9-(2,4-Dichloro-phen-yl)-3,3,6,6-tetra-methyl-3,4,5,6-tetra-hydro-9H-xanthene-1,8(2H,7H)-dione.

The title compound, C(23)H(24)Cl(2)O(3), was synthesized by reaction of 2,4-dichloro-benzaldehyde and 5,5-dimethyl-cyclo-hexane-1,3-dione in ethyl-ene glycol. The central ring of the xanthene moiety is almost planar (with an r.m.s. deviation of 0.0268 Å from the least-squares plane) while the two outer rings, in a cis arrangement, display envelope conformations. The ring of the 2,4-dichloro-phenyl substituent is nearly perpendicular [85.89 (4)°] to the xanthene ring system.

Related literature

For related structures, see: Odabaşoğlu et al. (2008 ▶); Bigdeli et al. (2007 ▶); Tu et al. (2002 ▶, 2004 ▶); Jeyakanthan et al. (1999 ▶); Li et al. (2005 ▶); Shi et al. (1997 ▶). For applications of xanthene derivatives, see: Poupelin et al. (1978 ▶); Lambert et al. (1997 ▶); Menchen et al. (2003 ▶); Banerjee & Mukherjee (1981 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C23H24Cl2O3

M = 419.32

Monoclinic,

a = 9.8154 (10) Å

b = 19.833 (2) Å

c = 11.4441 (11) Å

β = 111.873 (2)°

V = 2067.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 296 K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.936, T max = 0.967

13137 measured reflections

4961 independent reflections

3331 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.124

S = 1.02

4961 reflections

257 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.55 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046702/dn2622sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046702/dn2622Isup2.hkl

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

C23H24Cl2O3	F(000) = 880
Mr = 419.32	Dx = 1.347 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3489 reflections
a = 9.8154 (10) Å	θ = 2.2–27.1°
b = 19.833 (2) Å	µ = 0.34 mm−1
c = 11.4441 (11) Å	T = 296 K
β = 111.873 (2)°	Prism, colorless
V = 2067.4 (4) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Bruker APEX CCD diffractometer	4961 independent reflections
Radiation source: fine-focus sealed tube	3331 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω scans	θmax = 28.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −13→11
Tmin = 0.936, Tmax = 0.967	k = −25→26
13137 measured reflections	l = −13→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0573P)2 + 0.4531P] where P = (Fo2 + 2Fc2)/3
4961 reflections	(Δ/σ)max < 0.001
257 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.55 e Å−3

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
Cl1	0.48123 (7)	0.49352 (3)	0.81227 (5)	0.05835 (18)
Cl2	0.17633 (9)	0.68975 (4)	0.92235 (7)	0.0867 (3)
O1	0.37359 (14)	0.63325 (7)	0.31501 (11)	0.0429 (3)
O2	0.69826 (15)	0.60451 (8)	0.73455 (13)	0.0535 (4)
O3	0.19747 (16)	0.47392 (7)	0.52949 (13)	0.0495 (4)
C1	0.6678 (2)	0.63036 (10)	0.63116 (18)	0.0396 (4)
C2	0.7753 (2)	0.67506 (10)	0.60270 (19)	0.0437 (5)
H2A	0.8411	0.6468	0.5785	0.052*
H2B	0.8341	0.6986	0.6793	0.052*
C3	0.7073 (2)	0.72708 (10)	0.49949 (18)	0.0399 (4)
C4	0.6005 (2)	0.68988 (11)	0.38461 (18)	0.0447 (5)
H4A	0.5426	0.7227	0.3233	0.054*
H4B	0.6561	0.6637	0.3461	0.054*
C5	0.1471 (2)	0.57908 (11)	0.20690 (17)	0.0450 (5)
H5A	0.1701	0.5446	0.1569	0.054*
H5B	0.1296	0.6209	0.1598	0.054*
C6	0.0085 (2)	0.55903 (10)	0.22869 (18)	0.0409 (4)
C7	0.0469 (2)	0.49772 (10)	0.31638 (19)	0.0426 (4)
H7A	−0.0365	0.4871	0.3390	0.051*
H7B	0.0636	0.4594	0.2708	0.051*
C8	0.1799 (2)	0.50728 (9)	0.43512 (18)	0.0369 (4)
C9	0.42019 (19)	0.56963 (9)	0.55622 (16)	0.0336 (4)
H9	0.4699	0.5268	0.5881	0.040*
C10	0.52669 (18)	0.61624 (9)	0.52976 (16)	0.0345 (4)
C11	0.50031 (19)	0.64432 (9)	0.41722 (17)	0.0368 (4)
C12	0.27441 (19)	0.58782 (9)	0.32733 (17)	0.0363 (4)
C13	0.29182 (19)	0.55638 (9)	0.43501 (17)	0.0342 (4)
C14	−0.0441 (2)	0.61645 (11)	0.2899 (2)	0.0544 (6)
H14A	0.0286	0.6256	0.3717	0.082*
H14B	−0.1346	0.6038	0.2980	0.082*
H14C	−0.0595	0.6561	0.2385	0.082*
C15	−0.1116 (2)	0.54084 (13)	0.1031 (2)	0.0561 (6)
H15A	−0.1238	0.5771	0.0444	0.084*
H15B	−0.2022	0.5335	0.1151	0.084*
H15C	−0.0845	0.5005	0.0707	0.084*
C16	0.6252 (2)	0.78085 (11)	0.5432 (2)	0.0560 (6)
H16A	0.5859	0.8140	0.4782	0.084*
H16B	0.6917	0.8021	0.6181	0.084*
H16C	0.5465	0.7601	0.5608	0.084*
C17	0.8269 (2)	0.76069 (11)	0.4648 (2)	0.0512 (5)
H17A	0.8768	0.7272	0.4351	0.077*
H17B	0.8958	0.7826	0.5377	0.077*
H17C	0.7833	0.7935	0.3998	0.077*
C18	0.36693 (19)	0.59939 (9)	0.65453 (16)	0.0342 (4)
C19	0.3866 (2)	0.56903 (10)	0.76900 (17)	0.0384 (4)
C20	0.3308 (2)	0.59704 (11)	0.85255 (18)	0.0453 (5)
H20	0.3460	0.5763	0.9293	0.054*
C21	0.2526 (2)	0.65597 (11)	0.8201 (2)	0.0492 (5)
C22	0.2324 (2)	0.68823 (11)	0.7101 (2)	0.0521 (5)
H22	0.1810	0.7287	0.6903	0.063*
C23	0.2899 (2)	0.65966 (10)	0.62823 (19)	0.0441 (5)
H23	0.2765	0.6816	0.5529	0.053*

	U11	U22	U33	U12	U13	U23
Cl1	0.0722 (4)	0.0568 (3)	0.0467 (3)	0.0159 (3)	0.0229 (3)	0.0185 (2)
Cl2	0.1098 (6)	0.0919 (5)	0.0885 (5)	−0.0067 (4)	0.0717 (5)	−0.0323 (4)
O1	0.0408 (7)	0.0571 (8)	0.0295 (7)	−0.0146 (6)	0.0117 (6)	0.0025 (6)
O2	0.0466 (8)	0.0693 (10)	0.0385 (8)	−0.0043 (7)	0.0090 (6)	0.0099 (7)
O3	0.0550 (8)	0.0487 (8)	0.0469 (9)	−0.0060 (7)	0.0217 (7)	0.0081 (7)
C1	0.0378 (10)	0.0441 (11)	0.0370 (10)	0.0025 (8)	0.0139 (8)	−0.0023 (8)
C2	0.0358 (10)	0.0477 (11)	0.0460 (12)	−0.0039 (8)	0.0136 (9)	−0.0014 (9)
C3	0.0368 (9)	0.0430 (10)	0.0417 (11)	−0.0042 (8)	0.0165 (8)	−0.0025 (8)
C4	0.0445 (11)	0.0556 (12)	0.0362 (10)	−0.0118 (9)	0.0178 (9)	0.0004 (9)
C5	0.0427 (11)	0.0608 (13)	0.0305 (10)	−0.0103 (9)	0.0125 (8)	−0.0009 (9)
C6	0.0366 (9)	0.0465 (11)	0.0399 (10)	−0.0028 (8)	0.0145 (8)	0.0024 (8)
C7	0.0381 (10)	0.0425 (11)	0.0492 (12)	−0.0048 (8)	0.0187 (9)	0.0006 (9)
C8	0.0402 (10)	0.0335 (9)	0.0424 (11)	0.0010 (8)	0.0215 (8)	−0.0003 (8)
C9	0.0362 (9)	0.0351 (9)	0.0323 (9)	0.0024 (7)	0.0160 (8)	0.0009 (7)
C10	0.0331 (9)	0.0401 (10)	0.0320 (9)	0.0000 (7)	0.0143 (8)	−0.0012 (7)
C11	0.0340 (9)	0.0450 (10)	0.0324 (9)	−0.0049 (8)	0.0136 (8)	−0.0034 (8)
C12	0.0358 (9)	0.0415 (10)	0.0352 (10)	−0.0054 (8)	0.0174 (8)	−0.0026 (8)
C13	0.0352 (9)	0.0366 (9)	0.0341 (9)	0.0000 (7)	0.0167 (8)	−0.0017 (7)
C14	0.0524 (12)	0.0540 (13)	0.0575 (14)	0.0137 (10)	0.0210 (11)	0.0055 (10)
C15	0.0432 (11)	0.0692 (15)	0.0485 (13)	−0.0118 (11)	0.0084 (10)	0.0017 (11)
C16	0.0478 (12)	0.0498 (12)	0.0728 (16)	−0.0003 (10)	0.0252 (11)	−0.0086 (11)
C17	0.0466 (11)	0.0529 (12)	0.0578 (14)	−0.0114 (10)	0.0236 (10)	−0.0036 (10)
C18	0.0356 (9)	0.0382 (10)	0.0303 (9)	−0.0028 (7)	0.0139 (7)	−0.0010 (7)
C19	0.0401 (10)	0.0422 (10)	0.0318 (9)	−0.0035 (8)	0.0120 (8)	0.0005 (8)
C20	0.0506 (11)	0.0550 (12)	0.0338 (10)	−0.0132 (10)	0.0198 (9)	−0.0049 (9)
C21	0.0542 (12)	0.0544 (13)	0.0502 (13)	−0.0108 (10)	0.0322 (11)	−0.0170 (10)
C22	0.0553 (12)	0.0459 (12)	0.0600 (14)	0.0058 (10)	0.0270 (11)	−0.0067 (10)
C23	0.0521 (11)	0.0431 (11)	0.0396 (11)	0.0056 (9)	0.0202 (9)	0.0033 (8)

Cl1—C19	1.734 (2)	C9—C10	1.508 (2)
Cl2—C21	1.741 (2)	C9—C13	1.509 (2)
O1—C11	1.371 (2)	C9—C18	1.525 (2)
O1—C12	1.372 (2)	C9—H9	0.9800
O2—C1	1.220 (2)	C10—C11	1.337 (2)
O3—C8	1.223 (2)	C12—C13	1.334 (2)
C1—C10	1.465 (3)	C14—H14A	0.9600
C1—C2	1.504 (3)	C14—H14B	0.9600
C2—C3	1.522 (3)	C14—H14C	0.9600
C2—H2A	0.9700	C15—H15A	0.9600
C2—H2B	0.9700	C15—H15B	0.9600
C3—C17	1.526 (3)	C15—H15C	0.9600
C3—C16	1.528 (3)	C16—H16A	0.9600
C3—C4	1.531 (3)	C16—H16B	0.9600
C4—C11	1.482 (3)	C16—H16C	0.9600
C4—H4A	0.9700	C17—H17A	0.9600
C4—H4B	0.9700	C17—H17B	0.9600
C5—C12	1.486 (3)	C17—H17C	0.9600
C5—C6	1.525 (3)	C18—C23	1.386 (3)
C5—H5A	0.9700	C18—C19	1.388 (2)
C5—H5B	0.9700	C19—C20	1.384 (3)
C6—C15	1.524 (3)	C20—C21	1.371 (3)
C6—C14	1.524 (3)	C20—H20	0.9300
C6—C7	1.531 (3)	C21—C22	1.360 (3)
C7—C8	1.505 (3)	C22—C23	1.383 (3)
C7—H7A	0.9700	C22—H22	0.9300
C7—H7B	0.9700	C23—H23	0.9300
C8—C13	1.468 (2)
C11—O1—C12	118.07 (14)	C10—C11—O1	122.95 (16)
O2—C1—C10	120.39 (18)	C10—C11—C4	126.02 (16)
O2—C1—C2	121.29 (17)	O1—C11—C4	111.03 (15)
C10—C1—C2	118.28 (17)	C13—C12—O1	123.39 (16)
C1—C2—C3	115.27 (15)	C13—C12—C5	125.20 (17)
C1—C2—H2A	108.5	O1—C12—C5	111.40 (15)
C3—C2—H2A	108.5	C12—C13—C8	118.18 (16)
C1—C2—H2B	108.5	C12—C13—C9	122.91 (16)
C3—C2—H2B	108.5	C8—C13—C9	118.91 (15)
H2A—C2—H2B	107.5	C6—C14—H14A	109.5
C2—C3—C17	109.89 (16)	C6—C14—H14B	109.5
C2—C3—C16	110.57 (17)	H14A—C14—H14B	109.5
C17—C3—C16	109.31 (17)	C6—C14—H14C	109.5
C2—C3—C4	107.56 (16)	H14A—C14—H14C	109.5
C17—C3—C4	109.51 (16)	H14B—C14—H14C	109.5
C16—C3—C4	109.97 (16)	C6—C15—H15A	109.5
C11—C4—C3	112.57 (16)	C6—C15—H15B	109.5
C11—C4—H4A	109.1	H15A—C15—H15B	109.5
C3—C4—H4A	109.1	C6—C15—H15C	109.5
C11—C4—H4B	109.1	H15A—C15—H15C	109.5
C3—C4—H4B	109.1	H15B—C15—H15C	109.5
H4A—C4—H4B	107.8	C3—C16—H16A	109.5
C12—C5—C6	111.83 (15)	C3—C16—H16B	109.5
C12—C5—H5A	109.2	H16A—C16—H16B	109.5
C6—C5—H5A	109.2	C3—C16—H16C	109.5
C12—C5—H5B	109.2	H16A—C16—H16C	109.5
C6—C5—H5B	109.2	H16B—C16—H16C	109.5
H5A—C5—H5B	107.9	C3—C17—H17A	109.5
C15—C6—C14	109.56 (17)	C3—C17—H17B	109.5
C15—C6—C5	109.34 (16)	H17A—C17—H17B	109.5
C14—C6—C5	110.85 (17)	C3—C17—H17C	109.5
C15—C6—C7	110.20 (17)	H17A—C17—H17C	109.5
C14—C6—C7	109.58 (17)	H17B—C17—H17C	109.5
C5—C6—C7	107.28 (16)	C23—C18—C19	116.87 (17)
C8—C7—C6	114.26 (16)	C23—C18—C9	118.85 (16)
C8—C7—H7A	108.7	C19—C18—C9	124.25 (16)
C6—C7—H7A	108.7	C20—C19—C18	121.75 (18)
C8—C7—H7B	108.7	C20—C19—Cl1	117.22 (15)
C6—C7—H7B	108.7	C18—C19—Cl1	121.03 (15)
H7A—C7—H7B	107.6	C21—C20—C19	118.76 (19)
O3—C8—C13	120.01 (17)	C21—C20—H20	120.6
O3—C8—C7	121.26 (17)	C19—C20—H20	120.6
C13—C8—C7	118.70 (16)	C22—C21—C20	121.69 (19)
C10—C9—C13	109.02 (14)	C22—C21—Cl2	119.39 (18)
C10—C9—C18	111.39 (14)	C20—C21—Cl2	118.91 (17)
C13—C9—C18	110.31 (14)	C21—C22—C23	118.6 (2)
C10—C9—H9	108.7	C21—C22—H22	120.7
C13—C9—H9	108.7	C23—C22—H22	120.7
C18—C9—H9	108.7	C22—C23—C18	122.25 (19)
C11—C10—C1	118.05 (17)	C22—C23—H23	118.9
C11—C10—C9	123.28 (16)	C18—C23—H23	118.9
C1—C10—C9	118.66 (16)