7 (2)	C16—O3—C13—C12	−5.57 (18)
C4—C5—C6—C7	168.93 (15)	C12—C13—C14—C15	0.9 (3)
C1—C6—C7—C10	−95.19 (18)	O3—C13—C14—C15	179.10 (16)
C5—C6—C7—C10	87.70 (18)	C11—C10—C15—C14	−0.5 (3)
C1—C6—C7—C8	28.8 (2)	C7—C10—C15—C14	177.42 (15)
C5—C6—C7—C8	−148.29 (14)	C13—C14—C15—C10	−0.2 (3)
C6—C7—C8—C9	−50.09 (18)	C13—O3—C16—O2	9.87 (18)
C10—C7—C8—C9	76.39 (17)	C12—O2—C16—O3	−10.46 (18)
C1—O1—C9—O5	174.88 (14)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈O₅
M_r	314.32
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.963 (1), 8.957 (2), 13.594 (3)
α, β, γ (°)	90.16 (2), 103.11 (2), 109.60 (2)
V (Å³)	775.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.54 × 0.48 × 0.24

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3072, 2731, 1937
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.102, 1.03
No. of reflections	2731
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.16

Computer programs: XSCANS (Siemens, 1994), XSCANS, SHELXTL (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top

O1—C9	1.381 (2)	C1—C6	1.341 (2)
O1—C1	1.3864 (18)	C5—C6	1.461 (2)
O4—C5	1.2264 (19)	C8—C9	1.485 (2)
O5—C9	1.192 (2)

C6—C1—O1	122.06 (14)	C6—C7—C8	107.43 (13)
C6—C1—C2	126.44 (15)	O5—C9—O1	116.87 (15)
C1—C6—C5	118.22 (15)	O1—C9—C8	116.40 (15)
C6—C7—C10	115.02 (13)

C9—O1—C1—C6	−16.9 (2)	C4—C5—C6—C1	−8.3 (2)
C2—C1—C6—C5	−0.2 (3)	C1—C6—C7—C8	28.8 (2)

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