9-(2-Hydro­xy-4,4-di­methyl-6-oxo­cyclo­hex-1-enyl)-3,3,7-tri­methyl-1,2,3,4-hexa­hydro-9H-xanthen-1-one

The title compound, C₂₄H₂₈O₄, has been synthesized by the reaction of 5-methyl­salicyl­aldehyde and 5,5-di­methyl-1,3-hexane­dione in water catalyzed by triethyl­benzyl­ammonium chloride. The central pyran ring and outer cyclo­hexene ring of the oxanthene moiety adopt boat and half-chair conformations, respectively. The other cyclo­hexene ring bonded to the pyran moiety has a skew-boat form.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.084
• wR factor = 0.167
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.36

   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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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

---

Computing details

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2000–2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

3,3,7-trimethyl-9-(5,5-dimethyl-3-hydroxy-2-cyclohexene- 1-one-2-yl)-1-oxo-1,2,3,4,9,10-hexahydroxanthene

Crystal data

C24H28O4	Dx = 1.260 Mg m^−3
Mr = 380.46	Melting point = 491–492 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -p 2ac 2ab	Cell parameters from 16291 reflections
a = 15.559 (3) Å	θ = 3.2–27.5°
b = 11.1768 (19) Å	µ = 0.08 mm^−1
c = 23.057 (4) Å	T = 193 K
V = 4009.7 (11) Å^3	Platelet, colorless
Z = 8	0.50 × 0.44 × 0.09 mm
F(000) = 1632

Data collection

Rigaku Mercury diffractometer	4586 independent reflections
Radiation source: fine-focus sealed tube	4060 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
Detector resolution: 7.31 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −20→20
Absorption correction: multi-scan (Jacobson, 1998)	k = −14→14
Tmin = 0.959, Tmax = 0.992	l = −29→25
42649 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	w = 1/[σ^2(Fo^2) + (0.0425P)^2 + 3.8447P] where P = (Fo^2 + 2Fc^2)/3
4586 reflections	(Δ/σ)max < 0.001
263 parameters	Δρmax = 0.50 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

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.

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.51809 (11)	0.72013 (15)	0.46441 (7)	0.0299 (4)
O2	0.33493 (13)	1.02752 (16)	0.52857 (8)	0.0392 (5)
O3	0.40994 (13)	0.94837 (19)	0.67231 (8)	0.0468 (5)
O4	0.29587 (12)	0.68028 (16)	0.53686 (7)	0.0322 (4)
C1	0.53210 (15)	0.6742 (2)	0.52013 (10)	0.0260 (5)
C2	0.49515 (14)	0.7237 (2)	0.56866 (11)	0.0259 (5)
C3	0.43668 (14)	0.8327 (2)	0.56512 (10)	0.0249 (5)
H3	0.4691	0.9007	0.5829	0.030*
C4	0.42109 (14)	0.8661 (2)	0.50234 (10)	0.0239 (5)
C5	0.46129 (15)	0.8114 (2)	0.45790 (10)	0.0257 (5)
C6	0.58321 (16)	0.5722 (2)	0.52222 (12)	0.0318 (6)
H6	0.6082	0.5405	0.4879	0.038*
C7	0.59674 (16)	0.5185 (2)	0.57502 (12)	0.0336 (6)
H7	0.6307	0.4480	0.5769	0.040*
C8	0.56187 (16)	0.5648 (2)	0.62598 (11)	0.0326 (6)
C9	0.51201 (16)	0.6676 (2)	0.62168 (11)	0.0317 (6)
H9	0.4885	0.7011	0.6561	0.038*
C10	0.36586 (15)	0.9666 (2)	0.48906 (11)	0.0283 (5)
C11	0.34807 (16)	0.9995 (2)	0.42653 (11)	0.0321 (6)
H11A	0.3850	1.0682	0.4160	0.039*
H11B	0.2876	1.0262	0.4234	0.039*
C12	0.36303 (17)	0.8990 (2)	0.38243 (11)	0.0317 (6)
C13	0.45069 (16)	0.8423 (2)	0.39541 (10)	0.0295 (5)
H13A	0.4573	0.7689	0.3718	0.035*
H13B	0.4967	0.8988	0.3839	0.035*
C14	0.35594 (14)	0.8162 (2)	0.60140 (10)	0.0249 (5)
C15	0.35357 (16)	0.8775 (2)	0.65712 (11)	0.0334 (6)
C16	0.28197 (18)	0.8459 (3)	0.69887 (12)	0.0413 (7)
H16A	0.2731	0.9142	0.7256	0.050*
H16B	0.3004	0.7766	0.7225	0.050*
C17	0.19696 (16)	0.8159 (2)	0.67026 (11)	0.0305 (5)
C18	0.21112 (16)	0.7229 (2)	0.62250 (11)	0.0311 (6)
H18A	0.2145	0.6427	0.6406	0.037*
H18B	0.1606	0.7234	0.5964	0.037*
C19	0.29045 (15)	0.7423 (2)	0.58674 (10)	0.0251 (5)
C20	0.5775 (2)	0.5052 (3)	0.68354 (13)	0.0451 (7)
H20A	0.5483	0.5504	0.7142	0.068*
H20B	0.6394	0.5031	0.6914	0.068*
H20C	0.5549	0.4234	0.6825	0.068*
C21	0.29149 (17)	0.8051 (2)	0.38696 (12)	0.0382 (6)
H21A	0.2897	0.7732	0.4265	0.057*
H21B	0.3030	0.7398	0.3596	0.057*
H21C	0.2361	0.8422	0.3776	0.057*
C22	0.3647 (2)	0.9509 (3)	0.32117 (13)	0.0475 (7)
H22A	0.3095	0.9896	0.3129	0.071*
H22B	0.3746	0.8865	0.2931	0.071*
H22C	0.4110	1.0100	0.3182	0.071*
C23	0.1325 (2)	0.7688 (3)	0.71442 (13)	0.0481 (8)
H23A	0.1561	0.6975	0.7334	0.072*
H23B	0.0788	0.7479	0.6947	0.072*
H23C	0.1212	0.8306	0.7436	0.072*
C24	0.1592 (2)	0.9305 (2)	0.64239 (14)	0.0441 (7)
H24A	0.1515	0.9918	0.6723	0.066*
H24B	0.1035	0.9119	0.6247	0.066*
H24C	0.1986	0.9602	0.6126	0.066*
H4	0.249 (2)	0.637 (3)	0.5316 (13)	0.053 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0322 (9)	0.0273 (9)	0.0302 (9)	0.0094 (7)	0.0020 (7)	−0.0007 (7)
O2	0.0440 (11)	0.0320 (10)	0.0415 (11)	0.0151 (8)	0.0002 (9)	−0.0076 (8)
O3	0.0447 (12)	0.0581 (13)	0.0375 (11)	−0.0202 (10)	0.0026 (9)	−0.0215 (10)
O4	0.0341 (10)	0.0304 (9)	0.0321 (9)	−0.0094 (8)	0.0057 (8)	−0.0126 (8)
C1	0.0234 (11)	0.0249 (12)	0.0296 (12)	−0.0004 (9)	−0.0029 (9)	−0.0001 (10)
C2	0.0215 (11)	0.0242 (12)	0.0321 (13)	−0.0011 (9)	−0.0033 (9)	−0.0023 (10)
C3	0.0222 (11)	0.0238 (11)	0.0286 (12)	−0.0007 (9)	−0.0020 (9)	−0.0059 (9)
C4	0.0210 (11)	0.0214 (11)	0.0291 (12)	−0.0018 (9)	0.0018 (9)	−0.0021 (9)
C5	0.0224 (11)	0.0213 (11)	0.0335 (13)	−0.0004 (9)	−0.0007 (9)	−0.0014 (10)
C6	0.0280 (13)	0.0286 (13)	0.0387 (14)	0.0054 (10)	−0.0014 (11)	−0.0038 (11)
C7	0.0277 (13)	0.0275 (13)	0.0457 (15)	0.0054 (10)	−0.0096 (11)	0.0001 (11)
C8	0.0298 (13)	0.0295 (13)	0.0385 (14)	−0.0042 (11)	−0.0098 (11)	0.0035 (11)
C9	0.0297 (13)	0.0355 (13)	0.0298 (13)	−0.0013 (11)	−0.0047 (10)	−0.0058 (11)
C10	0.0239 (12)	0.0231 (12)	0.0378 (14)	0.0002 (9)	−0.0001 (10)	−0.0050 (10)
C11	0.0277 (12)	0.0268 (12)	0.0417 (15)	0.0044 (10)	−0.0015 (11)	0.0040 (11)
C12	0.0336 (13)	0.0312 (13)	0.0302 (13)	0.0037 (11)	−0.0015 (10)	0.0033 (11)
C13	0.0318 (13)	0.0282 (12)	0.0286 (13)	0.0028 (10)	0.0030 (10)	0.0010 (10)
C14	0.0247 (11)	0.0229 (11)	0.0272 (12)	0.0004 (9)	−0.0011 (9)	−0.0054 (9)
C15	0.0306 (13)	0.0377 (14)	0.0321 (14)	−0.0038 (11)	−0.0004 (10)	−0.0102 (11)
C16	0.0419 (16)	0.0514 (17)	0.0306 (14)	−0.0027 (13)	−0.0001 (12)	−0.0089 (13)
C17	0.0311 (13)	0.0335 (13)	0.0268 (12)	−0.0041 (11)	0.0021 (10)	−0.0077 (11)
C18	0.0315 (13)	0.0274 (12)	0.0345 (13)	−0.0042 (10)	0.0045 (10)	−0.0059 (11)
C19	0.0290 (12)	0.0220 (11)	0.0242 (11)	0.0012 (9)	−0.0003 (9)	−0.0038 (9)
C20	0.0503 (18)	0.0427 (16)	0.0422 (16)	0.0064 (14)	−0.0168 (14)	0.0032 (13)
C21	0.0357 (14)	0.0366 (14)	0.0422 (15)	0.0012 (12)	−0.0067 (12)	−0.0035 (12)
C22	0.0539 (18)	0.0508 (18)	0.0378 (16)	0.0071 (15)	−0.0043 (14)	0.0113 (14)
C23	0.0482 (17)	0.0562 (19)	0.0398 (16)	−0.0130 (15)	0.0141 (13)	−0.0134 (14)
C24	0.0444 (17)	0.0357 (15)	0.0523 (18)	0.0047 (13)	0.0057 (14)	−0.0071 (13)

Geometric parameters (Å, º)

O1—C5	1.358 (3)	C13—H13A	0.9900
O1—C1	1.401 (3)	C13—H13B	0.9900
O2—C10	1.235 (3)	C14—C19	1.354 (3)
O3—C15	1.233 (3)	C14—C15	1.456 (3)
O4—C19	1.346 (3)	C15—C16	1.514 (4)
O4—H4	0.88 (4)	C16—C17	1.516 (4)
C1—C2	1.374 (3)	C16—H16A	0.9900
C1—C6	1.390 (3)	C16—H16B	0.9900
C2—C9	1.398 (3)	C17—C23	1.523 (4)
C2—C3	1.523 (3)	C17—C18	1.530 (3)
C3—C4	1.514 (3)	C17—C24	1.548 (4)
C3—C14	1.521 (3)	C18—C19	1.500 (3)
C3—H3	1.0000	C18—H18A	0.9900
C4—C5	1.347 (3)	C18—H18B	0.9900
C4—C10	1.447 (3)	C20—H20A	0.9800
C5—C13	1.491 (3)	C20—H20B	0.9800
C6—C7	1.374 (4)	C20—H20C	0.9800
C6—H6	0.9500	C21—H21A	0.9800
C7—C8	1.394 (4)	C21—H21B	0.9800
C7—H7	0.9500	C21—H21C	0.9800
C8—C9	1.390 (4)	C22—H22A	0.9800
C8—C20	1.505 (4)	C22—H22B	0.9800
C9—H9	0.9500	C22—H22C	0.9800
C10—C11	1.513 (4)	C23—H23A	0.9800
C11—C12	1.533 (4)	C23—H23B	0.9800
C11—H11A	0.9900	C23—H23C	0.9800
C11—H11B	0.9900	C24—H24A	0.9800
C12—C22	1.527 (4)	C24—H24B	0.9800
C12—C13	1.533 (3)	C24—H24C	0.9800
C12—C21	1.533 (4)
C5—O1—C1	118.56 (18)	C15—C14—C3	116.7 (2)
C19—O4—H4	111 (2)	O3—C15—C14	122.3 (2)
C2—C1—C6	122.7 (2)	O3—C15—C16	119.5 (2)
C2—C1—O1	122.3 (2)	C14—C15—C16	118.0 (2)
C6—C1—O1	114.9 (2)	C15—C16—C17	114.6 (2)
C1—C2—C9	116.9 (2)	C15—C16—H16A	108.6
C1—C2—C3	121.9 (2)	C17—C16—H16A	108.6
C9—C2—C3	121.2 (2)	C15—C16—H16B	108.6
C4—C3—C14	115.05 (19)	C17—C16—H16B	108.6
C4—C3—C2	110.12 (19)	H16A—C16—H16B	107.6
C14—C3—C2	111.51 (19)	C16—C17—C23	111.1 (2)
C4—C3—H3	106.5	C16—C17—C18	109.8 (2)
C14—C3—H3	106.5	C23—C17—C18	109.9 (2)
C2—C3—H3	106.5	C16—C17—C24	109.2 (2)
C5—C4—C10	117.8 (2)	C23—C17—C24	108.3 (2)
C5—C4—C3	122.8 (2)	C18—C17—C24	108.5 (2)
C10—C4—C3	119.2 (2)	C19—C18—C17	114.6 (2)
C4—C5—O1	124.0 (2)	C19—C18—H18A	108.6
C4—C5—C13	125.3 (2)	C17—C18—H18A	108.6
O1—C5—C13	110.7 (2)	C19—C18—H18B	108.6
C7—C6—C1	118.5 (2)	C17—C18—H18B	108.6
C7—C6—H6	120.8	H18A—C18—H18B	107.6
C1—C6—H6	120.8	O4—C19—C14	118.7 (2)
C6—C7—C8	121.7 (2)	O4—C19—C18	116.5 (2)
C6—C7—H7	119.2	C14—C19—C18	124.8 (2)
C8—C7—H7	119.2	C8—C20—H20A	109.5
C9—C8—C7	117.7 (2)	C8—C20—H20B	109.5
C9—C8—C20	121.3 (2)	H20A—C20—H20B	109.5
C7—C8—C20	121.1 (2)	C8—C20—H20C	109.5
C8—C9—C2	122.5 (2)	H20A—C20—H20C	109.5
C8—C9—H9	118.8	H20B—C20—H20C	109.5
C2—C9—H9	118.8	C12—C21—H21A	109.5
O2—C10—C4	120.2 (2)	C12—C21—H21B	109.5
O2—C10—C11	119.8 (2)	H21A—C21—H21B	109.5
C4—C10—C11	119.9 (2)	C12—C21—H21C	109.5
C10—C11—C12	115.2 (2)	H21A—C21—H21C	109.5
C10—C11—H11A	108.5	H21B—C21—H21C	109.5
C12—C11—H11A	108.5	C12—C22—H22A	109.5
C10—C11—H11B	108.5	C12—C22—H22B	109.5
C12—C11—H11B	108.5	H22A—C22—H22B	109.5
H11A—C11—H11B	107.5	C12—C22—H22C	109.5
C22—C12—C13	108.8 (2)	H22A—C22—H22C	109.5
C22—C12—C11	109.7 (2)	H22B—C22—H22C	109.5
C13—C12—C11	108.0 (2)	C17—C23—H23A	109.5
C22—C12—C21	109.6 (2)	C17—C23—H23B	109.5
C13—C12—C21	110.5 (2)	H23A—C23—H23B	109.5
C11—C12—C21	110.3 (2)	C17—C23—H23C	109.5
C5—C13—C12	112.5 (2)	H23A—C23—H23C	109.5
C5—C13—H13A	109.1	H23B—C23—H23C	109.5
C12—C13—H13A	109.1	C17—C24—H24A	109.5
C5—C13—H13B	109.1	C17—C24—H24B	109.5
C12—C13—H13B	109.1	H24A—C24—H24B	109.5
H13A—C13—H13B	107.8	C17—C24—H24C	109.5
C19—C14—C15	119.2 (2)	H24A—C24—H24C	109.5
C19—C14—C3	124.0 (2)	H24B—C24—H24C	109.5
C5—O1—C1—C2	−4.7 (3)	O2—C10—C11—C12	−160.7 (2)
C5—O1—C1—C6	172.8 (2)	C4—C10—C11—C12	21.2 (3)
C6—C1—C2—C9	0.9 (3)	C10—C11—C12—C22	−166.0 (2)
O1—C1—C2—C9	178.2 (2)	C10—C11—C12—C13	−47.6 (3)
C6—C1—C2—C3	−177.7 (2)	C10—C11—C12—C21	73.2 (3)
O1—C1—C2—C3	−0.4 (3)	C4—C5—C13—C12	−26.7 (3)
C1—C2—C3—C4	5.2 (3)	O1—C5—C13—C12	153.8 (2)
C9—C2—C3—C4	−173.3 (2)	C22—C12—C13—C5	168.4 (2)
C1—C2—C3—C14	134.2 (2)	C11—C12—C13—C5	49.4 (3)
C9—C2—C3—C14	−44.3 (3)	C21—C12—C13—C5	−71.2 (3)
C14—C3—C4—C5	−132.8 (2)	C4—C3—C14—C19	53.6 (3)
C2—C3—C4—C5	−5.8 (3)	C2—C3—C14—C19	−72.7 (3)
C14—C3—C4—C10	52.0 (3)	C4—C3—C14—C15	−131.2 (2)
C2—C3—C4—C10	179.0 (2)	C2—C3—C14—C15	102.5 (2)
C10—C4—C5—O1	176.6 (2)	C19—C14—C15—O3	−177.9 (3)
C3—C4—C5—O1	1.3 (4)	C3—C14—C15—O3	6.7 (4)
C10—C4—C5—C13	−2.9 (4)	C19—C14—C15—C16	6.1 (4)
C3—C4—C5—C13	−178.1 (2)	C3—C14—C15—C16	−169.3 (2)
C1—O1—C5—C4	4.3 (3)	O3—C15—C16—C17	149.5 (3)
C1—O1—C5—C13	−176.17 (19)	C14—C15—C16—C17	−34.4 (4)
C2—C1—C6—C7	0.4 (4)	C15—C16—C17—C23	172.1 (2)
O1—C1—C6—C7	−177.1 (2)	C15—C16—C17—C18	50.3 (3)
C1—C6—C7—C8	−1.1 (4)	C15—C16—C17—C24	−68.5 (3)
C6—C7—C8—C9	0.4 (4)	C16—C17—C18—C19	−40.4 (3)
C6—C7—C8—C20	−179.8 (2)	C23—C17—C18—C19	−163.0 (2)
C7—C8—C9—C2	1.0 (4)	C24—C17—C18—C19	78.8 (3)
C20—C8—C9—C2	−178.8 (2)	C15—C14—C19—O4	−175.8 (2)
C1—C2—C9—C8	−1.6 (4)	C3—C14—C19—O4	−0.8 (4)
C3—C2—C9—C8	177.0 (2)	C15—C14—C19—C18	3.7 (4)
C5—C4—C10—O2	−172.3 (2)	C3—C14—C19—C18	178.7 (2)
C3—C4—C10—O2	3.1 (3)	C17—C18—C19—O4	−165.7 (2)
C5—C4—C10—C11	5.9 (3)	C17—C18—C19—C14	14.8 (4)
C3—C4—C10—C11	−178.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2^i	0.88 (4)	1.79 (4)	2.663 (3)	169 (3)

Symmetry code: (i) −x+1/2, y−1/2, z.